Karen's Sissy Adventures And Rantings

The Bet - Chapter 46 (Tuesday – week 7 Part 9 of 9)

2012-01-27T02:59:00.001-08:00

The Bet
by Karen Singer

Chapter 46 (Tuesday – week 7 Part 9 of 9)

Mel sat back comfortably in the rich seats of Ray’s Cadillac. Dinner had been really great. Expensive, at least for Ray since he had paid for everything, but it had been worth it! The food had been fabulous and the service even better. Conversation had been light and interesting. Not the least sign of stress at all. And so far, Ray had been the perfect gentleman… perfect! Of course, they both already knew where this evening would be heading later. But Mel was really glad to see that Ray wasn’t overly anxious to get to that point yet.
And now they were on their way to one of the clubs that Ray liked. He had said it was a fun place. She had never been there, but from Ray’s description it sounded like a good time. She would just wait and see. So far, everything had been perfect. The dream date!

Chad, once again clad in his blue sissy little-girl dress, stood in front of everyone and curtseyed – he didn’t dare not curtsey! The beating he had just gotten made sure he didn’t want to mess up at all. Every eye in the room was watching him intently! Being very conscious to make sure he was using his sissy voice correctly, he began singing:
“Mawy had a wittwe wamb, wittwe wamb, wittwe wamb. Mawy had a wittwe wamb, it’s fweece was white as snow.”
Chad saw Jillian shake her head discouragingly. But he continued.
“It fowwowed hew to schoow one day, schoow one day, schoow one day. It fowwowed hew to schoow one day, which was against the wules.”
“Stop!” Jillian shouted. She looked over at Sandy. “It’s not right! It’s just not right!”
Sandy just shrugged. “That’s what we came up with. It sounded like he did it right to me. And you have to admit, it was funny!”
“It was!” Stacy agreed. “I thought so anyway.”
But Jillian didn’t look convinced. “Yeah, yeah. It was pretty good and all, and I like the higher pitch voice he’s obviously using, but it’s just not right. I mean, look at him. He’s supposed to be some kind of a baby… or a toddler or something. A major sissy at any rate! And I think he could sound a lot more babyish.”
“Well,” Sandy replied. “I have been teaching him to talk in only baby talk. But if he does that, then nobody can understand anything at all since he isn’t allowed to use any real words.”
“No, that’s not what I mean. I mean… kind of like what you’ve got him doing, only more so.”
“Okay,” Sandy replied. “What did you have in mind?”
Chad stood there and just listened to it all, not liking one bit what he suspected they were proposing. It had been hard enough learning to talk like the way he was, he couldn’t imagine it getting any worse.
Jillian thought for a moment. “Well, first of all, I thought most sissies were supposed to lisp all the time. Why doesn’t he?”
“I don’t know. I guess we didn’t think of it.”
Jillian turned to Chad. “Okay, so lisp.”
Lisp? He curtseyed. “Did you want me to do Mawy Had A Wittwe Wamb again?” he asked.
“Sure, anything,” Jillian replied. Just lisp when you talk from now on.
But Chad wasn’t all that sure about… how. He thought he did, but since he had never actually done it, he figured he better ask. He curtseyed – lest he get punished again. “How?” he asked.
Jillian looked at him in shock. “You don’t know how to lisp, and you’re a sissy?” She shook her head. “Just stick your tongue between your teeth any time you come close to anything that sounds remotely like an ‘S’.”
Chad mulled that over in his head. It pretty much jived with the concept that he already had. He thought about it… esss… eththth. It was awkward, but not all that hard – he didn’t think, or he hoped. He curtseyed for everyone again. And instead of singing, he spoke fairly slowly and carefully:
“Mawy had a wittwe wamb, wittwe wamb, wittwe wamb.” Whew! No ‘S’s yet! “Mawy had a wittwe wamb it…th fwee…th wa…th white ath…thnow.” Whew! Just that little bit took more out of him than he thought it would.
“Good,” Jillian proclaimed. “Well, it’s a start anyway. Do it again! Try keeping your tongue between your teeth more so it’ll be in position and ready for it.”
Once again Chad repeated what he had just said, being more conscious of where he tongue was in his mouth. This time, he was surprised that it came more naturally.
Cassie giggled when he finished just that little bit. “It does sound sillier, doesn’t it!”
Jillian only smiled. “But I still don’t like it.”
Chad was fairly sure he had done it correctly. But she didn’t like it?
“I don’t think some of the other things he’s saying sound… childish enough.”
“Like what?” Sandy asked, totally mystified. As far as she could see he sounded totally childish.
“Like… I don’t know.” She turned to Chad. “Say it again. Slow.”
Chad curtseyed and started yet again. “Mawy had a wittwe wamb…”
“Stop! I don’t like little… or wittle… or however he said it. Make it more like… widdwe. Change the ‘T’ sounds to ‘D’ I guess. Now try it again.
Ugh! This was getting harder and harder! But he had no choice but to do as he was told. He curtseyed. “Mawy had a… widdwe wamb, widdwe wamb, widdwe wamb. Mawy had a widdwe wamb, it…th fweeth wath whide…” He realized he had automatically changed the ‘T’ to a ‘D’ on that word. “ath thnow.” Whew! Difficult!
Jillian just smiled, but all the other women were laughing.
“I want to hear him say something else,” Stacy said.
“Like what?” Jillian asked.
“Say my name,” Stacy told Chad. “In fact say all of our names.”
Chad started with Stacy. “Thathy.” All the women broke into peals of laughter. Basically, his tongue felt like it had been between his teeth for the whole word. Weird! He turned to Jillian next. “Jiwwian.” No ‘S’s Hooray! He turned to Cassie. “Cathie,” he said, drawing the th sound out a bit.
“Well,” Cassie said, “my name is Cassie, not Cathy, but I guess it’s close enough.”
Finally Chad turned to Sandy. “Thanthy.” Woops! He had messed up! “Thandy!” he corrected himself as he tried it again. All the women were laughing again. Keeping his tongue closer to his teeth had caused him to make a mistake.
“It’s okay,” Sandy told him as she was still laughing. “I like it better the first way! It was perfect!”
Embarrassed, Chad looked for a way out of what he was doing. He curtseyed, and carefully trying to lisp as he asked, “Can I pweathe get my bottwe? I don’t want to mith getting my dipwew to weak on time.”
“Yeah, you better!” Sandy agreed. “We don’t want to have to beat you again. But hurry up about it.”
“Wait a second!” Jillian interrupted. “I think he needs to ask a bit better than that. I didn’t like the way it came out.”
“But he needs to keep drinking,” Sandy objected.
“This should only take a second,” Jillian replied before turning back to Chad. “Now ask if you can get your bottle again. Let’s see what we can do with it.”
Chad was definitely getting frustrated. But he curtseyed before he spoke anyway. “Can I pweath get my bottwe?”
Jillian shook her head. “First of all, change the word ‘get’ to ‘ged’. Forget the ‘T’s. But mostly, I don’t like the way you said bottle. Let’s see… Like before, try changing the ‘T’s to ‘D’s.
Chad curtseyed once again. “Can I pweath ged my boddew?”
Jillian just stared blankly at him for a moment. “There’s got to be some better way for him to say bottle. I just don’t like it.” Mostly to herself, she started trying to sound out letters to see what might work. “Bottle… Boddew… Bobbew… Bob… Bob…” But nothing really good was coming to her.
“How about just ‘ba-ba’ Sandy suggested. Don’t some kids call it that anyway?”
Jillian thought about that and smiled. “Perfect!” She looked back at Sissy. “Got that! From now on it’s ba-ba instead of bottle! Now ask again.”
Ba-ba? He would have rolled his eyes or shrugged his shoulders, but he didn’t want to make anyone angry at his attitude. So he just curtseyed. “Can I pweath ged my ba-ba?”
Jillian smiled. “I like that so much better!” She looked over to Sandy for her opinion.
“I love it too!” Sandy agreed. Then she turned to Chad. “So please… go get your ba-ba and hurry up about it! Get drinking!”
Chad hurried off toward his diaper bag to grab another bottle – ba-ba. Geez! He couldn’t wait to get out of here tonight. Once he got home, he would never have to worry about all this junk again! None of this is what Mel wanted him to do! He but his bottle to his mouth and took a very long drink, mostly to stall, before carrying it back to where he was before.
When he got back to the ladies, Jillian was gone. She came back a few moments later with a long willowy pole in her hands and took her seat. And then they started in on him again, except that this time, anytime he said something that one of them wasn’t happy with, Jillian quickly flicked the narrow end of her pole out and caught him on the leg – which stung like hell!
Say this… Say that… It never ended! And it wasn’t just Jillian now, it was all of them. Like they had all gotten drunk and thought it was the greatest game ever. Over and over again, each of them had ideas for making him sound more and more childish… or silly… or… sissyish! And every time he messed up in the slightest, Jillian’s pole would let him know it in the worst way. The only respite he got was the frequent drinks they allowed him from his “ba-ba.”
Eventually, Sandy had him skipping around and around the living room as he sang or even just talked. And worst of all, the skipping while talking or singing was causing him to get used to the new talking requirements faster than ever. If he just relaxed and didn’t think about it, it almost became natural to him. And best of all, Jillian’s weird whip wasn’t raising more welts on his legs.

Mel leaned into Ray’s big body and held him tighter for a moment. The music was nice, for a change it was slow and pretty. A big change from most of what had been playing previously. They danced almost – intimately. She felt him rubbing himself ever so slightly against her – her breasts, further down… Hinting at what was still to come – later.
When they had first arrived, the place had seemed fairly empty. Now, it was starting to feel much more crowded. The music had been getting louder, as had the noise level from everyone talking. Ray had courteously bought her two drinks already, although she noticed that he had only had one. Well, he was driving.
The music ended, and started again. Another fast one! With a mischievous smile, she stepped back and started moving wildly, almost daring him to keep up – which she noticed he did his best to try. Not bad! Not bad at all! She was having… fun!

Chad was getting tired. Major tired! He was hitting his bottle more and more just to keep his voice from going horse and his legs were beginning to tire from skipping everywhere and getting whipped. But the one good thing from it was that as he skipped around the living room, he suddenly realized his diaper was leaking – a full fifteen minutes early. Fantastic! His backside still stung miserably from the beating Jillian had given him earlier. He stopped in midstride from where he had been skipping and singing like a little girl – or a fool! “I’m weekin!” he suddenly declared as he pulled his voluminous skirts up to show everybody his wet diaper.
“Wonderful!” Sandy praised him. In truth, she was really glad he had made it. She didn’t want to see a repeat of what had happened earlier – or possibly worse! “Go get your diaper bag.”
Chad went and got his diaper bag – without skipping. He really was getting tired. He had been the source of their amusement for a long time now and as much as he loved the humiliation, he was more than ready for it to end. How long were they going to stay anyway? He carried the bag back to Sandy who had just knelt down in the middle of the floor. He supposed this diaper change too was going to be another source of amusement for the ladies. Oh well. It was kind of fun. He laid down in front of Sandy and a moment later, accepted another baby bottle that she pulled out of the bag for him.
Sandy half expected Jillian to ask to change him- she had pretty much run the show with everything else all night. But Jillian was staying silent about this. Sandy didn’t really blame her. But as long as Sissy was just wet, she really didn’t mind this little chore at all. It was just like taking care of a baby. A big baby, but still a baby. The comparison was even more so with the bottle in his mouth.
In short order, with everyone looking on closely, she had him once again in a dry diaper with another hour and forty-five minute time limit. She allowed him to stay on the floor where he was and drink his bottle while she packed up his diaper bag again. She kind of felt sorry for him in a way. Everyone had been on him all night long trying to teach him to talk more like a toddler. And the funny thing was, it was working. And she herself was loving it. Of course, she was totally fascinated with Sissy’s baby side. Totally! And this was just another way of adding to it. If she had thought of some of these things before, she would have brought them up to Mel.
Mel! She really couldn’t wait to tell her about what they had doing tonight. She just knew Mel would love it. Especially once Mel actually got to hear his new voice. As she got up from the floor, Stacy was already hungry to hear more of Sissy making a fool of himself. Well, that’s what he was here for…

“I said, it’s getting awfully noisy in here!” Mel shouted close to Ray’s ear.
Ray looked around. The place was jam packed! He wondered if Mel might possibly be ready to go home yet. He was certainly ready – for a little love making. He had been ready for that all night long. But he knew from experience that women wanted to be shown a good time. So he had attempted to do just that. He leaned down close to her ear. “Are you ready to get out of here?”
Instead of answering vocally, Mel just nodded. It was a lot easier than shouting. And her voice was getting tired from trying to talk that loud.
Five minutes later, they finally made it out of the building and into the fresh, clean night air. Both of them breathed in deeply to clear their lungs. Both of them were glad to be away from the assaulting noise of the music inside. Ray opened her car door for her and she got in. Quiet at last. Would he ask to take her home now? She hoped so.
Ray got into the car. “I told you it was a great place,” he said. “Where to next? Another club or perhaps a quieter bar somewhere where we can get a drink?”

But Mel had already had enough. “How about my place?” she asked. “I’ve only got wine there, but there’s plenty of it.”
Ray just smiled and drove her home. When they arrived, Mel noticed that Cassie’s car wasn’t there. She really hoped that Sissy was having a good time.

Crawl, babble, drink from the bottle, put the toys in his mouth, act like a fool. Sandy was showing off the way she had been training him to act totally like a baby. The only good part was that he didn’t have to use their stupid version of his sissy voice. Now if only Sandy would keep him using his “baby” voice for the rest of the night, things would go a lot easier.
“It’s boring!” Stacy suddenly declared. “I mean, it’s nice and all, but it’s just boring!”
Sandy looked back at Sissy with disappointment. None of them got the kick out of him in this state the way she did. But she guessed she understood. Stacy and especially Jillian were more into the “action” kind of thing where something more exciting was happening. But she was beginning to worry that Sissy had already been through more than enough. She didn’t want to abuse this opportunity that Mel had given her to “play” with Sissy. She glanced at Cassie. “I’m thinking we need to get this baby home and in bed.”
Cassie nodded. “Yeah, it’s getting about that time.”
“Aw!” Stacy lamented. “But it was really fun, especially watching him jumping and skipping around earlier.” She giggled again at the memory of it.
Chad was totally elated. He just wanted to go home – and to bed would also be nice! And fortunately, in short order, he was once again buckled into the back seat of Cassie’s car while drinking another baby bottle for the ride home. Whew! What an evening! Difficult, not to mention painful. His backside was still stinging badly, and there were sore spots on his legs as well from Jillian’s whip. But… it had still been fun.
As Cassie pulled into the parking space, Sandy noticed a nice looking Cadillac in one of the other spaces. She was pretty sure that it was the same car Mel and Sissy had taken on their date Sunday. The one belonging to Ray. She hoped Mel was having a good time.
While Cassie carried their bag of the baby things she kept for Sissy up to their apartment, she carried the diaper bag and led Sissy up to his own apartment. It was time to get him ready for bed and Mel had specific instructions for that too.

His lovemaking was wonderful. His member huge and firm inside of her – feeling ever so good. Better even than the huge strap on dildo had been, because this one was alive. It was real! His hands seemed to hit every wonderful place at exactly the right moment. Though she was surprised at his skill, she realized that she shouldn’t be. This was what he did, almost every night. But even as she allowed herself to enjoy every single sensation of it, she also realized there was something larger that was missing. Some key ingredient that she couldn’t put her finger on. Yet obviously, whatever that ingredient was, it wasn’t necessary for her to enjoy some of the best sex she had had in a long time. If ever!
Eventually, they finished and she felt like a warm wet noodle. All soft and relaxed. He leaned over and kissed her passionately one more time before getting out of bed. “Stay there,” he said. “No need to get up.”
Mel laid there snuggled naked under her covers and watched as he got dressed again. Such a nice body. Then he came back and gave her one more kiss and said goodbye. She stayed right in bed as she heard him opening and closing the apartment door. What an evening.

Just as Mel instructed, Sandy removed his now overly soaked single diaper and cleaned him up. She felt lucky that he didn’t pee all over the place as she did it. Cassie had told her in intimate detail about that happening at the gym. She grabbed the jar of suppositories and pulled one out. She lifted his legs up high and “pretended” to push the thing up inside of him. Then she returned the suppository that she had palmed back to the jar as she closed the lid. All through it, Chad just laid there and sucked on his bottle – like a big baby. She almost giggled.
The hardest part was getting four disposable diapers on him, but she eventually managed, sealing all of them up with a pair of plastic panties on top. Then she went to his refrigerator and brought back four more bottles for him to drink before he went to sleep. She leaned over and kissed him. “Good night, Sissy.”
She left his apartment to go home. Just as she got to her own apartment door, she heard the noise of another door opening and closing. She turned to look and saw Ray leaving. He gave her a big smile and a little wave before he headed down the stairs to his car. It looked like Mel had a good time tonight too. She smiled as she opened her door. No doubt, she would also have a good time with Cassie tonight. No doubt! She was very much looking forward to it now.

Mel laid in her bed and thought about tonight. She had been away from Sissy for most of the night. It was good… but for some reason she missed him. Did he have a good time like she did? Sandy had called her friends kinky. She wasn’t quite sure what that meant in this case, but as long as Sandy seemed to think it would be okay, she was fairly sure it would be.
Ray had been great. All night long. The perfect date. But as she laid there staring at the dark ceiling, she realized exactly what had been wrong – all night long. He had been too perfect. Everything he had done had been too practiced. As great as he had been, there had been an element of… intimacy?... that had been missing. This was what he did every night – with a different woman. He was like a… a gigolo. Except she hadn’t paid him. He had paid for it all, spending all evening trying to impress her with his manners and his money. Well, she wasn’t impressed with money. She had money. Tons of money. Money she never touched or hardly even thought of. Money that, as soon as she won this bet, she would dip into for the first time in her life. But first, she had to win the bet!
She thought again about Sissy. Did he have a good time tonight? Did Sandy manage to keep him on his wetting schedule? She really hoped so. Did Sissy really cook only hamburgers for them for dinner? How did it turn out? She would have to wait till tomorrow for answers.
She thought of one last thing. She always went to his apartment every night and set his alarm and left him a note. But tonight, well, she was still feeling all warm and wet and spent. Too good to get out of bed. Besides, the note would be exactly the same as it was almost every night. So she decided to skip it. Hopefully, in the morning, he would still know what to do. He’d better!
Very softly she whispered into the dark of her bedroom. “Good night, Sissy. Sleep well.” Then she turned over and fell soundly asleep.

The Bet - Chapter 46 (Tuesday – week 7 Part 8 of 9)

2012-01-24T03:02:00.001-08:00

The Bet
by Karen Singer

Chapter 46 (Tuesday – week 7 Part 8 of 9)

Chad surveyed the dinner, such as it was. Hamburgers… and chips. Not much. Why had they even wanted him to cook? But he had done the best he could. He had “snitched” a bit of one of the burgers to test it and surprisingly, the seasoning mix had done a fairly good job. They didn’t taste too bad at all. Too bad he wouldn’t be getting to eat any of it. Baby food was most likely his lot.
He glanced at the clock. It was already eight minutes past his deadline. He was a lot closer to leaking now, but it still hadn’t happened yet. He prayed it would soon because every minute meant that much more misery. He went into the living room where everyone was talking. The minute he entered he caught everyone’s attention. He curtseyed. “Dinner is ready.”
“About time!” Stacy complained as she hefted herself out of one side of the couch.
Chad stood back and watched as each of them found a place at the table.
“Get me a coke!” Jillian ordered.
Chad ran to the refrigerator. “Diet for me,” Stacy called next.
“Me too,” both Cassie and Sandy said at the same time.
Chad pulled the cans out of the refrigerator and set them all on the counter. One by one he opened each one and handed them out. Then he stood back again to see if anybody would want anything else. He watched as Jillian picked up one of the hamburgers and took a huge bite out of it. Then her face seemed to register shock… then rage.
“Shit!” she said angrily with her mouth still full. “What did you do to it?”
Chad stammered. “I just… added some seasoning to make them taste better.”
“They’re not supposed to taste better,” Jillian returned. “They’re supposed to taste the same!”
Chas saw Stacy take a tiny bite of hers. Her head cocked to one side as she tasted and chewed it. “Mmmm. I think it’s pretty good.”
Sandy and Cassie each took a small bite of theirs and both of them agreed with Stacy.
“Shit!” Jillian exclaimed as she grabbed a handful of chips.
Sandy glanced up at the clock. “You’re going to be in for it, I’m afraid,” she said to Chad. “You better start leaking soon.”
Chad curtseyed, and realized that nobody had said anything about him not curtseying a minute ago. He wasn’t going to bring up the point either. “I’m trying,” he said again. “I’m really trying!”
But it was Jillian, with her mouth full of hamburger who answered instead – without so much as glancing in his direction. “Try harder!”
Chad grabbed his latest bottle of water and started drinking again as the women sat and ate and talked.

“This is so good!” Mel exclaimed as she took another bite of the deliciously broiled fish in front of her. She didn’t often eat seafood and had never been to this restaurant, but this was where Ray had taken her and she had to admit, it was a great place.
“I can’t believe you’ve never been here,” Ray said as he took a bite of his own dish.
“I never had a reason, I guess,” Mel replied. “Actually, I never even thought of coming here. It certainly is a nice place though.” She looked around the room and was glad she had dressed up tonight. All the other women were very nicely dressed too, as were the men. The word “swanky” came to mind. She had a feeling that Ray was out to impress tonight. Well, she was certainly impressed so far. Not that it mattered. Ray himself looked awfully good in his nicely tailored suit. He was more than handsome, he almost bordered on… pretty. Pretty handsome? She almost laughed. The guy was a hunk!
She took another sip of her wine, and as she set her glass back down, a formally dressed waiter was suddenly at her side. “Can I pour you another glass madam?” he asked quietly. She nodded. This was so nice!
“So, did you wear that dress in court today?” Ray asked.
Mel’s eyes went wide. “This? In court? Actually, I didn’t have any cases in court today. But I’d never wear this there!”
“Why not? I’ll bet the judge would be easily swayed by someone looking like you.”
Mel laughed. Small talk. And it was so nice.

“I’m leaking!” Chad suddenly exclaimed.
All talk at the table ceased and all heads turned in his direction.
“It’s about time,” Sandy replied as she glanced at the clock. “Geez! You’re twenty minutes late!” She turned to the women at the table. “This is going to take a while,” she said.
Jillian never even raised an eyebrow. “You got anything better to do tonight?” she asked as she stuffed the rest of her hamburger into her mouth.
Chad didn’t know what to do. He was just standing there, leaking, while the women were all eating and talking as if they didn’t care in the least about him. But then, if they planned on punishing him, then he wasn’t the least bit anxious for them to pay that kind of attention to him. With nothing better to do, he just stood back out of the way and continued to drink more bottles as the women seemed to enjoy their dinner.
He saw both Sandy and Cassie push back their plates early. They had each not even touched their second hamburgers. It was a while before Stacy and Jillian finished their meal. Chad noted that even though Jillian had complained about the way he had made them, she had finished two full hamburgers.
“I think it’s time to play ‘Beat the Sissy!’” Jillian suddenly announced as she pushed her plate back.
Chad’s eyes went wide as he watched everyone getting up from the table. Beat the Sissy?
“Let’s go doll,” Stacy said as she headed for the living room. “I’ve been looking forward to this all day.”
Chad inwardly gulped as he nervously followed everyone into the living room. He noticed that Jillian went straight through into another room, the bedroom he was guessing.
“Well don’t just stand there. Get that dress off!” Stacy ordered.
Even more nervously, Chad began removing his dress. Mel usually beat his naked bottom. Were these women going to do the same?
Jillian came back a few minutes later, her arms loaded with things that immediately sent fear into Chad’s heart. He saw handcuffs, and chains, and what looked like leather cuffs all jumbled together. She dropped all of it on the old scarred coffee table. “How do we want to do this now?” she asked everyone.
“I want him across my lap!” Stacy exclaimed immediately.
But before they could go any further, Cassie thought of a point she figured she better raise. “Um… I think we need to keep in mind that Mel has been training him to be totally incontinent. Whatever we do, we better plan in case he pees all over the place.”
“Shit!” Jillian exclaimed. “Is he that far gone?”
“Trust me,” Cassie replied. “I’ve seen it with my own eyes.”
“Yuck!” Stacy exclaimed. “That’s going to ruin everything! It’s not as much fun if we can’t spank his bare bottom!”
“You could try protecting your lap with a couple of diapers,” Cassie suggested. “That should work, I would think.”
“You think?” Stacy asked hopefully.
Cassie nodded. “It should.”
But it was Jillian who was all action. “Get that diaper off sissy boy!” Then she turned to Stacy. “Your usual paddle?”
Stacy just smiled wickedly. “Yeah! That’s what I want.” She glanced at Chad who’s diaper was just hitting the floor, revealing the chastity device underneath. “Holy cow! Look at that!”
Jillian paused in mid-stride toward her bedroom and came back to see. She stared in amazement and moved in for a closer look. “I don’t believe it!” she said. “I never actually saw one of these before.” She reached out and grabbed his chastity device and gave it a bit of a tug. “It’s on pretty secure!” she said.
Stacy who had been prying herself off of the couch, finally arrived and leaned over for a closer look too. “Damn!” she said as she reached out to touch it. She too pulled on it a bit, causing Chad to lurch off balance for a moment. “He ain’t gonna get no fun with that thing!” she announced. She looked up straight into Chad’s eyes. “Are you?”
Chad just shook his head, totally embarrassed. “No,” he replied.
“Hey!” Jillian exclaimed. “He didn’t curtsey before he spoke!” She looked back toward Sandy, “So that means we can punish him for that too?”
Sandy smiled. “That and he also missed it twice earlier!”
Jillian’s eyes lit up. “I’m gonna enjoy this!” With that, she hurried off to the bedroom.
“So go get me some of your diapers to protect my dress,” Stacy ordered. “And hurry up!” Then she went back to settle herself on the couch again.
Chad didn’t exactly hurry to his diaper bag, in fact he tried to take his time about it. But the apartment wasn’t that big so getting a few diapers didn’t take very long. Reluctantly, he handed the diapers to Stacy who spread them out as much as possible to protect her clothes. By the time she was ready, Jillian was just coming out of the bedroom again. A muted smacking caught everyone’s attention as Jillian smacked the paddle in her hand against her other hand. Chad turned quickly at the sound, but Stacy was more than ready for him and grabbed his arm and pulled him off-balance, down onto her lap. Fortunately, with a cry of alarm, he landed pretty much right where she wanted him. With a loud smack, her bare hand hit his bare backside. “Ha!” she exclaimed. “Perfect!” She took the paddle that Jillian held out to her and held it up to show to Sandy and Cassie. The paddle had holes drilled through it at various places. “Now hold still Sissy!” she said. Crack!
Chad’s whole body jolted and he cried out in pain. He hadn’t expected it to hurt that much. How could he have ever considered this monster as “sweet?”
“Make sure you warm him up good for me,” Jillian said.
“Don’t worry,” Stacy replied, “I’ll have his sweet little ass a nice cherry red in no time.”
Cassie and Sandy looked at each other as Stacy began wailing away at Chad’s backside – and Chad began wailing in pain. They hadn’t expected for Stacy to take such a role tonight. Jillian was the one they really expected to punish Sissy. Not only that, but Jillian and Stacy were pretty much acting like Sandy and Cassie weren’t even there. After watching Stacy spanking Chad for a few moments, Cassie leaned over and whispered to Sandy, “I’m glad we’re not doing the spanking tonight. I think he’s had enough already.”
“And they’ve just started,” Sandy replied. “Jillian hasn’t had her turn yet.”
Cassie nodded. “We might have to step in if it gets too bad.”
This time, Sandy nodded. “Hey,” she called to Stacy. “He was only twenty minutes late. Don’t overdo it.”
Stacy just smiled back wickedly. “Don’t worry, I’m not hitting him all that hard.”
Chad had a different opinion about that. He couldn’t believe how much her paddle hurt! He kept writhing around on her lap as she hit him. A few times he tried putting his hands back over his backside to protect his aching flesh, but each time her paddle landed squarely on his hand, hurting him even more and forcing him to take his hand away again. He finally writhed himself into such a position that with another cry of alarm, he fell on the floor.
“Damn!” Stacy cried. “What did you do that for?”
“My turn!” Jillian declared. “And it looks like we’re going to have to make sure you won’t get away like that again!”
Before Chad could get up from the floor, he suddenly had Jillian sitting on his back, keeping him there. She grabbed his arms and pulled them back behind him. She only held them there for a moment before he felt something cold and hard begin fastened to one wrist. A second later, the handcuffs were on securely and his arms weren’t going anywhere.
Jillian got off of him and looked around. “Now, let’s see. Where shall we put him?” Her eyes finally landed on the coffee table and stayed there. “I think that will do,” she declared. With one swift push of her arms, all the bondage junk she had deposited there earlier went flying off onto the floor. She reached down and grabbed Sissy by his arms that were locked behind his back and helped haul him to his feet. She led him over to one end of the coffee table. “Lay down on it!” she ordered.
“Hey!” Stacy cried, catching everyone’s attention. She held up one of the diapers that had been protecting her lap. “He peed on it!” Everyone but Chad laughed a bit.
Jillian grabbed the wet diaper from Stacy’s hand and threw it down on one end of the coffee table. She pointed her finger at it for Chad’s benefit. “Down!” she ordered.
Chad thought about defying her, but with his hands cuffed behind his back he wouldn’t get very far. Slowly and carefully, he did his best to lay down on top of the coffee table so that the part of him the really needed the protection of the diaper was right on top of it.
Jillian went into action and quickly sorted through the junk on the floor. Leather cuffs were quickly attached to each of his ankles and the ankles were in turn chained to the legs of the coffee table, making sure that his rosy red backside would stay right where she wanted it. Then it was her turn with the paddle. Before she started, she leaned down close to Chad’s head. He voice was almost a whisper. “I understand that you have deadlines, and from what I’ve just seen, you have trouble meeting them. Well, I’m going to give you something to think about to help encourage you to try a lot harder.” She stood up and moved back behind him. Grabbing the handle of the paddle with both hands, she swung it as hard as she could, connecting it with his backside.
The sound of the smack was loud, but Chad barely heard it as his body was too preoccupied by the pain that had been induced. He cried out in alarm, but all he got for his effort was another smack on his other butt cheek. He writhed on the table, but with his hands cuffed behind his back and his legs straddling the table and chained to the table legs, there was no place he could go. Jillian repeated the blows again to each of his butt cheeks.
Sandy looked at Cassie once again. A spanking was one thing, but Jillian was swinging awfully hard. They didn’t want her to hurt Chad. But just then, they saw Jillian look up and wink. Sandy held off from saying anything and waited to see what would happen.
Jillian bent down to speak softly in Chad’s ear again. “That was just to let you know what I’m capable of and that I’m serious about this. Just so you’ll have something to think about for the future.”
Chad heard her, but his mind was mostly focused on the incredible pain from how hard she had hit him. “No more,” he blubbered. “Please, no more.”
“Oh, there’s going to be more. I’ve only just started. Like I said what I just gave you was just something to think about. What I’m capable of doing. Now I’m going to give you your real punishment. After this, maybe you’ll try harder to get your diapers leaking on time… not to mention learning to curtsey when you’re supposed to – sissy boy!”
She stood up again and moved back behind him.
“No…” Chad pleaded as he started crying before she had even hit him again.
She didn’t hold the paddle with both hands like before. And she didn’t even try to hit him with all her strength, but she didn’t go all that easy on him either. As fast as she could, she pounded away on every square inch of his backside, reddening it far more than the little warm-up that Stacy had done. Only when she was satisfied with the way that it looked did she finally stop. Sissy was crying and sobbing pitifully.
Jillian went back towards his head to speak with him. “Are you going to be a good sissy boy now?” she asked.
“Y…Yes!” Chad barely managed to get out as she sobbed.
“Are you going to try even harder to make your diapers leak on time?”
Again Chad barely managed to answer… “Yes.”
“Are you going to remember to curtsey when you’re supposed to?”
One last time, Chad blubbered out his barely understood, “Yes.”
Jillian looked up at Sandy and Cassie. “You know, I really think we should work on the way he speaks. I’m sure we can… improve it.” She suddenly had a very big, very wicked grin on her face.
After seeing the beating that she had just given Chad, Sandy was ready for anything that wouldn’t be so violent. She looked over at Cassie. “Sounds like a good idea to me. What do you think?”
Cassie was of the same mind as Sandy. “I think it’s a great idea.”
Sandy remembered something else though. “Maybe we should feed him his dinner first, if you don’t mind. I don’t want Mel to be mad at me for forgetting it.”
But Jillian was all smiles. “Sounds good to me. And I think there’s still a couple of hamburgers leftover from dinner.”
Now it was time for Sandy to smile. “Oh no! He doesn’t get that! He’s too much of a baby. I brought plenty of baby food for him. And tonight, I figured it would be more fun if we fed him.”
Jillian brightened even more. “We’re going to feed him?”
“Trust me,” Cassie replied, “it will be a lot less messy this way!”
Jillian and Stacy were suddenly all giggles. “Should we do it at the table?” Stacy asked.
Sandy looked around. “Actually, we can do it right here if you like. We just need to get him sitting up… And I think it would be a good idea to put another diaper on him and set him on his next time limit.”
“Oh yeah,” Jillian replied. “I almost forgot about that.”
While Cassie and Sandy went to get his diaper bag and their big bag of other things, Jillian began unfastening his legs from the coffee table. “Hey,” she called. “How about his hands? Should we leave them or do you need me to take the cuffs off.”
Sandy looked at Cassie, but Cassie was already answering. “Leave them!”
A few minutes later, Chad, his arms still handcuffed behind his back, and still trying to get his crying under control, laid painfully down on the floor to let Sandy put a fresh diaper on him. Sandy wanted to say something to him about the beating he had just gotten, but she didn’t want to upset either Jillian or Stacy, so she said nothing about it. “An hour and forty-five minutes,” she said as she finished and checked her watch. “I hope you make it this time. I ‘really’ do!”
When he was ready, Sandy had Chad straddle the coffee table again and sit on it, which was obviously very painful to him – which brought giggles from both Stacy and Jillian.
Cassie tied a big bib around his neck while Sandy started pulling jar after jar out of the plastic bag. Twelve jars in all. Every jar containing something different.
“Can we feed him too?” Stacy asked.
Sandy smiled. “Do you have four spoons? We can all feed him.”
Within minutes, they all had a spoon and each woman grabbed a jar of baby food. Sandy went first. “Open wide,” she said. Chad opened his mouth and let her spoon the mushy cereal into it.
“Me next!” Stacy called out. Chad hadn’t even finished swallowing before she was trying to shove the cereal into his mouth. But he opened up and took it.
Jillian was next. At least Chad had a chance to swallow before she stuck her spoon in his mouth.
Cassie was a bit more patient and Chad actually had tome to swallow and open his mouth again before she stuck her spoon inside.
But before Sandy could get a chance again Stacy was anxious to get her next spoonful of baby food into him and was pressing her spoon up against his closed lips while he was trying to swallow. Chad had no choice but to open his mouth that was again partially filled with food and let her stick it inside.
And then Jillian was back all too fast and Chad was forced to open his mouth yet again while it contained even more un-swallowed baby food. Which for some reason, both Stacy and Jillian found funny. Sandy and Cassie kind of chuckled too. Before Chad knew it, all four women were pressing the food at him faster than he could chew and swallow which caused more than a little to get all over his face and drip down onto his bib.
By the time they finally finished, Stacy and Jillian had each fed him four jars of baby food while Sandy and Cassie had only fed him two. Chad was just glad the onslaught was over. If he had know it would go like that then he would have gladly skipped dinner altogether.
As soon as the baby food was out of the way, Stacy and Jillian took turns holding one of his baby bottles to his mouth for him till he could finish it, which he made every effort to do as quickly as possible.
When he was finally finished, Sandy wiped off his mouth while Jillian finally removed the handcuffs. “Let’s get him dressed again,” Sandy told everyone. “Hey, want to see how he does ‘Mary Had A Little Lamb’? It’s a riot!”

The Bet - Chapter 46 (Tuesday – week 7 Part 7 of 9)

2012-01-20T05:17:00.000-08:00

The Bet
by Karen Singer

Chapter 46 (Tuesday – week 7 Part 7 of 9)

Mel rushed around like she was going crazy. She had to not only get ready for her date with Ray, she had to get everything ready for Sandy to babysit Sissy. She partially got herself ready, then clad in nothing but her slip, she decided that she better make sure everything would be ready for Sandy before she went any further.
The first thing she did was to make sure his diaper bag was fully stocked. And how many baby bottles should she put in it? How many would he need tonight? There was no telling. Once she had everything except the bottles in his bag, she carried it over to the refrigerator where she started stocking it full of bottles till it couldn’t hold anymore. Feeling much more satisfied now that the bag had more than enough, she went to her closet to get his dress out. Sandy had said his pink baby dress. But it wasn’t in her closet. Then she remembered that he had worn it Saturday when Robin had shown up. She quickly wrapped a robe around her and grabbed her keys. Then she hurried over to his apartment.
She found the dress in his closet. But the minute she took it out, she saw that it was a mess! When Chad had gotten angry and come home in the dress, he had smeared some of the baby food from his face and hands onto different parts of the dress. He couldn’t wear it! Well, he could, but she wouldn’t let him. Not till it was cleaned.
Groaning with frustration, she carried the dress back to her apartment. He would just have to wear something else! She had just pulled his blue dress out of the closet when she heard someone at the door. On no! Not Sandy already. The only worse thing could be if it was Ray, but he wasn’t due yet for another hour. She hurried to the door and was somewhat relieved to see Sandy there.
“His he ready?” Sandy asked expectantly.
A bit frustrated, Mel replied, “Not yet. We have a bit of a problem,” she said as she headed for her bedroom.
Sandy saw Chad up on his perch in the corner drinking a bottle, but she said nothing about it. “What problem?”
“His dress! It’s a mess. He can’t wear it!”
“Oh no! I was counting on it,” Sandy replied with equal frustration.
“He spread baby food all over it Saturday,” Mel explained as she held the dress so Sandy could see it.
“Yuck!” Sandy replied. She would just have to go with something else. “So what do you want him to wear?”
“I was thinking about his blue outfit. He does look adorable in it – especially with the matching shoes.” She held the dress out so Sandy could see it.
Sandy glanced from that to his white and pink one that she noticed was still hung up in her closet. But Mel was right. With the shoes, this dress was definitely the more childish choice. Plus, she kind of like it. But then she liked all his silly dresses. “Okay, I agree, let’s get him into it.”
“Sissy!” Mel called from her bedroom where they were. “Get in here!” Then she turned to Sandy, “I have his diaper bag all packed. And I stuck a ton of baby bottles in there for you, just so you don’t run out. I tell you, with everything I’ve got to do to get ready tonight, it’s like packing for a real baby. Maybe worse!”
Sandy giggled. “I can imagine.” Then she noticed Chad standing in the doorway.
Chad curtseyed, “You called me?”
“Get over here,” Mel said, “so we can get you dressed.”
Ten minutes later, Sandy had done another quick makeup job on him, his heels were gone, replaced by the blue mary-jane shoes, and Sandy and Mel together were smoothing his dress into place and flouncing his skirts to make sure they were as fluffed up as they would go. He wasn’t happy at all to be going out somewhere again in this dress, but unfortunately, he had no say in the matter.
And that’s when they heard someone at the door again.
“Oh no! I hope that’s not Ray already!”
Seeing that Mel was still in her robe, Sandy said, “I’ll get it.” She went to the door and opened it.
“Aren’t you ready yet?” Cassie asked. “We should have left already.”
Sandy smiled. “We’re just about ready now,” she replied. “It’s Cassie!” she yelled in to Mel.
Cassie followed Mel into the bedroom. “Yeah, I really like that dress on him!” she exclaimed. “Real good! But I thought he was supposed to wear the other one.”
“It’s messed up from Saturday,” Sandy explained.
Cassie just nodded. “So are you ready? Can we go now?”
Sandy looked to Mel. “Don’t let me stop you. You already know everything I want you to do. Just have fun.”
Sandy led the way out to the door where she picked up his diaper bag, then set it back down again. “Holy cow! What the heck do you have in here?”
“A ton of baby bottles. I didn’t know how many he would need.”
Sandy knelt down and opened the bag. All she saw was baby bottles. “I think we’ll be safe enough to remove a few. Besides, I packed the ones I have for him too.” She started removing baby bottles from his bag, till there were only four left. “That should be plenty for tonight.”
“Are you sure?” Mel asked. “You know he has to drink a lot to keep wetting.”
“Don’t worry,” Sandy replied. “I’ve got it covered. But if you’re that worried about it…” She picked up one of the bottles she had just taken out of the bag and handed it to Chad. “Start working on it,” Sandy ordered.
With no other option, Chad put the bottle to his mouth.
Mel glanced at the clock, “He’s only got fifty-five minutes left to be leaking.”
Sandy nodded. “No problem. And if he doesn’t? Well, we’ve got that covered too.”
Chad heard what Sandy had said. He wasn’t sure what she meant, but it didn’t sound good. He began attacking the bottle in his mouth with a lot more enthusiasm. A minute later, he was outside in his sissy blue dress, following Sandy and Cassie down toward Cassie’s car. When they got there, she opened the back door for him to let him get in, which wasn’t all that easy with the dress he was wearing. There was a large plastic bag taking up the other half of the back seat. Cassie and Sandy got into the car, and they headed out. Chad had no idea where they were going. What was he getting into? He worried about that. And just hamburgers? Ugh!
“We don’t have very far to go,” Sandy said to him without even turning her head. “But I suggest you finish that bottle before we get there. Otherwise…”
“Otherwise what?” Cassie laughed.
Sandy looked at her with an evil grin on her face. “Otherwise, I think we should let him off at the corner on this side of the street just before we get there and make him finish his bottle before he moves. That way, he’d have to stand there in front of all this traffic while he finishes it. And of course, he’d also have to wait for the light to change too before he could cross the street to their apartment project.”
Cassie giggled. “That sounds like fun.”
“Yeah, maybe we should do it anyway.”
“Why not?”
Sandy turned around to see the horrified look on Chad’s face. She had to force herself not to laugh. “Well, I guess we should… if… he doesn’t finish that bottle first. We don’t want to keep them waiting for dinner any longer than necessary.”
Chad began sucking much more furiously on his bottle. He had no clue how long he had to finish the thing, but he didn’t want to get left out on the street corner like this!
A few minutes later, Cassie said, “That’s it up ahead. How’s he doing with his bottle?”
Sandy turned around to look. She could see him drinking as hard as he could, but there was still a bit left in it. “Not quite done yet.” Sandy replied.
“Okay,” said Cassie.
Chad’s eyes went wide as he saw that she was moving from the left to the right lane. Would she really do this? He was drinking as fast as he could! As they approached the intersection, he saw Cassie slow down and she put her blinker on to pull over to the curb.
“Better get him out quick,” Cassie said to Sandy. “We don’t want to piss the other drivers off any more than we have to.”
Chad was almost done with his bottle. There was just a bit left. He began to make little protest noises as he continued to drink.
“What?” Sandy asked. “You’re not done yet, so this is what you get.”
Cassie stopped the car and Sandy got out quickly. She opened Chad’s door. Chad made no move to unfasten his seatbelt, he just continued to drink his bottle as fast as he could. Sandy reached over him and unfastened his belt for him. “Okay,” she said. “Out!”
But just then Chad started sucking air through the bottle. “I’m finished!” he exclaimed breathlessly.
Sandy looked to Cassie. “What do you think?”
Cassie just shrugged. “He did finish it before we actually got there.”
Sandy just nodded as if a bit disappointed and got back in the car. Chad breathed a sigh of relief. Cassie had to go up another block and turn around to get back to their destination.
The apartment project looked fairly old, which explained its semi-run-down appearance. As they drove in, Chad saw groups of people in a few places either in the parking lot talking, or talking up near somebody’s door. With that many people around, he was suddenly more worried than ever about getting out of the car.
Cassie found a parking place in front of one of the buildings. Sandy turned around to talk to Chad before she got out of the car. “Now don’t forget, according to Mel, you’re supposed to use your sissy voice all the time and curtsey before you say anything. And I’ll be watching!”
Chad’s eyes widened a bit at the mention of curtseying constantly. He wondered what else Mel had told Sandy. He said nothing as Sandy gathered up his diaper bag and got out of the car. Cassie got out too. But he was having a bit of trouble working up the nerve since he noticed a group of people standing around drinking beer not far from where they were parked.
Cassie opened the back door on the other side and started to pull out the large plastic bag. “Let’s go Kiddo!” she told him. “We’re late enough as it is.”
Chad knew he couldn’t stay where he was permanently – as much as he might like to. So he gathered up his courage and got out of the car. He did his best to hide behind or between Sandy and Cassie, but with a dress like he was wearing, that was pretty much impossible. It was only moments before he began to hear cat-calls and rude suggestive comments from the drinkers. Some of the things they were yelling were making him very nervous – if not downright frightened.
“Sissy, they seem to like you,” Sandy noted. “Maybe you can come out and visit them later.”
Chad said nothing, he just tried keep the two women between him and the drinkers as he wished that Sandy and Cassie would move a little faster. Unfortunately, instead of heading toward a downstairs apartment, Sandy led the way to the open metal staircase and began to climb. As he walked up with them, he saw some of the drinkers coming out to have a closer look. It suddenly occurred to him that on the open staircase, they would be able to see right under his dress! He pushed down as best he could on his voluminous skirts and petticoats to hide his diaper covered bottom below his dress and hurried ahead of the two women up to the top of the stairs. Only then did the constant cat-calls and laughter stop. He breathed a small sigh of relief.
Sandy led the way to one of the apartments at the top of the stairs. The door was opened promptly and amid a chorus of feminine squeals, Sandy led the way inside where she hugged the girl who had opened the door. Cassie followed after her with the huge plastic bag. She too hugged the girl. Then Chad entered, tentatively. But he stopped in the doorway and stared at the girl in front of him. She was not anything like what he expected.
“And this is Sissy,” Sandy was saying.
Chad barely heard her as he took in the girl. She was younger than he expected, he figured not much over twenty one. And she was skinny – almost to a fault. But it was her shocking blue and orange hair, all arranged so the colors stood straight out from her head at odd angles. Her ears held a lot of odd piercings, as did her nose and there was one in an eyebrow and also a ring in her lip. Another piercing decorated her bellybutton under her bare midriff top. But the biggest thing that he noticed, was… her attitude! As skinny and young as she seemed, she just exuded an air of… tough!
“Sissy!” Sandy’s complaining voice broke through his moment of surprise. “I said say hello to Jillian!”
Still standing in the doorway and feeling very embarrassed about doing it for this stranger, Chad dropped a curtsey for her and said in his sissy voice, “Hewwo Jiwwian.” He saw Jillian’s head cock quizzically to the side as if something was wrong. Obviously, she hadn’t been prepared for his sissy voice.
“Huh!” was the only reply she made though.
“And Sissy,” Sandy said next, “this is Stacy.”
Chad looked to where Sandy had indicated and saw a rather… fat girl sitting on an old beat-up couch. Where Jillian looked somewhat exotic, Stacy seemed much plainer. She even wore a simple dress and looked more like she had just gotten home from work, which he supposed she might have. He dropped her his curtsey too and said, “Hewwo Stacy.” But the minute Stacy smiled, he realized just how really different Stacy was from Jillian. Stacy looked… sweet!
He took a step further into the room and Cassie closed the door behind him. The apartment was much smaller than his. Everything in it looked second-hand, if not third-hand. And it was cluttered horribly. Not really a nice place at all.
“So you’re the sissy boy,” Jillian said, still eyeing him critically. “I’ve met a few like you… well, not exactly like you. I understand you’re more into the adult baby thing. I’ve never met one like that before.”
Chad didn’t know what to reply to it so he said nothing.
Jillian turned to Sandy. “I don’t get it though. I thought all these queers were supposed to talk with a lisp or something, not just the little things that he does with his voice.”
Her question startled Sandy. “I… don’t know,” Sandy replied. “This is what we came up with for him.”
Jillian nodded. “Well, it’s nice and all, but you should consider changing it.”
“Hey,” Stacy said from the couch. “I’m getting hungry. Maybe we should let him get started making us dinner!”
Jillian just nodded. Then she jerked her head toward the kitchen. There’s fresh hamburger meat in the fridge. Rolls and chips are on the counter. Don’t take too long!
Chad curtseyed a bit before he left.
“Grab yourself a bottle before you go!” Sandy called after him. Then a moment later added. “You’ve only got twenty-five minutes left!”
Twenty-five minutes! Chad hurried to grab a bottle from his diaper bag and carried it straight into the kitchen. Since he had gotten home from work, he had only finished a few bottles. He was wet, but not that wet. And with only twenty five minutes left, he had a good suspicion that he wasn’t going to make his deadline. But what then? He wasn’t home with Mel. What would happen? He wasn’t really sure he wanted to find out, so he did his best to drink as fast as he could while he tried to figure out the kitchen – or rather the poor excuse for a kitchen.
He opened the refrigerator and grabbed the hamburger meat. But as he closed the refrigerator again, he just stared at the package in his hand. It was definitely, the cheapest, poorest excuse for hamburger meat he had ever seen. He wasn’t even sure he wanted to cook with it. How was he supposed to make something like this taste good?
And how was he supposed to cook it? He looked around. The stove was old – did it even work? Where were the pots and pans? Where were the utensils? He quickly started opening every cabinet he could, just to get the lay of the land so he would have a general idea of what was there, which amounted to not much at all. He found a large bowl, opened the package of hamburger meat and dropped it in. At least it wasn’t frozen. He searched around for something to mix in it. Spices, onions, anything! But all he found was a little bit of salt and pepper. He was about to give up when he found an odd packet of seasoning mix for soups stuck way in the back of one of the cupboards, actually under something else. He pulled it out. He wasn’t even sure if it was still good or not, but since the package had never been opened and everything in there was dried anyway, he decided to chance it.
There were four women out there and a package of eight hamburger rolls, so he did his best to divide the meat up and make eight hamburgers. Once he had formed the patties, he had to figure out how he was supposed to cook them. As far as he knew, there was no charcoal grill available. He looked again at the oven and didn’t even want to think about possibly using that. Which left him with frying them. He found the biggest frying pan he could find and pulled it out. The handle was a bit loose and the minute he set it on the stove he realized that the bottom was all warped. The Teflon coating inside the pan was mostly missing. Ugh! But it was all he had.
“Ten minutes!” he heard Sandy calling from the living room.
He panicked a bit more and tried to drink his bottle faster. He wasn’t going to make it. There was absolutely no way. But still he tried vainly to keep drinking as he fried hamburgers. When he finished his bottle, he simply refilled it from the kitchen sink. It was the fasted thing he could do. As the hamburgers cooked, he wet a few times, always hoping that he would start leaking. But so far, no luck. He was starting to get really soaked, but he knew he was not to the leaking point yet.
He had just put three more hamburger patties into the pan when Sandy walked into the kitchen. “Are you leaking yet?” she asked.
“No,” Chad replied ruefully. Sandy glanced at the clock, “Then I guess you’re working on reverse time now. I hope it won’t take you much longer, because I think someone out there was actually hoping that you would fail.”
Chad was appalled! “Who?”
Sandy just smiled. “Don’t worry about it, either way now you were going to get the chance to find out since that’s twice now that you’ve spoken without curtseying first.”
Chad was horrified! Having to curtsey all the time was crazy! This time he curtseyed. “I’m trying,” he said, the frustration clearly in his voice. “Believe me, I’m trying!”
“I’m sure you are,” Sandy replied with a smile. “How much longer before dinner?”
Chad surveyed the burgers and what still had to be done. He curtseyed. “About ten minutes I think.”
Sandy just nodded. “Let us know… and also, let us know as soon as…” she pointed at his crazy skirts.
Chad knew she was talking about how soon his diaper would be leaking. He was trying, he thought as she walked back to the living room. He was trying! He heard the women laughing out in the living room. At least someone was having a good time tonight. He put his baby bottle back to his lips as he turned the burgers.

The Bet - Chapter 46 (Tuesday – week 7 Part 6 of 9)

2012-01-17T05:17:00.001-08:00

The Bet
by Karen Singer

Chapter 46 (Tuesday – week 7 Part 6 of 9)

Chad studied the requirements for the new project. It was nothing at all on the scale that the last project had been. But still, it had its possibilities. He just wasn’t sure about how things were going to work between him and Robin now. As such, he was afraid to make any noise at all for fear of upsetting her. Things were already “odd” enough today as it was between them.
He finally closed the file on the job requirements. He knew it all backwards and forwards, he was only waiting now on Robin. Robin, who he hadn’t heard a word from since their weird discussion a while ago. He glanced at the time. It was getting close to break time. What should he do if break time came and he still hadn’t heard anything from her? He supposed he would just stay at his desk trying to remain quiet and out of the way. To fill some time, he opened up another project that just needed a few tweaks to finish up.
Robin glanced at the clock. It would be break time soon. But she supposed she really should talk with Sissy first. She realized that she had been avoiding him. Avoiding having to deal with him… because… she tried to figure out exactly why she was avoiding him. She knew there was no real reason, not anymore. It was just that… well… she was still uncomfortable with this role and… what the heck was she supposed to do with him anyway? Was she supposed to give him a never ending series of orders or something? Was she supposed to go out and buy a leather whip and wield it on him? The image of her doing that brought a bit of a chuckle to her lips. No, nothing like that at all. It wasn’t her! Not really. Okay, sometimes she could get a bit… physical when she was pushed, but in the end, that wasn’t really her.
Okay, enough avoiding him. There was work to be done! She got up from her seat and went in to see him. “Okay Sissy, what do you think about this project?”
Chad turned in his chair and actually smiled. She was being nice again – he hoped. He had learned that she could go from nice to angry in an instant. His big question now was, did he dare not use his sissy voice? He decided to go with caution. She had said she wanted him to use it. Maybe she would get tired of it real soon. In his sissy voice he replied, “I think it wooks wike it won’t be too much of a pwobwem. But we couwd do some intewesting things with it.”
Robin almost did a double take when she heard him speaking. It was really the first time she had had to deal with his sissy voice. But the most amazing thing was, that she actually understood him. “Yeah,” she replied. “That’s kind of what I thought too.” She and Chad spent the next fifteen minutes discussing the project in general, but neither of them made any real decisions about it.
Robin was amazed that he was actually managing to speak in his sissy voice, as far as she could tell, with no errors. Like it was a foreign language that he was very fluent in. But every time he opened his mouth and said anything, it was like a jolting reminder to her of just what their relationship was to each other now. She didn’t know if it was putting him in his place, but it was certainly helping to remind her of her place!
Finally she noticed the time. “Okay Sissy. Let’s go to break and clear our head of this for a while.”
Chad didn’t want to go to break if he would have to use his sissy voice there. “Um… Wobbin,” he said as he was getting out of his chair. “Do I have to use my sissy voice at bweak?”
Robin stopped to consider that. It was something she hadn’t thought of. The games were all well and good here where they were alone, but what kind of questions would the other women start to ask about her? She didn’t care about him anymore, the problem was that she didn’t want her friends to think anything worse about herself. “No,” she finally decided, use your other voice, your girly voice when were with anyone else.”
Chad was very relieved!

Mel finished up with her last client of the afternoon and walked back into her office. She still had a ton of work to do before she could go home, but thankfully, there were no more people coming in to see her. When she got back to her desk, she found a note to call Sandy. She immediately got worried that for some reason Sandy wouldn’t be able to watch Sissy while she was out on her date with Ray tonight. She picked up her phone and returned Sandy’s call right away. “Hi Sandy. It’s Mel.”
“Oh hey Mel. Thanks for calling me back. I just wanted to make sure we were still watching Sissy for you tonight.”
“If you can. I’m really counting on your help tonight.”
“No problem. We’re all looking forward to it.”
Mel felt very relieved. “Hey Sandy, Sissy had a few questions that I probably should have checked with you earlier about. He wants to know if he should bring any of the food or supplies he needs to cook with. He’s very worried about that.”
“I don’t think so, but let me call and find out for sure. I’ll call you right back?”
“That will be fine. I’ll be here.” Ten minutes later, Mel’s phone rang again and she saw it was Sandy. “Hi Sandy.”
“Hey Mel. You can tell Sissy not to worry about anything. Nothing fancy tonight at all. They just want some hamburgers and they already have everything needed.”
“I suspect that Sissy is going to be very disappointed.”
“Well, our friends aren’t exactly the fancy dining type. But hey, Mel, while I’ve got you on the phone, do you have time to kind of fill me in on what I need to know about Sissy for tonight? What do I have to do with him? What things should I watch for? You know?”
Mel smiled and leaned back in her chair. “Yeah, I know exactly what you want to know. And I’ve got plenty of time right now. So the first thing you need to do for me is…”

As soon as work was over, Chad hurried out of the building. He was already trying to put the odd day at work out of his mind. He wasn’t altogether comfortable using his sissy voice with Robin, but it was looking like he wasn’t going to have much of a choice in the matter. What if someone came around and heard him? Robin didn’t seem to care about that though at all.
They had met to discuss the project one more time that afternoon and every time he tried to say, “I’ll do this,” or “why don’t I do that,” Robin killed it immediately and reminded him that he wasn’t to do anything that she didn’t tell him to do. So he had stopped making suggestions altogether. So far, his tasks on the project were nothing but busy work that took no brain power at all. Hopefully she would assign him something a bit more interesting to do tomorrow.
But now he was looking forward to tonight. He was supposed to cook dinner for Sandy and her friends, but he still didn’t have a clue as to what he should cook. He was disappointed that Mel hadn’t let him know anything about his questions during the day. Maybe she hadn’t been able to reach Sandy. Maybe Mel just forgot!
As soon as he got home, he changed out of his messy diaper and took another shower to get thoroughly cleaned up. But then the question came. Since he was going to be with Sandy tonight, did he need to wear only one diaper again, or could he go with more? Undecided, he put just one single diaper on because he could always add more on top of it. Then called Mel. “Hewwo Mistwess.”
“Sissy! I’m on my way home right now. I should be there in a few minutes.”
Chad was a bit surprised to hear that she was early. “Mistress,” he began in his sissy voice, “should I wear only one diaper again, or should I just get ready to go with Sandy instead?”
“One diaper! And tell me as soon as you get it on.”
“I just put it on now,” Chad replied.
“Good. Just wear that, your bra, and your pink heels and nothing else. Then go over to my place. I’ll be right there.”
Chad was suddenly holding a dead phone. Just the one diaper! Ugh! And of course his bra and pink heels. Was she going to make him keep to his usual hour and forty-five minute deadline? He hoped not. And what time was he supposed to go with Sandy anyway? If he was going to cook dinner, then it had to be very soon.
As he finished up in his bathroom, his mind was already back on what he should cook for Sandy and her friends. Two minutes later, clad in only his one diaper with his bra holding up his glued on breasts and his feet adorned in his pink high heel shoes, he grabbed his purse and diaper bag and cautiously opened his door. Down below, he saw Mel just pulling into her parking space. Leaving his door open, he waited further back in his apartment so he wouldn’t be so noticeable to anyone else till she could get up the steps.
Mel hurried up toward her apartment. When she got to Chad’s apartment, she noticed that his door was open. She looked inside and saw him waiting there. “Let’s go,” she said. “I’ve got a lot to do tonight.” Then she hurried on toward her own door.
Chad hurried out and followed Mel to her apartment, following her directly inside. Mel carelessly dropped her purse on the little table by the door as she hurried past it heading for the bathroom. Chad closed the door and set his purse and diaper bag under the table. Then he had to wait till Mel came out of the bathroom. That was one good thing about wearing diapers all the time, he never had to worry about getting to the bathroom. He smiled, plus, it was a lot of fun – even after all this time.
As soon as Mel came out again, he dropped a curtsey for her. “Mistress,” he asked in his sissy voice, “what about dinner? What am I going to need?”
Mel smiled. “Don’t worry about it. Evidently they just want you to cook some hamburgers and they already have everything.”
“Hamburgers? That’s it?” Chad was shocked. Why even bother?
Mel paused before she answered. Something struck her as wrong. And then it hit her, he didn’t curtsey before he spoke again. Instead of answering, she rushed away from him searching for her stick, which she quickly found.
Chad saw her grab her stick and realized he had messed up – again! It was just too difficult to remember to curtsey before every little sound came out of his mouth. A second later, he was getting assaulted by Mel’s stick.
“What’s it going to take to teach you?” she asked as she flailed away at him – mostly at the bare skin just below his diaper.
Amid the few quick blows he had already gotten, Chad dropped a curtsey for her and apologized. Mel backed off. She wasn’t going to hit him much anyway. “Now,” she said, “to answer your question, that’s all Sandy said they wanted. Now go grab yourself another baby bottle quickly and get up on your perch. I’ve got a ton of things to do tonight and very little time to get ready. Sandy’s going to be here in half an hour.”
But if he had only half an hour… This time he didn’t forget to curtsey. “But Mistress, do I still have to worry about my leaking deadline?”
Mel looked shocked. “Of course! I’ve already talked to Sandy about it.” She glanced at the clock, “and you’ve got an hour and a half to go. Sandy promised to make sure you leak on time all night.”
Chad stared in disbelief. All night? And in front of her friends? His mind was whirling as he pulled a bottle out of the refrigerator and carried it over to his corner. Putting the bottle to his mouth, he carefully climbed up onto his perch which pushed him firmly into the corner. Stuck! Stuck in his corner again! With nothing to see but the corner of the ceiling – and his bottle as he drank it. With no other stimulation, he tried to imagine what was ahead of him tonight, and couldn’t. Just hamburgers? Why bother?

Robin walked almost wearily through the gym door. The place held no attraction for her tonight. But then, before she knew so much about Chad, she had an ulterior motive for coming. Of course she did need the exercise, she really did! But now, there was no fun, no interest in it to her at all. She would quit, but she had spent so much money on it that her husband would never forgive her if she did. So like it or not, quitting wasn’t an option.
And she really did need to lose a few pounds. She wondered how Sissy had really managed to lose so much weight so quickly. She made a mental note to wring it out of him tomorrow. The idiot!
She went into the locker room and changed clothes, exchanging greetings with a few of the other members she was beginning to recognize now. Just that little bit of extra friendship went a long way though and brought a smile to her face for the first time that day. Maybe, in the future, she might even look forward to coming. Maybe. But she doubted it.
“Robin?”
She turned and found Darla heading her way. “Hi Darla,” she said, remembering that it was Darla who was going to tell her all about Sissy. But she knew all about Sissy now. She knew way too much!
“I’m so sorry I had to rush off last time,” Darla said in her British accent.
Somehow, Robin was fascinated just listening to it and smiled. “That’s okay, I understand. “I’ve got a husband and baby at home and I never know what can happen.”
“Exactly!” Darla replied happily. “Anyway, you were asking about the chap who shows up here in dresses at lunchtime.”
“Sissy,” Robin replied.
“Yes, I think that’s what they called him then.” She suddenly laughed. “Oh you should have seen him that day. It was a scream!”
“That day? I thought he comes here every day.”
“Oh, I guess he does, but there was one special day that was very much different. And he came earlier than usual. Before lunch.”
“Before lunch?”
Darla nodded. “Oh, it was an absolute scream, I tell you. He had on the silliest little girl style party dress. It was all blue and white with ribbons and lace and huge petticoats underneath. And underneath that…” She clapped and laughed in delight… “he was wearing… nappies! Oh! Can you imagine? And he came in and sang and danced like a delightful little girl. And when I mean little, I mean he sounded and acted like a very little girl! And we all had so much fun watching him.”
“I can imagine,” Robin replied, interested despite herself.
“Oh! It was an absolute scream!” she repeated. “And obviously, he was having a very good time performing for us. I doubt we would have enjoyed it half as much if he wasn’t so delighted doing it. Oh, it was so funny! And over and over again he kept lifting up his petticoats to show us his nappies!” She paused as if to keep control of herself. “And then, at the end, at the very end…”
“Yes?” Robin asked, wondering what more there could possibly be.
Darla shook her head at remembering it. “At the very end, his nappy, which looked for all the world like he had actually wet it – could you imagine if he really had? – It looked like it had started leaking, and they took him off somewhere to change it! What an odd finish! But then, I don’t know of a better way to accent what he was trying to portray. It was an absolute scream I tell you. So funny!”
Robin nodded. “I can imagine.” And she could also imagine that his “nappy” might really have started leaking. Wasn’t that what the idiot’s bet was about after all?
Robin went through all the motions in exercise class. She worked up a good sweat, as usual. But she barely noticed the class or how hard she was working. Her mind was too preoccupied with trying to imagine everything that Darla had just told her. And what’s more, she knew without a doubt that every word Darla had said was the truth… the absolute gospel truth. The idiot!

My Internet Is Dead!

2012-01-16T06:37:00.001-08:00

My home internet is dead!

Hopefully, this won’t make a lot of difference to any of you, but my home internet has officially died – totally! And after spending an hour and a half with Hughes Net last Friday night, they discovered a problem with my receiver dish – and they finally figured out that my modem is toast. No kidding! I tried to tell them that.

Unfortunately, the earliest they can get anyone out to repair it isn’t until next Saturday. So I’m going to “attempt” to post the story parts from my work computer. With any luck, the only real difference will be that they will get posted a few hours later than I usually post them. But since I’m not really supposed to be doing things like that from work I may have to work something else out. So don’t get concerned if you don’t see things as you usually do. I’m working on it. Like I said though, hopefully none of you will see much of a difference.

My biggest pain is that there are a few sites out there that I try to keep up with and I can’t. So I’ll have a lot of catching up to do next week.

Have some fun y’all!
Karen

The Bet - Chapter 46 (Tuesday – week 7 Part 5 of 9)

2012-01-13T03:12:00.000-08:00

The Bet
by Karen Singer

Chapter 46 (Tuesday – week 7 Part 5 of 9)

Tom Robinson took the stairs instead of the elevator. It wasn’t for exercise reasons, it was just that he was trying to delay a bit going down to talk with Chad – or was it Sissy – and Robin. He had heard the most outrageous things about Chad-Sissy yesterday. And something about pictures of Chad and Derek (of all people) out on a date together – including a picture of them kissing! He had refused to even see any of those pictures. He knew Derek fairly well, at least he thought he did, and Derek wasn’t any kind of homosexual – as far as he knew.
All too soon he reached the hallway where they were working. All too soon he arrived at Chad’s cubicle. “Chad… I mean, Sissy.”
Chad turned at the unexpected voice and was surprised to see his boss there. “Hi Tom,” he replied. “What’s happening?”
Instead of answering, Tom called over top of the wall, “Robin! Get over here so I can talk to you two together.”
Robin hurried over, wondering what Tom would want now.
Tom looked between the two of them. “Look,” he said, “I know you two haven’t been doing much of anything lately. So I’ve got good news for you. That contract we were hoping to get got approved today, so I need you two to start working on it right away. I’ll email you everything we have so far.” He looked at Chad. “I know you’re going to be away for a week on vacation, but that’s still a few weeks away, so just make sure that Robin won’t have any problems while you’re gone.”
But Robin wasn’t all that thrilled about what was going on. “You mean you want us to work together on this thing again? Like the last project?”
Tom nodded. “You got it. You’ve both got nothing much to do, and besides, it was pretty obvious from your last collaboration that you two do your best work together. Plus, the client is in kind of a hurry for this.”
Robin shook her head. “But I can handle this by myself. There’s no need to have both of us on it.”
Tom shook his head. “No, you’re both sitting around doing nothing, and I want to see input from both of you! Got it?” Tom wasn’t sure why Robin had wanted to run by herself with this one. It made no sense. He knew the two of them were friends and worked well together. “I’ll email you two the details as soon as I get back to my desk. Any questions?” Both Robin and Chad shook their heads. “Good! See you later then.”
Robin watched Tom walking back up the hallway. When he was out of earshot, she let out a small curse. “Dammit! Of all the lousy luck! Now what am I supposed to do?” She looked at Chad. “Shit!” she said. “I was really hoping to avoid having anything to do with you anymore. And now that’s all out the window. Shit! I’m not going to like this one bit! And I hope you don’t either!” Then she turned and walked out on him.
Chad stared after her. He could understand why she wanted to avoid him. Heck, the way she had been acting for the last two days, he wanted to avoid her too! And now Tom was practically throwing them together. They had no choice but to work together. As much as he was looking forward to this new project, he was also very worried about how it was going to work out between him and Robin.
Robin stared angrily at her computer screen. She was being forced to work with the damn… pervert! The idiot! Why couldn’t Tom have let her handle this one by herself? She could do it – easily! Just like all the other projects she had done. Now what was she going to do? Was it possible to do this project without seeing or talking to him? Much? Unfortunately, she knew the answer to that one was a big fat no! Ugh! She wasn’t going to enjoy this one little bit. And personally, she felt that, if she wasn’t going to enjoy it, then she really hoped that he wouldn’t enjoy it either. In fact, he didn’t deserve to enjoy it one little bit! In fact… She was reminded of the things that Mel had tried to convince her of at lunch today. She had pretty much turned Mel down flat! But now? As much as she hated to admit it, maybe she should reconsider Mel’s offer. Maybe. Ugh! She didn’t want to do this… but…
Just to test the waters – so to speak – she opened up her email program and typed an email to Mel.

Mel didn’t get Robin’s email till she finished with her next client. She was surprised to see it only because Robin had turned her down during lunch. Robin had been cordial about it, but she had simply been determined not to be drawn into the “games” between her and Sissy. But now, there was an email from Robin when she least expected it. Curious, Mel opened and read it.

Dear Mel,

Unfortunately, circumstances have arisen forcing me to work closely on a new project with Sissy. If I have to be saddled working with him, then I’m not going to enjoy it at all. And if I’m not going to enjoy it, then I don’t see any reason why he should enjoy it either! As much as I don’t like the idea of it, I may have to take you up on your offer!

Robin

Mel was astonished – to say the least! And her excitement was growing too. It was almost more than she could hope for – she thought. She knew Robin was still going to be very reluctant about everything, so she decided to play it safe with her first bit of advice. She typed her email:

Hi Robin,

I think the first thing you should do is to make it clear to Sissy that no matter what your boss thinks the situation is, you are the one who is actually in charge. Fully! Put him in his place and keep him there. If you have any misgivings about this, just remember that he’s nothing but a sissy. Take charge!

Oh, by the way, I forgot to ask you earlier if he has adequately demonstrated his sissy voice for you yet?”

As always, feel free to call or email me,
Mel

Robin got Mel’s email only seconds after Mel had sent it. For once, she was looking forward to hearing from Mel – as much as she hated to admit it. The email was shorter than she would have liked, but she read it with great interest. Take charge? Put him in his place and keep him there? Any misgivings? Misgivings? Mel had to be kidding! All Robin had to do was to remember him in his silly sissy baby dress, sitting in a highchair, and covered in baby food to wipe away any misgivings she may have. Plus there was the fact that he had pissed her off earlier today over not apologizing properly. He had tried to get away with things – like a child! Mel was right! Who should be in charge? Certainly not Sissy!
She read the part about his sissy voice. Only then did she remember that she had gotten a tiny taste of it earlier when he had finally done his apology correctly, but mostly, she had ignored and dismissed it. But… thinking about it certainly brought to mind some interesting ideas!
She noticed another email come in, but this one was from Tom. Obviously the specs for the new project. She ignored it completely and got up from her seat to go see Sissy.

Chad was just opening up the email from Tom when Robin marched back into his cubicle.
“Let’s get one thing straight,” Robin said immediately, “I’m in charge of this project, not you! You’ll do what I tell you, when I tell you, and nothing else! Got that?”
Chad’s mouth hung open in surprise. “Um… If that’s what you want,” he replied, totally unsure of Robin’s mood.
“Isn’t that what I just said I want… idiot?” Robin yelled back forcefully.
This time, Chad was a bit more startled. “Uh… yeah, sure,” he replied.
Robin shook her head. She wasn’t sure of his attitude toward her at all. She had to put him in his place and keep him there. Let him know just how serious she was – as well as just what his place would have to be around here from now on. But to go about it… She smiled. “Just so long as you understand.”
Chad nodded eagerly. “Yeah, sure, I understand. You want to be in charge of this one.”
Robin wanted to hit him, but all she did was to smile at him instead. He didn’t really get it at all. She didn’t want to be just in charge of this project. If she was going to be stuck working anywhere near him from now on, then it was going to be on her terms completely and not his! Almost sweetly she said, “Do me a favor please.”
“Sure, anything,” Chad replied, trying to stay on her good side. She was actually being nice for a change!
“Show me your little apology again.”
“Now?”
“Of course now!” Robin replied a bit more forcefully. “Didn’t I just say that’s what I wanted you to do?”
Instead of replying, Chad quickly got up from his seat and pushed his chair back to give himself more room.
“Not there,” Robin told him quickly. “Back out in the hallway again!” She almost added, “where you belong,” but she stopped herself before she could say it.
Chad didn’t like having to go back out to the hallway to do it again. What if someone happened to come by and see him? But with a little look of wariness, he went. Again he looked both ways before he began to make sure nobody was watching, then he dipped into his curtsey. He stood up again putting his feet together and clasping his hands in front of him. “I’m sorry Robin that I didn’t do exactly what you told me to do yesterday,” he said in his sissy voice. “I promise not to give you any more trouble and to do whatever you say from now on.” Then he quickly repeated his curtsey for her one more time. He wanted to move from the center of the hallway, but since she had made him do it over and over again earlier, then he was afraid to move.
Robin looked up and smiled. “That was very sweet,” she said. “Now tell me, do you mean it? Do you really mean that you won’t give me any more trouble and that you’ll do exactly what I want from now on?”
Without thinking, Chad dropped a little curtsey before he spoke. “Of course I mean it,” he replied in his girly voice.
Robin’s smile gained a touch more wickedness. “That’s good,” she said. “So that was your… sissy voice?” she asked.
Chad nodded, and started walking back toward her again. “Yes,” he confirmed.
“Stay there!” Robin ordered quickly, stopping him in his tracks and backing him up. Then she was all smiles again. “I like it,” she said. “It… suits you.” She paused as if to consider something, although she actually knew exactly what she wanted from him. Very nicely she said, “What I want from you… is for you to use your sissy voice from now on whenever you’re with me. Forget that other silly voice you use completely. What do you call it, your girly voice?” Her face grew more stern – as did her voice. “Your sissy voice not only suits you, but it will serve as a constant reminder to me of just how childish you can be sometimes! And… since you still dress like a woman all the time, it will also keep me from making the mistake of thinking that you ever really wanted to be a woman at all! Got that?”
Chad was horrified. Use his sissy voice? Here at work? He didn’t think he could!
“I asked if you got that?” Robin asked angrily.
Frightened by her sudden angry demeanor, Chad quickly replied. “Yes!”
Robin looked at him. “Was that your sissy voice, or that other voice of yours?”
“My… sissy voice,” Chad replied, wanting more than ever to get out of the middle of the hallway now.
“I’m having a little trouble telling the difference.”
“There isn’t much difference with most words. It’s just certain letters I’m not allowed to pronounce.”
“Like what?”
“Mostly ‘R’s and ‘L’s.”
Robin nodded. “I see. I think. Come back here now,” she ordered.
Chad was very relieved to get out of the middle of the hallway. He wasn’t too sure about what was suddenly going on with Robin. Yesterday she had made him suck his thumb, now she wanted him to only use his sissy voice? What was going on?
“I’m going to be watching the way you talk from now on, just so there’s no mistake. And believe me, I will be watching you, especially since you’ve already shown me that you can’t be trusted.” She shook her head, dreading the realization of what she was about to say. “I guess you can consider our little arrangement here to be kind of like the one you have between you and Mel. When you’re here with me, you do whatever I say. When you’re back with Mel, well, you get the picture. Got it?”
Chad almost curtseyed, but he caught himself just in time. “Yes,” he replied simply.
“Are you sure?”
Chad nodded, “I’m sure,” he replied, carefully using his sissy voice.
Robin noted the odd pronunciation of the word “sure.” He hadn’t used the letter “R.” She nodded satisfied. “Good! Now get back to work and look over what Tom sent us. We’ll discuss it later – if and when I’m ready!”
Robin went back to her desk to open the email from Tom to review the project, but her thoughts weren’t on the new project, they were on what had just happened between Chad and herself. How odd. It wasn’t that she was really angry. Strangely enough, she really didn’t feel the anger anymore that she had been living with for the last few days. Instead, what she was feeling was more like… justification? She wasn’t really sure. But there was this odd sense of… power that she had felt over him too.
It was kind of an alien thing to her and she wasn’t sure what to make of it. It certainly wasn’t like anything she had felt in any other relationship she had ever had with anyone. When it came to relationships between a man and a woman, she had always expected the man to take the lead. It’s how she was brought up. But then, right now, it was difficult to think of Sissy as a man. Of course he was a man. But… But was he really? Gloria had said it was like a disease, but one that couldn’t be cured. But did that make him any less of a man? Once again, the image that had haunted her mind since she had first seen him last Saturday blurred her vision – the sight of him sitting like a messy baby in his highchair. It was very, very hard to think of the person in that chair as a man. And of course, that person was… Chad.
So maybe, she could do this – if she could continue to remember that he wasn’t a man… or at least, he didn’t deserve to be called a man – anymore. Yes! That was more it! It wasn’t that he wasn’t a man – underneath… it was more that he didn’t deserve to be considered a man anymore. So, she shouldn’t treat him like one. He was a baby. Well, maybe not. He was a... child? Not that either, not really. He was a… a sissy! It was the only word she could use to describe him. And Gloria had said that he craved and actually needed humiliation. Well, with a man… or even with another person… she couldn’t do the things she was about to embark on with him. It just wasn’t right! But here she was, getting ready to actually do the very things with him that she had protested in the first place. The very things that had made her sick! The idiot!
Now that she saw him more clearly… Now that she saw the entire situation more clearly… Only now, she could actually contemplate taking that ridiculous step toward lording over him. How ridiculous it sounded to her. It wasn’t her! It wasn’t anything like she would ever do or would ever think of doing. Yet here she was, she guessed, actually doing it. And, dare she admit it? There were certain… aspects… of it that actually felt good to her. She wasn’t really sure what they were or why, but she knew that there was something deep down that was actually pleased by what she was doing. Maybe… Maybe it was because… he deserved it! And he did! The idiot! Justification! She still couldn’t fathom why he would ever enter into something like the bet he had made with Mel in the first place. He must have been desperate indeed!
So now while she still felt a bit confused by it all, she also felt a bit of a sense of power, and of course there was also a feeling of satisfaction that he would be getting just what he deserved. And she realized one more thing dangling around in her jumble of new feelings. She felt a tiny bit of fear over it too. Was it right? Could she do this? Could she really? Once again she pictured him, a total mess in his highchair. Well, she was going to give it one damn good try!

The Bet - Chapter 46 (Tuesday – week 7 Part 4 of 9)

2012-01-06T02:57:00.000-08:00

The Bet
by Karen Singer

Chapter 46 (Tuesday – week 7 Part 4 of 9)

Mel glanced around the restaurant one last time as she and Gloria sat down to lunch. But as she expected, she didn’t see any sign of Robin.
“What’s wrong?” Gloria asked.
“I had invited someone else to join us today. I was just checking to see if she actually might have come.”
“Who?”
“Robin. But don’t worry, she said she wasn’t coming.”
“Wait a minute! Is this about that big mistake you mentioned yesterday that you wanted to talk to me about?”
Mel nodded, “Yeah. I really messed up.”
Gloria sighed. “Okay, out with it! Let’s get this over with so I can find out about your date instead! So I take it this concerns Robin?”
Mel nodded. “Yeah. I just wanted to meet her!” Mel explained before she said anything else.
“And what on earth did you do to her?”
Mel looked sheepish. “I told her everything about the bet. And then I took her over to see Chad at Sandy’s where she had him totally babyfied – and then some!”
“And?”
“She didn’t take it too well.”
“I’m not the least surprised. What happened?”
“She got really mad.”
“I have no doubt. And?”
“And… We were really concerned that she would blab too much to the wrong person and Chad would lose his job.”
“And did she?”
Mel shook her head. “Not yet. But she still seems to be awfully mad.”
“And you wanted to talk to her today to try to calm her down a bit. So you invited her here to lunch but she refused.”
Mel nodded. “Something like that.”
“Anything else I should know?”
Mel shook her head.
“So I take it that things aren’t as bad as you thought they were?”
“So far. In fact, I’m wondering if things are better than I thought.”
“So there’s no problem?”
“That’s just it, I’m not really sure. That’s another reason why I wanted to talk to her today.”
Gloria wasn’t really interested in talking about Robin, she was more interested in hearing the details of Mel’s date. She leaned forward, “So let’s forget Robin. Tell me about Ray!”

Robin drove around trying to figure out what she really wanted to do. She had told Mel that she wouldn’t meet her for lunch, but now she was reconsidering that. Should she talk to the crazy woman? She didn’t want to, but she still had some questions… no, to be fair, she really just wanted another chance to give the woman a piece of her mind! But should she? The restaurant Mel had mentioned was up ahead, and since she was already there, she turned into the parking lot, wondering if she should really do this or not.

“Right there in the movie theatre?” Gloria asked incredulously.
“Right there!” Mel confirmed. “Believe it or not!”
Gloria shook her head. “Oh God! If it would only happen to me!” She leaned forward, anxious for more details. “What did you do?”
Smugly, Mel leaned back in her seat. “What else? I reached over and put my hand right on his…” She stopped, startled because out of the corner of her eye she caught sight of Robin in the restaurant, standing near the front and looking for her. “I don’t believe it,” Mel said. “She’s here!”
“Who?” Gloria asked, frustrated that the story had been interrupted.
Mel stood up and waved her hand in Robin’s direction. “Robin,” she called out without trying to be too disrupting to the other customers.
Gloria looked and saw a woman walking towards them, obviously Robin. She wasn’t very happy – and neither was Robin from the looks of things. “You’re going to owe me big for this one,” she muttered.
Robin walked up to the table and eyed the stranger uncertainly. “I’m sorry,” she said, “I didn’t know you would have another guest today.” It was only because of Gloria’s presence that Robin hadn’t already started giving Mel another mouthful.
“Robin, this is Gloria,” Mel introduced. “Gloria, this is Robin.” Then she sat down. But Robin remained standing.
“I’m sorry,” Robin said again. “I should leave.” She started to turn away, but Mel stopped her.
“You’re here. The least you can do is let me buy you some lunch. I owe you that much at least.”
Robin bit back the remark she really wanted to make. As far as she was concerned, Mel owed her a lot more than that. “I don’t know,” she said with a glance at Gloria. “There are things I was going to talk about that aren’t for…” She glanced in Gloria’s direction again.
“Are you talking about Chad?”
Robin nodded.
“It’s okay. Gloria here knows everything about it.”
“And then some,” Gloria muttered half to herself.
Robin stared suspiciously at Gloria, still unsure.
“Sit down,” Mel told her. “You’re here. Let’s talk.”
Robin finally pulled out a chair and sat down, but her stare didn’t leave Gloria. “Are you another one of those… dominant type women who goes around with a whip in your hand?”
Gloria’s eyes bulged and before she knew it, she let out a big laugh. “No! I’m a therapist. I specialize in relaxation therapy.”
“A therapist?” Robin repeated. Then she looked angrily over at Mel. “She’s the one who needs therapy, but not the relaxation kind.”
Gloria laughed again. “I couldn’t agree with you more! But to be honest, since this whole bet thing started, what I really think is that both Mel and Chad really need is someone to knock their heads together and pound some sense into them!”
Robin was totally surprised to hear Gloria say that. “You mean that?”
“Totally!” she replied with a cautious look straight at Mel. She saw Mel smirking back at her.
It took a moment for Robin to take that in. Here was someone who was on her side! “So I’m not wrong in the way I think?” Robin asked.
“Not at all!”
“Then why don’t you do something about it?”
“Like what?” Gloria asked.
“Like stop them! It’s madness!”
“Yes, it is. But it’s a lot more complicated than that.”
Robin momentarily buried her head in her hands. Complicated! “Chad used to tell me that it was complicated, and I didn’t believe him. Now I find out that it really is incredibly complicated. I don’t think I can take any more!”
“I know what you mean,” Gloria replied. “Unfortunately, it goes with the territory.”
Ignoring Mel completely, Robin said, “Look, I just want to know why they’re doing it in the first place. It’s stupid!”
With a glance at Mel, Gloria replied. “That it is. But like I said, it’s complicated.” She paused to figure out where to start, but just then the waiter came back with Mel and Gloria’s drinks.
“And what would you like?” the waiter asked Robin. Robin hadn’t even seen a menu. She wasn’t really sure she wanted to eat.
“It’s my treat, so order whatever you want,” Mel told her.
Taking a stab at something she liked, she asked, “Do you have chicken fingers and fries?”
“Of course,” the waiter replied as he wrote it down on his pad. “And to drink?”
“Just tea,” Robin told him.
The waiter finally left and Robin looked back to Gloria, once again ignoring Mel. “So what’s the answer?”
Gloria stared at her for a moment before replying. “Unfortunately, what they’re doing ‘is’ an answer. Maybe not the best one, but it is an answer.”
Robin was puzzled by that. “What do you mean?”
Gloria took a sip of her drink before replying, trying to give herself a bit of time to collect her thoughts. “Most people wouldn’t think of doing what they’re doing,” she started.
“You can say that again!” Robin agreed.
“But then, you and I are most people. They’re not – especially Chad.”
“Chad?”
Gloria nodded. “Most of the parts you don’t like really boil down to him and his individual needs.”
“His… needs? He needs to have his head examined!”
Gloria smiled. “Maybe, but the truth is, it wouldn’t do any good. Those needs in him are awfully powerful. He can try to suppress them, but in the end, they’re going to find a way to come out, no matter what he does.”
“Wait a minute,” Robin interjected. “What needs?”
“They’re actually based on sex, but as I said earlier, it’s a lot more complicated than that. In his case, he has somehow gotten his brain confused between normal sex, and humiliation – in his case, specifically transgenderism and infantilism.”
“You know you’re on the verge of losing me,” Robin replied.
Gloria nodded. “I’m sure. Let’s just say that Chad craves humiliation. He has to have it. It’s like a drug. Eventually, he’ll do anything to get it. And the diapers and dresses and stuff are his ways of attaining that humiliation.”
Robin shook her head. “You have no idea how sick that sounds!”
“Oh yes I do! But that’s the way it is. This bet works out well for Chad because it fulfills all his wildest fantasies.”
Robin jerked her head towards Mel. “And what about her?”
Gloria smiled. “Mel? Well, let’s just say that she’s not without a few needs of her own.”
Robin tried to digest that. “So what am I supposed to do about it?”
Gloria looked at her with surprise. “Nothing.”
“Nothing? How can I do nothing? I have to work with the guy!”
“So?”
“So I’m just supposed to pretend that I never heard any of this stuff in the first place?”
“You can try if you want. But what you do is really up to you. And you don’t have to do anything.”
“Up to me?” She shook her head. “Maybe I don’t have to do anything, but that doesn’t mean I have to like any of this!”
Gloria leaned forward. “That’s the best part. You don’t have to.”
“I don’t?”
Gloria shook her head. “I don’t like it either.”
Now it was Robin’s turn to shake her head. “So what do I do? It’s driving me crazy! You have no idea how angry I am at him for doing something so… idiotic!”
Gloria shrugged. “Like I said, deal with it any way you want. Whatever makes you feel the best. But just keep in mind that Chad’s problem is not going to go away. It’s like a disease he has to live with it for the rest of his life.”
Mel finally leaned forward, she had been sitting back somewhat amused by the fact that Robin had ignored her completely. But now… “If you’re looking for ideas about what to do about it, then maybe I can help.”

Chad had gotten back a bit early from lunch, but now it was past time for everyone to be back to work, except he was fairly sure that Robin wasn’t back yet. Or was she? He never once heard any sound coming from the other side of the wall between them. Since he thought she wasn’t there, he chanced getting up and checking to see, hoping that if she was there that she wouldn’t get too mad at him for disturbing her. But fortunately she wasn’t back yet. Or unfortunately. Now he was worried that she may have had an accident or something.
He went back to his desk still worried about her. Since she wasn’t there, he chanced opening up the spreadsheet he kept for keeping track of his bet progress – or lack thereof as was usually the case. Seventeen more days to go before the testing would start. It seemed like an eternity. No, it was an eternity. Sort of. He found yesterdays date so he could fill in the amount of time that he remembered being able to hold back. Five minutes. Just five little minutes. Five lousy minutes. How had he lost so much? And how had he lost so much over the weekend? Well, to be honest, yesterday hadn’t been the best of days and mostly he had been too worried about Robin and what she might do so he really couldn’t try very hard. Even though he only filled in five minutes for yesterday, he was confident that he could do a lot better today. He had to!
He closed the spreadsheet quickly before Robin could see it – if she ever got back. Where was she?

Robin knew she was running late, very late. And she cared, but not all that much. She simply had too many weird things rattling around in her head. She also was trying to figure out what had just happened during lunch. She had gone there to get some answers. No, that wasn’t really right. She had told herself she was going just to get answers, but in her mind she had only seen herself yelling and venting her rage at Mel. But that hadn’t happened! Instead, she had sat and talked, calmly, mostly with Gloria – and then finally with Mel. But the things that Mel was suggesting… It was too strange to contemplate. And in the end she had been forced to turn Mel down flatly! Before lunch, she had felt angry. The same anger she had carried for days. But now? Now she was just confused.
With her head practically spinning, she entered the building again, not bothering in the least to even try hurrying. Who would care if she was late anyway? For that matter, who would even know? Well, there was Chad, but she didn’t count him – anymore.
As she approached his cubicle, her steps faltered, but only momentarily. The guy was sick! Literally! And there was nothing that could be done about it. Purposely, she strode right past him and went to her desk. She had too many weird things to think about right now before he could even think about dealing with him.
“Robin?” Chad called as soon as he realized that she had just gone past his cubicle. But he got no answer. He got up to go see her, worried that the reason she was late was because something might be wrong. He found her at her desk. “Robin?” he said again.
“Go away!” Robin replied, but while she wanted her words to sound angry, they didn’t have the same force behind them as everything she had said to him earlier.
“I was just worried about you,” Chad explained. “Is everything all right?”
Robin looked up at him. “Everything all right? No! It’s not alright! ‘You’re’ not alright!” She looked away from him. “And I don’t know what to do about it.”
Rather than temp fate, Chad went back to his cubicle. At least she didn’t yell at him – so bad. He turned to his computer to get some work done, but before he barely got started, she was back in his cubicle again.
“Sissy…”
Chad turned quickly toward her, afraid that he had somehow angered her again.
“…or Chad.” She stared at him for a moment. “No, it has to be Sissy. Especially when you’re dressed like that.”
Chad suddenly felt a bit embarrassed. But at least she wasn’t yelling – that he could tell anyway.
“Look,” she said, “I know you’re sick. Or you’ve got these… perversions… and you can’t do anything about it.”
Sick? Perversions? But unfortunately, Chad knew all too well what she was talking about.
“Personally, I think you need a doctor or something, but I understand now that even a doctor can’t help you.”
That much Chad knew to be true. Not that he even wanted help to be normal. He cherished his “perversions” all too much.
“And my problem is that I can’t deal with it! I don’t like it! I think it’s sick! And… And I just don’t think I want to be around you!”
Chad was disappointed, but he was forced to understand things from her point of view.
“So what I want,” she continued, “is for you and I to have as little to do with each other as possible. Like hopefully no contact at all! Because otherwise, just looking at you makes me so angry I could scream!” And with that, she walked out.
Chad stared at the empty space where she had been standing. No contact at all? Or as little as possible anyway. He wasn’t even sure how possible that was. But he supposed he would have no choice other than to try. He turned back towards his computer feeling like he had just lost something major in his life. He opened his email program and started typing a message for Mel, updating her on the latest. At least he wasn’t going to get fired! So far.

A Little Vacation

2012-01-05T09:24:00.000-08:00

Hi All,

I just wanted to warn you that my wife and I will be away for a bit next week. We have booked ourselves a nice little cabin up in the Georgia mountains to celebrate our anniversary.

Tomorrow’s post should happen on time (I hope, my computer is dying). Tuesday there will definitely be none. And the following Friday – flip a coin. After that, we should be back to normal again (although I’d much rather stay up in the mountains).

Do something nice for yourself while I’m gone,
Karen

The Bet - Chapter 46 (Tuesday – week 7 Part 3 of 9)

2012-01-03T02:53:00.000-08:00

The Bet
by Karen Singer

Chapter 46 (Tuesday – week 7 Part 3 of 9)

Gloria’s phone rang while she was waiting for her next patient. “Hello?”
“Hi Gloria,” Mel said cheerfully.
“Hey Mel. How is everything going? Lunch today?”
“Definitely!” Mel replied.
“Good, because I still want to hear all about your date!”
Mel laughed, “Somehow, I knew you would! See you later?”
“I’ll be there,” Gloria confirmed.

Mel hung up the phone with a smile. And that was when she noticed the email that had come in from Robin. She opened it and read it… and smiled. Amazing! But how to respond? An idea occurred to her, but… did she dare? She finally decided there was only one way to find out. She typed her reply: “Why don’t you meet me for lunch today so we can talk.” Then she gave Robin the restaurant, time, and where she and Gloria usually sat. If Robin actually showed up, she wasn’t too sure how Gloria would like it, but that was a small price to pay.

Robin read Mel’s reply. Lunch? She had to be kidding! Her reply was typed and sent very quickly. “No way!”
She glanced at the clock, then back at Sissy again. He had been doing his little apology continuously for about fifteen minutes now and she was sick of it – and him. “Sissy!” she turned toward him, stopping him in mid-curtsey. “Enough! Get out of my sight now before I find something else to make you sorry!” She watched as Chad hurried rather contritely toward his desk. The idiot! Mel wanted her to meet for lunch? Ridiculous!

Chad lugged his diaper bag toward the gym door. He was still a bit tired after all the exercise he had gotten that morning – curtseying so much. But today he was more interested than usual in having Cassie change his diapers – that is, if that receptionist Cindy wasn’t going to be in there with him again. She wasn’t yesterday, and by the way things had gone yesterday, he didn’t get the feeling she would be today. Maybe, never again! That would certainly be good.
He was mostly interested today because last night he had managed to orgasm from the anal play with Mel. And Cassie always played with him when it was just the two of them. Would he be able to orgasm today? He really hoped so. And now he couldn’t wait to find out.
Once again, he opened the door to see both Cassie and the receptionist Cindy already up front waiting for him. Yes! Yes! Yes!
Cassie turned toward Cindy the moment Chad walked through the door. “He’s all yours today. Just remember what I told you to make sure you do.”
Excitedly, Cindy replied, “Don’t worry. I will.”
Chad glanced back and forth between the two of them trying to figure out what was going on. He’s all yours? That didn’t sound good at all. He was especially worried when Cassie stayed at the front desk and it was Cindy who came out from behind it.
“Hi Sissy,” Cindy said with a mixture of excitement and taunting. Then she stood there and stared at him expectantly.
Chad again glanced back and forth between them. Then, again bowing to the inevitable, he dropped a curtsey and greeted first Cassie, then Cindy.
Cindy giggled. “You’re soooo sweet! Come along now, I’ll be taking care of you today.”
Wide eyed, all Chad could do was to stare at Cassie in horror as he followed Cindy back through the gym full of exercising women, some of whom said hello to him as he walked past. Still in shock, he followed her all the way back to the little room where Cassie changed him every day. Except this time it wasn’t Cassie!
Cindy appeared to be all business as she closed the blinds on the little window in the door and took his diaper bag from him. Chad just stood there and watched as she opened his bag and started pulling out the things she would need. “Aren’t you going to get undressed?” she asked. “I can’t change you with your clothes still on.” Almost in a fog, Chad started removing all his clothes. When he was down to just his two diapers and plastic panties, Cindy handed him his bottle and he laid down on the floor so she could change him.
As Chad drank his bottle, he noticed that Cindy seemed to be going out of her way to act like she knew what she was doing. In one way, she seemed to be all business as she pulled his plastic panties off of him and untapped his diapers, but the look on her face reminded him of a child playing a game – which, he supposed, was probably exactly what was going on.
Carefully, Cindy untapped each layer of diapers and pulled them back, being extra careful as she pulled away the last layer. Chad figured that Cassie must have told her that sometimes he started peeing at the least opportune moments. The memory of which embarrassed him – and excited him too. With the diapers out of the way, still acting business like, Cindy started wiping off his front side, being careful around his chastity device, as if it were some kind of physical injury to his body.
When she was done, she picked up the baby lotion – and stopped. With a broad grin on her face, she set the lotion down again and leaned over closer so she could inspect his device further. She reached out and grabbed the lock, wiggling it around a bit. “Does that hurt?” she asked.
Chad shook his head. “No,” he replied with the nipple to his bottle still between his teeth.
Cindy grew bolder. She reached out and grabbed the hard plastic of the device that encased his shriveled penis. She wiggled it back and forth a few times. “How about that?” she asked.
Chad didn’t know if she was serious or just playing. “No,” he said once again. He really wished she would just get on with it and finish diapering him.
Cindy wrapped her hand around the device as best she could and squeezed, but it was solid and she knew immediately that she wasn’t accomplishing anything. She tugged on it a bit, then leaned in close to try to see the teeth inside of it a bit better, then she tugged again, watching as the teeth seemed to bite into his delicate flesh. “How about that?” she asked.
“Yes!” Chad replied. “Please don’t pull any harder.”
Cindy’s only reply was to giggle. She pulled the device up a bit and grabbed his naked balls instead. She marveled at how strange they felt, like two little nuts inside of a soft leather bag. Maybe that’s why she had heard them referred to as “nuts” before. She squeezed a bit and watched his face. She saw his eyes go wide with concern. She squeezed harder and his eyes went wider. She squeezed a bit more…
“Please!” Chad cried in alarm. “That hurts!”
But as Cindy let go of him, her only reply was another little giggle. She went back to playing with his chastity device and flicked her finger against the hard plastic over top of where he penis was, as if she was trying to flick it against his bare penis instead. It made kind of a soft tinking sound as she did it. “Did that hurt?” she asked.
Chad just shook his head. What on earth was she doing?
Cindy flicked her finger again, but she didn’t have to ask to know that it didn’t hurt him at all.
She searched the top of the desk and found a pair of scissors and grabbed them. Chad grew concerned at the sight of something like that being brought so close to such a sensitive part of his body. But Cindy didn’t open the scissors. Grabbing them by the closed blades, she used them to tap on his plastic chastity instead. “How about that?” she asked. “Does it hurt when I do it with the scissors?”
Chad could certainly feel the added pressure as she tapped, but it wasn’t really hurting him. He shook his head without bothering to remove the bottle from his mouth.
Cindy tapped harder, the sound now making a much more distinct sound. She looked up at him. She could see the concern in his face, but she knew she wasn’t hurting him. Which was good! She didn’t want to hurt him. She just didn’t know a lot about men and getting the chance to play with this one – with his male parts all encased like they were, was just too much of a temptation. Besides, if she hurt him, then Cassie wouldn’t let her change him anymore. But for now, she could still play.
Since she wasn’t hurting him, she began teasing him by rhythmically tapping on it over and over again as if she were playing a song with the tapping. She didn’t tap really hard, but it was still hard enough for him to feel his device being driven down with each stroke, pulling on it at the base over and over again – and unfortunately causing the little teeth inside of it to dig in momentarily each time. The vibrations also stimulated him just a bit while at the same time, the tapping set his teeth on edge. With the extra stimulation, he could suddenly feel the teeth in his device irritating him more and more. “Stop!” he suddenly cried as he pushed her away with one hand.
Cindy looked surprised. “Was that hurting you?”
“Yes!” Chad complained angrily. It wasn’t really hurting – yet, but if she continued then he had no doubt that it would be.
Cindy was surprised and also a bit fearful. She hadn’t wanted to really hurt him, she was just… playing. She threw the scissors back onto the desk and picked up the bottle of lotion instead and began spreading that wherever she could. Chad was just grateful that she was finally getting on with it again. What the heck had she been doing anyway?
Cindy finished with his front side and ordered him to roll over. Chad put his bottle down and did as she said. He missed Cassie here. He had been really looking forward to Cassie playing with him again. He could feel Cindy wiping him off and then spreading the lotion all around, but it was absolutely nothing at all like the way Cassie did it.
Cindy finished with the lotion and wiped her hands off. Then she reached for the jar of suppositories. “According to Cassie,” she said as she opened the lid, “these are the most important thing we’re doing here.”
Chad disagreed completely.
She pulled one of them out of the jar and looked at it. “I just wish putting this thing into you wasn’t such a gross process!
“Don’t do it,” Chad suggested – ever so casually.
Cindy shook her head. “I have to. I promised Cassie.”
“But you don’t really have to. Cassie will never know – and I promise I won’t tell her!”
Cindy shook her head again. “Cassie said you would probably try to talk me out of it!” With that, she took the pill, placed it up against his tiny hole, and started pushing it in with her finger. Since she hadn’t lubed him in there the way Cassie did, not to mention she hadn’t stretched him out a bit first, the pill was hard to push in at first and Chad could easily feel the resistance. But her perseverance won out and it didn’t take long till he felt her entire finger invading him as far as it would go. Ugh! He hated those stupid pills! But as she got the pill all the way in, Chad felt something else too. He suddenly felt the urge to pee again. As he had tried to do all morning, he clamped down hard as soon as Cindy removed her finger and did his best to hold back against peeing. He couldn’t check his watch but that didn’t matter. What mattered was that he tried his best to hold it.
Cindy had him roll over again and she quickly swapped out his soaking wet diapers for fresh dry ones. She wasn’t as fast as Cassie was though and before she finished, Chad was really struggling to hold back. He didn’t want to embarrass himself any further by having an accident in front of Cindy, so he persevered and prayed she would get his diapers fastened up soon.
Cindy had no idea of the struggles Chad was going through, but she was all business again as she did her best to pull the first diaper up tight and tape it in place properly. But as she was pulling the second one up, she realized that the first diaper she had just taped in place looked a bit different – or was it just her imagination. She stared closer to see if she had made a mistake, and she noticed it changing some more. Surprised, she looked up at him. “You’re…”
“Yes!” Chad replied before she could get the word peeing out of her mouth. He was embarrassed that it had happened in front of her, but at least he had managed to hold on long enough for her to get the first diaper securely taped in place. A few seconds sooner and it would have been much more embarrassing!

The Bet - Chapter 46 (Tuesday – week 7 Part 2 of 9)

2011-12-30T02:58:00.000-08:00

The Bet
by Karen Singer

Chapter 46 (Tuesday – week 7 Part 2 of 9)

Robin stared at her computer screen, but her mind was more on the apology that Chad had just given her and on the email that Mel had sent. So that was Mel’s idea of a proper apology? Well, she guessed it was a lot better than some. Not that she really cared. Should she answer the crazy woman like she wanted and tell her that she had received Sissy’s apology? Against her better judgment, she opened the email and hit the return button and typed: “Yes, he apologized.” Then she sent the email. Hopefully, she could put both her and Sissy out of her mind for a while.

Mel saw Robin’s email as soon as she got to work. She was glad that Sissy had actually apologized, but Robin certainly wasn’t very forthcoming with the details. She closed the email and opened up the one from Sissy. From what she read in Chad’s email, it sounded like Robin was still pretty angry – which made sense when compared with the email she had just gotten from Robin. So… now it was time to check on a few things. She opened Robin’s email again and typed a short reply.

Robin still had one or two little things left to do on her list from Tom Robinson, but it really amounted to nothing much. She could do it all in less than an hour, if she wanted to. But she was distracted from finishing any of it by another email from Mel. As much as she didn’t want to open it, because she really didn’t care what the woman wanted, she also couldn’t not open it.

Dear Robin,

I’m very glad he apologized, but I’m worried that he didn’t do it exactly the way that I wanted him to. Before his apology and also after it, he was supposed to give you a very nice curtsey, pulling his skirt as wide as possible in the process. I made sure he was wearing a very full skirt today so that his curtsey could be at its “sissy best.” Please let me know if he did this.

As always, feel free to call or email me,

Mel

Sissy best? That concept floored her. Yes, she knew the guy was a sissy, but it’s just that the label had never struck her that much. In the past, before she knew better, she had thought of him more as one of those cross-dresser types. In fact, since he had been dressing totally as a woman for so long now, she had started to believe that eventually he would be getting a sex change – no matter how much he denied it. But a sissy? That label brought to mind a whole new level of concepts – and the realization that she knew less about someone who was a sissy than she did about someone who was a cross-dresser – which wasn’t very much. But… was “sissy” an accurate label for Sissy?
Not knowing, and also not sure she wanted to know, she went back and reread the details of Mel’s little email. He was supposed to curtsey before and after – well, that much he had done. And the more she thought about the fact that he had curtseyed, the more she liked the term sissy for him. A woman apologizing to another woman wouldn’t curtsey in the process. In fact, there were very few reasons why a woman now-days would curtsey at all. She herself had rarely done it in her entire life! She barely knew how! So now the term sissy was starting to take on a whole new meaning for her.
And he was supposed to pull his skirt as wide as possible? Well, that much he certainly hadn’t done! She had been surprised that he had curtseyed in the first place. Although when he had done it, she had pretty much dismissed it, waiting to hear what he had to say instead.
So, bottom line, he had apologized, but not the way he was supposed to. She wondered what else he might have left out. Not that it mattered. She always believed that an apology should come from the heart for it to mean anything. So obviously, this was contrived and as an apology it didn’t amount to a hill of beans! Not that she really cared all that much. She was still pretty much angry and disgusted with the jerk and she still wasn’t all that sure how, or if, she should talk to him again. The idiot!
After quickly reading Mel’s email one last time, she was reminded of her problem with him yesterday where he hadn’t done as he was told. Okay, she was overly upset and sensitive yesterday, she guessed she still was somewhat. But at least she wasn’t as bad today – she thought. But still, the point was that obviously, when left on his own, he couldn’t be trusted to follow through with what he was supposed to do! Just like a child! But then he wanted to be a child – well, he wanted to be a baby. But that was still a child! Was he now acting more and more like one? She shook her head in disgust and typed a short reply to Mel. “He curtseyed, but not at all like that. What else was he supposed to do – or say?”

It was a while before Mel had time to check her email again. She wasn’t sure if she was surprised or not that Chad hadn’t apologized like she wanted him to. In fact, she had mostly expected that he wouldn’t. But the part that she was really interested in was that Robin had replied again – and asked for details! That alone meant a lot!
But how should she proceed? For once, she didn’t want to frighten Robin off, so she knew she still had to be careful. Very cautiously, she typed her reply to Robin. Again, it was short and simple, only telling her the text of what he was supposed to say. But just before she sent it, as an afterthought, she added one extra little tidbit.

It was almost break-time when Robin got the reply from Mel. Again, she was tempted to not open it, but like before, she was too curious as to what was in the email.

Dear Robin,

Thank you so much for replying to me. Here’s what was supposed to happen:

He was supposed to give you a very nice curtsey, pulling his skirt as wide as possible while bowing his head in respect to you. Then he was supposed to stand up straight with his feet together and his hands clasped nicely in front as he said: I’m sorry Robin that I didn’t do exactly what you told me to do yesterday. I promise not to give you any more trouble and to do whatever you say from now on. Then he was supposed to repeat the same curtsey he had given you at the start.

I was hoping that this simple but sincere little routine would be acceptable to you and would also get the point across to him that he needs to follow your direction just as if it were me.

Oh, one other thing. Did you know that his “girly voice” is not the way that I want him to talk? Even this apology was supposed to be given in his “sissy voice.”

As always, feel free to call or email me,
Mel

Robin must have read the email at least three times. Nothing that Sissy had done was like Mel had wanted it to be. For someone who was supposed to be his… mistress – what a laugh – obviously Mel wasn’t all that good at controlling him. She knew without a doubt that she shouldn’t really care, but it still irked her that Sissy was supposed to give a “better” apology to her than he did – even if it was contrived by someone else. But what should she do about it? In fact why should she do anything about it? There was no way she was going to get drawn into that crazy woman’s games! Still, it irked her. And what the heck did she mean by his “sissy voice?”
She glanced at the clock. Break time. With a bit of a huff, she closed the email and left her cubicle. She stopped at the entrance to Chad’s cubicle. “Sissy, it’s break time!”
Chad looked up in surprise. Was she speaking to him again? He quickly got up from his seat and followed her out into the hallway. “Robin,” he started to say, but he got no further than that as she quickly turned on him and forcibly backed him up against the wall.
“What do I have to do,” she said forcibly, “make you go to break with your thumb in your mouth too? What’s it going to take for you to understand that I don’t want to talk to you yet?”
Chad was too shocked to do more than stare at her wide-eyed. One thing he had learned about her in the last two days was that she seemed to get awfully physical when she was really angry. Silently, he followed along behind her to the break room.
The act of walking seemed to stimulate Robin’s thoughts – which immediately returned to Sissy and Mel’s email. Why should she care? She didn’t! She absolutely didn’t. But she couldn’t stop brooding about it. Sissy should have given her a better apology than he did. He was supposed to… and… she deserved something better! And what the heck was his “sissy voice?”
In the break room, she headed straight for the coffee pot and poured herself a cup, never glancing once back in Sissy’s direction. She just knew he was there – like an extra arm or leg. She had already spotted the nearly empty box of doughnuts and grabbed the very last one. With a mocking look straight at him, she took a bite and acted like it was the best doughnut she had ever tasted – even though she hardly tasted it at all. Then she walked away toward the women’s table as if she were ignoring him completely.
Chad wasn’t all that worried about not getting a doughnut, he was more worried about Robin and what she might do. He finished pouring his coffee and carried it over to the women’s table where he found a chair nearby and sat down extra slowly so as not to irritate his backside any more than it already was. He decided to try to stay as quiet and as out of the conversation as possible today, just to be safe. But then, that was always what he wanted, the other women just never seemed to let him.
Robin noticed how slowly Sissy sat down. She wondered if Mel had beat him last night. But after watching him sit, she was betting that Mel had. Well, he deserved it! But obviously the lesson hadn’t stuck properly. Just like a child! The idiot!
She watched him as one of the women teasingly asked him about when he was going to see Derek again and again Chad tried to explain that he and Derek weren’t “dating.” As funny and interesting as that used to be for her – last week, now she knew that something much different was probably behind it all. She didn’t know exactly what, but those questions couldn’t be asked here.
As the other women laughed and talked, she sat silently, thinking, brooding.
“Robin,” one of the women broke her concentration. “You’re being awfully quiet today. Are you feeling alright?”
Robin shrugged. It’s just that… she looked straight at Chad… “the… baby… has been driving me crazy lately.”
Chad instantly understood which baby she was talking about. Not her own.
“Oh,” the woman said in reply. “Well, he’s what? One now? Once they reach that age where they can start moving around faster, they just seem to get into the darndest things!”
“Don’t they!” Robin replied, glaring at Sissy once again. She was saved from any further answer as the talk around the table instantly turned toward the ones with young kids. She had a baby of her own, a one-year-old who had just recently learned to walk and was now getting into all kinds of mischief. Was she now going to be saddled with another baby a – how old was Chad anyway? Not that it mattered. He wanted to be a baby and the more she thought about it, the more she realized he was acting like one! The jerk! He couldn’t even apologize properly!
The women started getting up from the table to head back to their desks and Robin did the same. So did Sissy. Amid a fairly large group of women, they both headed back out into the hallway. A few minutes later, Chad was trying to follow behind her as quietly and as unobtrusively as possible again. Robin knew he was still following her, she just chose to ignore him – for now. They turned down the last hallway where their cubicles were located. Robin walked right past his cubicle, heading for her own. But she stopped at the entrance and turned around. He had just turned into his own cubicle. “What the hell is wrong with you?” she asked.
Chad was taken aback again. What had he done wrong now? He knew he hadn’t uttered a word. In fact, he had hardly made any sound at all.
“I got an email from your… mistress,” she spat the word again... “a little while ago. And that silly little apology you gave me earlier wasn’t even close to what you were supposed to do!”
Chad saw her suddenly heading for him again and he backed away from her, straight into his chair where he winced a bit at the pain still in his backside as he fell into it.
Robin noticed the look on his face as he sat down. “What’s wrong? Did your… mistress… beat you last night?” When she got no answer, she yelled, “Tell me!”
Chad nodded, as the fear started to grow in him.
“I didn’t say nod your head. I said tell me! Did she beat you?”
“Y… Yes,” Chad stammered.
Robin nodded. “Good! I hope she beats you every night – because I can’t think of anyone who deserves a beating more than you!
“I still can’t get over that you’re doing such a stupid thing! It’s… insane! And worse… you want to be a baby too? I just don’t get it!” she said with a shake of her head. “Why would anyone… It’s stupid, stupid, stupid!”
She paused for a second. “You want to be a baby? Well, from what I see lately you’re behaving more and more like one every day! Take that stupid excuse for an apology you gave me earlier. What is it? You’re not ‘man’ enough to do it properly? Well, we know that already! You’re not even enough of an adult to take the responsibility of doing what you’re told! Like a little baby, you tried to get away with something and thought I wouldn’t know about it! Well I do know about it! I know exactly what kind of apology you were supposed to give me, right down to what you were supposed to say to me!”
She stared at him sitting fearfully in his chair for a moment. “Get up!” she ordered as she turned around and started out. “Let’s try it again!” She didn’t know if she was angry or what, but she went straight back to her cubicle.
Chad was in a state of shock. She knew what was supposed to be in the apology? Obviously she had heard from Mel again. Still feeling a bit fearful, he got out of his chair and headed back to her cubicle.
Robin was opening up her email program when she heard him enter her cubicle again. She turned on him quickly. “Did I say you can come in here? Back up! Back out into the hallway again!” She watched till he was back to the middle of the hallway before turning her back on him. She opened up Mel’s email and read it through thoroughly, paying strict attention to the words that Chad was supposed to say. Then she turned around to face him again. He was still in the middle of the hallway. Good! “Okay, I’m waiting,” she said. “Now let me see how you were supposed to apologize.”
Chad stood there for a second. He didn’t know why he felt a bit afraid, but he did. He inwardly gulped, then looked up and down the hallway to make sure nobody else was around that would see him.
“I’m waiting!” Robin said impatiently.
Chad again started with a small curtsey toward her.
“Stop right there!” Robin yelled angrily. “That’s not what your friend said you were supposed to do!” She turned quickly in her chair and read out loud from Mel’s email so that he could hear. “He was supposed to give you a very nice curtsey, pulling his skirt as wide as possible while bowing his head in respect to you. Then he was supposed to stand up straight with his feet together and his hands clasped nicely in front.” She turned back to him again. “Was that little… thing… you just did anything at all like what you were supposed to do?”
The fear inside of Chad grew a bit more. “N… No,” he replied.
“See! Once again you’re acting like a child and trying to get away with something! Geez! Now let’s see it properly!”
Once again Chad looked up and down the hallway to make sure nobody was watching.
This time he curtseyed exactly the way Mel wanted him to, pulling his skirt wide, bowing his head, and standing back up with his feet together and his hands clasped nicely in front of him. Then he launched into his little apology speech – in his girly voice. When he was done, he repeated his curtsy routine once again.
Robin stared at him for a moment, then grunted and shook her head. The term sissy was starting to grow on her. The idiot! She shook her head. “Come here!” Chad started moving toward her cubicle but she stopped him just before he could enter it. “Now tell me,” she said a bit more calmly, “what the heck is your ‘sissy voice’?”
Chad’s eyes went wide. Mel had told her about that too? He looked down at the floor bashfully. “Um… She makes me talk that way because it makes me sound more childish and like a…” his voice dropped to almost a whisper, “sissy.”
Robin just stared at him. More childish? Like a sissy? Well that figured. “What way? Explain.”
Chad was getting more and more uncomfortable talking about it. “Um… Well basically, I replace all the ‘R’ and ‘L’ sounds with ‘W’. He looked up at her finally. “So Robin comes out as ‘Wobin’ and hello sounds like ‘hewwo’.”
Robin nodded. “I see.” Even though she wasn’t entirely sure. “According to your mistress friend Mel, you were supposed to give me that apology in your sissy voice too. Weren’t you?”
Chad nodded bashfully. “Yes.”
“Then why didn’t you?”
He shrugged. “It’s embarrassing,” he finally admitted.
“And curtseying like a… I don’t know what, and everything else you do isn’t?”
He nodded. “Yes it is. Very!”
“So what’s the difference between this and everything else? What makes talking like an idiot any more embarrassing than… whatever?”
But Chad didn’t really have an answer so he just shrugged his shoulders indicating he didn’t know. He felt like a child being yelled at by a grownup.
Robin rolled her eyes and shook her head. “Now… Do you think you can go back there and this time, finally do it properly?”
Instead of answering, Chad just nervously nodded his head. Then he started moving back out to the middle of the hallway again.
Robin shook her head. “Geez,” she muttered. “Just like a child.” Then a little louder she said so he could hear, “You want to be a baby again? At the rate your going, you’re going to get there really soon! I can’t believe how childish you behave. Why didn’t I ever notice it before?”
Chad made no reply. He just backed up to where he had apologized from before. Twice! He glanced even more nervously up and down the hallway. Out in the open like this, doing it over and over again, was starting to tempt fate a bit more than he would like. Once again he dropped her the rather lavish curtsey and once again he launched into his little apology speech – this time in his sissy voice, and once again he finished with the same curtsey again. When he was finished, he just stood there in the hallway, staring at her, unsure about what he should do.
Robin had taken the whole performance in. Somehow, changing the voice the little bit that he had gave the whole thing a different meaning. Somehow, it made the whole thing seem more childish. Somehow, it made her think again about the term sissy – which was really starting to make more and more sense to her. She saw Chad suddenly start walking back towards her again. “Stay there!” she ordered, and watched as he backed up again to stand right where he had been.
Now what? Now what was she supposed to do with him? Send him back to his desk? Try to put him out of sight, out of mind? Somehow, that all seemed… just wrong! He had made her so angry – first when she found out about his stupid bet and his… inclinations, and secondly by not at least apologizing correctly to her. He had tried to shrug her off as not deserving of a decent apology. Well… She could deal with that!
“Do it again!” she ordered.
Chad was shocked. “Again? But I did it perfectly. I promise!”
“I didn’t say you didn’t. Now do it again!”
Chad briefly closed his eyes in frustration, then once again launched into his little routine.
Robin watched him carefully one more time. When he had finished again, she said. “Again!”
Chad was dumbfounded. She really wanted him to do it again? Why? But before he could begin again he heard her say, “And again… And again… And again… And again. Just keep doing it over and over again till I tell you to stop!”
Keep doing it? “But what if somebody sees me?” he asked nervously.
“I don’t care! You’re the one who didn’t do it right in the first place! You’re the one who likes being embarrassed. I hope someone else does see you! Now do it again!”
Horrified, Chad again launched into his little routine, but halfway through it, he saw Robin turn away from him and open up one of the programs on her computer like she was ignoring him. When he finished, he stood there and waited.
“Keep going,” Robin ordered with her back still to him. “Just keep doing it – over and over and over again.”
“How many times?” Chad asked, still not believing what she wanted.
Robin turned briefly back to him. “Only a child would ask a question like that. I said, just keep doing it. There are no set number of times. You’ll do it till I get sick of hearing you!” Then she turned away again.
What could Chad do? He went into the formal curtsey again and kept going.
Robin tried to work a bit on the things she had to finish, but something was nagging at her brain – besides the sound of Chad droning on in the background behind her. Giving in, she opened up the email from Mel and typed. “The apology he gave originally wasn’t even close to what it was supposed to be. I’ve corrected the situation and he is practicing it over and over again now. Do you always have this much trouble with him?”

The Bet - Chapter 46 (Tuesday – week 7 Part 1 of 9)

2011-12-27T02:51:00.000-08:00

The Bet
by Karen Singer

Chapter 46 (Tuesday – week 7 Part 1 of 9)

It was the most peaceful sleep she had had in a while. But that doesn’t mean her dreams were without conflict – which doesn’t mean that her dreams were without pleasure too. For in her dreams, she was in bed, making love to… Ray – at first. Because in the middle of her dream, where things were just starting to get hot and passionate between them, Derek showed up and ruined it all. But this time it was an angry Derek. Angry enough to grab Ray and pull him right off of her. She was frightened by Derek’s rage, but the fright didn’t last.
Ray and Derek argued – over her! As she laid back in her bed, watching the two hunks, she felt nothing but thrilled as they continued to argue about which one of them was going to make love to her. She wanted Ray to win because he was there first. She had already started with him. But… but there was just something special about Derek too. She really kind of liked him better for some reason. So, she was torn.
The argument turned from a very heated discussion into a fist fight! In her dream, she sat up on the bed to watch and cheer for… both of them. She felt so honored that each of them would want her so badly. So special! But then someone else climbed up onto the bed with her, someone she hadn’t expected. Sissy was suddenly at her side, holding her, kissing her, caressing her in the most intimate ways. And his touch felt so good, so arousing, so sensual.
She laid back on the bed and let Sissy make love to her while she kept watch on the two hunks fighting over her in the distance. How perfect could anything get?
But one of the two big men noticed what Sissy was doing and their fight stopped. Together they rushed at her… and Sissy. In their rage, they both tore Sissy from her grasp and threw him angrily away from her. Together they kicked and beat him horribly, chasing him further and further away from her, until finally, Sissy had no choice but to run away as fast as he could – never to be seen again.
She felt heartbroken. Victorious, the two big men returned to her bed together, and together they caressed her and made sweet love to her, but it was a bittersweet love. Despite them, her heart ached horribly for Sissy, and despite the two hunks lavishing their attentions on her, she yearned for him.
The alarm on her clock buzzed and she awoke. She felt like she had gained something – but in the process had lost something bigger. She just didn’t know what that something was. She reached over and turned off the alarm as she sat up on the side of the bed. Her need for coffee was so ingrained in her that she didn’t even think about it. She grabbed her robe as she got to her feet and slipped it on as she headed out toward her kitchen.
As she watched the freshly brewing coffee dripping into the pot, her mind remembered that she had a date tonight – with Ray. She was looking forward to that. She was really hoping that it would be fun… and hopefully, would lead to – something else! But later tonight was still a long way off and other things soon made their way into her consciousness. Things like – Sissy. He had been so great last night – again! Really, the little sissy had the most wonderful touch. And his tongue! She remembered that he was supposed to be going out with Sandy and Cassie later tonight to visit their friends. She had a feeling that that was going to be an interesting trip.
Her coffee finished brewing and she reached for the cabinet to get a cup, but she had to stop and correct herself as to which cabinet to open. She hated change, especially when it involved anything that she had to do before she had her coffee! A minute later, her coffee poured, she took a sip and carried it into her living room where she sat in her chair.
Thinking about Sissy, soon led her to think about Robin. Yesterday had been strange. Not at all what she had expected. And Robin had actually ordered Sissy to suck his thumb! At work? Amazing! Did that mean… she almost didn’t dare to think the thought… did that mean that Robin might become someone who she could count on to help with Sissy while he was at work? It seemed too remote a possibility to really give credit to. But… was it possible?

One minute he was sound asleep, the next, loud blaring rock music poured out of his pink clock radio, jarring him from a sound slumber into instant confused wakefulness. And he had been sleeping so good! As soon as he could collect his wits enough, he rolled over onto the floor from his blow-up mattress, scattering a few empty baby bottles in the process, and got to his knees, where he immediately reached over and turned the overly obnoxious music off. What a way to wake up every day! Ugh! But he had to admit, it certainly worked!
He took a deep breath and took stock of himself. His diapers were overly bloated as usual – messy too. His backside itched terribly because of the beating he had gotten last night. He hoped it wouldn’t turn into diaper rash. He had put a bra on before going to bed last night to help support his glued-on breast forms. They still hung heavily from his chest. Of course, his penis was locked away inside of a chastity device and had been for a long time now. It had become mostly… useless. And last night… last night she had taken him in the rear… and he had orgasmed that way. Unbelievably!
He climbed awkwardly to his feet, hampered by the thick diapers he was wearing. He resisted the urge to scratch a bit at his irritated backside as he stumbled awkwardly out toward the kitchen where she usually left him his note. Once again, the note was there, but it might as well have been the same one she left every day now. Except… this one had one extra line added. “Wear something with a full skirt today!” What did that mean? Why? Wearing a skirt was a given now – he had no other clothes anymore except women’s clothes. And the way things had worked out, dresses and skirts worked the best for him – they helped hide the bulk of his diapers. Not to mention that she had restricted the number and style of women’s pants that he could own anyway.
Having no clue why she should specify a full skirt, he gathered his three required baby bottles from his refrigerator and carried them out to his only chair. Gingerly, he sat down and put the first one to his mouth as his eyes wandered over the childishly colored pictures she had made him create in the restaurants. But he had seen those pictures enough now that he barely noticed them anymore. Why a full skirt? And… which one should he wear?

Mel stirred his baby cereal in the pot on her stove. She glanced at the clock. – it was almost time for him to be here. The knock on her door was actually two minutes early. She turned the stove off and went out to open it.
“Good mowning Mistwess,” Chad said in his sissy voice as he curtseyed for her.
“Good morning Sissy,” Mel replied as she stood back out of the way to let him inside. She waited till he deposited his diaper bag and purse under the table she kept by the door. Then she looked him over. His hair was styled – good enough. His makeup looked – acceptable. She noticed that he was wearing the pink ear studs again today along with the rest of his pink jewelry. She could tell from his shape that he was wearing the required two diapers, waist cincher, and all-in-one girdle under his clothes. His reddish brown blouse was frilled along the entire neckline and went well with the colorful pattern on his skirt. And on his feet he was wearing a pair of brown ankle strap heels. Overall, he looked… not too bad – for a guy wearing women’s clothes.
She reached out and pulled his skirt to the side, seeing how wide it would go. Very good.
“This is the fullest skirt I had,” Chad said in his sissy voice as she pulled it to the side. But the moment he opened his mouth to say it, she got mad and rushed off. Chad knew he had messed up before the words were completely out of his mouth. All he could do was to curtsey as she rushed back toward him, her thick yardstick in her hands. “I’m sorry Mistress,” he said in his sissy voice. “I forgot.” There was nothing he could do but to stand there and accept the blows from her stick as she hit him on different parts of his body.
“When are you going to learn to curtsey every time you open your mouth?” she said angrily as she hit him. Chad made no reply.
“One way or another, you’re going to learn!” she said as she offhandedly hit him two more times. “Now get in there and get up in your highchair!”
A few minutes later, Chad was trying to shovel horrible tasting baby cereal into his mouth, using a tiny baby spoon held in his left fist, while he was sitting in his highchair wearing a bib.
Mel poured herself another cup of coffee and leaned back against the counter to watch him like she usually did. “I’m glad things went better with Robin yesterday than you thought they would,” she said.
Chad looked up from his breakfast. “I’m not sure it was good at all! She was so angry – even when she left yesterday.”
“I would say that ‘not getting fired’ is something good.”
Chad nodded. “Yeah! That part is a big relief!” He dug another spoonful of the mush out of his bowl.
“I want you to keep telling me about every little thing she says and does with you today. Like yesterday, if anything happens, I can’t help you if I don’t know what’s going on.”
Chad shrugged, which caused him to spill a bit of the baby cereal already on his spoon. “That should be no problem… unless she makes me keep my thumb in my mouth all day again. It’s really hard to type like that! And I still don’t know why she did it!”
Mel wasn’t exactly sure either. “Just make sure you keep doing whatever she says! And don’t forget to apologize to her as soon as she gets there!”
Chad said nothing as he shoved a bit more of the lousy tasting cereal into his mouth. The apology she had made him practice over and over again last night. He still wasn’t sure he would really go through with it – at least not quite like Mel wanted him to.
As soon as he had finished his breakfast, Mel released him from his chair, but she didn’t let him go to work yet. “Let me see your apology for Robin again,” she ordered.
Chad inwardly groaned. He dropped a small quick curtsey to Mel first – just in case. Then he launched into his little “routine” for Robin. He grabbed his skirt with both hands and dropped into as nice a curtsey as he could…
“No! Spread that skirt as wide as it will possibly go. I want it flared as much as possible! That’s why I asked you to wear it in the first place! Now do it again!”
Chad grunted, then dropped yet another little curtsey for Mel – just in case, then he tried it again. He grabbed his skirt and dropped into his curtsey again – this time pulling wide with both arms as far as the skirt would let them go.
“Better!” Mel commented. “Much better!”
Chad bowed his head momentarily, then he rose up again and brought his feet right together next to each other and clasped his hands in front of him. Then he launched into his little speech. In his sissy voice he said, “I’m sorry Robin that I didn’t do exactly what you told me to do yesterday. I promise not to give you any more trouble and to do whatever you say from now on.” Once again, he dropped into another curtsey, spreading his skirt as wide as possible and bowing his head, before he got back to his feet again and put his hands together in front of him. He turned to Mel and curtseyed. “Was that good enough?” he asked.
“Do it again,” was Mel’s only comment. She made him go through it four more times, just to make sure he had it down perfectly. “Now don’t forget. You do it exactly like that. And this time, use your sissy voice too. No sense practicing it this way and then messing up by doing it differently. Got that?”
Chad curtseyed. “Yes Mistress.” What else could he say?
A few minutes later, Mel watched him driving off toward work. She went back into her house and turned on her laptop. As soon as it was ready, she opened up her email program and began working on an email for Robin. “Okay,” she said out loud to the empty room. “Now we’ll see what we’ll see! Let the games begin!” And with that, she made a little flourish with her hand, and hit the send button.

Robin parked her car, gathered up a load of different things into her arms that she “might” want during the day, and headed in toward the building. She didn’t see Chad’s car yet, but that didn’t mean that he wasn’t here already. Her problem this morning was that she still wasn’t sure what to do about him – or how she should go about even talking to him. She wasn’t even sure she really wanted to talk to him yet… if ever. So she wasn’t really looking forward to seeing him again.
She had made the stupid jerk spend several hours yesterday afternoon sitting with his thumb in his mouth. And the idiot had actually done it! Well, he had deserved it! He wanted to be a baby? Served him right! She had been in no mood to be played with yesterday. She still wasn’t, but she was at least thinking a bit clearer today. It still galled her what a stupid pervert the guy had turned out to be – and she never had a clue! Imagine, wanting to be somebody’s… slave! The idiot! And he wanted to be a baby too? The two just didn’t jive in her mind. Not that anything about him did anymore.
As she approached his cubicle, she slowed her steps a bit. With a rather angry look on her face she looked into his cubicle as she walked past – and breathed a sigh of relief. The jerk wasn’t in yet! Maybe he’d stay out the rest of the day… wishful thinking.
She dropped her load of things onto her desk. Rummaged through her bag till she found her mirror and checked her face and hair. Stowed her bag into her desk drawer, and turned on her computer. Just a normal day, she tried to tell herself. But she knew better.
It took a few minutes for her computer to fully boot up. When it did, she opened up her email program that she kept open all the time. She was surprised to see an email from Mel – already! What did the crazy woman want now? Did she dare open it? But opening it was a foregone conclusion.

Dear Robin

I’m just checking to make sure that Sissy really did apologize to you “properly” as soon as he arrived today.

Please let me know as soon as he does – or doesn’t!

As always, feel free to call or email me,
Mel

Apologize? Robin remembered from a previous email yesterday that she should expect a “proper” apology from him. Whatever “proper” meant. But so far, the jerk hadn’t showed up yet. Fortunately! She closed the email and opened up the internet to check the weather.

Chad knew he was running a few minutes behind, so he was fairly sure that Robin would be in already. He didn’t see her as he approached his cubicle, but that didn’t mean anything since her cubicle was beyond his. Treading lightly, he entered his cubicle. He wasn’t even aware of it, but he was trying to make as little noise as possible so as not to anger Robin, or even alert her that he was here. He stowed his purse in his desk drawer and closed it quietly. Then he sat down gently, as much from trying to be quiet as in difference to his still stinging backside. He started logged into his computer and was alarmed at how noisy the keys on his keyboard seemed to make.
“Sissy!” Robin’s voice called angrily over the wall between them. “I hear you in there! Are you supposed to apologize to me?”
Well, he knew he couldn’t avoid Robin forever. “I’m just booting up my computer,” he called back, looking for an excuse to delay things.
“According to your… mistress,” she spat, “you’re supposed to apologize – first thing! So by my book, that means first – before you do anything else!”
Chad gulped. She still sounded awfully angry. Would she make him sit here all day with his thumb in his mouth again? He hoped not. Instead of answering, he hurried out to see her.
Robin didn’t even know why she cared so much. Well, the jerk probably should apologize to her – for a multitude of things! Not that she was really in any mood to accept an apology from him. Still… She saw him coming around the corner and starting to enter her cubicle. “Stop right there!” she ordered quickly. “I don’t want you that close to me. Back up!”
Chad was surprised. Back up? But he backed away from her till he was just out of her cubicle.
“Further!” Robin ordered. “Like… the middle of the hallway, at least.”
Chad looked around, fortunately, he didn’t see anybody coming. He backed up further.
“Now. I guess I’m supposed to listen to some kind of stupid apology from you? So let’s have it so I can stop looking at you. Not that I’m probably going to believe anything that comes out of your mouth,” she muttered.
Chad was a little taken aback by her attitude, but he was supposed to apologize, so he figured he better apologize. He just didn’t see himself doing it quite the way that Mel wanted him to. Once again, he looked up and down the hall to see if anyone was coming – fortunately not. He wasn’t about to give her the full version, but he did drop a quick little curtsey for her as a start. “I’m sorry Robin,” he said in his girly voice, “for taking my thumb out of my mouth yesterday after you told me to keep it there.” Should he add any more? It was already more than he wanted to say, but he figured he better add one more little thing that was – sort of – what Mel wanted. “I promise I’ll try to do better and listen to what you want from now on.” Then, since he had no better way to show that he was finished, he dropped another quick little curtsey. He watched her just staring at him. Was it enough? Could he go back to his desk now?
“Huh!” Robin grunted as she shook her head. “Listen to what I want? I don’t want to see you! Get out of here!” She purposely turned her back to him, hoping he would get the point.
Chad was just glad it was over and hurried back to his desk. As soon as he was done logging into his computer, he decided he had better tell Mel about Robin’s reaction.

The Bet - Chapter 45 (Monday – week 7 Part 7 of 7)

2011-12-23T03:07:00.000-08:00

The Bet
by Karen Singer

Chapter 45 (Monday – week 7 Part 7 of 7)

Instead of having him practice his ballet, Mel had him keep busy with cleaning the apartment instead. But every few minutes she called him back to practice his little apology for Robin again. She enjoyed watching him, she just wished she could be there to see it in person.
But finally, watching him curtsey for her over and over again had enough of an effect on her. She got up from her seat in the living room. “Strip down to your diaper and nothing else!” she ordered as she headed for her bedroom. Chad did just that, but not before curtseying one more time, even though she was walking away from him. It was better to be safe than sorry!
It took him only a few minutes to get himself down to just his diaper. Removing his bra left his glued on breast forms hanging from his chest with no support. They felt all too awkward and heavy that way as they pulled against the skin of his chest. Removing his waist cincher though was perhaps his biggest relief. The darn thing was all too tight and confining. He had a vague idea of what would be happening next, but knowing Mel, he dared not make too many assumptions.
She was gone a while, but eventually, she called him into her bedroom. When he got there, she was holding one of her scarves in her hand. Out of the corner of his eye, he noticed some ropes attached to her bed, but they were mostly pushed out of the way. The minute she approached him with the scarf, his assumptions became confirmed. He curtseyed to her – just because he dared not do it.
“I’m going to put this on you again,” she said, “and I’m not going to tie you up… yet.”
That surprised Chad a bit. He had already seen the ropes attached to her bed. But then she did say… “yet.”
“But so help me. If you even do anything to take this off – or if it somehow even falls off, then I’ll make sure you’ll regret it for a very, very long time!”
The way she had said it left him in no doubt, and his thoughts instantly went back to the beating she had given him earlier. His backside still burned terribly. He curtseyed. “Yes Mistress.” What else was he going to say? That he was going to do everything he could to get a look at her gorgeous naked body? He knew better! It wasn’t going to happen! Never once in their relationship had he been allowed to see her naked. He had only been allowed to touch her. But just touching her was reward in itself. She felt so… beautiful! A moment later his sight was totally cut off as Mel tied the scarf tightly around his head – then she pulled on it again, making sure it was extra tight and secure.
Finally feeling satisfied that he couldn’t see her, Mel began undressing. She still didn’t understand her strange aversion to him seeing her naked, but after all this time, it was just something that she accepted. She climbed up on the bed. “Make love to me,” she told him. It was Sissy standing there wearing nothing but a diaper, his breast forms hanging oddly from his chest – but it was Ray she was trying to picture in her mind. Ray, who had driven her wild in the movie last night. Ray, who she would be going out with tomorrow night. Sissy would be nothing more than a warm up before Ray. Something to take some of the edge off of her… anticipation.
Chad groped his way toward the bed, then up onto it. He felt for her body and his hand connected with her naked breast. Surprised, he kept it there as he brought his body over to lay close to her. The skin on her breast felt so soft, so smooth. He moved his hand over it, lightly flicking the nipple with the tip of his finger. He allowed his hand to roam further, feeling more of her. She felt… wonderful! Unable to help himself, he got to his knees next to her so he could feel her whole body with both hands. He allowed his hands to roam in opposite directions, sliding ever so tenderly over her ever so smooth skin. He heard her moan and felt her writhe slightly. The feeling of her was exquisite! And he was only using his hands! Having his sight blocked off allowed him to truly feel how wonderful she felt. It allowed him to concentrate harder on the things that were really important. He allowed both hands to probe, and squeeze, and caress, drawing as much pleasure from it as she did. The only thing was, that sexually, he was completely denied any reaction. All he received sexually was frustration. But he was so very glad that she was enjoying the full benefit of his touch.
Mel writhed and whimpered softly as his magic hands worked their way over her entire body. There was just something so sensual about his touch. Several times his one hand found her ever moistening sex and lingered there for a moment, but it was only a moment, leaving her hungry for more. The fingers of one hand seemed to grab her breast a bit firmer just before she realized he was lowering his head toward it. She was struck but the odd sensation of his breast forms, both of them, rubbing firmly against her other breast, stimulating it. But that was only a side sensation. She was more interested in watching as the hand on her other breast guided his mouth directly to her nipple. He sucked on it for a moment, like a baby? Then his mouth pulled away slightly and she felt his tongue flicking lightly over the tip of it. Her breathing quickened – especially when his other hand found her dripping sex again – and stayed there. She arched her back as his fingers began probing deeper – deeper but still lightly. As if teasing her. Making her want more… more… more! Moments later, she was rocked by her first orgasm. Exquisite!
Chad let her come down slowly from her orgasm. But before he could do anything else, he felt her hands grabbing his hair, pushing his head down between her legs. He resisted, but only to the point where he could move his body, climbing over her carefully to position himself better. But her hands never quit their grip in his hair, and as he dove down with his tongue into her, he felt her pulling his head harder and harder into her. He couldn’t see them, but he felt her legs writhing over his body on both sides, one of them moving up and down his back. Her second orgasm came fast and much stronger than the first.
Mel’s blurred vision stared at the ceiling, but she had no interest in seeing anything. All she was interested in was how good Chad’s talented tongue felt as it still worked away at her. She felt momentarily spent after her orgasm, but that didn’t matter. All that mattered was how delicious Sissy felt as he continued to stimulate her so wonderfully. He was going slower now and she let up a bit on her grip. She hadn’t realized she was pulling on his head so hard. She allowed herself t take a deep breath and close her eyes, the better to enjoy everything she was feeling. Heaven! And slowly, ever so slowly now, she felt her next orgasm building again. The only thoughts capable of getting through to her now were the feelings that she felt throughout her entire body.
Chad kept at her till eventually she had one more orgasm. He had gone slower that time, much slower. As she came down again, he was aware of her breathing slowing down, her legs on each side of him calming, her entire body seeming to relax. He felt her pulling on his hair again, but it was in a different direction, pulling him away from her. He pulled his head away, and climbed off of her, once again laying next to her. He put his arm over her and held her as she continued to relax more and more. Such a pleasure. He couldn’t help but wonder though at what it was that she felt. Women were capable of having orgasm after orgasm, while he was capable of… nothing. But that didn’t mean that he didn’t enjoy making her feel good. Worshiping her body by just touching her. He felt… honored that he was capable of giving her the pleasure that he could. He might not be any good in the ways that most men were, but at least he could do this much for her.
He felt her moving, rolling over on top of him. The weight on his breast forms was crushing, but he didn’t care. He felt her head come down next to his and he felt her lightly kiss his neck over and over again. If he had been any kind of a man, he knew that his useless penis would have responded quickly. But… he wasn’t that kind of a man. Not anymore. Not since she had locked away all of his main source of pleasure.
He felt her moving off of him again to his other side, kneeling next to him, just as he had been kneeling next to her a little while ago. Something tugged lightly at one of the breast forms glued to his chest, and he realized she was rubbing her hand lightly over it, just as he had done for her.
“Do you feel that?” she whispered. “Does that feel as good for you as it does for me?”
How could he tell her that all he really felt was the light pulling and pushing as the breast form tried to move under her hand. But he said nothing at all. He felt her hair tickling his chest, and realized she was kissing what would have been his breasts if he were a real woman. It was an odd sensation, totally useless in its intent, yet oddly stimulating never the less.
He felt her pull her head away from him again. “Scootch over a bit, this way,” she said as she moved back, and finally off of the bed. She pulled on his arm till he was laying on the very edge of the bed. “Stay there. I’ll be right back… And don’t fall off!”
He heard her leave. She was gone a short while. Then he heard her back again and doing… something. Something that involved the bed. He could feel her on the other side of it, doing… something. Then she was back again, right at his side. He felt her grab his arm with one hand while her other hand touched his body.
“Roll over to the other side now,” she instructed as she pushed lightly to guide him.
Chad rolled over onto his stomach and started moving his body sideways toward the other side of the bed. He quickly discovered that what he had felt her doing was protecting her bed. His hands encountered multiple thicknesses of diapers under his entire body.
“Okay,” she said as he reached the spot she wanted him to be in. He stopped and started to roll over onto his back again. “No,” she told him. “Stay face down.” But the position wasn’t quite what she wanted. “Up on your hands and knees,” she ordered.
Chad did as instructed, but now he was getting confused. On his hands and knees? He felt her hand on his back again as she told him to move forward a bit toward the head of the bed. He crawled forward slightly, then more, till she told him to stop. A moment later, she was pulling open his soaking wet diaper and removing it. The air felt cool and odd as it caressed the parts of him that were forever packaged inside of the warm diapers. A moment later he realized he was involuntarily peeing as the cool air stimulated him. He heard Mel laughing as she stood by and watched. As used to it as he already was, he felt embarrassed by his lack of control.
He felt her moving up towards his head more, and a second later he felt her tying the rope to his wrist on that side. She moved back and fastened his ankle next. Then she moved around to the other side of the bed and bound that side of him. He had to wonder why. He certainly wasn’t planning on going anywhere. And bound like he was he could still stretch out and lay down easily. But… it was her game.
He could hear her moving around near him, but he couldn’t tell what she was doing. Not till he felt the cold shock of her hands full of lotion suddenly rubbing all over his still hurting backside. But this time the hurt died quickly and was replaced by more and more pleasure, especially as she purposely moved closer and closer to his waiting back hole.
Mel let her finger slip slightly inside of him, and saw the immediate reaction as his whole body stiffened. He loved this. Well, tonight she wasn’t going to disappoint him. She played with him there for a minute, moving her finger in and out of him – as much to spread the lubricant as for his enjoyment. Then she pulled her hand away again.
On her nightstand, she had already selected one of the colorful dildos to use on him. The one with all the swirled ridges along its length. She picked it up and placed it against his asshole. His sudden intake of breath was obvious. So was the stiffening in his entire body again. She held the toy there for a moment, but she couldn’t keep it there long as he started pushing back toward it, wanting it, almost more like needing it. She let him have it, but only a little at a time. But the further it went into him, the harder it was to grip the toy, especially since the swirled ridges on it were acting like screw threads and the whole thing kept trying to turn around in her hand. She held on tighter though and he soon loosened up so that it wasn’t as much of a problem.
It seemed like no time till he was pushing and pulling like crazy against the toy in her hand. He seemed… desperate in some way. And she supposed she understood that – seeing as how she had completely denied him any chance of an orgasm. She was simply amazed at how desperate he seemed to be, pumping himself, screwing himself, fucking himself against the toy in her hand. But before long, she saw him shake his head again and he slowed down further and further. With the toy still buried half in his backside, he finally moved his hands forward and slumped down on his elbows in defeat.
She was disappointed that he didn’t try longer. But she understood that. Maybe… maybe he would enjoy a different toy? She opened her drawer and began sorting through all the different options available to her. Colorful options and… oh… Her eyes fell on the strap-on dildo she bought to use on him… but had wound up strapping to him and using it on herself instead. The thing had a small side that was supposed to stimulate her too. Would it work? Only one way to find out.
She pulled it out of the drawer, found the smaller end and fastened it to the back of the device. Then she set about fastening it to her. It was an odd process and it felt odd around her hips. It especially felt odd from the part that was buried inside of her. But now that it was there, she was starting to get sexually stimulated again. The odd fake penis stuck out in front of her strangely. As she moved around, it accidentally bumped against the side of the bed, stimulating the inside extension in the process. She found that very interesting!
He was still slumped down on his elbows. She didn’t want that now. “Get up again,” she ordered and waited till he had once again gotten to his hands and knees. But she didn’t want him to slump down again. She found two more lengths of rope, but before she used it, she grabbed one of his wrists and pulled it out to the side, pulling it against the rope holding it to the headboard, until she could place his hand on top of the phallic piece sticking crudely out from her groin. “Feel that?” she said. “That’s for you!” She wanted him to know what was about to be done to him. She wanted him to know that he was about to get screwed – like a woman!
She grabbed the rope then and tied his wrists to his knees on both sides. Now he couldn’t move his hands or his legs forward or back. He would be stuck in the position he was in. Perfect. Just the way she wanted him.
She climbed back up on the bed behind him, but the fake penis sticking out from her was harder to deal with than she thought. She had to maneuver around just to get it close to his asshole and she kept bumping and scraping it against him in the process. How did men manage to do anything with these things? And then it was even harder to get it exactly right and control how she wanted to push it into him. She had to use her hands to guide it into place and hold onto it. Then she pushed lightly with her hips till it finally slipped partially inside of him. Only then did she release her hands and grab the sides of his body instead. She could feel the pressure from the little piece inside of herself, but concentrating on it as well as what she was trying to do to him was difficult. Slowly and carefully, she pushed the fake penis attached to her inside of him.
Chad was a bit scared. Yes, he loved having her play with his asshole. Yes, he loved all her toys. But this… this seemed different. And once the damn thing was inside of him, it felt bigger, fatter than any of her other toys. He felt her pushing it slowly into him, further and further, more and more. He was just glad he was already so loosened up from her previous toy. And then he felt her pulling away again, pulling away with her body. And the toy that was in him was obviously moving with her body. It was such a strange sensation. Several more times he felt her pushing slowly into him all the way, then pulling back again, almost all the way but never quite removing the crazy thing.
Mel thought she had the hang of it now. It wasn’t really so hard at all – once she had gotten it into him. And yes, she did feel something from the little piece inside of her – and it really felt pretty good. Certainly not like anything real, but it was… interesting. Somewhat stimulating too. As she moved slowly back and forth, she could see him relaxing more and more, getting into it more and more. She leaned over him now, the new position made it harder to pump against him, but she kept going anyway as best she could. She reached under his chest and began fondling one of his breast forms. “Do you like this?” she asked. “Can you feel me playing with your tits the way that you play with mine?” She almost giggled. She was fairly sure he couldn’t feel much from his fake breasts at all – but you never know. “Does this make you feel more like a woman now? A real woman?”
Something about her words hit a nerve inside of Chad. He shuddered involuntarily at the thought and clamped down a bit harder on the phallic device inside of him as he began trying to actively pump back and forth against her – increasing the pace a bit.
Mel noticed his reaction, especially when he began speeding things up. She figured she must have said something that interested him. She almost giggled. She had wanted to imagine it was Ray making love to her earlier, but once he had started, she could only think of Sissy instead. So maybe… She leaned close to his head again and whispered. “Can you imagine that I’m Derek, and this is what Derek would be doing to you?”
Derek? Derek making love to him – like he was a real woman? Derek fucking him – like a real woman? But the feeling of the fake penis being pumped in and out of him made that scenario all too real and easy to imagine. He involuntarily felt his body tighten as that thought increased his sexual energy.
Mel noticed the change once again – and continued. “Can you remember Derek holding your hand in the movie? Dancing with you in the restaurant? Did you feel like a real girl then?”
Her words were having a profound effect on him, and he couldn’t help it. As much as he didn’t want to respond to them, he just couldn’t help himself.
“How did it feel to have Derek hold you in his strong arms as you were dancing? How did it feel when he hugged you so tightly when he said goodnight?”
Chad had no control of it anymore. He was pumping harder and harder, trying to feel more and more from the fake cock inside of him. He was being held and taken from behind by a living human body, and her words were sending images and feelings to his brain that he didn’t want to deal with in normal life. He was getting lost in her words and ideas and in all the many sensations. And it was building bigger and bigger, taking him further and further. Leading him towards…
“How did it feel when he pressed his lips up against yours and kissed you like he did?”
He could once again feel Derek’s soft lips pressing against his own, kissing him passionately. Derek’s strong arms were around him holding him tightly. He could again taste the thick lipstick on his own lips. He was helpless in Derek’s arms. Soft lips kissing his own. A man’s lips kissing his lips – like a woman…”
The strong almost cramping feeling may have begun at the base of his spine, but it quickly spread up and down throughout his entire body, from his toes to his fingertips. Even though Mel was still pumping in and out of him, he couldn’t move as all his muscles locked up tightly – then they suddenly started shaking – all of them! It felt like his whole body was straining in every direction at once. And the yell that finally escaped his throat was strained and high-pitched – and seemed to go on, and on, and on.
Mel was frightened at first, but soon her fright became amazement as she realized he was actually orgasming. She did her best to lean over and see just how bad his chastity device must be hurting him, but from everything she could tell, his trapped penis inside was just as tiny as ever – but there was liquid pouring out continuously from the device – and she could tell it wasn’t pee! Incredible! Incredible! Incredible! In many ways, she had just made him cum – as if he were a woman! A female! It was like stripping yet another layer of masculinity away from him. And as his own shaking started to come to an end, the added realization of what she had just done to him sent her over the edge one more time herself, except that this time, she was the one buried inside of him. She had no option but to pump harder in and out of him as she rode her own orgasm to its conclusion – which only caused him to keep pumping desperately in response.
It was a few moments before either of them could slow down – let alone settle down. It was an experience that Mel figured she’d never forget. She still didn’t believe it had just happened. Breathlessly, she slowly and carefully pulled her attached phallus out of him. She had taken him like a man – and he had responded like a woman!
Chad didn’t know what to think. He had finally had an orgasm… he thought. Although in truth he had never really felt anything like it – ever! Was it possible? He hadn’t thought so before, but now… Images of Derek kissing his lips again still swirled though his mind. He couldn’t stop them. He wasn’t even sure he wanted them to stop. Mel climbing off the bed distracted him enough to finally erase them from his mind – mostly.
Mel got down off the bed. She would have untied him, but she wanted to remove the crazy strap on device first and put something on to cover herself. As she was just starting to unbuckle the device, she heard a faint splashing sound. She looked over at him and saw a strong stream of pee rushing out of him again, splashing straight down onto the diapers protecting the bed below him. It puddled there a bit before starting to sink into the absorbent material. She smiled at the sight of it. In so many ways, it was hard to believe that he still had any control. Twice tonight she had seen signs that made her feel like she was winning this bet, but she knew better than to trust everything she saw. How long had he managed to hold back at work today? She had no way of knowing.
Chad felt so embarrassed as he realized he was peeing uncontrollably again. Actually, after what he had just experienced, peeing had been the furthest thing from his mind. Had he actually orgasmed? He was pretty sure. Yet the way it had happened – while feeling really great, had also been very embarrassing. What had happened to him? No, what was happening to him? Because the changes still seemed to be happening. But there was one other thought that seemed to lock onto his mind that he couldn’t shake – what he had once thought of as impossible, had just happened. It was possible! He had thought he could never orgasm that way, but he just had! But as his peeing came to an end, that thought led to one other thought – a very troubling thought. If the impossible was now possible, how about with their bet? He had thought before that Mel making him totally incontinent in only two months was completely impossible. But now? He still believed it couldn’t happen. Not at all. But… but now there was a tiny seed of doubt.
With her robe fastened tightly around her, Mel removed the ropes that held him in place. Then, while he was still on his hands and knees, she removed the scarf she had used as a blindfold on him. For no other reason than to be nice, she pulled away the wet diapers that were under him. “Roll over on your back,” she told him. “Let’s get you diapered again before you pee all over everything.”
Chad rolled gratefully to onto his back. He felt a mixture of pleasure, fatigue, and embarrassment. A moment later he felt a wave of frustration as Mel took out a jar of suppositories and shook it in front of him. “We can’t forget these,” she teased. She opened the jar and pulled one out. Chad turned his head away in disgust the moment he saw the capsule shaped pill. What Chad didn’t see though was Mel letting the suppository slip back into the jar as she put the lid back on. “Okay, raise up,” she ordered. Chad pulled his legs up high, exposing his bottom for her again. Mel stuck her finger way up inside of him – as if she were really sticking the pill up there. Once again, Chad never knew. But this was the second time today that his suppository had been faked. Her plan called for him to gradually get less and less as time went on now. But her big question was, would it make a difference? She could only pray that it wouldn’t. Just as she didn’t really know what kind of control he had over his peeing, there was no real way she could tell what would happen once she stopped the suppositories completely. And there wasn’t a lot of time left in this bet!
A short while later, clad in only the over-stuffed padding of four disposable diapers. Chad curtseyed one last time for her and gathered his things and took them home. Once again, Mel stared at the back of her closed apartment door after he left. Time was running out. Things always seemed to come down to time – precious time. Would she make it? Would she really do the things she bet him she could do? It had been a crazy bet from the start. A really stupid bet. She blamed it on too much beer that day. But the truth was, there was something else. Something else inside of her that must have realized she wanted to do this… maybe, needed to do this. But still, would she make it? She had to. She just had to! She couldn’t dare lose him. She didn’t want to contemplate what it would be like without him.

“Goodnight Sissy,” she whispered again. “Goodnight.”

The Bet - Chapter 45 (Monday – week 7 Part 6 of 7)

2011-12-20T02:56:00.000-08:00

The Bet
by Karen Singer

Chapter 45 (Monday – week 7 Part 6 of 7)

Sandy felt like she was letting Mel down. Besides, she absolutely loved watching Sissy make such a fool of himself – especially as a baby – so she guessed she was disappointed for herself. But tomorrow night was out. She and Cassie had plans and there was no way she could watch Sissy for Mel. Unless… Unless… She and Cassie were just going to visit some friends for the evening. What if they agreed to let Sissy come too? Now that she thought of it, the more she liked the idea – really liked the idea!
She picked up her phone and called Cassie to see what she thought, then she called one of her friends to get her opinion. No problem! Finally, she dialed Mel’s number.
Mel was just driving home from work when her cell phone rang. With one hand, she quickly dug it out of her purse and answered it. “Hello?”
“Hi Mel, it’s Sandy.”
“Hey Sandy. What’s up?”
“Did you ever find someone to take care of Sissy tomorrow night?”
“No!” Mel answered, totally frustrated with the problem. “Got any ideas?”
“Maybe one… if you’ll agree to it.”
Agree to it? That sounded fairly ominous. Especially knowing Sandy. But she was desperate. “What did you have in mind?”
“Well, Cassie and I are just going to visit some friends tomorrow night and… well… I thought that maybe Sissy could come with us.”
Mel wasn’t too sure about the idea though. “Don’t you think your friends will object to someone like Sissy being there?”
“Oh no! They’re very… open minded. In fact, they’re both a bit… wild!”
Wild? That shook Mel a bit.
“But don’t worry,” Sandy continued, “I already checked with them and they said they didn’t mind at all.”
Mel was still trying to contemplate what wild meant. But desperate was desperate! “Um… I guess it’s okay, as long as they don’t mind. But Sandy, the real reason I need someone to watch Sissy is to make sure he keeps wetting as much as possible. You know, like with the time limits I put on him. Do you think they’ll mind that too?”
Sandy giggled. “No problem! I already told them about Sissy. In fact, they’re looking forward to seeing him. But don’t worry, just because they’re a bit kinky, they’re still good people.”
Kinky? “Um… I’m sure they are,” Mel replied. But she also realized that Sandy had already been through and checked with everyone. “Then I guess I don’t see any problem at all. Especially if you can make sure he keeps to his schedule. In fact, I appreciate it a lot!”
“Great Mel!” Sandy replied enthusiastically. “And I was thinking, maybe we could even offer to let Sissy cook us all dinner too?”
That part didn’t really bother Mel in the least. “That’s fine. He seems to like showing off his cooking talent.”
Sandy laughed. “It’ll be great! I can’t wait to show him off in that silly baby dress to everyone… Oh, hey! Gotta’ go! Talk to you later!”
Mel was suddenly left with an empty phone connection. Sandy wanted him dressed in his baby dress? What kind of evening did she have in mind? She now didn’t know if she was worried… or if she wanted to be there just to share in the fun!

Chad glanced at the clock. Mel was running late. But more importantly, he was worried about how much time he had till his diaper had to be leaking. He already knew that Mel would be home shortly. He also knew he was going to get a beating tonight for taking his thumb out of his mouth earlier with Robin. He didn’t want to make things any worse by not getting his diaper to leak when it was supposed to. So he was drinking furiously from his third baby bottle now since he had gotten home.
He heard the apartment door opening and he rushed out and saw Mel just coming in. He curtseyed. “Welcome home Mistress,” he said in his sissy voice.
Mel smiled at seeing him curtsey and hearing his silly sissy voice. The aroma of something good cooking in the kitchen filled the apartment too. “Thank you Sissy,” she replied as she set her things down on the little table by the door. When she turned back again, Chad was hurrying away back to the kitchen. She followed after him. “Something smells good,” she said as she watched him hurrying to the stove where he grabbed a large spoon to stir something in a pot.
“Thanks,” he replied as he set the spoon down again. “Dinner will be ready in just a moment.”
Mel shook her head. “I’ll be adding five more swats to your punishment tonight for not curtseying before speaking to me just then!”
Chad was shocked. He had been busy cooking! And she still expected him to curtsey every time he opened his mouth? Ugh! He curtseyed now. “Yes Mistress,” he replied sullenly.
Mel noticed that the table was very nicely set already. “I’ll be right back,” she said to him as she turned and headed toward her bathroom.
Chad dished out her meal. But it was only a meal for one. He hadn’t bothered to make any for himself since she had declared that he would be eating mostly baby food from now on. There was a whole cabinet full of it that he didn’t even want to look at. Mel came back as he was looking everything over one more time to make sure he hadn’t forgotten anything. This time he remembered to curtsey first. “It’s all ready Mistress,” he said as he stood back.
Mel smiled and sat down. Everything looked so nice. The food smelled so good. All that remained now was… “Sissy, back to your perch!”
He had been expecting it, but he still hated to hear her say it. He quickly grabbed himself one more desperate swig from his latest baby bottle, then headed sullenly back to his little corner where he climbed up onto his perch. His body was pressed up against both walls. The only thing he could see was the blurry vision of the two walls. He closed his eyes and tried to concentrate on staying as still as possible. Back in his little corner. Back up on his perch. Back to being out of sight and out of mind. Back to being – bored!
Mel ate leisurely as she watched him up on his perch in the corner. Dinner was excellent! He wondered what he would be cooking for Sandy and her friends tomorrow night. Whatever it was, she had no doubt that it would be something good. He didn’t know about that yet and she wondered if she should tell him or not. She decided to keep it from him for now. It wasn’t something he needed to be worrying about – yet. And knowing Sandy, maybe he should be worried! Sandy wanted to show him off in his baby dress? Her friends where wild? Kinky? She had a lot of mixed feelings about that. But mostly, she was jealous that she wasn’t going to be there herself.

Bored, bored, bored, bored, bored, bored, bored! Boring corner. Oh! I’m peeing! Excellent! Yes! Feels great! Is my diaper leaking? Leak! Leak! Leak! Please leak! Nothing… yet. Got to pee again! Got to start leaking! Need more to drink, but I can’t if I’m stuck here in this boring corner. How long have I been here now? How much longer? Isn’t she done with dinner yet? Ugh! I’m tired of this. My calves ache! My toes are all scrunched and hurt. I want to move them. I need to move them. But I can’t move them. There’s just no way. Stuck! Ugh! Want to move but I can’t. How much longer? Need to pee again! Come on! Pee, pee, pee!

Mel got up from the table and opened the cabinet that now held all his baby food. There was a lot to choose from. She started taking down jar after jar to see what it was. Gradually, she built a suitable dinner for him as she set the jars she wanted down on the counter. She grabbed a plastic child’s plate from another cabinet along with one of his rubber coated baby spoons. Then she opened jar after jar and dumped out the colorful mush onto the plate. When she was done, she was tempted to mix it all together into one big mushy pile, but she didn’t.
“Okay Sissy. Get yourself over here.”
Chad gratefully pulled himself off of his perch and stretched his legs and feet before trying to walk. He was just glad to finally be out of the corner again. He was especially glad to finally be off of his perch again. By the time he got to the kitchen, Mel was holding the tray to his highchair in her hands and was waiting for him to climb up onto it. He headed for the chair, but he saw a sudden look of anger in Mel’s eyes. He stopped and curtseyed to her again. He was relieved to see her smile. Only then did he climb up into his chair. She pushed the tray into place, locking him into the chair. Then she tied a bib around his neck. She delivered his dinner to him along with the tiny baby spoon. And finally, she put his latest baby bottle down on the tray for him to drink from. He grabbed the baby bottle first because he had to meet his leaking deadline.
Mel poured herself another cup of coffee and leaned back against the kitchen counter to watch him eating as she often did. “So it looks like you’re not going to get fired after all?” she asked.
Chad stopped eating momentarily and sighed with relief. “It looks like it anyway. Robin said she didn’t tell anyone.”
Mel smiled. “That’s good.”
“She was just so angry at me!” Chad said as he dipped his little spoon into some orange colored mush.
“What did you expect?”
Chad shrugged before stuffing the colorful food into his mouth. The action made him miss a bit and some of it spilled down onto his chin.
Mel chuckled. Actually, it was the first food he had spilled so far.
“I was hoping it would go a little better,” Chad finally said as he dipped his spoon back into his food again. He suddenly looked up at her. “And where did this sticking my thumb into my mouth thing come from?” he asked.
That was the part that had surprised Mel too. Surprised, and delighted her. But she wasn’t going to tell Sissy that. “I don’t know,” she replied. “I honestly don’t know.”
Chad went back to eating – and wondering what had gotten into Robin.
“Tomorrow night,” Mel said, surprised that it had come out of her mouth because she wasn’t planning on telling him about it yet. “I have a date.”
Chad was a bit surprised. “With Ray?” he asked.
Mel nodded. “Yes. With Ray.”
Chad felt disappointed and hurt. But he stopped himself from feeling any worse. Why shouldn’t she go out with a proper good looking guy? Why shouldn’t she have some fun with a real man? Who was he to say what she should and shouldn’t do? She was a good looking woman. She deserved to go out with a real man… not someone like him. Yeah, like she would ever go out with him… a sissy! Looking only down at the food on his plate he replied. “I hope you have a good time.”
Was that… disappointment she heard in his voice? Interesting. “I hope we will,” she replied. “And… I hope you have a good time too.”
Chad looked up quickly. “Me?”
Mel nodded. “You’ll be going with Sandy and Cassie to visit some friends of theirs. From what Sandy said, it sounds like she wants you to cook dinner for them.”
Chad’s surprise turned quickly toward being very interested. Cook them dinner? What should he make? It would have to be something that he knew was really good that would show off his cooking ability. A little problem quickly arose. “Will they be coming here?” he asked.
Mel shook her head. “No. Why would you ask?”
“Because I don’t know what kind of food they’ll have, or what spices they have, or what kind of pots and pans and other stuff they have available. Maybe I should go shopping before then and get everything I need. Then I can just take it all with me. Do you know how many will be there?”
Mel shook her head. “Don’t worry so much about it. I’ll check with Sandy tomorrow and let you know.”
As Chad finished the rest of his meal, he barely noticed anymore what he was eating. His mind was more focused instead on what he could make them for dinner. He wondered if Sandy’s friends were worried about eating only diet food.

While Chad was busy cleaning up the kitchen after dinner, Mel changed into a pair of shorts and a t-shirt. Then she put her ballet music on again and started making notes about what things she wanted to choreograph for Sissy’s ballet. It was slow going, but she was making progress. Her biggest problem was that he knew nothing at all about dancing, and he was absolutely not graceful in the least. But she supposed that none of that was the point. The point was to create something to show off what a sissy he really was… or so she thought. Since she was creating this thing, there was a certain amount of pride in showing off what she was capable of doing.
She glanced at the clock. The time for him to be leaking was quickly running out. “Sissy! Are you leaking yet?” she called from the living room.
Chad had heard the ballet music on her stereo and knew that he would be spending some time dancing again tonight. But that wasn’t her immediate question. “No, not yet.” he replied somewhat forlornly. He was close. He knew he had to be very close. But so far this diaper was proving to be stubborn.
“Did you curtsey before you answered me?” she called back.
Chad could have screamed! “No,” he replied once again with even more disappointment.
“How about then?” Mel asked.
Chad wanted to kill himself. This time he curtseyed, then replied. “No… but I just did then.”
“I’ll add ten swats to your punishment tonight. Better hurry up, your leaking deadline is getting awfully close!”
He knew it. He knew it all too well. There were still a few pots to finish cleaning, but he ignored them in favor of doing nothing but drinking from his latest baby bottle. Pee! Pee! Leak! Leak! It was impossible to try to pee any harder than he was already doing. It seemed like his whole life lately was dedicated to doing just that. With Mel around, it never let up! He briefly wondered about tomorrow night. Hopefully, he wouldn’t have to worry about it tomorrow night at all. That would be a blessing!
He suddenly felt himself peeing yet again. He spread his legs hoping it would help matters, but unfortunately he felt nothing leaking. He glanced at the clock – two minutes left. Pee! Pee! Leak! Leak! But he had just finished peeing. He finished his bottle and quickly grabbed a fresh one out of the refrigerator. He drank furiously from it – just as he had with his last bottle. And miraculously, he felt a tiny bit of pee coming out once again. Leak! Leak! But nothing. It had been too little. In frustration, he began pacing around the kitchen while he drank from his bottle. One minute left. But then he felt something a bit odd. Wetness? He really wasn’t sure. He felt down around the bottom of his diaper and right at the leg opening on one side it felt a bit – wet. Yes! “I’m leaking!” he called out victoriously.
Mel glanced at the clock and saw the second hand tick down to the final second. She smiled. “Did you curtsey?”
Chad really wanted to kill himself.

Chad leaned over and put his arms up against the back of the chair. His totally naked bottom already made an inviting target for the thick yardstick she was holding at the ready in her hands. But it wasn’t what she wanted. Not what he had to do. He had no idea how many times she was planning on hitting him. Fifteen for sure, plus… a bunch more probably. Hating having to do it, he purposely raised his naked backside up even higher, making it the perfect target for her cruel stick. The swish of the stick moving through the air was faster than usual. Smack! Ouch! She had really hit him hard! Wow! With is backside stinging horribly, he stood up and curtseyed. “Thank you Mistwess,” he said in his sissy voice. It was a horrible thing to keep thanking her like that for hitting him. But… what choice did he have? He leaned back over against the chair again and raised his backside up into the required position. Swish… Smack! Ouch!
“You know Sissy,” Mel said as she waited for him to stand up and curtsey again, “one way or another, we’re going to teach you to curtsey politely at the drop of a hat.” She waited while he went though his little ritual and started to get back into position. “One way or another…” Swish… Smack! “We’re going to get you so accustomed to curtseying that you’ll be doing it without thinking anymore.” Again she had to wait while he curtseyed and thanked her. “You’ll be doing it before you do anything!” Swish… Smack! “If I have to, I’ll have you curtsey to every door before you open it… every little thing before you even touch it!”
Chad tried his best to digest that as he once again stood and curtseyed to her. “Thank you, Mistwess,” he said in his sissy voice again. But the shake in his voice was almost as much from the things she was saying as much as the pain he was feeling. He was so preoccupied by worrying about the next upcoming blows from her stick, and with what she was saying, that he didn’t even notice when he started peeing again as he leaned forward to brace himself against the back of the chair.
Mel smiled as she saw the golden colored liquid squirting out from his chastity device. “Well at least that’s one less thing we’ll have to beat you for tonight,” she said just before she swung her stick again.
Chad wasn’t even sure what she was talking about, and he thought even less about it as the sharp stinging blow to his backside registered immediately with his brain, wiping out all other thoughts.
Fifteen strokes, fifteen curtseys. All for not curtseying before he spoke – and each time had been when she wasn’t even in the same room with him. He was just glad to get them over with. His backside was on fire!
“Okay, that was the easy part,” Mel said as he finished his last curtsey and thanked her.
Chad wondered what she meant by that. He certainly wouldn’t have called that easy!
“Now we have to punish you for not following Robin’s instructions.”
He knew it was coming, unfortunately, he just didn’t know what Mel planned on doing about it.
Mel pointed toward the back of the chair again, and regretfully, Chad got back into position.
“Since this is going to be a lot…”
A lot? Chad started to get alarmed.
“…then just stay there like that till I decide to take a break. Then you can curtsey and thank me.”
Till she takes a break? A break? How many times was she planning on hitting him? And he already hurt!
“You’re going to learn that when a woman tells you to do something – make that when anyone tells you to do something – especially a woman – then you had better do it – exactly like they tell you to! Ready?”
Ready? Of course he wasn’t ready! What was she planning? Before he could think any more about it, she swung her stick – hard again. And before he could even fully react, she was swinging again, and again, and again. Over and over again as fast as she could, she pounded away on his backside with her stick. And the pain from it grew, and grew, and grew!
Mel swung fast and hard, but she was carefully controlling herself. Yes, she wanted to hurt him, but not like she would if she had lost control. Over and over again she hit his bare bottom, making sure to cover every inch of it on both sides. Very quickly, it grew from a warm rosy red to a very deep dark red. Finally she paused. “You can thank me now.”
Chad had no idea how many time she had hit him, it had hurt so much that it seemed to go on forever. He had been crying a little and fighting the tears before she had started, now he was bawling full out. He stood painfully, turned to her and curtseyed. But the words that came out of his mouth around his sobbing weren’t completely recognizable. Fortunately, Mel didn’t seem to notice.
“That’s one,” Mel said and pointed towards the back of the chair again.
One? One? He couldn’t believe it. She wasn’t done with him? He looked at the back of the chair and hesitated. He didn’t think he had the courage to lean back against it again for more punishment. But his hesitation only cost him another stinging slap from her stick against his leg. Quickly, he found himself back in position again awaiting the next part of his beating. Once again, Mel flailed away at him unmercifully while he cried, and cried, and cried. Finally she stopped. He was still leaning against the back of the chair, but he couldn’t move.
“Are you going to do as you’re told from now on?” Mel asked.
Still leaning against the back of the chair, he nodded his head vigorously and tried to say, “Yes.” But the moment he did, she was back hitting him again. Five more quick swats of her stick.
“That was for not curtseying before you spoke again!”
Chad curtseyed again, but he didn’t even try to speak. He was crying too hard. Three minutes later, he was laying face down on the carpet on top of a fresh diaper while Mel was gently applying soothing lotion all over his dark red backside. The lotion felt frigid cold and stung as soon as it touched him, but it quickly warmed up. Even though she was only lightly touching him, her hand still felt all too painful as she rubbed the lotion all over his bare skin. He hurt so badly that he was glad when she finally finished and he could roll back over so she could finish diapering him again. And once again, he was working on another hour and forty-five minute time limit.

Chad stood in the middle of her living room, fully dressed once again. He had expected to be practicing ballet again tonight, but it seemed that Mel had other ideas. Ideas that he was not all that fond of. Mel had been working with him for the last fifteen minutes trying to craft just the right kind of apology for him to give to Robin tomorrow. It wasn’t that it was all that much or all that difficult. It was just that it was… embarrassing! But then, wasn’t any kind of apology embarrassing?
“I think that will work,” Mel declared from her seat in the living room. “Let me see it now one more time.”
Chad curtseyed to her immediately – he dared not even think about doing anything without curtseying first. Then he paused for a moment to get ready. He reached down and grabbed the hem of his skirt and dropped into as nice a curtsey as he could, spreading his skirt as wide as possible. He bowed his head momentarily, then rose again putting his feet together and clasping his hands contritely in front of him. “I’m sorry Robin,” he said in his sissy voice, “that I didn’t do exactly what you told me to do yesterday. I promise not to give you any more trouble and to do whatever you say from now on.” Then he dropped into an identical curtsey to the first one again and stood back up. He looked to Mel for her approval and curtseyed quickly to her once again as he did so.
Mel smiled. “Yes, I think that will work nicely. It’s not too extravagant and I think it sets just the right tone. Don’t you?”
Of course all Chad could do was to curtsey again and agree with her.
“Good, now do it again.”
Once again, Chad had to go through the little routine, followed by another practice run, followed by another one. Finally, Mel dismissed him to go finish another bottle while she went back to work on making notes for his ballet.
Chad hurried into the kitchen where his latest bottle was, and immediately put it to his mouth and started drinking. Her stupid little apology routine wasn’t very difficult, but it sure made him feel foolish as he did it. Of course, when he did it for Robin tomorrow – ‘if’ he did it for Robin tomorrow, then he wouldn’t be using his sissy voice. His girly voice wouldn’t be quite so humiliating.
He finished his bottle and was just opening the refrigerator to get another one when Mel called him back into the living room again – to practice the routine five more times.

The Bet - Chapter 45 (Monday – week 7 Part 5 of 7)

2011-12-16T02:54:00.000-08:00

The Bet
by Karen Singer

Chapter 45 (Monday – week 7 Part 5 of 7)

Mel was actually at her desk when she saw Chad’s email come through. She read it with great interest – twice. Finally! Things were happening there. And best of all, it was sounding like Robin may not have told anyone yet – not where she worked anyway, which was all she cared about.
She started to write back to Chad, but before she could get started, she was reminded of the odd thought she had that popped into her brain earlier in the day. Was it possible? Would it be possible? There was only one way to find out! Instead of writing what she had planned on writing to Chad, she sent him a reminder to continue to do whatever Robin wanted. Then she asked him to send him Robin’s email address. Two minutes later, she had it. Very carefully, she crafted an email to Robin.

Robin couldn’t believe it when her email notification popped up and showed that she had an email from Mel. What did that crazy woman want now? She opened it and read it.

Dear Robin,

Did you know that Sissy is under orders to do whatever you tell him to? And if he doesn’t do exactly what you say, then I want to know about it!

Call or email me if you want.

Mel

Robin read her note with disbelief. The woman was crazy! She wasn’t about to get drawn into their weird little games! She closed the email faster than she had opened it. But she couldn’t go back to work. Instead, she brooded about what a jerk Chad was. And over and over again, just as she had seen it in her mind all weekend long, she kept picturing him in that highchair, covered in baby food, acting like an infant! The stupid perverted idiot!

Chad stared at his computer monitor – without seeing it. He was more concerned over whether Robin intended on telling anyone about… him… or not. Did he, or didn’t he have to worry about being fired?
Finally, he couldn’t take it anymore. Despite Robin telling him she didn’t want him to talk to her, and despite Mel telling him again to do whatever Robin wanted, he got up from his seat to see her. He had to know! He stopped at the entrance to her cubicle. She was just sitting there with her head in her hands. “Robin,” he said quietly.
Robin turned angrily at the sound of his voice. What did she have to do to get the point across? She didn’t want to talk to him!
“You didn’t tell anyone?” he asked.
She was out of her chair before she even knew it. “Didn’t I tell you not to talk to me? What do I have to do to get you to understand that? I don’t want to hear your stupid voice anymore!” She paused, but only for a moment. “And just for your information, no, I didn’t tell anyone. Nobody at all! Your crazy friend Mel said that it was your biggest secret. The one thing you didn’t want anyone to know about! So why the hell did she tell me? You can think what you want about me, but some people are more trustworthy than others. No! I didn’t tell anyone about you and your… perverted interests! Not yet anyway. Now get the hell out of here!”
She actually shoved him again as she said it. Chad backed off quickly and hurried back to his own cubicle. Well, he had to know. And best of all, it sounded like she wasn’t going to divulge his secret – not yet at least. He actually breathed a small sigh of relief.
Robin again stared angrily at her computer screen, but like before, all she saw was the image of Chad in that silly highchair acting like a stupid baby! The idiot! And he wanted to know if she had told anyone his secret? His deepest, darkest, most perverted secret? What did he think she was? The idiot! The stupid, perverted idiot!
And then his… mistress… what a laugh!... had the gall to send her a note telling her that he has to do whatever she tells him to do? He can’t even keep quiet after she told him – repeatedly – not to talk to her! It was like talking to a three-year-old – you had to tell them things and tell them, over and over again. No, not quite like talking to a three-year-old. A three-year-old had more sense!
He wanted to act like a baby? He had to do whatever she told him to? Well… she knew how babies acted, she had one of her own! And if he was so insecure about everything, then she knew just how to deal with that!
Determinedly, she got out of her seat and marched straight back to his cubicle. “You like acting like a baby?” she announced more than asked.
Chad turned around, totally surprised to see her again so soon.
“Then stick your thumb in your mouth! And suck on it!” she ordered. “That’s what insecure little babies do, they suck their thumb!”
Chad was totally shocked. So much so, that all he could do was to stare at her in disbelief.
Seeing that he wasn’t moving, Robin added. “Your… mistress!” she spat the word, “tells me that you have to do anything I tell you to! So stick your thumb in your mouth and suck on it!”
Still not believing it, Chad slowly raised his left thumb and stuck it in his mouth. Mel had told her he had to do whatever she asked? Was it possible? Well, Mel had asked for Robin’s email address. He just hadn’t expected anything like this.
“I said suck on it!” Robin yelled angrily when she saw that his thumb was only resting in his mouth. She saw him start sucking. “Harder!” she ordered. “I want to see your cheeks going in and out!” A moment later, she felt better about things. It was as if she had physically hit him to vent her rage. “Now keep it there,” she added. “Maybe that will make sure I don’t hear another sound out of you for the rest of the day!” With that, she turned and walked off!
Chad stared at the empty entrance to his cubicle. She had ordered him to suck his thumb! He still couldn’t believe it. Where had that come from? He was so shocked, that he sat there like that for several minutes before he slowly turned around again and took his thumb back out of his mouth. He couldn’t believe it! As per Mel’s orders, he opened his email program again and started to write about what had happened.

Feeling a bit more satisfied, Robin had almost worked up the nerve to do something other than brood, when she heard the faint sounds of him typing in the next cubicle. And it bothered her! How could he type like that if he had his thumb in his mouth? He couldn’t!
In a flash she was out of her seat again and back at his cubicle. He was typing – with both hands! “Damn it!” she yelled. “It is just like talking to a child. You have to keep after them and after them! Didn’t I tell you to keep your thumb in your mouth? What do I have to do, stand you in the corner too?”
Wide eyed, Chad stuck his thumb back into his mouth again and sucked on it hard like she wanted him to. Robin watched him for a few moments, feeling satisfied once again. But then she thought of something else. “Wait a minute! You’re right handed. Put your right thumb in your mouth instead!” She watched as a disbelieving Chad slowly switched hands – and started sucking just as hard on his right thumb now. “Better!” she declared with more satisfaction.
But Chad had a problem now. How was he supposed to type? How was he supposed to work? He pointed toward his keyboard and his monitor, hoping she would understand his question.
Robin smiled. Her voice sounded almost kind. “How are you going to work?” Her voice changed to angry command again. “You still have another hand. Use it!” She turned and started to stomp away again, but she paused and turned back to him. “I’ll be back to check on you. Obviously you can’t be trusted to follow simple directions – just like a child!” She left him then, and returned to her seat, where she reopened the email from Mel and typed a very short reply - He doesn’t follow orders very well, does he!

Chad hunted and pecked with his left hand at his keyboard. Using the mouse was even more awkward. He had to reach across his body to use it, and then the buttons on it were in the wrong place for his left hand. He was careful though to keep his right thumb in his mouth. He didn’t suck on it as hard as Robin wanted him to, but he doubted she would see that as long as his back was to her. Very slowly he continued his email to Mel.

It was a little while before Mel got back to her desk and found both emails waiting for her. She wasn’t sure which one to open first. She opted for the one from Robin because it had come in first. What she read surprised her greatly. He didn’t follow orders? Had she told him to do something? She was about to reply, but she decided to read the one from Chad first – and she was glad she did. When she was done, she sat back in her seat to think about things.
Robin had actually ordered him to suck his thumb? She couldn’t believe it. Did that mean… No, it was too much to hope for. But still, it might be possible. She opened up Robin’s email again and hit the Reply button. She had to be very careful about this. The wrong move or the wrong word could spoil everything. Best to keep it short and simple again.
She wrote – Expect a “proper” apology from Sissy tomorrow. As always, feel free to call or email me.
Then she sent another email to Chad!

Chad had to reach awkwardly across with his left hand to open the email from Mel when it came in. What really surprised him about it was that Robin had obviously emailed Mel first – and told her that he hadn’t exactly followed her orders. The rest of it was only what he expected – be prepared to be punished severely for it. Ugh!
“Turn around!”
The command came so suddenly and unexpectedly that Chad had no time to prepare for it. He quickly turned around in his seat and saw Robin standing at the entrance to his cubicle. Fortunately, his thumb was still in his mouth. He started sucking furiously on it, making sure his cheeks were moving in and out as he did so – just the way she wanted them to.
Robin saw him still sucking his thumb – hard again. Although she doubted he had done much more than keep it in his mouth while she wasn’t there. She walked over and looked at the email message still up on his screen. It was from Mel. She read it. “It sounds like you’re going to get… what? A beating tonight? I hope so! I can’t think of anyone who deserves a beating more than a stupid pervert like you!” She headed back out of his cubicle again, but stopped at the entrance. “I’ll be checking, so keep that damn thumb right where it is – and suck on it so I don’t have to hear your whining voice about anything!”
She walked off leaving him alone again and went back to her own desk. She couldn’t believe it! The jerk! He was actually still sitting there sucking his thumb – like she had told him to. Well, he better be! She wasn’t in any mood to be nice today at all! And there was a certain feeling of… satisfaction… in ordering him about – and actually seeing him do it! As long as she kept watch on him, she guessed. Ha! Just like a child indeed! She wondered how much trouble Mel had with him. And… she wondered why she should even think such a thought.

It wasn’t that Chad minded sucking his thumb so much, it was just that having to keep it in his mouth all the time made doing anything very difficult. He tried to get some work done – not that there was all that much he had to worry about – at least not today. But actually getting anything accomplished was very difficult. He hoped nobody came down to his cubicle to see him today – like Tom Robinson, his boss! That would be embarrassing!
It was kind of strange, sitting there, sucking his thumb, while at the same time trying to notice every time he had to pee and try to hold back as much as possible. It was like two distinctly opposite things going on at the same time. And when the miserable suppository that Cassie had stuck up inside of him at lunchtime decided to do its thing, all he could do was to stand up to make the process go easier and faster – and suck his thumb all the harder while it happened. Ugh! At least Robin didn’t come back while it was going on. What would he have said? Oh yeah, nothing. She didn’t want to hear anything out of him today at all.
But shortly after he had “managed” to sit back down again, Robin did come back. “Turn around!” she ordered from the entrance to his cubicle.
Chad hadn’t heard her coming again, but his back was still to her. He started sucking hard on his thumb again as he turned his chair around, wondering what she would want now. But all she did was to look at him, nod her head, and leave again. He couldn’t believe it, she had been there for no other reason than to check on him. As he turned back around to face his computer, he knew that until she told him otherwise, his thumb was going to have to remain stuck in his mouth – or until he went home.
Twice more Robin made an appearance at his cubicle, for no other reason than to make sure his thumb was still in his mouth. The first time, she merely nodded her head and left again, the second time she shook her head and muttered. “Just like dealing with a child!” And again she was gone.
As the time got closer and closer to the time to go home, Chad began to wonder what he was supposed to do when work ended. Did Robin expect him to walk out with everyone else while he was still sucking his thumb? She had a big surprise coming if she did – because he wasn’t about to go that far!
As the work day drew to a close, Chad got up from his seat with his thumb still in his mouth and got his purse out, ready to go. He watched the clock as it ticked away the final few minutes. With less than a minute left to go, Robin was back one more time. She stopped at the entrance to his cubicle, her things were already in her arms. “Stay there with your thumb just like that till I’m gone! That way I don’t have to worry anymore about seeing you without it in your mouth!” And then she left. Chad sat back down again as if stunned. What a day! What a weird day!

The Bet - Chapter 45 (Monday – week 7 Part 4 of 7)

2011-12-13T02:51:00.000-08:00

The Bet
by Karen Singer

Chapter 45 (Monday – week 7 Part 4 of 7)

Mel had only marginally enjoyed the lunch with Ray. The restaurant had been too hurried, too noisy. There had been no way to really enjoy it. Not to mention the awkwardness of some of the conversation. She was looking forward to her date with him tomorrow night, but she also worried he would ask more questions about her relationship with Sissy. That thought reminded her of her other little problem. What was she going to do with Sissy during her date? There was absolutely no way she could leave him alone without someone making sure he was wetting his diapers on time.
Her phone suddenly rang and she pulled it out to answer it. “Hello?”
“Hi Mel, it’s Cassie.”
“Hi Cassie. How did it go today?”
“Just like usual. I pretended to put that thing up inside of him again and he had no idea that I didn’t.”
“Good. I just hope it’s working!”
“So far, everything seems to be looking that way.”
“Yeah, so far. But will it stay that way?”
“I guess we can only hope. Hey Mel, I just wanted to let you know that while I was cleaning up his front side, he started peeing again…”
“I hope you didn’t get wet!”
Cassie laughed. “No worries, I caught it in time. But I just wanted to let you know that when it happened, he had no idea that he was doing it till I grabbed his diaper and had to pull it back over him.”
That was good news to Mel. “So he really didn’t seem to know it?”
“Not as far as I could see.”
“Great Cassie! Thanks!”
Mel hung up her phone. Cassie’s news was all good – and just what she was hoping for. But now she was still stuck with what to do with Sissy tomorrow night. But Cassie’s call reminded her of Sandy – and her offer to babysit with him any time she needed it. Sandy would be perfect! With a smile, she called Sandy. “Hi Sandy, it’s Mel.”
“Hey Mel. What’s happening?”
“I was just wondering if you were available to babysit with Sissy again?”
“You know I’d love to. Tonight?”
“Uh… no. Tomorrow night.”
“Oh gee Mel. Tomorrow night Cassie and I have plans. We’re going to visit some friends. I can’t do it.”
Mel could actually hear the disappointment in Sandy’s voice. She was disappointed too. “That’s okay, Sandy. I’ll figure something else out.”
“What’s going on tomorrow night?”
“I’ve got another date.”
“Good for you! Listen, Mel. You know I’d really like to help. But it’s just that, tomorrow night isn’t good for us.”
“Yeah. No problem Sandy. Thanks anyway.”
Mel hung up her phone again. Darn. Sandy would have been the perfect solution. Now what was she going to do?

Chad sat dejectedly at his desk and stared at his computer screen. But he wasn’t working. He wasn’t getting anything done at all. As far as he could tell, Robin still wasn’t talking to him… although he really hadn’t gone to her desk to even try. He just didn’t feel that brave. How much longer before his boss would call to fire him? It was only a matter of time.
He suddenly realized that he had to pee again and caught himself just as it started to release – automatically. He held it back, but only with great effort. But since it had already started coming out when he tried to stop it, the effort to hold back now was more than he could manage very long. With a sudden expulsion of his breath, he gave up and let it all loose.
He had to start trying harder to hold back! It had been another unbelievable weekend. Mel had been at him with her wetting requirements harder than ever. And today he had been so worried about Robin and his job that he had hardly bothered trying to hold back at all. Whether he lost his job or not, he still wanted to win this bet. It had gone so far now that there was no way he was going to back out – which would amount to the same thing as losing. Losing was simply not an option!
Disgusted with himself for not working harder at winning, he minimized the program on his computer. He could just barely hear Robin typing in the next cubicle. Feeling safe enough, he opened his spreadsheet for tracking the bet. He found today’s date and noticed that there were still eighteen days to go. Two and a half weeks. The number was down in the teens now which seemed like a major milestone, but today it still felt like an eternity.
He moved up to the date for last Friday. How long had he held back then? He wasn’t really sure at all, but something in his brain seemed to remember eight minutes. But was it? He filled it in, just because he thought it was correct. But how long would he manage to hold back today? He had a feeling that making only eight minutes again wouldn’t happen. Weekend’s with Mel seemed to take way too much of a toll on his system. But all he could do was to try – and try hard!

Robin glanced at the clock. There was still a little time before break. The others all wanted to see Sissy at break today, and now that those pictures had been spread around, she knew there was no way that Sissy would be able to avoid going – whether he liked it or not… and she really hoped he didn’t like it!
But should she talk to him again? Now? No, she just didn’t feel like it yet – if ever! Let him stew for a while. Besides, she didn’t know what she would say to the jerk anyway. The sick pervert!

Chad sat at his desk and pretended to work. He watched the clock. He still hadn’t received any notification yet about being fired. He wasn’t sure if that was a good sign or not. It could still come at any time. The clock changed again. Break time – or… it would be… normally. Robin had told him not to go earlier, and since nothing had changed, he had no doubt that not going now was his best course of action.
“Sissy!” Robin’s voice spat angrily from the entrance to his cubicle.
Chad turned around totally surprised. Was she speaking to him again?
“You’re going to break! Get moving!”
Just that. No niceness about it. Just an order. But at least it was something. He got up quickly from his chair to follow her. He wanted to tell her how sorry he was. “Robin…”
“Shut up! I don’t want to hear your sick voice at all! Just don’t talk to me! Ever!”
Stung, Chad followed quietly behind her all the way to the break room. Robin never once even glanced in his direction the entire way through the halls. But now Chad was starting to get more worried about what the other women would say. He was sure that Robin had told them during the morning break about what she knew. There was no way that she couldn’t!
They entered the break room and Chad started to follow Robin towards the coffee pots, but he really didn’t want any coffee, not today. Besides, more liquid in his system wouldn’t help him with – other things. He stopped and stared at the table that was already getting filled up with women. He didn’t want to go there either. He glanced around the room. Derek certainly wasn’t there, Derek was away for the week. He saw no other refuge he could go to.
“You’re not getting coffee?” Robin asked, seemingly pleasantly.
Chad was a bit startled by her question and how nice it had sounded. “No…” But that’s as far as he got before the quick flash of anger on Robin’s face stopped him. Without saying a word, he headed for the coffee.
“Hi Robin,” one of the women said as she passed them after getting her own coffee.
“Hi,” Robin returned very pleasantly.
“Hiiii Sissy,” the woman said to Chad.
But it was the way she had said it that startled him – and worried him. And what was that weird look in her eyes? “Uh… Hi,” he returned cautiously.
He waited while Robin got her coffee, then he filled his own cup and followed her towards the women’s table.
“Sissy!” One of the women called out excitedly. “Hurry up and get over here girl!”
As Chad approached the table, one of the women pulled out an empty seat for him. He noticed that all eyes were firmly on him. Obviously, Robin had told them everything! He felt like a lamb being sent to the slaughter as he sat down.
“Now we want to know all the details!” One of the women said excitedly. “And don’t leave anything out!”
All the details? What was he supposed to tell them? That he had this weird quirk?
“Those pictures were great!” another woman said. “And that kiss!”
Pictures? They had pictures? And the kiss? And then it dawned on him, the date! The pictures that Ray had taken. They weren’t talking about his bet with Mel at all. They all wanted to know about the date. Maybe Robin hadn’t told them – as hard as it was to believe. Open mouthed with surprise, he asked, “You have pictures?”
“You mean you haven’t seen them yet?”
Chad shook his head. “No.”
“Oh, they’re real good!” the woman replied.
“Real good!” another woman echoed.
“I just wish I could see your dress better,” another woman said. “None of the pictures show the front of it very well. Did you get it just for that date?”
“Uh… Yeah,” Chad replied, still trying to come to grips with the fact that they just wanted to know about his date last night. “I liked it when I tried it on. It was comfortable too.”
“So did Derek like it?”
“Uh… I guess so.”
“Men!” another woman added. “They never mention anything important!”
“Well,” Chad added, “He did say he appreciated how I had dressed.” He didn’t add that Derek had been comparing it to the outfit he had worn to the poker game.
“Then he did like it!” the woman replied. “Actually, I think that’s more than you can get out of most men!”
“So how about the kiss?” another woman asked. “Were you expecting it?”
Chad wasn’t sure how to answer. He nodded. “Kind of,” he finally replied. Again, he didn’t add that it was part of the bet between Derek and Ray from the poker game.
“And you got one! And from the looks of things, it was a good one! Tell me, how was it – really?”
Ugh! What a thing to talk about! “Um… “Surprising. I wasn’t expecting anything at all like what he did.”
“And you keep claiming you’re not getting a sex change just to be with him!” One of the women teased.
“I’m not!” Chad protested. But most of the women just laughed.
Robin sat back and said nothing at all as the questions continued. Actually, she was just as caught up in the details of his date as the rest of them, she just refused to show it. The jerk! How could he ever agree to do something so stupid as what he was doing? And all for… a bet? Dumb! Dumb! Dumb! And… sick!
The women started to leave and Robin got to her feet. She saw Sissy do the same. In a group of women, they headed for the door. She could still hear some of them asking questions to Sissy, and he was still trying to give out only little details. Idiot! Once they were through the door and out into the hall, the tangle of women broke apart, and one hall later, she and Sissy were alone.
“Robin…” Chad began.
“Shut up you idiot!” she spat back quickly. “I told you not to talk to me!” The fool! Did he think everything was going to be just fine and dandy between them now? The idiot!
Chad followed her silently all the way back to his cubicle. She stopped at the entrance.
“Don’t talk to me!” she said angrily again.
Sullenly, Chad entered his cubicle and headed for his seat. But before he could sit down, she was talking again – or more like yelling.
“What the hell is wrong with you?” she asked.
Chad turned quickly, his eyes wide with surprise. He had expected her to just leave. But before he could say anything, she was on top of him and pushing him roughly back into his chair. “But…”
“I said shut up!” she screamed. “What the hell is wrong with you? Do you know how stupid that idiotic bet of yours is? You pervert! You stupid, stupid pervert! Signing your life away – throwing your life away! For what? Some silly furniture? Idiot! Idiot! Idiot! You disgust me!
“And you actually want someone to boss you around like that? Make you do the most idiotic things imaginable? You’re sick, sick, sick! And you like it? You like it? That’s the part that really gets me! You actually not only like it, but you want it! You want that bitch to push you around like you’re nothing! Make you do things like… like… I don’t know what! Stupid! Stupid! Stupid! Sick! Sick! Sick!
“When you kept saying that it was complicated, I never really believed you. Well, I believe you now! And I wish to God I never heard of you!”
Robin backed off for only a moment – just enough time for her to catch her breath before launching back at him again.
“She invites me over – the bitch! And I think, wow, wonderful, I’m finally going to get to find out what’s going on. And then she shows me that contract you signed – not only signed, but had notarized! Are you crazy? Well, we’ve established that much already. And then I read what’s on it, and I thought it had to be a joke. Some kind of sick, sick joke! But it wasn’t! You actually want her to do this to you. You actually want to be some kind of a… a… sick, sick slave or something!
“And then she starts telling me you want to be a baby! Damn! You idiot! You actually want to wet your pants everywhere? I can’t believe it! I certainly didn’t want to believe it then! So she takes me over to… that place! And I see you… Sitting in a damn highchair for heavens sake! Covered with baby food everywhere. Wearing some kind of silly dress!
“You idiot! Idiot! Idiot! You’re nothing but a sick pervert! A sick, sick, pervert! So just… stay away from me!”
With that, Chad watched her turn quickly and stomp out. He was relieved she was gone. She had finally had it out with him. He was glad she had ordered him not to speak, because he really didn’t know what he would have said.
Well, he guessed he should tell Mel about it. He was sure she would want to know. He opened up his email program and wrote to her. He also mentioned that he wasn’t sure anymore if she had told anyone about their bet or not. When he finished, he closed the email program again. Now he was stuck to ponder the big question – did she tell anyone? The women in the break room didn’t seem to know about it. They were only interested in his date with Derek. But how about anyone else? And, more importantly, was she planning on telling anyone else? Did he still have to worry about being fired?

The Bet - Chapter 45 (Monday – week 7 Part 3 of 7)

2011-12-09T02:48:00.000-08:00

The Bet
by Karen Singer

Chapter 45 (Monday – week 7 Part 3 of 7)

Ray sorted through the pictures he had taken last night. He had sent them all on to Mel, but now… Now, it was just a shame that Derek wasn’t here this week. It really wasn’t as much fun, making fun of someone when they weren’t there – to receive the “benefit” of all his trouble. But, unfortunately, timing was everything. He selected one of the pictures of Derek kissing Sissy. One of them dancing together. One of them with the dessert for two between them. And finally, one of them holding hands together on the way out of the movie. He had more, but he was sure that these would be enough.
Now, who to send them to? Robin, of course, and he finally selected three other women from around the company that he knew would “spread” the gossip. Perfect. One click later and the pictures were sent. Now all he had to do was to sit back and listen to the office chatter. Poor Derek. It really was such a shame that he wasn’t here.

Robin cruised straight past Chad’s cubicle as she returned to her desk. She only noticed out of the corner of her eye that he was still in there. She still didn’t want to talk to him… if she ever talked to him again! Unfortunately, because of the other women in the company, she was going to have to – eventually.
She sat down at her desk and noticed that she had some emails. One of them was from Ray. What did he want? She opened the email – and was shocked to see a picture of Sissy kissing Derek! She didn’t quite know what to think about that. Then she realized there were more pictures in the email. As much as she didn’t want to look at them, she couldn’t not look. Last week, before she knew what was really going on, she would have swooned over the pictures and had a ton of fun with them. But now? Obviously, Sissy had had an interesting date Sunday night. Obviously! She just wasn’t sure she wanted to know any more about it.

Mel finished up with her client and immediately checked her email again. No message from Chad. No calls either. She didn’t know if that was good or bad. There was also the possibility that Robin was yelling at him right then and he hadn’t had time to write to her yet. But she figured that more likely, things were quiet where Chad was.
Knowing she shouldn’t put it off any longer, she sat down to write to him.

Sissy,

I doubt that Robin will continue avoiding you forever. I think you should be prepared for the fact that she’s probably going to be pretty upset at you and will probably show it. So be prepared to be yelled at… at least!

One more thing – and this is important! If she tells you to do something, then I suggest you follow her wishes and respect her needs. I can see several possibilities there. She may want you to explain more about what’s going on, or she may just want you to shut up and not say a word. Who knows? She may want something else entirely! I recommend you do whatever she wants and just let her vent. Just keep me informed as soon as possible.

Chad read Mel’s email and shook his head. Why did she even bother sending it? He was more than sure that – eventually – Robin would speak to him. And he was also fairly sure that Robin wasn’t going to exactly be nice to him when she did. And what else was he supposed to do except shut up if she wanted him to be quiet or to try to explain if that’s what she wanted instead. Dumb instructions! But at least he knew that Mel was watching and that she cared. That in itself was fairly comforting.

Ray stood outside the restaurant and waited for Mel to show up. He finally saw her arrive and pull into an empty parking space. He had to wonder about her. She was a lawyer, so she must make pretty good money. She drove a real nice car. So why didn’t she live in a more upscale place? Well, maybe it would make good conversation for lunch. He smiled as she came running up.
“Hi!” Mel said breathlessly. “I’m so sorry I’m late. Clients can be so… frustrating sometimes.”
“Don’t I know it,” Ray replied as he politely held the door to the restaurant open for her.
The restaurant was packed, but they still got a table right away. Wait staff were hurrying everywhere trying to take care of customers as fast as possible. Before they had a chance to start talking, a waiter was there to take their drink order. Since everything seemed so rushed, they each picked up a menu and read through it quickly before saying anything to each other. The waiter was back quickly with their drinks and they each ordered something light off of the menu. The waiter departed just as fast as he had arrived.
“So where would you like to go tomorrow night?” Ray asked as he leaned forward across the table.
Mel wondered if the look in his eyes was hunger for some lunch, or her.
“I don’t know. Surprise me!”
Ray smiled and started to lean back in his chair before speaking, but Mel added one more thing. “Maybe someplace nice where I can dress up again. I don’t get the chance all that often.”
Ray’s smile broadened. “How about dinner, then a club or two. I know you like to dance.”
“Sounds perfect!” Mel replied happily.
“So I was wondering,” Ray said, launching into his newest conversation topic. “You’re a lawyer, so I’m guessing you make a decent amount of money, and I noticed that you drive a nice car – real nice by the way, but the apartment you live in, while it’s nice, doesn’t seem to quite… suit you.” He was hoping he was polite enough by the way he posed the question.
Mel shrugged her shoulders. “I moved there right after college and… I guess I got comfortable. I am working on something right now though where I hope to be buying a new house very soon.” She didn’t add that that something was Sissy!
Ray figured that that explained things fairly well. She just got… lazy about it. She probably didn’t have the “drive” to want all the trappings that came with success. Either that, or she wasn’t all that successful. “So…” he began again, trying to find another topic that dealt with her. “How did you wind up as nursemaid to Sissy?”
Mel almost choked on the word “nursemaid.” Fortunately, she hid it quickly. As far as she could tell, Ray hadn’t heard any of the gossip that Robin was bound to be spreading – yet. And she hoped things would stay that way. “Um… Sissy moved in next door to me.”
“And you somehow discovered that he wanted to be a woman?”
Well, that wasn’t really correct but… She realized she was treading on dangerous territory here. “Um… Something like that.”
“So, how did it happen?”
Big red flags went up in Mel’s mind. “Um… We each got a bit too drunk.”
Something about her answer surprised Ray. “So, you actually went out with him and you both got drunk and he told you he wanted to be a woman?”
“Um… Not exactly. I bought some beer and we had it at my place.”
“So…” Ray continued, just trying to keep the conversation going, “was he dressed as a woman then?”
Mel really wished he’d get away from this line of questions. “No. It just kind of came out while we were blitzed.”
“And you encouraged him in it?” Ray asked incredulously.
Mel really had to get things away from this topic. Ray was asking all the wrong questions. “That wasn’t… quite what happened,” she replied. Then she tried to move things on to something else. “Let’s not talk about Sissy. Let’s talk about you instead. So, do you have something against Derek?” she asked.
Ray was clearly surprised by the question, let alone her changing the subject so abruptly. “No, not really.”
“But you clearly like teasing him.”
Ray smiled. “Who wouldn’t? Sometimes, the guy just asks for it.”
Mel wasn’t all that sure about that. She somehow had the impression that Ray was more like the big rooster in the henhouse, and he didn’t want any competition around. Fortunately, their lunch arrived just then and the conversation went back to their upcoming date tomorrow night. Mel was relieved!

Cindy watched almost angrily as Sissy drove into the parking lot and got out of his car carrying his big pink diaper bag with him. But she dared not make any fuss over the matter since Cassie was standing right next to her, also watching him approach. The reason she was angry, was because Cassie had just told her, in no uncertain terms, that she couldn’t even watch today. And Cassie had made it just as much a point to tell her not to argue about it. So now, she was a bit… miffed at.
Chad got through the gym door and was surprised to see Cassie already up front, waiting for him. But he and the receptionist were staring at him as if waiting for something. With a bit of a sigh, he curtseyed and greeted first Cassie, then he did it again for the receptionist. He was rewarded by seeing the look on the receptionist’s face change to one of delight and he heard her giggle.
“Come on Sissy,” Cassie said as soon as he finished. “Let’s get started.”
Chad couldn’t believe his luck, especially when he realized that the receptionist was staying behind. “She won’t be joining us today?” he asked quietly as they made their way past several women on the treadmills.
“Not today,” Cassie replied.
“Hi Sissy,” one of the women called to him as he walked past. She was very sweaty from her workout. He just waved his arm a bit in reply and kept walking. He really wished they would forget him there, but that was probably asking too much.
“How was your date?” Cassie asked a minute later as he started to get undressed.
“I got through it,” Chad replied.
“But did you have any fun?”
“Well… It was mostly, awkward,” Chad admitted. “Very awkward! But the movie was good!”
“Well, that’s something anyway,” Cassie replied as she started pulling supplies out of his diaper bag. A few minutes later, she peeled back his completely soaked diaper, exposing his chastity clad penis underneath. “So how are things going with your friend Robin today?” Cassie asked as she took a cloth to start wiping him off.
“I don’t know,” Chad replied as he briefly took his bottle out of his mouth. “She won’t speak to me. I don’t think I’ll have to worry about it very long though, because once she tells enough people, I figure I’ll get fired pretty quickly.”
That startled Cassie. “I hope not!” she replied with genuine concern.
“Me too. But I don’t see it not happening.”
“Pray. Maybe a miracle will happen.”
“It will have to be a big one!” Chad replied. He put his bottle back into his mouth and sucked on it worriedly.
Cassie was about to tell him to roll over so she could do his other side, when all of a sudden she saw a ton of pee rushing out of his chastity device. As she quickly grabbed the wet diaper still under him to pull it protectively back in place, she noticed the look on his face – as if he was totally oblivious to what he was doing. Was it possible?
Chad was startled as Cassie suddenly pulled his wet diaper back into place. The action interrupted his moody thoughts enough for him to see the surprised look on her face. He was about to ask what she was so startled about, when he finally realized he was peeing. Embarrassed, he apologized for what had just happened. Geez! He had to get with it and get control of himself again. He had been so worried about Robin and getting fired all morning that he had barely even tried to control himself.
Cassie finally pulled the wet diaper back a bit to check to see if he was done yet. There was still a tiny bit of pee dribbling out of the tip of the plastic device. She watched till it finished. She was just glad that she had noticed what was happening fast enough. Catastrophe averted! She once again wiped off his front side, then slid the now even more soaked diapers out from under him. Seconds later, she slipped fresh dry diapers back in their place. “Okay, roll over,” she finally said.
Chad removed the bottle from his mouth and set it aside as he rolled over, exposing his backside for Cassie to clean – and hopefully play with. The cleaning took only moments, but the luxurious feel of her hands massaging in the baby lotion all over him felt totally exquisite! He closed his eyes as he concentrated on the feel of her hands. His hopeful longings were rewarded when her fingers finally moved closer and closer to his little back hole, and finally into it. What a feeling! He didn’t know why he loved it so much, but he did. It simply felt – great! He enjoyed her finger moving in and out of him for a few moments, then he felt her hands leave him again. A moment later, something much larger and harder was pressed up against him. That made him really happy!
Cassie moved her toy slowly into him, then slowly out again, but it was only moments before he was actively trying to push and pull himself against it. Instead of trying to control it in him, she just held on and let him do all the work – and very soon she had to hold on tighter because he was doing an awful lot of work!
Chad pushed himself back and forth, over and over again against Cassie’s toy. It wasn’t just that it felt good, it was something much more, something… sexual. Maybe it was just that it had been so long now since he had been able to orgasm. Or maybe it was just that he was liking it more and more. He didn’t know and didn’t care. He simply couldn’t get enough of it. And it seemed like his enjoyment from it was more than ever before. But as usual, eventually he realized that all his effort was useless. He wasn’t going to orgasm from it. It was impossible. All he was doing was making himself even more frustrated. That was the big problem with his chastity device, it simply made some things totally hopeless. He slowed down and buried his head in his arms in frustration as he felt Cassie pulling the toy out of him. Hopeless! A moment later, he felt Cassie’s finger invading his backside once again as she pushed the inevitable suppository up inside of him. Hopeless!
Cassie smiled to herself. Once again she had only faked putting the silly little suppository up into him, and once again he obviously didn’t know it. Would he ever find out? She wondered what would happen if he did. Not that it would really matter. Mel would probably go back to making sure he got one every time – and she would probably have it done in such a way that he would know without a doubt that it was there!

The Bet - Chapter 45 (Monday – week 7 Part 2 of 7)

2011-12-06T02:42:00.001-08:00

The Bet
by Karen Singer

Chapter 45 (Monday – week 7 Part 2 of 7)

As Chad pulled into the parking lot, he tried to see if Robin’s car was there yet. He didn’t see it, but that didn’t mean she wasn’t here already. What was he going to say to her? For that matter, what was she going to say to him? The only thing he was certain of was that whatever she said, it wouldn’t exactly be pretty. Bracing himself again, he got out of the car and headed into the building. The few people he saw, didn’t seem to act any different toward him today than usual. He figured that was a good sign. He just knew it wasn’t going to last. Before going into his own cubicle, he checked Robin’s, she wasn’t here yet. It was only a matter of time.

Robin wasn’t in any hurry to get to work today. She didn’t really want to go at all. Things had been so much easier before this weekend – before she knew… the truth. The idiot! She was still angry at him. Complicated? He was damn right it was complicated! She had never really believed it before, no matter how many times he had said it. But now she knew. And now she knew what he was… whatever you could really call it. Idiot? Pervert? Sick? All that, and so much more! She wasn’t looking forward to seeing him. She didn’t want to see him. Because every time she thought about him she got so angry she could spit! The pervert!
Reluctantly, she pulled into one of the parking places, and even more reluctantly she got out of her car and headed toward the building. As she turned down the hall where their cubicles were, her steps faltered for a moment, then they sped up till she was walking much faster. As she passed his cubical, she purposely didn’t even turn her head to look inside. She just kept going, all the way to her own desk.
Chad had been looking at his computer screen when he heard someone pass his cubicle. “Robin?” he called. But he got no answer. Was she here? But nobody else ever came down this way. It had to be her. Getting up from his seat, and knowing it was going to be bad, he went to see her. He cautiously turned the corner into her cubicle, she was just sitting there at her desk with her back to him. “Robin?” he said again.
Robin heard him call her again. The pervert! She turned around quickly in her chair. “Get out of here! Get the hell out of here! I don’t want to talk to you. I don’t even want to see you! Get lost you… you… you jerk!” And just as quickly, she turned her back to him again, hoping that he’d get the point and go away.
Shocked, and even more deeply wounded, Chad turned and sadly made his way back to his desk. It hadn’t gone well. But what did he expect, that she would be laughing and happily accepting of… of… what he was? Did he think that she was going to tell him that everything was wonderful? Get a grip!
He sat down at his desk and stared blankly at his computer screen. Now what should he do? Mel had said she wanted to know every little thing she said to him. He considered calling her, she would probably still be home, or maybe on her way to work. But if he called her, then Robin would hear him talking and would know that he was passing everything on. Instead, he opened up an email and tried to explain exactly what had happened. Telling Mel that Robin was still angry seemed to be an understatement, but he tried his best to stick to the facts.

The first thing Mel did when she got to work was to tell Andrea to watch for Sissy’s calls and to let her know as soon as possible. Then she went in and checked her email. She wasn’t sure if she was surprised or not to see one already from him. Actually, she was kind of glad to see it because he was at least going to be keeping her up to date. She opened the email and read it. And frowned. It wasn’t going well so far. But there wasn’t anything she could do about that. She would just have to wait and see what happened.

All morning long, Chad sat quietly at his desk, worried about what was going to happen. The only good thing that occurred was that Tom Robinson had emailed him a short list of some little things that needed doing. Busy work. Nothing difficult. But it kept his mind occupied for a while. The list of things also meant that Tom hadn’t yet heard about what Robin now knew. Not yet at least. He heard very little over the wall from Robin’s cubicle, except for some faint sounds of her typing on her keyboard once in a while. Was she emailing everyone about what happened instead of phoning them? The more he thought about it, the more likely it seemed.

It was mid-morning when Mel finished with a client and Andrea told her she had a phone call while she was busy. But the call wasn’t from Chad, it was from Ray instead. Mel couldn’t believe it, she had totally forgotten about Ray. She had been too preoccupied worrying about Sissy instead. But now that she had been reminded, she happily sat down at her desk and dialed his number. “Hi Ray. It’s Mel.”
“Mel… How are you today?”
She wasn’t about to tell him that just thinking about him was making her horny again. “Don’t ask!” she said instead. “Lots of worries today.”
“Can I take your mind off of them with some lunch?”
“Lunch?” She really had a nice dinner somewhere in mind instead. Besides, she usually met with Gloria. “Uh… Sure, why not?” Gloria would just have to go on her own.
“Excellent! Because otherwise I might have had to hold all these pictures I have from last night ransom till you agreed to go out with me.”
“The pictures! I can’t wait to see them! And… to be honest, I was really thinking of something a bit more… interesting than just having lunch with you. I mean, just you and I, without anyone else.”
Ray couldn’t believe it! What a woman! “Well, besides lunch today, how about we go out somewhere tomorrow night?”
That surprised Mel. “Tomorrow?”
“Yeah. I’m kind of busy tonight.”
Mel had no doubt about that and briefly wondered who he was going out with. It also took some of the interest out of it for her. But… “Yeah, tomorrow night is good for me too.”
“Wonderful!” Ray exclaimed. “We can talk about it over lunch today. Now, where do you want me to send these pictures?”
It wasn’t till Mel had hung up the phone again and was spending a moment picturing herself out with Ray tomorrow night – and then forced herself to get back to thinking about Sissy’s problem, that another problem hit her. Sissy! What was she going to do with him tomorrow night? She couldn’t just leave him alone. She didn’t dare! He spent way too much time every day at work holding back and regaining his control. A single evening of it too would be disastrous. What was she going to do with him?

Gloria was between clients when she happened to check her email. She noticed one from Mel, which was strange because Mel usually phoned. She opened the email without hesitation though… and stared in shock at the picture on her screen. It was obviously Sissy – dressed very nicely from what she could see. But he was in the arms of another man and they appeared to be kissing passionately! Just below the picture were two simple words: “Call me!”
Never taking her eyes off of the picture, she picked up her phone and dialed Mel’s number. “Mel?”
Mel giggled at hearing Gloria’s voice. “Do you like it?”
“It’s really… something!”
Mel giggled again. “You should see some of the other pictures too.”
“You have more?”
“A bunch!”
“It looks like you had some fun last night for sure!”
“More than you’ll ever know!”
Finally, Gloria smiled. “Well, I can’t wait to hear about it. Lunch today?”
“Uh… That’s one of the things I wanted to talk about,” Mel replied. “I can’t today. I’ve kind of got a date.”
“A date? With which guy? The one you were dating last night or the one that Sissy was with – that you said you liked better?”
“My date. Ray.”
“I thought you said he was scum?”
“Well… He is, but… Well… Damn, he had me so hot last night!”
“So you finally got laid again! Good for you!”
“No. No… we didn’t… It’s just that…”
“Wait a minute, you didn’t get into bed with him but things got… hot?”
“For me anyway.”
“From that picture you sent me, it looks like Sissy wasn’t doing too bad either.”
Mel giggled again. “Trust me, neither of them really liked it.”
“You could have fooled me!”
“So anyway, I just wanted to let you know that I can’t meet with you for lunch today. It’ll have to wait till tomorrow.”
“Whatever. Just go have a good time!”
“Thanks, Gloria. It’s a shame though, because I really need to talk to you.”
“About what? It sounds like everything is going great.”
“Well, not everything. I kind of made a big mistake with Sissy this weekend and I don’t know how to fix it.”
Gloria sighed. Sissy again! “I’m afraid that other than lunch, I’m kind of booked up all day today.”
“Yeah, me too. And my schedule looks to stay that way for the next few weeks. We’ll just have to put it off till tomorrow. Okay?”
“Whatever. Sounds fine with me. Oh, and Mel…”
“Yeah?”
“I’m glad you’re having some fun!”

Chad was working, but his body was on pins and needles. He kept waiting for the expected phone call to come from his boss, Tom Robinson, telling him that he was fired and to clear his things out. He was so worried about it, that he barely gave any effort into trying to hold back when he had to pee. It was just a bit too much to think about. Too much to worry about when the executioner’s ax was hanging right over his head. He knew his diapers were soaked, but he wasn’t about to worry more than normal about them. Wetting and leaking were totally secondary to everything else.
He heard Robin moving in her cubicle over the wall. He glanced at the clock – break time!
It wasn’t that Robin really wanted to go to break, it was more like she really needed something more to distract her – and her anger. She got up from her seat and walked out. She stopped at the entrance to Chad’s cubicle and looked in. There he was – the sick pervert! He was just turning around in his chair like he expected her to talk to him. Well… “I’m going to break,” she said. “Don’t come!” With that, she turned away from him and walked off. For some reason, she felt a bit better about things.
Chad stared open-mouthed at the empty entrance to his cubicle. “Don’t come?” Those two words seemed to speak volumes. Feeling worse than ever, he turned around and stared at his computer screen again. But work was out of the question. At least not for a while. Instead, he opened up another email and sent a short note to Mel about what had just happened. He hadn’t heard back from Mel yet today, but why should he? There was nothing she could do to help.

Robin grabbed a coffee and headed for the women’s table. The minute she sat down, her friends were asking about where Sissy was and how his date went last night. The truth was, she had totally forgotten he was supposed to go out with Derek last night. She hadn’t even given it the slightest thought. And to really tell the truth, she didn’t care in the least. “Oh, he’s working,” she replied to everyone. “I don’t think he’s going to be able to make it today.”
“So how about his date,” someone asked again. “What did he say?”
All Robin could do was to shrug her shoulders. “We haven’t had a chance to talk yet. Like I said, he’s been working pretty hard today.”
“Awfully convenient, if you ask me,” one of the women replied. “I’ll be he just doesn’t want to share all the ‘intimate’ details!” There were a few chuckles from around the table, but not from Robin.
“I’m surprised at you girl!” another woman said to Robin. “That’s not like you. Usually you get in there and dig, no matter how busy they are!”
Robin blushed, “Well, I’ve been a bit too busy today too.”
“Sounds strange to me,” someone else replied.
“You make sure he’s here later,” another woman told Robin. “We can’t have him not filling us in with all the details after his first date like that!”
Robin still wasn’t ready to have Sissy anywhere near her, but she realized that the other women weren’t going to let up till they got what they wanted. She on the other hand, had already had her fill of him!

Mel read Chad’s latest email with interest – and worry. Obviously Robin wasn’t coming around yet. But at the same time, Chad still hadn’t mentioned anything about being fired – yet. That was good news – she guessed. Of course, if he did get fired, then maybe he would be more interested in losing their bet – just so she would take care of him. It was a nice thought, but she knew it wouldn’t happen.
One thing she realized that she hadn’t realized before, was that in telling Robin about Chad and their bet, she had not only hurt Chad, but she had also hurt Robin too. Robin hadn’t been ready to accept any of the “kinkier” aspects of Chad’s life and in learning about it like she did, Mel had pretty much destroyed the friendship between the two of them.
But somehow, she just didn’t see Robin as the type to ignore Chad completely – and permanently. And since Chad hadn’t yet mentioned anyone else giving him any trouble, then she was also beginning to wonder if Robin would actually tell anyone else. Of course, it was still early yet, and from everything that Chad had told her about Robin, she was guessing that Robin would have to tell someone. And even so, she was also guessing that eventually, Robin would probably have it out with Chad. The more she thought about that, the more she had no doubt at all that it would happen – and, she was betting that it wasn’t going to be pretty either.
She decided that maybe she should warn him to prepare him for what she was guessing was coming. She started typing a return email to him about her thoughts on what was most likely to happen as far as Robin went, but halfway through, she stopped. An odd thought struck her. One that needed more time to examine. She closed the email without replying as her mind pondered the idea. It was crazy!
She grabbed a folder off of her desk and got up to meet with her next client. But her mind wasn’t on work, it was on Chad and Robin. What a dumb idea! It was stupid! But it was now stuck in her mind.

The Bet - Chapter 45 (Monday – week 7 Part 1 of 7)

2011-12-02T02:51:00.000-08:00

The Bet
by Karen Singer

Chapter 45 (Monday – week 7 Part 1 of 7)

He wore the same blue dress, the same shoes, the same everything. But in his dream, he was alone with Derek. The two of them were simply walking side by side together, and he felt totally comfortable, totally secure with him. They didn’t hold hands. Instead, Derek’s arm was across his shoulders, holding him close to his side as they walked.
For some reason, they stopped and Derek turned toward him. Derek cupped his face in his hands and ever so slowly brought his own face down to meet his lips. Soft lips… sensual lips…met his. The kiss lingered and his body enjoyed it. But even as he enjoyed the kiss, the wrongness of what they were doing rose up from the pit of his stomach. This was so wrong! So wrong! He screamed in his dream… and his body jolted completely out of sleep. Images of what he had just been dreaming about still lingered in front of his eyes. Ugh! What a dream! Why would he even dream such a thing?
It was a moment before he realized that the light in his room was still muted. But then it was usually that way when he woke up. But his alarm hadn’t gone off yet. He wondered what time it was.
Before he could move his body to check his clock, his body first registered other things. He was aware that his legs were splayed wide apart. They were being forced that way by the super thickness of his diapers. She had loaded a lot of the thick cloth diapers on him last night and he could feel how wet they were inside of the plastic panties that covered them. He had no doubt that he had wet an awful lot last night. Mel had made sure that he had consumed way too much to drink – again. He could feel the slimy mess in the back of them too from where the stupid suppository she had stuck up inside of him had done its work. Ugh! He could also feel the weight of the breast forms glued to his chest and the bra he was wearing to help hold them there. And finally, as his body started to tense up enough to roll over on his blow-up mattress, he realized that his pacifier was still in his mouth – where it usually was every morning now.
He rolled off of his mattress, and was immediately aware of how extra heavy his diapers were this morning – if it was morning. As he hit the floor, he knocked down several empty baby bottles, but he ignored them as his brain was still registering the weight and bulk of his diapers as his eyes sought the display on his pink alarm clock. He got to his knees and stared at the clock. Before he could fully register the time, one of the numbers changed and he was immediately assaulted by loud rock music that blared from the radio. Loud enough to startle him badly. Loud enough to fully bring him to his senses. Loud enough to make him reach out as fast as he could to turn the horrid noise off!
It took a moment for the shock of the noise to abate from his mind. It was morning again. Time to get up. Time to… Ugh! It was Monday! He had to go to work! But… But Robin! Robin now knew everything! Robin would spread the word to everyone! Everyone would know! Everyone would laugh! Everyone would berate him for what he was. And he had no doubt that before the day was out, he would be fired from his job.
What was he going to do?
He climbed awkwardly to his feet, more aware than ever of the weight of his diapers this morning. Wow, he must have peed a lot last night! He was amazed that he hadn’t leaked all over everything. But then, Mel had piled on the diapers like never before. He pulled his pacifier out of his mouth and set it down on his cardboard dresser where he could easily find it easily when he went to bed. Then, wide-leggedly, he half stumbled out toward the kitchen to look for the note she usually left him.
It was there, but it might have been the same note she had left him most days. Nothing new at all – fortunately. He was actually comforted by that little thought. Each day since this bet had started had turned out to be worse… and more humiliating than the day before.
He pulled three more baby bottles out of his refrigerator and carried them back toward the only piece of real furniture in his apartment – if you could call it furniture. It was only one single chair that he had pulled out of storage after he had split from his wife – make that ex-wife. The one piece of furniture she didn’t want. He sat in the chair and put the first bottle to his mouth. For once, he didn’t really see the childishly colored pictures taped to the wall in front of him. They were there, but they didn’t matter. His brain was too focused on worrying about Robin… and his job. What was going to happen today? No matter what, it wasn’t going to be good.

Mel pulled her robe tighter around her as she headed out of her bedroom toward her kitchen. Coffee! She needed coffee! As if it would help. She knew without a doubt that it wouldn’t. Nothing could help her problem… well, one thing certainly would. But the problem was that right now, the only “other” coherent thought on her brain was getting some coffee.
She opened the cabinet and found the can of coffee. The cabinet seemed fuller than usual. She measured out the grounds and added them to her coffee maker. She filled the carafe with water from her sink and poured it in. She turned on the coffee maker – and just stood there staring at it. Why did it always take so long to make? Soon! Very soon! Sissy would be there every morning to make it for her. Freshly made every morning and delivered to her bed. Soon! Very soon! She hoped!
As the coffee slowly brewed, her thoughts automatically returned to where they had been before… where they had been – in her dreams. Loving arms surrounding her. Loving kisses so sensual they made her squirm with sexual anticipation just thinking about them. And little caresses so intimate that she never wanted them to stop. Why hadn’t she let Ray stay last night? Why? She had been so horny all last night she could barely stand it. And this morning? This morning she was still thinking about him… well, she was thinking about having sex with him… along with his crazy fingers during the movie last night. It had been a good movie too… or was it just Ray that had made it seem that way. But last night she had told herself that she wouldn’t sleep with him… last night anyway. And besides, she had other considerations last night. Sissy for one… Oh yeah, Derek had been there too. And Ray had to take Derek home. Derek… another super hunk!
The coffee finished brewing – finally! She opened the cabinet to pull out a cup, and stared in surprise. She glanced around at where she was. No it was the same cabinet she always pulled her cups out of…. but they weren’t there! She was staring at food supplies instead! Then she finally remembered. Sissy! Sissy had rearranged all her cabinets yesterday. But… but where had he put the cups? She stared opening cabinet after cabinet to see what was in them. One large double cabinet held only baby food. She smiled at seeing it. He would be eating a lot more of it from now on. She finally found her cups… surprisingly, right near her coffee pot. They were just all moved to the other side.
She pulled a cup out and filled it. She took a sip. The hot liquid seemed to burn all the way down to her stomach. So good! She took a deep breath to help wake herself up before taking another sip. No, she didn’t want to sleep with Ray last night. But she was absolutely determined to call him at her first opportunity this morning!

Chad stared at the clothes in his closet. Only women’s clothes. Not one shred of male attire in his entire apartment. Mel had moved them… taken them all away to… somewhere. He had no clue what she had done with all his male things. So now he was forced to wear nothing but women’s clothes everywhere. And, the way things had worked out, pants – even women’s pant’s – didn’t work for him very well either. So that left him with only dresses and skirts to wear. It was a good thing he loved wearing them.
He stood staring at his closet for the longest time. He was already wearing two disposable diapers, plastic panties, a waist cincher, an all-in-one girdle instead of a bra to hold up his glued-on breast forms, and pantyhose on top of that. He had already fixed his hair and done his makeup. So now, all that remained, was to get dressed. But what should he wear? Actually, the more correct question was – what would be the best thing to wear to get fired in?
He thought about his colorful patterned dress, but somehow that seemed too… bright and colorful for getting fired. Too happy a dress? He thought the same about his zebra print dress too. It was too bold for the occasion. So that left him with skirts. He finally chose the dullest skirt and top combination he could put together. And instead of high heels, he chose the shoes he wore with his maid’s uniform – the lowest heels he had. As he slipped them on, he remembered the heels he had worn last night for his date with Derek. These shoes were so much more comfortable! Maybe not as much fun, but certainly much more comfortable.
Finally ready, he grabbed the plastic bag filled with all his empty bottles from last night and this morning. He grabbed his purse and his diaper bag. He took one more deep breath to brace himself for the day ahead. A day that he knew would be… awful! And he opened his door to head for Mel’s apartment. He was on his way toward – who knew what… again.

Mel opened the door to his knock and smiled at his curtsey and good morning greeting. “Good morning, Sissy,” she replied as she stood back out of the way so he could enter. She waited while he dropped his diaper bag and purse in their usual place under the table by the door and then she took the plastic bag full of empty bottles from him. As he stood there, she looked him over carefully. He looked… fine. But… but there was just something different today. Something a bit… duller. She couldn’t quite put her finger on it. Maybe it was just that he was worried about his job today. Well, that would just have to sort itself out later. “Okay Sissy, up in your highchair.”
A few minutes later, Chad was “locked” into his highchair, a bib was tied around his neck, and he was eating tasteless baby cereal with a baby spoon held in his left fist. Business as usual, except that, so far, he hadn’t dropped any of the cereal off of his spoon.
Mel leaned back against the kitchen counter with a fresh cup of coffee as she watched him eating. She realized quickly that he wasn’t being as messy anymore as he used to be. Well, that had both its good and bad points. Good because it was less mess, bad because, well, it was fun to see him make such a fool of himself.
But as he ate, she noticed that there was still something different about him today. Despite how hard he seemed to be concentrating on eating, there was still something else. “Are you worried about work?” she finally asked.
Chad looked up from his breakfast. His left fist, still holding the tiny spoon, slowly sank down to the tray. “Yeah,” he said simply. “I liked this job.”
“You haven’t been fired yet.”
“It’s only a matter of time. It has been since our bet started. I’m afraid that time will be running out today.”
“You don’t know that.”
He shook his head. “Once Robin starts talking – if she hasn’t already – I can’t see how anyone will want me around.”
“I don’t think you give yourself enough credit. And people may surprise you, even your friends at work.”
Chad shook his head again as he picked up his spoon and almost mournfully dipped it into the baby cereal again. “Somehow, I doubt it.”
“Tell you what, you keep an open mind. And remember, I promised to help you.”
“I don’t know what you can do.”
Mel stared at him for a moment. “I don’t know either. But we won’t know till something happens – if anything happens.”
“And it will!”
She had to admit, it was the more likely possibility. “Listen,” she said. “I want you to tell me everything that happens today. I especially need to know every conversation – even the minor inconsequential ones. And especially everything that Robin says and does. Also let me know about every little funny look that people give you. I can’t help you if I don’t know what’s going on. Keep me abreast of things constantly. You can phone me or email me, I don’t care. I’ll tell Andrea to keep a special watch for your number and let me know as soon as I’m available. Can you do that?”
Chad shrugged. “Sure, I guess.”
“Good, like I said, I can’t help you if I don’t know what’s going on.

A Different Kind of Comment

2011-11-30T05:24:00.001-08:00

Hi All,

I really just wanted to say thank you again to everyone who is reading this story. And I’d like to say a special thanks to the couple of people who have emailed me recently or left a comment in this blog – you know who you are! You don’t know how much I appreciate your response.

On the one hand, the comments let me know that someone out there is reading this and appreciates it, but on the other hand, what kind of comment can you really write? Mostly, I think everyone is enjoying the story so no comments are necessary and to tell the truth, I don’t expect any.

I’ve found a different way to gauge whether people are enjoying this story or not – the followers list at the side of the page. Over time, I’ve been steadily watching the number of followers going up and up. I can’t believe how many I have now! Thank you – all of you!

There is one more way that I’ve found to gauge this story. Blogspot has a stats page where I can go to look at how many hits this blog has had over varying periods of time. On a daily basis, I get between 200 and 600 hits. On a monthly basis the hits range from about 10,500 to 16,000. It actually fluctuates back and forth quite a bit. But overall, those numbers seem to be rising too.

So I am currently basking in the knowledge that there are a lot of people out there who are reading this story and enjoying it! That’s what it’s all about for me! Thanks to every one of you! Those numbers keep me going!

I guess while I’m here I should mention that I keep a text file of the completed posted chapters so far. You can email me at siskarensinger at yahoo dot you-know-where if you want a copy so you can catch up on anything you’ve missed without searching back through the entire blog.

I guess I should also mention again that the Baby Bobby story I wrote some time ago is still available too if you want it. Just email me and tell me what you want.

Oh yeah! I recently sent out a copy of my very old What’ll I Wear program to someone and he said he actually got it to work with no problem! If you’re interested, I guess I can send that too. I make no guarantees about it though.

So have a happy holiday season everyone. Please enjoy it to its fullest! And please stay safe !

Karen

The Bet - Chapter 44 (Sunday – week 7 Part 9 of 9)

2011-11-29T02:45:00.000-08:00

The Bet
by Karen Singer

Chapter 44 (Sunday – week 7 Part 9 of 9)

As they all stood up to exit the theatre, Mel “offered” to hold Sissy’s cup for him while he grabbed his purse and got to his feet. She noticed that the cup was now totally empty. Not even the ice remained! How perfect was that?
As Chad got to his feet, he immediately realized what he hadn’t realized before. His diapers were huge! Girdle or no girdle, he had peed so much during the movie that they were now super bloated. But were they leaking? He hoped not. As he struggled in his super high heels, with his legs now spread wider than before to get out of the aisle, he stumbled a bit and felt Derek’s strong hand grab his arm to help steady him. “Thanks,” he said as he turned back briefly. He was surprised that Derek continued to hold his arm to help steady him till he reached the end of the aisle. He expected Mel to give him back his empty cup so he could throw it away, but instead she just reached down and set it on the floor out of the way. The cleaning staff would have to deal with it later.
The trip down the steps was interesting for him. Between the super high heels and his super bloated diaper, negotiating the easy steps was more of a challenge than he thought it would be. But he made it. He only hoped that Derek – and everybody else, wouldn’t notice how oddly he was walking now. And… damn! Was that a bit of wetness he was feeling between his legs? Damn! He was leaking! And there was nothing he could do about it. Well, hopefully the girdle would keep that from showing too. He hoped.
Mel and Ray reached the bottom of the steps and “waited” for Sissy and Derek to catch up. Ray was going to lead the way out, but Mel held him back for a moment till Sissy and Derek could get in front of them. She wasn’t sure if she should be surprised or not at the tear tracks that were all too obvious on Sissy’s face he went past her. She quickly reached out and whispered into Sissy’s ear before he got past her, “Grab his hand!”
The command to grab Derek’s hand, on top of all the other things he was feeling just then was almost more than Chad could take, and he let out a bit of a cry at hearing it.
Derek stopped for a moment as he heard something from Sissy. “Damn! Are you still crying over that thing?” He looked back at Mel and noticed that her eyes were still a bit damp too. He shook his head. “Women!” He started walking again with Sissy by his side. “It’s just a silly movie,” he said, trying to get Sissy to stop crying.
“Yeah, I know!” Sissy replied with more emotion than he wanted. Actually, the emotion was mostly coming now from Mel’s order to grab Derek’s hand and hold it than from the movie. But having said that, he reached out his hand and grabbed Derek’s.
Oh brother! Derek couldn’t believe it. Sissy was actually needing some kind of comfort and hand holding? After just a silly movie? And he claimed he wasn’t on hormones… or whatever it was that Sissy’s kind took. But feeling like more of a sap than ever, he “allowed” Sissy to hold his hand to comfort him as they headed down the long hallway toward the lobby again. And over and over again, Ray’s little cell phone camera was snapping picture after picture behind them.
Sissy couldn’t believe it! Derek was actually holding hands with him. It was as if he was a real woman that Derek was out with. He couldn’t believe how strange he felt about that. He couldn’t even begin to explain it. One thing he could explain though was how much wetter and wetter he seemed to feel as they kept walking. His diapers had to be so soaked! But now he was worried about it showing up on the back of his skirt. Would anybody notice? He sure hoped not!
“Is it my imagination, or is Sissy walking funny?” Ray pointed out to Mel as they followed them.
Mel almost laughed. She had also noticed Sissy’s odd walk, and it had nothing to do with his high heels. But she couldn’t tell Ray that at all. “Those heels are probably killing him,” she explained.
“I’m not the least bit surprised,” Ray replied.
Once they reached the lobby, Derek was intent on heading straight for the car, but Mel stopped everyone. “I’m afraid I need to fix my face in the ladies room before we go home again. Coming Sissy?”
Chad gratefully dropped Derek’s hand and followed her into the ladies room – again. Wow, he hadn’t been in a bathroom so much in a very long time. And a bathroom was probably the right place to be going since his diapers were so wet. Unfortunately, he didn’t have his diaper bag and he knew without a doubt that there was going to be no “fixing” them till he got home.
Again, the room was fairly busy, but not as busy as before the show. While Mel went into one of the stalls again, Chad found the mirror closest to the corner and out of the way. Ugh! His face was a mess from the crying he had done. But was it worth trying to fix it all now? Well, there was probably no hope for it. Mel had said she was coming in to fix her face too. He carefully wiped his face, trying to preserve as much of Sandy’s makeup job as possible. Then he started in on fixing things as best as he could. Two minutes later, Mel was beside him doing the same thing. “Is this good enough?” Sissy finally asked.
Mel looked at him. He had done a fairly good job and quickly. At least he didn’t look a horror anymore. She smiled. “Good enough… except… I want you to add another really thick coating of lipstick.”
“More? But I just did that!”
Mel shook her head. “Make that two more coats! Heavy ones!”
Chad wanted to scream. But he went back to the mirror and added another “thick” coating of lipstick to his lips. Then he glanced up at Mel. “One more to go,” Mel said. Once again, he ran the lipstick “thickly” over his lips. They now felt so overly bloated with lipstick that he almost couldn’t stand it. He was starting to get tired of the “taste” too. It was simply too much.
Mel smiled. “Now we can go home.”
“Mistress…” Sissy quickly stopped her. Very quietly he said, “I’m leaking! Badly!”
Mel didn’t know whether to cheer or be worried about it. “Well, there’s nothing we can do about that here. We’ll just have to take care of it when we get home.” She paused for a second. “Wait a minute! Spray yourself with a bit more perfume. That will disguise any smell, just in case there is any.”
Chad wasn’t all that fond of the idea, but it did have some merit. Not that he wasn’t going to do as Mel told him anyway. He dug the perfume out of his purse and “carefully” sprayed his wrists again.
“Here, give me that,” Mel said as she took the perfume from him. She sprayed his neck with it too and also went behind him and sprayed a bit on the back of his skirt. “There, that should do it!”
“Is my skirt wet back there?” Chad asked.
“No. Not yet anyway.”
Chad was very relieved. For now.

Ray didn’t exactly take his time driving back to Mel’s apartment, something Derek was glad about. Sissy didn’t really mind it either. But Mel’s thoughts lingered mostly on Ray and the fact that she was determined that she wasn’t going to sleep with him – tonight – despite how she had felt in the theatre. Another day, well, that was a different matter. But she also knew that Ray was going to “push” the issue when they got home. Well, she would just have to refuse him. Tough if he didn’t like it! Her main concern tonight had to be Sissy! Winning this bet meant a lot more to her than a simple tumble in the sheets… well, even if it wasn’t just a simple little tumble.
Ray pulled into the same parking place he had used earlier and everyone got out of the car. Chad held back a bit and tried to grab his skirt in such a way the no one would realize what he was really doing. He pulled on it a bit and used his hands as if straightening the back of it, but what he was really doing was trying to feel if there were any wet spots. And… unfortunately… he was able to feel damp fabric fairly quickly. He hoped it hadn’t spread too much or was too noticeable.
Mel led the way up the stairs and Chad brought up the rear – walking a bit wide-legged and awkwardly in his heels. Mel reached her door and unlocked it, and pushed it open – slightly. Then she stopped and turned to Ray. “Thank you for such a great evening,” she said. “You have no idea how much I enjoyed it.”
Ray was surprised. “But… you’re not going to invite me in?”
Mel shook her head. “Not tonight. I have other things I have to do tonight, and you’ve still got to get Derek home again.”
“Yeah!” Derek chimed in.
“But…” Ray started to argue.
Mel just put her hand on his chest to stop him. “Not tonight!” Then she added a bit softer. “Call me tomorrow. Please!”
Ray, realizing he had just lost out, was very disappointed, not to mention a bit angry, but he held his anger back. “I had just hoped…”
“Not tonight,” Mel repeated. “But there’s still one more thing we have to do before you can go. Kiss me… please!”
“Damn!” Derek muttered in the background. He turned toward Sissy. “I was really hoping we could forget about this part.”
“Me too,” Chad agreed.”
Since Derek was going to have to kiss Sissy and he was going to get a goodnight kiss from Mel, Ray was at least feeling somewhat better about things. With a smile on his face, he looked down into Mel’s upturned face. He grabbed her face with both hands and lightly planted a kiss on her lips. Then, not really separating, he wrapped his arms around her and pulled her into him firmly, and kissed her so much more firmly – yet tenderly.
Mel was tempted to drag Ray inside with her during that kiss, but she held out and just enjoyed it. It had been a long time since anyone had ever kissed her like that. In fact, she couldn’t remember anyone ever kissing her so well. The kiss finally broke and before he could let her go she said, “Yeah, please call me tomorrow – for sure!”
Ray was a bit more pleased. “Don’t worry, I will,” he replied.
He let Mel go and turned toward Derek and Sissy. “Your turn,” he said tauntingly.
“Damn!” Derek said with a shake of his head. “I’m not doing this!”
Chad was actually relieved. “Good,” he added quietly.
“Sorry pal,” Ray said. “You’ve got to.”
“No I don’t! I think I’ve been a good enough sport tonight already. I went to dinner, I went to the movie. Heck, I even danced with him. But that’s as far as I go!”
Mel stepped forward, “Please,” she said. “You’ve got to.” Then she thought of another idea. “Pretend you’re kissing me,” she suggested. “In fact, think of it as an audition. Let me see how you would do it and then I’ll decide if I want you to call me or not.”
Derek just stared at her. Ray and been practically rubbing into his face the fact that he was dating Mel instead of him all night long. “Damn!” he exclaimed again.
Before Chad could react, Derek turned and grabbed him and pulled him into him. He wrapped his arms around him and held him tightly, lowering his head slowly toward Chad’s face. Chad barely had time to register that the kiss was coming before their lips met – softly. Ever so softly. As Derek’s arms closed tighter around him, the pressure increased on his lips till they were kissing firmly. As horrible as it was, Chad felt the breath go out of him from the passion of the kiss. Then he felt himself being grabbed tighter, and tighter, and… and Derek actually picked him up off of his feet and held him there while still kissing. Chad was feeling so many confusing emotions running all through him, including his body peeing into his leaking diapers again.
Derek lowered him back down and Chad quickly found his balance in the heels he was wearing so he could support his own weight. And just as softly as the kiss had started, Derek began to withdraw – slowly. Their lips parted, and Derek was still looking at him as he slowly drew his head away. Chad barely registered the fact that Derek’s mouth was covered in red lipstick – a lot of it. He felt dizzy for a moment. He had simply never expected anything like that. As if dazed, he just continued to stare back at Derek’s face.
“There! Now let’s get out of here,” Derek said as he turned and strode off toward the stairs.
Mel’s legs actually felt weak from watching the kiss. Wow! First the kiss she had gotten from Ray, and now that she had seen what Derek could do too… Where had these guys been all her life?
“I guess…” Ray started to say as he put his cell phone back into his pocket again.
“Go!” Mel said, interrupting him and giving him a little push. “Just don’t forget to call me tomorrow.”
With a nod and a smile, Ray turned and left too. Mel stared after both of them till Ray’s car drove out of sight. Only then did she turn back toward Sissy. His mouth had lipstick smeared all over the place. She had wanted it thick to make sure that Derek would wind up with a lot on him, and it looked like she certainly got her wish. She and Sissy just stared at each other for a moment. “Wow,” she finally said. “Both of them can really kiss!”
Chad still couldn’t speak. All he did was to nod.
Mel almost laughed. “Curtsey for me Sissy.”
Chad actually smiled as he curtseyed. “Yes, Mistress,” he said in his sissy voice. Only then did he take the time to realize, he had gotten through it. He had gotten through the whole date – kiss and all. And it hadn’t really hurt a bit – other than his aching feet. Whew!
Mel knew she could have stayed with Ray tonight, she knew she could have done it easily. The only real sticking point would have been getting Derek back home. But something could have been worked out for that. It was almost a matter of principal though, she and Sissy hadn’t been separated in the evening since this bet had started. And… she just wasn’t ready for it yet. Tending to Sissy had to be her first concern – a concern above all others. It was almost like… like having a baby. She almost chuckled at the thought. “Come on, Sissy, let’s get you changed for the night.”
A little while later, Chad was clad in four extra large cloth diapers. His plastic panties were stretched tightly over them. But Mel figured that he was probably going to need all that protection tonight – given the amount that he appeared to be still peeing. Mel had made sure to stuff another suppository up inside of him in the process. The one this afternoon had been faked, there was no way she was going to forget this one. Going without one twice in a row was coming up all too soon – tomorrow in fact. And Mel was actually worried about what might happen.
Wearing only the huge diapers, plastic panties, and a bra to hold up his glued-on breasts, Chad headed awkwardly for the door. He could hardly walk his diapers were so huge – and he had only wet them two or three times since Mel had started diapering him. It was going to be a long night. And tomorrow… tomorrow he would have to face Robin… and would probably get fired! He turned back toward Mel, and curtseyed. “Mistress, I’m worried about tomorrow.”
Mel shook her head. “We’ll worry about tomorrow – tomorrow.” She smiled then. “Did you have fun tonight?”
Chad thought about it. He almost spoke without curtseying again, but he remembered just in time. “Yes, Mistress. I actually did. And the movie was great!”
“Yeah, it was good, wasn’t it? Go home and dream about your date tonight Sissy. Dream about dancing with Derek… and kissing him. Just don’t forget to drink three more bottles before you go to sleep.”
Dream about Derek? And kissing him? Chad inwardly shuddered. Yet… it had been a more interesting experience than he thought it would be. And talk about intense! With a nod, he curtseyed one more time. “Goodnight, Mistress.” He grabbed both his old purse and his new clutch purse. He pulled his door key out and got it ready. He grabbed his high heeled shoes in his other hand. Everything else could stay. Everything else had to go into the wash – soon! And then he was out the door and heading home. Dream about Derek? She had to be kidding! Derek was one thing, but Robin and getting fired were another!
Mel stared at the door long after Sissy had closed it behind him. He was right to worry about tomorrow. He was right to be worried because of what she had done… a mistake she had made. And she had no idea how she could possibly fix it. “Good night Sissy,” she said softly into the empty room. “Good night… and good luck tomorrow.”

The Bet - Chapter 44 (Sunday – week 7 Part 8 of 9)

2011-11-25T02:43:00.000-08:00

The Bet
by Karen Singer

Chapter 44 (Sunday – week 7 Part 8 of 9)

The movie theatre was a large complex with lots of movies playing. Sissy felt like he stood out way too much since he and Mel were so obviously overdressed. But like everything else, there was nothing he could do about that.
Ray asked Mel if there were any movies that she was interested in seeing. But Mel had been so busy with other things in her life that she didn’t even know what most of the movies were about. Knowing that women preferred the romantic ones, Ray suggested several that he already knew were good. The fact that he had already seen them didn’t go unnoticed by Mel. She finally decided on a romantic comedy that she figured would be enjoyed by everyone – and that would be starting fairly soon. While Ray and Derek were buying the tickets, she dragged Sissy once again into the ladies room.
While Mel went into the stall again, Sissy had to add yet another layer of lipstick on top of his already overly coated lips. There were a lot more women in this restroom than Sissy ever had to deal with before, but he went to as far a corner as he could to work in front of one of the mirrors there. And as far as he knew, none of the other women in there noticed him… much. At least nobody said anything to him – fortunately.
Before they left the ladies room, Mel had a little more “advice” for Sissy. “Before we go into the movie, get yourself the largest drink you can. And I better see it finished before the movie ends!”
Sissy wanted to scream. More liquids! “Yes, Mistress,” he said softly.
Mel smiled at hearing him refer to her as Mistress, but she wasn’t quite done with him yet. “There’s just one other thing,” she said with a gleam in her eye. “From now on, whenever you and Derek are walking anywhere, I want to see you try to hold his hand!”
Sissy was shocked! As the realization of what she was saying sunk in, he thought his knees were going to buckle. Fortunately, he stayed upright. And then Mel turned around and headed for the door… and he had to follow.
Out in the lobby, Ray and Derek were just returning with the tickets. Mel glanced at Sissy as they all met up again. “Um… If you don’t mind,” Sissy said, “I’m going to get myself a drink before we go in.”
“You’re kidding!” Derek said. “You had enough iced-tea to drown a horse in the restaurant!”
Sissy just shrugged.
“Nerves!” Mel stated for him. And that seemed to explain it sufficiently to everyone.
Sissy was about to excuse himself to get the drink, when Derek rolled his eyes and asked. “What do you want? I’ll get it for you.”
Sissy couldn’t believe it! Derek was going to buy him his drink too? “Uh… Just a coke please… The largest one you can get!” he added quickly.
Derek looked at him like he was crazy – once again! “You’re not kidding?”
Sissy embarrassedly shook his head. “Please?” he said shyly.
Derek turned away and walked off toward the concession stand.
Not to be outdone, Ray quickly asked Mel if she would like anything, but Mel refused stating that she had already had more than enough.
When Derek came back with the drink, Sissy thanked him and took a quick sip, as if to show that he really wanted it. Then they started heading toward the theatre where their movie was supposed to be playing. For some unknown reason, this time, Derek and Sissy seemed to be in front, leading the way, while Ray and Mel followed. As he walked next to Derek, Sissy suddenly heard Mel loudly clearing her throat behind him. He doubted anyone else took much notice of it, but he did. He moved his drink to the other hand and ‘cautiously’ reached out his hand to touch Derek’s.
Derek was startled by Sissy’s hand touching his – as if he was trying to hold his hand! Startled, he quickly pulled his own hand away and looked over angrily at him. What the heck did he think he was doing?
Since Derek obviously wasn’t going to hold his hand, Sissy relaxed and just followed him into the theatre.
Once inside, Ray suggested moving toward the back – where it would be easier for him to see the whole screen. He got a dirty look from Derek for that suggestion, but they climbed up to the back of the theatre and all entered one of the rows together. Derek went in first, followed by Sissy, followed by Mel, and finally Ray. TV commercials were playing on the screen and Chad lamented the fact that even at the movies they could no longer get away from them.
Having no better place to put his purse, Sissy kept it in his lap. His drink was so large that it was easier to hold it with both hands and he rested it on top of his purse. He didn’t really want it at all since he already had way too much to drink. It was dark in the theater, and would be darker once the show started. Could he possibly get away with not drinking it at all? He could just leave the cup behind when they all walked out. His problem was, that knowing Mel, she would probably find some way to check on him when the movie was over. But would she? Unable to decide what to do, and not wanting to drink anything at all, he kept the cup in his lap and did his best to ignore it for a while.
While they waited for the movie to start, Ray quietly told Mel one or two things about the movie that he particularly liked. Mel was tempted to ask which woman he had seen it with already – or how many women he had seen it with – but she refrained in the name of being polite. What did she care how many women he went out with? Like everyone kept telling her, it wasn’t like she was going to marry him!
She glanced a few times toward Sissy and Derek. As usual, it appeared as if they were both ignoring each other. She didn’t see Sissy drinking anything, but that didn’t mean he wasn’t. Ray was still occupying most of her attention. As the lights dimmed further in preparation for the movie to start, she looked over again at Sissy. His cup was still in his lap as if he hadn’t tried to drink anything from it. She leaned over and quietly said, “I expect that drink to be finished before the movie ends. I’ll be checking it later!”
Chad now had the answer to his question. As Mel leaned back in her seat again, he brought the large cup up and started sipping from the straw. Ugh!
They had to sit through several movie trailers of upcoming movies before the movie actually started. Once it did, Ray leaned over one more time to speak to Mel. Before talking, he reached over and took her hand, as if to emphasize what he was about to say. “I think you’re going to love this movie,” he said. He leaned back again, but Mel was quick to notice that his arm was still in her lap, still holding her hand. Wow, what an operator! Surprisingly, she didn’t shake his hand away or even complain. She just let him hold her hand.
The movie was slow to start and Chad noticed Derek fidgeting more than once in boredom and frustration. He sipped slowly at his drink every few seconds as the movie continued. But the further into the movie they got, the more interesting it seemed to get, and Chad was so used to sipping liquid almost constantly now that he was doing it without thinking.
One of the love scenes began in the movie. Mel was riveted. She was riveted that is, until she suddenly felt Ray’s finger, from the hand that was still holding hers in her lap, begin to move… and poke… and lightly rub against her crotch under her thin dress. She should have stopped him. She should have! But she didn’t. The love scene became more torrid, and so did the manipulation of his single finger. She couldn’t believe he was doing it! She couldn’t believe it! She also couldn’t believe that she was actually letting him. And… she couldn’t believe how turned on she was getting. Unfortunately, when the love scene ended, so did the manipulation of his finger. She breathed a silent sigh of relief – and wondered if there would be more such love scenes.
Ray couldn’t believe his luck. She hadn’t stopped him! She hadn’t even given him the slightest clue that she wanted him to stop. That meant… later! How long did this sappy dumb movie last?
Derek couldn’t get into the movie at all, classifying it as a typical “chick flick.” So he sat and fumed over how he had gotten himself into this mess in the first place. Well, at least Sissy… or Chad… or… whatever, had made the effort to look – decent tonight. In fact, he had obviously gone all out. He guessed that it was all part of his sudden – and weird – desire to become a woman. And he was obviously getting better at it because, fortunately, he really didn’t look too bad. Fortunately! He almost felt like he had gotten through dinner just fine – no embarrassment – other than the dancing of course. That had been stupid! He could have definitely done without the dancing! Sissy said it wasn’t his idea? He “usually” did everything Mel told him to? Damn! Couldn’t the guy get a little backbone?
This was the first movie Sissy had been to in a long time, and he was thoroughly engrossed in it. But he was engrossed on two levels. Part of him was relating to the guy in the movie… or guys in this case, and since he had been dressing, and for the most part, living as a woman for the last two months, part of him also identified with the female character. Surprisingly, the movie was well enough written that both sides were accurately portrayed. He could both understand and feel what the guys in the movie felt, while at the same time, he could also understand things from the female perspective that he had never realized before – or at least he thought he could. He was so interested in it all, that when he suddenly started sipping air though his straw instead of coke, the resulting noise actually startled him. “Sorry,” he said softly to Derek who had quickly looked over in annoyance.
Mel heard the gurgle from Sissy’s cup too and it seemed to pull her right out of her interest in the movie – for a moment. She quickly realized what the sound was, and with a feeling of satisfaction that Sissy had done as he was told, allowed herself to get right back into the movie. She was particularly interested because she suspected that another little “love” scene might be coming up – and she hoped she was right. Ray’s little finger had been all she could think about since the first one!
Ray, of course, knew that the scene was coming. Would she let him “play” a little with his finger again? He hoped so, because this time he planned to do a lot more exploring with more than just his finger – if she let him. But he was now fairly confident that she would. He wished he dared look at his watch to see how much longer this stupid movie was supposed to last. But he couldn’t do that. He couldn’t give the least impression that he wasn’t really interested at all – at least, not in the movie.
Mel felt Ray’s finger moving again, and the characters hadn’t even gotten to the bedroom yet! And then something happened in the movie to delay the love scene, yet Ray’s finger was still working. Then something else happened and the scene was delayed yet again. The frustration was building quickly inside of Mel and she realized her panties were getting wet. Damn. But it also felt so good! Then still something else happened in the movie to delay the inevitable and her frustration grew again! But this time, the delay in the movie made her think a bit more about what was going on. She knew that Ray wanted to make love to her tonight. And okay, right now she was more than ready to go along with that idea! But not tonight! It couldn’t be tonight! She had definitely decided that she wasn’t going to do this with him tonight! Besides, they had all come in Ray’s car, how would Derek get home?
Not surprisingly, things suddenly worked out in the movie and the two main characters finally made it to the bedroom – and of course the bed. And at that point, Mel felt Rays hand leave hers and start to wander further… a lot further… and… she let him. Maybe it was because of the panting she was doing – and trying to keep silent. Panting that was definitely growing since his hand was now under her skirt and was pressing against her wet panties. Oh! Oh! Oh! But in the middle of her “enjoyment,” she once again remembered that sex – at least between Ray and her – had to be out for tonight. Didn’t he realize that? How could he keep doing this if he knew that? Maybe he just wanted to get her so hot and bothered that she wouldn’t hesitate at going out with him again. Damn! It was definitely working too! Well, two could play at that game!
Ray couldn’t believe his luck! She was letting him explore her in the most intimate way. Tonight! Tonight! Tonight! He couldn’t wait! And then… and then… he felt her arm moving. For a moment he thought she was going to finally stop him, but she didn’t. Her arm wandered all the way over from her lap – to his! And he felt her hand groping and rubbing at the top of his leg. And then, it was moving higher, right onto… Oh my! Oh yes! Mmmm! He couldn’t believe it, while he was groping under her skirt, her hand was now massaging him through his pants. Making him grow. Arousing him even more than he had been before. What a woman! When would this stupid movie ever end?
Okay, that last part had been pretty good, Derek realized. In fact, the whole last part of the movie seemed to be pretty good. Much better than he expected. Damn! And now he had been so touched by it that there were tears in his eyes! He cautiously rubbed them so as not to give away the fact that he was “emotionally touched.” He hoped the movie would be over soon – and he especially hoped there would be nothing else that might “affect” him like that. It was embarrassing! Damn! And… shit… was Sissy actually crying next to him? Well, he supposed that figured. The guy did want to become a woman. He now guessed there might be more to that desire than he thought.
Sissy wept softly. He couldn’t help it. Yes, he knew he was a guy – underneath – and guys don’t cry, especially not during a dumb movie. But, he still couldn’t help it. The tears just seemed to roll down his face as he tried to cry quietly. He really hoped that Derek didn’t hear him. That would be even more embarrassing. Or would it? Derek did think he was trying to become a woman, and what woman wouldn’t cry over something like this? He could even hear little sounds coming from Mel next to him. Of course, she was leaning over toward Ray so it was a bit harder to tell. But he could hear – something from over there.
Mel mewed softly. Between the emotion of the movie making her cry, and the emotion of sexual excitement from Ray, she didn’t know what she was doing. She could no longer keep “manipulating” him. She had to bring her hand back to help blot the tears falling from both eyes. And as she did, she kept pressing her legs closed over and over again against Ray’s hand, trapping it inside, then releasing it. Again, and again. Damn. She was in such a state. He would have to do this to her! And tonight… she couldn’t! She wouldn’t! Damn!
The movie ended and Ray quickly pulled his hand back before anyone could notice. He also hoped that nobody would “notice” the prominent bulge that now had to be in his pants. Damn this was a fine woman! He couldn’t wait to get her into bed! The house lights came up and he looked over at Mel. She was crying – as expected. But he also noticed that her legs were pressed awfully tightly together too. Well, that was to be expected too. Past Mel, he could see Sissy still sitting there staring at the screen, crying like a girl. Stupid! Well, he wanted to be a woman, so he supposed it was only right – now. He caught a quick glimpse of Derek looking over at Sissy. They locked eyes for just a moment and the usual male message was instantly transferred. Typical women! They’d cry over anything!
Sissy leaned over and chanced talking to Mel. “I can’t believe how much I enjoyed that,” he said as the tears still rolled down his face.
Mel almost laughed. “Me too!”

The Bet - Chapter 44 (Sunday – week 7 Part 7 of 9)

2011-11-22T02:43:00.001-08:00

The Bet
by Karen Singer

Chapter 44 (Sunday – week 7 Part 7 of 9)

Their meal came and Chad was pleasantly surprised to see how nice his salad was. He took some mental notes so he could do something like it at home sometime – not that he’d ever probably get to eat it. Baby food seemed to be his most likely dinner from now on.
Several times as he ate, he saw Mel glance and nod toward his glass of iced tea. He again got the message – drink, drink, drink! Ugh! And worse, since he was obviously drinking so much, the waiter kept coming by over and over again to refill his glass. He couldn’t even keep track of how much he was drinking! One thing he could tell though, was that his diapers were getting wetter and wetter. Well, hopefully, three diapers would be more than enough for tonight. Hopefully!
In the middle of their dinner, Mel started trying to make a conscious effort to involve Derek more in the conversation. But Derek’s replies seemed to be very few words and she quickly gave up. But Ray didn’t ever seem to run out of topics to talk about – with her.
They were just finishing dinner when Sissy saw Mel tapping her fingers against her lips again. He pulled his compact out of his purse and checked his face. Most of his face looked perfect, but this time there was no doubt he would have to refresh his lipstick. He had seen the lipstick stains all over his glass of tea and his fork had a fairly prominent showing of it too. He had tried to be careful with his napkin but that too was covered with red lip stains. He pulled the lipstick out and opened it. It wouldn’t have been so bad except that he saw Derek watching him intently. Under Derek’s scrutiny, he added a fresh layer of the bright red lipstick. He couldn’t believe how strange – and humiliated – he felt as he did it. Humiliated enough that he felt himself peeing in response – which only humiliated him even more.
Trying to make it seem totally normal, he finished up and put the lipstick and compact away. He saw Derek shaking his head a bit, then look away. Sissy wondered if he had done something wrong. Had he messed his lips up somehow? He opened his purse and quickly pulled his compact out to recheck his lips. Nope. As far as he could see in the tiny mirror, they looked just fine.
“You’ll have to excuse me,” Mel said to Ray. “But I need to make a quick trip to the ladies room.” She looked straight at Sissy. “Coming?”
Now Chad was more worried about his makeup than ever. He grabbed his purse and got up from the table and followed Mel toward the restrooms. Once inside, Chad didn’t quite know what to do with himself other than to check his face in the mirror. There was no way he was going to be able to use one of the toilets. While Mel went into one of the stalls, he checked his face closely. As far as he could tell, his face looked perfect – well, for what he was anyway.
Mel finally came out of the stall and checked her own face. As she pulled her own lipstick out, she said. “Put another coat of lipstick on.”
Chad was surprised, his lips definitely didn’t need it. “But…”
Mel looked quickly at him. “Don’t argue – just do it!”
Chad once again added another layer of the red lipstick. Then he put everything back in his purse again.
Mel was done with her own face before Chad was done with his. She waited till he was finished. “I want you to start talking more, especially to Derek. You two are so quiet it’s like you’re not even here!”
“But what am I supposed to say?”
“I don’t care. Just talk to him! Be the girl… and keep him happy!” She paused briefly and just looked at him for a moment. “Before we get out of here, I’m going to get Ray to dance with me one more time. Since I doubt that Derek is going to ask you, I want to hear you pleading with him to take you out on the dance floor!”
Chad’s knees almost buckled. “Dance with him?”
Mel just smiled wickedly in return and led the way back out into the restaurant.
When they got back to the table, Sissy noticed that his iced-tea glass was freshly filled once again. A never-ending source of tea – and too much liquid for his system. Talk to Derek? What the heck was he supposed to say? He knew perfectly well how Derek was feeling about this date! “We’re back,” he said cheerily to Derek as he sat down again.
“I noticed,” Derek replied as if he wasn’t very happy about it.
The waiter showed up then to ask if anyone wanted desert.
Ray looked around the table. “There’s still plenty of time before the movies start. How about it?” He looked directly at Mel. “And don’t tell me you don’t cheat on your diet at least once in a while!”
Mel laughed. “Well, maybe.” She was particularly interested because she wanted a reason to keep Sissy in the restaurant for a while longer so he could interact a bit more with Derek. She looked at Sissy. “What do you think?”
Chad was particularly surprised she would ask him – especially since he had only managed to finish half of the dinner he had gotten. Between his smaller compressed stomach and all the liquids in his system, he was lucky to have eaten that much. He smiled though as he replied, “Sounds great!” Actually, it was anything but great. He agreed with Derek. The sooner they got to a nice dark movie theater, the better!
The waiter cast another disapproving look at Sissy, then ignored him as he spoke to everyone else at the table, telling them about all the wonderful deserts they had available.
Mel was particularly interested in one of them but… “I’m not sure I can eat that much,” she complained.
“It doesn’t matter to me,” Ray replied. “Get it, and eat what you can.”
But Mel had a better idea. “Why don’t we get one and share it between the two of us?”
Ray smiled broadly at her. “I really like that idea.” He looked up at the waiter. “We’ll share one.”
The waiter nodded politely and turned to Derek.
“Nothing for me,” Derek told him.
Sissy saw Mel scowl a bit as Derek said it. He also saw her staring intently at him again – as if daring him not to order something. He was supposed to be talking to Derek. But he couldn’t! The waiter was looking at him now, waiting for his answer. The waiter didn’t look like he was smiling as much as he had when he spoke to everyone else. Oh well. Talk to Derek? “Derek,” he started, “why don’t we do the same?”
Derek looked over at him like he was crazy. “You go ahead and get what you want. I don’t want anything.”
Sissy saw Mel still staring intently at him. Then suddenly, he saw her glance her eyes quickly at Derek, then back again. Damn! She wanted him to keep trying. How? “Please?” he pleaded like a little girl to Derek.
Derek looked at him like he was even crazier. “I told you…”
“But… what could it hurt?” Sissy replied before Derek could finish.
Derek shook his head. “Oh, who cares!” He looked up at the waiter. “Bring one for us too. I probably won’t eat any of it though.”
The waiter nodded politely and was gone.
Mel seemed to be all smiles once again. “I saw a couple of deserts being brought out to some of the other tables. There’s no way I could ever eat all that! I think this is going to work out perfectly! Don’t you, Sissy?”
Chad was startled that she would even ask. “Oh… Oh yes. Perfectly!” But he was still more interested in getting out of the restaurant as soon as possible.
The musicians started in on another tune and Mel turned her head toward them. “Oh, I love that song!” She turned to Ray. “Let’s dance again!”
Her request came so fast that it caught Sissy off guard. He wasn’t ready for this! But he saw Mel staring at him as she got up out of her seat. Oh God he didn’t want to do this, but he turned to Derek. “Let’s dance,” he said.
Derek was clearly shocked. “What?”
“Let’s dance too.”
“You are crazy!”
Sissy shrugged. “Maybe… Probably… But so what? Let’s dance.”
“No!”
“Please!” Sissy pleaded.
Derek was clearly upset. “What the hell has gotten into you? I’m not dancing! At least not with you!”
Mel leaned over and spoke softly. “You’re raising your voice! Why don’t you just take her out and dance one dance, that’s all – before you bring more attention to yourself by arguing and causing a little scene.”
Derek looked up at her angrily. He wanted to yell. He wanted to argue! But, unfortunately she was probably right. He looked around at some of the other tables. A few people were looking at him. He threw his napkin angrily down at the table. “Oh, all right!” he grumbled in a much softer voice. He looked at Sissy. “Come on.”
Now it was Sissy’s turn to be shocked. He didn’t actually think that Derek would give in so quickly. And Derek clearly didn’t want to do this – just as much as he didn’t want to do it. But he got to his feet and “followed” everyone else down toward the dance floor. Fortunately, there were quite a few couples already dancing.
The music wasn’t slow, but it wasn’t fast either. Not fast enough that they could stand away from each other and just move around a bit. Everyone else on the floor seemed to be holding each other as they danced. Sissy had been aware of his super high heels with every step that he took, but the minute they touched the hard wood of the dance floor, he was more aware of them than ever. How was he supposed to do this? He couldn’t! He just couldn’t!
He and Derek just stared at each other for a moment, as if neither of them knew what to do. “Well, you wanted to do this,” Derek said as he held out his hand. Derek clearly wasn’t too pleased about it. Reluctantly, Sissy reached out his hand and allowed Derek to take it. It was his right hand that he had to reach out for Derek to take – the opposite hand he was used to using when he danced with his wife… make that ex-wife. Derek pulled him – a bit – closer… not too close. And they started trying to move to the music together. Derek was obviously trying to lead and Sissy was trying his best to follow, but he really didn’t know how. He felt so awkward and out of place.
The dance floor felt slippery under his super high heels. He had to be more aware than ever of trying to keep his balance. It was particularly hard since he was “supposed” to be moving which ever way Derek led him. He felt clumsy, clumsy, clumsy! And obviously Derek was having a harder time than usual too. “Sorry!” he said softly as he stumbled a bit and recovered his balance.
“Yeah, sure,” Derek replied noncommittally.
“Actually, this wasn’t really my idea,” Sissy told him.
“It wasn’t? You sure seemed to be awfully insistent back at the table.”
“Mel said I had to.”
Derek digested that for a moment. “Do you always do what Mel tells you to do?”
Sissy instantly thought about Robin and what she knew – now. “Usually,” he replied cautiously.
“Humph! Well, I guess she’s doing her best to make a woman out of you, but I think this part could have waited till later. A lot later!”
“I couldn’t agree more,” Sissy replied.
As they danced and talked, what they didn’t see was Ray continually snapping picture after picture with his cell phone. “You better make sure I get some of those,” Mel said to him.
“I’ll be glad to send them to you tomorrow,” Ray agreed.
The song ended and Derek was the first to leave the dance floor. Sissy had trouble keeping up with him in the heels he was wearing.
“You did good together,” Mel said to Derek and Sissy as she sat down at the table again.
“They make such a cute couple. Don’t they?” Ray added as he too sat down.
Derek rolled his eyes angrily, but made no other reply to Ray’s taunting.
Ice cream and brownies covered in chocolate sauce. Two huge bowls of it were delivered to the table, each one with two spoons already sticking out on opposite sides of the bowls. The waiter set one of them between Mel and Ray, and the other one between Derek and Sissy. The deserts looked so good, but Sissy didn’t feel much like eating any of it. He was about to reach for the spoon sticking out straight toward him when he was interrupted.
“Oh! Hey! Wait a minute,” Ray said as he got up from his seat.
Everyone looked up at him, waiting to find out what Ray wanted. Ray pulled out his cell phone. “I want a picture of this so we can all remember it!” It was the first time all night that he had brought out his phone to take a picture where Derek could see it.
“No!” Derek complained flatly, clearly not happy about it. “Don’t do it!”
“Oh come on!” Ray replied as he got the camera in the phone ready and held it up. “Lean in toward the desert a bit more,” he suggested.
“No!” Ray repeated firmly again.
“I’m going to take the picture anyway, so you might as well go along,” Ray told him. “Now lean in!”
Sissy, seeing Mel nod toward him, reluctantly leaned in – slightly – toward the elaborate dessert. Derek refused to move.
“Smile…” Ray prodded.
Derek’s jaw dropped wide open. “You can’t be serious!”
But Ray wasted no more time and snapped the picture.
“Can’t we just get out of here now?” Derek asked as Ray was sitting down.
“Why?” Ray replied. “We’ve still got plenty of time.” He happily picked up the spoon nearest him from his dessert and dug in. “Mmmm. So good!” he said.
Derek tried one bite of the dessert before sitting back and sulking about everything. Sissy ate a bit more, but not much. Ray and Mel on the other hand, ate a good bit of their dessert before Mel declared she couldn’t possibly eat another bite.
The waiter reappeared and asked if everything was going to be on one bill or separate. “The lady here and I are on one,” Ray replied.
Sissy was about to say that he would get his own, but Derek spoke up first. “I’ve got for us,” he said.
“Are you sure?” Sissy asked him. “I can pay for mine if you want.”
Derek shook his head. “No, you’re my date tonight. I’ve got it.”
“Thanks,” Sissy replied softly. He sat back and thought about it. He was the girl tonight, and even though it was only a little thing, Derek picking up the tab made him realize that fact all the more. How strange. And then he saw Mel giving him the signal to check his face again. Another layer of red lipstick had to be applied.

The Bet - Chapter 44 (Sunday – week 7 Part 6 of 9)

2011-11-18T02:54:00.000-08:00

The Bet
by Karen Singer

Chapter 44 (Sunday – week 7 Part 6 of 9)

Ray pulled his big Cadillac into one of the empty parking places as close as he could get to the stairs. “I guess this is it,” he said to Derek as he looked up at the apartments above. “Somehow I was expecting something a bit nicer since she’s supposed to be a lawyer.”
Derek wasn’t really the least bit interested. He wasn’t looking forward to this “date” at all. “Who cares,” he replied.
“Certainly not me,” Ray returned brightly.
They got out of the car, but before going upstairs, Ray opened the back door and pulled out a bunch of flowers along with a small white box.
“I still can’t believe you actually bought her flowers!” Derek said as Ray pushed the car door closed the again with his leg. “And what’s that, chocolates or something?”
Ray just smiled. “Or something.” He suddenly looked like he had a small problem. “Oh hey,” he said. “Can you hold this for a moment so I can lock the car?” He handed Derek the box while he pulled his keys out and locked the car. Derek tried to hand him back the box, but Ray asked him to please hold it for him till he could give Mel the flowers. Thinking nothing of it, Derek carried the box upstairs with him. He stood back while Ray knocked on the door. He really wasn’t looking forward this!

“I’ll bet that’s the guys now!” Mel said as she quickly removed the robe she had covered her dress with to keep it clean.
She took one more look at Sissy, then she smiled at Sandy who had been standing in the background watching. “Well don’t just stand there Sissy, our dates are waiting!”
Nearly shaking with dread, Chad went to the door and opened it… and got a bit of a shock. Ray was standing there, holding a bunch of flowers!
Ray was a bit surprised to see Sissy at the door. He had been expecting Mel to open it. “Uh… Is Mel here?” he asked as he stared somewhat surprised at Sissy. He was mostly surprised because Sissy looked – pretty good!
Chad started to curtsey automatically, and stopped himself halfway through. “Of course,” he replied as he stood back out of the way to let the guys in. Derek just stared at Chad as he followed Ray through the doorway. The problem was that Chad couldn’t tell anything from the look on Derek’s face. Derek didn’t smile, but at least he didn’t frown either. Finally, he saw Derek nod a bit and Chad felt a wave of relief.
“Are those for me?” Mel’s excited voice cut through the room as she saw the flowers in Ray’s hand.
“Of course,” Ray replied. “Beautiful flowers for a beautiful lady.” He bowed slightly as he held them out for Mel to take.
“Oh brother!” Sandy muttered half under her breath as she rolled her eyes.
As Mel took the flowers, she tried remember any date bringing her flowers before – and the only one she could think of was for her senior prom in high school – and that was a corsage. “They’re beautiful! Thank you.” She sniffed at the flowers. “And they smell so nice!”
Derek started to hand Ray the small white box he was still carrying. But Ray just looked at him like he didn’t understand. “What are you giving that to me for?” Ray said. “You brought that for Sissy.”
Now it was Derek’s turn to be confused. “But…”
“Just give it to her,” Ray encouraged as he pointed toward Sissy. “You don’t need my permission.
Confused, Derek automatically turned toward where he thought Sissy was standing, but Sissy had moved closer now so he could see the flowers that Mel had gotten. As Derek turned, the box hit Sissy’s arm and nearly fell out of his hand. “Oh! I’m sorry,” he said automatically.
Chad’s knees felt like they were buckling. “That’s… for me?”
Derek, still confused, started to turn back toward Ray.
“Just give it to her,” Ray said. “You brought it.”
“But I…”
“You brought something for me?” Chad asked, still trying to figure things out too.
“Um… I guess so,” Derek replied with more than a bit of annoyance. He handed the box to Sissy, then he looked back at Ray quizzically, but also with a bit of menace on his face.
Chad took the box and opened it. And got another shock. Inside, he saw a small grouping of white flowers. He removed them from the box and realized they were attached to a plastic armband. “Oh my God!” he exclaimed. “It’s a…”
“You brought her a wrist corsage!” Mel exclaimed. “How sweet!”
“But I didn’t…” Derek tried to say again.
“Well don’t just stand there, put it on her,” Mel coaxed.
“But…” Derek gave up and looked angrily at Ray again for a moment – who was smiling back broadly. Then he grabbed the flowers from Sissy. Sissy, his knees definitely shaking now, held out his left wrist and Derek pulled the plastic band wide and slipped it over Sissy’s arm. The minute he did so, a small click sounded from a few feet away as Ray quickly took a picture with his cell phone. As fast as he had pulled it out, Ray had his cell phone put away again and out of sight.
Chad stared at the flowers attached to his wrist – not believing that it had just happened. He felt so funny inside about it. Humiliated, yet… something else too. “Th… Thank you,” he stammered. Then, catching a glimpse of Mel out of the corner of his eye, he dropped a very nice curtsey and repeated, “Thank you.” When he stood up again, he noticed that Mel was smiling broader than before. Whew! He had found a way to get past that one!
“Why don’t I put those in water for you,” Sandy offered as she took the flowers from Mel. “You guys just go and have a good time tonight.”
Ray smiled broadly at Sandy. “Another beautiful lady in the apartment. I may have to think about moving here.”
Sandy rolled her eyes again. It looked like Mel was right about this guy. “Don’t bother,” she replied. “I’m spoken for.”
Ray just shrugged his shoulders as if he didn’t really care about that at all.
“You guys just go!” Sandy said, trying to ignore him. “You’re probably going to be late for dinner.”
“Good idea,” Mel replied as she headed toward the door. She glanced again up at Ray. He had brought her flowers, and she knew without a doubt that he had “arranged” for Derek to give the wrist corsage to Sissy. As she walked outside, she was reconsidering her feelings about Ray. He might be a two-timing sleaze, but he was also without a doubt very handsome. And after seeing how he had just manipulated Derek, she had a feeling that he might be more fun than she originally thought!
As Ray followed her through the door, he was immensely proud of himself for setting up Derek to give Sissy the flowers like he did. And seeing how Mel was dressed tonight, he was more determined than ever to get her alone in a “more intimate” setting.
As Sissy walked out behind Ray, he was still trying to come to grips with getting the flowers – and he still couldn’t believe he was about to go out on a date – with a guy! Derek no less! How was he supposed to do this?
And as Derek walked out, he berated himself for being such a sap and a pushover that he let Ray get him into this position in the first place! He just thanked his lucky stars that Sissy looked fairly good tonight – almost surprisingly so. At least he wasn’t dressed like a hooker again!

Mel sat with Ray in the front seat of his car while Derek and Sissy sat in the back – together. As Ray pulled the car out of the apartment project and into traffic, Derek said softly to Sissy, “Thanks for at least looking decent tonight. I appreciate it.”
“No problem,” Sissy replied, just as softly. “Actually, I’m much happier dressing like this than what I wore to the poker game.”
Derek grunted. “If nobody looks too closely, they might even think I’m out with a real woman tonight.”
Chad blushed. “Thanks,” he replied. “I’ll still be happier when it’s over.”
“Me too!”

The restaurant Ray drove them to was one of the nicer, more expensive restaurants in the city. “Isn’t this a bit much for just a dinner and movie date?” Mel asked as he parked his car.
“Not really,” Ray replied. “Besides, with the way you’re dressed, I figured you probably didn’t want to go to a movie anyway. From here we can go to a nice club somewhere and really enjoy ourselves.”
“Not on you life!” Derek called from the back. “I’m not going clubbing with Sissy as my date!”
“Now, now, be kind,” Ray replied. “I think Sissy looks pretty good tonight too.”
“Then you date him!”
“Ah, ah! A bet’s a bet! And you lost! Besides, I’m looking forward to showing off what a super dish Mel is.”
“No club!” Derek repeated firmly. “I want a nice, quiet, dark, movie theater!”
Mel put her hand on Ray’s arm. “I think it would be better if we all just went to a movie tonight like we planned. That’s all this bet was for. Maybe next time we can go somewhere else.”
“We can let Derek and Sissy go to the movie while we go someplace better,” Ray suggested to her.
Mel shook her head. She knew it was better tonight if she kept an eye on Sissy the whole time. Besides, she had some tiny little “plans” for him tonight. “Not tonight. Just a movie and that’s it.”
Ray was clearly disappointed. “Well, you went to a lot of trouble getting all dressed up just for a movie. I didn’t want to waste it.”
Mel smiled. “Think of it as giving you a reason to ask me out again.”
Ray smiled. “Now you’re talking!”
A small unintelligible grumble was heard out of Derek from the backseat.

Chad felt strange as he walked beside Derek, behind Mel and Ray, toward the door to the restaurant. His very high heels made a loud distinct clicking sound with every step he took – a lighter, more noticeable sound than Mel’s shoes made. The wrist corsage felt strange on his left arm. He had to be very aware of the flowers sticking up from it so he didn’t hurt them. His new clutch also felt strange in his other hand. It kept brushing the full skirt of his blue dress as he walked. Did he look enough like a woman tonight? Silly question. It didn’t really matter. Mel would make him go through this no matter what!
For the first time since before the guys arrived, he thought about his diapers. He had been so preoccupied that he hadn’t been noticing if he was wetting himself or not. He knew he had to be. He was sure his diapers were probably fairly wet already, but the huge bulk of all three diapers made it hard to tell anything at all. It was just another little something he would have to worry about later.
Since Sissy and Derek hung back a bit, behind Ray and Mel, the hostess didn’t really notice Sissy all that much when they walked in. As they were being led to their table, Mel noticed something that might be helpful, the waiters were going around and automatically refilling all the iced-tea glasses. She hung back a bit so she could whisper to Sissy. “Order the iced tea with your meal tonight!”
The table was square and Mel and Sissy wound up sitting across from each other. Chad was glad because it meant that Mel wouldn’t be able to lean over and whisper any more little commands to him. When the waiter came by with the menus, Ray ordered a glass of wine for everyone. Sissy looked questioningly at Mel, but Mel only brightened at the wine suggestion and said it sounded great. Sissy wasn’t sure, but he thought he heard Derek softly grumble again.
As they looked over their menus and waited for the wine, Sissy and Derek were both quiet, but Ray talked animatedly with Mel. If Chad didn’t know better, the way Ray was acting, he and Derek might not have even been there. The wine arrived, was approved by Ray, and was poured for everyone. They each took a small sip before the waiter began asking for their orders. There had been a lot of really interesting entries on the menu – all of them extremely high priced – and Sissy had been planning on ordering one of the steaks. Something like that to chew would have tasted great. He might not be able to finish it all, but it still sounded good.
The waiter started with Mel, who surprisingly ordered only one of the exotic dinner salads on the menu along with a cup of coffee. “That’s all you want?” Ray asked with some surprise. “You can have anything you want.”
Mel shook her head. “I still have to watch my figure,” she replied. Then she looked straight at Sissy as she added, “Everything on the menu sounds so good, and also so fattening!” Ray only chuckled, and said nothing else about it, but since she had been looking straight at Sissy when she said it, Sissy got the message clearly.
The waiter moved on to Sissy next, and for the first time looked at him more closely. It took him two seconds for his brain to register that there was something different about her. A moment later, total realization set in, and once he noticed it, he couldn’t help not seeing Sissy as a man dressed up like a woman. All further pretense went totally out the window when Sissy opened his mouth and spoke in his “girly” voice. Sissy ordered the same thing that Mel was having, except as Mel had dictated, he got iced tea instead of coffee. When he was done ordering, Sissy saw the waiter just staring at him for a moment. Un-approvingly? He wasn’t sure, but that’s the impression he got. Fortunately, the waiter moved on to Derek next and didn’t say anything else.
When the waiter left, Mel and Ray continued to talk while Sissy and Derek just listened. A few times, Derek and Sissy looked at each other, both of them silently acknowledging the awkwardness of the situation. Sissy kept sipping at his wine to help pass the time. As he did so, he couldn’t help but notice the red lipstick stain on the rim of his glass. Each time he picked it up, he tried to drink from the same spot so as not to spread the stain any further.
A few minutes after the waiter left, unexpected music filled the room. From where they all sat, they could just see two musicians up on a stage providing soft entertaining music. There was a woman playing an electronic keyboard, and a man with her who was accompanying her with a string bass. They both sang and together and they sounded surprisingly good. Sissy was glad to see the musicians. It gave him something else to concentrate on instead of the strange situation he was in. Not only that, but maybe everyone else in the restaurant would be paying more attention to the musicians too – and less attention to him. After a few minutes, Sissy noticed one of the couples closer to the musicians get up from their table and start dancing. He smiled. How nice. They were quickly joined by another couple from another table.
Sissy’s glass of wine was about three quarters done when he saw Mel looking at him again. Ray was talking and Mel appeared to be listening, but Sissy saw her rest her elbows on the table and her chin in her hands for a moment. Ray obviously thought nothing of it. But when Mel began tapping her finger against her own lips while looking at Sissy, Sissy got the message. Even sitting across the table from him, she was finding little ways to give him orders! He opened his purse and pulled out his compact and checked his face in the mirror. He decided everything still looked good, including his lipstick, so he put the compact away again. He saw Mel smile briefly at him. As far as he could tell, Derek hardly noticed – or at least he made no reaction. And Ray was still talking to Mel and probably never even saw him do it. Sissy picked up his wine glass and emptied it!
“Shall we dance?”
Mel was startled by the sudden suggestion. “Here? Now?”
“Why not?” Ray replied. “There’s plenty of room in front of where the band is playing.”
Mel looked and saw three or four couples dancing now. “Why not?” she suddenly decided and got up from her seat.
Sissy saw Ray look briefly back at Derek as if taunting him. Derek’s face didn’t look all that happy about it as he watched them heading toward the music. They were alone in the restaurant – together. Awkward! Awkward! Awkward!
Not wanting to watch Ray dancing with Mel, which would only be like him rubbing things in, Derek looked away from the dancers, which really left him only Sissy to look at.
“So far, so good,” Sissy said, trying to fill the awkward silence.
Derek grunted, but nodded his head. “Yeah, so far.”
Wanting to continue the conversation, Sissy added, “It’s a nice place. I’ve never been here before.”
Derek shrugged. “I’ve been a few times, but it’s been a while.”
Sissy didn’t know why, but he suddenly thought about Robin. Obviously, she hadn’t told anyone yet – or at least the word hadn’t gotten to Derek yet. “I’m more worried about tomorrow,” he said.
“Tomorrow?”
“At work. What’s everyone going to be saying?”
For the first time, Derek smiled. “I’m not going to have to worry about that, because I’m not going to be there. I’ll be flying out early tomorrow morning.”
“You’re lucky!”
Derek nodded. “About that anyway.”
“I’ll have to put up with all the women asking me tons of dumb questions.”
“You’re the one who wanted to be a woman! Don’t complain to me about that!”
Chad considered telling him how wrong he was, but all he could really do in the situation was to smile and say, “I guess your right.”
“You are getting better at it,” Derek said.
Chad felt himself blushing slightly. “Thanks. I’m trying.”
“But you’ve still got a long way to go!”
That kind of knocked the wind out of Chad a little. “Like I said, I’m trying.”
As they talked, they didn’t see Ray and Mel coming back from the dance floor and stopping a short distance away. Ray pulled out his cell phone again and took another quick picture as Mel giggled.
Derek and Sissy were saved from further conversation as Mel and Ray came back and sat down again. And once again Ray dominated the conversation – with Mel. Two minutes later, Mel was tapping her lips and Chad had to check his makeup again. Nothing had changed! How could it?

The Bet - Chapter 44 (Sunday – week 7 Part 5 of 9)

2011-11-15T02:45:00.000-08:00

The Bet
by Karen Singer

Chapter 44 (Sunday – week 7 Part 5 of 9)

Chad spent the afternoon thoroughly cleaning the apartment, doing laundry, and drinking more bottles than ever before. He was going crazy trying to get his diaper leaking faster. He had to! Mel had decided that she would only give him five swats from her stick for each minute over now, but if it looked like that wasn’t going to be enough, then she had no trouble raising it to ten.
While he was working, Mel was working too, but not on her computer. She had made tea yesterday, but he was going through the bottles so fast now that she had to make more to keep up. Not that she was that worried about the tea because he was also drinking a lot of water too.
As they both stayed busy, Mel kept her stick nearby – always. Whenever she thought he was least expecting it, she would order him to show his diaper, which always resulted in her giving him a quick stinging swat with her stick. And over and over again she pressed him to curtsey constantly. If he didn’t, then that brought another instant stinging swat.
Chad was getting more and more paranoid all afternoon. He kept a constant watch for Mel out of the corner of his eye. Just to avoid getting hit more, he started curtseying every time he saw her turn to him. She was already forcing him to curtsey every time he opened his mouth. And now he was doing it every time a conversation ended. It was very bothersome – to say the least.
He was fortunate to have his next diaper leaking on time. But he was only halfway through his next time limit when the stupid suppository, that he only thought Mel had put up inside of him, decided to go to work. Instead of changing him there, Mel sent him back to his own apartment to shower and make sure he was perfectly shaved all over before coming back again in a clean diaper. She wanted him freshly cleaned and shaved because the time to start getting ready for their date was getting closer.
When Chad came back, still in his maid’s uniform, he began worrying about what Mel intended as far as his diaper leaking later – during their date. Even if he got his current diaper leaking on time, which he was fairly sure he would, then what about the next one? By his estimation, the next one would have to be leaking sometime during the date. Surely she couldn’t expect him to have a leaky diaper then – could she? But then he remembered how obsessed she seemed to be about it lately – obsessed enough that he had been having trouble out in public on several occasions. And not always just a little trouble, at times it had been major trouble! So what was she expecting him to do tonight? He just couldn’t see himself having to change his diaper in front of Derek… or Ray either! If it came to that, he was sure he’d rather receive any punishment she might dish out, just so they wouldn’t know! If they didn’t know already. But that was another problem he had to worry about. Hopefully, Robin hadn’t told anyone yet. Hopefully.
So what did Mel expect for tonight? The thought bothered him so much that he finally approached her – and curtseyed as well as he was able to before he spoke. “Mistress…”
Mel looked up from her laptop. “Are you leaking?”
He curtseyed. “No, Mistress.”
“Show me your diaper!”
As fast as Chad could, he grabbed the skirt of his maid’s dress and pulled it up high. But by the time it was fully up, she was already coming out of her chair with her stick. He got a sharp slap on the side of his bare leg as punishment for being too slow before she sat down again.
“If you’re not leaking, then why are you bothering me?” she asked.
Chad pulled his dress down again and smoothed the skirt slightly before dropping yet another curtsey. “I… I was wondering about later,” he stammered.”
Mel was confused. “Later? We’re going out on a date later. What are you worried about?”
His curtsey was almost automatic. “My diaper leaking.”
“You’re worried you won’t make it?” Mel actually smiled. “Good! I’m glad you’re worried about it. Just make sure you get plenty to drink as often as you can tonight and… hopefully… you’ll be just fine. The restaurant really shouldn’t be much of a problem, but the movie theater… Maybe you should get an extra large drink before the movie starts.” She smiled broader. “In fact, I’m going to insist on it! Maybe Derek will even buy it for you!”
Chad actually shuddered at the thought. He almost spoke without curtseying again, but stopped himself long enough to complete the act just in time. “No, Mistress. That’s not what I meant. What happens when my diaper does leak?”
Mel’s face was still all smiles. “I’m so glad you’re actually planning on it. That makes me very happy! We’ll just have to wait and see what happens then… and deal with it… or not.”
Deal with it… or not? He couldn’t believe it. She was actually planning on him having a leaking diaper – during their date! He couldn’t! He just couldn’t! But… how was he going to prevent it? He was drinking so much already – and had been all day long. His system was so overloaded with fluids that even if he never drank another drop all night, he’d still probably be peeing constantly. And with the amount of time they were probably going to be gone, there was going to be no way to avoid it!” He actually shuddered at the thought as he dropped another curtsey and turned away from her in shock. He couldn’t believe it! He just couldn’t believe it! But what choice was he going to have? And then he realized that he had been set up. She had been pushing him extra hard all day, making him drink far more than ever. No matter what he did, there was no way he could avoid going out tonight and not having his diaper leak – probably over and over again. What were Derek and Ray going to think? What was he going to do? It was going to be… a disaster!
Mel continued to smile as she watched him walking away – obviously in shock. The funny thing was though, that he had asked the wrong question! She almost laughed. She was having so much fun today with him. Obviously, she was in a really wicked mood as far as Sissy was concerned. And she didn’t see any reason at all to stop.
An hour later, Chad looked up as he was folding laundry and saw Mel heading into her bedroom. What surprised him was that she closed the door behind her and he heard the faint sounds of her locking it too. He glanced at the clock and guessed that she was probably going in to get ready for tonight. Was he really going out on a date tonight? With Derek? As a girl? The thought still sent shudders down his spine. And what about his diaper leaking? He had purposely cut back on the amount he was drinking, but he was still peeing an awful lot and his diaper was getting awfully wet – already. Too soon in fact! He figured that it would be better if he was changed just before they left in order to put off leaking as long as possible. But if his diaper leaked too soon now, then what was going to happen?
He finished folding the clothes and looked around. He had a few things that he had just folded that needed to be put away in Mel’s room, but he couldn’t get there. The apartment was already spotless and even the kitchen was back in order again – the new order he had given it. So now what was he supposed to do? He was startled as Mel’s bedroom door suddenly opened and she walked out wearing only a full slip and headed toward the bathroom.
Mel paused on her way to the bathroom and saw Sissy just standing there near the laundry. But he wasn’t drinking anything and he didn’t appear to be working. “Show me your diaper!” she commanded quickly.
Chad raced to get his skirt up on time. But he knew before he started that he had failed. He especially knew it when he saw her hurrying to find her stick. A moment later, he was enduring not just one, but two hard stinging slaps from it. “What are you doing?” Mel asked. “I haven’t seen you drinking a bottle in a while now.”
Chad curtseyed. “I just finished folding the laundry,” he replied.
“And how about your bottle? You’re not leaking yet.”
Again he curtseyed. “I still have plenty of time,” he replied.
“I don’t care! Go get another bottle. What else are you doing?” she asked.
Chad curtseyed. “I just finished here,” he replied.
“Then get your bottle and get up on your perch and stay there till I’m ready for you. And your bottle better be long gone before then!” She glanced at the clock again. “We don’t’ have much time before we have to start getting you ready!” She saw him just stare at her for a moment. “Now go!” she commanded with a half-hearted swing of her stick that again caught him on the side of his leg. “And if you start leaking while you’re on that thing, just stay there and don’t bother me!”
Chad turned and started to hurry away, only to feel her stick hitting him one more time.
“You forgot to curtsey again before you left!” she yelled angrily.
Chad quickly dropped yet another curtsey, then hurried to the kitchen to get another bottle – of water this time. Mel was already in the bathroom by the time he emerged from the kitchen, bottle in hand. He was glad to see her gone! He reluctantly climbed up onto his perch and carefully brought the bottle up to his mouth. With his neck bent back and his body leaning into the corner, he started drinking again. Another bottle! How was he going to keep himself from leaking during the date? It was going to be impossible! He suddenly felt himself peeing again, but it had been such a short time since he had climbed up onto his perch that it held very little interest for him this time.
Having no other stimulation to occupy his mind, his thoughts naturally tuned toward the upcoming date. He was going as the girl this time. He was going out with Derek – his friend! At some point – possibly more than one time before they got back, his diaper was going to start leaking. And worst of all, before the date ended, he was supposed to kiss Derek goodnight – passionately! He couldn’t! He just couldn’t!

Mel left her dress and shoes off, but otherwise she was all ready. She walked out of her bedroom and straight over toward Sissy who was still in the corner on his perch. The empty bottle was still in his hand and down by his side where it belonged. She looked closely at the bottom of his diaper – it looked like it had just started leaking. Perfect!
Without saying a word to him, she left him and found her phone and punched in a number. “Hi Sandy? I just have to run and get him a few things from his apartment. If you want to come over in about fifteen minutes, we should be ready for you then… Great!”
Ignoring Chad completely, she threw a robe on over her slip, grabbed her keys out of her purse, and went out the door. The walk to his apartment was short and she was inside in only a minute. She went straight to his cardboard dresser where she got the few things she wanted. She was back home again a few minutes later. As far as she could see, he hadn’t moved. Actually, this time, she really didn’t care.
“Okay, Sissy. Let’s start getting you ready.”
Chad gratefully climbed off of his perch and stretched his ankles and legs for a moment. Then he went quickly into the kitchen to deposit his now empty baby bottle. He found Mel waiting for him in her bathroom – with another diaper for him. He wasn’t all that happy to see only one diaper in her hand again.
Mel had him remove his maid’s dress before she expertly removed his soggy diaper and did her best to clean him up. Then she added a layer of baby powder and smoothed it all over his front and backside. Then she finally pinned the fresh diaper in place. “An hour and forty-five minutes, Sissy,” she told him.
Chad still couldn’t believe it. What was he going to do? Especially since he realized he was peeing yet again. His dry diapers never stayed that way very long anymore! An hour and forty-five minutes! They would be in the middle of their date then. What would they be doing? Where would they be? He only hoped that they would be inside the movie theatre by then so that when it happened, nobody could see it in the dark. But what about after the movie – when his leaking would be much worse and that much more obvious? It was not a happy subject to dwell on.
“Sit on the toilet there,” Mel said as she pointed to it, “so I can do your hair.”
Chad was a bit surprised by that request, although it was only practical. It’s just that… he hadn’t done anything with a toilet – other than cleaning it – for a long time now. He put the lid down that Mel always kept up, and carefully lowered his already wet diapered bottom down on top of it.
Mel attacked his hair with her brush. It really wasn’t too bad at all, but she grabbed her curling iron and started reworking it anyway. Before she finished, she heard Sandy at the door. She left Sissy right where he was, holding the hot curling iron in place, and went to open the door. “Your timing is perfect,” she told Sandy as she let her inside.
Sandy came inside with a bag full of makeup. “Where is he?” she asked as she looked around.
“In the bathroom – sitting on the toilet.”
Sandy was startled. “He’s what?”
Mel laughed. “Don’t worry. He can’t do anything there. I’m just working on his hair.”
Sandy was a bit relieved. For a minute there she had thought that Mel might have let him out of his diapers! “So do you think he’ll need the smudge proof stuff this time?” she asked.
Mel considered that for a minute, then smiled. “No. In fact, I’d like him to be fussing with his makeup as much as possible tonight. So… lots of lipstick this time. And something that he can reapply often.”
Sandy giggled. “No problem!”
While Mel worked on his hair, Chad had to endure Sandy working on his face. Between the two of them, he didn’t know which way to move his head or where to look – or not look. He soon felt himself peeing yet again – which was really strange because for once he was sitting on the toilet while it happened. Unfortunately, he might as well have been sitting anywhere else, because with his diaper on, there was no place else for the pee to go. At the rate he was peeing now, how far into their date would he be before he started leaking?
Mel finished with his hair and sprayed it lightly with hairspray while Sandy stood back to check to see what still needed to be done. When Mel had finished, Sandy grabbed the lipstick one more time and put another coat on top of the two coats that were already there. She stood back again to eye him critically. Finally, she nodded. “There! I think that should do it!”
Mel was pleased. “Perfect!” she declared.
“Can I look?” Chad asked hesitantly from his seat on the toilet.
“Sure, have a look,” Mel replied.
Chad got up from where he was sitting and turned to look at his face in the mirror. He was actually a bit afraid to at first, but when he got there, he got a pleasant surprise, he looked… great! Well, fairly great anyway. As good a job as Sandy had done, when you looked close, there was no doubt at all that underneath it all he was still a guy. But still… he didn’t think he had ever looked this good before. Or… this sexy either. If you could call him that. Maybe it was just the makeup. With the bright red lipstick she had used, he thought he looked more like a girl heading out to a club somewhere than just to a movie.
Mel picked up the lipstick that Sandy had used on him a moment before. “Take a good look, because now you’ve got to keep it looking just like that, all night. I don’t want to see anything the least bit smudged or out of place – especially your lipstick. I want you checking it often, and refreshing it almost every time!”
Chad’s eyes went wide as he felt a tiny bit of stirring to his sexual excitement. He took the tube of lipstick that Mel was holding out for him. Fortunately, he didn’t have to use it yet.
“Are you ready to put his dress on him?” Sandy asked.
Mel stepped out of the bathroom to check the clock, then turned back again. “No, let’s wait a few minutes. There’s still almost half an hour till they’re supposed to get here.” She looked directly at Chad. “Plenty of time for you to have one more bottle!”
Chad nearly died. He was peeing so much now that he didn’t know what he was going to do during the date. He started out of the bathroom, but was stopped by Mel’s angry voice. “Sissy! You didn’t curtsey again!” She quickly looked around for her stick, but it was nowhere near. Instead, in the heat of the moment, she reached out to slap him, but stopped herself just in time. She didn’t want to mess up the makeup job that Sandy had so artfully done. “Remind me to punish you for it later! Now go get another bottle and get back up on your perch!” This time, Chad curtseyed before he hurried out – while Sandy giggled at him.
While Chad stood up on his perch in the corner, “reluctantly” drinking yet another bottle of water, Mel finally put her dress and shoes on to finish getting ready. Sandy appropriately ooed and ahd over it. But as soon as Mel was ready, she put her robe back on over her dress again to keep it clean. “Sissy…” she called. “Are you done with that bottle yet?”
“Almost, Mistress,” Chad called back from his corner.
“Well, we can’t wait any longer. You can finish it later. Get yourself over here right now.”
Chad gratefully pulled himself out of the corner and set his bottle down next to his perch. He hurried over to Mel and curtseyed. Mel pulled him into the bathroom again and had him lay down on the floor. While Chad was laying down, Mel got out three more disposable diapers and started preparing them while Sandy looked on. Chad was elated to see them. She wasn’t going to send him out in only one diaper after all! A few minutes later, Chad was once again happily well protected with three full layers of disposable diapers on him. Then Mel handed him one of the all-in-one girdles he wore to work every day, followed by a pair of pantyhose. A few minutes later, Chad was pulling his new blue dress on and fastening his new shoes on his feet.
Mel grabbed the perfume she had brought back from his apartment and sprayed a tiny dose on his neck and wrists. “There,” she teased, “Now Derek will find you irresistible!”
Sandy and Mel together loaded his new clutch purse for him with everything he should need, but instead of putting the tube of lipstick in it, she handed it to Sissy. “Your lips are all smeared from the bottle you just drank,” she told him. “Fix it!”
Chad curtseyed before he took the lipstick and hurried to the bathroom where he touched up his lips – which seemed to be already coated with more lipstick than he ever used.
Mel followed him back into the bathroom to watch. “Don’t forget,” she reminded him as he applied a fresh coat, “I want to see you checking your face and touching up your makeup all night!”
Chad half curtseyed again as he worked. “Yes, Mistress.”
Mel stared at his reflection in the mirror. “I guess tonight is going to be a bit different for you.”
Chad bent his knees a bit as he worked on his lips. “In what way?”
“Tonight… Tonight I want you to try to be as much of a woman as you can. Use your girly voice, don’t call me Mistress in front of your friends. Try to enjoy yourself. Forget you were ever a guy. You’re not anymore. Be the girl!”
Chad’s eyes went wide as he looked back at her in the mirror. He turned toward her and curtseyed. “I don’t know if I can,” he said nervously.
“Try,” Mel replied. She smiled at him. “You look very nice tonight.”
Chad curtseyed more nicely this time. “Thank you, Mistress.”
Mel smiled. “I really do love seeing you curtsy like that.” A sudden thought struck her. “In fact… I’ll bet Derek would like to see it too.”
Chad was horrified. Curtsey for Derek?
But Mel wasn’t done yet. “At least once tonight, I think you should curtsey nicely for Derek. And make sure I see you do it!”
The horror over that command was still registering when someone knocked on the door!
Mel smiled. “I’ll bet that’s the guys now!”

The Bet - Chapter 44 (Sunday – week 7 Part 4 of 9)

2011-11-11T02:39:00.001-08:00

The Bet
by Karen Singer

Chapter 44 (Sunday – week 7 Part 4 of 9)

He had only been six minutes late. Six minutes! That’s all. If she had kept his time limit at two hours he would have made it easily! But an hour and forty five minutes? It was too short! Sometimes he could make it, but sometimes his diapers could be awfully stubborn and decide not to leak in time. It wasn’t his fault, it was the diapers! The diapers and… the too short time limit. Maybe she just liked beating him? Maybe.
Chad finished spreading the diapers out on the floor to protect it just as Mel came walking up, her stick still in her hand. Not taking his eyes off of the stick, he curtseyed nervously, even though he didn’t have anything to say. He wasn’t looking forward to this – even though it wasn’t all that many swats that he would be getting.
Mel smiled at his nervous curtsey, even though he didn’t say anything. As far as she was concerned, the more he curtseyed, the better – reason or not. “Okay, Sissy. Get that diaper off. Let’s get this over with.”
Chad wasn’t sure if he needed to curtsey or not. He hesitated, than curtseyed – just in case. He pulled the skirt of his dress up high again and left it there. Then he started unfastening his diaper. As usual, it was soaked as it dropped heavily to the floor. But then, they were always soaked – thoroughly. He hated having to do it, but seeing Mel standing there waiting with her stick in her hands, he got into position, leaning up against the back of the chair. Hating this part even more, he braced himself and purposely raised his naked butt up as high as he could, making it an inviting target for her wicked stick. Unfortunately, he didn’t have to wait very long. He heard the swoosh of the stick just a bare second before he felt the stinging pain erupt across his backside. Ouch! That hurt! It was all he could do to keep his hands off of it and not rub it. He stood up and curtseyed. “Thank you, Mistress,” he said in his sissy voice. Then he got back into position for the next one. Ugh!
“You know, Sissy,” Mel said as she waited for him to get ready again. “I wonder if we’re being too easy on you.” She saw him raise his backside again. She swung her stick – hard! Smack! She had to wait till he stood up and thanked her.
Chad didn’t know what to think. Too easy? In what way? Not in any way that he could see. He curtseyed. “Thank you, Mistress.”
Mel watched him getting back into place. His backside already bore the distinct red marks from where she had hit him. “I’m thinking that one little stroke from my yardstick is not nearly enough to give you more incentive to try harder.” Swoosh… Smack!
It was all Chad could do to not cry out in pain as the stick made its stinging impression on his already flaming backside. Little stroke? That hadn’t been a little stroke at all! Not one bit. It hurt! What was she thinking – not enough incentive? “Thank you, Mistress,” he said in a rather husky sissy voice – after his curtsey. He was already fighting back the tears.
Mel saw the look of alarm on his face as he thanked her, then started getting into position again. Good. “I’m thinking that we need to double the number of strokes… No… I doubt that would be enough either.”
Chad was already panicking. Double? And even that wasn’t going to be enough? What was he going to do? It was already too much! Swoosh… Smack! Ouch!
“I wonder if five would be enough,” Mel mused out loud. She clearly saw the panic in his face as he stood up and curtseyed. His thank-you sounded even worse than usual since he actually stuttered as he tried to say it. “Five smacks from my stick for each minute that you’re late.” She watched as he got back into place again. “That would be… Let me see… For the six minutes this time… Thirty swats!” Swoosh… Smack!
Chad barely had time to register thirty swats before the stinging pain once again erupted on his tender backside. Five swats for each minute? It was way, way too much! He curtseyed again. “Thank you, Mistress,” he blubbered. But his thoughts were more on trying to contemplate five strokes for each minute over. Thirty swats?
But Mel was still musing things over to herself. Only she was doing it out loud. “Or maybe ten strokes for each minute would be better?” She paused as if to consider that idea. “Yes! I really like that number better.”
Panic was setting in full force inside of Chad as he raised his backside up for her to hit… which she did immediately. Swoosh… Smack! He wasn’t sure which registered worse, ten strokes for each minute, or the pain from her latest blow. He stood and curtseyed, noting that the tears were starting to leak out of his eyes. “Thank you, Mistress.”
Mel paused to look at him seriously. “By my count, that was six strokes already Sissy. What’s the rule? What didn’t you do?”
It took Chad a moment to realize what she was talking about. Unfortunately, he remembered all too soon. He almost spoke without curtseying again. But fortunately, he remembered just in time. “I didn’t pee during my punishment, Mistress. Five more strokes.”
Mel smiled. “That’s right! And don’t forget, I owe you four more for not curtseying earlier too.”
Four more too? That would make a total of… fifteen! And there was nothing he could do about it. He curtseyed before he said, “Yes, Mistress.”
Mel watched him getting back into place again, ready for his next set of swats. “I think I like this rule,” she said before delivering the next blow. Swoosh… Smack! “Five swats for not peeing during your punishment. Actually, I think that’s very reasonable of me. Don’t you?”
Chad curtseyed. “Yes, Mistress,” he stammered. “Thank you, Mistress,” he also squeaked out before getting back into place again.
Mel smiled. “Now… Now we just have to figure out, what should be the proper punishment for each minute that you go over. Five swats… or ten.” Swoosh… Smack!
By the time that Mel had delivered all fifteen strokes, Chad was crying uncontrollably. But the bigger issue on his mind was whether Mel would decide on five strokes for each minute over, or ten. She had only given him fifteen strokes this time and his backside was on fire. He didn’t need any more incentive. He was already doing everything he could to get his diapers to leak. What more could he possibly do? He stood up after her last stroke and curtseyed. He thanked her – sort of… What came out of his mouth wasn’t exactly intelligible. And then he realized that he was peeing again… way too late. He wanted to cry all over again just for that!

Chad stared at the corner – seeing… nothing. His backside still stung, but only a bit. It seemed to hurt worse because before she had put another diaper on him, she had stuck another miserable suppository up inside of him. Yuck! Just once he’d like to go without one! Just once!
He knew that Mel was in the kitchen eating the salad he had made for her. He had finished making it after she had diapered him again. And his own lunch? His lunch was already sitting out on the counter, waiting for him… sort of. Mel had made him pick out what he wanted to eat for lunch – from the baby food cabinet only – and put it all the jars out on the counter so she could approve them. By having to pick it out himself, he felt a bit like she was trying to make him humiliate himself.
And now… now he was stuck back in his corner again. His wonderful little corner… not! Stuck standing on his stupid “perch.” Perched… like a bird in a cage. Only there was no cage around him, just two walls that he couldn’t move away from. He guessed the walls formed a cage of sorts. He certainly couldn’t get away from them. Stuck!
There were so many other things he could be doing! Useful things! Necessary things! Like laundry! He was still way behind with that. And cleaning… cleaning anything and everything. But instead, here he was, put away. Out of sight and out of mind. Not allowed to move a muscle. Not allowed to make a sound. Not allowed to see anything. He supposed he was lucky that she didn’t put earplugs in his ears so he couldn’t hear either. He wasn’t about to mention that because it might give her ideas.
Stuck, where the only stimulation he had was what his body felt. Like how much his legs ached after a while. Or how much his toes ached after a while. Or… Oh! He was peeing again! Wonderful! And then the feeling was gone. He supposed that it was pretty bad when the most exciting thing you can possibly feel is when you wet yourself – and you’re looking forward to it! He wished he could feel it more often. Of course, if he did, then maybe his diapers would leak sooner. That would be a good thing. He knew that Mel would certainly like that. But he seriously doubted that his body was capable of peeing more often than he was now.
What was he supposed to do if she decided to raise the punishment level for not leaking on time? He was already doing everything possible. It was already killing him. He didn’t really want to contemplate such a thing. It would be bad! Very bad!

Mel watched him in his corner as she finished her lunch. He hadn’t moved a muscle – again – as far as she could see anyway. Amazing! Just what she wanted, but sometimes she wondered how he could do it.
She wondered what he thought about too as he stood there. With nothing else to look at but those two walls, thinking was about all he could really do. She’d probably never know what he thought about. Just like, hopefully, he would never know that she had once again faked putting the suppository up inside of him. As far as she could tell, it hadn’t made a bit of difference yet whether he knew or not. So far, the results had been the same. But would it continue to be the same? According to her plan, things were about to get more questionable as far as that went.
She finished her lunch and got up from the table. There were still things from the cabinets that needed to be put away, but not a lot of things. She wandered over and took a good look at what baby food he had picked out for himself. There were two jars of sweet-potatoes and squash – mixed together. Who came up with that combination? She picked up a brown jar. Beef! Yuck! Even in the jar it looked awful. She picked up a third jar. Strawberries. Well, that didn’t sound too bad. She wondered how it tasted. There was a second jar of strawberries as well and another jar of the brown beef mush. Six jars in all. While it sounded like a lot, she knew that for an adult it was really very little.
After glancing at him in his corner again, she began opening the jars and putting it all out on the plate for him. She got his bib out and took the tray off of his highchair. She was just about to call him to get his lunch when her phone rang. She hurried to answer it. “Hello?”
“Hi Mel.”
“Hi Sandy! What’s happening?”
“I just called to see if there has been any more fallout from what happened with his friend Robin yesterday.”
“Not yet. We won’t know till tomorrow.”
“Oh,” Sandy replied. “I don’t know if that’s good or bad.”
“Good – for now. We’ll take things as they come and deal with them.”
“That’s good. Say, are you two still going on that date tonight?”
“You bet! It should be lots of fun.”
“So what are you wearing?”
Mel laughed. “I bought three dresses yesterday. I still haven’t made up my mind as to which one to wear. Want to come over and help me pick one out?”
“You bet! I’ll be there in a few minutes!”
Mel hung up her phone and looked back at Sissy, still standing perfectly still in the corner. “Sissy… It’s lunch time. Get yourself into your highchair.”
Chad gratefully pulled himself off of his perch and out of the corner. He took a moment to flex his ankles so he could walk, then he headed for the kitchen where Mel was already waiting with the tray from his highchair in her hands. He got up into the chair and she fastened the tray in front of him, securing him into the chair. A bib followed. Then she brought over his plastic plate filled with all the mushy baby food and handed him a tiny baby spoon to eat it with. Finally, she pulled another baby bottle out of the refrigerator and set that on the tray too. Chad was already digging into the colorful mush in front of him and trying to eat it as best as he could. He had taken only two spoonfuls though when he heard someone at the door. He momentarily panicked before he remembered that Sandy was coming over.
A minute later, Mel ushered Sandy into the kitchen where he was eating. He saw her smile broadly at the sight of him. He kept on eating, shoving his little baby spoon into a pile of mush and carefully bringing it to his mouth. He was definitely getting much better at this. He didn’t think he had spilled any of it yet.
Without asking, Sandy walked over to him and pulled the spoon right out of his hand. She didn’t say anything to him as she walked over and set it in the sink. “He doesn’t really need that,” she said to Mel. “Babies like to use their hands more than the spoon. They like touching things.”
Mel just laughed. “Really? He’ll be such a mess!”
Sandy was grinning broadly as she mockingly shrugged her shoulders. “Aren’t they always a mess?”
Mel just shook her head and laughed again.
“Now where are those dresses?” Sandy asked, totally ignoring Chad who sat dumbfounded in his chair.
Mel and Sandy looked at all the dresses, including the blue one that Sissy was going to be wearing. It took a while, but they finally narrowed the selection down to one – that would go well with Mel’s wild new leopard print shoes. As Mel was putting the dresses back in her crowded closet, Sandy asked. “What about after your date, when you get home?”
“What do you mean?”
“I mean… You said these guys are both really good looking…”
Mel smiled. “Oh they are! Total hunks! Both of them!”
“So, I mean… it’s only natural that you’re going to want to… spend the night with one of them… or both if you like.”
Mel smiled and shook her head. “Not tonight. Besides, the guy who’s supposed to be my date tonight is really a two-timing son-of-a… you know what! And I’ve also got Sissy to worry about.”
“Sissy? Why? Just send him home… or… I can babysit if you like.”
Mel was a bit surprised. “Babysit? It’s probably going to be late when we get back.”
Sandy shrugged. “I don’t care. I can do it if you want. And what’s your big hang-up over this guy being a louse or not? I mean, you weren’t planning on marrying him, were you?”
Mel was shocked. “Heaven forbid! I was just so totally drunk when I suggested the date in the first place. If I wasn’t then this date wouldn’t be happening at all.”
“So still, what’s your problem? Get yourself a little fun. Let him tickle your bones.”
Mel shook her head. “Not tonight,” she sighed.
Sandy shook her head too. “Well, like I said, anytime you need me to babysit, just call.”
Mel smiled. “It won’t happen! But thanks for the offer anyway. I’ll let you know if I need you.” Mel did think of one other thing though, “Um… By the way… Would you like to come by later and help get him ready for tonight? You can do his makeup a whole lot better than I can, and I want him to look really good for tonight.”
“Well, I’d rather make him up to look like a baby… but I’d absolutely love to!”
As soon as Sandy left, Mel walked back into the kitchen and got a small shock. Sissy had baby food wiped all over everything! He was a total mess… as was his bib, highchair, and everything else within reach. “Did any of that food actually get into your mouth?” she asked.
Chad only shrugged. “Some!”
Mel shook her head. “Sandy may like you eating without the spoon, but I think we can do without this mess!”