Tuesday, March 29, 2011

The Bet - Chapter 35 (Friday – week 5 Part 7 of 8)

The Bet
by Karen Singer

Chapter 35 (Friday – week 5 Part 7 of 8)

Mel drove them to the same restaurant where they had eaten last week. As soon as she had parked her car, Mel once again told him to grab one of his empty baby bottles and carry it in with him – in his hand. Chad wasn’t at all happy to hear that. It was very embarrassing just to hold the thing let alone have to drink from it.
As they went inside, he was glad to see that there weren’t nearly as many people waiting as there had been last week. “Now don’t forget, Sissy,” Mel said as they walked through the door. “Just like last week. Curtsey, put your name on the list, and make sure you curtsey again when you’re done!”
Chad wasn’t thrilled to hear that. He had certainly made a fool of himself here last week. But then last week Mel had made him play a curtseying game with two little girls while they were waiting. A quick glance around at the waiting people turned up no kids at all… good! This would be bad enough! Feeling more than a bit apprehensive, he approached the waiting receptionist. He could see that she remembered him from last week. He wasn’t sure whether that was good or not. He grabbed both sides of his full skirt and pulled it wide as he dropped a curtsey to her. “How long is the wait?” he asked.
“Only a few minutes,” the receptionist replied with amusement in her eyes.
“Can you add us to your list?”
But before Chad had a chance to tell him his name, she asked, “Sissy, right?”
“Uh… Yes,” Chad replied, unhappy that she had remembered his name.
“Okay, I’ll call you as soon as your table is ready.”
“We’ll be right over there,” Chad pointed. Last week she had announced his name over their house system, even though she had been looking right at him.
“I know. I’ll let you know.”
“Uh… Thanks,” Chad replied. Then he dropped another curtsey, again spreading his skirt wider than he would have liked. He walked back to where Mel was sitting against the wall and stood near her.
“I don’t see your little playmates from last week,” Mel commented.
“No. They’re not here tonight.”
“Pity. They were delightful little girls.”
Chad didn’t exactly see it that way at all. The hostess called another party and the waiting room became a bit emptier. Right after that, Chad recognized the waitress that had served them last week coming up to the hostess’s counter. As she did so, she quickly glanced at the people still waiting to be seated. Her eyes fell on Chad and Mel and she smiled broadly. She glanced down at the waiting list then spoke to the hostess for a moment. The hostess nodded and made a notation on her list. She turned her microphone on. “Sissy, party of two.” Then she giggled. Chad wasn’t amused at all.
The waitress was still in the process of trying to grab two menus as Mel and Chad approached. “Can you change one of those menus for a child’s menu?” Mel asked.
The waitress looked back surprised, then stared at Sissy for a moment, then glanced down at the baby bottle in his hand. With a broad smile on her face she replied, “Of course.” She put one of the menu’s back and picked up a children’s menu instead.
“Do you have any crayons?” Mel asked.
Without answering, the waitress grabbed a box of crayons from a nearby container and held them up for Mel to see. “Please follow me,” she said as she turned and began leading them through the restaurant.
As they walked, Mel dug into her purse and extracted another twenty dollar bill. “Hand me your baby bottle,” she said to Sissy. As bad as it was to have to carry the thing, Chad wasn’t at all glad to get rid of it, because it meant that they he would soon have to be drinking out of it again – in the restaurant.
The waitress stopped in front of a booth and waited for them to be seated. Before Mel sat down, she handed the waitress the twenty dollar bill and the baby bottle. “And I’ll have coffee,” she said. The waitress left with a broad smile on her face.
Chad started to slide into the booth, but he quickly got back up again and grabbed his skirt to straighten it before sliding back in again. Sliding across the seat was a lot more difficult than just sitting down in a chair.
“It works better if you remember to straighten your skirt the first time you try to sit down.” Mel noted.
“Yeah, I know. Robin’s been on my case all day about it!”
The Robin woman again! Someday – soon – she was going to have to do something about her. But unfortunately, Mel realized that once again Robin was right. She had been ignoring too many of Chad’s male mannerisms. That couldn’t be allowed to go on much longer. Little things like just sitting down properly should have been addressed long ago. But that would have to happen later now, and certainly not here. It was time to delve into other things. She pointed at the children’s menu in front of him. “You might want to start getting busy with that.”
Feeling very foolish, Chad picked up the box of crayons and dumped them out on the table – four of them this time. At least he had one more color to work with than last night.
“So, who’s going to be at the poker game next week?” Mel asked.
Just being reminded of the poker game sent a cloud of worry across Chad’s face as he opened up the menu to find a decent picture to start coloring. “Besides you and me, just Derek, Ray, Steve, and George.”
“So there will be six of us? That’s a good number for poker.”
Chad shrugged. “Yeah.” He put the blue crayon to the page and began coloring in some sky.
Mel watched him for a few moments. “So what is it that you were so worried about earlier when we talked on the phone?”
Chad stopped coloring and looked straight at her. “What are you going to make me do?”
“You mean at the game?”
“Like what?”
“I mean, like… While everyone else is drinking from beer bottles, are you going to make me drink from a baby bottle?” Mel didn’t get a chance to reply before he kept going. “And how about what you’re going to make me wear? Is it going to be one of those silly sissy dresses? I can just see me now, showing up in that really babyish dress with my diaper showing. I don’t think the guys would really appreciate that!”
Mel almost laughed. “They might not, but I would! You must really like those dresses if you’re so worried about it.”
“No I don’t!”
“Which really means that you do!”
Chad blushed and looked down at the page he was coloring. “Maybe,” he replied embarrassedly.
“Which means yes. What else?”
“I’ll tell you something else I don’t think the guys will appreciate, especially George.”
“Me wearing only one diaper and then have it leaking all over his chairs.”
“Oh, I think we can find some way to deal with that too.”
It wasn’t exactly what Chad wanted to hear. “And how about my voice? This is… usually… a guys only thing. I don’t think they want to sit there all night listening to me talk like a silly idiot!”
Mel almost laughed out loud. “Oh I don’t know. I think they might get a big kick out of it.”
“No they won’t!” Chad replied sullenly as he went back to his coloring.
“But I would,” Mel replied. She watched him coloring for a few moments. “Anything else?”
Chad didn’t look up right away. “Lots of things! But I don’t want to mention them right now.” He thought of something else he did need to mention though and looked back up quickly. “Oh! And George wanted me to make sure you know how to play. He suggested I teach you a bit before the game if I have to.”
Mel looked at him and smirked. “Don’t worry. That’s not a problem. How do you think we spent all our time in the dorm rooms back in college when we weren’t studying?”
Chad just nodded and went back to his picture. Mel watched him for a few moments. “The truth is,” she said, “that I really had no idea what I’m going to do with you. I hadn’t even really considered it yet. But thanks for giving me so many good ideas!”
Chad stared at her – horrified! And then the waitress brought back his baby bottle.

Chad sat silently in Mel’s car on the way back to her apartment. He wasn’t sure if he should be glad or not that he was holding the children’s menu that he had colored. Why had Mel insisted he bring it home? She already had embarrassing pictures that he had done last night hung up on not only her refrigerator but also on his own living room wall. And all the pictures in this new book looked just as childishly colored as they had the previous night. It was impossible to color neatly while at the same time trying to constantly drink from a baby bottle. But then, he wasn’t sure if leaving the embarrassing book behind would have been any better. Would the waitress claim it as a prize of her own – and then show it off to everyone she could find? Ugh! Embarrassing! Even if he wasn’t there.
As soon as they had gotten back up to Mel’s apartment, she ordered him to prepare his punishment spot. “We might as well take care of that nasty demerit right now instead of later.”
As Mel walked off into her bedroom, Chad stood perfectly still for a few moments. He hadn’t exactly forgotten about the demerit, he had just been trying not to think about it. But trust Mel to not forget! He wasn’t looking forward to another beating, but there was no way around it… and he would probably be getting these beatings for a very long time to come since he had no intention of ever speaking in his sissy voice where anyone at work could hear him.
Almost lethargically, he grabbed a stack of disposable diapers and spread them out all over the floor where they would be needed. Then, because he knew what Mel would require of him, he began undressing, removing everything that covered him from the waist down except for his diapers. It was safer to leave those till Mel was ready.
Mel came out of her bedroom dressed casually in shorts and an old top just as he was finishing. She went straight to the corner where her yardstick was waiting and picked it up. Chad felt a twinge of fear running through his body the moment she grabbed it. Despite the number of times he had already been through this, the nervous fear continued to grow in him. Mel glanced around at the diapers that had been spread out on the floor. Good enough. “Okay, Sissy. Let’s get those diapers off of you.”
Chad stood still and let Mel rip open the tapes on each side of his diapers. She let go and they fell to the floor in a sodden heap. He suddenly felt even more exposed than ever. Slowly, as if trying to delay the inevitable, he moved into place and leaned over, putting his hands up against the back of the chair in front of him. He paused to brace himself, then forced his backside higher up into the air, making it a more inviting target for her wicked yardstick. All too soon he heard the quick swoosh of her stick as it sped through the air, but he didn’t have time to dwell on that sound as the sharp crack and pain of it hitting his backside interrupted all other thoughts. He wanted to grab his stinging backside, to rub the painful wound, but he forced himself to not touch it as he stood up. He dropped a curtsey to her. “Thank you, Mistwess,” he said in his silly sissy voice. Then he had to lean back over again, preparing himself for the next blow.
“I’m getting tired of punishing you for this,” Mel said just before she landed another stinging swat.
As Chad stood back up to curtsey and thank her, his main thought was that she couldn’t be nearly as tired of it as he was. But that didn’t mean that he was going to ever give in and let his coworkers hear him speaking like a fool. He just dared not tell her that.
As Mel watched him lean back again and prepare himself for the next blow, she said, “If we have to do this much longer, than I’m going to have to come up with an additional way to punish you!” Swish! Whap! She watched as he curtseyed and thanked her. He was starting to shake a bit now and tears were starting to form in his eyes. Good! “Speaking of additional punishments,” she said as he leaned back over again. “I hope I don’t have to give you five more swats again for not peeing during this!” Swish! Whap!
Chad was just registering her comment when the blow from her stick struck him. He realized that he hadn’t been trying to pee during the punishment yet. Another five blows would not be fun… he knew from previous experience! As he stood back up, he relaxed all his bladder muscles… sort of. Instead of holding back, he was now struggling to make himself pee. He curtseyed. “Thank you, Mistress.”
Another blow, another curtsey. Then another blow, then another curtsey. But this time, as he stooped down into his curtsey, the change in the muscle position at his crotch was enough to start him peeing. It was so sudden and without warning that it startled him. He was going to say something about it, but Mel beat him to it. “Just ignore it, Sissy, and keep doing what you’re supposed to. I see it. The fact that you’re peeing shouldn’t ever interrupt whatever it is that you’re doing. For you, it’s of no consequence at all.”
Still peeing, Chad did his best to ignore it and finished his curtsey. “Thank you, Mistress,” he finished. His peeing didn’t end till he was once again leaning over the back of the chair. Swish! Whap! At least he wouldn’t have to endure an additional five more blows.
When his punishment was over, Chad, openly crying again, curtseyed and thanked her for the last time. Mel set her stick back in the corner till next time, then while Chad was still blubbering pitifully, she searched the diapers that had been spread out on the floor for the one that looked the most wet. She had him lie down right where he was and diapered him with it. “Two hours now, Sissy. Don’t disappoint me or we’ll be doing this all over again in a little while.”
“No, Mistress,” Chad blubbered, promising himself that he would again do everything he could to get his diaper leaking before her deadline expired. He got to his feet and stared down at the diapers still strewn all over the floor. Thinking about what she had just said, he asked, “Do you want me to clean these up now?”
“Do you think you’re going to have a leaky diaper two hours from now?”
Chad had no way of knowing for sure, but he certainly intended on trying. “Definitely!” he replied confidently, hoping it would be the truth.
“Then go ahead and pick them up. But keep them handy just in case.”
Chad curtseyed and said, “Yes, Mistress,” but before he began picking up the diapers, he hurried to the kitchen and grabbed himself a baby bottle full of her awful green tea. He had a deadline to meet!

Friday, March 25, 2011

The Bet - Chapter 35 (Friday – week 5 Part 6 of 8)

The Bet
by Karen Singer

Chapter 35 (Friday – week 5 Part 6 of 8)

Chad hurried to get dressed again. He had showered after work as the best way to get himself cleaned up after removing his messy diapers. Now, dressed in two fresh diapers, his plastic panties, his waist cincher, the all-in-one girdle, and the same zebra print dress, he hurried to his closet to select a different pair of shoes. Since he would be having his toenails done too, he had left his pantyhose off this time. His skirt felt strange against his bare legs as he select a pair of open toed sandals that would later show off his freshly painted toes. As quickly as possible, he buckled the shoes onto his feet and checked his image in the mirror mounted to his closet door. His dress looked good – if not really nice. His makeup looked… okay. His hair looked… good enough. Acceptable… he hoped. With so little time to get ready, he couldn’t do anything more.
He hurried into his living room and opened the door to see if Mel was there yet. He saw her just driving into the parking lot then. He quickly grabbed his purse and diaper bag and ran out to meet her for their trip to the nail salon.
“Perfect timing,” Mel declared as he jumped into her car. A moment later, she was hurrying through traffic as fast as she could. “So, have you decided to keep the nail length you have now?” she asked as she drove.
Chad held up his hands and looked at his nails. It was a tough decision, but the more he thought about it, the more he thought he still liked the length his nails were now. “Yeah,” he decided. “I think I like them this way.” He could always get them cut shorter next week – and probably would.
“How about the color, have you thought about that?”
“Not really,” Chad replied. “Maybe I’ll just keep that the same too.”
“Pick something different!”
As they were walking up to the door, Mel stopped him for a moment. “I shouldn’t have to remind you about this, but I don’t want there to be any question about it when we get in there.” Chad had no idea what she could be talking about. “Remember how I had you greet everyone last week?”
Chad remembered it very well. She had made him curtsey to everyone.
“Well, this week,” Mel continued, “I better see you curtsey respectfully to everyone you talk to and I better hear nothing but your sissy voice when you speak... and I’ll probably ask your nail tech about that later if we aren’t close enough where I can hear you all the time.”
Chad hated having to act like a super sissy everywhere they went. Real women didn’t do things like that. It made him stand out all that much more! But at least she wasn’t making him go in there with a pacifier in his mouth this week. That would have been much worse. In fact, lately, she seemed to have forgotten about the thing. He dared not remind her about it though for fear of the consequences.
As usual, there were a few women sitting in the waiting area just inside the door who didn’t have appointments. Mel and Chad walked right past them and up to the counter where Mel’s usual nail tech was waiting for them. “Hello, Mel,” the woman said in her Asian accent.
“Hi,” Mel returned politely. Then she turned to Chad. “Aren’t you going to say hello too?”
Chad hated this. She hadn’t even been talking to him. But he dropped a polite curtsey and said hello in his sissy voice. The woman giggled. “You’ll have to wait a minute,” she told Chad, “your tech is still with customer.”
Chad started to tell her that it was just fine, but the scowl on Mel’s face stopped him. He curtseyed once again, then told her it was no problem. He would just wait.
While Mel walked into the back with her nail tech, Chad glanced around the waiting area. Everyone was looking at him curiously. He definitely felt like a fish out of water here. What should he do, just stand where he was? He noticed a few empty chairs together and decided to sit down. This time he remembered to grab his skirt before he sat. He heard someone across the room giggle slightly.
“That was a lovely curtsey,” one of the women closest to him commented.
Chad couldn’t ignore the smirk on her face. “Thank you,” he replied in his sissy voice.
“Lovely voice too,” she added after hearing his high pitched reply.
“Uh… Thanks.”
“Do you come here often?” the woman sitting next to the first one asked.
Chad hated being the center of attention like this. Or was it the center of ridicule? “Every week,” he replied. The women giggled together.
“So you’ve been here before?” the second woman asked, trying to prolong the conversation.
Dumb question! Didn’t he just say that? Instead of answering, he held up his hands so they could see his nails.
“Oooo. They’re lovely,” the first woman said, her gaze never leaving his hands. Then she leaned over so she could see them better and actually grabbed one of his hands so she could inspect his nails further. The second woman got up from her seat so she could see better too. “These are from last week?” the first woman asked as if she didn’t believe it.
Chad nodded. “Yes,” he replied.
“They’re lovely,” the first woman commented. Chad figured that lovely must be her favorite adjective.
“I like the shade,” the second woman added. “Maybe I’ll have mine done in that color too.” She looked up at Chad. “Are you keeping the same color?” she asked.
Chad shook his head. “No, I’ll probably be going for something different this week.”
The woman just nodded and sat back down. The first woman dropped his hand and sat back in her chair too. Chad was glad. He had been uncomfortable being under such close scrutiny, no matter how polite they had been. He noticed the other women in the waiting area turning their heads. He turned to see what they were looking at and was pleased to see his usual nail tech walking to the front with her previous customer right behind.
Chad waited where he was while the woman paid. Then before the woman could even get her wallet back into her purse, the nail tech looked straight at him and said. “Ready, Sissy?” Chad thought he heard someone sniggering nearby.
He quickly got up from his chair and would have followed his tech to the back, but she was just standing there like she was waiting for something. The woman who had just paid was watching closely as she closed her purse. Hating every second of it, Chad dropped another curtsey and said hello to his nail tech in his usual sissy voice. He heard the woman who was just leaving grunt with surprise, he dared not look at her. The nail tech just smiled broadly however and led the way toward the back.
As he walked toward the chair where she would be doing his toenails, he passed Mel having her own toenails done. The container of nail polish that was sitting out looked an awful lot like the color that would soon be removed from his own nails. Mel must have liked it.
As soon as he was seated and had his shoes off, the nail tech asked him about what color he wanted. “I don’t know,” he confessed. “Can you recommend anything?”
The nail tech opened a cabinet and stared at the bottles inside for a few moments, then she pulled out two of them. “I think either of these would be great for you,” she said as she showed him the bottles.
Chad was very surprised at what she had selected. They were both slightly different shades of purple! He would have selected a pink or a red… or at least something in those families. But purple? He was about to say no way, but suddenly she was talking again.
“I think the lavender would be the best,” she said as she set the bottles down and began grabbing what she would need to remove the polish that was on his toes now. “But the lilac is very pretty too. What do you think?”
Chad didn’t know which color was lilac and which one was lavender. He wasn’t even sure he could spell lilac. And as to them being pretty? “Uh… Yeah, they’re both pretty,” he agreed, he just had never thought about it before.
He was about to ask her to show him something else, like another pink, when she started telling him all about doing another woman’s hands with the lavender earlier that day and about how the woman had wanted her nails to match the color scheme for her wedding. Then Chad was forced to listen to all the wedding details that the woman had told the nail tech about. He wasn’t the least bit interested in wedding details, but obviously the nail tech was.
With the nail polish finally removed from his toes, the tech grabbed both the bottles of polish again. “So which one?” she asked, obviously delighted with both choices.
Chad still wanted to tell her he wanted to pick something different, but the delighted look on the tech’s face stopped him. Knowing he was going to probably regret it, he said, “I guess the lavender.”
“Yaaay!” the tech cheered quietly as she mimicked clapping her hands together. “I think is so pretty.” Chad wasn’t all that sure, especially when the lavender turned out to be the less subtle of the two colors.
Purple toes! And now he was watching her finishing his fingernails the same way. Purple! Something inside of him felt a bit squeamish at not only the thought of it, but now the sight of it. It wasn’t that the color was ugly – far from it. The nail tech had been right, it was sort of a pretty color, it’s just that… well… it was different! Okay, he had seen many of the young girls wearing much stranger colors than this, but… it wasn’t what he usually associated with a nail color he would wear! And now he was wearing it! Not only was he was wearing it… he was stuck with it for the next week! He wondered if Mel had silently pre-arranged this in advance. It would be just like her!
As soon as the tech was finished, Chad held his hands up and stared at his purple nails. The length was the same – she had only filed them down a bit to smooth out the edges – but now they looked so much different. And worse, he was sure that they would stand out so much more. The nail tech got up and headed toward the front, Chad got out of his seat too, but instead of moving, he glanced between the purple nails on his hands and the purple nails sticking out of his shoes. It was almost shocking! In a daze he followed her toward the front.
“Let me see,” Mel said excitedly as the tech was ringing up the sale. Chad noticed that Mel was now wearing the same nail color he had last week. He held his hands out to show her his fingernails. “Oooo… lavender.” Chad didn’t know how she had named exactly the right color. He wondered again if she had anything to do with it.
“I’m really surprised,” she said, sounding like she meant it. “What made you pick that color?”
Chad wasn’t really sure. “A wedding!” he finally replied.

Tuesday, March 22, 2011

The Bet - Chapter 35 (Friday – week 5 Part 5 of 8)

The Bet
by Karen Singer

Chapter 35 (Friday – week 5 Part 5 of 8)

Mel took a sip from the coffee that had just been delivered, then put her cup back down again. Gloria was still holding her cup, still drinking. Mel waited till she was finished. “I drink too much coffee,” Mel said, trying to get the conversation started.
“Me too,” but I have no intention of slowing down,” Gloria replied.
“Me either,” Mel agreed lightheartedly. She looked at her friend. “So, did you find out what you needed to know last night?”
Gloria smiled. “I really didn’t learn anything much that was new. One or two things only. But mostly, I feel fairly confident now that I got the real truth out of him.”
“So do you feel better?”
“Yes. But… He did say a few things that got me curious. Unfortunately, I didn’t have time to go into them with him.”
Mel nodded. “One thing always leads to another. It’s the same way in my profession.” Mel leaned forward. “Look, is there any way I can convince you to just keep asking how he’s doing every week? I’ve really got to know. I have nothing else to go on… no other way to tell if I’m doing something right, or if he’s gaining any ground back again.”
Gloria considered her request. Of course there was no way she was ever going to manipulate Chad again to do what Mel really wanted. But just getting the simple information Mel was requesting wasn’t really so bad. It wasn’t like she was doing anything to him at all. And it was all information that he readily knew – he’d only be sharing it. And then of course, there was the other thing… She nodded. “Yeah, for now I can do that. Besides, there are still some things I want to delve deeper into with him that he mentioned last night. So as long as I’ve got questions for him, I’ll ask your questions too.”
Mel sat back and picked up her coffee again. “That sounds perfect!” It wasn’t really. What she really wanted was for Gloria to hypnotize him again and make him totally incontinent in one fell swoop! She could do it – easily. But she was still refusing. But as with so many other cases in her life, compromise was better than nothing.

“I don’t see any problems,” Chad said as he continued to stare at the screen on his computer.
“I don’t either,” Robin agreed from her chair that she had pulled up right next to his. They had been quickly going back over their work together just to make sure they hadn’t missed anything.
“I say it’s ready, and that we tell Tom,” Chad said.
“I agree,” Robin replied as she pushed her chair backwards and got up.
“You want me to tell him?” Chad asked.
“You might as well. I really need to get busy on some of the other things I need to do. Just let me know if he has any questions.”
“No problem,” Chad agreed as he watched her pushing her chair back to her own cubicle. He picked up the phone on his desk and called his boss. “We’re done,” he said into the phone. “As far as we can tell, the whole thing is ready for the clients to just have.” He listened to his boss thanking him and agreed that both he and Robin would be ready to answer any questions about it on Monday. Then he hung up his phone again.
The project was finished. He always felt a huge feeling of accomplishment every time he finished something, and this was no exception. But now he had other things to get done, just as Robin did. But first… He listened hard, but he couldn’t hear anything from Robin’s cubicle next door. He didn’t think she would be coming back anytime soon so hopefully he wouldn’t be interrupted. He opened up the spreadsheet where he kept track of his progress on the bet. Things had been going badly all week, and yesterday had been more of the same.
He quickly found yesterday’s date and went to the column next to it. He filled in 18 minutes and stared at the results. Another minute lost! How? He was still going backwards. He looked at the column that listed days still to go – twenty eight. Four more weeks! A long time… but not nearly as long as it used to be. He had to start getting his control back again. And so far, today hadn’t been going much better than yesterday. But then, it was still early in the afternoon, things didn’t usually get any better till much later in the day when he had less fluid in his system to get rid of.
He quickly closed the spreadsheet again, telling himself that he didn’t want anyone else to see it. But the truth was, that he didn’t want to look at the results himself.

George hung up his phone and sat back in his chair. He had finally gotten in touch with Derek who had been out of the office earlier. Each of the guys had agreed to let Chad and his girlfriend… girlfriend?... into the game, but each had their own reasons. Steve had said the more people there, the more money he could win. Ray had agreed because he wanted to see Chad’s girlfriend… but then George had the sneaking suspicion that if Chad’s girlfriend looked even halfway decent then Ray would be trying to get her into bed with him. Ray had something of a “reputation.” A big one!
And now Derek had agreed too. But Derek and Chad had always been fairly close. Long time buddies. Derek had agreed only because Chad was his friend.
That left it all up to him. And the truth was, that he didn’t really want Chad there. His girlfriend either. This was supposed to be a night for just the guys. A night to just hang out with some male friends and enjoy themselves. He really wanted to tell Chad no! But if the other guys said Chad should come, then who was he to go against everybody’s wishes. He just hoped that Chad really would contribute at least some of the beer. It also wouldn’t be too bad if his girlfriend really was good looking too. But how good looking could she be if she was going out with someone like Chad? Which didn’t sound likely to him, but, well, that was all Chad’s problem.
He picked up the phone and dialed the number for Chad’s desk.
Chad listened to his phone ringing several times before he picked it up. He was afraid the call would be another woman with another stupid guess as to what was on his nonexistent t-shirt. He was surprised to hear George on the other end of the line. “Hey, George. What’s happening?” He just knew that George would turn him down. He could practically feel the tutu that Mel would put on him encircling his waist as he walked into work.
“Okay,” George said. “I got the guys to agree for you. But you better come through with some of the beer in return!”
Chad felt elated. “No problem! Believe me! I really appreciate this!”
“Yeah, well, I just hope your girlfriend knows how to play. Does she?”
That stopped Chad. “I really don’t know.”
“Then teach her if you have to… before the game!”
Chad laughed, but it was a laugh of relief. “You got it!”
He dared not phone Mel because he would have to use his sissy voice when talking to her and someone might hear him. Besides, she was usually busy with clients or in court and would have to return his call later. So he opened up his email program and sent her an email telling her that everyone had agreed to let them play. The minute the email was sent, he felt really good… but that didn’t last very long. Images of what she might make him do in front of the guys began running through his head once more.
He knew he was supposed to be working on other things, but worrying about the poker game now was crowding out all other thoughts. He sat back in his chair and turned away from his computer. His gaze fell on what was left of the bouquet of flowers Mel had sent him last week. The flowers looked terrible – all of them. Had it really been a week already since his divorce had been declared final? How fast time could fly!
He thought back to some of the things he had been forced to endure in the past week, not the least of which was the humiliating day he had been put through last Monday. Had he really been to the mall dressed like a sissy idiot and sang “Mary Had a Little Lamb” in the concourse? It was a disturbing thought. And now he had something else to worry about, the poker game. What humiliating things would Mel make him do there? And in front of all the guys he knew. Word would get spread around the company like wildfire the day after. Was his life going to get suddenly worse? Probably! In fact, more than probably! The only question now was, in what ways?
Feeling more frustrated than ever, Chad got up and pulled all the remaining flowers out of the vase and threw them into his trash can. The vase, he stuck into his desk drawer behind his purse where he wouldn’t have to look at it.
Mel was just itching to expose him at work for the big sissy that he was. Would she really make him wear one of his sissy dresses to the game? He could only pray that she wouldn’t!
His cell phone rang a few moments later. Since he now kept it on top of his desk he was able to pick it up much faster. He saw that the call was from Mel and once again hurried out into the hallway before he answered it. He was still hurrying as he opened his phone and said, “Hello, Mistress,” in his sissy voice.
Mel took a moment to reply. “Sissy! You’re hurrying somewhere again – trying to hide!
Chad knew there was no denying it. “But I can’t let anyone hear me talking this way!”
“I told you before that’s not supposed to be a problem. I don’t care if they hear you! That’s another demerit!”
Ugh! Another beating. It was the last thing he really wanted… well, maybe not the last thing. He didn’t want to go to the poker game now either. “Yes, Mistress,” he replied, reluctantly.
“Now… I’m very glad that everyone agreed to let us into that game. Although I should mention that I was very much looking forward to shopping for a ballet outfit for you this weekend. I’m still thinking about it.”
“Mistress, please! Please don’t send me to work that way! I’ll die!”
“No you won’t! And don’t worry, I haven’t decided to do it… yet! Especially since you did manage to convince everyone to let us play.”
Chad felt relieved – very relieved. But not totally. “But Mistress, what are you going to do to me at the game?”
Mel was slightly amused at his question. The truth was, she had no idea. She still didn’t have a clue as to why she had even insisted that he get them into the game. “We’ll talk about that tonight at dinner. I just wanted to thank you for convincing everyone to let us play.”
“You’re welcome,” Chad replied sullenly. He would be finding out more tonight at dinner. He wasn’t really looking forward to hearing the details. He had no doubt they would be pretty much terrible!

At break time, Chad again followed Robin in the line to get coffee. He briefly looked around the room expecting to see Derek, but there was no sign of his friend. Although he wasn’t sure what would be worse, feeling uncomfortable sitting with Derek, or feeling uncomfortable from whatever comments the women would throw at him. With Derek missing, he had no choice at all.
As they headed toward the table, Robin slowed momentarily to speak to him. “Now don’t forget to remember what everyone is wearing this time. And for heaven’s sake, fix your skirt before you sit down!”
Chad was tempted to say a sarcastic ‘Yes, Mistress,’ but he forced himself to say nothing.
There was already a conversation underway at the table as they dragged their chairs over and sat down – Chad carefully arranging his skirt beforehand and attempted to sit slowly and gracefully. He looked over to Robin afterwards for her approval, but all he saw was her rolling her eyes before looking back at the other women.
For once, the conversation didn’t center around him and Chad felt glad. He sipped at his coffee as he listened halfheartedly about the problems some of them were having with their kids. As he sat there, half listening, he tried to carefully take note of what some of the women were wearing. Naturally, it was the sexier and more flamboyantly dressed women that caught his eye. The others he barely noticed. One woman in particular looked good in her low-cut knit top. He couldn’t tell what she was wearing below the waist because the table was in the way. She had on a beautiful necklace and several bracelets too. And her earrings were huge. Since her hair was pulled back and tied with a pretty feminine bow behind her head, he noticed how they bumped against her neck as she moved her head or spoke. The earrings were almost mesmerizing. What was it like to wear earrings like that? Were they uncomfortable? Were they a nuisance? Or were they just plain fun?
“What are you staring at,” the woman asked him.
It was a moment before Chad realized that she was talking to him. He jumped back to reality. “I’m sorry? What?”
“I was wondering what you’re looking at.”
Chad was a bit embarrassed. This was why he didn’t look too closely at women. “Your earrings,” he replied, slightly embarrassed about it. “I love them.”
She reached up with a smile on her face and touched one. “Aren’t they great? I’m glad someone else noticed them too. I just got them.”
“So Sissy,” another woman asked. “Are you finally considering getting some earrings of your own?”
Chad wasn’t really sure what would be happening. He only had another month left before the bet was over with. “Um… I’m still not sure.” He replied. “I’m thinking about it.”
“Well, think harder! I’ve been telling you for weeks to get your ears pierced. You keep buying lots of pretty new clothes, but nothing else to go with them. Your necklace and ring are very pretty, girl, but it would be nice to see something different on you for a change.”
Chad heard mumbling of general agreement among the women and suddenly felt very self conscious. He actually felt embarrassed because he always wore the same necklace, ring, and watch… and he wasn’t wearing earrings. He had thought his jewelry was great. Besides, it was Mel who dictated everything that he bought. “Uh… I’ll consider it again,” he finally replied, unsure what else he could say.
“You do that!” the woman replied.
Chad was glad that the conversation turned once again away from him and back to their kids and family. He wasn’t sure what was worse, them throwing silly guesses at him about what was on his nonexistent t-shirt, or being criticized for what he was… or wasn’t wearing. This time, he was consciously careful about not staring too long or too intently at any one woman. The result being, that he took in very little about the details of any of their outfits.
A little while later as he and Robin were walking back to their desks, she asked him. “So, did you remember what everyone was wearing?”
“A few,” Chad admitted.
“So tell me.”
“Well… The one with the big earrings that I liked, she had on a great knit top…”
“What color was it?”
“What color? Kind of a blue, I guess.”
“You guess?”
“Yeah. It was blue. Or maybe some kind of green.”
“It was teal you dummy!” She threw her hands up in the air. “Hopeless!”

Friday, March 18, 2011

The Bet - Chapter 35 (Friday – week 5 Part 4 of 8)

The Bet
by Karen Singer

Chapter 35 (Friday – week 5 Part 4 of 8)

Chad was miserable. More than miserable. He didn’t want to play poker with the guys – at least not till after he won the bet. As he walked back toward his desk, he kept trying to imagine what she would do to him there. He could just see himself showing up at the game in one of his sissy dresses… maybe even the one that was so babyish and didn’t even begin to hide his diapers. For that matter, would Mel make him wear only one diaper there, with instructions to make it leak before the night was over? Talk about embarrassing! And then there was his stupid sissy voice that she was so instant that he use all the time… as if he could! He could just see the guys all laughing at him over that! Or maybe she’d dress him up like a slut and somehow talk them into playing strip poker… with instructions for him to lose – and eventually he’d be down to just his diapers. What then? Embarrassing! And while his friends all drank from beer bottles, would he be drinking from baby bottles? Damn!
Maybe it would be better to just tell her that George had said no. But the minute he thought that, he pictured himself being abandoned at work wearing nothing but a pink ballet costume. Nowhere to run. Nowhere to hide. As humiliating as the thought was, and it did kind of turn him on, he knew he could never manage coming to work that way. He would have to find some way to convince George to let them both in the game.
Still picturing himself in a pink ballet outfit, he opened up the company phone book and found George’s number. He sat down hard in his chair, then quickly got back up again and almost angrily pulled his skirt out from under him before he sat back down again. Damn! The things women had to put up with! A minute later, he was listening to George’s phone ringing. Maybe George wouldn’t be there. Maybe George was home today. Maybe he’d have a good excuse for not getting into the game that Mel would approve of. And maybe he’d be wearing a tutu to work next Wednesday! It was almost with relief that he heard George’s voice finally answering.
“Hey George. This is… Chad.”
“Hey Chad. What’s up?”
“Uh, you know that poker game you’re holding next week… Are you still having it?”
“Of course. Why?”
“Um… I know this sounds strange, but… I really need to be there… Me and a lady friend of mine!”
Chad could just picture how annoyed and angry George probably was. “Please, George. Please. It’s important.”
“Important? Why?”
“Trust me, it just is. To me anyway.”
George paused for a moment. “I don’t know Chad. I mean, the games are just for the guys, you know? Heck, you’ve been to some of them yourself! And you don’t exactly qualify as a guy anymore.”
Chad knew it was true. He knew it, but it still hurt to hear. “I know, I know! But please, I’ve got to be there.”
“Chad… or is it Sissy… you’re not a guy anymore. You can’t come!”
“We’ll bring the beer!” Chad replied quickly, trying to force the issue.
George paused again. “I thought you didn’t drink beer.”
“I don’t. Not usually anyway. I’ll bring my usual soft drinks too.” Inwardly though, Chad was wondering if he would be bringing baby bottles instead. He heard George pausing again. “Please, George,” he pleaded almost pathetically. “I really want to be there.”
“Who’s this lady friend you want to bring?”
There was no way Chad could tell him that Mel was his Mistress. Although he had no doubt that if they did get into the game that George would find that out fairly quickly. “Uh… she’s just a friend. A good friend.”
“Uh huh. I see.” George wasn’t at all sure what it was that he saw though.
“Please,” Chad pleaded again.
George sighed. “Look, Sissy… or Chad… whatever! I don’t think it’s going to happen, but I’ll ask the other guys and see what they say. Okay? That’s about the best I can do.”
Progress! At least he wasn’t totally saying no anymore. “Thanks George... Hey! Who’s playing?”
“Just Derek, Ray, and Steve… and me of course.”
Chad did some quick thinking. Maybe he could appeal directly to the other guys. “Why don’t I ask them about it, personally?”
“No way!”
“But, I mean, it is my problem. I could handle asking them so you wouldn’t have to bother. I’d be glad to do it.”
“Not just no… but hell no! I’ll ask them myself! I don’t want to hear about you whining about your little problem from them… whatever your little problem really is.”
“Thanks George. I owe you. Please try to convince them.”
“I’ll ask, but I’m not so convinced myself.”
“Thanks, George. I appreciate it.” Chad was about to hang up when he heard George’s voice again.
“Hey Chad!”
“This lady friend of yours. Is she good looking?”

Robin stared at the top of her cubicle wall, not sure she believed what she had just heard. It wasn’t that she had been really trying to listen, but he had gotten louder and louder the longer he had talked. Mostly anyway. Before she knew it, she was on her feet, heading for his desk. “Hey Sissy,” she said as she entered his cubicle.
Chad turned around, knowing instantly that Robin had heard his phone conversation.
“Did I hear you asking to get into George’s poker game?”
“Yeah,” Chad admitted sheepishly.
Chad searched for an answer. He couldn’t tell her what Mel had threatened him with, but that did lead him to another answer. “Because I made the mistake of mentioning the game to Mel, and now she wants to be there.”
Robin tried to digest that for a moment. “Wow, you must really like her then.”
Chad just shrugged, but offered no answer to her question.
“So is George letting you in… even though I thought it was a ‘guys only’ thing?”
“I don’t know yet.” He sighed. “Right now, it doesn’t sound like it.”
“So what’s Mel going to say if George says no?”
“Knowing Mel, she’s not going to be happy at all!”

Chad was a bit hesitant as he approached the door to the gym. He just knew that the receptionist would try to make him do something humiliating again – no matter that whatever she asked him to do was usually mild compared to other things he had done elsewhere. And if he didn’t do whatever she asked, then Cassie would find out… and if Cassie found out, then Mel would soon know it. There was just no winning. Reluctantly, he opened the door and went in.
“Hi Sissy,” the receptionist called brightly.
“Hi,” Chad returned, reluctantly. “Will you please…”
“Oh come on! Can’t you greet me nicely? You know how I mean.”
Here we go, Chad thought. Reluctantly, he dropped a curtsey to her and using his sissy voice, again said hello.
She giggled. “That’s much better. Thank you.”
“Now can you…”
“Hey,” she interrupted him before he could finish asking her to get Cassie. She leaned as far across the counter as she could toward him. “Are you wearing diapers again?”
“Yeah. That’s kind of why I’m here.”
She giggled again. “What do they feel like?”
Chad was shocked. “What do they… They feel bulky and wet!”
She giggled once more. “Real wet?”
“Yes real wet!”
“And you said bulky?”
“Yeah, very!”
“Because you wet them so much?”
Chad was getting fairly exasperated. Where was this going? “Yes!”
“So you really wet them a lot this morning?”
“Just like I always do!” Chad was beginning to get a bit more angry now.
She tried to lean further across the counter. “Can I feel them?”
Chad was shocked once again. “Can you… No! Besides they’re all covered up under my other clothes. You know that. I can’t even get to them without a lot of trouble.”
“No,” she replied quickly. “I mean, can I just feel around your bottom? From the outside?”
She wasn’t giving up, and Chad knew that if he didn’t let her then she’d tell Cassie.
“Okay,” he finally agreed… If… you get Cassie for me afterwards.”
“Of course,” she giggled as she hurried out from behind the counter.
Before he knew it, she was pulling up his skirt all around. “Hey!”
“Shhh! I’ve got to get close enough to feel, don’t I?”
Chad wanted to tell her that she didn’t have to get close at all, but he held his tongue and let her have her way. She held his skirt high up out of the way with one hand while she felt all around him with her other hand, at times, pressing firmly to see just how bloated his diapers were. She even tried to feel him directly under his crotch.
“Geez,” she said. “I can tell you’ve probably got diapers on under there, but everything is packed so solidly on top, that I can’t really feel much at all.”
“That’s kind of the point,” Chad replied.
“Oh pooh!” she said as she dropped his skirt. Then she giggled. “Still, it was fun.”
“Are you going to get Cassie now?” he asked.
She smiled. “Of course!”
Chad was very glad to see her go. He smoothed his skirt back all around the minute she was out of sight. Women!
As soon as Cassie got there, Chad quickly dropped another curtsey and greeted her. He was anxious to get on with his changing and away from the receptionist. “Hi Sissy,” Cassie replied, sounding almost bored. “Are you ready? Let’s get this over with.”
Chad followed her back to their usual small office and began undressing while she started pulling diapers, suppositories, wipes, and a baby bottle out of his diaper bag. As usual, it took a few minutes for him to get out of his dress, shoes, pantyhose, all-in-one girdle, and finally the plastic panties – till all he had on was his waist cincher, glued on breast forms, and his diapers. It was a lot of trouble to go through every time he needed to be changed, but then that’s the way that Mel wanted it.
He laid down on the floor and Cassie gave him the bottle, which he stuck directly into his mouth and started sucking on the nipple. The liquid felt good against the back of his dry throat. He didn’t have to look to see what Cassie was doing, feeling was just as good. Within moments, he felt her pulling open the tapes that held his diapers tight against him. Then he felt the front of his bulky, soggy diapers being pulled down through his crotch, exposing his damp bare skin to the open air… well, almost bare skin, his chastity devise did cover some of it.
He felt the cold shock of the baby wipe as she wiped off everything on his front that she could reach. Unfortunately, she couldn’t touch the one main thing there that he would like touched, the part of him trapped inside the chastity device – the part he tried not to even think about anymore - the part that had wanted so much to give him relief from his sexual frustrations, but was denied any ability to do so – the part that Mel had rendered – useless!
“Lift up a bit,” Cassie requested.
Chad lifted his bottom off of the floor and felt her pulling the soggy diapers out from under him. Quickly, he felt her shoving two new ones back in their place.
“Okay, Sissy. Roll over.”
Chad set his bottle down and turned over onto his stomach, his freshly wiped front side now resting on the fresh diapers under him. He remembered when Cassie had spent more time on his front side, trying to get a response out of his trapped penis. How long had it been now since she had done that? He couldn’t really remember, but he didn’t think it had been all that long. Of course, he hadn’t had any kind of response to her touch in quite a while now. For that matter, he didn’t remember that part of him responding to anything anymore. Somehow that seemed a bit humiliating to him and something touched and stimulated his deeply rooted sexual need that resided in his whole body now. But that stimulation did nothing to the one organ that it used to affect.
The feel of the baby wipe wiping his backside felt better than it did on his front. There was more open flesh there to appreciate being cleaned. Despite the cool wipe being rubbed all over his exposed flesh, he felt the shock of the colder baby lotion as she began wiping it thickly all over him back there. He closed his eyes at the pleasure. The cold lotion quickly warmed to his skin temperature as her hands slid smoothly over his bottom. All of his bottom. Then closer to his asshole. Closer still. Till suddenly he felt her finger there… then it was gone.
He couldn’t see what she was doing, but he hoped he knew. It took a few moments.
“Scootch your knees up now,” she requested.
Yes! This was the part that he was waiting for almost as much… no… maybe more than the joy of clean diapers. He felt the point of something hard touch his asshole. It wasn’t shock that ran though his body the moment it touched him, but it was a closely related feeling. He wanted that device of hers… he wanted it up inside of him. Without realizing it, he opened his bottom up wide, trying to do everything he could to accept the toy she was using on him.
He felt her pushing it slowly inside… oh, the feeling! He felt each of the tiny little ribs on it going into him – each one adding a slight bit of extra pressure as it passed through the opening in his bottom. He was tempted to just thrust himself against it, but he held himself firm, letting himself enjoy the slow buildup of pleasure this time. Then she was pulling it out, just as slowly. He felt the little ribs of the device going out now, feeling just as good as they did going in. Without pausing, she was pushing it back into him now, pushing harder, faster. Then out again, just as hard. Then in… then out… He couldn’t stop himself if he tried. His body was suddenly doing the thrusting – in and out. Back and forth! Over and over. Trying – vainly – to reach that unreachable pinnacle of sexual release.
It seemed to go on forever, yet as good as it felt, he couldn’t get there – couldn’t achieve what his body longed for so badly. Sadly frustrated, he slowed his actions, slower and slower… then stopped. As hard as he tried, it was useless. He just couldn’t do it. He felt her pulling her toy out of him then, his asshole feeling strangely empty. As his body got used to being empty again, he suddenly felt her finger intruding its way inside of him once more. He grunted in distaste. She was shoving another of the damn suppositories up inside of him again. The stupid little pills that robbed him of having any chance to control the mess that came out of his backside. He wished – as he did every day – that just once she would forget to do it.
“Okay, roll over again.”
Chad rolled over onto his back again and once more grabbed his baby bottle, putting it right back to his lips. He felt her hands between his legs as she grabbed the first of the two diapers under him and pulled it tightly up and over him, adjusting it to where it needed to be. He felt the pressure as she firmly taped the right side of the inner diaper into place then the added pressure all across the front as she closed the other side and pressed that tape closed as well. Her hand dipped back between his legs again and pulled up the outer diaper, adding much more bulk between his legs and around his hips… but at the same time, adding that much more security. The taping was repeated with the second diaper, and suddenly he was done.
“Okay, Sissy. That’s it,” she said. “Nice and easy. You finish your bottle and I’ll be back to check on you in a little while.”
It was nearly the same every day. He laid right where he was and finished his baby bottle. When he felt the urge to pee before it was done, he held it for as long as he could while he kept drinking. But something about adding additional liquids to his system while he had to pee so badly didn’t work and he quickly lost the battle, wetting his freshly replaced diapers. Oh well, he liked them wet anyway. They felt better that way.

Tuesday, March 15, 2011

The Bet - Chapter 35 (Friday – week 5 Part 3 of 8)

The Bet
by Karen Singer

Chapter 35 (Friday – week 5 Part 3 of 8)

“Break time, Sissy,” Robin called from his cubicle entrance.
Chad turned around. “Already?” He leaned back in his chair. “I’m ready though. I need a break from this.”
“I know what you mean! But we’re almost finished.”
“Yeah, we should be able to tell Tom it’s done by lunchtime – I think.”
“I hope so. I’m ready to move onto something else for a while. This was a big one.”
“You can say that again,” Chad agreed as he closed the programs on his computer and got to his feet. As he followed Robin out into the hallway, he was more conscious than ever of the skirt he was wearing, probably because it was so full and he kept brushing his hands against the loose material. His legs also felt like they had a lot more freedom underneath.
“Okay, Sissy,” Robin said as they approached the break room, “this time, try to remember what everyone is wearing… Or at least some of them.”
“Sounds like a lot of trouble to me.”
“Just do it!”
As usual, Chad followed Robin in line for the coffee. They were both disappointed to see that there were no doughnuts though. “Oh well,” Robin said. “I wouldn’t want to undo everything I worked so hard for at the gym.”
No magical space opened up at the table for them as they approached it today, but they still had no trouble pulling up seats around it. Chad sat down, then had to stand up again to straighten his skirt before he sat down again.
“Hey Sissy, that’s another new outfit!” One of the women noted as he did it. “I like it.”
“Thanks,” Chad replied. “I kind of like it too.”
“Well, I guess you should, you bought it!” another woman added with a slight laugh. A few of the other women laughed with her.
“Your closet must be getting almost as full as mine is by now,” one of the women noted.
Chad just shrugged. “There’s still a bit of room left in it.” He didn’t tell them that the main reason there was still room in his closet was because Mel had carted all his male belongings off – to somewhere.
“Yeah?” another woman replied. “But at the rate you’re buying new stuff, it should be full pretty soon! I aught to know, my closet is stuffed to overflowing and so is the one in my guest room! Of course half the things I have don’t fit anymore. I only keep them because I figure I’ll be able to get back into them again… someday.
There was some general laughter from around the table.
“Shoot! I don’t throw anything away!” another woman added. “I’ve got stuff in my closet from back in high-school!” There was more laughter.
“Me too!” another woman added. “I just can’t seem to part with any of it!”
As the laughter from around the table continued, Chad would have thought they were pretty much joking, but he had been married! His wife – make that ex-wife – had been pretty much the same way – a ton of clothes she never wore and that he was sure she would never wear again.
“Hey Sissy!” one of the women suddenly added. “I’ve got another one for you.” Chad briefly wondered another what. “How about… Totally sissified man!”
Chad was shocked as the laughter rang around the table.
“Are you kidding?” another woman laughed. “He’s not a man. Look at him!”
To Chad’s embarrassment, there was another huge round of laughter.
“He’s not a woman either though!” someone else called out, Chad didn’t even see who. The women all seemed to be getting worked up into a laughing frenzy.
“Well then, how about… Totally sissified sissy!” Someone offered, modifying the suggestion that had been made a few moments ago.
Chad’s face burned red with embarrassment. Their comments were beginning to hurt, even though they were all true – more than they even knew! He had thought that these women were friends. Obviously he was wrong. He was seriously contemplating getting up and leaving when one of the laughing women suddenly leaned over and put her arm around him. She hugged him slightly as she laughed and said, “Don’t worry, we all still love you.”
Chad wasn’t totally sure, but he finally realized that they were all just having fun. And of course he would be the brunt of their teasing. What else could he expect? He was a sissy after all! And didn’t he inwardly love the humiliation? He just wasn’t totally sure about that just then.
On the way back to their desks, Robin asked him, “Well, did you notice what they all were wearing?”
“I tried,” Chad said, “but mostly I didn’t think about it. I was too busy being embarrassed by the things they kept saying.”
“They did come up with some funny slogans for your shirt,” Robin chuckled.
This time Chad chuckled a bit too. “Yeah, they did.”
“Maybe you should have another shirt made with one of their suggestions.”
“Uh… I’ll pass on that for now!” Robin laughed as he turned into his cubicle and sat down. Then he had to stand up again to straighten his skirt before he sat down again.
“You’ve got to stop that!” Robin complained.
“Not fixing your skirt before you sit down.”
“Well… I don’t think of it.”
Robin rolled her eyes. “Stand up again!”
“Just do it!”
Chad groaned a bit, but he got to his feet.
“Now sit down.”
“You just…”
Chad sat quickly.
“No, you idiot! Fix your skirt first! Now do it again.”
“Just do it!”
Chad stood up feeling annoyed.
“Grab your skirt and pull it out.”
“Ugh!” But he did as he was told.
“Now sit down!”
Chad sat. “Okay?” he asked sarcastically.
“Now do it again.”
“Do it again! You’re not going to learn to do it right unless you get used to it!”
Chad groaned again, but he once again got up. This time he was more flamboyant in the way he grabbed his skirt, as if he was mocking Robin’s guidance.
“This time,” Robin said, “sit more gracefully.”
Chad wanted to say something, but he bit his tongue. “He sat down slowly, again as if he was mocking her suggestions.”
“Better!” was all that Robin replied. “Try it again.”
Chad almost shouted his complaint, but he stopped himself and just stood up. This time, he quickly grabbed his skirt, but he sat down slowly again.
Robin shook her head. “It’s actually better, but you’re making a game out of it. This stuff has to be natural to you. Completely second nature. You shouldn’t even have to think about it.”
“Well, you’ve been doing it a lot longer than I have,” Chad returned.
“All the more reason why you need to be practicing it now! So do it again.”
Chad looked at her like she was crazy.
“Do… it… again!”
Women! Why couldn’t they just leave him alone! But he knew that Robin would only hound him if he didn’t make the effort. With another groan, he got to his feet. He paused, then grabbed his skirt, then sat down – trying to be at least somewhat graceful. But Robin’s only comment was, “Again!” Four more times she made him do it. Then she finally left with one parting comment. “Now keep doing it that way.”
It was childish, but Chad actually stuck his tongue out at her as soon as she was gone.

Mel reread the paragraph for the third time. It was simple basic stuff, but it still had to be checked. Unfortunately, her mind kept wandering, so consequently, she didn’t remember anything about what she had been reading. The problem, of course, was Chad – Sissy. She didn’t want him to go to the poker game, but something deep inside of her was still telling her to do it. Why? It made no sense! It was all wrong!
She thought again about what Andrea had said, if she couldn’t get it out of her head, then maybe she should send him. Maybe her subconscious was trying to tell her something. Maybe something important. And she’d never know what it was if she didn’t send him.
With a sigh of frustration, she reached for her phone.

Chad heard his cell phone ringing inside his purse – inside his desk drawer. As quickly as he could he opened the drawer and pulled his phone out of his purse. Shit! It was Mel. Quickly getting to his feet, he hurried up the hall, even as he opened the phone and answered the call. “Hello,” he said, careful to use his high-pitched voice.
“Sissy!” Mel’s angry voice replied. “What took you so long again?”
“I can’t get my phone out of my purse that fast. I keep it closed up in my desk drawer.”
“Then keep your phone out of your drawer, on top your desk! And you sound like you’re hurrying somewhere again!”
Chad stopped where he was, hoping nobody could hear him as he spoke. “How did you know?” he asked.
“Your breathing is practically panting and I can hear your heels on the floor!”
“Oh.” He hadn’t thought about the sound his heels might be making.
“You’re still trying to hide again!” Mel proclaimed.
“But I can’t let anyone hear me talking like this!” Chad whined in his sissy voice.
“I don’t care! You can! And you will! Next time, it’s another demerit!”
But all Chad could think about was that he couldn’t. There was absolutely no way!
“Sissy!” Mel’s voice brought him back to reality. “I need you to do something – something you’re probably going to love.”
Love? “What is it, Mistress?”
“Remember that poker game you told me about that your friend is throwing? I want you to get in it.” The minute Mel made the request, she realized she was leaving out something important. “Not just you, but me too!”
Chad was shocked. Something he’d love? Maybe under different circumstances! “But Mistress…” He searched for a way out. “That’s kind of a ‘guys only’ thing. No women.”
“I know, and I don’t care! Just do whatever you have to, to get us in that game! Tell them we’ll even bring some beer – lots of beer!”
Why was she being so insistent? She had to have some kind of humiliating motive behind it – strip poker maybe? But the guys would never go for it… well, if she was there, maybe they would. She did have a gorgeous body. Maybe he hadn’t seen it with his eyes, but he had certainly felt every inch of it. He didn’t even want to imagine himself at the game, talking in his silly voice… and what would she make him wear, one of his sissy dresses? No way! “But Mistress, they’ll never go for it!”
“See to it that they do. Cause if you don’t…” Mel tried to quickly think of some appropriate punishment. An odd picture came to her mind. “If you don’t, then the day after, I’ll be driving you to work personally and leaving you there so that you’ll have no way home. But instead of leaving you there in one of your pretty sissy dresses, you’ll be spending the day in a pink ballet outfit complete with tutu! Now wouldn’t your friend Robin just love to see that?”
Chad was horrified. “You wouldn’t! You couldn’t!”
“Yes I would!” Mel returned. “I told you before how many times I was sorry for not taking you to work in your sissy dress the last time!”
She had told him. More than once! She was just looking for another excuse to really do it. “I… I… I’ll try,” he stammered into his phone.
“Don’t just try… do it! I’ll expect to hear from you later that you’ve succeeded, or after you get your nails done tonight, you’ll be trying on ballet slippers!” Mel hung up her phone and smiled. She hoped she had sounded sufficiently mean. She thought she did. At least she had convinced him to try to get them into the game. She wasn’t really sure if he could manage it or not, but she had to properly motivate him to try hard enough. And if she didn’t… we’ll she wouldn’t really do it, but the thought of him in a pink leotard with white tights, pink ballet slippers, and a white tutu – at work, was enough to make her feel very amused. And strangely, the more she thought about it, the more she realized that the idea was making her wet in a very pleasant place.

Friday, March 11, 2011

The Bet - Chapter 35 (Friday – week 5 Part 2 of 8)

The Bet
by Karen Singer

Chapter 35 (Friday – week 5 Part 2 of 8)

As Chad was about to enter his cubicle, he caught sight of Robin’s cubicle just a short distance away. He wasn’t sure if Robin was there yet or not – probably not – but he suddenly remembered that she was planning on going to that aerobics class last night. As he dropped his purse into his desk drawer, he worried about it more than ever. Did she find out about him during her class? He sat down in his chair and hit the button to start booting up his computer, but he had to get up again and try to straighten out his skirt because it was all bunched up uncomfortably under him.
Once he got himself settled again, he watched his computer going through its startup process. But while it was doing that, all he could think about was what Robin might have heard at the gym last night – and how mad she might be at him because of it. He tried desperately to figure out the different ways that she might react? The more he thought about it though, the more convinced he was that she now knew everything that he had done at the gym last Monday – absolutely everything!
“Hi Chad,” Robin called as she paused briefly at his cubicle before continuing on to her own desk.
“Hi Robin,” Chad returned worriedly as he watched her walking away. She hadn’t said anything – yet. Was that a good sign? Less than a minute later, she was back. He couldn’t read anything from her face but she didn’t look as excited or as happy as she did yesterday. He mentally prepared himself for the worst.
“Wow! Another new dress!” Robin exclaimed, her face suddenly lighting up.
Chad was caught a bit off guard since he was expecting to hear all about what she had heard at the gym. “Uh, yeah. I think it’s nice.”
“Nice? Stand up so I can see it better.”
Once again Chad felt like he was being inspected. He dutifully stood up though to proudly show off his dress. He turned all the way around so she could see all of it. As he did so, he noticed the skirt of the dress flaring out a bit. He stopped when he was facing her once again, his skirt settling back into place again. “What do you think?” he asked, momentarily forgetting about her trip to the gym.
“I think it’s more than nice!” she replied. She shook her head. “I can’t believe that you’ve got yet another new outfit to wear! This one is a bit more… dressy, but it’s still good for the office. The shoes go great with it too. Are they new as well?”
Chad felt fairly happy from her comments. He glanced down past his breasts, past his flowing skirt, toward the shoes on his feet. Black sling-back pumps. He never wore them because they were a bit uncomfortable even though the heel wasn’t all that high. “No, I’ve had the shoes a while now,” he replied. “I just never wear them. To tell the truth, they’re really not all that comfortable. I only wore them today because I kind of figured they would go well with the dress.”
Robin let out a small laugh. “Uncomfortable? I’ll bet your seeing now that it’s harder being a woman than you thought. We have to put up with lots of little uncomfortable things like that in the name of fashion.”
“Yeah, I guess so,” Chad admitted. But his mind was thinking more along the lines of how uncomfortable his waist cincher was – not to mention his way too tight all-in-one girdle.
Chad sat back down in his chair. As he did so, he felt his skirt bunch up uncomfortably under him again. He pulled at it to straighten it out, but it didn’t work. He finally grabbed both sides of it and stood up just enough to let the material slide out from under him while he pulled it straight. He sat back down – much better.
“You might want to learn to do that a little more gracefully,” Robin noted, “like ‘before’ you sit down!”
Chad blushed. “Well, it’s usually not so much of a problem.”
“Yeah, but if you’re going to be wearing skirts… and that’s all I ever see you in now days…”
“Wait a minute! I wore pants on Wednesday.”
“Yeah, but that’s the only day you wore them this week!”
“You remember that?”
“Of course I do! And don’t tell me that you don’t remember what I wear every day!”
“I don’t even remember what you wore yesterday!”
“That’s crazy! How can you not remember?”
“I don’t, that’s all!”
Robin shook her head. “You’ve really got to start taking more notice of what everybody is wearing.”
“I don’t want to look like I’m staring at them.”
“You don’t have to stare. You just see it when you look at them.”
Chad shook his head. “How am I supposed to do that?”
Robin sighed. “You just do! Men! Or whatever you are!”
“I’m a…” Chad started to return, then stopped. “I don’t know.”
Robin laughed. “I don’t know either. But you’re certainly not looking like much of a man these days, even if you do act more like one.”
Chad didn’t quite know how to take that. “Well…” he replied, searching for some kind of response. “I don’t really have as much practice being a woman I guess.”
“Yet!” Robin finished for him.
Chad shrugged. “Yet,” he agreed. But if he won this bet then he would be finished with it all in another month. And even though he really liked the dressing up all the time, the bottom line was that he really wouldn’t be doing it that much longer.
“Hey, you know what?” Robin said. “When we go to break later, you should practice. Try to remember what everybody is wearing. You’ll never learn if you don’t practice.”
“I don’t know,” Chad replied uncertainly. “Everybody?” Mostly, it sounded like too much trouble – for nothing.
“You can do it,” Robin replied sounding like she had full faith in his abilities. “It’s really not hard at all.”
“For you maybe,” Chad complained. “I barely know what I’m wearing from day to day.” He really couldn’t see much of a reason to do as Robin suggested. Maybe it would be a good idea to get her off of the subject. “Hey, did you make it to the gym last night?” He was frightened to ask, but so far Robin hadn’t shown the slightest hint that she had heard anything about him. He had to know for sure.
“Oh yeah.”
“How did it go?” he asked, still searching for any clue.
“Let’s just say that I’m in even worse shape than I thought. I went home and soaked in a hot bath for an hour last night. And I still hurt!”
Chad was beginning to feel a bit better. Nothing about him at all. “Maybe you shouldn’t bother with the gym,” he replied. “You don’t really need it.”
Robin looked at him like he was crazy. “Are you kidding? Now I know I need it more than ever. Besides, since I spent all that money, my husband would hold it over my head forever if I don’t use it.”
Chad smiled. “Men!” he teased.
“Ain’t it the truth!”

Andrea watched as Mel’s first client of the morning walked out the door. There were a precious few minutes before the next client arrived. She picked up a stack of folders from her desk that needed attention and carried them to Mel’s office. The door was open and Mel appeared to be staring off into space with a rather distracted look on her face. “Mel?” she called from the doorway, snapping Mel away from whatever she had been thinking about. She held the stack of folders up so Mel could see them. “I can come back later if you like.”
Mel shook her head. “No, it’s fine. Come on in.”
Andrea walked over to her desk and deposited the folders. Mel barely saw her as she once again resumed staring off into space. “Tough case?” Andrea asked.
“What?” Mel replied, snapping back to reality again.
“Tough case? The client that just left.”
“Oh… No.” She waved her hand indicating that he had been nothing much at all.
“You look like you’ve got a big problem you’re trying to solve.”
Mel sighed a bit. “Sort of. But it’s really a silly one.”
“Anything I can help with?”
Mel looked Andrea in the face. “Maybe,” she replied. “Have a seat.”
“So what’s up?” Andrea asked as soon as she was sitting across from her boss.
“Well, I guess it involves Chad again…” She spent the next few minutes telling Andrea all about Chad’s friends having a poker game next week and about her continuing thoughts about it… and how she couldn’t get it out of her head. “It’s silly!” she finally said. “I don’t want him to go and he has no intention of going. He wasn’t even invited. But I still can’t stop thinking about it.”
Andrea thought about it for a few seconds. “Maybe your subconscious is trying to tell you something.”
“Like what?”
“I don’t know. But you’re probably never going to find out unless you send him to that game and let him play.”
“But I don’t want him there!”
“Of course not. But what could it really hurt? And like I said, unless you send him, you’ll never know.”
Mel thought about that for a minute. “Maybe,” she replied noncommittally. “Maybe.”
The sound of the outer door opening caught their attention. “That will be your next client,” Andrea said as she stood back up. She pointed to the stack of folders she had just placed on Mel’s desk. “And don’t forget to sign those!”