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

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.