The Bet - Chapter 49 (Friday – week 7 part 6 of 6)

The Bet
by Karen Singer

Chapter 49 (Friday – week 7 part 6 of 6)

Instead of their usual Friday night restaurant, Mel drove straight home. Chad was glad because he didn’t want anyone to see his new fingernails. “Just fix me a salad for dinner,” Mel ordered as soon as they were through the door. “And hurry up with it. And don’t forget to drink another bottle! You’ve only got a few minutes left till your deadline!” Then she headed straight for her bedroom where she closed the door.
Chad glanced at the clock and saw that she was right. He only had about fifteen minutes left. And worse, while he was very wet, he doubted that he was anywhere near wet enough to be leaking in that amount of time. But still, he had to try! He quickly grabbed a fresh bottle of tea from the dwindling supply in her refrigerator and started drinking furiously – while he attempted to make her a salad.
When her salad was made, he quickly set the table and poured her a drink. But now he was down to the final minutes. With his eyes glued to the clock, he continued to drink… and will himself to pee. But while he did pee, it wasn’t nearly enough. As the final seconds ticked down, he heard her coming back again.
“Are you leaking yet?” she asked.
He turned to her. She was once again dressed in shorts and a t-shirt – the clothes she wore lately whenever they were practicing ballet. A wave of defeat and fear washed over him. He curtseyed. “No, Mistress.”
“I thought as much,” Mel said with some disgust. She knew it was because he couldn’t drink anything while they were in the nail salon, but rules were still rules. “Keep trying and get the floor ready while I’m eating,” she ordered. She sat down to eat, and Sissy ran off to find everything he would need – to get punished. “I hope you start leaking soon,” Mel called before she put anything in her mouth. “We have other things to do tonight!”
Chad figured those other things were ballet practice – and more ballet practice. He spread disposable diapers out all over the required area of the floor. He kept drinking as he worked. He was peeing more frequently now, but he still wasn’t leaking. With the floor all prepared he wasn’t sure what to do next since Mel was still eating.
“If you’re finished there, get up on your perch and stay there till you leak!” Mel called from the kitchen table.
Chad checked his bottle, it was almost finished. Despite not wanting to stand on his perch, he ran to the refrigerator to get another one. Every minute that he wasn’t leaking would mean additional punishment that he didn’t want. He had his bottle to his lips and was drinking furiously as he wandered much more slowly back to his perch – where he carefully climbed up onto it and leaned into the corner.
Leak! Leak! Leak! He could feel himself peeing again, but how long would it be before he started leaking? And would Mel really go through with her planned five swats for each minute he was late? He really hoped she wouldn’t! Pee! Pee! Pee! Leak! Leak! Leak!
It didn’t take Mel very long to finish her dinner. It was good, but her mind was on other things. Like how was she going to make him totally incontinent in only two more weeks if he could still hold back for five minutes? It seemed insurmountable.
With no answers to the troubling question, she purposely turned her mind to happier thoughts. She really loved his new nails. Just thinking about them nearly made her laugh. They were perfect for him. But as much as she enjoyed his discomfort over them, it only barely blunted her worry over winning the bet. What was she going to do?
She was just getting up from the table when she heard him calling from his corner that he was leaking. “It’s about time!” she exclaimed. She glanced at the clock. Eleven minutes late! And she had decided to give him five swats now for each minute! Fifty five swats. They were going to be at this for a while. She just hoped he would be able to dance when she was finished!

Totally naked from the waist down, Chad finally leaned over and put his hands against the back of the chair to brace himself. He hated this. It wasn’t his fault his diaper hadn’t leaked in the hour and forty five minutes she gave him. It was just that… their nail appointment had kept him from drinking enough. And the diaper probably was one of those that could take a bit more than others. Even though all his disposable diapers looked the same, he was getting fairly sure that some of them were more stubborn about leaking – probably just to spite him. Bracing himself one more time for what was to come, he raised his backside up high in the air, making it the perfect target for Mel’s stick… inviting Mel to punish him.
The awful swish of her stick flying through the air came all too quickly, as did the stinging pain the moment it hit. He stood up and curtseyed. “Thank you, Mistress,” he said, lisping in his new sissy voice. Then he leaned back again, preparing for the next one. Fifty five swats from her stick. He had only received one so far, and already his backside stung terribly.
Mel swung her stick firmly again the instant she saw his backside raised into position. She was hitting him hard, but not nearly as hard as she was capable of. And she was trying to waist as little time as possible since it was going to take so long. But she did love seeing him have to go through all the motions of the exercise each time… first inviting her to hit him by raising his backside up for her, and then curtseying and thanking her for each one. She really loved that. He was so… ridiculous!
She was glad to notice before she had started that the bruises from a few nights earlier had now faded to mostly nothing. There were a few spots she could still see, but nothing that really concerned her. Nothing to make her hold back on his punishment at all. Swish - Smack!
It didn’t take long before she saw the tears rolling down his cheeks. A few swats later and she saw him peeing on top of all the diapers – purposely ignoring the fact that he was peeing like he was supposed to. A little while later, his voice started to get harder to understand each time he thanked her – not that she minded because that too was funny. As his punishment continued, his crying became harder and harder and his movements grew slower and slower, but she kept him at it. She saw him peeing yet again about half-way through, then still again shortly before she finished. Both times she saw him start to look down at what he was doing, then pull his head away quickly as he tried to ignore it. She only laughed at him. So pathetic!
And finally, she delivered the last swat and watched as he stood up and thanked her one more time. His words were totally unrecognizable – as they had been for a while now. Mostly, he was just crying and mouthing the words. But he was miserable and that was the point. A few minutes later, she had rediapered him and set him on yet another hour and forty-five minute time limit. She still didn’t relish punishing him when she knew that he didn’t deserve it, but at the same time, there were elements to it that were definitely enjoyable.
“Get up into your highchair, she told him as soon as he was ready. “I’ll get your dinner.”
Still blubbering slightly, Chad headed for his highchair. He removed the tray himself and started to get up into it. His freshly punished backside protested the moment he started to climb up, but having little choice, he forced himself to endure it. Mel came over and put the tray in place and tied one of his bibs around his neck before going back to finish preparing his dinner. A few minutes later, he was eating baby food with a tiny rubber coated spoon held in his left fist. A fresh baby bottle of her lousy tea was on his tray for him to finish too.
As bad as the baby food was to eat, and as much as his backside was still protesting that he was sitting on it, this was much better than being punished. He fervently hoped that his diapers wouldn’t be stubborn anymore tonight. Five swats for each minute over was way too many. He didn’t think he could take it again.
While Chad was eating, Mel turned on her stereo system and cued up the music he would be dancing to. But that only took a moment. She was anxious to get on with is dance practicing. He was eating, but with the tiny spoon she had crippled him with, there was no way he could eat much faster. Finally, he was done! She carefully wiped off his face and hands and released him from his highchair. There were only a few dishes that needed cleaning, but she told him to ignore them. She was ready to get on with his dance lessons.
Since she hadn’t let him get dressed again after his punishment, he was all ready. She did notice though that he was moving a bit stiffly still as he walked into the living room. She noticed his stiffness again as they started warming up. But fortunately, the longer she had him moving and dancing, the more his body seemed to loosen up. Before long, they were again working diligently on the ballet routine she had choreographed for him. The routine he would be performing on Sunday night.
They had been practicing for a little over an hour when her phone suddenly rang. She was bothered for two reasons, first because it was an unwanted interruption, and secondly because as she hurried to answer it, her mind began to worry that the call might be work related – someone needing legal assistance at this hour. It was for that very reason that she preferred doing mostly contracts and paperwork instead of defending people. She picked up the phone. “Hello?”
“Mel? I just wanted to see if there was any chance at all that you might go out with me sometime.”
“Derek! You’re back!” Everything that had been running through Mel’s head totally faded to nothing as soon as she had realized who was calling.
“Yeah, I got in a little while ago. And I know this is late, but I just wanted to check to see if there was any chance at all that you might go out with me.”
Suddenly the prospect of going out with him was all that she could think of. She quickly remembered that he was the one that she had wanted to go out with in the first place after that poker bet. But things hadn’t quite worked out the way she wanted. But still, Ray had been… great! And now Derek was back! “Any chance? Of course there’s a chance! A very good chance!” she replied as her excitement grew.
“Really? So… when would you like to get together?”
“When did you have in mind?” she asked.
“How about tomorrow night?” Derek replied. “I have some things to do during the day since I’ve been gone, but I can pick you up around… oh say, five? Is that too early?”
“No. That’s… fine.”
“Great! See you then.”
“I can’t wait!” As Mel hung up her phone, she realized that it was true, she couldn’t wait. She didn’t know why going out with Derek should make her so excited, but it did.
She glanced up at Sissy. He was drinking his bottle, watching her. Was that a look of disapproval on his face? So what if it was! She was going to go out with Derek tomorrow night whether he liked it or not! And he could just… he could just… Oh shit! What was she going to do with Sissy – again! That was the only problem with these dates right now. Until this bet was settled, there was no way she could let him go unsupervised! Her first thought was Sandy. Wasting no time, she dialed her number. Fortunately, Sandy answered fairly quickly. “Hi Sandy.”
“Hi Mel. What’s happening?”
“I need another favor. Are you interested in babysitting again?”
“Sure. When?”
“Um… tomorrow night. I know it’s kind of short notice, but Derek just called me now.”
“Derek? So he’s back?”
“He just got home. So are you available?”
“Yeah, no problem.”
Mel felt relieved. “Great! You don’t know how much I appreciate this.”
“No problem, Mel. The only thing is, that I really wish I could come up with something special to do with him. But I still have no idea what!”
“So I guess Robin couldn’t help you?”
“To tell the truth, I don’t think she really even wanted to talk to me.”
“Sorry to hear that. But if you do think of something, don’t forget to tell me. I don’t want to miss it!”
“Yeah, I will. I promise. Say Mel, um… just in case I do come up with something, did you ever get his pink dress cleaned? I’d kind of like to have it available tomorrow, just in case.”
“Oh, I’m sorry! I didn’t think about it. But tell you what, I’ll have it cleaned first thing tomorrow morning so you can have it. Okay?”
“Great Mel. Now all I need is a good idea. Do you have any?”
“Sorry, not a clue.”
“That’s what I was afraid of. But no problem anyway. You know I’ll be glad to look after him.”
“Thanks, Sandy. See you tomorrow.”
Mel hung up the phone. That had been easier to arrange than she had anticipated. And tomorrow night she would be going out with Derek. She wondered how he would be on a date… not to mention in bed. Ray had been fantastic – in both areas. But there had just been that little something missing with him. Everything had been fantastic but a little too artificial. How would Derek be? And then she remembered that Gloria would be going out with Ray tomorrow night – while she was out with Derek. She hoped her friend would have just as good a time with him as she had.

Sandy looked over at Cassie. “I’m going to be watching Sissy again tomorrow night.”
“Okay,” Cassie replied, not really caring at all.
“I still wish I could come up with something special to do with him.”
“Well I certainly don’t have any ideas.”
“I know, but there’s got to be something!”
“Why don’t you call Jillian and ask her? Of course you could always take him over to her place again and let her beat him all night again.”
Sandy was horrified by the thought. “No way! I was scared to death she would really hurt him last time! But still… you’re right. Maybe she can help me think of something.” She picked up her phone again and dialed her friend. “Hi Jillian, it’s Sandy.”
“What’s up?” Jillian replied.
“Hey, remember Sissy last week?”
“Of course! How could I forget? You want to bring him by for another go?”
“No, not this time. But I’m going to have him tomorrow night again, and I’d really like to come up with some kind of special way to show off his baby side – you know, his total baby side.”
“So why don’t you bring him here again? We can let him be a baby all night if you like.”
“No, I think what I want is something where… maybe more people can see him. Something that will really show off how much of a baby he can be.”
“Sorry, I can’t help. I don’t have a clue other than we can invite a few others over.”
“Yeah, but like I said, I really want to come up with something different.”
“How about Greta’s. Why don’t you talk to her?”
“Greta? You think…”
“Maybe. I don’t know. But what can it hurt to ask?”
“Yeah. Maybe she’ll let us do something… or maybe she can come up with some other idea for me. Thanks Jillian. I owe you!”
Cassie was staring at Sandy. “Greta’s?”
“Yeah, I wonder if we can do something there?”
“They’ll eat him alive!”
Sandy thought about that for a moment. “Yeah, they probably will.” But then she thought of something else. She picked up her phone again and called Mel back. “Hi Mel, it’s me again. Listen, if I’m going to have him tomorrow night, then I’d rather not have him here earlier for his, uh, baby lessons. Besides, I have something I need to check on for him then.
“No problem,” Mel replied. No problem at all.” Mel hung up her phone again. It sounded to her like Sandy might have finally come up with an idea. She put Sandy quickly out of her mind though as she went back to making Sissy practice his ballet.
She didn’t call a halt to their practice till fairly late again. Then she took him into her bedroom and once again removed his breast forms for the one night of the week she allowed him to go without them. When she was done, she diapered him again for the night, this time actually sticking one of the suppositories that he hated so much up inside of him. He had missed the last three. She dared not let him go without this one.
A few minutes later, she said goodnight to him. But as the door closed behind him, part of her thoughts were on Sissy, and part of her thoughts were on Derek… and Ray. Two really handsome guys. Two hunks! She had gone out with one of them last week, and now tomorrow she would be going out with the other. And she couldn’t wait. But even as she thought about it, some small part of her felt guilty about it. Guilty… because of Sissy. “Good night, Sissy,” she said in her mind. “Good night.”
Then she went back to thinking about Derek… and Ray.