The Bet - Chapter 42 (Friday – week 6 Part 8 of 8)

The Bet
by Karen Singer

Chapter 42 (Friday – week 6 Part 8 of 8)

Chad knew he was in trouble as they were driving home. It had been a very long time now since he had put his single diaper on and called Mel to tell her. But he wasn’t leaking yet. He was certainly very, very wet. That much was for sure. But he wasn’t leaking. Now, after dinner and the two large glasses of iced-tea, he was wetting fairly heavily again and often too, but he hadn’t started leaking yet. He was becoming more and more concerned about it – and even more concerned over his punishment for not leaking on time. And speaking of leaking… “Um… Mistress.”
“Yes?”
“Um… Can I wash my sheets tonight… please?”
“Wash your sheets? Why can’t you do it tomorrow with the rest of your things?”
“Because I leaked all over them last night.”
“You leaked? And you were wearing how may diapers last night?”
“Four?”
“Four diapers and you still leaked?”
“I had way too much to drink!”
Mel just looked over at him wickedly as she drove. “Never!” She went back to concentrating on her driving, but a minute later added softly. “We’ll have to try that again – very soon!”
Mel finally pulled into her parking space and turned the engine off. She glanced at her watch. “Okay, Sissy. By my watch, you’ve only got thirty minutes left to get that diaper leaking!”
Chad was surprised. What had happened to an hour and forty five minutes? Not that he was about to complain. They had been gone for well over two hours now and he wasn’t looking forward to the beating he would have received. And as wet as he thought his diaper was, he was fairly sure he could make it leak in the next thirty minutes – hopefully. “Thank you, Mistress,” he replied gratefully as he got out of the car.
Mel had been very aware of the fact that she hadn’t given him enough to drink this time, but by not telling him, she was fairly sure that he hadn’t been holding back at any time. So hopefully, nothing lost there. Besides, she had other plans for him tonight that didn’t include punishing him.
Chad hurried up to his apartment where he quickly pulled the sheets from his blow-up mattress. He wondered briefly if Mel wanted him to wear his maid’s uniform again. But she hadn’t said anything about it so he left on the clothes he was already wearing as he carried the sheets over to her apartment. Before putting the sheets into the wash, he went to her refrigerator to grab himself another bottle – if he was going to make even this extended deadline, then he absolutely had to keep drinking! But when he opened her refrigerator, he was shocked to see that there were no bottles left. He knew her supply had been running low but he didn’t realize that she had none left at all. Even his own supply at home was nearly used up. Did he dare mention it since her lousy green tea tasted so… lousy? He grabbed one of the empty bottles from her cabinet that he had washed earlier in the week and filled it with water. The lack of taste was certainly an improvement over her green tea mixture. He drank continuously as he walked back to the washer to load his sheets into it.
While Sissy was busy getting something to drink and loading his sheets into the washer, Mel changed into a pair of shorts and an old t-shirt. Then she wandered out to her stereo system and began looking through her collection of classical ballet music. If she was going to have him perform a little ballet in public, then she needed to choreograph something for him, and for that she needed the right music. Ah! Swan Lake! One of her favorites. Perfect!
She turned to see what Sissy was doing. The washer was already running and he was just standing there next to it, drinking from his bottle. She glanced at the clock. Time was about to run out for him. “Sissy!” She waited till he turned toward her. “Show me your diaper!”
Her command was the last thing that Chad expected. As fast as he could, he grabbed the hem of his skirt and pulled it up as high as possible, totally exposing his soaked diaper underneath.
Mel shook her head as she headed for her yardstick in the corner. “Just stay like that,” she commanded. “It wasn’t fast enough again. One way or another, we’re going to get you conditioned so that doing it faster becomes like a reflex. You won’t have to stop to think about it anymore!”
Chad watched with growing trepidation as she grabbed her stick and approached. He had tried to pull his skirt up fast enough, but she had simply caught him off guard with the command. And now he was about to pay the price. He stood there as she walked around behind him and off to the side a bit. He squinched his face up preparing for the pain that he knew he was about to feel.
“You will…” Swish, smack!
Chad jumped as her stick stung the top of the back of his legs, just below his soaked diaper. Wow did that hurt!
“Do it…” Swish, smack!
Again the stinging pain erupted on the back of his legs. But this time, the moment the pain erupted again, his pee also erupted out from the other side.
“Faster!” Swish, smack!
Chad couldn’t believe how much her yardstick was hurting him. She was obviously swinging it extra hard.
“You will...” Mel repeated as she again swung her stick hard at his exposed skin on the back of his legs. “Do it…” And again she swung her stick hard. “Faster!” she finished with one final and extra hard swat. She backed off and could see how red the area was where she had hit him… after only six blows. “If you don’t learn soon, we’re going to have to come up with a more convincing way to teach you.” And then she noticed what Chad himself hadn’t been capable of feeling yet, the little thin line of wetness escaping out from his diaper and just starting to run down his leg. She glanced up at the clock. “Two minutes too late,” she told him.
Chad wondered what she was talking about. “Two minutes too late for what?” But instead of answering, Mel swung her stick again at the back of his legs. “You’re leaking,” she said right after she hit him. She swung one more time. “And it’s two minutes too late!”
With the stinging pain from her yardstick, Chad couldn’t even tell he was leaking. All he felt was pain.
“Now hurry up and get yourself another diaper. We have other things to do tonight.”
Chad ran for his diaper bag and pulled another diaper out of it. Only two swats for being late? Talk about lucky! He brought the fresh diaper back to Mel so she could change him.
“Do it yourself,” she told him. “And you better hurry up. Your hour and forty five minutes started five minutes ago!”
Five minutes ago! She was making it more difficult once again! As fast as he could, he removed his soaked and leaking diaper and put the fresh dry one on. It felt so totally different from the squishy heavy one he had just taken off. In some ways it was more comfortable. But in other ways it was a lot less interesting to wear! The problem now was that he had to make it interesting as fast as possible – too fast in fact. He grabbed the bottle of water he had been drinking and started working on it before he disposed of the used diaper he had just taken off.
Mel went back to her stereo and loaded the disk for Swan Lake. She found the track for the music she wanted and turned it on to listen for a minute. Beautiful, just beautiful! She looked to see what Sissy was doing. He was back to drinking furiously from his bottle again. She noticed that whatever he was drinking looked awfully clear. She didn’t really care, as long as he kept drinking. But now she wanted him to do other things besides just drinking. “Sissy, get over here. It’s ballet time again.”
Chad knew it was coming. He just hoped it would come later rather than sooner. He carried his bottle around to his usual place next to her sofa, grabbed the back of it with one hand to steady himself, and put his feet into the awkward first position.
Mel watched Sissy getting into place. Some things about what he did pleased her greatly, but something bothered her tonight. She was about to get much more serious with his ballet lessons, so… “Sissy, get undressed. Just leave your bra and diaper on. You won’t be able to dance properly with everything else.”
Chad got undressed - mostly, leaving just his one diaper and his bra with the falsies glued to his chest. He was mostly glad to be rid of the darn waist cincher he had to wear all the time. He felt much more comfortable without it. But once he got back into position at the end of her couch again, he discovered that for some reason, even just in front of Mel, he felt much more embarrassed about being exposed in only the one single diaper. How strange. He was also embarrassed to suddenly realize he was peeing again. Oh well, he guessed he better be. His deadline could come awfully fast and it was difficult to keep drinking while doing ballet.
Mel began trying to teach him what little she remembered from the tiny pieces of the ballet she had done in her childhood dance recitals – which didn’t amount to very much. But at least it was a starting point. Trying to remember exactly what she had done was difficult. Trying to teach it to Sissy was even more difficult since he didn’t have a clue about any of it. But her biggest problem turned out to be something else entirely. It was something that was really just a bit of a distraction at first, but it became more and more of a distraction as time went on. That was the sight of the single flimsy diaper he was wearing – that gradually grew wetter and wetter as she watched.
The wetter his diaper seemed to get, the more she noticed it and the more it made her keep looking at the clock to see how much time he still had till he was supposed to be leaking. It also kept reminding her that he needed to keep drinking more than he needed to be dancing, so she kept calling brief break periods so that he could drink from his bottle – or so he could go get another bottle. And when the washing machine kicked off and it was time to move his laundry into the dryer, that was another distraction.
Finally, with only fifteen minutes left for him to be leaking, she called a halt to the dance practice entirely. There were just too many distractions. Plus, she finally realized that the real reason she was so distracted was because she didn’t really know what she wanted the dance to look like yet. She didn’t have a full idea yet of what she wanted him to do. She needed more time to figure that out. For something as complex as what she had in mind, she needed to plan better. “Okay, Sissy, we’re finished here for tonight. Get your laundry out of the dryer… and finish that bottle! As soon as you’re done, meet me in the bedroom.”
Chad was glad to be finished. She had told him to do one thing, then she would change her mind and make him do it differently, over and over again. He was now more confused about ballet then when they had started – which really didn’t bother him at all.
He took care of his now clean and dry sheets and set about finishing his latest bottle of water. He was peeing automatically again – he had been since the restaurant, or earlier. It was hard to tell. And once again, he didn’t always notice when he started peeing. If he was busy concentrating on something else, then it was like his body was forgetting to tell him about the other. He wondered if there were times when he was peeing and he didn’t know about it at all. Possibly. But since he didn’t know about it, he couldn’t tell for sure.
When his bottle was finished, he went into Mel’s bedroom. As he suspected, her bed was prepared against any of his “accidents” and the ropes to bind him were already out and in place. Within minutes, he was firmly tied to her bed, which he thought was ridiculous because he had noticed the jar of glue remover already out on her nightstand. Obviously, she was planning on removing his glued-on breasts again – and he wasn’t about to fight her over that one little bit. He was actually looking forward to getting that weight and bothersome feature off of his chest for a while. Even if it was just for a while.
Just as she had done for the last few weeks, Mel slowly and carefully removed the breast forms from his chest. As each one was finally lifted off, he felt a huge sense of relief as the weight was finally gone. He noticed as she did it that she never once said a word to him. Through the entire process, Chad got the impression that her mind was elsewhere. She was there with him… but she wasn’t. Once the breast forms were removed, she unfastened his now very soggy diaper. That too felt strange as it was pulled away from his front side and she let it drop down between his legs.
Mel pulled his soaked diaper back, exposing his chastity device underneath. The diaper itself was so wet that she couldn’t believe it hadn’t started leaking yet. He was lucky tonight that she had too many other things on her mind and wasn’t overly interested in punishing him unless she saw that it was necessary. She carefully checked his tiny penis inside of the device. Just as tiny as ever. Perfect! Those teeth inside of the device really were affective!
She needed to wipe him off next. She turned away and grabbed a wipe out of the box she had on her nightstand. But when she turned back, she was surprised to see a small stream of pee rushing out from the end of his device. Fortunately, it was all rushing down onto the soaked diaper still underneath him. She looked up at his face. There was no hint there that he even realized what he was doing. But of course he realized it. He had to realize it. He probably just didn’t care! She suddenly saw him look a bit startled and he lifted his head, trying to see down toward the “business” end of things – which he really couldn’t see all that well. He briefly looked up into her eyes. Was she wrong, or did he seem to be a bit embarrassed. Well, she would have probably been embarrassed if she were him. She waited till he finished peeing again before she wiped off his front side.
She untied his legs next. Then she opened the jar of suppositories and pulled one out to have it ready. With his help, she lifted his legs way up into the air and up toward his head, totally exposing his backside. She pulled the soaked diaper out from under him and pulled four of his cloth diapers into place. Then she wiped his backside off carefully and before she set his legs back down again, shoved the suppository way up inside of him. Since he hadn’t gotten one last night or today at lunch, there was no way she would let him go without one now.
She let his legs back down and began the arduous chore of trying to pin so many super thick cloth diapers on him. It took her a long time to manage it and her fingers hurt before she was done, but she did finally manage it. Of course one of the reasons that it took longer than usual was because her mind was only partially on the task. A fresh pair of plastic panties soon followed to protect everything, and he was ready. She finally untied his hands and let him to his feet.
Chad gratefully stood up and breathed in deeply without the extra weight of the stupid breast forms. He noticed though that his chest felt strange now without them. As he moved, he also noticed how odd it felt for his arms to move in certain ways and not come in contact with them. Obviously, he had been wearing them for way too long now!
“Get your things together and go home now,” she told him, which was exactly what he expected her to say. “We have a busy day tomorrow,” she added – which wasn’t exactly what he expected to hear. He briefly considered asking her what was going on, but thought better of the idea. If he knew, then he might stay awake all night worrying about it.
He had trouble waddling around in the super thick diapers, as he gathered up his things. They were so thick and stiff that walking normally was completely out of the question. The awkward waddling he was forced to adopt wasn’t all that easy either. But once he had everything, he went back to her bedroom where he saw her still sitting on her bed, seemingly staring off into space. “Goodnight, Mistress,” he said as he tried to curtsey a bit with his arms full and the super thick diapers forcing his legs wide apart.
Mel snapped back to reality at his words. She smiled half heartedly. “Goodnight, Sissy. I’ll be in later to leave you a note as usual.” She watched as he attempted to curtsey again and failed miserably. She almost laughed at his attempt. Then she sat there and listened as he walked out and closed the door behind him.
She continued to sit on the bed as her mind tried to sort through too many different problems. Problems she wasn’t totally aware that she had – till now.
What was she going to do about teaching him a ballet that he could perform in public? She could of course easily drop the idea, but now that it had fully set in, she wasn’t about to even consider that course of action.
How was she going to completely overcome his ability to control himself? The only way she could clearly see right now was to keep doing just what she was doing. But was it enough? She worried about that constantly.
And then there was the biggest item on her mind. Her one piece of unfinished business for the day. Her business that had gotten ruined by odd events earlier. In a nutshell… What was she going to do about Robin?
She got up from her bed with all those things on her mind as she went into the kitchen to make herself a fresh pot of coffee. While the coffee was brewing, she got out her big pot and began making more tea for Sissy. She had let their supply run way too low. Making tea would be a good task for her to do while she considered things and tried to figure out her best course of action. Tomorrow would be a busy day. And tomorrow, she had to make some decisions – one way or another.
Her mind skipped back to Sissy, alone in his apartment. Was he still drinking his required three bottles before bed, or had he finished yet? Not that it mattered. She silently wished him a goodnight as she stirred the strong green tea mixture in her pot. “Good night, Sissy… Good night.”