The Bet - Chapter 47 (Wednesday – week 7 Part 8 of 8)

The Bet
by Karen Singer

Chapter 47 (Wednesday – week 7 Part 8 of 8)

After Sandy left, Mel changed Sissy’s diaper, noting as she did it that his backside was still a bit bruised. As always, she put him on another hour and forty five minute time limit. But instead of letting him get dressed again, she left him wearing only his bra with his diaper and nothing else. “Okay, Sissy,” she said as soon as she had him ready, “ballet time again.”
Ballet time? Ugh! It had been a few nights now since he had had to practice ballet with her. While he loved seeing her do the dance movements, he wasn’t all that happy about doing them himself. But he supposed it beat standing on his perch in the corner. He went through the usual warm-up exercises with her, having to pause between each exercise while she made him “guzzle” some tea from his baby bottle. Then it was on to the next movement. But after the warm-up was over, she began teaching him exactly the routine she wanted. Chad was quick to realize that this time there was a big difference in the way she was going about it. This time she wasn’t continually trying different things to see how they looked. This time she seemed to know exactly what she wanted him to do from beginning to end.

Robin picked her crying son up from where he was screaming on the floor and held him and kissed him. He seemed to like getting into trouble and grabbing things he shouldn’t! She had only told him no! But he was getting tired now and the least little thing made him not just cry, but scream. Well, it would be his bedtime soon. She found his pacifier and stuck it in his mouth and cuddled him a bit more. It took a minute, but he finally stopped crying. She set him down on the floor where he immediately ran off as fast as his newly learned ability to run would let him – which seemed amazingly fast to Robin. Worried that he might try to find more trouble, she followed after him, but much more slowly. There was no keeping up with him! She had visions of him becoming a great track star when he grew up!
She got lucky. When she found him again, he was in the family room where her husband was watching TV. Her son had found his big toy truck to play with. She knew he wouldn’t play with it long before he moved on to something else – probably trouble – but the truck did seem to be his favorite toy – at the moment.
She sat down next to her husband and watched him playing. She loved him so much. He was so beautiful! So amazing! She felt so proud of him! But unfortunately, her thoughts were led to Sissy. The jerk! He acted like such a child! And so far, she found that dealing with him like a child made her feel the most satisfied as far as punishing him. Maybe as far as everything else went too. She simply didn’t dare not see him as a sissy anymore, because even now, after all these days, she still got angry. And she didn’t really like staying angry. She was still trying to make it up to her husband after the way she had behaved last weekend.
So she needed to keep reminding herself of what he was. What he really was! A sissy! It was just hard to do when she saw him every day because she had known him so long. She supposed that the old saying that old habits are hard to break was probably true. In this case anyway. So at least for now, she figured she needed all the visual reminders she could get. Anything that would let her constantly see him as a sissy – and nothing else.
But what did that mean? Images of him sitting on her floor sucking his thumb came to mind – along with an image of him in a dress, looking so much more like a woman than he used to be that it was almost frightening. But even though the fact that he was a man wearing a dress was supposed to mean that he was a sissy, so she figured, she didn’t really associate it that way. That woman image of him she still associated with an adult image. Maybe a different kind of adult, but still and adult. But that adult figure didn’t really help her as far as seeing him as a sissy. At least not the way he was dressed for work every day. It just didn’t help. So what could she do?
Her son was looking around now for something else to do. Even at one year old he seemed to be all boy. He liked playing with trucks and cars… and boy things. But Chad… or Sissy… was trying to be more… female. Or at least that’s how he saw his sissy side… and she supposed so did she.
Her son spotted her watching him and put a big smile on his face – she could see it even under his pacifier… and despite the drool and slobber that now ran down his chin almost to his neck. She held her arms out to him. “Come here,” she called. Laughing, her son got to his feet and ran, crashing into her leg where he held on and hugged her. She reached for one of her ever-present rags and removed the pacifier from his mouth and wiped his face clean again before putting the pacifier back in. “Is it bedtime yet?” she asked. But the only answer she received from him was to watch him take off straight for his father instead. It was his usual answer! No, he wasn’t ready for bedtime yet. But then, he was never ready for that!
Her thoughts turned back to Sissy. She wondered if he had a pacifier. Probably. That woman, Sandy, had been teaching him baby behavior? So she figured it would be very likely. Maybe a pacifier stuck in his mouth all day would help. An image of Sissy sucking a pacifier sprang to her mind… and seemed to overlay itself with an image of her son playing on the floor. There were differences. Huge differences. But… maybe some of those could be overcome.
Since she had a few minutes before she would put her son to bed, she went into her bedroom to search around.

Mel worked relentlessly with Sissy on his ballet, going over each of the mini-sections of the dance over and over again until she was satisfied with the way each one looked. She continuously had to stop to make him drink from his bottle, but drinking and making him keep wetting were her primary goal. Everything else she did was always secondary to that. It had to be!
She kept working with him until at one point during one of the easier movements, he seemed to pause as if he was confused. “What’s wrong?” she asked.
Instead of answering, Sissy looked down at his diaper and started feeling along the bottom of the leg band. “I think I’m leaking,” he replied in his new sissy voice.
Mel smiled as she glanced at the clock and noticed he still had a good ten minutes to go. “You’re getting better at this, Sissy,” she said.
Chad wasn’t sure if she was talking about getting his diaper to leak on time, or dancing.
“Maybe pretty soon we can see how well you can manage with an hour and a half.”
Ugh! Now he knew what she was referring to and he didn’t like that idea one bit!
Mel decided that they had done enough for one evening, although they didn’t really accomplish all that much towards his dance beyond the opening little bit she had planned.
But still, it was a good beginning. And the way she was working him, he was actually starting to look much better at what he was doing – in sections. Actually, much of what he was doing looked just plain silly, which was also something she was pleased with. “Okay Sissy,” she told him, “that’s enough of this for tonight. Go put something on my bed to protect it before we change that soaked diaper of yours.
Chad was glad they were done! He was starting to get really tired from all the exercise involved. And as much as Mel kept telling him that kids had no trouble doing all this over and over again, he wasn’t a kid! He was bigger, and the physical activity had taken its toll. He grabbed a stack of diapers that had been used before to protect either her bed or the floor and spread them out all over the top of her bed. Unfortunately, he knew the protection was absolutely necessary. When he was in this state, where he was on a constant time limit for leaking, he no longer had any control over where and when he was going to pee. It usually came as a complete surprise to… everyone.
As he was finishing laying out the diapers, Mel came in with a bunch of ropes in her hand and began fastening them to her bed frame. He wasn’t at all glad to see them, although he had to wonder why she would even bother. He wasn’t going to go anywhere, especially not when she was going to change his diaper for him.
As soon as Mel had her ropes ready, she had him climb up on her bed where she restrained him with his arms straight overhead and his legs spread-eagled. Then she pulled open the tapes holding his soaked diaper closed.
Chad expected her to just pull the wet diaper out from under him and stick a fresh one in its place, but he was surprised when she unlocked his chastity device instead. Now he knew why she had restrained him – to make sure he couldn’t touch himself down there while the device was off! Piece by piece he felt her removing it, till at last his penis was feeling the cool fresh air of the room. He was now so used to the heat inside the device and inability to feel anything down there that the sensation of the cool fresh air was almost a shock. Unfortunately, it was shock enough that five seconds after the air hit it, he started peeing again.
Mel had turned to the side to pick up all the pieces of his chastity device from the end table next to her bed so she didn’t see what was happening right away. It wasn’t till she turned back toward him with her hands full that she noticed what was happening. As fast as she could, she dropped the pieces on his stomach and pulled the wet diaper back up between his legs again. “I should know better by now!” she berated herself. “You can’t be left unprotected even for a second!” She smiled wickedly down at him as she picked up all the pieces to his device again before leaving to go clean them.
It was times like that, when someone caught him peeing uncontrollably, that Chad felt very humiliated… not to mention excited. Wasn’t that the feeling he had always dreamed of experiencing? He just wasn’t totally incontinent – yet. Not by a long shot. And with the short time-limit of this bet, he never would be. Too bad. But winning the bet was too important to him to even think about giving in.
Mel came back a few minutes later, most of the plastic pieces in her hands still dripping wet. She set them down on an out of the way part of the bed on top of one of the diapers protecting things. Then she took a good look at his tiny penis. Yes, it still appeared to be just as tiny as ever. Much more so than when they had first started this bet. She grabbed what little of it there was between two of her fingers and moved it around a bit to take a close look at it. As far as she could see, it looked just fine. No sign of any sores or irritation – other than the faint red marks from where the teeth from the device stayed in contact with his skin all the time.
She unfastened one of his legs and had him turn over so she could inspect his backside. As soon as he rolled over, she got a better view of the bruises still covering each of his rear cheeks. She could tell they had been heeling, but there were still places that were not only an angry red, but some spots were definitely still black and blue. And it looked like they might stay that way for a few days. She had no doubt at all that it still hurt him to sit down.
“Jillian did this to you?” Mel asked.
Chad was tempted to reply with “Yes Mistress,” in his sissy voice, but he opted to just say the word, “Yeah,” instead. The other way was much more humiliating and difficult because of all the S’s in it. Fortunately, Mel didn’t seem to notice.
“Maybe I need to have her give me some lessons in how to beat you properly!” Mel stated teasingly. It looks like she gives you a lot more to think about than I do. Obviously, I’m falling down on that job!”
Chad didn’t think so at all! But he said nothing for fear it would only lead to more trouble for him.
Mel carefully coated his bruised backside thoroughly with a cream to help heal it and to protect it from whatever else his diapers would press up against it. Then she pulled out her jar of suppositories and stuck one way up inside of him. He was getting less and less of them now, so every one she did give him seemed to be more important. Then she rolled him back over onto his back again where she heavily coated his penis with the same cream before putting his chastity device back on him and locking it shut.
From the position Chad was laying in, he couldn’t see what Mel was doing, but he could certainly feel it as she put each piece back into place. Each one feeling more and more familiar as the device was rebuilt. Till with one final click, the lock clicked home, securing everything and leaving him no way to touch or even feel that part of him. As used to it as he was, it was still very frustrating to him, not to mention that the sound of the lock still sent a momentarily twinge of panic through him. But all the manipulation Mel had just done with that part of him, and probably coupled with the shock of the lock clicking back into place again, suddenly made him pee all over again.
“Goodness!” Mel exclaimed as she quickly pulled the soaking wet diaper that was still under him back up over him again. This is becoming more and more difficult!” She looked up at his face. “Not that that’s a bad thing,” she teased. As soon as Mel was certain he was finished again, she pulled the wet diaper away and substituted a fresh dry one from a stack that she had already prepared.
Since it was still fairly early, Chad figured she would leave him in only one diaper again with another hour and forty-five minute time limit. But he was surprised when she started loading multiple diapers on him again – four of them! All followed by a pair of his plastic panties.
When she was done, she released him from the ropes. “That’s enough for tonight,” she told him. “I have other things to do tonight. Don’t forget to drink all your bottles before you go to bed.”
Chad got up from her bed and grabbed all his things, which fully loaded his arms. He tried to drop a curtsey for her, but with his arms so full, it was only an attempt. She didn’t seem to mind though. “Good night, Mistress,” he said in his new sissy voice, lisping the last part of the word mistress.”
“Good night, Sissy,” Mel replied, without bothering to get up from where she was sitting on the side of her bed.
She stayed there till after she heard the door closing. Then she headed back out to her kitchen where she started making a fresh batch of tea for him. While that was making, she again turned to her laptop to write to Robin. This time, she did have something to tell her. It wasn’t much, but it was something.