The Bet - Chapter 38 (Monday – week 6 Part 7 of 7)

The Bet
by Karen Singer

Chapter 38 (Monday – week 6 Part 7 of 7)

He certainly didn’t hurry as he spread out the disposable diapers all over that area of the floor. Many of the diapers he was spreading had been used just for this purpose before. But as he looked at all of them, he figured that they really needed something better than all those diapers to use. But if he asked Mel about it, it would be like proclaiming that he was planning on getting more punishment – which he certainly wasn’t! At least, not if he could help it.
Once the area was prepared, he let out a small sigh as he removed his apron and dress. He debated whether or not to remove his shoes and wound up slipping them off too. “Mistress, the area is ready,” he announced. The area might have been ready, but he wasn’t – not mentally or physically. He just had no excuses left for putting it off any longer.
Mel wandered over and eyed the area slightly as she headed to the corner to pick up her yardstick. Everything looked ready – except him. “Get that diaper off!” she ordered as she got into her usual place.
Chad moved slower than usual as he carefully pulled open the tapes on the single sodden diaper he was wearing. Forty whacks! Plus – how many? But the soaked diaper didn’t need very many of the tapes to hold it up and before he wanted it to, it slipped out of his hands and dropped down his legs to the floor. He stepped out of it, wearing nothing but his bra, waist cincher… and his chastity device. For all that, he felt totally naked.
“I really wish you weren’t being so stubborn over this,” Mel said as she watched him getting into place, leaning forward against the back of the chair in front of him. “I don’t ‘want’ to punish you… not at all. But I’ve got no other method to make sure you do what I want.” She watched as he slowly raised his bottom up into position, as if he was inviting her to hit him. “And in case you’ve forgotten the terms of this arrangement, what I want is all that matters!” With that, she swung the stick at his backside – hard!
The stinging slap of her yardstick actually surprised him more than usual - because she had swung her stick harder than usual. He stood up, curtseyed to her, and thanked her. Then he bent down and got into position again.
Mel didn’t know why, but the more she thought about him not talking the way she wanted all the time, the more frustrated about it she seemed to get. Swack! How hard could it be for him to use his sissy voice all the time? Everybody he knew at work already saw the way he was dressing – certainly not normal for a guy at all! They had to see exactly what he was – a sissy! Swack! So why couldn’t he do this one simple little thing? If he could wear dresses and heels to work – and everywhere else too, then why couldn’t he talk like a sissy all the time too?
She was trying to achieve something with him. Something important to her. She was trying to remove all his male… rights? Privileges? Traits? Manners? She didn’t know what. Swack! Didn’t he know how important it was for him to become what she wanted him to be? And wasn’t all this part of his fantasies too? Didn’t he really want it all as badly as she did? Swack!
She had to watch as he curtseyed again, but the little ritual that she usually loved, was frustrating her tonight too. It was going maddeningly slow! She had achieved so much with him already, but there was still so very far to go. And yet, it wasn’t so far. All her dreams… dreams that she didn’t even know she had! They were all so close she could almost touch them. Swack! They were things she wanted now, things she had to have. But he had defied her, and that wasn’t good! It wasn’t right! Under the terms of the bet he had to do anything and everything she told him to do. Swack!
It wasn’t that she was enjoying hitting him… not at all! But the swinging of her stick was like letting off steam. It was just all the frustration trying to get out. Swack! And for some reason, she was feeling more frustrated tonight than usual. It wasn’t right! He had defied her! He was personally trying to thwart her plans. He was trying to undermine everything she had accomplished. He was trying to ruin her dreams! Swack! Swack! Swack! Swack!
Chad had tried to stand up to curtsey and thank her once again, but suddenly she was raining hard punishing blows at him as fast and as hard as she could. He had to brace himself more than usual against the chair as the punishing, stinging blows hit him over and over again. What was going on? What had gotten into her? His backside soon began to feel worse than it ever had. He didn’t just cry, he wailed as her anger seemed to reach deep inside of him. He squirmed now, unable to stand still against the onslaught that was besieging him.
Mel couldn’t stop herself. “Why can’t you do what I want?” she panted as she continued to hit him over and over again. Suddenly he was crumbling under her continued blows. She hit him twice more on the way down. And then she realized she had overdone it – way overdone it. But it was like she couldn’t help herself. She forced herself to stop hitting him. He was crying uncontrollably, huddled in a ball. She had gone too far and she knew it… and suddenly, she felt very sorry. His pitiful crying touched something deep inside of her – made worse because she was the cause of his misery. She dropped to her knees and put her arm over him. “I’m sorry! I’m sorry!” she said over and over again, trying to sooth him. “Something just got to me and I lost control. I’m sorry. I’m sorry.”
Chad didn’t know if he was crying from the pain, or more from her temper. All he really knew was that he was miserable and so very sorry for not doing what she wanted. And all she really had wanted was for him to talk like a sissy – all the time. But could he really do it at work? That part, he just wasn’t sure about, despite the beating he had just gotten. But if he was going to feel like this after her punishments, then he might just have to consider it.
And then she was there, down on the floor next to him, not to punish him, but trying to comfort him. So strange. Why? He heard her saying she was sorry over and over again, but was she? He really didn’t care just then, but he did realize that as much as he feared her, it was also so nice to be comforted by her too. He felt her hugging him tighter, her head moving closer to his as she whispered comforting words in his ear. Maybe she was sorry.
He could feel the stinging pain in his backside, it felt terrible! But that was nothing compared to the pain of his emotions. And yet she was there with him, holding him, still trying to comfort him. He forced himself to at least slow his crying somewhat as he looked up at her. He saw nothing but concern… and was that caring… on her face. She pulled him closer to her and hugged him tighter. He heard her saying again how sorry she was. And despite the pain in his backside, and how emotionally horrible he felt, the words slipped out of his mouth. “I’m sorry too.” And he said it in his high-pitched sissy voice. He felt her respond by hugging him even tighter. And he hugged her back as he tried to get his sobbing further under control.
And then she was pulling away. “Come on,” she said kindly. “Let’s get you cleaned up.”
Chad let her help him a bit as he got to his feet. He saw her looking down at her pants, and stretching the material on one of her legs out a bit. He was shocked by the big wet spot he saw on her leg! He must have wet on her while they were laying together. “Oh no!” he exclaimed. “I’m so sorry! I didn’t even know I did that! I didn’t feel it again!”
Mel was a little surprised. He didn’t know? He didn’t feel it? But as nasty as what he had just done was, at the same time, those words thrilled her – because it was definite progress towards her winning the bet. “Don’t worry about it,” she said, trying to calm his fears. “I guess we’ll both have to get cleaned up now.” And then she smiled at him, trying to put him at ease.
While Chad was grabbing some of the diapers that were strewn all over the floor, Mel ran to her bedroom and quickly removed her pants. She grabbed a pair of shorts instead out of a drawer and quickly pulled them on before hurrying back out to him. He was still only wearing his bra and waist cincher so as he bent down to pick up more of the diapers from the floor, she got a perfect view of how red and raw his backside looked. She had done that to him. Usually, she would feel almost proud of it after punishing him, but not tonight. She had lost control tonight. All day long she had been in a bad mood – her damn period was probably to blame, but sometimes things just got to her. And unfortunately this was one of those times. And now, she felt sorry for what she had done. And it was time to fix it – somewhat. “Bring some of those diapers in here and lay them out on the bed,” she told him. “Let’s see what we can do about that backside of yours.” She was about to head into the bathroom but she paused to say one more thing. “And maybe you better hurry before you pee all over everything again.” She gave him one of her devilish grins before she walked away.
Chad’s bottom stung. It seemed to be worse with every movement he made. Bending down to pick the diapers up off of the floor seemed to make it hurt particularly bad. And unfortunately, he realized that maybe she did have a point. Maybe he should try to hurry, before he wet all over something else. That thought though made him pause for just a second. It was almost like he really was incontinent! That very thought thrilled him, then a moment later, worried him. Yes, it was his lifelong fantasy. But it still meant that she was making all too much progress against him for the bet. He had to find a way to gain more control back! And he had better figure out how to do it fast!
Since Mel seemed to be staying in the bathroom for a longer time than usual, Chad grabbed one of the diapers and taped it into place – just in case! He figured that she probably wanted him to lay down on all the diapers he had just put out on the bed, but until she told him what to do, he didn’t want to take any chances – especially not tonight. So what was taking her so long in there? That was one of the really good things about wearing diapers all the time, he never needed to worry about how long he was spending in the bathroom. In fact, he never needed to worry about going to the bathroom at all. Wearing the diapers was very convenient! And time saving too! Not to mention… fun.
He heard the bathroom door opening and she finally came out carrying a jar of some kind of cream with her.
“Why didn’t you just get up on the bed?” she asked as she saw him just standing and waiting.
“I didn’t know if I should or not,” he replied.
“Silly baby! Get that diaper off and get up there, face down. Let me put some of this on that bottom of yours.”
Chad removed the diaper he had just put on and laid down on the bed. At least Mel didn’t seem to be mad at him anymore – that was a major improvement! A minute later, he felt the icy cold sting as she plopped a bunch of the cream from her jar onto his raw backside. Then he felt the further pain as she began to rub it in. He hissed and squirmed at the pain. As tender and carefully as he knew she was trying to be, putting the cream on him hurt! Fortunately, she didn’t take too long with it. And then, a minute later, the pain on top of his backside was eclipsed by the feeling of her suddenly shoving another of the dreaded suppositories up inside of him. Argh!
“Turn over,” she said and he carefully rolled over onto his back, the still moist cream on his backside adding a new sensation as he carefully set his backside down on the diapers under him. And then she was spreading yet more of the cream all over his front side, what she could touch anyway. The darn chastity device covered all too much of it. “Do you want cloth diapers or the disposables tonight?” she asked.
She was dressing him for bed – already? “Disposables,” he finally answered. They weren’t nearly as bulky and when he wet, they would soak the wetness away from him better so he wouldn’t feel it as much. She taped four of the disposable diapers onto him, slitting each of the inside ones thoroughly to allow the wetness to leach through. He was surprised by so many diapers, but as he realized how early it still was, he thought that the extra diaper was probably a good idea.
Mel put the lid back on the jar of cream and stood back as he slowly worked his way off of the bed, obviously still in pain from the beating she had given him. “Go ahead and clean up the kitchen now.” Then she smiled a bit, “And get yourself a fresh bottle. And I want that bottle finished as quickly as possible!”
Chad dropped a quick curtsey, “Yes, Mistress,” he said in his sissy voice. And suddenly, everything seemed to be back to normal again.
Mel glanced into the kitchen every so often to watch him cleaning it up. He always seemed to manage to do it remarkable fast. She watched him constantly grabbing his bottle to get it finished – which was good. She had to keep him peeing. He finished with the kitchen before he finished his bottle, but not by much.
“I’m finished,” he said dropping another curtsey.
So nice. She loved seeing him curtsey to her like that. Yes, despite the problems, he was really coming along nicely. And he was indeed… something special.
“Is there anything else you want me to do tonight, or do you just want me to clean up the apartment a bit more?”
She thought about it briefly. “Not tonight, Sissy. You can go home now. I’ll be over later to leave you another note.”
Chad curtseyed again and began gathering up his things. He was still only wearing his bra, waist cincher, and now the diapers, but he only slipped his shoes on and didn’t even think about throwing his maid’s dress on over top of everything – even though anyone outside might see him during his short walk back to his own apartment. He grabbed his purse and fished his keys out of it. He turned back to her and dropped another curtsey. “Goodnight, Mistress.”
She nodded. “Goodnight, Sissy.” She watched as he walked out the door. Her apartment felt quieter the moment he left. She felt more alone. More… vulnerable? She continued to stare at the back of her door for a few moments, remembering that she had hurt him tonight. She had lost control. It had been a bad day from the moment she had gotten out of bed this morning. But that was no excuse, and she knew it.
So strange. She had sent him home. He was gone. The apartment was quieter. And she suddenly realized that she missed him. So strange. So very strange. “Good night, Sissy,” she whispered to the air. “Sleep tight.”