The Bet - Chapter 37 (Sunday – week 6 Part 7 of 7)

The Bet
by Karen Singer

Chapter 37 (Sunday – week 6 Part 7 of 7)

Mel’s hunger for sex grew rapidly as she watched him laying out towels over half of her couch. She had one thing on her mind, and getting to that one thing couldn’t come soon enough. She delighted in watching his ridiculous dress swirl back and forth as he worked. She loved seeing him scurrying around as fast as he could in his ridiculous pink high heels.
As soon as her couch was adequately protected, she ordered him to his knees right in front of it while she went to her desk drawer to retrieve her collection of rope. A few minutes later, she had him firmly bound in his usual uncomfortable position while she hurried back to her bedroom to retrieve one of her scarves. As soon as his eyes were securely covered once again and she was sure that he couldn’t see her, she began undressing – much quicker than usual. As she removed her panties, she unconsciously checked them for stains from her approaching period. Fortunately, there was nothing yet to for her to notice. She sat in front of him with her legs spread wide. She hesitated a moment as she realized that his dress might get messed up with what she was about to do, but the hesitation was only a moment. She was too ready for him to stop now. Besides, the dress was supposed to be washable.
She quickly reached out and roughly grabbed his lengthening hair with both hands. With a grunt, either from effort or more probably from excitement, she pulled him straight down into her waiting sex. Yes! Yes! Yes!
Chad had heard her moving around him as she undressed. He had been through this enough now that he pretty much knew what to expect. Still, he was surprised at how quickly and roughly she grabbed him and pulled him down onto her – so surprised that it momentarily scared him. But once he was settled in place, he went to work on her with is tongue. It would do no good to try to do otherwise, bound as he was, he couldn’t even try to do anything else.
She seemed to be extra sensitive tonight. More ready too. Her first orgasm came quickly and strongly. When it was over, he did his best to catch his breath before going back to giving her more pleasure. Having been sated once, she seemed less urgent, but no less ready. He moved his tongue slower, trying to slow the pace somewhat, and in doing so, thought he detected something a bit different… or did he? He wasn’t really sure. Did she… taste a bit different tonight? No, it was probably just his imagination – or something left over from what she had done to his pork chops tonight.
Mel’s first orgasm had come fast and strong. Now she was savoring the delicious feeling of what he was doing to her down there – wonderful! She could tell he was going slower than the first time, and actually appreciated it. Still, she hit a point where her excitement couldn’t go slower anymore, and despite his pace, she pulled him harder into her and rode him to a second high. Wonderful! Wonderful! Wonderful!
Chad felt her orgasm again. Would she be finished with him now? He hoped so. He got very little out of this… except discomfort, difficult breathing, a very tired tongue and mouth… oh yeah, and the satisfaction of having satisfied a woman – at least in some way – totally! Unfortunately, it wasn’t even close to being in any way that he really wanted to satisfy her.
He thought about the chastity device locked onto his most wanting part. She was making sure that he could never receive any pleasure to that most important part of him – at least for the terms of the bet. And afterwards? If she won? What could he expect? As his tongue started once again to pick up the pace within her, he thought not so much about her, but about himself, and what he might expect if he lost the bet – like she wanted him to. Yes, he did love the diapers and the dresses and even all the humiliation. But he didn’t really love being denied the very pleasure he wanted the most. It was something to think about.
Mel continued to writhe under the workings of his magic tongue. But as good as it felt, she was having more trouble reaching the high she wanted to get to – at least one more time. Was it that she had already had two huge orgasms now? Or was he doing anything different. She was so caught up in the pleasure she was feeling though that she couldn’t really tell. All she knew was that she wanted more! Just a bit more! She had to have it! Grabbing his hair even harder, she began grinding his face into her harder and harder as she moved back and forth and squirmed on the couch. His tongue seemed to go from what it had been doing to gyrating madly around inside of her. As if he could sense how desperate she was. Her high increased till she didn’t even know what she was doing anymore as she continued to grind his face into her and writhe around. And when she finally reached her high, it was mind-blowing! The peak lasted, and lasted, she pulled him harder and harder against her, riding him hard, trying to maintain the incredible feeling that she knew would fade all too quickly. And when it did finally fade… only then did she realize how hard she had been pulling on him.
She eased up and felt him try to grab some deep breaths of air. She pulled his head away from her slightly and watched as he gulped the air into his lungs, trying to recover. She took pity on him then and pushed him back till he could support himself on his knees once again, his body bent backwards since his arms were attached to his ankles by a very short piece of rope. She got up and laid him on his side, blindfold still in place. She grabbed one of the towels from the couch and used it to wipe his face clean – it was a mess! And… was there a hint of red mixed in with the fluids on his face? Ugh! It was getting closer to that time. She left him there like that to get herself cleaned up.
Chad didn’t care about moving that much. Yes, being free would be more than wonderful, but just then, he only wanted to recover. His face felt raw and hurt. His tongue was so tired he didn’t think he could talk if he wanted to. His breathing finally slowed down to normal. She had been even harder on him than usual tonight. And there had been an urgency in her like he’d never seen.
He thought again about his chastity device and his own sexual wants. For the first time in a long while, his trapped penis had tried to get hard again today. And it had hurt! Why now? But more importantly, he thought about the future. What could he expect if he somehow lost the bet – like she wanted him to? Would he ever feel sexual pleasure again? It was a discouraging line of thought.
Mel came back with her robe wrapped tightly around her. She untied his arms and ankles. She removed the blindfold that covered his eyes. “Come on,” she said, “let’s get you cleaned up.” She grabbed some of the towels from the couch and carried them into her bedroom where she laid them out on her bed to protect it. She had him grab some of the diapers he used on the floor during his punishments to go over top of them for even more protection. She looked at the dress he was still wearing, fortunately their activities in the living room hadn’t harmed it in any way. It was still fairly clean. “Take that dress off,” she told him. “It will only be in the way now.” As soon as Chad had removed his sissy baby dress, she tied him spread-eagled on top of her bed.
She looked down at him. Did he seem a bit more tired than usual? Or was it something else? Maybe he just needed a drink? She did need to keep him peeing. She went out to the kitchen and grabbed his latest baby bottle. There wasn’t much in it, but it would be enough. On the way back, she spotted his pacifier on an end table. She grabbed that too. Back in the room, she stuck the nipple of the bottle in his mouth, then propped the bottle up on some pillows so it would stay in place. It took a bit of arranging with the pillows, but it wasn’t too difficult. His head was forced to the side so he could keep the nipple in his mouth, but maybe that was a good thing. The bottle would also help to keep his mind on other things than what she would be doing with him.
She undid his soaking wet diaper, amazed that the thing hadn’t started leaking yet. Was he aware of how wet the thing was? Probably! It was a dumb thought! He was wearing the thing, how could he not know how wet it was? She didn’t pull it out from under him though, not yet. After watching Sandy changing him earlier, she realized that a little extra protection might be needed at a moment’s notice, and as wet as his diaper was, it would still help.
She stared at his penis, trapped inside of the clear chastity device. So small. Did he feel anything from it at all anymore? She wasn’t really sure how she felt about that one way or the other. She began removing the device. She saw his eyes try to glance down at what she was doing, but he had to keep his head turned to the side and away from her to keep nursing on the bottle. As soon as she had removed all of the pieces, she grabbed his tiny penis with her two fingers. So small. So soft. She wiggled it a bit and saw his eyes trying to look again. Too bad! She wiggled it some more and watched it carefully. No reaction – perfect! She picked up all the pieces of the chastity device and pulled his soggy diaper back over him – just in case. She took the device out to the kitchen to clean it thoroughly.
Chad sighed. He had felt her removing his device. He had felt her touching him, moving him around. But it hadn’t been enough to grant him any pleasure. And he wanted that pleasure. He thought again about the future. If he won, then there would be no problem. He could have all the sexual release he wanted. He could also have the pool table and all the other stuff that Sandy had put into her drawing for his apartment. Of course he would also have to go back into hiding with all the precious things that he had come to love. In fact, he might never be able to wear his diapers again – maybe not even in private. His dresses and heels the same way. What if someone caught him? They would know in an instant that everything he was going through now was all because he had wanted to do it, not because of the bet.
But if he lost the bet… if he lost… if he lost… He would probably be stuck wearing diapers for the rest of his life. Did he want that? Maybe… maybe not. He did love wearing them – at least right now. He might be stuck wearing dresses and heels the same way. And yes, he did love them too. But would he ever get any sexual release? Unknown! He could only hope.
The bottom line? It was a toss-up. Equal arguments for both sides. But maybe, maybe, at least right now, he felt more of a tug for wanting to win the bet. Yes, he had to win. After all, there was still something to be said for self-respect. Still something to be said about being able to walk down the street and hold your head up high. Yes, he had to win. And he still felt completely confident that he would win – no matter what Mel did to him. The only problem was, he knew he was losing his control – at least for short periods of time. In that respect, she was definitely making progress on him. But he knew his body. He knew that he would recover all his control – very quickly. At least, he hoped he would.
Mel came back with all the freshly cleaned plastic pieces to his chastity device. She checked the contents of his bottle as she walked up to the side of the bed. Still a tiny bit left, but not much. She grabbed a razor and quickly removed any of the few stray hairs that were popping up. Then she coated him liberally with lotion to protect his skin and began fitting the pieces onto him once again. She saw him purposely look away through the entire process. She wondered how he really felt as she held his tiny penis in her fingers and threaded it into the hard plastic container, out of his reach, impossible for him to touch, denying him the ability to feel – anything. No wonder he was looking away. She didn’t blame him one bit. She noticed the tiniest bit of a shudder go through him as she clicked the lock shut. Finished!
With the chastity device in place, she went back to her bathroom where she kept a supply of cloth diapers for him. She grabbed a stack of the thickest ones along with a pair of plastic panties and some large diaper pins. Bringing them back to him, she finally pulled his soaking diaper out from under him. She wiped him off top and bottom and slid the fresh diapers under him.
She reached into her night table and brought out the jar of suppositories and pulled one out. She noticed his bottle was finished and took it from him, in the process, letting him see the dastardly little bomb in her hand. He looked away again and she almost laughed. Again, she couldn’t blame him. His pacifier caught her eye and since she had removed the bottle, she stuck that between his lips instead and watched him begin to nurse on it. Just like a baby – a big baby. She untied his legs and raised them up high so she could shove the suppository up inside him. According to the notes on her calendar, this would be the last time he would be getting two in one day – not that he would ever know it.
She lowered his legs, and as she lowered them, he began peeing again. Quickly, she grabbed one of the fresh diapers she was about to put on him and pulled it over him to catch any mess. He was still looking away. No recognition that he had even peed at all. Did he know? He had to know! Silly question! Yet the very fact that she had seen him do it made her feel like she was making progress with him.
She pulled all the super thick diapers up between his legs, and with a lot of struggling, pinned them in place. His legs were forced wide apart by all the material bunched up there. She pulled his plastic panties onto him too.
Finally, he was looking at her again. She looked down at him. Here he was, this so-called man… this so-called big powerful man – reduced to a diaper wearing, pacifier sucking baby! And it had been she who had done it to him. She was the one totally in control. She was the master – or mistress, not him! He was reduced to being – pathetic, all because of her. Her rules! Her whims! She – the supreme woman!
And all her thoughts about him started to make her sexually hungry again. She had already had three orgasms, wasn’t that enough? Obviously not! The more she looked at him, and thought about what she had done to him… and some of the things she had yet to do to him, the more hungry for sex she got. She had to have him again! Had to! But she didn’t want him the same way she did before, not in the living room, on his knees, with his talented tongue in her crotch. But how?
She thought about all her toys in the nightstand. She opened the drawer to look through them. The strap-on caught her eye again. But no, she had just diapered him. And after all the trouble she had just gone through to get the pins in place, she wasn’t about to undo any of that! She was about to select one of the other toys that had interested her before, but her eyes kept going back to the big strap-on. Besides, the other toys were more for… solo use. She wanted to feel him inside of her. But she couldn’t feel him inside of her, not with the chastity device locked onto him – and she absolutely wasn’t going to undo that!
On a whim, she pulled out the strap on. The device had two ends, one big one for him, and a smaller one that would go up inside of her. Supposedly, she could get pleasure out of the thing while she reamed him with it. But the big end of the thing kept drawing her attention – more and more. She suddenly wanted to know what it would be like to feel that big thing up inside of her. The smaller end, the end made for her, looked puny in comparison. But how should she go about doing it?
She was tempted to just shove the big part up inside of her, maybe after Sissy had gone home, but that idea didn’t really resonate. Then she got another idea, she could put the device on him! Strap him into it! She could still get all the pleasure, but he would feel nothing but her weight as she rode on top of him. She stopped. But would it be too much of a masculine act? She didn’t want him to experience anything masculine – if she could help it. But he was tied up. He would experience – almost nothing! And… she was starting to wan this more and more!
Not caring anymore, she unfastened the small end of the device and removed it. Then she began bringing it up his legs and over his super bulky diapers. The fit over the diapers was very difficult, but she finally managed it – even with his arms still tied to the top of the bed. The device was now sticking straight up, right where it should be. It was ready for – her! She was about to rip off her robe when she saw his eyes, hungrily looking at her. No! No! No! That would never do! She grabbed the same scarf she had used to blindfold him earlier and once again wrapped it around his head, completely cutting off his vision. Only then did she remove her robe and climb up on the bed.
The strap on penis looked huge – and so interesting! She straddled his body, and slowly… slowly… slowly lowered herself down. She was still a bit moist from earlier which helped. And eventually, she settled the thing all the way up inside of her. Mmmmm! She rocked back and forth, then stopped and looked at his blindfolded face. The pacifier was still stuck in his mouth. She laughed out loud. Even in the middle of sex, she had reduced him to a pacifier sucking, diaper wearing baby – who could not get any pleasure at all from the adult act of sex. And she was the one who had done it to him. She began riding the strap on up and down. She was the one who had reduced him to the status of a baby. The pleasure grew so fast, so hard. She was the one who had removed masculine trait after masculine trait. She pumped harder, faster, her excitement growing by leaps and bounds. She was the one who had done it all to him, denied him all his sexual pleasure, denied him all his masculine traits, denied him the ability to be – a man! And she climaxed like she had never climaxed before, screaming at the strain of it, digging her nails into his side to hold onto him. Riding the wave of pleasure for all it was worth! And as she came down from her high, as the wave of orgasm receded, she opened her eyes again and saw his face – his blindfolded face with the pacifier stuck in his mouth. She could read nothing from it. But then, she knew he had felt – nothing.
Did she feel sorry for him? Not really. But still mounted on the huge dildo of the strap-on, she leaned forward and laid her body down on top of his. Her breasts rubbed under his bra that held his own “glued-on” breasts. Despite his bra, she rubbed her bare breasts up and down on top of his fake ones, as if she were trying to bring him some measure of pleasure from the act. But of course, she couldn’t. He could feel nothing.
Still mounted on the strap-on, she hugged him to her, holding him as tightly as she could. He was her creation. Hers alone! She lowered her head to rest on his chest… and the words just kind of came out, soft, but still audible. “So precious! My baby!”