The Bet - Chapter 45 (Monday – week 7 Part 7 of 7)

The Bet
by Karen Singer

Chapter 45 (Monday – week 7 Part 7 of 7)

Instead of having him practice his ballet, Mel had him keep busy with cleaning the apartment instead. But every few minutes she called him back to practice his little apology for Robin again. She enjoyed watching him, she just wished she could be there to see it in person.
But finally, watching him curtsey for her over and over again had enough of an effect on her. She got up from her seat in the living room. “Strip down to your diaper and nothing else!” she ordered as she headed for her bedroom. Chad did just that, but not before curtseying one more time, even though she was walking away from him. It was better to be safe than sorry!
It took him only a few minutes to get himself down to just his diaper. Removing his bra left his glued on breast forms hanging from his chest with no support. They felt all too awkward and heavy that way as they pulled against the skin of his chest. Removing his waist cincher though was perhaps his biggest relief. The darn thing was all too tight and confining. He had a vague idea of what would be happening next, but knowing Mel, he dared not make too many assumptions.
She was gone a while, but eventually, she called him into her bedroom. When he got there, she was holding one of her scarves in her hand. Out of the corner of his eye, he noticed some ropes attached to her bed, but they were mostly pushed out of the way. The minute she approached him with the scarf, his assumptions became confirmed. He curtseyed to her – just because he dared not do it.
“I’m going to put this on you again,” she said, “and I’m not going to tie you up… yet.”
That surprised Chad a bit. He had already seen the ropes attached to her bed. But then she did say… “yet.”
“But so help me. If you even do anything to take this off – or if it somehow even falls off, then I’ll make sure you’ll regret it for a very, very long time!”
The way she had said it left him in no doubt, and his thoughts instantly went back to the beating she had given him earlier. His backside still burned terribly. He curtseyed. “Yes Mistress.” What else was he going to say? That he was going to do everything he could to get a look at her gorgeous naked body? He knew better! It wasn’t going to happen! Never once in their relationship had he been allowed to see her naked. He had only been allowed to touch her. But just touching her was reward in itself. She felt so… beautiful! A moment later his sight was totally cut off as Mel tied the scarf tightly around his head – then she pulled on it again, making sure it was extra tight and secure.
Finally feeling satisfied that he couldn’t see her, Mel began undressing. She still didn’t understand her strange aversion to him seeing her naked, but after all this time, it was just something that she accepted. She climbed up on the bed. “Make love to me,” she told him. It was Sissy standing there wearing nothing but a diaper, his breast forms hanging oddly from his chest – but it was Ray she was trying to picture in her mind. Ray, who had driven her wild in the movie last night. Ray, who she would be going out with tomorrow night. Sissy would be nothing more than a warm up before Ray. Something to take some of the edge off of her… anticipation.
Chad groped his way toward the bed, then up onto it. He felt for her body and his hand connected with her naked breast. Surprised, he kept it there as he brought his body over to lay close to her. The skin on her breast felt so soft, so smooth. He moved his hand over it, lightly flicking the nipple with the tip of his finger. He allowed his hand to roam further, feeling more of her. She felt… wonderful! Unable to help himself, he got to his knees next to her so he could feel her whole body with both hands. He allowed his hands to roam in opposite directions, sliding ever so tenderly over her ever so smooth skin. He heard her moan and felt her writhe slightly. The feeling of her was exquisite! And he was only using his hands! Having his sight blocked off allowed him to truly feel how wonderful she felt. It allowed him to concentrate harder on the things that were really important. He allowed both hands to probe, and squeeze, and caress, drawing as much pleasure from it as she did. The only thing was, that sexually, he was completely denied any reaction. All he received sexually was frustration. But he was so very glad that she was enjoying the full benefit of his touch.
Mel writhed and whimpered softly as his magic hands worked their way over her entire body. There was just something so sensual about his touch. Several times his one hand found her ever moistening sex and lingered there for a moment, but it was only a moment, leaving her hungry for more. The fingers of one hand seemed to grab her breast a bit firmer just before she realized he was lowering his head toward it. She was struck but the odd sensation of his breast forms, both of them, rubbing firmly against her other breast, stimulating it. But that was only a side sensation. She was more interested in watching as the hand on her other breast guided his mouth directly to her nipple. He sucked on it for a moment, like a baby? Then his mouth pulled away slightly and she felt his tongue flicking lightly over the tip of it. Her breathing quickened – especially when his other hand found her dripping sex again – and stayed there. She arched her back as his fingers began probing deeper – deeper but still lightly. As if teasing her. Making her want more… more… more! Moments later, she was rocked by her first orgasm. Exquisite!
Chad let her come down slowly from her orgasm. But before he could do anything else, he felt her hands grabbing his hair, pushing his head down between her legs. He resisted, but only to the point where he could move his body, climbing over her carefully to position himself better. But her hands never quit their grip in his hair, and as he dove down with his tongue into her, he felt her pulling his head harder and harder into her. He couldn’t see them, but he felt her legs writhing over his body on both sides, one of them moving up and down his back. Her second orgasm came fast and much stronger than the first.
Mel’s blurred vision stared at the ceiling, but she had no interest in seeing anything. All she was interested in was how good Chad’s talented tongue felt as it still worked away at her. She felt momentarily spent after her orgasm, but that didn’t matter. All that mattered was how delicious Sissy felt as he continued to stimulate her so wonderfully. He was going slower now and she let up a bit on her grip. She hadn’t realized she was pulling on his head so hard. She allowed herself t take a deep breath and close her eyes, the better to enjoy everything she was feeling. Heaven! And slowly, ever so slowly now, she felt her next orgasm building again. The only thoughts capable of getting through to her now were the feelings that she felt throughout her entire body.
Chad kept at her till eventually she had one more orgasm. He had gone slower that time, much slower. As she came down again, he was aware of her breathing slowing down, her legs on each side of him calming, her entire body seeming to relax. He felt her pulling on his hair again, but it was in a different direction, pulling him away from her. He pulled his head away, and climbed off of her, once again laying next to her. He put his arm over her and held her as she continued to relax more and more. Such a pleasure. He couldn’t help but wonder though at what it was that she felt. Women were capable of having orgasm after orgasm, while he was capable of… nothing. But that didn’t mean that he didn’t enjoy making her feel good. Worshiping her body by just touching her. He felt… honored that he was capable of giving her the pleasure that he could. He might not be any good in the ways that most men were, but at least he could do this much for her.
He felt her moving, rolling over on top of him. The weight on his breast forms was crushing, but he didn’t care. He felt her head come down next to his and he felt her lightly kiss his neck over and over again. If he had been any kind of a man, he knew that his useless penis would have responded quickly. But… he wasn’t that kind of a man. Not anymore. Not since she had locked away all of his main source of pleasure.
He felt her moving off of him again to his other side, kneeling next to him, just as he had been kneeling next to her a little while ago. Something tugged lightly at one of the breast forms glued to his chest, and he realized she was rubbing her hand lightly over it, just as he had done for her.
“Do you feel that?” she whispered. “Does that feel as good for you as it does for me?”
How could he tell her that all he really felt was the light pulling and pushing as the breast form tried to move under her hand. But he said nothing at all. He felt her hair tickling his chest, and realized she was kissing what would have been his breasts if he were a real woman. It was an odd sensation, totally useless in its intent, yet oddly stimulating never the less.
He felt her pull her head away from him again. “Scootch over a bit, this way,” she said as she moved back, and finally off of the bed. She pulled on his arm till he was laying on the very edge of the bed. “Stay there. I’ll be right back… And don’t fall off!”
He heard her leave. She was gone a short while. Then he heard her back again and doing… something. Something that involved the bed. He could feel her on the other side of it, doing… something. Then she was back again, right at his side. He felt her grab his arm with one hand while her other hand touched his body.
“Roll over to the other side now,” she instructed as she pushed lightly to guide him.
Chad rolled over onto his stomach and started moving his body sideways toward the other side of the bed. He quickly discovered that what he had felt her doing was protecting her bed. His hands encountered multiple thicknesses of diapers under his entire body.
“Okay,” she said as he reached the spot she wanted him to be in. He stopped and started to roll over onto his back again. “No,” she told him. “Stay face down.” But the position wasn’t quite what she wanted. “Up on your hands and knees,” she ordered.
Chad did as instructed, but now he was getting confused. On his hands and knees? He felt her hand on his back again as she told him to move forward a bit toward the head of the bed. He crawled forward slightly, then more, till she told him to stop. A moment later, she was pulling open his soaking wet diaper and removing it. The air felt cool and odd as it caressed the parts of him that were forever packaged inside of the warm diapers. A moment later he realized he was involuntarily peeing as the cool air stimulated him. He heard Mel laughing as she stood by and watched. As used to it as he already was, he felt embarrassed by his lack of control.
He felt her moving up towards his head more, and a second later he felt her tying the rope to his wrist on that side. She moved back and fastened his ankle next. Then she moved around to the other side of the bed and bound that side of him. He had to wonder why. He certainly wasn’t planning on going anywhere. And bound like he was he could still stretch out and lay down easily. But… it was her game.
He could hear her moving around near him, but he couldn’t tell what she was doing. Not till he felt the cold shock of her hands full of lotion suddenly rubbing all over his still hurting backside. But this time the hurt died quickly and was replaced by more and more pleasure, especially as she purposely moved closer and closer to his waiting back hole.
Mel let her finger slip slightly inside of him, and saw the immediate reaction as his whole body stiffened. He loved this. Well, tonight she wasn’t going to disappoint him. She played with him there for a minute, moving her finger in and out of him – as much to spread the lubricant as for his enjoyment. Then she pulled her hand away again.
On her nightstand, she had already selected one of the colorful dildos to use on him. The one with all the swirled ridges along its length. She picked it up and placed it against his asshole. His sudden intake of breath was obvious. So was the stiffening in his entire body again. She held the toy there for a moment, but she couldn’t keep it there long as he started pushing back toward it, wanting it, almost more like needing it. She let him have it, but only a little at a time. But the further it went into him, the harder it was to grip the toy, especially since the swirled ridges on it were acting like screw threads and the whole thing kept trying to turn around in her hand. She held on tighter though and he soon loosened up so that it wasn’t as much of a problem.
It seemed like no time till he was pushing and pulling like crazy against the toy in her hand. He seemed… desperate in some way. And she supposed she understood that – seeing as how she had completely denied him any chance of an orgasm. She was simply amazed at how desperate he seemed to be, pumping himself, screwing himself, fucking himself against the toy in her hand. But before long, she saw him shake his head again and he slowed down further and further. With the toy still buried half in his backside, he finally moved his hands forward and slumped down on his elbows in defeat.
She was disappointed that he didn’t try longer. But she understood that. Maybe… maybe he would enjoy a different toy? She opened her drawer and began sorting through all the different options available to her. Colorful options and… oh… Her eyes fell on the strap-on dildo she bought to use on him… but had wound up strapping to him and using it on herself instead. The thing had a small side that was supposed to stimulate her too. Would it work? Only one way to find out.
She pulled it out of the drawer, found the smaller end and fastened it to the back of the device. Then she set about fastening it to her. It was an odd process and it felt odd around her hips. It especially felt odd from the part that was buried inside of her. But now that it was there, she was starting to get sexually stimulated again. The odd fake penis stuck out in front of her strangely. As she moved around, it accidentally bumped against the side of the bed, stimulating the inside extension in the process. She found that very interesting!
He was still slumped down on his elbows. She didn’t want that now. “Get up again,” she ordered and waited till he had once again gotten to his hands and knees. But she didn’t want him to slump down again. She found two more lengths of rope, but before she used it, she grabbed one of his wrists and pulled it out to the side, pulling it against the rope holding it to the headboard, until she could place his hand on top of the phallic piece sticking crudely out from her groin. “Feel that?” she said. “That’s for you!” She wanted him to know what was about to be done to him. She wanted him to know that he was about to get screwed – like a woman!
She grabbed the rope then and tied his wrists to his knees on both sides. Now he couldn’t move his hands or his legs forward or back. He would be stuck in the position he was in. Perfect. Just the way she wanted him.
She climbed back up on the bed behind him, but the fake penis sticking out from her was harder to deal with than she thought. She had to maneuver around just to get it close to his asshole and she kept bumping and scraping it against him in the process. How did men manage to do anything with these things? And then it was even harder to get it exactly right and control how she wanted to push it into him. She had to use her hands to guide it into place and hold onto it. Then she pushed lightly with her hips till it finally slipped partially inside of him. Only then did she release her hands and grab the sides of his body instead. She could feel the pressure from the little piece inside of herself, but concentrating on it as well as what she was trying to do to him was difficult. Slowly and carefully, she pushed the fake penis attached to her inside of him.
Chad was a bit scared. Yes, he loved having her play with his asshole. Yes, he loved all her toys. But this… this seemed different. And once the damn thing was inside of him, it felt bigger, fatter than any of her other toys. He felt her pushing it slowly into him, further and further, more and more. He was just glad he was already so loosened up from her previous toy. And then he felt her pulling away again, pulling away with her body. And the toy that was in him was obviously moving with her body. It was such a strange sensation. Several more times he felt her pushing slowly into him all the way, then pulling back again, almost all the way but never quite removing the crazy thing.
Mel thought she had the hang of it now. It wasn’t really so hard at all – once she had gotten it into him. And yes, she did feel something from the little piece inside of her – and it really felt pretty good. Certainly not like anything real, but it was… interesting. Somewhat stimulating too. As she moved slowly back and forth, she could see him relaxing more and more, getting into it more and more. She leaned over him now, the new position made it harder to pump against him, but she kept going anyway as best she could. She reached under his chest and began fondling one of his breast forms. “Do you like this?” she asked. “Can you feel me playing with your tits the way that you play with mine?” She almost giggled. She was fairly sure he couldn’t feel much from his fake breasts at all – but you never know. “Does this make you feel more like a woman now? A real woman?”
Something about her words hit a nerve inside of Chad. He shuddered involuntarily at the thought and clamped down a bit harder on the phallic device inside of him as he began trying to actively pump back and forth against her – increasing the pace a bit.
Mel noticed his reaction, especially when he began speeding things up. She figured she must have said something that interested him. She almost giggled. She had wanted to imagine it was Ray making love to her earlier, but once he had started, she could only think of Sissy instead. So maybe… She leaned close to his head again and whispered. “Can you imagine that I’m Derek, and this is what Derek would be doing to you?”
Derek? Derek making love to him – like he was a real woman? Derek fucking him – like a real woman? But the feeling of the fake penis being pumped in and out of him made that scenario all too real and easy to imagine. He involuntarily felt his body tighten as that thought increased his sexual energy.
Mel noticed the change once again – and continued. “Can you remember Derek holding your hand in the movie? Dancing with you in the restaurant? Did you feel like a real girl then?”
Her words were having a profound effect on him, and he couldn’t help it. As much as he didn’t want to respond to them, he just couldn’t help himself.
“How did it feel to have Derek hold you in his strong arms as you were dancing? How did it feel when he hugged you so tightly when he said goodnight?”
Chad had no control of it anymore. He was pumping harder and harder, trying to feel more and more from the fake cock inside of him. He was being held and taken from behind by a living human body, and her words were sending images and feelings to his brain that he didn’t want to deal with in normal life. He was getting lost in her words and ideas and in all the many sensations. And it was building bigger and bigger, taking him further and further. Leading him towards…
“How did it feel when he pressed his lips up against yours and kissed you like he did?”
He could once again feel Derek’s soft lips pressing against his own, kissing him passionately. Derek’s strong arms were around him holding him tightly. He could again taste the thick lipstick on his own lips. He was helpless in Derek’s arms. Soft lips kissing his own. A man’s lips kissing his lips – like a woman…”
The strong almost cramping feeling may have begun at the base of his spine, but it quickly spread up and down throughout his entire body, from his toes to his fingertips. Even though Mel was still pumping in and out of him, he couldn’t move as all his muscles locked up tightly – then they suddenly started shaking – all of them! It felt like his whole body was straining in every direction at once. And the yell that finally escaped his throat was strained and high-pitched – and seemed to go on, and on, and on.
Mel was frightened at first, but soon her fright became amazement as she realized he was actually orgasming. She did her best to lean over and see just how bad his chastity device must be hurting him, but from everything she could tell, his trapped penis inside was just as tiny as ever – but there was liquid pouring out continuously from the device – and she could tell it wasn’t pee! Incredible! Incredible! Incredible! In many ways, she had just made him cum – as if he were a woman! A female! It was like stripping yet another layer of masculinity away from him. And as his own shaking started to come to an end, the added realization of what she had just done to him sent her over the edge one more time herself, except that this time, she was the one buried inside of him. She had no option but to pump harder in and out of him as she rode her own orgasm to its conclusion – which only caused him to keep pumping desperately in response.
It was a few moments before either of them could slow down – let alone settle down. It was an experience that Mel figured she’d never forget. She still didn’t believe it had just happened. Breathlessly, she slowly and carefully pulled her attached phallus out of him. She had taken him like a man – and he had responded like a woman!
Chad didn’t know what to think. He had finally had an orgasm… he thought. Although in truth he had never really felt anything like it – ever! Was it possible? He hadn’t thought so before, but now… Images of Derek kissing his lips again still swirled though his mind. He couldn’t stop them. He wasn’t even sure he wanted them to stop. Mel climbing off the bed distracted him enough to finally erase them from his mind – mostly.
Mel got down off the bed. She would have untied him, but she wanted to remove the crazy strap on device first and put something on to cover herself. As she was just starting to unbuckle the device, she heard a faint splashing sound. She looked over at him and saw a strong stream of pee rushing out of him again, splashing straight down onto the diapers protecting the bed below him. It puddled there a bit before starting to sink into the absorbent material. She smiled at the sight of it. In so many ways, it was hard to believe that he still had any control. Twice tonight she had seen signs that made her feel like she was winning this bet, but she knew better than to trust everything she saw. How long had he managed to hold back at work today? She had no way of knowing.
Chad felt so embarrassed as he realized he was peeing uncontrollably again. Actually, after what he had just experienced, peeing had been the furthest thing from his mind. Had he actually orgasmed? He was pretty sure. Yet the way it had happened – while feeling really great, had also been very embarrassing. What had happened to him? No, what was happening to him? Because the changes still seemed to be happening. But there was one other thought that seemed to lock onto his mind that he couldn’t shake – what he had once thought of as impossible, had just happened. It was possible! He had thought he could never orgasm that way, but he just had! But as his peeing came to an end, that thought led to one other thought – a very troubling thought. If the impossible was now possible, how about with their bet? He had thought before that Mel making him totally incontinent in only two months was completely impossible. But now? He still believed it couldn’t happen. Not at all. But… but now there was a tiny seed of doubt.
With her robe fastened tightly around her, Mel removed the ropes that held him in place. Then, while he was still on his hands and knees, she removed the scarf she had used as a blindfold on him. For no other reason than to be nice, she pulled away the wet diapers that were under him. “Roll over on your back,” she told him. “Let’s get you diapered again before you pee all over everything.”
Chad rolled gratefully to onto his back. He felt a mixture of pleasure, fatigue, and embarrassment. A moment later he felt a wave of frustration as Mel took out a jar of suppositories and shook it in front of him. “We can’t forget these,” she teased. She opened the jar and pulled one out. Chad turned his head away in disgust the moment he saw the capsule shaped pill. What Chad didn’t see though was Mel letting the suppository slip back into the jar as she put the lid back on. “Okay, raise up,” she ordered. Chad pulled his legs up high, exposing his bottom for her again. Mel stuck her finger way up inside of him – as if she were really sticking the pill up there. Once again, Chad never knew. But this was the second time today that his suppository had been faked. Her plan called for him to gradually get less and less as time went on now. But her big question was, would it make a difference? She could only pray that it wouldn’t. Just as she didn’t really know what kind of control he had over his peeing, there was no real way she could tell what would happen once she stopped the suppositories completely. And there wasn’t a lot of time left in this bet!
A short while later, clad in only the over-stuffed padding of four disposable diapers. Chad curtseyed one last time for her and gathered his things and took them home. Once again, Mel stared at the back of her closed apartment door after he left. Time was running out. Things always seemed to come down to time – precious time. Would she make it? Would she really do the things she bet him she could do? It had been a crazy bet from the start. A really stupid bet. She blamed it on too much beer that day. But the truth was, there was something else. Something else inside of her that must have realized she wanted to do this… maybe, needed to do this. But still, would she make it? She had to. She just had to! She couldn’t dare lose him. She didn’t want to contemplate what it would be like without him.

“Goodnight Sissy,” she whispered again. “Goodnight.”