The Bet - Chapter 35 (Friday – week 5 Part 8 of 8)

The Bet
by Karen Singer

Chapter 35 (Friday – week 5 Part 8 of 8)

While Chad was picking up the diapers he had spread all over the floor, Mel wandered into the kitchen and picked up the child’s menu that she had made him color in at the restaurant. As she turned the pages, looking at the pictures, she was pleased with how juvenile looking they were. But she wasn’t surprised. As they had talked in the restaurant, she had watched him growing ever more cross-eyed as he tried to peer past the bottle he was holding up and drinking from – while he colored in the book. Trying to do such a thing would have made her dizzy for sure. But then, she would never put herself in a position to do anything even remotely like that. She made a mental note of a few of the pictures that she thought Sandy might get a kick out of.
As she stared at the pictures, her mind wandered back to their earlier dinner conversation. She still had no idea what she wanted to do with him at the poker game, but he had given her lots of interesting things to think about. And the more she thought about some of them, the more sexually stimulated she seemed to become. Imagine, making him behave like a total ass in front of all his friends – his male friends!
But the truth of it was, that she really had no intention of making him behave like that – yet. She didn’t think it was right to disgrace an obviously cherished event with things that didn’t belong there… Although the more she thought about it, the more interesting some of the ideas became. In her mind’s eye, she could just see him skipping into the room full of men, wearing that silly babyish outfit, his diapers showing obviously underneath. Maybe she’d add a baby bonnet to his head to complete the picture. His pacifier would be another good thing too – he could suck on it in front of them all evening… And speaking of sucking on something…
She closed the book and hurried out into the living room. He had already put the excess diapers away – no matter. While he was sorting through the laundry, she hurried into her bathroom and started pulling out towels. Moving faster and faster, she carried them back out into her living room and began spreading them all over her couch, layering them to protect the chair as much as possible.
She moved on to her desk drawer where she pulled out a jumble of ropes. Quickly selecting one, she carried it over to where he was bent over the laundry basket. He started to stand and turn around at her approach, but she stayed behind him and pushed him back down again. Grabbing his elbows from behind, she pulled them behind his back, pulling hard to bring them as close together as possible. She quickly wrapped her piece of rope around them, binding his elbows behind him. She grabbed the rope and pulled him to his feet, then kept pulling, forcing him to walk backwards as she dragged him toward her couch. She put him into position facing the couch, then forced him to his knees. She grabbed more rope. His wrists were soon bound tightly together, then his ankles. Another rope soon ran from his wrists down to his ankles, pulled tight so that his arms, even bound at the elbows, were stretched as far out as they would go. Feeling satisfied with her work so far, she hurried straight into her bedroom.
Chad had been very startled when she had suddenly come up behind him. Then even more so when she had roughly grabbed his elbows and pulled them back. She hadn’t bound his elbows like that behind him before and it hurt from the beginning – it still hurt now. The rest was more familiar. As he knelt before her couch, towels spread all over it, he knew exactly what to expect. Two minutes later, he heard her come back again, and faster than he expected, his sight was taken away as she tightly tied her scarf around his head.
Mel was breathing heavier now as she looked at him. He was ready. The couch was ready. All that remained was for her to remove her clothes. She still didn’t know why she didn’t want him to see her naked, but with the scarf covering his eyes, that wasn’t really a factor.
She walked around and stood in front of him, the crotch of her shorts pressed lightly up against his nose. She hooked her thumbs inside of the waistband of her shorts and wiggled her hips against his face, tantalizing him. Then very slowly, she kept wiggling back and forth as she lowered her shorts all the way to the floor. As she bent down, she allowed her body to rub against his face, till now his face was between her breasts underneath her shirt. She wiggled them back and forth against him before she stood up again.
She leaned into him again, letting her panties rub against his face. Letting him smell the scent of her sex barely masked underneath. Standing there like that, she pulled her top off, the motion causing her panties to rub against him once more. She stopped there like that and looked down at him, her pink pastel panties shoved into his face. She was getting so hot!
And then she felt it. Something unexpected. And her entire body shuddered. He had tried to stick his tongue into her, through her panties. She couldn’t have moved if she tried, hoping that he might do it again. And then he did! A moan escaped her lips as she reached down with both hands and locked them into his hair. Again his tongue reached out, harder than before… longer than before, she felt his head tilting as he licked the front of her with his tongue. Her back arched. She would have cried out loudly if her breathing hadn’t been completely locked up. By the time he tilted his head down again, she was panting hard. She reached back and removed her bra, freeing her breasts so they too could receive some attention.
She stooped straight down, rubbing her smooth breasts across his damp face – wet from the dampness that had come through from her soaked panties. With her hands still locked in his hair, she rubbed her breasts back and forth… round and round, all over his face – her nipples growing bigger and bigger as she did it. So good! But she needed more!
She stood up again, her panties once again pressed against his face. She felt his tongue reach out again even as she put her thumbs into the waistband of her panties to begin pulling them down. She had to pause till he withdrew his tongue again. Then just as she had done with her shorts, she rubbed her crotch against his face as she slowly lowered her panties. Down… down… till his face now touch nothing but her wet, naked sex. She rubbed it into him for a moment, then resumed her motion to bring her panties down to the floor, once again pressing her breasts against his face.
Slowly, she stood back up, never once letting her body leave his face, till her aching sex was once again poised right where she needed it to be. She ground it into him, spreading the wetness all over. Finally ending up again right where she wanted to press against him the most. She paused again, and once more she felt his tongue reaching out, only now there were no panties in the way. Now it could enter her further.
Again and again she thrilled as he licked at her, driving his tongue into her as far as it could go. But she knew it could go further… she needed it to go further. Still holding tightly to his hair, she quickly moved backwards, sitting down on the couch, dragging him down so that his feet, tied to his hands behind him, were lifted off of the ground and his weight rested on his face – mashed perfectly into her crotch.
She pulled tighter on his hair, pulling him harder into her waiting sex, and was rewarded to feel his tongue once again reaching out, this time seeming to probe her everywhere it could reach. Spot after wonder spot inside of her was touched by his tongue, the very movement of it driving her wild. And then it finally found the sweetest spot of all and lingered against it, flicked against it, licked against it… over and over again… driving her up, higher and higher, wilder and wilder, till at last… “Yeeeesss!” she screamed in ecstasy.
She felt his probing tongue slow as she finally came down from her high. Slower and slower, till she felt it withdraw completely. She wanted more though. She was nowhere near being finished. But before she could urge him to do it again, she felt his tongue reaching out once again, this time almost tentatively. Teasing her. Sending her in an altogether different direction. No longer thinking, she abandoned herself to his talented tongue, riding him once again to yet another wonderful high.
This time, when she came down, she felt his tongue withdraw once again. She realized he was breathing hard, almost gasping for breath. She took pity on him and pulled his face away from her crotch so he could breathe better. His face was a total mess, but she didn’t care. But the act of pulling him away and looking at him, seemed to ruin the magic. She no longer felt the desperate need she had felt earlier. Her hands still locked in his hair, she tilted him back till his feet returned to the floor. Then she slid down from the couch right in front of him. She pulled his messy face into her neck and hugged him, pulling his body as closely into hers as she could. She held him like that till they both calmed down. Then, slowly, she released her grip on him and leaned back. He was a mess! An absolute mess! And it had been wonderful – yet again!
As messy as his face was, she leaned in close and lightly kissed the bare patch of skin on his forehead just above the blindfold. She knew the moment she had done it that she shouldn’t have, but it was too late now. She moved around to his side, and gently pulled on him, helping him to lay down where he could be more comfortable. As soon as she felt satisfied with his position, she stood up and left him, going straight to her bathroom… and into her shower.
Chad laid in darkness, unable to see because of the scarf tied around his head… unable to move because of the ropes tied to his arms and legs. His arms ached terribly because of the way she had bound his elbows. But there was nothing he could do about it… unfortunately. The moment he heard her shower running he almost died, because it meant that she wouldn’t be coming back to release him anytime soon.
He waited, and waited – impatiently, yet unable to move in any way. He remembered that he was supposed to be making his diaper leak – again. Yet she had prevented him from drinking enough to keep working on it. Would she take pity on him and not punish him for failing? Somehow, he doubted it. She would be as ruthless as ever. Yet… he had felt the faint touch of her kiss on his forehead. It would be a moment he would always remember because it had surprised him so much. But was it worth her beating him again because he failed to make his diaper leak? He wasn’t so sure.
Mel wrapped her robe tightly around her naked body, tying it tightly to make sure it couldn’t slip open. Barefooted, she walked back out to the living room where he was still tied in the position she had left him. She knelt down next to him and removed his scarf. His face was still a mess. She reached over and pulled the top towel off of her couch and used it to wipe his face somewhat. He looked a bit better. Then she removed the rope binding his wrists to his ankles. His sigh of relief was audible as he bent his legs out straight. His elbows came next. He moaned with relief the moment they were free. Then finally his wrists. He struggled to pull his arms in front of him, rubbing them with his hands, flexing them over and over again to get them working.
She stood up again and looked down at him on the floor. “I suggest you get a bottle back into your mouth again and start drinking. Time is wasting!”
As Mel walked off to her bedroom, Chad slowly pulled himself up to his knees, and finally to his feet. His body still hadn’t recovered from the way she had used him, but he made his way back to the laundry basket where he had left his latest bottle and put it immediately to his mouth. But continuing on with the laundry was beyond him just then. He sat down on the floor, leaned his back against the washer, and just sat there, his eyes closed as he drank from the bottle. Had she really kissed him? Something about the tone of her last statement before she walked off made him seriously doubt it. But it was a nice dream.

Mel checked the clock more and more often as his deadline drew nearer. She knew he was drinking his bottles furiously to try to keep wetting, and she knew his diaper was indeed getting wetter and wetter. But she also knew that he wasn’t doing much of anything else. For once, she didn’t really care. With all her might, she silently wished him success. She didn’t want to beat him again tonight – especially when it was her fault if he failed. But she couldn’t relent in any way… or at least she couldn’t seem to. Was there a way to go easier on him, for once, without him knowing it?
With only five minutes to go, she saw him checking the clock more and more often too. She could actually see the strain on his face as he tried desperately to keep peeing – peeing enough to leak out of his diaper. She didn’t want to see him fail, yet she also didn’t want to make things easier on him. But she couldn’t stand it any longer – she could see how hard he had been trying. She just couldn’t punish him tonight for something that was really her fault – especially not after the way he had sent her into ecstasy earlier. She had everything already in place. He had done enough! “Sissy! Put your bottle down and come into my bedroom. Now!”
Chad was completely surprised. He glanced at the clock again, there was only a few more minutes to go. He looked down at his bare legs – no leaks. “But Mistress…”
“Don’t worry about it and get in here,” she commanded.
Chad had little choice but to do as he was told. Once he got to her room however, he was surprised to see that she had again spread plenty of protection all over her bed. Was he about to get whatever little pleasure she would allow him after what he had done for her? He could only hope.
“Lay down, Sissy. We’ve done this before.”
Chad laid down on his back on her bed. Mel quickly grabbed some of her rope and tied his wrists to the headboard. “We don’t want your hands getting in the way,” she said. As if he would! He expected her to tie his feet next, but she didn’t. Because of that, he expected her to remove his diaper… but she didn’t do that either. Instead, she pulled out the little bottle of glue remover and began painting it heavily all around his glued on breast forms. Chad felt like cheering. He couldn’t wait to get rid of the things. They were bulky, and heavy, and constantly in his way! How did women stand the things?
Little by little, Mel worked the glue loose on the breast forms, till finally they both released from his body. Chad immediately felt the pressure removed from his chest as the weight was lifted off of him. He felt the cool air against his nipples for the first time in a week. He breathed in heavily, enjoying the sudden sense of freedom. It was so much easier to breathe now. He wanted to rub and scratch at the area, but she had tied his hands out of the way. That would have to wait till later. Still, he was very happy to have them gone.
“They go back again tomorrow,” she said. “So don’t get used to it.”
Ugh!
He felt her undoing his diaper then, which surprised him all the more since she hadn’t been able to make it leak yet. Was she going to punish him now? He hoped not. He felt the cool air now touch his bare front as she pulled the sodden diaper down between his legs, preparing to pull it out from under him. But the moment the cool air hit him, he began peeing again.
Mel laughed a bit and pulled the diaper up a little more to make sure it caught everything. “Good baby,” she crooned in a teasing voice. Chad felt very embarrassed by it.
When it was safe enough, she removed the now wetter diaper from under him and left him alone, tied to her bed. She came back a few minutes later with a wet cloth that she used to wipe his chest where the breast forms had been, and then the area all around his chastity device. As she did so, she noticed that despite having the medium sized teeth in the device instead of the larger ones, he still seemed to be as small as ever. Perfect!
She spread some baby lotion over what she could reach on his front, then had him roll over – which wasn’t the easiest thing in the world for him to do with his hands tied as they were. She wiped his backside then and applied more baby lotion. As she rubbed it in, Chad was hoping that she would start playing with his backside again. The last time she had done that she had used a very interesting little toy on him. He’d wanted to see what it felt like again.
But instead of using her toy on him, Mel grabbed her jar of suppositories and removed the lid. “I hope these things are still working,” she said as she pretended to pull one out. A moment later she was rudely shoving her finger up into him as far as it would go, pretending to insert the imaginary suppository – that hopefully would work just as well as the real thing. Chad wasn’t at all pleased – even more so because it meant that she wasn’t going to play with him tonight. Darn!
She had him roll back over again and began fastening three of the thickest nighttime cloth diapers around him – the thickness adding lots of pressure against the inside of his crotch. Once the diaper pins were in place, she untied his hands. “You can get up now,” she said as she grabbed his plastic panties and held them out for him to put on.
Chad slowly got up from the bed. The pressure from the super thick diapers made moving more difficult. He had to struggle to pull the plastic panties on and then into place. And when he tried to walk, he was already waddling – and the diapers were still dry!
“Remember,” she said, “three more bottles before you go to sleep. And find yourself one of your onesies to wear to bed tonight.”
Three more bottles! But that was no surprise. That’s what she made him drink every night now. “Yes, Mistress,” he said as he attempted to curtsey in the super thick diapers.
Chad headed toward the door clad in only his diapers and plastic panties. He pulled the keys to his own apartment out of his purse and held them in his hand. He slung his purse over the crook of the same arm. He slung his diaper bag over his other shoulder. His clothes that he had removed earlier got slung over one of his arms, the shoes taking up one of his hands.
He didn’t know why, but he felt somehow sad and disappointed. Curtseying was pretty much impossible under the circumstances so he didn’t even try. “Goodnight, Mistress,” he said. Then he turned toward her door.
“Goodnight, Sissy,” she replied. “Sleep well, you’ve got a busy day tomorrow.”
Chad wanted to ask her what she had planned, but somehow, he didn’t think he wanted to know just yet. He would let the problems of tomorrow wait till tomorrow. He just nodded and opened her door. Then, walked out, clad in only his diaper and plastic panties. He softly closed the door behind him.
Mel stared at the back of the door as it closed. “Goodnight, Sissy,” she repeated softly. “Sleep tight.”