The Bet - Chapter 19 (Wednesday – week 3 Part 5 of 5)

The Bet
by Karen Singer

Chapter 19 (Wednesday – week 3 Part 5 of 5)

When Mel came back, she helped him out of the tub and dried him off herself. Her attention was really nice. Sensual in a way. But Chad’s mind was more on what lay ahead and he wasn’t looking forward to it. “Come along now baby,” she said as she took him by the hand and led him into her bedroom.
The blankets on her bed were pulled back and the top was heavily protected under layers of plastic and very thick diapers. He could see the ropes attached to the headboard and the footboard. With a sigh of inevitability, he laid down on her bed and held his arms over his head so she could tie them. “Good baby,” she crooned softly. He hated it, but her voice sent a quick thrill through him.
All too soon, his arms were stretched tightly above him and his legs were stretched the opposite direction. He wasn’t going anywhere and he knew it. He didn’t even try. This time though, Mel climbed up on the bed and laid down next to him. She propped her head up on a pillow and watched him. He turned his head to look at her. She really was a beautiful woman. If only, if only!
Mel reached out and ran her hand lightly over his chest. Her touch sent instant thrills throughout him. “Cassie tells me that you did really well today when she tried to stimulate you.”
He was a bit surprised. “Yeah,” he admitted sheepishly. “I guess I did.”
“You’re learning really well already then.” He didn’t reply. She was right, he guessed he was learning… something. “She also said that you’re having some very interesting reactions when she plays with your backside. Is that right?”
He really didn’t want to admit it, but he had no doubt that Cassie had shown her the really embarrassing pictures from last night. The ones she had said she wasn’t going to show Mel. He blushed deeply and closed his eyes. The pictures meant that he couldn’t deny it. He hated saying it. “Yes, Mistress. I did.”
She was about to continue, but suddenly he was still speaking. His eyes were still closed as he spoke. “You saw the pictures from last night.”
She was taken off guard. What was he talking about? “Yes, I did see the pictures,” she replied, wondering what any of the pictures she had seen had to do with the present situation.
He opened his eyes finally and looked at her. “You saw how I reacted when they stuck that thing in me. I loved it. I hate that I did, but I loved it.” His voice was growing more and more upset and emotional. He began thrashing at his bonds in frustration. “I fucked myself on it!” he finally admitted as tears began falling from his eyes. He turned his head away from her as if trying to hide. “I hate myself for it, but I couldn’t help it,” he added a bit more softly.
Mel was shocked. Deeply shocked. Cassie hadn’t shown her any pictures like what he was describing. Obviously, Chad was very upset, and his anger was focused on himself and only himself. “Shhh, Sissy,” she said softly. “It’s alright. You don’t have to be angry about it.”
He turned his head back to face her. “But I am angry. I shouldn’t like it that much!” He turned his head away again.
Mel took a deep breath. She needed time to think, but now was not the time. There were other things to do first. “It’s ok, baby,” she said softly again. “Listen… Look at me.” She waited till he turned his head back again. “You’ve been wearing that chastity device for a whole week now. And you’ve done really well with it. I’m proud of you. So tonight, is not about me. Tonight is only about you. Tonight you’re going to get some reward.” She watched him as he took that in. It took a few seconds, but she suddenly saw his eyes widen in surprise.
“Reward? You mean it?”
She nodded her head. “Yes. You deserve it.”
“You’re going to grant me some relief?”
She giggled. “Definitely.” Then she put her mischievous smile on her face, “Eventually.”
She rolled off the bed and walked around to the other side where she sat down next to him. She looked at his chastity device. She needed to remove it. But there was something else starting to intrude into her mind. Cassie had said that she needed to explore his newfound interest. And he had just told her how much he had love it… while at the same time telling her how much he hated it. But she was curious. “Sissy,” she finally said softly, “would you mind very much if you showed me how you like your bottom played with?”
Chad’s mouth gaped open in disbelief. What was she asking? He began thrashing at his bonds and shaking his head back and forth again in frustration. Didn’t she understand how much he loathed himself because of it? But at the same time, he felt the powerful need from having no sexual relief in so long. And as he slowed his thrashing, that need became remembered feelings from doing it before. He wanted it. He needed it. But he hated it so much!
Mel watched him thrashing on her bed. As he finally slowed down again, she was about to say that it was fine, that he didn’t have to, but he beat her to it. “Ok… Yes, Mistress.” He said simply.
She was shocked. After all his thrashing about, he was suddenly agreeing? “Are you sure? We don’t have to…”
He closed his eyes. “Yes,” he said again in almost a whisper.
She moved down to the foot of the bed and untied his feet, then she released his arms. As he rubbed his wrists, she asked, “How should we do this?”
Chad covered his face in his hands as if to hide for a few moments. The he rolled over and pulled his legs up under him, exposing his naked backside up into the air for her. “Cassie massages me with baby lotion first,” he explained with his face stuck into her mattress and his arms covering his head. There was no way he could look at her. He was too ashamed.
“Ok,” she replied. His voice was a bit muffled by his position, but she wasn’t going to say anything about it. She quickly grabbed the baby lotion off of her nightstand and squirted it onto his backside. She saw him shudder at the sudden cold feeling. But she began massaging it into him, all around him. “What’s next?” she asked.
Chad surrendered himself to the wonderful sensation of Mel rubbing the baby lotion all over his backside. He heard her question, but he was too occupied with enjoyable sensations just then to answer. Without realizing it, he began moving his butt back and forth against the motions of her hands, increasing the pleasurable feelings. But he needed more. He wanted more. He had to tell her.
Mel could barely understand him when he spoke since he was speaking into the mattress. But she did her best to listen intently. “She usually starts to play with my hole just a little bit at a time. Then she slowly increases the pressure till her finger just slides in. Eventually, she works it back and forth. But as you saw from the pictures last night, they used something else on me instead.”
Mel lightly moved her finger over his little hole and pressed lightly. She saw the immediate reaction in his whole body. What pictures was he referring to? Obviously Cassie had some that she hadn’t shown her. And what had they used on him? She thought about what Cassie had suggested earlier. She had a vibrator of her own in her drawer and she had put fresh batteries in it just a little while ago, intending to use it on him at Cassie’s earlier request. Had Cassie and Sandy used something similar?
Instead of putting her finger up inside of him, she leaned down close to where he could hear her better. “Baby, I have a little toy we can try on you if you like. Can I?”
His muffled reply took a few moments. “Yes.” She thought she heard the sniffle of some tears. She hugged him briefly then opened her nightstand and pulled her vibrator out. He was still hunkered down, ass in the air, head into the mattress. “It’s ok, baby. It’s nothing to be ashamed of,” she told him softly. He turned his head away from her. Obviously to him it was.
“Come on,” she said softly. “Why don’t you pull your head up a bit. Besides, I want to see your little thingy all trapped inside of its cage while I do this.” He didn’t move. She leaned close to him again. “And then maybe I’ll take it off.”
He turned his head back towards her and moved his arm so he could look at her. “You mean it?”
“Of course.”
With a weary sigh, he hauled himself up onto his hands and knees on her bed. She smiled at him. “That’s better, baby.” Her words of praise sent thrills throughout him. She reached under him and lightly grabbed his chastity device and shook it lightly back and forth. “We’ll get this thing off of you in just a little bit.” She grabbed some KY jelly out of her drawer and lubed her vibrator well, then she set it lightly against his backside. “Ready?” she asked.
From his now kneeling position, he turned his head to look back at her. He was a bit frightened. This wasn’t at all like the sensual way that Cassie did it. He took a big breath to steady himself and nodded. “I guess so.” He turned his head away and closed his eyes. He didn’t want to look.
This was all new to Mel. What should she do? She was only guessing as she went along. Very lightly, she placed the tip of the vibrator against his hole. Did he want it turned on? She wasn’t sure so she decided to leave it off for a while. She pressed it harder against him. How hard would she have to press before it went in? What would happen when it went in? But as she held it there, trying to decide if she should push on it or not, she suddenly felt him pushing back against it a little bit. She pushed a bit harder towards him. Then a bit harder still. Her eyes went wide as the tip of it actually began to penetrate him. She saw his whole body tense up tightly beneath her.
The electric current shocked its way through him once again the moment her dildo penetrated him. Why did he like this so much? Why did it have to feel so damn good? The toy she was using on him wasn’t at all like whatever Cassie had used on him last night though. This one was smooth and skinnier, not fatter and ribbed. As the toy slowly slipped further and further into him, he realized that it gave him a lot less sensation since it was so totally smooth. Yet still, he loved it.
Mel kept pushing, watching wide eyed as the vibrator slowly disappeared up inside of him. How far did she have to push it? Would it hurt him if she pushed it too far? She worried about that. It was almost in up to her hand - as far as she would probably use it on herself when she felt him trying to move away from him. She pulled back on it now and watched as it came out again. But she didn’t remove it completely. Very soon, she was pushing on it as he was moving back towards her again. A minute later, she was grabbing it with both hands to hold it steady as he began rhythmically moving himself in and out against it.
Chad felt it going in and out of him. He was doing it now, not her. He was controlling it. He had to. He hated doing it, but he just had to – she wasn’t providing him with enough sensation. He began pumping himself against it harder, faster. But it wasn’t enough. He needed sexual relief… badly! Her little dido felt fantastic, but it wasn’t enough. Not by a long shot. He needed his penis uncovered… untrapped… where it could get hard. He needed to feel something from his penis to get off. He thought about peeing, but there was nothing ready to come out of him. Still, he pumped himself against her toy.
Mel held on harder as Chad rocked himself back and forth, obviously enthralled by what he was feeling. Did it feel anything like she felt when she used it on herself? Somehow she doubted that. She decided to try moving it around a bit. She rocked it back and forth as he pumped in and out, then she tried rocking it up and down.
Chad felt her moving the toy around now. The added sensation felt incredible. Much better than when she just held it still. But now she was pushing it up and down, over and over again, and something felt different, strange. It almost felt like he had to pee, but he didn’t have to pee. But then there was something coming out of his penis as if he were peeing. And it felt good, really good. But he needed more. He needed to touch himself. He needed to get hard to climax.
Mel stared in disbelief as she saw the liquid suddenly coming out of him. She thought he was peeing at first which really thrilled her. Imagine… peeing during sex - when before he couldn’t pee because he was sexually stimulated. But as she looked closer, she saw that the liquid that came out of him wasn’t pee at all, it was milky and thick. She glanced quickly under him. His penis, still trapped in the device, was completely small and tiny. No reaction from that at all, yet it was dripping cum as if he were peeing. She kept pumping the dildo up and down as he rocked even harder against it till the liquid stopped coming out of him.
Chad suddenly groaned in frustration and slapped the bed with his arms as he bent his head down into the mattress again. He stopped moving. It was no use. He couldn’t get any relief from just the anal stimulation – no matter how good if felt. He felt Mel pulling the toy away.
Mel put the vibrator back on her nightstand and put her arm over him. “Are you ok?” she asked tentatively.
It took a moment before he could collect himself enough to answer. “Yeah.” He got fully back up on his hands and knees again. I need more than that to get off though. I need to be able to get hard. Please, Mistress?” he asked pleadingly. “I really need it.”
She smiled at him. “Of course. But let me do it for you.” She had been fascinated by what she had just witnessed – taken part in. Cassie had been right, it was just something that she had never considered. And judging by Chad’s reactions, it was something new in his life as well. She laughed a bit as she pulled on the diaper underneath him that had collected all his sperm. “You made a mess though,” she said as he moved his weight off of it so she could remove it.
She rolled him over on his back and grabbed his wrist and pulled it up toward her headboard. He rolled his eyes at her and looked pleadingly at her, not wanting her to tie him up again. “Shhh,” she said softly. “I want to do this for you, ok?”
He reluctantly agreed and soon he was once again completely bound and helpless on her bed. She was fiddling with the chastity device now, removing the lock and placing it on her nightstand. He held his breath as she pulled the encasing cover off of him. The cold air that hit his shriveled penis felt good. He wanted badly to touch it… to massage it, yet he couldn’t because she had him tied. She removed the rest of the device, the part that held it all so firmly attached to him. He breathed a sigh of relief as it was gone. Again he wanted to touch himself, or at least to scratch at the area where it had been removed from. “I’ll be right back, baby,” she said softly. Then she was gone.
She came back a minute later with her razor and a washcloth. Very shortly, she had removed all the stray hairs from that area of him and was massaging his now free cock with her warm wet washcloth. It felt like heaven. He closed his eyes and concentrated on it. His sexual need was so great. She was touching him, massaging him. Yet he wasn’t getting hard. As if he couldn’t get hard.
Mel looked at him strangely as she used the washcloth on him. She was massaging him with the washcloth and he appeared to be loving it, yet his penis wasn’t reacting. She put the washcloth down and began using just her fingers instead, touching him, urging him with her hands to get hard in the way that she had totally denied him before. It took a while, but eventually he swelled somewhat in her hands. But it was only somewhat. She felt him trying to rock back and forth, pushing against her hands, and she did everything she could but he wouldn’t get any harder. He couldn’t seem to come any closer to the relief that she knew he needed… and that she wanted him to have. She was becoming frustrated from the effort, and obviously, so was he.
Chad tried as hard as he could. Her hands were like magic, but he wasn’t getting any harder, and he couldn’t seem to cum. It hit him fully then. She had inadvertently milked him. Or maybe it wasn’t so inadvertently… he didn’t know. But either way, he wouldn’t be able to get any relief. Not for quite a while. He groaned in frustration as he thrashed against his bonds.
“What’s wrong, baby,” she asked, totally concerned.
“You milked me!” he almost shouted.
“I what?”
“You got all the cum out of me already and didn’t allow me to get the full release that I need. I can’t come now!”
His frustration was so evident. Milked him? She had to think about that. It was a concept she had just barely heard of. Was that what had happened when he had released all that sperm earlier? And now he couldn’t cum? Was it true? That wasn’t what she had intended at all!
“You’re kidding!” she exclaimed. “You mean you can’t cum now?”
“No! There’s nothing left. Just all this pent up insatiable need! And it’s so frustrating!”
Mel was actually crestfallen for him. She placed her hand lovingly on his chest. “I’m sorry, baby. I didn’t mean to. I didn’t know. So you mean there’s no way?”
He shook his head. “Believe me, I’d really love to. I need to… but I can’t.”
She sighed. “I’m sorry, baby,” she repeated.
He didn’t know whether he believed her or not. Once again he was being denied - even if she hadn’t meant to do it to him. His frustration suddenly increased all the more as he felt her rubbing some kind of lotion all over his privates then fastening the chastity device back on again. He almost screamed as she placed the main cover back over his penis once again. Trapping him. Denying him. Totally.
And when she stuck the suppository up inside of him, he received no pleasure from the act at all, only revulsion. With almost clinical quickness, she was fastening up the thick night diapers all around him.
His life was back to the usual again. The relief had been offered… then taken away. Denied.