The Bet - Chapter 13 (Thursday – week 2 Part 1)

The Bet
by Karen Singer

Chapter 13 (Thursday – week 2 Part 1)

In the early morning hours, before consciousness could take hold of him, he dreamed. In his dream, he was wetting his diapers, strongly. Something fought its way through to his sleeping conscious mind and Chad woke up with a start to discover that he really was peeing into his diapers. He was a bit unnerved because he realized that he had woken up, not because he had to pee, but because he was already peeing. It was a strange, and troubling, feeling. Yet, somehow, he found it exciting. His diapers felt bulky, more than he would have expected. Had he wet himself while he was sleeping? He didn’t think so because he was sure he would have remembered it. Besides, he had woken up this time. He pressed his legs closer together against the bulk of his diapers. They were full and heavy. Familiar and comforting. Still surprised that he had actually started to pee without waking up, he allowed himself to drift slowly back to sleep again. To dream.
But morning dreams are very different than late night dreams. Morning dreams are more sexually stimulating and therefore much more urgent. Little pinpricks of pain began seeping their way into his dreams. Disturbing little things. Adding elements to his dream that fueled his need even more, which in turn increased the pain of the pinpricks. He started to come more awake, but he still held on to his dream. A dream that was nothing but need and desire. Like a raging bull, that need seemed to overcome him, he reached for that need inside of his dream. The abrupt swelling of his penis brought instant severe pain to his half-asleep mind. The tight confines of his cock restraint suddenly added yet another misery. Even through the pain, he tried to will himself to get bigger, he wanted and needed it that much. Yet the restraint denied him completely. It’s diminutive size foiling him utterly. Losing the dream now and only wanting the feeling of getting hard, he fought harder against the pain and the device. But there was no way to win. No way to even come close to realizing any piece of what he wanted… needed. Foiled and in great pain, he came fully awake. He slapped both his arms against his blow-up mattress in frustration. “Aaarrrggghhh!” he yelled into the still dark room.
He rolled over onto his back and concentrated on the feelings he was getting from his device. Horrible feelings. The pain from those little teeth burned enormously. For the first time he could feel pain in the very tip of his cock from where the slits in the device for his pee to come out of were pressing all too tightly up against the tip of his penis. Pain from tip to base, and no way stop it. Even if he could get at it inside his all too bulky diapers, there would be nothing he could do about it. The only remedy for him was to get soft again… somehow. He slapped his bed and screamed again. He hated the dread device more than ever.
Not being able to sleep anymore, he got to his feet and made his way toward his living room, turning on his bedroom light as he went through the door. That light was enough to get him to his kitchen, not that he had to worry about bumping into any furniture anyway. He turned his kitchen light on and immediately noticed the note that Mel had left him sometime during the night. He walked over and read it.

Sissy,
One bottle as soon as you read this.
Get cleaned up and into two fresh diapers
Second bottle
Girdle and tan pants today, everything else is up to you
Don’t do your makeup at home, bring it all with you to do here
Third bottle
Don’t forget your pacifier when you’re not drinking

Chad read it and felt his anger grow. “Everything else is up to you,” he mentally repeated. The very phrase made him furious. She knew perfectly well that the only choice he really had was what shirt to wear. Of course he could always wear a pair of high heels to work instead of the low heeled shoes he had worn yesterday… but not likely!
He noticed again the bulk of the diapers between his legs. They were so full… so heavy that they sagged. Had he possibly wet himself without knowing it? Couldn’t be! He remembered again waking up that one odd time when he caught himself already wetting. It had been strange, really strange! Angrily, he grabbed Mel’s note and wrinkled it up into a ball and threw it at the bag he was using for a trash can. It went right in. He cared that it went in, but he didn’t care. The device was still hurting him. And he was angry.
He was suddenly very sorry he had ever agreed to this bet. He was tired of wearing diapers. He was tired of being so constantly humiliated that he’d never ever live it down. He had never dreamed things would be like this. He had never dreamed it could hurt so much. He wanted out. He wanted it to end. He had had enough.
He walked back towards his bedroom, intent on removing his diapers and ripping off the cling wrap that Mel had put around everything. Denying him. He was finished.
The bright light from the kitchen behind him mixing with the dim light of his bedroom cast strange shadows around his empty living room. As he waddled through, he couldn’t help but notice the framed contract that hung on his wall, one of the few things that was in the room. He stopped in front of it and just looked at it. He didn’t have to read it, he knew what was in it all too well. Mel was a lawyer, and he had no doubt a good one. His eyes fell on the signatures where the contract had been properly notarized… made all too official and binding. By the terms of the contract, the only way he could come out of this well was to win it. The reality of anything else was too horrible to think about. He wasn’t a quitter. He never had been. The contract was legal and binding. Quitting would only condemn him to a life of exactly what he was going through already. He had no choice, he couldn’t quit. His only real solution was to somehow win this bet. A bet he had no doubt at all that he could win… would win. But winning was still a long time away. In the meantime, he was stuck with whatever wicked and weird things she could think up to make him ever more miserable. And he knew now that she could be particularly devilish.
Disgusted and angry with his whole life, he headed to his bathroom to change his diapers early. Wow, they felt full. Had he wet himself in his sleep last night? Couldn’t be! He would have remembered it.

Mel allowed herself to sleep an extra half hour. When her alarm went off, she was already mostly awake. She stretched, enjoying the fact that for once she wouldn’t have to hurry out to unlock Chad’s onesie and he could change himself. She was fairly sure she didn’t have to worry about any of the reasons she had locked him in the onesie in the first place. With his chastity device now firmly in place and his toilet all sealed up, there wasn’t much he could do anyway. Thinking about how much under her thumb she had him now, stimulated her sexual need tremendously. She sighed. If only she wasn’t on her period!
She got up and went into her kitchen to make some coffee, then headed to take her shower while it was brewing.

Chad sat dejectedly in the only chair he had, finishing his third baby bottle of the morning. He had already peed twice since he had changed himself earlier. He considered changing himself again before he went to work. But glancing at his watch told him he didn’t have enough time. Feeling angry and depressed, he finished his bottle, then dropped it into a small bag with his other empty bottles to carry over to Mel’s apartment because he was sure she would want to see them.
He picked up his purse as he headed for his door and stopped. His purse. He was carrying a damn purse like a girl… full of makeup! Not to mention the way he was dressed. Thinking about it fueled his driving sexual need, which sent pain to the root of his cock, which made him angry again… well, more angry. Damn the woman for doing this to him! Not knowing any way out of it, he opened his door and walked over to Mel’s apartment.

Mel was fully dressed and enjoying her coffee by the time that Chad knocked on her door. She set her cup down and went to let him in. She opened the door and purposely stood in the way, waiting, not letting him in. He stood in front of her, looking at her silently. Did she detect a hint of anger on his face? “You have something to say?” she asked.
“Good morning, Mistress,” he said to her. There was definitely a hint of something not right in his voice.
“I can see we need to do more practicing tonight,” she replied. “Now do it right and curtsey!”
Chad was aghast. “Out here?”
“Of course! There’s no reason why you can’t do it anywhere!”
Chad wasn’t happy about it, but she wasn’t giving him much of a choice. Realizing that his hands were full, and he couldn’t reach down like he was grabbing his skirt, he replied, “But my hands are full.”
“Then you do what you can!”
Chad held back his anger only with great restraint. He put his right foot behind his left and dipped down. “Good morning, Mistress,” he said again.
Mel nodded and stood back. “Much better.” As he walked past her and she closed the door behind him, she was more convinced than ever that something was eating at him.
Chad dropped his purse on the floor and handed her the bag containing the empty baby bottles. “Thank you,” she said as she grabbed the bag and looked at the contents inside. He had been good again.
“Can I get started on my makeup now?” he asked flatly.
“Not yet. I’ve been nice to you this morning and made you some breakfast. Now come into the kitchen and eat it.”
Breakfast? He couldn’t believe it. She… had made him some breakfast? He followed her into the kitchen where she pointed at his usual spot on the floor. He sat down.
“Where’s your pacifier?” she asked as she pulled a baby bottle full of her tea mixture out of the refrigerator and handed it to him.
Chad rolled his eyes. “I left it home. I forgot it. Sorry.”
“You can get it later,” she replied as she headed toward her counter. She picked up a bowl and the spoon that was laying next to it. She turned around and handed Chad the bowl. “Some nice warm cereal for you this morning,” she said.
Chad took the bowl from her hands and looked at the contents. It looked kind of like oatmeal, only completely smooth. The bowl felt slightly warm so it probably was some kind of oatmeal. Well, that was fine with him. He would have preferred pancakes or something like that, but he appreciated the effort. “Thanks,” he said.
Mel stood up straight. “I think you can do better than that!”
Chad corrected himself quickly. “Thank you, Mistress.”
“I can see we still have a lot of work to do with you.”
Chad was about to start trying to stuff the oatmeal into his mouth with his fingers when Mel stopped him. “I think we can let you use a spoon for that this morning,” she said.
Chad detected something in the tone of her voice, but couldn’t tell what. He quickly found out though as she produced a tiny rubber-coated baby spoon and held it out for him. He took it hesitantly. The thing was so small. But it was better than eating with his fingers. He stuck the spoon into the cereal and scooped some up. He was dismayed to see how little the spoon had picked up. Not much to put into his mouth. He tasted the cereal, bland, very bland, but eatable. It didn’t taste like any oatmeal he had ever had. He tried to scoop up a bigger amount and put it into his mouth, but the baby spoon was too small and part of it dripped on his chin before he could get it all into his mouth.
Mel laughed when she saw him dripping on his chin. “Maybe we need to get you a bib too.” She turned and opened one of the drawers and pulled out a dish towel. She draped it around his neck to catch any further drippings. “More and more like a baby,” she teased. “How does your baby cereal taste?”
Chad was shocked. “Baby cereal!” He looked down at the bowl then back up at Mel. No wonder she had made him breakfast. It was baby cereal! “Kind of bland and not really very good,” he replied.
“That’s what’s best for babies,” she replied. Then she turned away while he continued eating.
As Chad ate the baby cereal, he felt even more humiliated. The damn woman could certainly come up with the darnest ways to make his life more miserable. That was for sure. As he continued eating, he quickly discovered that trying to eat with that tiny spoon was far more difficult than if he had been using just his fingers. It certainly took a lot longer too. Worse, the more he ate, the worse the stuff started to taste. When he started eating it, it had seemed to taste fine, just a little bit bland. But soon he was having to put a little in his mouth, then take a swig from his bottle just to keep eating it. By the time he was half-finished, he was forcing himself to continue eating. “Mistress!” he called desperately.
Mel came quickly back into the kitchen. “I can’t eat it anymore. I can’t even get it down. It’s horrible!”
“Awww,” Mel crooned. “Babies love it. So I guess you’re going to have to learn to love it too.” She noticed that the bottle next to him was almost empty. She pulled yet another one out of the refrigerator and set it down next to him. “Just in case you need it,” she said. “Now finish it all up like a good little baby.” She was chuckling to herself as she walked away.
Chad just stared at her retreating back. Damn the woman. “Finish it all up,” she had said. Yuck! He went back to work on the bowl of mush. He wasn’t happy about having another bottle to drink either, but he’d need it to get this all down.
By the time he finished, his stomach really wasn’t feeling all that well. “Mistress, I’ve finished,” he called from his spot on the floor.
Mel came back quickly and took the bowl from him. “Oh what a good baby you were. See, that wasn’t so bad now, was it?”
Chad wanted to tell her in no uncertain terms how awful the stuff was, but he said nothing.
“Oh come on,” Mel crooned at him like he was a baby, “tell me how much you liked it.”
Liked it? His stomach felt sick now from the junk! He got to his feet, the anger in him slowly building again. He felt the need to pee again as soon as he was standing. Frustrated at having no where else to go except in his diapers he let it out.
“Aren’t you going to tell my how much you liked it?” Mel asked again, this time in a much more angry tone of voice.
Something in Chad began to snap. “Like it? It was terrible! I feel sick now from it! I feel sick now from all of this crap!” He walked off into the living room.
Mel followed right behind him. “What are you saying?” she asked menacingly.
Chad’s anger finally came all the way through. “I’m sick of all this! I’m sick of wearing diapers. I’m sick of being constantly humiliated. I’ve had enough. I’m finished. And I want this damn… thing… removed from my cock… now!”
But he was up against a well seasoned lawyer who was well used to fighting back and winning. Mel had been in a lot of battles in court that were a lot worse than this. Her lawyer instincts and training took over. “So you’re quitting?” she said almost gleefully.
“Damn right!” he replied.
“You know what that means, don’t you? It means that I win and that you have to continue to do anything I want you to. Which means that I’m going to keep doing just what I’m doing now… and more!”
“Like hell!” Chad replied. He was frustrated. He already knew what the contract had said. He just didn’t want it anymore.
Mel went quickly to her desk and grabbed her framed copy of the contract and brought it back to him. “See that?” she asked. She pointed at the signatures. “See where you signed it? You signed it because you knew you might want to back out someday. You signed it to make sure you wouldn’t have any way to back out. You signed it to make sure that no matter how much you wanted to quit, you wouldn’t be able to. You signed it… yourself. And you did it in front of not only me, but another outside witness. You signed it in front of a legal notary. And there’s her stamp of certification! And you did it willingly didn’t you?” She waited for his answer. She knew she had him, but he had to fully realize that again. “You did it willingly, didn’t you?” she repeated, pressing him.
Finally he nodded his head. “Yeah,” he replied softly. She could see the anger in him starting to subside, but it was still there, mixed with confusion.
“Yeah,” she repeated back to him, mocking him. “Yeah… you signed it willingly, knowing full well what this meant. Knowing that the only way out for you is to win this bet. Isn’t that right? Hmm? You knew it!”
Chad nodded his head again. He was looking down at the floor now, felling sorry for himself. “Yeah, he said again.
“Yeah,” she repeated. Again mocking him. “So which is it now, are you saying that I win so I can get on with turning you into exactly what I want? Or are you just feeling sorry for yourself?”
Chad’s mind had dropped into total numbness. He was trapped and he knew it. Furthermore, she had quickly pointed out that he had trapped himself. He had done it to himself. By signing that thing in front of the notary, he had locked himself into all of this. And he had done it willingly. No matter that he didn’t want it anymore, he was stuck. His only way out now was to win the bet. A bet he was still fairly sure he couldn’t lose, which was a good thing because he wasn’t at all sure he liked any of this anymore, at least not right now. He was stuck, stuck, stuck!
“Well?” Mel asked again. “Do I win? Say it. Say it plainly so there’s no misunderstanding for either of us.”
His only way out was to win. And he could win. He had no doubt of that at all. A tiny spark of life seemed to return to him. A spark of life and confidence. “No!” he said. “You don’t win. This bet is still on! There’s no way you can win.”
Mel had been sure from the start. She had just been surprised at the way it came out. “So you’re just starting to feel sorry for yourself, is that it?”
Chad took a deep breath. “Yeah,” he said.
Mel had worked with enough clients with heavy troubles to know there was a time to push hard and a time to go easy. She returned the framed contract to her desk, giving him more of a chance to recover himself. She had no doubt at all that he was feeling really sorry for himself, but that was something he was going to have to get past. It was time to make him realize that he was still riding her train. Time to show him he was on her track… But only just a little. “Tell me you’re sorry,” she said.
It took a moment, but finally he let out a small, “Sorry.”
“That’s not an answer!” Her voice whipped at him like a lash. He looked up at her, clearly startled. “You do it properly… and curtsey!”
Chad was so startled and off balance that he didn’t even pause. “I’m sorry, Mistress,” he said as he dipped into his curtsey.
Mel nodded as if she were satisfied. “That’s better!” she replied. “Oh, we’re definitely going to have to do a lot more work with you tonight! Unfortunately, we can’t get started too soon because we have therapy this evening. But you can bet you’ll be practicing a lot more, later!”
Therapy… Chad had forgotten all about that. It had been the one, and only, really good thing he had done last week. Suddenly he had something bright to look forward to today.
Mel saw Chad’s face change a bit as soon as she had mentioned the therapy session. He was recovering from his bout of anger and quickly. It was time to keep him moving. “Ok, Sissy, do your makeup now.”