The Bet - Chapter 24 (Monday – week 4 Part 1 of 5)

The Bet
by Karen Singer

Chapter 24 (Monday – week 4 Part 1 of 5)

Her dreams were fuzzy… mixed up… colliding. She was successful – she wasn’t successful. She had everything – she had nothing. She was loved – she was scorned. None of her dreams made sense. None of her dreams were fulfilling. And when her alarm clock woke her up, that’s exactly how she felt – unfulfilled. Not to mention feeling cotton headed and having a bad taste in her mouth once again from the wine the night before. Ugh!
She rolled out of bed and turned her alarm clock off. She found the courage to grab her robe and went directly into the bathroom to brush her teeth. Better… somewhat. She went into her kitchen to start the coffee and stared at the machine for a few moments before she actually did anything with it. Why did she feel so lousy? Must have been the wine last night. No, it wasn’t that she really felt lousy, well, she did, but it was more than that, she felt a bit depressed. Why?
She stood there and watched the coffee dripping down into the pot. When it finished, she took a mug and filled it. She took a sip. Mmmm. Liquid. Hot and wet. She took another sip and headed into her living room to curl up into a chair and enjoy her drink. Why should she be depressed? There was no reason. None at all. And if there was no reason, why was she dwelling on it? Dumb!
She thought about Sissy. He had been so good last night – again. She thought again about the way he had told her last night that her body was beautiful – while blindfolded. Just thinking about it sent warm fuzzy waves through her. She smiled. He could be so nice.
He had brought her to orgasm after orgasm again last night. But was it her imagination, or did he seem to be colder about it this time… just going through the motions? She wasn’t sure. But he had told her she was beautiful. And he had never even seen her body naked. Never.
She smiled again as she took another sip of her coffee. If only he were someone else. If only he were a real man instead of… whatever it was that he was. She supposed that the word “sissy” really summed it all up for him. He was a damn sissy! And as such, he craved… no, he really deserved… everything she was doing to him. Damn him! Why couldn’t he have been… normal!

Chad stared up at his blank white ceiling. His alarm clock hadn’t gone off yet. The morning dawn was just now starting to send tiny tendrils of light around the shades at his windows. It was Monday. Another day. A work day. It would be another day of humiliation for sure. Just like all the rest of his days. Ugh!
His pink alarm clock suddenly began blaring loud rock music into his room and he forced himself up off of his blow-up mattress to turn it off. Blessed silence. It felt like a relief.
His whole body felt weighted down. The bra and breast forms that were stuck to his chest felt heavy. His overly bloated diapers felt heavy, and wet, and messy… and warm, and sensuous, and wonderful. Oh how he wished he didn’t have that miserable chastity device locked onto him! Oh how wonderful it would feel to finally be able to get hard again. And if he could get hard… oh what he would do! He thought about that for a moment. What would he do? He needed relief, that was for sure! But he didn’t want to just shoot his load and be done with it all at once. A need as great as his deserved to be acknowledged… savored… used… rewarded. What would he do if he had the freedom to get hard and get the relief he so craved? Damn. His brain couldn’t even begin to wrap itself around that question. He smiled. But it sure would be fun to think about all day.
He slowly waddled his way into the kitchen to see if she had left him a note. He was glad to see that she had.

Sissy,

First bottle.
Get cleaned up.
Second bottle.
Get dressed. No waist cincher or bra, but wear one of your new girdles. You know the rest.
Third bottle.

That was it. Nothing really out of the ordinary. He was glad he didn’t have to wear one of the waist cinchers, but those new girdles… They were a size smaller than his old ones and he had no doubt that just getting one of the darn things on was going to be difficult.
He went to his refrigerator and pulled out one of the many baby bottles of her tea mixture and went into his living room to sit in his only chair to drink it… and to think about what he might do if he could get hard again. He felt the first tiny stings of pain from the teeth in his chastity device, yet he couldn’t stop examining his interesting question of the day. When his bottle was finally empty, he was ever so glad to realize that the stings from the chastity device had never gotten any worse… they hadn’t gotten any better either, but at least they hadn’t gotten any worse. His only real problem was, that he had never come up with any decent ideas – none at all. Troubling!

Mel dressed in one of her more conservative suits. One that she thought made her look more professional than some of her others. She would be spending a lot of time in court today and this judge seemed to be overly interested in professionalism. Well, she could certainly show him that. What she wasn’t sure was how this case would come out. But she would do her best.
As she looked at herself in the mirror, she once again remembered Sissy telling her that he knew she was beautiful. What would he think about her when he saw her wearing this suit? Would he care? He was a sissy after all. Maybe he didn’t care. But deep down, she had a feeling that he did care… she hoped anyway.

Chad struggled to pull his girdle up his body. The task was made all that much more difficult because of the extreme nails on his fingers, he couldn’t grab anything the way he really needed to. But he persevered because he had to. He finally got the thing up and over the breast forms that were stuck to his chest, then he pulled the straps over his shoulders and breathed a small, quick sigh of relief… sort of… the damn girdle was way too tight! Ugh! And he’d have to wear it all day! Double ugh!
He felt how tightly it compressed his whole body – especially around the thickness of his diapers. And the straps… he had adjusted them to their longest setting, but they were still too small and the entire thing seemed to pull on him too much. It was going to be a long day – a very long day – as usual.
He turned to his closet. Finally, he could wear some pants again – even if they were women’s pants. He had worn nothing but skirts for the last three days in a row! Three horrible… humiliating… days! What a luxury it felt to pull the pants on. Except that with the new girdle, he noticed that the waist of the pants was a bit looser now than usual and the pants kept falling down to ride further down on his hips.
He selected one of his blouses to wear with the slacks. It fit tighter over his new breasts than he was used to, but it did fit.
He grabbed the low-heeled shoes he usually wore and slipped them on. Comfortable. But then he noticed that the bottom cuffs of his pants were too long because they had slipped down so far. He pulled them up, and they slipped down again. The smooth fabric of the girdle wasn’t going to let them stay all the way up. His girdle was too small… and because of it, his pants were now too big. Not quite knowing what to do about it, he took his shoes off and selected another pair with a slightly higher heel. At least his pants wouldn’t be dragging on the ground now.
He stood in front of his full length mirror for a few moments to see the overall affect of how he looked. His hair was ok. His makeup he thought was ok too. The new breasts definitely made a difference in his shape as did the tighter girdle. He thought about the waist cincher he had worn yesterday… that had really made a difference. Too much of a difference. He was just glad he didn’t have to wear the damn device today to work. The girdle was bad enough! Overall… he supposed he looked ok. From a distance – a long distance – someone might even think he was a woman. But the closer he looked, the more he saw a man underneath. Ok, maybe not a real man… a sissy. But that’s what he was… wasn’t he?
He walked back to his kitchen and grabbed his third baby bottle for the morning. The tape wrapped tightly around the top made sure that he couldn’t remove the nipple and pour it out or even drink it any way except through the nipple. He sat once again in his only chair and thought about what he would do if he could get hard. A dream. He knew it. He wanted it so badly… but what would he do? That was the question. He wasn’t coming up with any ideas at all. He only knew that he wanted… badly… to get hard!
He did know that he’d like to shove his long hard cock into something… something exciting… but what? And then what would he do? He wanted to prolong the experience, he was definitely sure of that, but if he got to shove himself into something, he had no doubt that he’d cum immediately, which was what he didn’t want. And shove his cock into what? His first thought was Mel. Yeah, that would definitely be nice. But he wasn’t fooling himself, she’d never allow that and he knew it.
He remembered making love to his wife – make that ex-wife. It really had never been all that fulfilling for him. He had gotten through their love making by fantasizing about sissy things – every single time. Their two and a half years of marriage were over now… well, it would be officially over later this week. The thought of that made him feel bad. He was a failure! Without a doubt, a failure. All because he was a damn sissy. And what could he do about it? Nothing! For that matter, what did he really want to do about it? Nothing! Nothing, except perhaps embrace his sissyness even more now that he was single again. But wasn’t that what he was doing right now with Mel? Definitely. It just wasn’t working out exactly the way he wanted it to. Things were far more difficult and humiliating than he ever believed they could be. Mel had taken everything way too far. It was this damn bet! She didn’t want to lose. He thought about it for a moment while he finished his bottle. She didn’t want to lose, but then, neither did he. He would win this bet in the end… no matter what he had to do! “Self-respect. Friends. And a life!”
He glanced at the tiny dial on his watch. It was almost time. He quickly found a plastic bag and put all his empty bottles into it to take to Mel. He checked his hair and makeup one more time, then grabbed his purse and slung his diaper bag over his shoulder. He was ready. It was time to get humiliated again.

The knock on her door came right on time. Mel opened it and smiled.
“Good morning, Mistress,” Chad said as he dropped a small curtsey.
“Good morning, Sissy,” she replied as she stood back out of the way, allowing him to enter. It had quickly become a morning routine… one that she absolutely delighted in. It was good to see what he had already become. And it was especially pleasing to see him curtsey so often. What immense fun!
She took the bag of bottles from him and examined it quickly while he put his purse and diaper bag on the floor by her table. Perfect as usual. He was standing still now, waiting for her to inspect him. She began looking him over carefully. She was mildly disappointed to see that he had worn slacks instead of a skirt, but after not being able to wear slacks for the last few days she had no doubt that he’d choose slacks today. She walked all around him. Yes, he looked good… except for one tiny thing. “Sissy! Where’s your pacifier?”
He couldn’t believe it! He had forgotten it again! “I’m sorry, Mistress, I forgot it again. I don’t believe it!”
“Go get it!” she ordered. “And quickly!”
He grabbed his keys out of his purse and made a rush back to his own apartment to get the darn thing. He stuck it into his mouth, not even thinking about not sucking on it and rushed back to her apartment. She was standing there with the door still open, waiting for him. “Sorry, Mistress,” he mumbled past the pacifier in his mouth as he reentered her apartment.
“Don’t forget it again!” she warned as she turned her back to him and headed to her kitchen. “Come along now, it’s breakfast time.”
Ugh! The last thing he wanted just then was more of the baby cereal that she fixed him every morning. Yuck! But as with everything else, what he wanted made no difference. Very quickly, he was trapped into the big highchair and was attempting to feed himself the tasteless mush that she called cereal with the tiny baby spoon. And as usual, all too much of it dripped straight off of the spoon, onto his chin, then down onto his bib. He cared, but he didn’t care. He was becoming too used to it now. It was just part of his typical humiliating morning routine.