The Bet - Chapter 35 (Friday – week 5 Part 1 of 8)

The Bet
by Karen Singer

Chapter 35 (Friday – week 5 Part 1 of 8)

Her dreams were mostly scattered images, flitting from one vague subject to the next. But as the night wore on toward morning, more and more of those dreams became about Sissy. Eventually, even though she remained mostly asleep, her conscious mind became aware of her dreams – or thoughts. Sissy – in a pink leotard with white tights and a white tutu, pink ballet slippers on his feet, dancing to her favorite ballet music. Sissy – out on a date, with a man, feeling horribly humiliated as he was forced to dance with him… and then kiss him! Sissy – playing poker with all of his friends – but there were no exciting or even revolting feelings from this last dream. Yet the dream refused to go away.
Over and over again the final image of him playing poker with the guys played itself in her mind. Consciously, she became more and more bothered by it. Why couldn’t she get it out of her head? It was all wrong for him. She didn’t want him doing ‘guy’ things at all! Her conscious mind knew perfectly well that he wasn’t going to do it, yet she still couldn’t shake herself from the idea. Why? And surprisingly, the more she thought about it, the more interested in it she became. Almost as if she wanted him there at that game. Why?
Her alarm went off, dragging her fully out of sleep – although she had already been mostly awake. She leaned over and turned it off and sat up on the edge of her bed. Visions of him playing poker with his friends still played through her mind. Why? Maybe coffee would help. Yes, definitely coffee!
She got to her feet and trudged into the kitchen. The picture that he had colored so childishly last night at the restaurant, that was now taped to the front of her refrigerator, immediately caught her eye. She smiled at it… even as visions of him playing poker with the guys returned to her mind. Why was she so fixated on it?
She filled her coffee maker with grounds and added the water. Still thinking about him playing poker, she watched as the coffee began dripping into the pot below.

Chad pulled the first of his required thee morning bottles out of his refrigerator and headed back toward his lonely chair in the living room to drink it. Before he got there however, something odd caught his attention. There, taped to the wall, right in front of his chair where he couldn’t miss it, was another of the pictures he had colored last night in the restaurant. He stared at it in shock! Just looking at the childishly colored picture made him feel funny inside. His day had just barely started and already the new humiliations were coming at him. He was now more worried than ever about what the rest of the day might bring.
He sat down in his chair and automatically put the bottle to his lips. He stared at the picture for a while, then tried to look elsewhere and put it out of his mind, but since the picture was taped right in front of him, his eyes kept going straight back to it. Did she have to pick one of the ones where he was trying to color while drinking his bottle? Not only did the crayon marks look like scribbling, they strayed out of the lines in more places than he could count. Totally childish!
He was tempted to rip the picture down and throw it away, but since Mel had put it there, he figured he’d better not. He tried to turn his mind instead to the day ahead. It was Friday – thank goodness! Maybe! Tonight would be nail salon night. He looked down at the fingers of his hand that wasn’t holding his bottle. Pretty nails. He still thought the new length made his fingers look more feminine. Would Mel finally arrange to have them cut shorter again where they would be less in his way? Or not? He stared at the back of his hand and his fingers again. Pretty nails… pretty fingers. Much more feminine looking than they used to be… he thought. Maybe he should ask Mel to keep them that length. He did kind of like them. As difficult as they were and as humiliating as they were, they really weren’t all that difficult to manage at all. If he asked her, would Mel let him keep them that length? It seemed like lately she was changing the length every week. But if he asked her, would she just leave them alone this time? Did he dare ask?
As he dropped his hand, his eyes automatically focused on the crayon picture again. It was now the second of two things hung on his walls and unfortunately, the placement forced him to notice more the other item there – the framed copy of the bet contract. The contract was hung just a little bit to the side and about a foot above. Previously, his eyes had been able to ignore it, barely noticing it at all. But now, the placement of the new picture seemed to call all that much more attention to it. Both items made him feel a bit squeamish inside. And now, they both would be harder to ignore.
His bottle finished, he set it on the floor next to his chair and headed straight to the bathroom to begin getting cleaned up. He had a lot to do before he went over to Mel’s apartment. Get his bloated messy diapers off, shower, shave all over, get back into two diapers and plastic panties, do his hair, do his makeup, and figure out what he was going to wear for the rest of the day. All that, along with finishing two more baby bottles. The bottle he had just left behind would get picked up later and would be taken back to Mel, along with his next two bottles and the three empty bottles he had finished before he went to sleep last night. Ugh! Way too many baby bottles in his life!

Mel pulled on a pair of comfortable pants and an old soft top. Chad would be back in a little while, it was time to make breakfast for him – his baby cereal. The thought of it amused her as she carried her empty coffee cup back to the kitchen. She poured herself a fresh cup, took a sip, and began preparing his breakfast. As she stirred the creamy white baby cereal, her mind again went back to her question of the day. Why did she keep thinking about him playing poker with his friends? It made no sense! She got his tiny rubber coated baby spoon out along with his bib and removed the tray from his highchair. Everything was ready – early. But that was no problem. She turned the heat off under his cereal and poured it out into a bowl so it would be ready.
Picking up her coffee cup again, she leaned against the counter and stared at the crayon picture he had colored last night. She wondered how he felt about the one she had left for him last night. The pictures were really the perfect little item to show off to “friends.” In fact, she wondered if Sandy might like one. Sandy was overly interested in the baby side of him. Maybe the next time she and Sissy went out to a restaurant, she would have him color another one just for Sandy. She giggled at how she imagined he might feel if he had to carry the picture over to Sandy’s apartment and present it to her – like a child. Sandy, she knew, would love it!

Chad stared at his reflection in the full length mirror mounted to his closet door and turned a bit left then right to check his image. There was still one pair of pants left in his closet that he could have worn today if he wanted to, but they were even tighter than the pants he had worn on Wednesday. Which meant that there was no way he could ever hide his diapers when they got bloated. The pants were not an option to wear to work.
So today he was wearing another dress – another new dress. This time his black and white zebra print dress with the wide full skirt. The only real hints of any color were from the pink stones in his necklace and his ring. He was sure that the ladies at work were going to love it. Not only did he think it looked really nice, if not a bit dressy, but the fact that it was another new outfit that he hadn’t worn before would certainly get their attention too. He suddenly realized what he had been thinking. How odd was it that he would suddenly want their attention over the clothes he was wearing. Previously, he had been more concerned with them not noticing. How very odd indeed!
Ready to go, he quickly gathered up all the baby bottles from last night and this morning and dumped them into an old plastic grocery bag. He grabbed his diaper bag and his purse and headed out the door.

Mel opened her door to his knock and blinked a few times in surprise as she watched him curtsey and give his usual morning greeting. She had expected him to be wearing pants today not a dress. Not only that, but the dress looked a bit more formal on him today than she remembered from seeing it in the store last week. “Good morning, Sissy,” she returned as she stood back out of the way to let him in.
She took the bag of empty bottles from him and waited till he had set his purse and diaper bag down. Then she really looked him over carefully. “You surprised me today. I expected that you would be wearing pants again. You only have two pair.”
“I don’t dare,” he replied, careful to use his sissy voice. “The pair I wore before was so tight that my diapers started to bulge the crotch out too much when they got bloated. It was too noticeable. The pair I have left is even tighter. There’s no way I could hide what I’m wearing underneath.”
“So you chose something with a skirt instead?”
“Yes. It’s safer that way. I hope you don’t mind.”
“I don’t mind at all. What you wear to work is up to you. As long as it’s in your closet that is. That dress does look really nice, by the way.”
“Thanks,” Chad replied. “I’m hoping that will be the general consensus when I get to work.”
Mel almost laughed. “Don’t worry. I’m sure you’ll be quite a hit.” But her next thoughts ran directly to the Robin woman. Would she like the way he looked in this dress a little too much? “Breakfast time, Sissy. Up in your highchair.”
A few minutes later, Mel was leaning against her counter watching him make a total fool of himself trying to eat his breakfast with the tiny little baby spoon. The bottle of juice he was drinking didn’t help his situation either. No matter how hard he tried, he just looked like… a baby! A big grown up baby for sure, but a baby none the less.
But as she watched him, her mind suddenly began overlaying images of him dealing cards out on his highchair tray. She shook her head to clear it. Why couldn’t she get it out of her head? It was stupid?
“Mistress?” Chad’s voice interrupted her crazy thoughts – banishing them for a few moments.
“Yes, Sissy?”
He held up one of his messy hands as if showing it off. “Is there any chance I can keep the length of my nails like they are now when we go for our appointment tonight?”
His question surprised her totally. First he seemed to be fairly excited about showing off the dress he was wearing, and now he wanted to keep his longer length nails? “You don’t want them cut a bit shorter?”
Chad looked at the nails on one of his hands again for a moment. He shook his head. “I think I like them this length. Maybe it’s just my imagination, but I think they make my hands look more feminine.”
Again, Mel was surprised by what he had just said. “You can if you want, Sissy. Tell you what, I’ll leave that up to you tonight. You can tell your nail tech exactly what you want. In fact, you can pick the color too.”
Pick the color? Chad wasn’t sure he was ready to do that. It would be like taking too much responsibility in the process. He wouldn’t have her wishes to stand behind. It would be like he was feminizing himself. “Uh… maybe I should let you decide,” he replied.
“No, I think it’s past time that you started thinking about some of these things yourself.”
As Chad resumed eating again, he was more troubled about what he would have to do at the nail salon than he thought he would be. All he had wanted was to keep the pretty nail length he currently had. Now he would have to be making too many decisions. And he had no doubt that if Mel wasn’t happy with any of his choices, then next week she would find some way to make him miserable about it – like she had done when she had the super long nails put on him a few weeks ago. That had been really difficult to deal with.
As Mel went back to drinking her coffee again, she found herself amused by his strange request. Imagine, he didn’t want his nails cut shorter this time. How strange!
A little while later, she watched as he headed out the door for work, purse slung over the crook of one arm and his freshly stocked diaper bag over his other shoulder. She headed back to her bedroom to begin getting ready for work. But the thought of him playing poker with his friends intruded into her mind once again. Why couldn’t she get rid of the thought? There was no way she was going to let him run off to act the least bit like a man again. So why was she suddenly considering it?