The Bet - Chapter 43 (Saturday – week 6 Part 7 of 8)

The Bet
by Karen Singer

Chapter 43 (Saturday – week 6 Part 7 of 8)

Before going back to Mel’s apartment, Chad washed his face and hands. He was a total mess from all the baby food that had coated him. His pillow was a total mess too since most of what was on his face was now transferred there. As he was drying his face, Mel walked in to his bathroom and handed him another baby bottle from the few that were still in his refrigerator – bottle number twelve for the day now. Was she trying to set a record or something?
Under her watchful eye, he removed the dress he was wearing. “What do you want me to wear,” he asked, finally speaking in his sissy voice. But even then, his voice was still full of the self–pity he felt.
But Mel was staring at him. She couldn’t get him dressed to go out yet. Not yet. She had forgotten something. She opened his closet door. “What do you want to wear?” she asked.
That was a bad question. Chad didn’t even want to think about all his men’s clothing that was now… who knew where. Certainly not in his apartment, that was for sure. “I don’t know,” he replied with no enthusiasm at all.
Mel started going through the clothes in his closet. Almost all skirts. He had a few pairs of slacks there but they wouldn’t be good for what was needed now. She briefly considered his zebra print dress, but decided against that too. Finally, she pulled a brightly patterned skirt out and looked at it. Just the thing! She chose a bright red top to go with it. She held them up for him to see. “Something colorful to brighten your mood,” she said lightly, trying to raise his spirits.
Chad looked at the outfit she had chosen for him and just shrugged. The way he felt just then, one thing was as good as another. He reached to take them from her, but she held onto them instead.
“We need to carry these back to my place. You can get dressed there.”
Chad just shrugged his shoulders again. He didn’t really care.
Mel could see that bringing him out of the funk he was in was going to be harder than she thought. Unfortunately, she completely understood why he felt that way and couldn’t blame him in the least. She tried to smile as she said, “Just grab your waist cincher and a bra to take with you and we’ll go back to my place.” While he was grabbing what he needed, she went back to his closet and grabbed a pair of strappy shoes for him to wear.
Chad pulled a fresh bra out of his cardboard dresser and found one of his waist cinchers. No girdle at least – which was both good and bad. It was good because he would be at least a little more comfortable. But it was also bad because it meant that she was going to keep him in only one diaper with a time limit to make it leak. He didn’t know how much over his latest limit he was now. He just hoped that Mel wouldn’t care for once.
“Drink some of your bottle,” Mel ordered before they left his apartment. “You need to keep peeing.”
Chad had felt himself peeing a few times since they had left Sandy’s apartment. But he had only barely noticed it. Other things had been more important and he peed so much now that there was no reason to take much more notice than he did. He put the bottle to his lips and took several long drinks before Mel was satisfied and led the way back to her place.
Mel went straight to her bedroom where she hung the clothes she had selected for him on the closet doorknob. She found the breast forms that needed to be glued back onto him and held them up. “Do I need to tie you up to do this?” she asked.
Chad stared at the breast forms. For some reason, they looked so much bigger in her hands today than usual. He could already feel the weight of them on his chest. He shook his head but didn’t answer any other way.
“Climb up on the bed then and let’s get this over with.”
Chad laid down on her bed while she coated the breasts with the glue and started it drying. It took a few minutes for it to get tacky enough, then she climbed up on top of him and carefully lined one of them up where she wanted it to go and pressed down on it, sealing it to him. “Hold this down while I do the other one,” she told him.
Chad put his hand on the breast that was once again glued to his chest and pushed down. The darn thing felt so damn real! He watched as Mel lined up the other one and pressed that into place as well. He automatically brought his other hand up to hold that in place too.
Mel smiled and climbed off of him. Hopefully the things would stay right where they were. They hadn’t failed yet! “Keep holding them and sit up,” she instructed as she found his bra.
A minute later, Chad slipped off of her bed, his bra now holding the newly glued breast forms in place to make sure the glue was completely dry and they wouldn’t fall off. As he took the first few steps away from her bed, he realized how normal it felt now to have them back again – more normal than without them. That thought sent a small shiver through his spine. And a small tingle elsewhere. He grabbed his waist cincher to start putting that on, but she stopped him before he even got started with it.
“Drink some more of your bottle,” she instructed. “You’re falling behind with it.”
Falling behind? He wasn’t exactly sure what she meant. Besides he had already finished more bottles today than usual. But he grabbed his bottle and took another long drink before he finally started fastening his waist cincher.
Mel went to her bathroom and grabbed another diaper for him while he was putting his waist cincher on. She brought it back to the bedroom and laid it out on the floor. Then she found one of the jars of suppositories she kept for him and set that out too. She saw him glance with disgust at the jar as he finished what he was doing. Good!
Baby bottle in hand, Chad laid down on the floor to get his diaper changed. He automatically put the bottle to his mouth as he felt her unfastening his diaper – that was very wet but hadn’t leaked yet. She had made no mention of it leaking – fortunately. He felt her grabbing his legs and pushing them up so she could get at his backside with her stupid suppository. Even today… even after what she had done to him earlier… even when he was feeling more depressed than he had ever felt in his life, she wouldn’t let him go without one. Damn her!
Mel shoved his legs up high and reached into the jar, but she only pretended to pull one of the suppositories out. Just as she only pretended to put it up inside of him. She could tell by watching him that he didn’t know the difference – which was just what she hoped. Finished, she gently let his legs back down and tightly fastened the fresh diaper around him. “There,” she said sounding somewhat satisfied. “You’re all set,” she glanced at the clock on her nightstand. “An hour and forty-five minutes, Sissy. Better keep drinking that thing.”
Chad didn’t have to be told. In fact, the moment she had said it, he felt himself releasing a tiny bit of pee. That seemed to be the way it was going with him today. A tiny bit at a time, but it happened every few minutes – as far as he knew. At times he had been too busy to notice it today. Instead of getting up to get dressed, he laid right where he was and sucked on the bottle for a few minutes. Fortunately, Mel didn’t seem to mind. And the bottle? Well, he was kind of enjoying sucking on it today. It felt good – despite Mel’s lousy tea that he was drinking from it.

The store that Mel took him to was the same one where he had bought most of his clothes – most of his new clothes that is – his female clothes. He and Mel walked side by side like old friends as they headed back to the dress section. Since they had left the house, he had said almost nothing and mostly listened to Mel’s light-hearted comments. He knew she was trying to bring him out of his depressed state, but it wasn’t working very well. How can you feel anything but depressed when your entire life was about to be over and everyone in the world was going to know your deepest, most horrid secrets?
“What kind of dresses do you think they’ll like?” Mel asked as they reached the dress section.”
“I don’t know,” Chad replied. “I never thought about it.”
“Well, do you think Ray would like me better in something really short or something really low cut? How about color, do you know if he’s partial to any in particular?”
Chad was surprised to realize that she was talking about a dress for her, not what he would be wearing for Derek. “If I know Ray, it doesn’t matter what you’re wearing. You could be wearing… a plastic bag and he’d be interested.”
Mel giggled, but from what little she had seen of Ray so far, she knew he was right. “How about Derek? What do you think he’ll like?”
Derek! That was the problem. He had to go out on a date with his best friend. “Not what I wore to the poker game!”
Mel giggled again. “I don’t know. He might!”
“Can I help you find something?”
Mel turned around to see the saleswoman who had helped them so many times in the past. She smiled. “We have dates!”
The saleswoman looked shocked as she stared briefly at Sissy. But she recovered quickly. “I see. What did you have in mind?”
“I don’t know,” Mel replied. “Something really…” An image of Derek came to her mind instead of Ray. “Nice!” she finished. “For both of us.”
The saleswoman just nodded. “Shall we take care of your… maid first?”
Chad was surprised that she had referred to him that way. He wasn’t even wearing his maid’s uniform today… although he had in the past.
The saleswoman led them over to several other racks where she kept glancing back and forth between Sissy and the clothes. She pulled several dresses out and held them up asking each time what they thought about them. Mel seemed to like most of her suggestions and Chad wound up holding more and more dresses as they kept looking. Finally, the saleswoman decided that they had found enough. “Would you like to try some of those on now and see if any are good enough?” she suggested.
Chad carried half a dozen dresses into the changing room. He was going to be trying on dresses again – in the store. The thought didn’t bring as much humiliation to him as it used to. Maybe because of the depression he still felt. It felt more like he was only going through the motions as he took his clothes off and took the first dress off of the hanger. It was a bright sky blue dress with a full skirt and a fancy gathering right in the middle under the breasts with a blue and white rhinestone decoration on top of it. He slipped the dress on. The material felt somewhat thick, but at the same time, very soft and light. Once zipped, it felt very comfortable. He allowed himself to feel pleasure despite how depressed he still was. He looked at himself in the mirror in the changing room. What he saw, he liked - surprisingly. Maybe Mel would let him buy it if she decided on one of the other dresses instead. Plucking up his courage – less than he needed previous times, he stepped out to show them.
Mel and the saleswoman were chatting while they waited for him to come out. When he did finally show, they both stared at him with some surprise. The blue dress was fairly low cut, but the design didn’t seem to show any of his bra – so his breast forms wouldn’t be a problem. The gathering below his breasts was set off with a pretty rhinestone decoration that nicely accented the design as it tapered down to his slim waist. And the full knee-length skirt hid any evidence of the diapers he would be wearing underneath. But most of all… it looked good on him! Really good!
“Oh my!” the saleswoman exclaimed softly. “He’s certainly come a long way since you first started bringing him in. Hasn’t he.”
Mel nodded as she continued to take him in. “Don’t bother trying any more on,” she told him. “We’re buying that one!”
Chad was actually pleased. He liked the dress. It was… comfortable. But would Derek like him in it? He was shocked that he would even think such a thought!
Mel turned to the saleswoman. “We’ve got a real problem now, because I’m not leaving here till I have something that looks better than that!”
As quickly as Chad’s dress shopping was over with, Mel’s shopping seemed to drag on that much longer as she looked at dress after dress. Chad held several in his hands for her as they searched for others, only to have some of them taken away to be replaced by still more. Three times she went into the dressing rooms with a number of dresses, most of which she discarded as not good enough.
As he waited, Chad caught himself peeing several times – barely. Mostly, he was only just aware of it as he was finishing. He was still amazed that it could happen that way. Actually, he figured he was mostly catching himself doing it only because he wasn’t doing much of anything else – except waiting – and holding dresses.
Finally, Mel decided on three to take home with her. She would choose which one to wear for the date when the time came. The rest… well, she supposed she might be able to wear them to the office – maybe, but it was doubtful. They really weren’t the kind of thing to present a very professional image to clients – not her profession at least.
After Mel had selected her dresses, Chad hoped they would be going home, but Mel only looked at him with seeming surprise on her face. “We can’t go yet. You need a different purse to go with that dress. You can’t very well carry that thing with you tomorrow night!”
Chad looked down at his purse. He had been carrying it everywhere he went for quite a while now. It served his needs very well. But he supposed she was right that the dark red alligator pattern didn’t really go very well with his bright blue dress. While the saleswoman carried the dresses up to the registers to hold for them, they went in search of a new purse for him to carry.
Mel realized he was still mostly going through the motions with her. But he was responding – somewhat. She could tell that he at least liked the blue dress they had found for him, which was a good sign. It really was nice. She briefly wondered if it would fit her and if she could borrow it sometime. Then she realized that it was a stupid thought. She knew it would fit her… and if she wanted to wear it, then she could! He didn’t have any say in the matter at all – even now! But of course, for now, she needed to go a bit easier on him. The state his mind was in wasn’t the best, although she was beginning to tire of it.
Chad stared almost blankly at the colorful display of purses all around him. He was supposed to find one that would go with his dress for the date. But which one? He didn’t see any matching the sky blue color of his dress. The last time he had bought a purse, which was the only other time he had bought one, Mel had tried to get him to look at them and choose something practical. Well, he supposed he had a better idea now of what he needed. Something that would hold a lot of junk while still having some organization to it. He hated to think about it, but there was a lot of loose junk in his purse right now. Sometimes he had to fight past it to find anything. Of course, it was perfect for things like loose change. He grabbed one hanging on a hook and opened it to look inside. It was certainly big enough. In fact it was bigger than the one he was currently carrying. But did the brown leather go with his dress? Probably not. He put it back and continued to stare at the colorful display. But in his present state, picking something out was only barely interesting. He was having a hard time focusing on exactly what he would need.
Mel had seen him look at the larger purse – totally inappropriate for what was needed tomorrow night. The expression on his face still hadn’t changed much – it was mostly blank! She decided to step in and help. “Can I make a suggestion?” She saw him just shrug. Again, no real verbal response or even much of a sign that he cared. She had to break him out of it. He had shown signs of life, but very few. She walked further away from where they were to a shelf and picked up a black patent clutch purse. It looked perfect. “Here,” she said as she held it up for him. “This would go very well. What do you think?”
Chad took a closer look at the purse. A clutch actually, because there was no strap or handle of any kind. The black patent leather fabric was somehow pulled, creating wrinkles on the front that were gathered near one end. The top of the gathering was set off by a pretty white rhinestone decoration that looked like two leaves stuck back to back. It was… pretty. And he knew it would go very well with his dress. He took it from Mel for a closer look. It took him a moment to figure out how to open the thing. The clasp on top was very stiff but he finally got it. There were no compartments for organizing things inside and the whole thing seemed… small. “How am I supposed to fit my wallet in it?” he asked. “My cell phone too for that matter?” It’s awfully small.
“You don’t need your cell phone tomorrow night. Your wallet either. You can just throw your driver’s license and a little money in it. That and some makeup are all you’re going to need. And hopefully, just the makeup.”
Chad knew she was right. But would Derek actually pay for everything for him? He doubted it. Derek had no reason to. If he were a real woman – then maybe Derek would pay. In fact, he probably would! But not for him. Not for a… fake! But still, Mel was right. The clutch would go well with his dress, and who would know better about what was needed than a real woman. And there was no doubt that Mel was a real woman – real and a half! He nodded. “Okay,” he replied as he closed it and looked at the front again. It was kind of… pretty. And… very feminine. Something inside of him was pleased by that.
Mel noticed a spark of something in his eye as he looked at the clutch. A brief sign of life? She could only hope. “Good,” she said as she continued to watch him. “I think it’s pretty.”
Chad nodded. “Me too.” It was a bit hard to admit. “I like it.”
Mel smiled. Yes, he was definitely coming back to life. “Why don’t we go look at some shoes too,” she suggested.
Chad just shrugged. “Okay.” But there was a bit more life in his voice than before.