The Bet - Chapter 16 (Sunday – week 3 Part 2)

The Bet
by Karen Singer

Chapter 16 (Sunday – week 3 Part 2)

As Chad rode with Mel toward the grocery store, he stretched and rubbed his face. After all the makeup they had put on him then taken off again, it tingled a bit. He loved the feeling of being out for a change without any makeup. But now he wished he could get rid of the ever-present perfume smell. There was just no winning anymore. And worse, the darn perfume was making him horny. Mostly, while he knew how he was dressed, he never looked at himself so he didn’t think about it as much, but the smell of the perfume, especially when it was coupled with the occasional sight of his pink fingernails, sent electric thrills throughout his entire body. He just prayed his chastity device wouldn’t start hurting him again.
Once again, he followed Mel into the crowded store. Was there anyone there who would remember him from last week? Probably. He was sure that last week he had been a sight that was hard to forget. But how about this week? Yeah, he was still going to be hard to forget. But hopefully, not quite as bad.
As he grabbed a shopping cart and put his purse into the child seat of the basket, he paused for a minute to pull his grocery list out. He didn’t really need it, but he knew that Mel would want to see him using it. Mel was waiting for him. He pushed his cart up to where she was waiting. She put her own purse into the cart next to his.
Last week, he had timidly followed her around the store while she selected things to put into the cart. This time it was different. This time, it was more like two friends shopping together. Anything that Mel thought she might like, she put into the cart, but mostly, he was the one picking up things that he thought they might need. On one aisle, he picked up several kitchen utensils that he thought might be nice to have. She didn’t protest at all. It was the same when they came to the spices, he added quite a few that he thought of as basic to every kitchen. Obviously, she didn’t cook at all or she would have already had most of them.
He noticed a difference in the people around him too. While he was certainly getting lots of interested looks, for the most part he didn’t think he was getting nearly as many as he had last week. What a difference not wearing a skirt could make! He was very grateful. He had done enough shopping with Mel now that he was starting to become at least a little more comfortable with his silly image in public. At least to a point. But the thought that he was becoming more used to it also frightened him a bit.
While they had been buying makeup earlier, he had never once noticed that he was holding back from peeing till they were leaving the store. Now, as they reached the last aisle of the grocery store, he began to think ahead to the checkout counter. Would she ask if he had to pee again? He wasn’t sure, but just to be safe, he let himself wet his diapers one more time while they were still shopping. He noticed that now he had to make himself relax to do it. Quite a difference from before, and he was glad. Especially since Mel would never know.
“Do you have to pee, Sissy?” Mel asked as the clerk was ringing up their sale. Chad was too aware of the people around them suddenly listening more intently.
“No, Mistress,” he replied as he dropped a quick curtsey. He heard a few noises of laughter and surprise from the people around him. “I had to do it a few minutes ago.”
But Mel wasn’t letting him off so easily. “You did what a few minutes ago?”
“I wet my diapers a few minutes ago.” He replied with one more curtsey. Fortunately, Mel looked satisfied as she pulled her wallet out. He was especially glad since there were definite chuckles from the people around them. Chad found himself wishing for lots of makeup again so it could hide how red he knew his face had to be.

When they got home, Chad had to carry all the groceries up to Mel’s apartment by himself while she busied herself with work on her laptop. He wouldn’t have minded it so much, but going up and down the stairs so many times in his heels got tiresome after a while. In fact, he had been on his feet so much already that his feet were starting to ache just from standing.
After he put the groceries away, he was a bit surprised that Mel didn’t want him to change into his uniform. Instead, she had him make both of them a small salad for lunch. Chad’s naturally went into the refrigerator while she ate… and he once again had to stand in the corner. The longer he stood facing the wall, the more he realized he was concentrating on his feet and how his shoes were beginning to hurt. Why had he thought these heels were more comfortable? They didn’t seem that way anymore. He yearned to take his shoes off for just a few seconds and stretch his feet. But every time he even fidgeted just a little, Mel yelled at him to stand still.
Finally, he heard her getting up from the table. She walked into the room where he was and stood closely behind him. “Are your feet getting tired in those shoes?” she asked quietly.
“Yes, Mistress,” he said into the corner that was all too close to his face.
“You like wearing heels like a girl, don’t you.”
“Yes, Mistress.”
“But they’re starting to hurt now, aren’t they.”
“Yes, Mistress.”
“Don’t worry sissy. You just need to get used to wearing them more. I’m glad they’re hurting you. Think about this now while they’re hurting you… think about how someday your feet are going to hurt, but they’re only going to hurt when you’re not wearing high heels. Won’t that be fun? It’s not very difficult you know. All we have to do is make you wear them all the time. Then eventually your feet and leg muscles adjust, and bingo… you can’t go without heels anymore. Wouldn’t you like that?
“It’s kind of just like you’re learning to wet yourself while you’re sleeping now, isn’t it? And I’ll bet you’re learning that really well too, aren’t you?”
Chad’s only reply was to squirm in his corner a bit because her words sent chills throughout his body. He realized that what she had just said was all too true. He knew that he wasn’t always waking up every time he had to go during the night anymore.
“Isn’t it better now, being able to sleep through your wetting? Doesn’t it make you happy that you don’t have to wake up anymore? Just think, soon it will be just as easy for you to wear high heels all the time too. I know that you’d like that. Wouldn’t you? That is… if I decide to do that to you. It’s not up to you now, is it? Everything to do with you is completely up to me and what I want. I don’t think you’ve quite got that point yet, but we’re making progress. Oh yes, we’re definitely making progress.
“Now I want you to go and sit on the kitchen floor with your lunch. And the whole time your feet are hurting today, think about what I just said. Wouldn’t it be wonderful if your heels didn’t hurt you? Maybe I should have you beg me to do that to you. What do you think? Now go! Eat your lunch!”
Chad was mentally shuddering at Mel’s words as he left his corner and went into the kitchen. The very thought of what she had said scared him… but at the same time it was thrilling him beyond belief. He could feel the tiny pinpricks of his chastity device digging in ever so slightly, but fortunately, that’s as bad as they got as he willfully controlled himself. And his bigger problem was that he had to keep controlling himself, because just as she suggested, he constantly thought about what she had said since his feet constantly hurt. He couldn’t help it.

Chad had just started cleaning the dishes from lunch when Mel’s phone rang. He heard her answering it, but he couldn’t hear anything else that she said into the phone.
“Ok, Sissy. Sandy’s waiting for us. Stop what you’re doing and let’s go.”
Chad turned the water at the sink off quickly and dried his hands. Mel was already waiting for him in the living room. “Get your purse and your new makeup, Sissy. We’re going to their place.” Chad did as he was told. Fortunately all his new makeup was all in one plastic bag that he had set by the door. He was just slightly surprised that they were going over to Cassie and Sandy’s apartment instead of them coming here. He still had dinner to make later.
Sandy opened their door before Mel had even finished knocking. “Come in, come in,” she said quickly. She seemed way too excited for Chad’s comfort. He noticed that she had set up a large lighted makeup mirror on her kitchen table. It looked like she had been waiting for him for a while now.
Sandy took his bag of new makeup from him and began putting it all out on the table. “You may as well get your other stuff out now,” she told him, “we’re going to need it eventually anyway.”
As he opened his purse and again started pulling the makeup out, he tried to figure out how he really felt about it. Yes he was excited. Yes he was scared. Yes he felt humiliated. But yes, he was also interested too. Did that make him a sissy? He didn’t have to answer that question. “Where’s your moisturizer?” Sandy asked.
“It’s still home in my bathroom.”
“Well go get it girl. We’re not going to do this without it!”
Chad reluctantly went back to his apartment to get the moisturizer that he had been shaving with every day. Why should he need it? It wasn’t doing him any good as far as he could see… other than to make shaving his face easier every day.
Once he was back inside Sandy’s apartment, Chad was very glad when she told him to sit down in front of the mirror. Now, maybe his feet would stop hurting for a while and he could stop thinking about being only able to wear high heels - forever.
“Ok,” Sandy started. “I’m going to do everything to half your face, and you’re going to do the other half. Got it?”
Chad nodded. It seemed simple enough – he hoped.
She started with his moisturizer and just as she said she would, applied it thoroughly to half of his face. Then she handed it to him. “Ok, your turn.” She watched him for a few seconds. “Not so much. You don’t need much, just a little. Then spread it out more.” She produced a wet washcloth and let him wipe his face clean. “Now do your whole face this time, only don’t use so much.”
When she was satisfied with the way he was doing his moisturizer, she moved on to the concealing makeup. It was a while before Chad realized that while what he was doing should have been humiliating, it really wasn’t. While Sandy was working with him, she wasn’t trying to humiliate him in any way. None of the women were. They were all sitting around talking and offering suggestions and comments and having a good time. Girl-talk. And once Chad realized it, he was thrilled by it. It was a small thing, but it felt nice. It was mildly fun. Guys talked together all the time, but half the time it was boasting about this or that. With women it was different. He might be a sissy, but for once, he was enjoying himself. If only the feeling could last forever.
But unfortunately everything got interrupted when Mel’s cell phone rang. “Hello?” she said into her phone. “Again?... “Yeah, I’ll take care of it… Just wait for me, don’t do anything till I get there!” She hung up. “I’ve got to go. Very old client… very stupid kid.”
“Aww,” Cassie replied. “We were having a good time. Does Sissy have to go too?”
Mel looked at her watch. “It’s probably best if he does go. He still has to cook our dinner later and there’s a lot of cleaning he has to get done first!”
“That reminds me,” Cassie said, “what time do you want us there?”
Mel looked at her watch again. “I don’t know how long this will take. Hopefully not too long. Let’s plan for seven thirty, ok?”
“Sounds great!” Sandy replied.
“I can’t wait,” Cassie agreed.
Chad was the only one who wasn’t sure.
When Mel and Chad were outside alone again, she stopped to talk to him. “Sissy, I have to leave right away. I’m counting on you to make everything perfect tonight.”
“I’ll try,” Chad replied honestly.
“Good. Don’t forget to be in your uniform before then but don’t get it dirty. I want you looking perfect. Oh, and see what more you can do with your makeup before then too. Now I gotta go. See you later!” And with that, she was running down the stairs and Chad was left on his own. Only this time, he had a lot of work to do before she got back.
As he opened Mel’s door, he thought about his shoes. He had been sitting down for a long time now and his feet didn’t hurt so much. But he knew they probably would start hurting again very soon. Did he dare take his shoes off for a while? Once again, even though his feet weren’t hurting, the fantasy of being unable to wear anything but high heels went through his mind. And once again, the tiny pinpricks from his chastity device were just barely there. But the fantasy was powerful enough to make him keep his heels on and not take them off.

Mel’s apartment didn’t really need much cleaning. He had done enough of that that he didn’t really have to do hardly anything. After he had done some basic prep work for dinner, he started on Mel’s laundry, which wasn’t all that much. While that was in the washer, he went back to his apartment and got his laundry too. He was especially worried about washing the pants he had wet yesterday morning.
He found that he was actually happy as he worked around her apartment. Occasionally he did a few things towards the dinner he was preparing and at other times he straightened up the house or folded clothes. Even with Mel gone, he was really enjoying it. And as much as his heels eventually started to hurt, the fantasy kept him interested. Even when he found himself sitting more and more often to rest his feet.
When all of his own laundry was done, he took it home and put the things that needed to be hung up into his closet again. Then he went back to her apartment and looked around. All her laundry was done. Her apartment was clean. The table was set. He looked at her clock. It was time to start the final cooking of dinner. Everything was going perfectly.

Mel stared across the table at the punk kid in front of him. God the kid was stupid. This was the second time in the last few months that he had been caught with drugs. Bad ones. The problem was that his parents were rich and he didn’t care about anything. She knew his parents though, they were good people. Real good. They had been clients of hers for a very long time. One of her first clients in fact. She owed them a lot.
“Wait here, and don’t… say… anything!” she ordered.
He held up the chain that was cuffed from the table to his wrist. “Like where the hell am I gonna go?” he asked smartly.
She shook her head and left the room. Stupid kid! His parents were waiting anxiously out in the hall. She hated having to talk to them. She shook her head as she walked up to them. “I’m sorry,” she said. “He was really stupid this time.”
“Isn’t there anything you can do?” his father asked. She could see the pleading look on his mother’s face.
“Look,” she told them. “Let me talk to the detective again. I’ll see if there’s anything at all that can be worked out. But I’ve got to warn you, it doesn’t look real hopeful. He actually seems proud of what he did!”
“Anything you can do we’d appreciate,” his mother told her.
Mel nodded to them both and walked down the hall and went into one of the offices.
Detective William Grey was sitting at his desk pounding on his keyboard with remarkable speed. She plopped herself down heavily in the chair in front of his desk. “Just a sec…” he said as he kept typing furiously. He hit one final key then clicked something with his mouse. “There! Done!” Finally he turned toward her. “Hi Mel. Long time no see.”
“Yeah,” she laughed. “Like it’s been almost two days now!” The truth was that they ran into each other frequently. Heck, she had even dated him a couple of times, but he really wasn’t the type that she was interested in. In fact, all of their dates had left her flat. Too much business – among other problems.
“So what do you think?” he asked, referring to the problem kid in the other room.
“What a jerk! But he’s my client and he’s got good parents. It’s definitely not their fault. All the other kids in the family are just fine… all except him!”
“That doesn’t help him though.”
“No, it doesn’t.” She looked at him for a few minutes. “Look, I’m betting you really don’t want to keep this guy. Is there something we can work out? Like maybe where he’s getting his stuff from?”
He smiled. “You’ve been hanging around here too long. Let me see if I can reach the DA.”
She sat quietly and waited while he talked on the telephone. She tried to grasp as much of his conversation as she could, but she couldn’t tell everything. He was a good looking guy. Big and confident. Too confident for her tastes though. Still… If she wasn’t so hung up on Sissy just then she might consider asking him out. Yesterday had been kind of an eye-opener for her. It wasn’t till then that she had realized how pitiful her social life really was. But that was part of the point. He was big and confident, and Sissy was… well… a sissy! And right now, Sissy was winning out – big time.
He hung up the phone. “Ok, there’s a couple of things here. First of all, he’s got to spill everything… and… we’ve got to make a decent bust on it.”
She nodded. “That’s good, what else?”
“And,” he continued, “you’ve got to let me take you to dinner.”
She burst out laughing. “Oh Will! You’re too much!”
“I’m serious! I don’t need to let this kid go. We’ve got enough on him now, and anything else we get from this is probably going to be small potatoes too.”
“That’s blackmail,” she replied, still laughing.
“That it is! But I’m sticking to it!”
She still couldn’t believe it, and she was still half laughing. “Ok, deal! Now let me talk to him again and see what we can get.”
Before she could get to the door again he said, “Oh and Mel… when we go out… don’t dress like you usually do when you’re not working.”
Her eyes went wide. “What? You want me to wear a dress?”
“Something like that.” He sat back in his chair and laced his hands behind his head with a very satisfied look on his face.
Mel shook her head as she went out. Way too confident and manipulative. No wonder she wasn’t that keen on the guy. And she had just agreed to a date with him? Ugh! Oh, and he wanted her to dress up too? What would be next?