The Bet - Chapter 22 (Saturday – week 3 Part 3 of 6)

The Bet
by Karen Singer

Chapter 22 (Saturday – week 3 Part 3 of 6)

Chad pulled into his parking space. He got out of his car and grabbed the bags of personal care items he had bought at Target. Then he wrestled the mirror out of his back seat too. He still had to get the big packages of diapers in his trunk but they would have to wait for another trip. With his arms fully loaded he turned toward the stairs. That’s when he caught sight of Mel and Sandy leaning over the balcony railing together, watching him. “Just great!” he thought angrily. As if things aren’t bad enough.
He awkwardly carried the bag and big mirror up the stairs and turned toward his apartment. Mel and Sandy were watching him intently. He was suddenly startled by a loud wolf whistle that he quickly realized came from Sandy.
“Nice dress,” Sandy called from where she and Mel stood. “How ya doin’ gorgeous?”
With his arms still full, he sort of dropped an awkward curtsey to both of them. “Hi” he said simply. “Do you need me for anything, Mistress?”
“Not till later,” Mel replied. “Just don’t be late.”
Chad nodded and carefully leaned the mirror up against the wall so he could open his door. His nails as usual made the task take forever. He finally opened it and brought everything inside. Then he went right back down to his car and wrestled with the two big diaper bags and brought them upstairs too. All the while, Sandy and Mel watched him closely. He saw them talking between themselves about him, but he couldn’t hear what they were saying. He was also fairly sure he didn’t want to know.
Inside his apartment, he put everything down, then sat in his only chair and ate his lunch. When he was done, he struggled with the packaging around his new mirror and with a bit of effort, got it free of the box. He leaned it up against his closet door and finally got a better look at himself. He had very mixed feelings. In a way, he didn’t think he looked too bad, but at the same time, he still noticed instantly that he was a man in a dress. His shape was all wrong, along with a few other things. He might be thin, but he just wasn’t built like a female. It was encouraging, yet still very discouraging. No wonder people still noticed him when he was out shopping.
The closet door looked like the best place to hang the mirror, so he found the package of screws and clips to anchor it there. But then he realized that he didn’t own a screw driver anymore. All his tools were back in his old house… gone with the divorce. He searched for something else he could use, but he wasn’t having much luck. Finally, in desperation, he found a paper clip and a small pair of scissors in one of the boxes in his room. It was the best he could come up with.
He hadn’t always been the best handyman in the world, but he did get by. He opened the package of screws with the scissors and dumped them out on the floor next to his closet. He held the mirror in place and figured out where to put the bottom holding clip so it would bear the weight of the mirror as he mounted it. Then he put the mirror off to the side again and picked up the first holding clip and reached for a screw. Again and again he reached for one of the tiny screws, but it seemed that picking one up wasn’t going to be all that easy with his new fingernails getting in the way. He tried using just his nails, but that didn’t work. He tried using the sides of his fingers, but that didn’t help much either. He even tired using both hands, but when he finally got a screw up between his fingers, he found it almost impossible to get it turned the way he needed it to go.
Finally, through shear perseverance, he got a screw through the hole of the mirror’s holding clip and he placed it up against his closet door where he needed it. The paper clip was useless against the screw so he picked up his scissors again, but no matter how hard he tried, he couldn’t get the scissors to work as a screw driver. And when the screw accidentally slipped out of the clip and fell on the floor, he threw the scissors down in frustration. He needed a better tool! He needed shorter fingernails! This job was impossible!
Feeling dejected, he left everything right where it was and wandered into his kitchen. He noticed his pacifier on the counter there. He suddenly wanted it. He picked it up and put it directly into his mouth. He didn’t know why, but it felt good. Comforting in a way. He closed his eyes and took a deep breath to calm himself. How was he supposed to get through life with the stupid nails he had on his hands now? He only hoped that Mel would let him cut them before he went to work on Monday or he’d probably get fired for being totally unable to work! In fact, he was really surprised that he hadn’t been fired already.
As he stood there feeling sorry for himself, he suddenly felt the suppositories in his system go to work, just as they did every afternoon shortly after he ate. There was never any denying them at all and he didn’t even try. But halfway through it, he remembered that he hadn’t had any stuck up inside of him since last night. But then since he got them so often, he supposed that there was still a lot of their chemical left over in his system. It would probably take days to get rid of it all.

Mel checked the clock. It was almost time for Sissy to arrive. She thought again about how he had looked when she and Sandy had seen him coming home earlier. He had worn a dress, and a fairly dressy one at that. She was surprised that he hadn’t pulled something a bit more casual out of his closet. But they were his fantasies after all. And to think that just a few weeks ago she had faked calling the police to just get him out of her car while wearing a skirt. He had come a long way. She smiled at that thought. And there was still a much longer way to go.
His knock came a minute early, and she was glad. She opened the door to him.
“Hello, Mistress,” he said around the pacifier in his mouth as he dropped a quick curtsey in his uniform.
She stood back and smiled. “Hello, Sissy,” she replied as she held the door open wide and let him walk through.
Chad set his purse on the floor next to the small table she kept near her door then stood still while Mel looked him over carefully. He had made sure that his uniform was freshly pressed and his shoes were freshly shined. He had even redone his hair and makeup. As far as he knew, he looked perfect.
Mel walked all around him, thrilled at the sight of everything she was seeing. Yes, he really had come a long way. And now it was time to take things a bit further. “Come into the bedroom with me now, Sissy, and take your dress off.”
Chad was a bit surprised by the order, but not all that surprised. He followed her into her bedroom and removed the apron from his uniform. Then he began trying to grab the zipper at the back of his dress. He had struggled a long time just to get it up, and now getting it down was proving to be just as much of a problem.
Mel was about to open her closet door, when she stopped and saw him struggling with his zipper. She stood there for a few moments, just because she was so amused by watching his plight. But at the rate he was going, it was going to take him too long to get the dress off. “Here, let me help you,” she offered.
Chad immediately stopped what he was doing and turned his back to her. She walked up and quickly pulled the zipper all the way down. “Thank you, Mistress,” he said quickly. “Doing anything at all with these nails is impossible!”
Mel left him to remove the dress the rest of the way by himself. She opened her closet and pulled out the box that held his new breast forms. She carried the whole box out and placed it on her bed. She walked up to Sissy who was now standing and waiting for her. She grabbed the pantyhose that he had been using to stuff the bra cups of his girdle and pulled them out, leaving him flat-chested once again.
As she removed his padding though, she noticed that his girdle didn’t fit quite as tightly as it used to. She pulled on it a bit here and there to test it. “I know you’ve lost weight,” she said, “but I hadn’t realized you’ve lost so much. It doesn’t fit as tightly as it used to. Of course you wear them pretty much all the time and it’s probably stretched out a bit too. We should have gotten you a few more when we bought them.”
“It’s still plenty tight,” Chad replied. “Just not as bad as it used to be. I’m just grateful that it seems to hide my diapers so well – including the smell.”
Mel nodded, “Yes, it’s worked out very well in ways I never thought of.”
Chad had been surprised when Mel removed his breast padding. But now as Mel went back toward her bed, his attention was even more focused on the box that was there. And when she opened it and pulled out a very realistic looking breast and turned towards him with it, he felt his knees quaking and the elephants returning to romp around in his stomach. He couldn’t believe how big the darn thing looked, not to mention how real.
He forced himself to stand very still while Mel pulled out the right side cup of his girdle and forced the breast form into it. Whatever the thing was made of, it felt all too strange up against his bare skin. He had to endure Mel pushing hard on it to force it down into the bra cup of his girdle which wasn’t really big enough to hold it. When she was done, he could feel the weight of the thing pulling against his girdle. He could also feel how much tighter the top of his girdle was now. Way too tight.
Mel picked up the second breast form and began trying to work it into the other side of his girdle. The full C cup size of the forms were really too big for the B cup that his girdle was made for, but it would just have to do for now. They would stop and get him some new girdles later. He needed more anyway – along with a few other things now. When she was done, she stood back and surveyed her handiwork – and smiled. Yes, they were going to be great. “Perfect!” she declared happily.
Chad was still in shock. He brought his hands up and cupped his new breasts, pushing them up, trying to take some of the weight off of his shoulders. He looked at Mel. “They’re so heavy.”
Mel smiled at him. “What? Do you think that a woman’s breasts don’t weigh anything? I’m betting they weigh just about what they should!”
“But they’re so big!”
Mel shook her head. “No, not really. In fact they look perfect on you. A lot better than what you were creating before with the pantyhose. And they’re only a C cup. Not anything larger.” She looked at him wickedly. “Of course I can always send them back and get you some much bigger ones. I’ll bet you’d really like that! Wouldn’t you?”
Chad was still trying to recover from the shock of the new breasts as well as the weight of them. But one thing he knew for sure, he really didn’t want anything bigger. “No thank you, Mistress,” he replied quickly. “These are more than big enough for me.”
“Well, we’ll just have to wait and see about that then… for now! Ok, Sissy, get dressed again.”
Mel watched him pulling his dress back on. Even without it being zipped up in the back, she could see the improvement in the look of his chest. Just to make things go quicker, she zipped him up herself and retied his apron around him properly. Then she had him stand there to inspect him once again. She looked him over carefully and felt a surge of satisfaction. Yes, he was coming along really well now. She should have gotten him the breast forms much sooner. They really did make a difference. “Ok, Sissy. Time to go,” she declared as she quickly headed for her front door.
“Go?” Chad asked. But Mel was already out of the room and he had to hurry to catch up. “Go, Mistress? Where?”
“Shopping of course,” Mel replied as she picked up her purse. “We need to get you a few things now.”
Chad wasn’t at all happy about having to go out shopping again – and now he was dressed like a maid! But Mel was already out the door and wasn’t even waiting for him. He quickly grabbed his purse and closed her door behind him as he went out. He hurried to catch up to her. “What kind of things?” he asked, fully concerned about it.
Mel just laughed a bit. “You’ll see.”
As they drove along the road, Chad remembered how humiliated he had felt about wearing a dress while he was shopping earlier that morning. Now he was out with Mel while dressed as her maid. How much more humiliating can something get?

Her first stop surprised him completely, although he realized he shouldn’t have been surprised at all. She pulled into the parking lot of the store where she had bought him the maid’s uniform he was wearing now. He meekly followed her inside, wishing he could stay invisible. What he realized in doing it so meekly though, was that he was probably acting more like a proper maid that way. Well, maybe that was for the best. He was her maid – for now. This bet wasn’t over with yet!
The store was a lot more crowded this time than the last time he had been in there, a fact that made him very uncomfortable. Mel didn’t even seem to notice or care. She waited patiently near the checkout counter while the saleswoman finished with another customer. Chad waited near her but a step behind. Finally the other customer left and the saleswoman looked up at Mel. Her glance quickly included Chad too, but she immediately focused her attention strictly on Mel – for a moment. Looking startled, she looked again at Chad, only a lot more closely. Chad had that old feeling of wanting the floor to open up and swallow him again. Finally, the woman looked back at Mel. “May I help you?”
“Yes please,” Mel replied like there was nothing out of the ordinary there at all. “We need a few more dresses for my maid here.”
This time, the woman looked harder at Chad. “That’s one of our dresses she… I mean he… I mean your maid is wearing now, isn’t it?”
“Yes,” Mel replied. “We got it here.”
“Do you want something similar?”
“I’d like two more of the same dress, if possible.”
“That’s no problem,” the saleswoman answered. “Do you want to go back with me, or wait here?”
“We can wait here,” Mel replied. “Oh, and two more aprons like that too.”
“Of course,” the woman replied. “What size dress?”
“Ten please.”
The woman left the register and walked toward the back. Chad was grateful that he didn’t have to go with her and walk through the whole store, the place was fairly busy. But a few minutes later, he was a lot less happy about it. People kept coming up to the register to pay along with other salespeople, and customers also kept walking in from outside. Where Mel and he were waiting kept him on full display in front of absolutely everybody. And the fact that he was wearing his maid’s uniform, complete with his apron, only made things all that much worse. He caught the attention of absolutely everybody that walked by.
Mel did her best to act like a well-to-do lady out with her maid. She tried hard not to laugh or giggle. But the more people kept staring at Chad, the harder it was getting. She wondered how he felt about being on display like he was. She almost laughed out loud at the thought. Knowing him though, the sissy was probably loving it! Keeping him on display like he was right now wasn’t part of her plan for the day, but she had to admit, it was certainly working out well. She glanced back at him. He was standing there with his purse hung over his arm, his other hand fidgeted nervously with his apron. He had a very worried look on his face. “Stand still, Sissy. Stop fidgeting. Let the people see what a well behaved maid you really are.” She turned away from him again and did her very best not to laugh or even smile too much. It wasn’t easy!
Chad immediately let go of his apron and put his hand back down by his side. Stand still? He wasn’t hardly moving! Although moving would be nice. It would be nice to run as fast as the low-heeled shoes on his feet would let him. But run where? The safest place would be back into her car. But he didn’t have a key to unlock it. Where would he run to? Stand still? The truth was, his feet felt rooted to the floor. He was too nervous to move an inch!
The saleswoman finally returned with several packages in her hand and set them down next to the register. Mel walked up and set her purse down on the counter to pay for everything, but Chad stayed where he was. His legs didn’t feel like they were interested in moving yet. But with Mel no longer close to him, he felt more exposed than ever. Damn! He was out in public wearing a maid’s dress! Who would have ever thought? He couldn’t believe it. And worse, deep down, it was stimulating his incredible sexual need.