The Bet - Chapter 8 (Saturday – week 1 Part 2)

The Bet
by Karen Singer

Chapter 8 (Saturday – week 1 Part 2)

Mel kept Chad busy in his own apartment for the next few hours as she had him put everything in the bags away somewhere and started to make his place a bit more organized. At lunchtime, she went out and brought back some burgers for each of them and made him eat all of his, even though he was still full from all the donuts he had eaten earlier.
In his bathroom, Mel threw away every male item she could find and replaced it with something feminine instead. Suddenly, the only shampoo, deodorant, and razors that Chad had were now all female. And there were a lot of other feminine items on his counter too. The towels on his towel rack were now all pink as were the washcloths.
Chad had to put the little girl sheets on his blow-up mattress and the matching pillow case on his pillow. His blanket was neatly folded so as to leave no question about what kind of sheets were on the bed. His teddy bear was prominently propped up on his pillow.
The two cardboard chests were put together and all of Chad’s bras were place in one drawer while his pantyhose were placed in another. Mel took all of Chad’s male underpants, undershirts, socks, and the few pairs of panties he owned and put them together into a bag to take back to her apartment. Chad was devastated to see them go. Chad’s plastic panties went into the top drawer of the other chest, and the pink Barbie clock radio was displayed on top.
As Mel directed, Chad gradually rearranged his entire apartment to organize it better. Once most of the boxes were moved to better positions, the apartment began to look much better, but also a lot more empty.
Mel placed the only chair in his apartment in a more prominent place where she could always sit and watch him easier. Then she found the framed contract and handed it to him. Chad was more than surprised as soon as he saw what it was. He also wasn’t very happy about it. “Mel… why did you do that?” he said through his pacifier.
“Wait a minute, Chad,” she began.
Chad realized that he had complained again. Fearful of another beating, he quickly added, “I’m sorry! I didn’t mean to complain. It just surprised me, that’s all.”
But Mel held up her hand. Fortunately, she didn’t look all that upset. “Chad, don’t worry. There’s something else we need to discuss that I was going to bring up later, but right now is as good a time as any.”
Chad only relaxed slightly. “What?”
Mel took a deep breath. It felt like she was about to take another major step forward. Slightly frightening in a way. She looked at Chad, he was waiting. But she felt like she needed a more formal way to put across what she wanted to tell him. Just standing there with him felt all wrong. She walked over and sat in the chair and pointed to the floor in front of her. “Kneel down.”
With more trepidation than ever, Chad did as he was told and kneeled in front of her.
Mel felt a little like a queen sitting in that chair with her subject kneeling in front of her. “Chad,” she began. “I don’t think that it’s right that you call me Mel anymore. You’ve got to stop.” He looked at her questioningly. “From now on, I never want to hear you call me anything but Mistress. Got that? Mistress. No matter where you are or what you’re doing. Only Mistress.”
Chad took that in. It wasn’t so bad. In fact, it kind if made sense. Not only that, but it also fell right in line with all of his fantasies. He smiled up at her and said, “Yes, Mistress.”
“Good. Now I want that contract hung right in the middle of that wall where everyone can see it.”

When he was done, Chad looked around at his apartment. Now that it was organized, it looked a lot better. It also looked a lot emptier. The only thing about the living room that he wasn’t happy about was the contract that was now displayed prominently on his wall. With only one chair in the entire room, anyone coming in couldn’t miss it. The vast empty space did make it easier for him to visualize the pool table he would soon have though.
His bedroom and bathroom worried him a bit. They now looked way too feminine and embarrassing should anyone see them. In a way, it stimulated him greatly, but at the same time, he was worried about anyone seeing them.
He expected that now that they were done, that Mel would be taking him back to her place and he was bracing himself for the trip out the door. But instead, she took him into his bathroom and changed his diapers again – and again inserting another of the dreaded suppositories. But this time, she didn’t lock the onesie back on him again. Instead she made him put one of the all-in-one girdles on again. That was soon followed by pantyhose and the highest pair of heels that he owned.
Mel looked at him critically. “You need makeup,” she decided. She went into his bathroom where they had put all the makeup that they had bought into one of the drawers. She started to pull various items out to put on him, then she stopped herself and put it all back. She looked at him. “You’re a sissy. You must have done this before. Show me what you can do.” And with that she reached out and pulled his pacifier out of his mouth and set it on the counter.
Chad was so relieved to have the thing gone. For hours now he had been only keeping it in his mouth by lightly clamping down on it with his teeth. He stretched his jaws for relief and walked over to the drawer full of makeup.
He would have much rather had her put the makeup on him. He had played with makeup once or twice before, but only a very little bit. Tentatively, he looked through the various items in the drawer. So much stuff. He saw some eye shadow and figured that would be good to start with. As best as he could, he spread some out on his eyelids. Mascara, he thought, that should be next. He found some in the drawer. It seemed to take forever for him to put some on, and even then he couldn’t really see it. Finally, he grabbed one of the lipsticks and smeared that on his lips. He examined the overall affect in the mirror. But he didn’t have to say it, Mel said it for him. “Pitiful! Absolutely pitiful! Look at you, you didn’t bother with any foundation, you did the eye shadow all wrong, none of the colors work right together, and don’t even get me started on how badly you did the mascara. Pitiful! Just pitiful!”
“Um, I really haven’t had much practice with any of this,” he admitted.
“Well, it shows!” She stopped and looked at him for a moment, trying to figure out how to proceed. She was tempted to do it all for him, but the guy really needed to learn. “Ok, wash it all off, then we’ll start with something basic.” As soon as Chad’s face was clean again, Mel had him find all the mascaras that were in the drawer, three of them, just so he would know for sure what they were. Then she made him practice over and over again putting it on. But finally she had had enough. “Ok, that’s enough for today. I have other things I need to do. You can practice more later.” She left his latest mascara job alone and began making up his face – completely.
When she was done, Chad looked at himself in the mirror. Wow! She had done a great job. He couldn’t believe how different, and certainly much more feminine he looked. He turned towards Mel. “I can’t believe how different I look! Thank you.”
“You’d better start learning to do all that, and learn it fast!” Mel replied. “Now let’s finish getting you dressed.”
Mel stuffed a couple of pairs of pantyhose into the cups of his all-in-one girdle, then she pulled a black skirt and a white blouse out of his closet and had him put them on. “Almost acceptable,” she noted. “Of course, there’s a lot of stuff you still need and there’s no way that you could ever pass for a woman… yet. But I guess I can’t expect too much since it’s only been a week.” She sighed. He was about as ready as she could get him right now. It was time for something else. “Back to the living room,” she ordered as she picked up his pacifier and took it with her.
Mel once again sat in her chair and pointed to the floor. Chad immediately kneeled in front of her, all the while, wondering what she wanted next. Calling her Mistress certainly wasn’t bad at all. But if there was one thing he had learned in the past week, she could be full of surprises. That fact worried him.
“What’s my name?” she asked.
Chad knew what she wanted. “Mistress,” he answered immediately.
“Say it again.”
“Mistress.”
“Again.”
“Mistress.”
Mel actually liked the sound of it. Just hearing him call her Mistress gave her a lot of pleasure. But she knew he would be less happy about what she wanted now. “That’s right!” she answered him. “I’m your Mistress. And as your Mistress… and because our contract says I can… I have a new command for you.”
Chad listened intently, but very warily.
“From now on, your name is no longer Chad. I never… ever… want to hear you tell ANYONE that your name is Chad. From now on, the only name you may use is… Sissy!”
Chad was stunned. “Sissy?” he repeated quietly in shock.
“Sissy! If I ever hear you even say the name Chad again, I’ll have your name changed legally and permanently. And if you think I can’t do that, then just think about how easy it is for anyone to change their names whenever they want. Women change them all the time when they get married don’t they?”
“Yyyyyes,” he stuttered quietly.
“And remember, I’m a lawyer, I deal with that kind of thing all the time. So I know how to do it. So if you don’t want it changed legally… yet… then I suggest that you try very hard to remember just what I told you.” She paused for a few minutes while she watched him trying to digest that. “Now, who are you?”
“Sissy,” he answered quietly and ashamed.
“Louder. Who are you?”
“Sissy,” Chad said a bit louder.
“Tell me your name!”
“I’m Sissy,” he said faster and louder.
“Good. I just hope you remember that.” Mel knew that it wasn’t actually as easy to change someone’s name as she had said it was, but she was also betting that he wouldn’t know that.
Chad was having a very hard time digesting his new name. Could she really change it legally on him? The more he thought about it, the more he was sure that she could. That could cause him some major complications. In fact, even during the course of this bet, he had no doubt that it was going to cause problems. His new name was supposed to be
Sissy? How utterly embarrassing. Worse, he felt like some tiny part of himself had just been ripped away.
Mel got up from her chair and picked up her purse that she had left by the front door. She dropped his pacifier inside. “Ok, Sissy, there’s something I promised someone you would do for them, and now you’re going to have to do it.”
Chad got to his feet, suddenly very worried. Do something for someone? He was already dreading whatever it was going to be. Especially dressed the way he was.
“I want you to go knock on the door of the apartment next door and introduce yourself properly to the two women in there. And I’m going to be right behind you so don’t you dare do anything wrong!”
Chad was aghast. “You mean those two women who…”
“Yes, those two! Now get moving. And remember, if I ever hear you speak the name Chad again… well, you’ll be more than very sorry!”
Swallowing very hard, Chad headed for his front door. Mel opened it wide and held it open for him. Earlier that day he had been outside over and over again wearing the embarrassing onesie. Now he was wearing a skirt and made up more like a woman. It was another complete embarrassment. He heard Mel locking his door behind him. He didn’t even have a key to get back into his own apartment. Slowly, his heels clip-clopped their way towards the apartment past his. He was supposed to introduce himself with his new name. He had to tell someone that his name was Sissy now. How was he going to do it? There were major butterflies in his stomach.
He stopped at the door and looked back at Mel. She was waiting. Taking a deep breath, he reached out and knocked, softly. He was silently praying that nobody was home. But his prayer wasn’t answered. He heard someone coming to the door. And then it opened. The woman with the short dark hair was standing there. Before Chad could say a word, she screamed with delight. “Oh! Look at you! So precious!” Then she turned to yell behind her. “Sandy, come look. Quick! See who’s here.”
The woman with the lighter colored long hair walked out of the bedroom. “Ohhh!” she squeeled in delight.”
The dark haired one opened the door. “Come on in, come on in.”
Chad did as he was told. At least he wasn’t outside anymore. Mel followed right after him. “Hi Cassie. Hi Sandy,” she said casually to the two women.
“Hi Mel,” the longer haired one, who Chad now guessed was Sandy answered.
“You brought us a present,” Cassie said, walking slowly around Chad, examining him critically. “He’s adorable. Of course, watching him earlier running back and forth may just have been one of the highlights of my life!”
Chad was praying again. He was praying for the floor to open up and swallow him. A major earthquake should do it.
Mel laughed. “I just thought it was time you finally met your new neighbor – properly!” Chad didn’t miss the emphasis she had placed on the last word.
“Ooooo,” Sandy squeeled. “It’s about time.” She and Cassie quickly stood next to each other excitedly. Chad noticed that Sandy reached out and grabbed the other girl’s hand and was holding it tightly.
He looked at Mel, she was waiting. He looked back at the two girls, they were waiting too. Oh God! He didn’t want to do this! But he forced words out of his mouth. “I just wanted to say that I’m your new neighbor next door. And my name is,” the pause was every so slight, but it was definitely there, “Sissy.” He had done it now. He had actually told someone – make that two people - that his name was Sissy. He would forever be branded with that name now.
The two girls both started squealing with delight. “Oh Mel,” Cassie said. “I love it! You know I have a girlfriend who everybody calls Sissy. Of course she’s a girl.”
“Yeah,” replied Mel. “I thought of that. It’s a common enough name for a girl, but more importantly, it will forever serve as a reminder to him of exactly what he is.”
Chad was praying harder and harder for that earthquake to swallow him up.
“I see he’s finally wearing makeup,” Sandy noted as she finally let go of Cassie’s hand.
“Ugh!” Mel grunted. “You should see how awful the job he did himself was. I had to do that for him. I’m afraid he’s going to need a lot of practice.”
“Well, makeup can be hard,” Cassie replied in a slightly taunting voice, as if she were sticking up for him. “It’s one of the reasons why I don’t use much myself.”
The two girls laughed, although neither Mel nor Chad knew exactly what about.
“Anyway,” Cassie continued, “makeup is really more of Sandy’s thing.”
“Well let’s be honest,” Sandy replied. “You don’t really need a lot of makeup with your job. I do.”
“Yeah, but you’re good at it. Mostly, I just don’t care.”
“That’s ok. I like you just the way you are.” The two girls laughed again.
The familiarity between the two women was hard to miss, especially in their own apartment. Definitely lesbians, Mel thought. Without a doubt.
Mel picked up on something that Sandy had said. “What kind of job do you have?” she asked her.
But it was Cassie who answered, “Oh, she’s an interior decorator. And she’s great! She just doesn’t think so yet.”
“Well, I’m not great. But I do think I do a pretty good job.” Sandy retorted.
“Pretty good… Mel, look at this place. It looks great doesn’t it?”
Mel had to agree, it really looked fabulous. All except for one small work area that was incredibly cluttered. “Yes, it does look good,” she replied. “Really good!”
While the women talked, Chad inched his way out of the way more and just remained silent and in the background. As long as nobody was paying attention to him, he was a lot happier. He wondered if he dared to sit down. She had made him wear his highest heels and they were starting to hurt his feet. While he listened quietly, he learned that Cassie was an aerobics and dance instructor in a women’s gym. That explained why she didn’t need a lot of makeup in her job. Cassie spent a few minutes trying over and over again to convince Mel to join the gym, but Mel was just too busy with her job. Because he was just standing still, Chad’s feet were starting to hurt more and more. He decided to chance sitting down. Slowly, so as not to attract too much attention, he moved over to one of the chairs and sat, being careful to smooth his skirt out under him as he did so. The women each glanced at him quickly as he sat down, but they were busy talking and went right back to it. He breathed a sigh of relief. But unfortunately, his movement brought the conversation right back to him.
“And how is his training going?” Cassie asked.
Chad was suddenly aghast. These women knew? Suddenly all three of them were looking straight at him again.
Mel sighed. “Ok, I guess. I’ve been force feeding him bottles of a green tea mixture that I make up. It’s supposed to be a strong diuretic and I’ve been making it really strong hoping that it will make him have to pee more. And I think it’s working. At least I hope it is.”
They were suddenly all looking at him. He realized they were looking for an answer. “It is.” Chad said. “Believe me, it is.” But they just continued to look at him. Were they expecting more? “Sometimes I think I’m peeing almost every half hour. It’s especially bad at night because it keeps waking me up. I haven’t slept well all week!”
Mel smiled at him. “Like I told you, just think how much better it will be when you learn to sleep through it.” All three girls started laughing hysterically.
Mel suddenly looked troubled. “That reminds me,” she said in her no nonsense voice. She pulled the pacifier out of her purse and stuck it into his mouth again. “That stays there!”
Chad was aghast. One humiliation on top of another, and there was nothing he could do about it. Sandy and Cassie started laughing at him all over again.
“It’s his latest phase of training,” she told them. “I think he looks adorable sucking on it like a good sissy baby. Don’t you think?”
“Oh definitely,” Cassie replied. “Definitely.” All the women enjoyed a good long laugh.
Chad couldn’t understand why that earthquake he was praying for should be delayed so much. He sat and listened as Mel began telling them a little about the things she had been putting him through all week. Things that Chad really didn’t want to be reminded of. Way too many incredibly humiliating things. He couldn’t blame them for laughing, if he were in their position, he would laugh too. And despite how embarrassing it all was, it was making him horny again. It certainly didn’t seem to take much anymore. He really needed some relief.
He had been only half-listening for a while now, mostly lost in reliving the embarrassments he had been through over and over again. He was enjoying it because he was feeling his horniness as an internal warmth. A delicious warmth that he was surprisingly enjoying. But he was jolted back to reality when Cassie said, “Maybe I can help.”
Chad desperately tried to remember what they had been talking about. Oh yeah, Mel had mentioned she was going to be putting suppositories up his rear end with each diaper change for the foreseeable future. She had been planning on making him drive to her office every day at lunchtime to change him and put another suppository in him, but her schedule wasn’t exactly the best for doing it.
“Where does he work?” Cassie asked. Mel told him. “I think I know where that is, and it’s only a few blocks from the gym. Why don’t you have him come to the gym at lunch every day and I can change him for you.”
Mel looked very surprised. “Are you sure?” she asked tentatively. “You know, he’s going to be messy.”
Cassie scoffed at that. “Don’t worry, I’m not afraid of a little mess. You wouldn’t believe how many women barf all over everything while they’re exercising and I have to clean that up. I can’t imagine that he could possibly be much worse.”
Mel shook her head. Chad was sure she was going to decline and he was very glad about that. Things were bad enough for him already. But Mel didn’t decline. “Well, if you’re absolutely sure about it. It really would be a big help.”
“Mel, you know I’ll be glad to do it.”
“Ok then,” Mel replied. “Staring Monday, I’ll send him to you at lunchtime. And don’t worry, I’ll make sure he has everything you need.” She looked over at Chad then and suddenly he was more afraid than ever.

That night, Chad laid down on his blow-up mattress and began sucking on the first of the three baby bottles that Mel had left with him. They were all taped at the top so he couldn’t dump them out. The darn pacifier she had been making him suck on most of the day was now pinned by a pink ribbon to his onesie where he was supposed to start sucking on it as soon as the last bottle was finished. And she had been very clear that he was supposed to keep sucking on it all night long. Ugh!
He was so tired. Bone tired. It had been a very long day and he hadn’t slept much all week. The new sheets he was laying on felt very nice against his hairless legs. The pillow case felt nice too. They were just embarrassing to look at. He had placed his teddy bear on the floor where it would be out of his way while he slept. He had a feeling that Mel wouldn’t exactly approve, but she hadn’t said anything about it earlier.
He replayed the day over and over again in his head. He had to call himself Sissy now. His new name. A girl’s name. A name that all too well described exactly what he was. How utterly embarrassing. That thought alone began making him grow hard again inside his already wet diapers. And starting next week he was going to have to have his diapers changed at lunchtime. That part he was actually really happy about. It had been difficult going all day, peeing as much as he now did, without having his diapers changed. He realized that just the thought of somebody changing him like a baby was also fueling his need for release. He needed to pee again, but knew he couldn’t. He was too hard, even inside of his diapers. He desperately tried to rub himself through his baby-doll nighty and the onesie that was again locked on him. But it was no good. The diapers she had been put on him again for the night were way too thick. He had thought that the cloth diapers would be more fun than the disposables, but in truth, they were just different. With the cloth diapers he could always feel it when he was wet, which was now almost always. But he was wet so much that he had quickly gotten used to it. Being wet all the time was beginning to feel normal to him. How interesting he decided. His aching cock gave another twinge, begging for relief. His balls were aching horribly too. Something that he was sure that Mel would care nothing about. He tried desperately again to rub enough sensation through his thick diapers to get some relief. But again he was left denied. He was so incredibly frustrated over it – and that too was fueling his desire. He couldn’t win.
It had only been a week. A long and horribly humiliating week. Every day had seemed to bring humiliation after humiliation. He had hated it and loved it. What would next week bring? One thing was for sure, she couldn’t do much more to humiliate him than she already had. That thought alone was comforting.
One week gone out of the two month bet. As he drank his bottle of the horrible tea, he felt his need to pee growing. He couldn’t pee of course as hard as he was, but just the fact that he knew he needed to pee so much let him know that he still had total control. As much as she had put him through, she hadn’t stripped anything away from him at all. He was going to win that bet. Of that he had no doubt at all.