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.

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

The Bet
by Karen Singer

Chapter 8 (Saturday – week 1 Part 1)

Mel woke up and stretched luxuriously. She felt better than she had in a very long time. Chad’s tongue had done absolute wonders for her and the way she felt. She glanced at her clock. Oh dear, she had slept a lot later than she had meant to. Poor Chad was still tied up in her living room. She actually smiled at that thought. The power that she felt over him sent waves of pleasure through her body once again. “Later,” she told herself. “Later.” Knowing how miserable he probably felt, she immediately got out of bed.
Chad was only half awake. It was nearly impossible to sleep well tied up on the floor as he was… not to mention having to pee into his diapers over and over again… not to mention occasionally having a mess sliding out of his rear end once in a while… not to mention trying to sleep with so much sexual need bottled up inside of him. If he thought he had felt miserable last night, he felt twice as bad this morning. He was so glad when he finally heard Mel stirring in her bedroom. He prayed she would release him soon.
Mel hurried over and began untying him. She could see how miserable he was. He looked like he hadn’t slept much again. She shouldn’t have slept so late herself. Tough though, the poor guy was just going to have to get used to it. As soon as he was untied, she let him rub his arms and legs and stretch for a few moments. By the way he was moving, she was sure he was really hurting. “I’ll meet you in the bathroom,” she finally said, and then she left him to recover a bit more.
Chad finally crawled into the bathroom. He knew she’d probably let him walk, but he wasn’t sure he could just then. Mel unlocked his onesie and helped him undress. Then she let him soak clean under the shower. The warm spray felt great against his whole body – except his blistered backside. That was still tender to the touch. When he was done, Mel began running the bath water and soon he was relaxing in the warm scented water while she shaved every bit of his body once again. After his bath, Mel diapered him again in soft cloth diapers that didn’t feel nearly as thick as they had the night before. But what distressed him was the suppository she shoved up inside him before she fastened his diapers again. He wanted to protest, but he dared not. At that point, he didn’t really care all that much anyway. He was too bone tired again.
Mel finished him up by locking the onesie back on him again and then had him put his heels back on. “Go lay down on the couch,” she instructed. “I’ll bring you your bottle.”
Chad gladly did as he was told. In truth, he really just wanted to go straight to sleep there, but since she had handed him the bottle, he knew better than to not drink it – now. Mel’s couch felt really great – comfortable. The bottle he was drinking seemed almost comforting after what he had been through the night before. Even though he hated the dreaded green tea, he drank it greedily. As soon as he finished his bottle, he closed his eyes and fell soundly asleep. Finally.

Mel dressed casually for the day in jeans and a t-shirt. This was going to be mostly a working day, so the clothes were appropriate. She had a few fun things lined up for Chad later, but there was work to do first. She walked into her living room and saw Chad fast asleep. She left him there and began searching through the bags he had brought in the night before. “Found one!” she said softly as she reached into the bag and pulled out a package of pacifiers. She opened the package and washed them carefully. Then she took one of them into the living room where Chad was sleeping.
Chad was sound asleep when he suddenly felt something being gently pushed into his mouth. He jolted half awake, “What?”
“Shhh! Here keep this in your mouth and don’t take it out,” Mel said softly. “Go back to sleep.”
In his half awake state, it took Chad a moment to realize what it was. He put his hand up to grab it.
“Don’t touch!” Mel cautioned him. “Keep it there and go back to sleep for a while.”
Sighing wearily, Chad did just that.

Mel busied herself in her apartment while she let Chad sleep for a while. She poked through the bags of things they had bought just to look at some of them again. A few things she pulled out and put away in her kitchen since she thought they would be useful. When she was done, she found the small hammer she kept in the apartment and a box of picture hangers. From her bedroom, she found both copies of the contracts that she had had framed and pulled them out. Hers she placed on her desk leaning against the wall until she could decide where to put it. Chad’s she placed in one of the bags along with the hammer and the hanger.
Mel let Chad sleep for about an hour before she decided it was time to wake him up and get busy. But when she went to wake him, she noticed that his pacifier had fallen out of his mouth and was just laying on the couch next to his head. She picked it up and put it back into his mouth. Chad woke up instantly.
“What?” He was still so groggy.
“Keep this in your mouth.” She held it till she felt him sucking on it again. “Come on, time to get up and get busy.”
Chad swung himself to a sitting position till he could wake up a bit more. He was so groggy still. He unconsciously reached for the pacifier in his mouth again and was stunned when she slapped his hand.
“Don’t touch!”
He got the point. It also helped to wake him up a bit more.
“Come on,” she coaxed him. “There’s a bottle waiting for you in the kitchen.”
“Oh hell,” he thought. As he stood up and began walking to the kitchen he weakly realized that he had to pee again. He barely thought about it as he wet himself.
As he sat down on the hard kitchen floor with his bottle, he realized just how tender his backside still was. He rocked back and forth trying to find a comfortable way to sit, but he couldn’t. Finally, he laid down on his side and put the bottle to his mouth. He couldn’t believe how much the beating she had given him still hurt. He’d have to think carefully about not doing everything she told him to right away from now on. She really knew how to make a point.
As he started in on the bottle, Mel asked him, “Are you usually a breakfast eater?”
“When I can,” he replied. “Sometimes I only have time for coffee, but when I can I grab something from a fast food place on the way to work.”
Mel nodded. “I’m going out for some donuts. I’ll be right back.” She started to walk away then stopped. “Can you cook?”
“A little, I guess,” he replied.
Mel nodded thoughtfully. “Well have to see. Maybe later we’ll go grocery shopping.” Then she walked out.
Chad was left alone with his baby bottle to finish. He didn’t dare dump it out or even think about getting up off the floor till he had finished it. But when he was done, he did get up and wandered around a bit. She wasn’t back yet, but he had no doubt that she wouldn’t be much longer. He really wanted to lay back down and sleep some more, but he didn’t dare do that either. Not wanting to cause any trouble for himself, he decided that maybe he should at least attempt to do something useful. So he began washing dishes – mostly baby bottles.
Mel came back with a box full of donuts and two large cups of coffee while he was still at the sink. She was more than pleased to see what he was doing. “Oh, what a good baby you are!” she told him as she set everything down on the counter. The compliment actually sent waves of pleasure throughout Chad’s body. While Chad finished what he was doing, Mel grabbed one of the baby bottles he had just washed and poured coffee from one of the cups into it. Chad had no question now about which cup was his.
As soon as he finished the dishes, Mel pointed to the box of donuts. “Start eating,” she said with her mouth full. The box held a dozen varying kinds of donuts, each one looking more appetizing then the next. He selected one and put it in his mouth. Very sweet, very tasty, and oh so good! He didn’t even think about it as he grabbed his baby bottle full of coffee to help wash it down. As soon as he finished the donut, Mel said, “Have another one.”
“May I?” he asked politely. Mel just pointed at them since her mouth was full.
As Chad was eating, Mel got up and left him. She went to her desk to catch up on some work, leaving him alone. “That was good. Thank you,” he called to her as soon as he finished the donut.
“Have another one,” she called from her desk.
“No thank you. I’ve had enough.”
“I said have another one!”
He was a bit surprised at her attitude, but he wasn’t about to not do whatever she said, besides, they really were good. So he ate a third one. This time, when he finished it, he walked out to where she was working. “I’m done,” he told her. “Is there anything you want me to do now?”
Mel looked around her. “Get busy,” she said simply. “Clean! There’s laundry to do, beds to be made, the carpet needs cleaning, the furniture needs…” But Mel stopped dead right there as soon as she saw the sudden surprised look on Chad’s face.
Chad had been listening to what Mel was saying and was just about to get busy, when the suppository she had put in him earlier decided to do its job. It was so sudden that he was filling his diapers without warning. It really felt more like everything in him was just falling out.
“What’s wrong?” Mel asked.
“I just…”
Mel nodded knowingly. She turned back to her work. “Get busy. And have another donut first.”
With the cloth diapers on instead of his usual disposable ones, Chad was more than ever aware of the mess inside of them. He felt the wetness too against his skin. And the longer he wore them now, the more the wetness and the mess seemed to irritate his already blistered rear end. The cloth diapers were thinner than the ones he had worn all night, but he had been tied up then, unable to move. Now he had to walk around and do things. And the awful mess in his diapers meant he had to move a lot more carefully. He was used to waddling around in thick diapers now, but having to constantly feel the wet mess in his backside caused him to waddle with even more of a wide legged gait. It was uncomfortable and he knew he looked silly doing it, but what choice did he have.
He started in on the laundry, but he had only started to load the clothes in the washer when Mel came to find him. “You forgot this,” she said, holding out his pacifier. “She stuck it in his mouth for him. Suck on it and don’t let me catch it out of your mouth.” Then she was gone.
Chad sighed. The woman could be very difficult. But damn if sucking on a pacifier like a baby wasn’t making him horny. Having to see the bright red polish on his nails while he worked was having the same effect on him too. Now if he could just figure out a way to get a little relief.
Chad’s work was slowed down a lot because Mel kept stopping him every half-hour or so to make him eat another donut or drink another baby bottle. As soon as he finished each time though, she made sure that his pacifier quickly went right back into his mouth again. His mouth was getting really tired from all the sucking, but every time Mel caught him putting his hand anywhere near the pacifier to take it out for a minute she yelled at him. His jaw was beginning to ache and his lips were going numb, but what could he do?
It was nearly noon before Mel finished with what she was working on and decided that Chad had done enough. When she found him, Chad thought that she was going to bring him another baby bottle to drink – thankfully, the donuts were finally all gone, she had made him eat ten of them and now he was so full that he couldn’t eat another bite if he tried. But Mel surprised him by deciding to change his sopping wet and messy diapers instead. That really pleased him. Unfortunately, what didn’t please him was that she inserted another suppository when she did it. Things were definitely getting worse he decided.
Once he was again dressed and firmly locked in his onesie, Mel told him to start taking all the bags from the stuff he had bought last night back to his apartment. But the thought of going outside dressed like he was, shocked him too much. Without stopping to think about what he was doing, he said, “What? I can’t! Not like this!” Even though the words were slightly blurred by the pacifier in his mouth, the panic in his voice was plainly evident.
Mel’s reply wasn’t loud and it wasn’t fast, but was enough to let Chad know instantly that he had messed up, and bad. “Shall I get my yardstick again?”
Chad nearly panicked. He had been really glad all morning that everything she had him doing didn’t require him to sit down. With a huge amount of trepidation, he picked up his keys and as many bags as he could carry in his arms at one time and headed for her door, mentally bracing himself for the dash outside to his own apartment. But Mel’s voice cut through the room, “Only two at a time.” Chad looked at her like she was crazy, but she wasn’t. “Would you rather do it one at a time?” she added.
Chad set all but two of the bags down on the floor again. He realized it would be easier to manage since he had to unlock his door anyway. Maybe he could get back and forth quicker. Dreading it horribly, he went out and ran for his own apartment as fast as the heels on his feet would allow. But just coming up the top of the steps ahead of him was one of the girls from the apartment past his. He heard her surprised little scream as he quickly unlocked his door and ran inside, closing it just as quickly behind him.
But then he had to go back again. He waited a moment to let the woman get back inside her own apartment before he opened his door again. He cautiously looked out. The darn woman was standing right next to her door, looking straight at him. He ducked back inside again and waited a few moments longer, then he looked back again. She was still there! Darn it! The damn woman wasn’t going away. Not having any choice, he ran out and back to Mel’s apartment.
“What took you so long?” Mel asked.
“One of those women from the other night was out there and she saw me.”
Mel smiled. “Did she like what she saw?”
Chad groaned and picked up two more bags. But when he went outside, not only was the woman out there, but her dark haired friend was out there too. Both of them, just standing there watching him. Once again he ran for the safety of his own apartment. This time, he didn’t even wait. He quickly set the bags down and ran back out for another load. The quicker he got this over with, the better.
“That was fast this time,” Mel noted. “I take it she’s gone now.”
“No! Not only is she out there, but so is her friend!”
“Really now,” Mel was a bit surprised but was suddenly enjoying Chad’s new discomfort. Not wanting to spoil it, she said nothing, but as soon as he was back out the door with another load, she poked her head out to see what was going on. She nearly burst out laughing.
Chad went out through Mel’s door and almost stopped dead. Fortunately, he collected himself just in time and continued on ahead. Both women were still there, but now one of them had found a lawn chair and was sitting on it with her drink. They were both out there just to enjoy the show. “Wooo hooo!” he heard one of them shouting as he continued towards his own apartment. Yeah, they were enjoying the show all right. A little too much.
On the return trip to Mel’s apartment, he heard them clapping and shouting again. But now Mel herself was leaning in her doorway watching the show too. He wasn’t running anymore. Just very resigned, he grabbed more stuff and continued moving it to his place. But a little too late, he realized that maybe all the running he had just done hadn’t been a really good idea, because as he was halfway between apartments again, the latest suppository did its job. And just like before, it was so sudden that there was no real warning. All the donuts he had been eating all morning hadn’t helped at all either. He stopped dead when it happened with a terrified look on his face. When he could continue walking again, it was much more gingerly. The two women in front of him were obviously wondering what had happened, but he heard Mel laughing openly behind him.
He dropped the bags off and went back for another load, cursing the fact that they had bought so much stuff and that the store had insisted on putting so few items in each bag. But when he went back out, Mel was just passing him on her way to see the two women. Again, walking – or more like waddling – gingerly, he went back for another load. The women all laughed and talked as he made the last of the trips. He couldn’t imagine anything in the world more embarrassing than what he had just done. When he was done, he left his door open because he had no doubt that Mel would soon follow him into his apartment. He went to his blow-up mattress and buried his head in his pillow. If only the world would swallow him up right now so he couldn’t feel the embarrassment anymore.

The Bet - Chapter 7 (Friday - week 1 Part 3)

The Bet
by Karen Singer

Chapter 7 (Friday - week 1 Part 3)

Once they were home, she had Chad carry everything up to her apartment, even though most of it was going to go to his place. It took him several trips but fortunately it was dark and in the dim lights he didn’t feel quite so exposed.
While Chad was lugging bags up to her apartment, Mel began filling baby bottles again with tea. But her mind was mostly on something else. What about her needs? In the middle of bottle number six, she came to the obvious answer.
As soon as Chad was finished bringing everything up, Mel handed him a baby bottle and sat him down on the kitchen floor with it. He was so used to that by now that he hardly gave sucking on it a thought. What was on his mind was his earlier question, would she allow him some much needed relief? He watched from the floor as she finished filling all too many bottles and put the pitcher back into the refrigerator. Her mind seemed to be elsewhere. He was tempted to ask her again, but something about her mood stopped him. He was soon left alone on the kitchen floor while she was busy in the living room where he couldn’t see her.
“I’m done,” he called out finally.
“Get another one,” she yelled from the living room.
Chad wasn’t at all happy about the tone of her voice. Something was eating her. But so as not to make any trouble for himself he got another of the bottles and sat back down to drink it. He peed twice before he could finish it. “I’m done,” he finally called again. “And I peed… twice,” he added.
“Good! Now get your ass in here!”
Chad was really surprised at her attitude. Not to mention a bit apprehensive too.
“Strip!” she said in her no-nonsense voice.
Chad began getting undressed, all the while watching her. She didn’t look happy. What had he done now?
Mel waited till he was completely naked. “Now drape yourself over the coffee table again like you did before. You know the drill.”
Chad was scared, but he did as he was told. “What did I do?” he asked as Mel began fastening the first rope to his outstretched wrist. But Mel remained silent, only determined. A few minutes later, Chad was completely restrained, if anything, even tighter than the last time. Mel left him for a few minutes then came back again. Woosh! Chad felt the burning sting as whatever she was hitting him with, hit his backside again. “Ouch!” he cried.
“Do I have your attention now?” Mel asked right next to his ear. But she didn’t wait for an answer before she brought her yardstick down on him again. “How about now?” “Yes! Yes, you have my attention!” Chad screamed.
“Good!” Mel brought the stick down again and Chad’s body jerked as much as it was able, which wasn’t very much. She got down next to his ear again. “Now let’s get this straight. When I tell you to do something, you do it!” She brought the yardstick down again. “Got that?”
“Yes!” Chad screamed. “I thought I was!”
“Not even close. First of all, when I told you to drink both those bottles last night, you didn’t! Did you think I’d forget about that?” She brought her yardstick down again. “And then tonight, when I told you to wet yourself in that store you didn’t!” This time, she brought her stick down on him twice.
“But I couldn’t! It’s impossible! Guys can’t do it when they’re hard!”
She brought her stick down again. “Then we’re just going to have to work on a way so you won’t get hard anymore, won’t we.” She had said it so evilly that Chad actually shuddered. Mel moved around to his other ear. “And that brings up another subject. I don’t care about your needs. Your needs don’t matter! If you have any questions about that then go look at the contract again. My needs are all you should be thinking about. Not yours, mine! So think about that… and this!” And with that she started bringing her yardstick down on his backside over and over again, as hard as she could.
Through the pain, Chad soon realized that the last beating he had taken was nothing to the ferocity of this one. He was soon in real agony. Mel finally stopped and he began gasping for breath. But Mel was only switching to the other side of him and then the beating began again. Tears were falling from his eyes as agony increased.
Mel felt her arms growing tired. Chad’s backside was red and close to bleeding. She realized she was breathing hard. She stopped to examine her handiwork. Chad was totally miserable. She really hadn’t meant to beat him so much, but something just wasn’t sitting right with her. She realized that she would probably be starting her period soon and maybe that had fueled her rage. But really, there was something else. She watched him closely, he was writhing against his bonds. There were a few tears staining his face. And then it hit her. He was in agony, there could be no question about that, but what she wasn’t seeing was the deep down remorse she wanted him to feel inside. Frustrated, she brought her yardstick down on him a few more times. She had punished him badly. There was no question of that, but inwardly she was looking for a different reaction than he was incapable of giving. Men! What was it with them?
Frustrated, she threw her yardstick down and went to her bedroom to find her cell phone. She went into her bathroom and closed the door where she could be sure there would be no way for him to hear her and dialed a number. Gloria, her therapist was probably not at her office right now and she was right. She left a message. “Gloria, this is Mel. I have another little request that I’d like to see if you can work into your next session with Chad. If it’s possible… whenever I punish him… I’d really love to see him crying like an absolute baby!”
Feeling better and at least a little calmer, she left her bathroom and put her phone away. The she began gathering up everything she would need to rediaper him and get him ready for the night ahead.

Chad was ever so grateful when she finally began removing the ropes from his hands. As soon as he was able, he rolled onto the floor again and just writhed a few minutes against the pain from the ropes and especially the pain in his backside.
But Mel was all business. “Roll over,” she commanded.
He immediately rolled onto his stomach so she could work on his rear end. Chad felt the familiar cooling effect of the lotion as she rubbed it gently on him. A cooling effect that did nothing to alleviate the pain. She managed to work the lotion as far under him as she could, massaging his penis in ways he hadn’t expected, and then her hand was gone all too soon. He felt her insert another of the suppositories, he inwardly groaned, he really wished she hadn’t. But then he felt her inserting another one. He wanted so badly to protest, but he dared not. He hardly felt all the powder she was sprinkling on him. Then she rolled him over again and he realized that something felt different. Whatever she had rolled him over onto felt softer, thicker. More powder followed, although he could hardly feel it. What he really wanted to feel was her hand touching him again. But she didn’t, not at all. More frustrated than ever, he felt her pulling up his diapers. But they felt different. They were cloth this time he realized. Very thick, very soft, cloth diapers. Where had she gotten them from? She struggled at his waist to insert the diaper pins. When she was done, she leaned back and brushed her hands together in satisfaction. He realized that she had actually managed to pin the diapers onto him fairly tightly. Where had she learned to do that so well? He soon felt her pulling up his plastic panties. But those too felt different, newer. He wanted to look at it all, but he couldn’t see much from the position he was lying in on his back. He really, really wanted to ask her again to let him get himself off, but she had made her point about that perfectly clear. He’d just have to wait for a better opportunity.
“Ok,” she told him, “stand up.”
Chad got to his feet and took the opportunity to look down at what he was wearing. The plastic panties were mostly clear but had cute pink cartoon characters printed all over them. Extremely childish. Through the clear part of the plastic, he could just make out the pink diaper pins that held his cloth diapers together. “Where,” he started to say.
“From the internet,” Mel replied. “And that’s not all I got you.” She held out a strange looking garment. “Here, put this on.” She handed him one of the onsies that she had bought.
Chad practically blushed just looking at it because the material was an obviously very childish girl pattern. He turned it around trying to figure out the best way to put the thing on. Finally he stepped into it from the back and pulled it up over his arms. Mel came around behind him and zipped up the back. The he felt her doing something else at the top of the zipper and suddenly he heard a soft click.
“There!” she said, sounding very satisfied. “That should keep you out of trouble.” Mel stood back to examine her handiwork. “Don’t you look soooo cute now,” she laughed. “Don’t you just love your new diapers and onesie? From your reactions to things in the store earlier I’m sure you probably do.” She looked at him evilly. “Ok, baby. If you want to jerk yourself off, do it now while I’m still feeling generous. In fact, if you need to take anything off to help you do it better, then get to it. Just don’t take too long.”
Chad couldn’t believe it. He just stared open-mouthed at her while she sat on her couch in front of him and watched him. But an opportunity was an opportunity. He started trying to rub himself through everything he was wearing, but the diapers were too thick to feel hardly anything. The thick cloth diapers seemed to make feeling anything even more difficult than the disposables were. He rubbed his hands down his chest and waist. The darn garment she had put on him had no waist opening so he couldn’t get his hands inside his diapers that way. He reached for the zipper at the back, and froze. There was something fastened to the zipper. A lock he quickly realized. The bitch had locked him into the garment. He began tearing and pulling desperately at the onesie all over, but he was getting nowhere. He looked up to see Mel laughing at him.
“What’s the matter, baby? Having trouble?” She laughed again. “That onesie is supposed to be made very strong and all the openings are reinforced with material that you can’t cut with a knife or scissors. I’m afraid you’re not going to be able to get out of it till I let you out.”
Chad just stared at her unbelievingly as she got up from the couch again. The bitch. She had found still another way to make his life miserable.
“Now,” she commanded, “down on your knees again.” Her no-nonsense voice dropped Chad to his knees quickly. She grabbed his arms and pulled them behind his back where she tied his wrists together again. Then Chad felt her tying his ankles too. “Just stay there,” she taunted as she left him for her bedroom. A minute later, she was back again with a scarf in her hands. She blindfolded him tightly, making sure he couldn’t see anything.
Chad heard her pushing something in front of him, the coffee table he figured. Then he heard her moving around for a few minutes longer, but he had no way of knowing what she was doing. Very warily he waited. It’s all he could do.
Mel pushed the coffee table out of the way. Then she waved her hands in front of his face a few times, making sure that he couldn’t see anything. She was very nervous about what she was going to do next, but darn it, she had needs too. Very slowly she nervously removed her slacks and then her panties so she was naked from the waist down. She sat on her couch, directly in front of him and looked at him. Even blindfolded she could tell that he was worried about what she might do to him. He looked totally ridiculous dressed as he was and she loved it. It was the total control over him that excited her in ways she hadn’t realized.
It was time. “Ok, baby. Crawl forward to me.”
Not having the use of his hands, Chad began inching his way forward on his knees. He turned his head left and right, but he could get no sense of how far he had to go. “Keep coming,” he heard her say, closer now. He kept moving. “Stop!” she commanded.
Mel looked at him. So close, yet so far. The excitement of what she was doing was surging through every part of her body. She reached out and grabbed his hair with both hands and pulled him down into her waiting crotch. “Lick!” she commanded.
Chad felt her grab his hair, then he was almost thrown off balance when she pulled him down. His nose landed right in her pungent waiting sex. He was so surprised by it all that he tried to jerk away, but her hands holding his hair wouldn’t let him. Her command to lick got through to him. He had never done this before. Very tentatively, he reached out with his tongue until he felt it touch her, and he gave a small lick.
The gentle first touch of his tongue sent waves of lightning bolts all through Mel. It felt so delicious. But she wanted more. She pulled his head much harder into her waiting sex and ground her hips forward, urging him to lick harder, then harder still. This was power. This was excitement. This was what life was all about! And she loved it.

Later that night, Chad tried to collect his own feelings. He was bound once again as he had been a few nights ago in her living room. She had finally gone to bed again, unlike himself, fully sated. He was still terribly horny, but he was helpless to do anything about it. He wanted to move, to change positions, but he could do nothing at all. His bonds were too tight. The suppositories she had put in him had started to do their work before she was finished with him. The result seeming to make her even more excited. He wet again. It was getting easier. Too easy. Almost like being incontinent. He tried to fall asleep in the position he was in, but in his half dreaming state, he was all too excited by the dreams he had of really becoming incontinent. The same dream he had had the night before. If only, if only. But he knew for a fact that it couldn’t really happen. This had been a fetish of his for a long time. All the research he had done on the subject told him it would take a good nine or ten months… at least. Even if he wanted it badly. But right now, he wanted to win the bet even more. Still, it was an awfully pleasant dream.

The Bet - Chapter 7 (Friday - week 1 Part 2)

The Bet
by Karen Singer

Chapter 7 (Friday - week 1 Part 2)

After the nail salon, Mel took them to dinner at a casual restaurant. Chad was really hoping that they wouldn’t let him in, but other than lots of strange looks, nobody really said anything. His feet were somewhat hidden under the table, but he was all too aware of the red nails on his hands. Out in public, it was positively frightening.

When their drinks arrived, Mel grabbed his before he could drink any of it, which surprised him since he figured that she would be pouring liquids down his throat like she did every night. But what Mel did next really distressed him. She reached into her bag and pulled out an empty baby bottle and dumped as much of his drink into it as she could. Then she handed it to him.

Chad couldn’t believe it. “You can’t be serious!”

Mel looked surprised. “Of course I am.”

“I can’t do this,” he whispered urgently.

Her simple reply was almost taunting. “Yes you can.” She was smiling that wicked smile again.

The bitch was really serious. Chad looked around for any way out of it, but there was nothing.

“Remember that little contract we have?” Mel said. “And the parts where you have to do anything I tell you to? Well, drink up, baby. Drink up.”

Once again Chad wanted to die – quickly. He put the bottle to his lips and started sucking on it. Mel looked like she was going to burst out laughing. He heard comments from the tables around him too, but all he could do was to either look directly at Mel, who was watching him all too wickedly, or to close his eyes. He wanted to cry badly.


After dinner, he was so glad to get out of that restaurant. That was one place he could never go back to again. But what worried him now was what would be Mel’s next stop on her agenda. Mel drove them out to Target and led the way into the store, stopping at the entrance to have Chad grab a shopping cart. Chad expected her to head directly for the women’s department but she surprised him by heading to the baby department instead. Chad didn’t know whether to be relieved or sorry.

All through the store, Chad turned heads. As he stood by quietly while Mel pulled various items off the shelves to look at them closely, customers stopped at the ends of the aisle to look at him. He could tell that Mel was certainly enjoying herself, but he certainly wasn’t.

She was looking at large diaper bags when she finally held one up and said, “I think this one is pretty, don’t you?”

Chad looked at it. It was pink and obviously decorated for a baby girl. “Yes,” he agreed – tentatively.

“I just hope it’s large enough,” Mel replied as she placed it into the cart. As far as Chad could tell, the bag was the largest one on the shelf. The diaper bag was soon followed by several pacifiers, divided dishes for baby food, and a package of baby spoons. As she wandered up and down the baby aisles, Mel began pulling down anything she thought might be useful and putting them into the cart; baby wipes, more powder, more baby lotion, bottle brushes, anything she liked that caught her eye. Chad wasn’t happy to see any of the items going into the cart, but at the same time everything in his cart was adding to his incredibly horny state.

After the baby section, Mel began wandering around the rest of the store, stopping often to look at different things, sometimes adding something to the cart that she liked. Chad again had the impression that she was purposely delaying things to keep him exposed longer. He decided that some of the items she had put into the cart were probably for her because he could see no use that he would ever have for them.

Then they came to the makeup aisles. Chad had to stand there while Mel carefully looked over all too many of everything. His biggest concern though, was that she was putting three or four of each type of item, mostly different brands, into his cart. And unfortunately, while Mel was looking closely at a couple of lipsticks she had in her hands, a voice behind him asked, “Are they for him?” Chad turned and saw a woman standing a few feet behind him. He wondered for the thousandth time if his day could get any worse.

“Of course,” Mel replied, obviously making no secret about it. “I’m trying to decide which shade would look better on him. What do you think?” Mel held the two lipsticks out to the woman.

The woman took them and opened one and cranked the lipstick itself out. Then she held it up close to Chad’s face and looked at it carefully. Mel watched closely. Then the woman did the same with the other one. “I don’t know,” she finally said, “I think they’re both ok.”

“Good,” Mel replied taking the lipsticks from her again. “We’ll take both of them then.” With an air of triumph, she threw both lipsticks in Chad’s cart. Both women laughed.

“Good luck,” the woman said tauntingly to Chad before she sauntered off.

No, Chad decided. There was no way his day could ever get worse than this!

In the toy section, Mel looked closely at all the toys for girls and babies, but Chad was glad that she didn’t buy anything there, what use could they have been anyway? But a few minutes later, Mel’s eyes found a bin of soft teddy bears that she had to pick through. She hugged several of them. “Oh… these are so soft!” she exclaimed. A white one soon found its way into the cart. Chad looked at it closely while he pushed the cart behind her. A teddy bear! His horny state was reaching the critical point. He decided then and there to talk to Mel about his problem as soon as they were back in the car.

Other things from around the store also found their way into the cart. A pink Barbie clock radio, several girly pink towels and a whole stack of matching washcloths, a little girl’s pillow case and sheets. Chad had a pillow and a blanket but no sheets yet. He wasn’t exactly thrilled about her selection for him, but at the same time, it too was fueling his impossibly growing desire. So much so that his cock was as hard as the thick diapers he was wearing would allow him to get.

They came across a section of cheap furniture and Mel looked closely at the dressers and things. “I could really use something like this,” Chad mentioned.

“Yeah, I know,” Mel replied. “It would be a shame though to spend too much on something if you’re only going to be replacing it soon.”

“You mean since you’ll be replacing it soon!” Chad countered. “Along with a new pool table.”

“Dream on, baby, dream on. You ain’t gonna’ win!”

“Yes I will,” Chad replied, fully confident.

“Hey,” Mel exclaimed as she came across a set of four drawer chests. “Look, these are just cardboard and you can put them together easily. They should hold you for a little while.”

Chad would have much preferred something a bit better, but he had to agree that the cardboard furniture would work, and that it was practical. Unfortunately, Mel picked out two of the chests in white instead of the wood-grained pattern he would have preferred. But at least he would have something that resembled some furniture.

A whole assortment of cleaning supplies followed next. His shopping cart was beginning to overflow and was getting more difficult to push, especially in the heels he was wearing. Mel finally led them through the women’s department where Chad was more than sure that she would make his life more difficult, but Mel only looked at a few things and didn’t really spend much time there at all. Instead, she finally headed for the check out counters. Chad was more than glad, sort of.

The store was fairly crowded so they had to wait in line. Chad felt even more exposed as he stood there since he didn’t have any shelves around to hide behind and there were people all around him, all too close – all of whom were staring at him constantly. He felt so humiliated. The breasts sticking out prominently from his shirt, the all too red nails on his hands, and the high heels with his red toenails on his feet all seemed like flashing beacons to him, calling everyone’s attention to look… and to laugh at him.

It seemed to take forever before he could start unloading his cart while Mel just stood next to him and watched. He could feel everybody around him still watching him closely, especially the cashier. As he pulled item after item out of the cart, he realized that everything was for him, and it was all either very feminine things or baby things. All for him. All for his use alone. He was buying baby things and little girl things for himself to be using. And the very thought of it was making him hard again inside his diapers – at least as hard as he was capable of getting.

Chad reached for his wallet as the cashier was ringing up item after item. But that’s when Mel asked, “Do you have to pee yet?”

He did have to pee, but his mind was more on how horny he was instead of anything else and he unthinkingly he replied, “Yes.”

“Well do it now!”

She had said it so that everybody could hear. He heard someone sniggering behind him. How much humiliation can one person stand? He tried his best to relax and let the pee out, but it wouldn’t come.

“Well?” Mel asked. “Are you done yet?”

Chad shook his head.

“Hurry up!”

Chad finally realized what his problem was. He dropped his voice to a desperate whisper. “I can’t!”

“Why not?”

“Because I’m too hard! I can’t pee when I’m this way!”

Mel was so shocked she didn’t know what to do. Still wide-eyed at Chad’s answer she just watched while he paid for all the items. Then she silently led them back to her car where he put everything into her trunk. Once they were back in the car again, she asked, “So you mean, you can’t pee when you get hard?”

“That’s right. It’s physically impossible.”

“Not at all? And all that in there made you hard?”

“What do you think?”

Mel shook her head and just drove home. She had wanted him to announce to everyone around that he had wet his diapers again. But his little physical problem had gotten in the way. She had figured all along that despite everything she was putting him through, he was getting some kind of pleasure out of it. But she hadn’t thought it through to this point yet.

“Mel.”

“What?” She had barely heard him, lost in her own thoughts.

“I really need to get some relief. It’s been a few days now since I’ve been able to touch myself. I can’t do it with all this stuff you have me wearing.”

That surprised Mel, not that he couldn’t touch himself – that was kind of the point, but rather that he was asking for some kind of relief. “I’ll think about it,” she finally said.

As she continued to drive home, she thought about something else. What about her needs? She was excited about everything too. All the power she had and all the little humiliations she was putting him through were getting to her too. What about her needs? She had never had much luck with men. She had been engaged to be married twice, but the first one had chickened out, and she had ended the second one. But Chad here was not that kind of relationship. What about her needs?

The Bet - Chapter 7 (Friday - week 1 Part 1)

The Bet
by Karen Singer

Chapter 7 (Friday - week 1 Part 1)

Chad slept better than he had all week, even though he had to pee over and over again all night long. He was doing it so often now that he wasn’t even fully waking up when he did it. He did wake up fully several times when the suppository did its work, but there was nothing he could do about it and eventually he was able to go back to sleep again. All too early though, Mel was turning on his light and waking him up, which really was a shame because he had been dreaming about how deliciously humiliating it would feel to really be incontinent and the dream was keeping him super horny.

“Wake up Baby Chad,” Mel called from the doorway. But before Chad had gotten fully awake, Mel spotted the full baby bottle that was on the floor next to his mattress. She walked over and picked it up, as she did so, she noticed that the other bottle wasn’t completely finished either. “You’ve been bad!” she said picking up both bottles.

Chad was still trying to come to grips with having to be awake again. “What?”

“You’ve been bad,” she repeated. “You didn’t even finish one bottle and you were supposed to drink both of them!”

“Ugh! I was too tired,” he explained. “I fell asleep.”

“Maybe we’ll have to teach you to keep drinking in your sleep too.”

“That’s crazy. It’s impossible.”

“Is it? Maybe we’ll just have to see. We’re going to have to punish you for this, baby. Unfortunately, we don’t have time right now. But you can certainly look forward to it later!”

Chad wasn’t at all happy about that. He had no idea how she was going to punish him this time, but he already knew that he wasn’t looking forward to it.

As soon as Chad was once again dressed as she had been doing every day in his diapers, all-in-one girdle and pantyhose, she left him with the usual instructions to come back to her apartment as soon as he was finished getting ready.

A little while later, as Chad was laying on her couch finishing his morning bottle, Mel walked out of her bedroom and began removing his shoes. Chad was about to question her about it, but one look from her and he put his bottle back in his mouth and said nothing. He was quickly growing apprehensive though. As soon as Mel had both of his shoes off, she pulled his socks off too. Then, to Chad’s wide eyed amazement, she began putting his shoes back on him again. Chad began panicking, he wanted desperately to protest, but she was looking at him sternly in the eyes as if daring him to say anything at all.

All too soon, Chad found himself being pushed out her door with no socks on to cover up the pantyhose that showed at his ankles. What was he going to do? Things were already bad enough with everything else she had him wearing. Reluctantly, he got in his car and headed toward work.

But he didn’t go directly there. There was a drug store along the way and realizing it, he quickly pulled in. The store sold a few clothing items and among them were socks. He bought a pair and put them on in the car. Feeling much better, he finally continued on to work.


Mel had just finished with a client and stopped at Andrea’s desk to find out what was next on her schedule. “There’s a Mr. Comer is here with his business partner to see you. I put them in number 3. Oh, and a package arrived for you, I put it on your desk.” Then she continued in a more sing-song voice. “I think it may be whatever you ordered from that internet company. Although the package was a lot bigger than I expected.”

“Great!” Mel exclaimed, her excitement growing. “I ordered a few other things while I was at it. How much time do I have?”

“None, you’re behind again… but if you hurry, I think they can wait another five minutes.”

Mel hurried to her office. That’s the way her day usually went… hectic. But she had to take at least a quick look at what she had bought. Grabbing a pair of scissors, she quickly had the box opened. On top were several packages of large pink diaper pins, and several packages of very small padlocks. Under them were six packages of plastic panties, all of them with babyish graphics printed on them. Next in the box were several packages of white cloth diapers. They appeared to be very thick to her. Then, all the way on the bottom, were two final packages. She pulled them out to look at them more closely. Two special romper suits, technically very large onesies, that were supposed to lock onto him so he couldn’t get them off and couldn’t get at his diapers. She desperately wanted to open them and inspect them closer, but a quick glance at her watch told her she didn’t have time. She put everything back into the box and closed it. She usually worked through most of her lunch, but today she would be spending the time instead going more carefully through the box. She couldn’t wait.


Chad’s cell phone rang right at quitting time. He was still working at his desk though, waiting for most of the other workers to leave first. He was not surprised to see that the call was from Mel.

“Chad, don’t come to my office today. I’m already at your place waiting for you, so hurry.”

“My place?”

“That’s what I just said! Now get here, we don’t have a lot of time?”

“What’s going on?” But he got no answer. Mel had hung up.

As soon as he felt comfortable, he hurried out to his car where he pulled his new socks off and hid them in the bottom of the console. He knew without a doubt that Mel would never find them. Satisfied that he had found at least one small way to thwart her, he headed for home.

When he got through his front door, Mel seemed a bit impatient. “There you are,” she said as she hurried him through to his bathroom.

Chad noticed that she had already laid two diapers out on the floor for him. “What’s going on?” he asked.

“We have a lot to do tonight and I have an appointment first that I don’t want to miss, so we need to get you changed quickly.”

Chad was all for getting changed into clean diapers. A few minutes later, his diapers were changed and the all-in-one was firmly compressing his body once again, but when he reached for the pantyhose to put them back on, she stopped him. “Don’t bother with them tonight. You don’t need them.” That surprised him and he wondered more than ever what she was planning. Before he could put his shirt back on though, Mel stuffed a pair of rolled up socks in each of the bra cups of his all-in-one, giving him very protruding breasts. Mel had mentioned having an appointment, now he was really starting to hope that she would be leaving him at home.

He half expected her to hand him his dress to wear, but instead she had him put his shirt and pants back on again. His new breasts stuck out embarrassingly far, making his shirt seem odd. Before he could slip his shoes back on, Mel handed him a pair of his high heel sandals instead. Feeling more scared than ever, he buckled them on.

As soon as he was ready, Mel practically pushed him toward the door. “Now don’t give me any lip about the way you’re dressed,” she said sternly. “You’re wearing what I want you to wear and that’s all that matters.” Before he knew it, Chad was outside and following her downstairs towards her car. He wasn’t totally happy about it, but he did realize that it was certainly exciting.

As soon as Mel pulled out of the parking lot, Mel said, “I’ve been spending mostly my own money on you, but tonight, I plan on having you run up your own credit card a bit. I think that’s only fair since I’ve been buying you dinner and almost everything else all week. Chad wasn’t at all happy to hear that, not the part about running up his credit card so much, but the part he didn’t like was that obviously she was planning on making him go shopping dressed the way he was.

“So why the big hurry?” he asked.

“I have my weekly nail appointment in a few minutes and they said that if I can get you there on time they can take care of you too.”

Suddenly Chad didn’t know whether to scream or cry. All he knew was that he was scared. A few minutes later he realized something else too, he was incredibly horny again. As bad as things were with what she was making him do, he had to admit that overall, this was fun. He just wished he wasn’t so petrified. Damn the woman could be good sometimes.

Once inside the nail salon, Mel was greeted warmly by a tiny Asian woman. The woman then looked at Chad. “And obviously this is sissy?”

“That’s him,” Mel agreed.

“Ok, we get started right away. This way sissy,” she said as she turned and headed for one of the big seats along the wall. Chad counted six other women customers in the salon, all of them watching him curiously. He had no doubt that his face was very, very red, but what could he do about it? The woman had him sit down and then she took off his heels and had him put his feet into a pan of warm water where she began washing them. Chad did his best to concentrate mostly on just what was happening to him and tried to ignore everyone else in the salon. He noticed Mel was two chairs away having her feet done too.

The little Asian women didn’t say much to him, which was good because he wouldn’t have known what to say to her. He had done his own toenails many times, but had never had them done professionally in a salon before. He was surprised to see how quickly the little woman did everything. All too soon, Chad was watching her put dark red polish on his toes, followed a little while later by a clear polish. Then, while his toes were drying, he was led over to another table where the woman began working on his fingers too. Chad looked questioningly over at Mel, but Mel was only smiling wickedly at him. There were a lot more women in the salon now too, and all of them were watching him closely. More than one looked like they were going to burst out laughing at any moment. He felt so humiliated. He wanted so badly to crawl into a very deep hole and hide. But damn if it wasn’t making him even hornier.

He wasn’t sure if it was all too soon, or not soon enough that the woman was done with him and his shoes were back on his feet. But now the bright red nail polish on his toes seemed to call far more attention to the heels he was wearing. He didn’t even want to think about how noticeable the polish on his fingers was.

Mel was talking animatedly with the woman who was doing her nails. She called him over to her. “Let me see,” she told him. He held out his hands for her to look at closely. “Yeah, I like it. I think that’s the color I’m going to go with next time.” She looked down at his feet. “Don’t you just love how much prettier your feet are now? Sexy! Ok, go pay them. Oh and Chad, you had better leave her a really good tip and tell her how much you love your new nails!”
Chad wasn’t sure about that, but he did as he was told. “You’re very welcome,” the nail tech told him. We see you next week?”

Chad shrugged his shoulders. “I’m not sure.”

“We see you next week!” the woman said sounding very sure of herself.

Since Mel wasn’t finished yet, Chad had to sit in the waiting area till she was done. He took the only seat available since the salon was filling up fast. He realized now that that was why Mel had been in such a rush to get there earlier. The place got busy after a certain hour.

Every eye of every woman in there was on him the whole time he sat there, and he had nowhere to go. He felt like he was on display. Since Mel and the woman who was working on her were talking so much, it looked like she was going to take a lot longer to finish then his nails had. He wondered if she was doing it on purpose. He wouldn’t put it past her. The woman could be positively devilish sometimes. A little girl who had come in with her mother ran over and leaned down to look closely at his feet. “Red!” the little girl yelled. Then she ran back to her mother’s waiting arms. Chad really prayed hard for the ground to open up and swallow him.

The Bet - Chapter 6 (Thursday - week 1)

The Bet
by Karen Singer

Chapter 6 (Thursday - week 1)

Mel woke Chad up even earlier than she did the day before. Mostly because she figured that since he was going to be a smelly mess, it was going to be harder to handle and take longer. She wasn’t exactly looking forward to it, but dealing with the mess and the smell were just something she was going to have to learn to live with. It was a small price to pay next to what she was forcing Chad to endure. But there was no way she was ever going to lose this bet and she figured that the only way to win it would be to destroy all of Chad’s ability to control himself – totally.

Chad seemed to be at least a little more rested, but not a lot. “I kept having to go all night again,” he admitted. “But at least it’s starting to get easier.”

“Just think how much easier it’s going to be once you learn to do it in your sleep,” Mel told him again.

“Not likely!” Chad replied as he turned the shower head on his messy, smelly backside and let it soak him clean.

Mel dressed him exactly has she had done the day before, then left him to finish getting dressed with instructions to come back to her place again as soon as he was ready so she could give him his morning baby bottles. Then she went home again to get her own shower. She really did need to get him more baby bottles she decided as she filled the only bottle she had at her place. It would make this a lot easier. Maybe tonight. But that thought reminded her of just what else she had planned for the evening. And that was something she was really looking forward to.

Before she left for work, she did one more thing, she stopped into Chad’s apartment and found his copy of the contract and took it. She seriously doubted that he would ever know. On the way to work she dropped it off to have it off to have it framed. When the woman she was working with saw what was in it, she started laughing. “You can’t be serious!” she said.

“You can bet I am!” replied Mel.

“The woman laughed. It’ll be ready later this afternoon.”

When Mel finally walked into her office, Andrea was once again after her, wanting to know everything about how things were going with Chad. “Oh God,” she finally said when Mel had finished. You’re not going easy on him, that’s for sure.”

“I can’t afford to,” Mel replied. “I’m not going to lose this bet! Oh, and there’s something I need you to pick up and for me this afternoon and hold onto for a few days.” Mel explained what it was.

“No problem, I’ll get it for you,” Andrea replied. Then she filled Mel in on her schedule for the day. But before she finished, she added one more thing. “Oh, and your therapist, Gloria, called and wants you to call her back as soon as possible.”

Mel was surprised at that. She just hoped that Gloria wasn’t cancelling out on her. She picked up her phone as soon as Andrea had left. “Gloria, this is Mel. What’s up?”

“Hi Mel,” Gloria replied. “I’ve been doing a bit of research for what you want me to do with your friend, and I just wanted you to know that I don’t think this is something we can do in just one shot. I’m not a professional, I just dabble, but I still consider myself pretty good. I think I can at least help, but we’re going to have to start slow. Ok?”

Mel wasn’t all that surprised. “So what are you recommending?”

“That you move your weekly appointments to every Thursday night for both of you. That way we can build each time on what we did the week before.”

Mel was only slightly disappointed. But what Gloria said made sense. “Ok, I can do that. Are we still on for tonight?”

“Definitely. Tonight I just want to lay the groundwork. Make sure he can be hypnotized. I’ll set a few triggers and plant some suggestions, then hopefully next week he’ll be able to go deeper and we can plant some more.”

“Ok,” Mel replied. “I’ll go along with whatever you suggest.”

“Great. Now when you get here, I’m going to start the session normally, but at some point, I’m going to tap you on the arm. Then I want you to stop trying to follow my directions and just listen without saying anything. I don’t want to hypnotize you too.”

Mel laughed. “That sounds like a good idea.”

“When I start to bring him out of it, I’ll let you know. From there on, it should go more like normal. But Mel, most of the session is going to be directed at him. Understand?”

“Perfect,” Mel replied. “If this even helps, I’ll be very grateful.”

“Good. See you later then.”

Mel now couldn’t wait for her day of tedious work to end.


Chad had been a little more with it all day today. For some reason, while he hadn’t sleep thorough each time he had peed last night, he still hadn’t come fully awake either, especially later in the night. But now, as the afternoon wore on, he was starting to yawn all over again and was once again fighting to stay awake. At least this time he only had a few more hours to go. He was really wet again, but fortunately he didn’t think it was as bad as the day before. One thing he did noticed though was that the more he wet himself, the less worried he was becoming about doing it. But that fact didn’t worry him at all.

When quitting time finally came, he only delayed a few extra minutes before heading straight to Mel’s office once again. Andrea escorted him back to the same empty office again and brought him another coffee to drink while Mel was finishing with a client. But Chad hadn’t even finished his coffee before Mel came in carrying a bag with her.

“Ok,” she said being mostly all business. “Let’s get you changed.” Chad was surprised to see her pull two diapers out of the bag she had and lay them out on the floor. A little while later, his diapers were changed and he was feeling much better. He was still wearing the miserable all-in-one girdle again, but just having fresh diapers made a big difference.

“I’ve got a surprise for you tonight,” Mel explained. “There’s something I do every week that I absolutely love, and I’d like to experience it too. Trust me you’re going to love it.”

Chad wasn’t at all sure about that, but he didn’t have any choice.

As soon as she could get away from work, Mel drove them to a nice restaurant. Chad had only seen frozen diet dinners in her freezer and not much else. He realized that more often than not, Mel wound up buying her meals. The price of being a busy lawyer he realized. Mel was being particularly nice all during dinner and only insisted on him drinking three cups of coffee during their meal. Mel asked him quite a few questions about his job and his divorce and his finances. “You should have had your own lawyer!” she chastised him. “She took you to the cleaners!”

“What choice did I have?” he replied. “Under the circumstances.”

“A good lawyer would have helped.”

“Yeah right, like I’m going to tell some lawyer about what really broke up my marriage?”

“You told me,” Mel commented. “And you know for a fact that she told her lawyer. You messed up. And now you’re paying for it.”

“Yeah, but at least it’s a clean break. We have no kids and I’m not going to pay any alimony.”

“Yeah, but all you got was one of your cars and nothing else. She got everything.”

“But like I said, it’s still a clean break. I’m starting fresh from here.”

More than you know, Mel thought as she watched him finish his coffee. More than you know.

“So where are we going?” Chad finally asked as they got back into her car.

“It’s called relaxation therapy and I absolutely love it.”

Chad was a bit surprised. “I think I’ve heard of it, but I don’t really know anything about it.”

“Trust me, for a few minutes, every little care you have in the world will go away and you’ll feel so fresh and relaxed you won’t believe it.”

“Right now, all I feel is dog tired,” he replied.


Gloria was waiting for them and greeted Chad warmly, putting him immediately at ease. “Pick a chair and just relax,” she told him as she ushered them into her therapy room.

Chad was immediately impressed by the aura of the room. From the plants to the lighting, even the smell of the place seemed nice. Mel laid back on the chaise on the right so he climbed onto the one on the left.

“Now just relax and follow my instructions,” Gloria told him. “I know you’re going to enjoy this.”

Chad glanced quickly at Mel, she was already breathing in deeply, preparing herself for something she enjoyed. He decided to go along and try it. What could it hurt?

A few minutes later, Chad was feeling really relaxed and wonderful. As he listened to instruction after instruction from the therapist, he seemed to relax further and further. It was without a doubt, one of the more pleasurable experiences of his life.

Mel suddenly felt someone tap her on the arm and she jolted out of the reverie she had been going into. Just in time, she realized what was happening and didn’t say anything. Gloria was still talking, making Chad more and more relaxed as she went on. The process was fascinating. Slowly but surely she put Chad into a hypnotic trance, then kept trying to make it deeper and deeper. She planted suggestions for him to go immediately into a trance whenever she said certain trigger words. Finally, she started talking to him about his desires to wear diapers and his fantasy of being incontinent. She reminded him about how wonderful it would be and told him that he would dream about it every night, wanting it more and more. Finally, she told him that he wouldn’t remember most of what happened during their session. He would only remember the very beginning and waking up at the end, nothing in-between. Then Mel realized that Gloria was beginning to bring him out of it. Finally she got the signal and laid back and relaxed herself again as Gloria woke him up, still totally relaxed and feeling more wonderful than he ever had. The session was over. Mel didn’t know what extra Gloria was going to charge her for this, and now she cared even less. It had been fascinating!

“God that was great!” Chad remarked as they got up to leave. “I can see now why you love this so much.”

“Next week?” Gloria asked as they waked out.

“Definitely,” Mel replied.

“You mean we can do this again?” Chad asked.
“Every week, if you like.”

“Great!” Chad replied. “That was simply great!”

Mel didn’t drive then directly home. Instead she stopped at a store where they went in and browsed through the baby items. After looking at a number of different things carefully, Mel finally began stocking the shopping cart she had grabbed with baby bottles, lots of them. Chad hadn’t even been able to count how many she finally wound up putting in the cart. “That should hold us for a little while,” she noted. Chad was still shocked at how many she was buying, but he was also glad that she hadn’t bought any of the other things that she had been eyeing a little too closely.

They went directly back to his apartment after that where Mel had him remove all his male clothes. Then she added some rolled up socks to pad out the breasts of the all-in-one he was wearing and had him put a dress and heels on over top of it. Finally satisfied with the way he was dressed, Mel had him gather all his laundry that needed to be done and start carrying it to her apartment. Unfortunately, since he had nothing to carry it all in, it took him two trips. On the second one, one of the women who had seen him the day before was outside and she waved teasingly at him. He did his best to ignore her and to hurry.

Mel set him straight to work on her laundry first, then his laundry. In the meantime, she also had him cleaning whatever she could find around her house that needed it. She actually managed to keep him jumping from one task to another, all the while, making sure he was also drinking baby bottle after baby bottle of her green tea. By the time all the laundry was clean and folded, it was getting late and Chad was yawning over and over again. Unfortunately, the green tea was also making him pee over and over again too. He was now doing it so often he hardly even thought about it anymore. He was definitely getting a little too used to peeing without thinking about it – already.

While Chad was working, Mel cleaned a few of the baby bottles and filled them with the tea mixture. Some of them she gave directly to Chad while he was working, but others she fixed with tape wrapped around them so that Chad couldn’t empty them without her knowing it. When all the laundry was finally finished, she helped him carry all his clothes back to his own apartment where she inserted another suppository and rediapered him for the night. She finished her work off by making him once again wear his baby-doll nighty. Handing him two more bottles of tea to finish before he went to sleep, she finally left him.

Chad was exhausted. It also felt like he was peeing every twenty minutes and there was little he could do about it. He laid down on his blow-up mattress with the first baby bottle and began drinking it, but he was so tired that he couldn’t finish it. As he closed his eyes, he let out more pee. As he did so, he thought about his fantasy. It really would be so great to be able to sleep and not have to wake up every time he had to wet himself. They were pleasant and very stimulating dreams he had that night.

The Bet - Chapter 5 (Wednesday - week 1 Part 2)

My hopes have been dashed!

I almost had an adventure! For the last week, everybody here has been planning on me driving my in-laws and my wife out to Louisiana to stay for a week to take care of some business. That would have given me four or five days to dress and play. Just as everything was completely set and final, last night my mother in-law decided that they wanted to stay at home in Louisiana for at least a few more weeks. Possibly longer. So my wife will be coming home with me again and I won’t get to play!

My in-laws aren’t able to take care of themselves – and they know it. But suddenly my mother in-law is dragging her feet about moving in permanently with us. My father in-law thinks they already live here permanently. He’s so confused and getting more so all the time. I’m afraid it’s going to take another major episode for them to finally get it together enough to say bring us to your house for good.

I had really hoped to let you know today that I would be adventuring again soon. Now I’m beginning to wonder if I’ll ever have another adventure again.

Karen


The Bet
by Karen Singer

Chapter 5 (Wednesday - week 1 Part 2)

Andrea was working on the paperwork for another will when Chad finally came waddling into the office. She nearly burst out laughing just watching his straddle legged walk. The two clients that were waiting in the office were staring at him too. He looked horribly embarrassed. The poor guy was miserable, that much was for certain.
“Mel’s not back from court yet,” she told him as she got up from her desk. “She told me to have you wait in one of the offices in the back.” She led the way down the hall while Chad followed as fast as he was able to, which was really none too fast. The office she led him to had a beautiful leather couch. “I’ll be right back,” she told him.
Chad headed straight for the couch and laid down. He was so tired that he felt dizzy with relief when he did so. But before he could fall asleep, Andrea was back again – and holding a large cup of coffee in her hands.
“Mel wants you to drink this before you do anything else,” she told him.
Chad just looked at her. Did he have to do whatever Andrea told him to do too? Ok, so Mel had sent the instructions through her. He decided to err on the cautious side again and drink the coffee. As wet as he already was, it wouldn’t even matter if he had wet himself again. He took the coffee she was holding out for him and sipped it. At least it tasted good. Far better than the awful tea she usually made him drink.

“I almost hate to wake him,” Mel said a few hours later after she had finished with the last of her clients for the day.
“I know what you mean,” Andrea replied. “God, you should have seen him waddling in here when he arrived. It was hysterical.”
“I can’t get over it. Look at how bulky his diapers are, even compressed under that girdle. He better get used to it though because that’s just how I want to keep him. I’ll put him to bed early tonight. That part he’s probably going to appreciate.”
Mel left the room and came back a few minutes later with another cup of coffee in her hands. “He’s really going to hate me.” Both women giggled.
“Chad, wake up. Chad! Wake up!” Mel had to shake him a bit to break him out of his slumber.
Chad finally startled awake. “Can we go home now?”
“Just as soon as you drink this,” she said as she handed him the coffee.”
“Oh hell!”
Mel busied herself getting ready to go home while Chad finished the coffee. Chad was still bone-tired, but at least the coffee had helped wake him up a bit. “Go home and get yourself cleaned up. I’ll get some burgers for us for dinner, then I’ll be up to diaper you again as soon as I can.”
Chad gratefully went home. He was hungry, he was tired, and he had had enough to drink in the last few days that he didn’t ever want to drink anything ever again. And worse, the coffee was making him have to pee again. He sighed and relaxed as he wet himself yet again. Worse, he was beginning to feel the need to relieve himself in another way too because he hadn’t been able to get his diapers off earlier to do it. He had no doubt that that was going to be a problem tonight.
Getting his male clothes off was easy. Getting his pantyhose off wasn’t hard either. But that’s where the easy part ended. Just pulling the shoulder straps off from the girdle wasn’t easy. When he finally got them down, the straps had left deep, red, marks across his skin where they had been all day. He rubbed them to ease the pain. Then he had to struggle and struggle to get the rest of the girdle off. In doing so, he actually pulled his diapers and plastic panties off with it. There was just no separating them. But finally he was free from it all. He got into his shower and just soaked for a long time under the warm spray. He hardly even thought about it when he had to pee again and he simply let loose.
Mel rushed in as he was drying off. “Oh good, it looks like you didn’t have to wait too long for me.”
“I just now got out of the shower,” he admitted.
“When was the last time you peed?”
Chad blushed. “In the shower… I’m sorry, I know I shouldn’t have, but I just didn’t think about it. I’m really just too tired tonight.”
“Don’t be sorry. I’m glad you peed when you did.”
Chad was a bit confused, but he chalked that up to being so tired.
Mel prepared four diapers for him on the bathroom floor. Then she had him lay down on his stomach. She noticed that his backside was still a bit red from the night before. She was actually glad about that. She once again coated it liberally with the baby lotion. Chad was about to roll over again, but she stopped him. “Wait a minute.” She got up and went to a small bag she had in her purse from the drug store and brought out a small jar. She opened it and took out a glycerin suppository. Then she put the jar away again. Kneeling once again over Chad she said, “Now hold still.” Then she inserted the thing as far as her finger could reach.
Chad arched his back. “What are you doing?”
“Never mind,” she told him. “Just lay still.”
Chad didn’t dare move while Mel got up to wash her hands. He just couldn’t figure out why she had stuck her finger up his butt. When Mel came back, she rolled him over again and powdered him heavily. Then she taped all the diapers up firmly and put a clean pair of plastic panties on him. Chad was expecting her to make him wear the darn girdle again but she didn’t. Instead she dressed him in the baby doll nighty instead. After what Chad had worn all day, he actually felt very comfortable, even with four diapers on.
Mel picked out another pair of heels for him and had him put them on. Then she told him, “We’re going back to my place, and don’t you even think about giving me any lip about the way you’re dressed!”
Chad started to panic. But he had no way out. She practically pushed him out the door ahead of her. Unfortunately, several of the neighbors were walking up the stairs when she did it. Both of them women. Chad had no place to run to because Mel was right behind him, locking his door. The neighbors were staring and squealing with laughter. And Mel was standing there and smiling.
“What’s going on Mel,” one of them asked.
“Have you met our new sissy neighbor?” she asked.
“Oh, he’s just adorable, one of them replied.
“Oh he is,” the other one added. “He could use a little bit of makeup though.”
“And how about some nail polish too,” the other one added. They all laughed – except Chad who wanted to run – anywhere.
“Maybe next time girls,” Mel replied. Then she finally led the way to her apartment where she waved to the two women before she unlocked and opened her door.
Mel had picked up burgers for both of them and an extra large drink for Chad. She went straight to the kitchen and poured his drink into his baby bottle and handed it to him. “Get busy,” was all she had to say.
Mel made Chad sit on her kitchen floor while he ate, while she sat at her kitchen table and watched him. When he finished his first bottle, she grabbed it from him and refilled it again. “We’re going to have to get you more bottles,” she decided. She looked at how much more of the drink that she had bought him was still left in the original cup. “Maybe a lot more bottles.”
“Why can’t I just drink it from the cup instead?”
Mel handed him the second bottle, “Because I like seeing you drink from the bottles.”
Chad reluctantly put the thing back in his mouth and began sucking on it again.
He was just finished with dinner and on his third bottle when the feelings in his stomach hit him. Mel saw that he suddenly looked very uncomfortable and worried. A minute later a small cramp hit him and he definitely looked worried. “Feeling like you have to do something?” she teased.
Chad nodded his head as the intensity of the pressure quickly got worse. “Yeah,” he replied. Then he looked up directly at Mel. “Please! Please let me use the toilet. I have to go so bad I can’t stand it!”
Mel nearly laughed. “No! Never again. You know that. That little suppository I stuck up you earlier is simply doing its job. And that’s just one more thing you’re going to have to get used to. So I suggest you let it all out, because otherwise, obviously, you’re just going to suffer.”
“Suppository!” Chad grunted out. “Damn!”
“Watch your mouth! I don’t like swearing!” She watched as Chad struggled a bit more, then he started to get up. “No, no! Babies stay on the floor!”
Chad got back to his knees, but no further as the intensity became more than he was capable of handling. He had no choice, he let it all out into his diapers while Mel watched him totally fascinated. As he was nearly finished, he realized he had to pee too. He relaxed even more. He was so humiliated, he wanted to cry. This was something he had never done before and didn’t ever want to do again. When he was finally done and he had caught his breath, he looked back up at her again. “Please can I change myself now?”
“No,” Mel said again. Not till tomorrow morning. “Like I said, that’s something else you’re going to have to get used to. So I intend on giving you one of those things every night from now on.”
“Why?”
“Because I want to. No other reason necessary. Now sit back down and finish your bottle.”
Chad looked positively distressed. Sit back down? With what he now had in his diapers? But he had no choice. Very gingerly, he eased himself back to a sitting position. The feeling was not what he expected since the suppository had made everything come out so soupy. But it was fairly awful to him never the less.
As he brought his baby bottle back to his lips, she asked, “Did you pee yet?”
“Yes,” he nodded. “While I was doing the other.”
“Good,” she replied getting up from her chair. “Now finish drinking quickly, there’s still a lot more soda in this cup. And as soon as you’re done, you can go to bed.”
Bed! The very thought of it was like a beacon his soul had been searching for. It took two more bottles before Mel decided that he had finally had enough and let him get to his feet again. Mel noted how gingerly he was walking now that his diapers were messy. That thrilled her too. “I’ll be there tomorrow morning again to help you get dressed. I better not find any evidence that you’ve tried to remove anything. Chad didn’t answer. He was just too tired and humiliated, and just then more worried about going out through the door again in his present condition. But she held the door wide open for him and ushered him out.

Mel was catching up on some work she had brought home from the office a little while later when her doorbell rang. When she opened it, Cassie and Sandy, her two neighbors who had seen Chad earlier were standing there.
“Ok, dish girl!” Cassie said before Mel could even say hi. “What’s going on? We’ve been laughing about it ever since we saw him and now we just had to stop by and find out? Where is he?” she added looking in through her door.
“I sent him home to bed,” Mel replied, laughing a bit herself. These two girls had never come out and told her, but Mel had long ago pegged them as lesbians. They weren’t close friends, but they did see each other occasionally. Mel stood back. “Come on in,”
Neither of the girls needed a second invitation. “You sent him to home to bed?” Sandy asked as she walked past.
“Yeah,” Mel replied, “but he needed it. He hasn’t had much sleep in the past few nights now… and I’m afraid he may not get much tonight either.” While her two guests sat close together on her couch, Mel filled them both in on the details of the bet.
“I don’t believe it!” Cassie finally said, at which point, Mel got up and showed them her copy of the contract. “Unbelievable!” Sandy remarked as she read through it closely. “You should frame this thing and hang it on the wall.”
Mel’s eyes went wide. “That’s a great idea. I love it. In fact, I may do that to his copy too, so everyone can see it. Thanks.”
“So do you still call him Chad,” Cassie asked, “or do you have some other sissified name for him now?”
Mel was a bit surprised at the question. “No, I hadn’t thought of that. Really. I just call him Chad… But I like that idea too. But what do you think would be a suitable name for him now?”
The three women banded about name after name and laughed over most of them. But finally, Mel cut to the chase. After hearing name after name, one of them struck a note that she really liked. “That’s it,” she declared. “I’ve decided.”
“What?” both her guests asked at the same time.” Mel put a teasing look on her face. “I’m not going to tell you.”
“What?” the two girls said together.
“I think I’ll let him tell you himself.”
Cassie and Sandy both looked shocked. “I can’t wait!” Sandy said.
“When?” Cassie added.
Mel shook her head. “I’m afraid that’s going to have to wait for a while. There are other things I need to do to him first before I change his name.”
“Oh come on,” Cassie complained.
“You’ll just have to wait. But I promise you, when the time comes, you’ll be the first ones to know.”

Chad laid down on his inflatable mattress in misery. He had to pee… again. He barely gave it a second thought. Damn the woman. She was constantly coming up with more and more things to make his life miserable. But he was so tired he could barely think straight. He fell asleep, for a while. But all the liquid she had once again forced down his throat was waiting to get out. For the first time, he didn’t bother to roll over onto his back to do it like he usually did, he just let loose. It was easier. He immediately went back to sleep, for about half an hour. Then he had to pee again. Later still, the suppository did the rest of its work.