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.