The Bet
by Karen Singer
Chapter 29 (Saturday – week 4 Part 7 of 9)
Chad wasn’t thrilled about having to do it… he wasn’t thrilled about having to do a lot of things… but by his own figuring, he had little choice but to pull one of the baby bottles full of Mel’s tea out of his diaper bag and start drinking it in the car. He had already had enough bottles today to float a boat, but if he didn’t keep drinking them, then he didn’t know how he could possibly manage to overflow his diaper in the allotted time left. And by now, he did want to make it leak. He had been punished, severely, so many times already today that he would do almost anything to avoid getting any more. So despite the fact that anyone who happened to look into Mel’s car would be able to see him sucking on the bottle, he put it to his lips and kept drinking.
He didn’t know where they were going. Mel had only said shopping, and he certainly wasn’t going to ask anything else. Besides, since she had limited him to only baby talk, he had no way to possibly ask her for more details. He was however only mildly surprised when she pulled up in front of the same store where they had shopped in the past for most of his clothes.
“Don’t forget your pacifier,” she reminded him as she got out of the car.
Chad wasn’t exactly pleased to hear that. Taking one last desperate pull on his baby bottle, almost as much for courage as for the liquid it held, he quickly slipped his pacifier back in his mouth, grabbed his purse and followed Mel into the store. Sucking on the pacifier out in public like that was extremely humiliating. And once again he felt all too plainly the resulting sexual charge coursing through his body because of it. A charge so great, he could almost feel Cassie’s toy sticking up into his backside as he walked.
Once again, Mel led him straight to the women’s clothing section he had spent so much time in before. As they walked through it, he was almost as concerned this time with trying to keep peeing as he was with paying attention to how many people might be looking at him. His desire to keep peeing was rewarded when a few minutes after they entered the store, he felt himself wetting his diapers again. Relief! Because every time he wet himself today, it not only felt good, but it brought him one step closer to not getting punished.
Mel spent a few minutes walking around searching – not for clothes, but for the same saleswoman who had helped them so much in the past. And eventually, she found her. The woman was surprised to see them. She gave Chad a quick glance, but since he looked pretty much the same as the last time she had seen him, her gaze didn’t linger on him for more than a second, except for the pacifier in his mouth. After greeting Mel warmly, she asked, “And what can we find for you today?”
Mel turned and looked back at Chad. “I’m afraid she’s lost a bit of weight and a lot of her clothes don’t fit anymore. She’s going to need two more pairs of slacks for work and I think a couple of dresses too. And this time, I think we should make the slacks fit a bit better. What do you think?”
The saleswoman grinned as she looked Sissy over more carefully again. “Definitely!” Then she looked a bit bewildered. “Is it my imagination, or has ‘she’ lost some weight around her backside too?”
Mel almost laughed. “I’ve got her in only one diaper today. So I guess we better plan on making sure there’s enough room for one or two more.”
The saleswoman nodded and said, “That’s probably a good idea.”
Chad soon found himself in one of the dressing rooms pulling his dress off while the saleswoman and Mel went in search of some new pants for him – something he was very glad about. He was just disappointed that Mel had specified only two pairs. He really needed more. He was waiting patiently in just his bra, waist cincher, diaper, and shoes, when the curtain suddenly opened. He jumped at the sudden intrusion, but he was glad to see the saleswoman there holding several pairs of slacks. He was very embarrassed to be seen by her in his wet diaper, but there was little he could do about it. He did notice however that she spent a very long moment staring directly at his diaper. She smiled at him before she took a step back and closed the curtain again. Whew!
As he pulled the first pair of pants up, he immediately noticed that they weren’t cut as full as the other pants that he owned. In fact, they seemed to fit much tighter – certainly not too tight, but enough that he noticed it. He knew that Mel would be waiting to see them, so he opened the curtain and stepped out. He stood where Mel and the saleswoman could see him perfectly and waited for their comments. The saleswoman was eyeing the pants critically, but Mel didn’t look as if she had even looked at the pants yet. She was staring at him, and moment by moment, the anger on her face seemed to increase. “That’s one demerit for not curtseying when you came out!” she said sternly. The saleswoman looked at her in surprise, and so did Chad. Another demerit? Ugh! Would there be no end to them? “And that’s another one for not curtseying now that I’ve reminded you!”
Chad got the point and immediately dropped a curtsey and mumbled a bit of apologetic baby jargon through his pacifier.
“What did she say?” the saleswoman asked.
“Who knows!” Mel replied like she didn’t care in the least. “Do you think there will be enough room in those slacks later, when she’s wearing more diapers?”
The saleswoman looked at the slacks Chad was wearing critically. “I’m sure of it. They’re really not all that tight on her at all. Most girls wear them a lot more fitted!”
Mel nodded. “I know. Unfortunately, for her, we don’t have quite that luxury. But still… Tighter might be interesting to see. Do you have some that she can try on, just to look at?”
“Of course! That’s easy,” the saleswoman replied as she hurried off.
“Go take them off,” Mel told Chad. “We’ll bring you some different ones.”
This time, Chad was careful to drop a curtsey before he went back to change.
Once again, the curtain to Chad’s dressing room opened all too suddenly. This time, both the saleswoman and Mel were there. The saleswoman had several pairs of pants in her hand, but Mel interrupted her before she could hand them to Chad. “Excuse me,” Mel said as she stepped inside the dressing room. “I need to check something first. Are you still wetting?” she asked Chad.
Chad was careful to drop a curtsey and mumble something in his baby language. He pulled his arms out of the way and let Mel see his wet diaper. Mel didn’t just look at it, she grabbed the front of hit and squeezed a bit. She smiled. “Keep at it,” she said as she backed away again. Relieved, Chad curtseyed once again and mumbled still more baby talk.
“I can’t understand anything she’s saying with that pacifier in her mouth,” the saleswoman complained.
Mel smiled as she selected one of the pairs of slacks from the saleswoman’s arms and handed them to Chad. Then she closed the curtain. “There’s a good reason why you can’t understand her today.” She then explained Chad’s new talking requirement for the day to the incredulous woman.
A minute later, Chad stepped out of the dressing room again, this time in some very tight fitting pants. This time he curtseyed as soon as he got out. He didn’t want to get any more demerits that would cause him any more punishments.
“I was careful to find some that weren’t low-rise,” the saleswoman told Mel, “just to keep her diapers a bit more hidden. Of course, I can’t guarantee that they won’t show at all, especially when she gets a little more… um… wet. And I think this pair that she’s got on is a bit stretchy too.”
“Are they stretchy, Sissy?” Mel asked Chad.
Chad dropped a curtsey and mumbled something stupid, thinking all the time that it was stupid for him to even try to answer. Nobody was going to understand him anyway.
“What did she say?” the saleswoman asked.
“I don’t know,” Mel admitted. “I just love seeing her try to answer.” Mel studied the pants critically. “I do have to say that I like them though, even though the front crotch doesn’t look quite as feminine as the ones that hide more. But still, that may not be such a bad thing either.” She turned back to Chad. “Turn around so we can see how they fit in the back.”
Chad wasn’t sure if he was supposed to drop a curtsey first before he turned around or not, so he dropped a quick one. But before he could turn around, Mel stopped him. “Wait a minute!” she said. “Before we see the back, curtsey again, and hold it.”
Chad was a bit surprised at her request, but he dropped into a curtsey and stayed in that position while Mel and the saleswoman watched.
“I’m thinking that they’re definitely the stretch pants,” the saleswoman said.
“Yeah,” Mel agreed. Even in that position they look pretty good. “Go a bit deeper,” she ordered Chad.
Chad was already getting tired holding the position. It wasn’t exactly an easy one to maintain. But he dropped a bit deeper and again held it. But as the women discussed the fit of his pants, he suddenly felt himself peeing once again. In the position he was in, he was praying his diaper wouldn’t leak, even though leaking wouldn’t be bad in another way.
“Okay,” Mel finally said, turn around for us now.
But Chad wasn’t finished peeing. He wanted to move, but he was afraid to even stand up yet. Mel saw the look of worry on his face. “What…” she started to ask, and then it hit her what was probably going on. She laughed. “Are you wetting again?” she asked.
Still holding his curtsey, Chad mumbled something while the pee finally finished and he stood back up.
“Good baby,” Mel replied with a slight giggle.
“I hope you’re buying those slacks,” the saleswoman said as Chad turned around so they could see the back of them.
“Don’t worry,” Mel replied. “They were sold the minute I saw her in them. She’ll take that pair and the first pair she tried on too.” The saleswoman seemed satisfied with that. “Now,” Mel continued, “how about some dresses?”
Chad sat in the dressing room with nothing to cover his odd underclothes for a very long time. At any moment, he expected Mel or the Saleswoman to open the curtain and hand him something to try on. But so far, he was forced to sit and wait. In desperation, he finally poked just his head out from the curtain to see if they were out there, but he saw no sign of them at all, so he went back and sat down again. The thought that Mel had abandoned him there started to run through his head more and more. What would he do? And should he get dressed in his maid’s uniform and go and find out if she had left him?
Knowing, or more like hoping, that she hadn’t left the store yet, he continued to wait. He even managed to wet his diaper once again while he waited. Afterwards, as he looked down at it, he was shocked to see how obviously soaked it looked – from the outside. He knew it was totally saturated on the inside too. He doubted… no, he hoped… that it couldn’t hold much more. But so far, there was no sign of it leaking. He didn’t know how much longer he had to go before his time limit would be up, but that deadline had to be approaching soon.
He finally heard voices outside his dressing room and the curtain was pulled aside abruptly by Mel. “Here,” she said handing him two dresses still on their hangers. “Try these on.” Chad didn’t even get a chance to do more than grab the hangers before she was gone, closing the curtain behind her.
The first dress he had to try on was a black and white, zebra print dress with a fairly low cut neckline. He stepped into it and struggled to zip it up the back. It hugged his body perfectly. As he looked at his reflection in the mirror, he thought it seemed to make his shape look even more feminine. He stepped out of the room to show it to Mel. Once again he curtseyed for them and mumbled some baby nonsense as soon as he got out of the dressing room.
“Oh, I like that one,” Mel said as he stood there. “It’ll be just perfect for her for work.”
A surge of embarrassment ran though Chad at her words. Wear it to work? Well, wasn’t he dressing as a woman there already? Why should he be so embarrassed by it? Besides, it was a really nice dress. He was thrilled to be just trying it on.
“Ok, the other one,” Mel instructed.
Chad curtseyed, then disappeared into the dressing room yet again. The second dress was hard to describe. It was all colorful splotches of varying shades of greens and browns and yellows and black, all run together. It had a wide gathered scooped neckline and like the first dress, came down to his knees. He went back out to show the women and quickly got the approval for it too. He was very relieved to get back into his maid’s dress once again because it meant that he didn’t have to try on any more clothes. Hopefully, they could leave and go home now.
He carried his new clothes out of the dressing room and handed them over to the saleswoman.
“That’s another demerit!” Mel’s voice angrily lashed out. “You didn’t curtsey to her or thank her for helping you!”
Ugh! Three demerits already. Thirty swats from her stick. Ouch! Once again Chad curtseyed, this time to the saleswoman, and he mumbled a bit more mumbo jumbo around the pacifier in his mouth. The way it was looking, Mel expected him to curtsey and greet absolutely everybody!
“You’re welcome,” the saleswoman replied to his baby talk… I think.”
“Can you hold these things at the register for us? We have a little more shopping to do.”
“Certainly, the saleswoman replied.
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