The Bet - Chapter 25 (Tuesday – week 4 Part 3 of 6)

The Bet
by Karen Singer

Chapter 25 (Tuesday – week 4 Part 3 of 6)

It was still fairly early when Mel picked up her phone and called Cassie. “Hey Cassie,” she said as soon as Cassie had answered.
“Hi Mel. What’s happening? Still on for tonight?”
“Definitely!” Mel replied.
“Great! I know Sandy will be happy. She’s been working really hard for this.”
“I know. She told me.”
Cassie giggled. “Yeah, I know. So what’s up?”
“Cassie, I need you to make a tiny change in what you’re doing with Chad at lunchtime.”
“Sure, what?”
“Well, on Tuesday’s and Thursdays don’t put any suppositories up inside of him… but I need you to pretend you’re doing it so he doesn’t realize you’re not putting them in him.”
“Huh? Just pretend to do it?”
“Right!”
“Well, if you’re sure…”
“Yeah, please. But don’t forget. Keep putting them into him all the other days.”
“Ok,” Cassie agreed. “That should be no problem.”
“Thanks, Cassie. I owe you.”
Cassie giggled. Yeah, you do. See you tonight.”
“Yeah, Cassie. See you tonight.”
Mel hung up her phone. The next phase of her plan for Chad was now in effect! She opened her laptop and started working again, but her mind was still more on Chad and whether or not she really had the reason she thought she did last night to punish him. And because her mind was more focused on Chad, she was getting further and further behind on her work in the office.
Her work was further interrupted close to noon when her phone rang again.
“Hey girlfriend,” Gloria’s voice said over the phone.
“Hi Gloria,” Mel replied happily. It was good to hear a friendly voice once in a while.
“Lunch today?” Gloria asked.
“Ummm… Can’t today,” Mel replied regretfully. “Too much to do.”
“Ok, sorry girl. Maybe another time.”
“Yeah, definitely,” Mel replied. She was about to hang up when she found herself quickly saying, “Hey Gloria!”
“Yeah?”
“Hey, listen. Do you have a minute to talk?”
“Yeah, sure. What’s up?”
Where should she start? “It’s about Chad. I went at him again last night, punishing him a bit… Oh, and hey, you know he actually started crying! Like a baby! Completely!”
“He did? So it’s working then? The suggestions are working?”
“Yeah. They seem to be working great. Although I did notice he’s not quite completely incontinent yet. But he didn’t have a whole lot of control and wound up peeing on my carpet a little bit.”
“Hey Mel. That kind of brings up something I wanted to talk to you about. The next time you come in, I think I want to try something different with him, ok?”
“Like what?”
“Well, I kind of want to see what’s working and what isn’t. That way we can make changes to whatever isn’t really working, now rather than later.”
“Sounds great to me,” Mel replied. “You know I’d like as much info as we can get too.”
“That’s kind of what I thought. So I’ll work on what I want to do with him for Thursday night then.”
“Sounds great, Gloria.”
“So listen, Mel, what were you punishing him for this time?”
“Ugh! That’s my problem. I don’t really know if I should have, or shouldn’t have.”
“So maybe we should have lunch together after all?”
Mel thought about it. “Maybe I can juggle a few things around. Make it a quick lunch anyway.”
“Great Mel. See you in a few?”
“See you in a few.”

Chad had done next to nothing all morning… except to wet his diapers four more times and try to time himself – fourteen minutes so far. The two cups of coffee he had drank with Robin didn’t help things any. He was wetter than usual as he tried not to waddle too much out to his car. The worst part of it was though, that the extra wetting seemed to be irritating his diaper rash even more. He was very disappointed that all the baby lotion he had put on it earlier wasn’t helping much… if at all. As he climbed gingerly into his car, he made it a point to ask Cassie to put extra lotion on him when she changed him today.
He pulled into the parking lot at the gym and grabbed his purse and diaper bag. He glanced around as he got out of the car, at least Robin wasn’t there today, she had made arrangements to go to lunch with the woman they had talked with earlier in the break room – whatever her name was.
He walked through the door to the gym. The receptionist, as usual, was smiling broadly at him. “Hello, Sissy,” she said with more zeal than he was really happy about. Then she stood there smiling at him… waiting.
There was no getting around it gracefully and he knew it. He dropped a quick curtsey to her and said, “Hi.” She seemed satisfied though because she immediately giggled and went in search of Cassie.
Chad had to repeat his curtsey-greeting once again for Cassie as soon as she got up front, then he followed her back to their usual back office. “How are you today, Sissy?” Cassie asked as he started to get undressed.
Chad stopped removing his pants for just a moment. “Hurting a bit,” he finally replied.
“Hurting? What’s wrong?” she asked with some concern.
Chad looked a bit embarrassed. In fact he sounded embarrassed as he quietly answered. “I seem to be coming down with a case of diaper rash… and it’s getting worse.”
“Diaper rash!” Cassie repeated a lot louder than Chad was happy about. “Oh you poor thing. Let me see.”
Chad continued to get fully undressed down to his diapers and plastic panties. Then Cassie handed him one of the baby bottles out of his diaper bag to start drinking while she undressed him the rest of the way. As soon as she had untaped his diapers, she pulled both legs up toward his stomach. “Leg’s up. Let’s see how bad it is.” Chad dutifully attempted to keep his legs pulled up, but Cassie helped him hold them up and out of the way. “Hmmm. Yep, it’s all red. You’ve got a nice little rash started there.”
“I put a lot of baby lotion on it this morning, but it doesn’t seem to be helping.”
“You may have to get something special for it later. All I can do for it is to put more of your baby lotion on it again, but if that’s not helping yet, then I think you need to get something better.”
“Isn’t there anything you can do for it?” Chad asked hopefully.
She shook her head as she let his legs drop. “Nope. Besides, I’m certainly no expert on the subject. I’ve never had a baby… or even been married for that matter. Not that I’m probably ever going to either. Don’t you have any friends somewhere who’ve had kids? You should ask one of them. I’m sure anyone who’s had kids can tell you how to cure this.”
As Cassie began pulling the fresh diapers under him, Chad thought about who he knew that had kids. Unfortunately, the only one who immediately came to mind was Robin – his one and only friend. But Robin didn’t know about his diapers – and he meant to keep it that way. As Cassie began massaging the baby lotion into the front part of him, he sucked on his bottle, deeply in thought. How could he get Robin to tell him how to cure diaper rash without telling her that he wore diapers? And did he dare?
Cassie shook her head. “This is starting to be a waste of time. You don’t even know I’m playing with you here. Talk about no reaction. Ok, turn over.”
“But I hurt!”
“Tough! Turn over!”
Chad wasn’t at all happy about that, but he put his bottle down and assumed the position for her to work on his backside… the only part of him that seemed to feel anything remotely like sexual pleasure anymore.
Even though Cassie’s hands were coated liberally with baby lotion, the moment they touched his diaper rash, he hissed in pain and tried to move away. “Darn,” she said, “you’ve got it bad, don’t you. “It hurts a lot?”
“What do you think?” he returned angrily. “Yes, it hurts a lot! And I think it’s been getting worse all day!”
“Well, you’ll just have to suck it up, because I’ve still got to get the lotion all over you. Besides, you wouldn’t want to go without any, would you?”
“No,” Chad replied flatly.
As gingerly as she could, Cassie finished coating his backside with the baby lotion. She didn’t massage it in as she usually did because she didn’t want to cause him anymore pain than she had to.
But she wasn’t quite done with him after that. “I brought a present for you today,” she said with a little chuckle. Chad didn’t answer, but he did try to roll onto his back again as if he thought she was done with him. “Uh, Uh!” she said as she stopped him from rolling over. “You stay just like that!”
Chad wasn’t sure what she was talking about. A present? And she didn’t want him to roll back over? From his present position he couldn’t see anything.
The shock was instantaneous and electric. Cassie couldn’t help but giggle as she watched his whole body react the moment she placed the tip of her dildo, right up against his tiny asshole with more pressure than usual. She only kept it there for a brief moment before she applied even more pressure and began pressing it in.
It took Chad a moment to realize what was happening before he could relax his muscles enough to start to accept the toy she was using on him. He certainly hadn’t been expecting it. But once he fully realized what it was and what she was doing, he relaxed more and tried to “get into it.” He still didn’t know why, and it still really bothered him, but he loved it and he wanted more, more, more!
Unfortunately, very shortly into the experience, while her toy was buried deep inside of him, he realized that he suddenly had to pee. Yes, he wanted to feel the pleasure of peeing while the thing was in him! But no, he didn’t want to be peeing all over everything again… and worse, with her toy reaming him out but good, he knew for sure that he couldn’t hold back for long. “Cassie!” he called out with a bit of distress, “I have to pee!”
“So go ahead,” Cassie replied. “I already put fresh diapers directly under you.”
Chad wanted to argue against wetting the fresh diapers before they were put on him, but there wasn’t time. As Cassie pulled the dildo out, then pushed it in once again, he couldn’t hold back any longer. The pee came gushing out of him, into the short space available inside of his chastity device, and continued gushing straight out of the device to fall directly into the diapers below.
He heard Cassie giggling as he did it. Laughing at him! Damn! And worse, he knew he deserved to be laughed at. Damn! And worse still… because she was pumping the dildo in and out of him, and because he was peeing during it, and because she was laughing at him, and because he felt humiliated by it all… it completely fueled his sexual need to an unbearable degree. Damn he needed some relief. But there was no relief in sight. Nowhere! He wanted to pound his fists on the floor from the frustration of it all. But it would help nothing. He was trapped into Mel’s chastity hell! And so far, there was no way out! Thirty eight more days? It was way too much!
Getting relief! The only solution he could see for the near, and distant future, was to win the bet! As Cassie finally slowed down, his mind was locked firmly on his reasons for winning the bet. Forget all the reasons for losing that he had been thinking about all morning… he now had another reason for winning the bet – relief!
He finally felt Cassie pulling the dildo completely out of him. As much as he had loved the feeling, he gasped in relief. “Hold still another minute,” she said. Chad heard her fussing with something, then he felt her finger pushing into his hole once again as far as she could reach it. The damn suppository. He hated the damn things… and especially what they did to him.
Chad rolled back over and grabbed his baby bottle and began drinking it without hardly thinking about what he was doing, he was that used to it now. He felt Cassie pulling the diapers under him up and over him, which surprised him a bit. “I just wet those,” he complained.
Cassie shook her head. “They feel hardly wet at all. Not enough to worry about as far as I can see.”
Surprised, and disappointed, Chad stuck his bottle back into his mouth and sucked on it. Diaper rash or not, he was already starting the afternoon with wet diapers!

“Your jealous!” Gloria declared.
Mel rolled her eyes, then looked down at the table. “Totally,” she admitted. “But geez, shouldn’t I be?”
Gloria shrugged, “It’s only natural.”
“So what should I do about it? He’s got to work with her… every day!”
“Have you met her? Talked with her?”
Mel shook her head. “Not yet.”
“So why don’t you?”
Mel thought about it, then shook her head again. “Not yet. I’m just not ready for that yet. I mean, it’s probably perfectly innocent. They’re just working together.”
“But you don’t know that for sure.”
Mel shook her head and sighed. “No, I don’t know that for sure.” Just then, Mel’s cell phone rang. “Oh hell, probably more problems,” she said as she fished it out of her bag. But she smiled a bit when she saw the call was from Cassie. “Hi Cassie. How’d it go?”
“Hey Mel. It went fine today. I faked putting the little pill in him and I know he couldn’t tell I wasn’t doing it.”
“Great Cassie. I appreciate it. Now remember, none on Tuesdays or Thursdays, but do it every other day.”
“Got it Mel… Hey Mel. You know his rash is really hurting him. I think you’re going to need something more than the baby lotion he’s using to try to clear it up.”
“Rash? What rash?”
“The diaper rash all over his backside. You don’t know about it?”
“No, not at all. He didn’t tell me.”
“Well, I’m surprised because it looked like it was getting pretty bad.”
Mel paused to think. “Ok, Cassie. Thanks for telling me. See you tonight.”
“Great Mel. See you then.”
Mel hung up her phone. “He’s got diaper rash.”
Gloria stared at her in surprise, then giggled. “Well, you did want to make him more babyish. What could be more babyish than that?”