The Bet - Chapter 42 (Friday – week 6 Part 3 of 8)

The Bet
by Karen Singer

Chapter 42 (Friday – week 6 Part 3 of 8)

Chad was becoming a bit concerned. He had only been able to try holding back a few times so far today. What concerned him the most, was that he just realized that he had peed again – without knowing he was going to do it. He was fairly sure that he hadn’t peed much at all this time, but still, he had almost totally missed it. And not for the first time today.
Too much to drink! He knew without a doubt that that was the problem. He had already had an extra cup of coffee that he didn’t usually get in the mornings – and that was on top of the unusual amount he had guzzled all last night. Way, way too much to drink. If he didn’t start cutting back on the amount he was drinking now, then Mel was going to win for sure! He promised himself that he wouldn’t drink anything at all when he ate lunch. That should help – he hoped – because right now, it almost seemed like Mel was winning this bet, and he couldn’t dare let that happen. He had to find a way to fight back harder. But how?
He stared reluctantly at the blank page on his computer screen. What was he supposed to write? Why did he “deserve” to be incontinent? He had to come up with something. He “wanted” to be incontinent – just for the humiliation of it. But that didn’t mean that he “deserved” to be incontinent. Besides, he “wanted” it – outside of the bet. For the bet, he didn’t want it. Or did he? Well, he did, he just couldn’t allow himself to be that way – yet.
Confused, he opened up his favorite web search program and typed in a query for reasons to be incontinent. He briefly searched through the pages it brought up – and found nothing – nothing that he could use to indicate why he “deserved” to be incontinent.
Frustrated, he closed the search program and stared at his screen again. He finally began typing, but it was only the title. He had written it just in the hopes that it might inspire him. But so far…
Still having no clue what to write, he again opened up his web browser and typed the word ‘fashion’ into the search program. Looking at what the fashion models were wearing was a lot more interesting than trying to write an impossible paper.

“No! I’m not going to do it!”
“Oh come on. Be a good sport,” Ray replied as he sat down on the edge of Derek’s desk.
“Being a good sport has nothing to do with it,” Derek replied as he looked up at Ray from his chair. “Especially in this case!”
“But it’s the proper thing to do.”
“Bullshit! And you know it!”
“Well I think you should,” Ray urged.
“Well I think I won’t! And that’s final. It’s bad enough I have to go out with him!”
“Her.”
“Him!”
“Ray smiled. “Don’t be a bad loser.”
“Well stop being such a gloating son-of-a-bitch winner! I’m not going to do it. So get that stupid thought out of your head!”
Ray got back to his feet. “Okay. Have it your way. I’ll pick you up on Sunday.”
“Unfortunately!”
As Ray headed back toward his own office, he mused, “Well, if Derek didn’t want to do it – willingly, then he’d just have to find a way to make it look like he did!” He smiled as several possibilities came to mind. Poor Derek. Riding his case and spreading gossip about him and Sissy was so much fun.

Chad pulled into the parking lot of the gym and parked his car, but he hesitated before getting out. If he didn’t need changing so badly he would have been tempted to skip coming here today. He wasn’t at all sure how Mel would feel about that, but somehow, he figured that she wouldn’t like it. Having little real choice, he got out of the car and grabbed his purse and diaper bag.
Cindy watched through the glass door as Chad walked across the parking lot toward the door. As a receptionist, she got to know more of the customers that came in than most of the other employees. But by far, the one that interested her the most was Sissy. According to Cassie, he secretly loved all the humiliation that got heaped on him. She couldn’t really understand why, but she had to admit, she enjoyed seeing the silly things he went through. And knowing that she too could tease him and humiliate him only added to her interest.
Her only problem was that Cassie had just told her she couldn’t “help” with him again today – not even watch. But Cassie had left her a possible opening.
“Not today,” Cassie had said. “Not unless he specifically asks you to.”
So now Cindy had just one thing on her mind, getting Sissy to ask her to “help” once again. “Hi Sissy,” she called brightly the moment he walked through the door.
Chad mentally groaned. Why did she have to be so cheerful? It had to be a very bad sign. What had she and Cassie cooked up to do to him today? Knowing that he wouldn’t get away with not greeting her properly, he dropped his usual curtsey and said hello.
Cindy giggled. There was just something about seeing him do that, that thrilled her all the way down her spine – right down to her toes. She leaned excitedly across the counter. “Can I change you again today?”
Chad was caught off guard by her question. She had asked that yesterday, and when he told her no, she had somehow turned things around so that the decision was taken away from him. “I don’t have any say in the matter,” he replied somewhat flatly.
“So that means I can be there?” she asked excitedly.
“Wait a minute! Is Cassie really giving me the choice this time?”
Cindy backed off, no longer so excited. “Maybe,” she replied noncommittally.
But Chad was grasping at his own straws. “If that’s the case, then defiantly – no!”
“But I did a good job yesterday,” she argued. “I didn’t even hurt you when I put that silly little pill up inside of you.”
Chad shook his head. “I’m sorry, but if I have any say at all in this matter, then I’d rather it be just Cassie. Will you find her for me please?”
But Cindy wasn’t about to give up yet. “Well then can I just come in and watch? Please?”
Chad shook his head again. “I’d rather you didn’t,” he replied politely but firmly.
“Oh pooh!” Cindy pouted. “I’ve been looking forward to it all day.”
Chad was suddenly wondering if he had just won this battle. Unfortunately, he couldn’t take anything for granted. “I’m sorry,” he replied. “But like I said, I’d rather it be just Cassie. I’m more comfortable with just her.”
“But if I’m there, then you’ll get more comfortable with me too!”
“I’d rather not!” Chad replied. “Now will you please find Cassie before I start leaking all over everything here?”
“Darn it!” she said as she sullenly left her post to go in search of Cassie.
Chad watched her leave, split between celebrating his victory over her and worrying about what Cassie might say when she came back. Fortunately, he didn’t have long to wait. He dropped another curtsey and another sissy hello as Cassie entered the gym foyer.
“Are you ready?” Cassie asked.
Chad noticed that she didn’t ask anything about Cindy. “Yes,” he replied as he shifted the weight of his diaper bag strung over his shoulder.
“Then let’s get busy.”
Surprised that there was no mention at all of Cindy, he followed Cassie back through the gym, noticing as he went that Cindy just went back to her post behind the front desk – rather sullenly, but she went back. But the question now was, would she stay there?
Back in the little office, Chad started to undress while Cassie laid his things out. By the time he was down to just his diapers, plastic panties and waist cincher, she had everything laid out and ready. She handed him his bottle as he laid down on the floor. As he put the bottle to his mouth and started drinking – and Cassie began removing his plastic panties to change him, he was struck by one thought – just like old times! This was the way it was supposed to be – private! Just Cassie and himself. Thankfully. And somewhere in the back of his mind he prayed it would stay like that, because it was always possible that Cindy could come in at any time.
Cassie unfastened his overly saturated diapers and pulled them down. “Somebody’s been wetting an awful lot this morning,” she declared as she did so. “I noticed that the inside of your plastic panties are a bit wet too. It’s a good thing you had them on.”
Chad didn’t doubt for a moment that he had leaked a bit this morning. It was only just a little while ago that he had begun getting back into the swing of things with really being able to hold back. Granted, he hadn’t been able to hold back very long… yet. But hopefully, that would change this afternoon. He had no intention of getting anything at all to drink with his lunch today. Hopefully, that should help a lot!
Cassie glanced at his tiny plastic encased organ as she wiped his front side and applied a bit of baby lotion to his skin. His trapped penis was just as tiny as it always was. She had to wonder if the thing ever grew anymore. But a quick glance at the wicked looking spikes just touching his skin on the inside of the device made her remember that he needed to stay as small as possible. It was the only thing that prevented those spikes from causing him major pain. She had seen him writhing on the floor more than once because of those spikes. She quickly slipped his soaked diapers out from under him and inserted two new ones in their place. “Okay,” she said. “Time to roll over.”
Chad set his bottle down and rolled over so she could do his backside. Would Cassie “play” with him today like she used to? He was really hoping she would. It seemed like so long ago since she had last done it, and he missed it – the only little bit of fun he seemed to get anymore. The feeling of her hands as she massaged the baby lotion into his backside was pure heaven. He shut his eyes and concentrated on it. And when he heard her telling him to “skooch his knees up,” the feeling of anticipation he felt in his stomach was almost painful. He couldn’t wait.
It had been so long now since he had been able to get any sexual relief at all. Never had he been allowed to orgasm since this whole bet started. He was kept painfully chaste with no chance of ever getting hard. And then stimulating thing after stimulating thing had been thrown at him – for so long now that his body seemed to react to the stimulation on the inside, but his under exercised organ no longer seemed to respond at all. And if by some chance it did, then he was very sorry for it almost immediately. So much so that he instantly wished he would never try to get hard again. But if feeling the excitement on the inside was all he had left, then it was far better than nothing, and now he couldn’t wait to feel Cassie’s usual toy that she used on him… at least he hoped she would use it on him.
The feeling of her finger starting to play with his asshole sent shudders of pleasure and anticipation all through him. He couldn’t wait to feel her pushing it in. But she was still holding back, teasing him, building his anticipation. He briefly wondered what Cassie did when she and Sandy were together. And for that matter, what did Sandy do to her? But those thoughts were instantly banished the moment her finger actually slipped inside of him. He held his breath for a moment as she pushed it in, then pulled it back out. In then out. Deeper, then shallower, then deeper still, then shallow. Over and over. He never knew how far in she was going to push it in.
And then her finger was gone completely and he heard her opening the desk drawer to get her toy. And that was the moment he realized that he had to pee again. He had to practice holding back! That was very important. He clamped down hard on his muscles, trying to do whatever he could to build up his strength there.
And then he felt Cassie’s hands again… and the tip of her toy playing with his anal hole. He felt her trying to push it in, pushing harder and harder. But with all his muscles locked the way they were, she couldn’t do it, she couldn’t push it inside of him! But he wanted it in! But he had to hold back!
“What’s wrong?” Cassie asked. “You don’t want it today?”
“Yes I do. Badly!” Chad replied.
“So what’s wrong?”
“I have to pee! Badly!” he replied.
“Oh.” Cassie wasn’t sure what to do. She pulled her dildo away. “We’ll just try another time,” she told him.
“No!” He wanted it too badly. He needed it too badly. The question was, could he possibly relax his anal muscles enough to let her get it inside of him – while at the same time manage to hold back from peeing? “Try it again,” he told her. “But go slowly.”
Cassie was a bit surprised, but she was willing. She put her toy back up against the little hole in his backside. “Ready?” she asked.
It was a moment before Chad felt he had enough control over things to nod that he was ready. Relaxing the muscles of his backside ever so slightly, he prayed that he would be able to hold off on peeing. He felt her pushing harder, then harder. He relaxed more and more. The rounded tip penetrated him further and further, but not fully. And then, almost suddenly, it went in, right past the first few ribs on her toy. He felt totally jubilant as he felt her slowly pushing it further and further up into him. And then she was pulling back on it again. And he was still holding back on his pee. Slowly in, then slowly out. Over and over, faster and faster, harder and harder. His attention now was completely on the wonderful feeling of her toy going in and out of his backside. He closed his eyes again in pure bliss!
Cassie watched him closely. Things were now almost back to normal again. He was slowly working himself into a little frenzy over the feelings he was experiencing. And then out of the corner of her eye, she noticed something odd. Then it happened again. She had to bend over to watch more closely to see if she was right. And she almost laughed. Every time she pushed in on her toy, he squirted a little bit of pee out of his chastity device. Almost like a little squirt gun. And it didn’t look like he even knew it! Over and over again, just a tiny bit each time. And it kept happening and happening. It was causing quite a little puddle on the diaper that was just below it. Fortunately, the diaper soaked everything up fairly quickly.
Chad was in heaven. But eventually, he reached the point where there was just no use continuing anymore. It was that total frustration point where he knew that the release he wanted so badly just couldn’t be obtained. Frustrated and disappointed, he stopped, but not before he pushed back and forth just a few more times for that last bit of enjoyment.
“All finished?” Cassie asked before she withdrew the toy.
Chad tried to look back at her, which was difficult, and nod. “Yeah,” he replied.
“How about peeing? Are you done with that too?”
Peeing? Had he leaked? He was still trying to hold back! He was still working hard at it! “What do you mean, am I done? Did I leak a little?”
“You’ve been peeing since we started!”
Chad was shocked. “I have?” He did his best to look down under him and saw how wet part of the diaper on the floor was. Ugh! He had leaked.
“Well, are you done yet?” Cassie asked again as she pulled the toy fully out of him.
“No, I’m still holding back.”
“Then why don’t you just let it go and finish what you started so we can get out of here.”
Still in the same position, Chad relaxed his muscles to let the rest of his pee out, but what came out amounted to only a little bit of a dribble before it finished. So frustrating! He had failed totally.
“Are you done now?” Cassie asked again.
“Yeah, I guess so,” Chad replied rather sullenly.
“Then roll back over so I can get you diapered up again.”
“Aren’t you going to replace the one I just wet all over?”
“Why? You wet them a lot more than that every time you come in. I’m sure you’re used to it. Besides, that’s the inner diaper that I went to all the trouble to cut slits in. I don’t want to do that again to another diaper.”
Reluctantly, Chad rolled over and set his backside down on the already wet diaper. He could feel the wet spot high up near the back of the diaper as he set his backside down on it. So much for starting the afternoon of in dry diapers. It was just a good thing he enjoyed them being wet!
Cassie grabbed the jar of suppositories and made a show out of opening it and pulling one out. She showed it to Sissy. “I know you just love these things, don’t you?” she teased.
Chad mentally groaned. “Just for once, can’t you please leave it out? Please?”
Cassie shook her head. “Sorry. These little beauties are one of the main reasons Mel wants me to change you every day. Lift your knees up for me.” Once Chad was in position, she pushed his legs up further, once again exposing his backside that she had just finished playing with a minute ago. Palming the suppository in her hand, she stuck only her finger way up inside of him. Once again, he would never know what he didn’t get… and hopefully, he would never see any difference.