The Bet - Chapter 34 (Thursday – week 5 Part 3of 6)

The Bet
by Karen Singer

Chapter 34 (Thursday – week 5 Part 3of 6)

Chad’s phone didn’t ring nearly as much after break, but it did ring occasionally. And the longer his morning wore on, the less it seemed to ring – something he was very grateful for. The women seemed to be running out of guesses – he hoped.
He glanced at the time on his computer screen. He still had a few minutes left before lunchtime. He thought he could hear Robin typing on her keyboard in the next cubicle. The timing seemed to be safe enough. He opened the spreadsheet on his desktop where he kept his progress toward the bet and quickly found today’s date. Twenty-nine days to go! Seeing the number finally reach less than thirty seemed like a major milestone and made the amount of time left seem even less. He would win this bet! He still had no doubt!
He moved up a row to yesterday’s date and filled in his best time that he remembered being able to hold back yesterday – only nineteen minutes! Two minutes less than the day before! Once again he was going backwards. It seemed like all the increased drinking along with Mel’s enforced diaper wetting games were taking a toll on him. If he didn’t get busy and manage to hold it longer again, then Mel might still have a chance! But still… nineteen minutes wasn’t so bad at all, was it?
His eyes caught sight of the column of things that he wanted – his reasons to win the bet. He had relayed many of them to Sandy last night so she could design his apartment for him when this was all over. He couldn’t wait to see what she came up with. It was going to be great! He glanced again at his best time for yesterday. Only Nineteen minutes! He quickly closed the spreadsheet before he could get disgusted with himself.

“Sissy!” the receptionist’s excited voice squealed the moment he walked through the door to the gym.
“Uh… Hi,” he returned.
She pouted. “Come on, you can do it nicer than that.” And then she giggled a bit even though she was trying to keep a stern look on her face.
Chad didn’t miss any of it. Knowing it was no use resisting, he dropped a curtsey and said, “Hewwo,” in his sissy voice.
The receptionist giggled uncontrollably. The look of absolute delight was all over her face. She leaned across the high counter as much as she could. “Can you lift your skirt so I can see what you’re wearing underneath?” She giggled again.
Chad mentally groaned. Why couldn’t she just go get Cassie for him? But he knew she probably wouldn’t let up till she got her way, so he pulled his skirt up high.
Her face registered nothing but disappointment. “I can’t see much of anything with those blue hose on today. They do look nice, by the way.”
“Uh… Thanks,” Chad replied as he smoothed his skirt back in place again. “Can you get Cassie for me now?”
But she didn’t leave just yet. “When do you ever wear anything where I can see your diapers?”
Chad was fairly shocked by her question. He shook his head. “Never. I’m almost always very well protected when I leave the house. Especially for work.”
The receptionist’s lips pursed in thought as if she was bothered by something. “Never?” she asked.
“Never!” Chad confirmed. “I’m afraid that Mel has some very strict requirements for me.”
“Mel is the woman who was with you on Monday?” She still looked bothered by something.
“Yeah.”
“You know. It’s a lot more fun when you talk silly instead of in your normal voice.”
Chad mentally groaned again. “Can you please just go get Cassie for me?”
“Not until you ask in your silly voice,” she teased. Her eyes suddenly glowed with interest.
Chad was getting frustrated. At the rate things were going, he’d be here all day before he got to see Cassie and get his diapers changed. “Can you pwease get Cassie fow me now?” he asked in his sissy voice.
Her eyes glowed with delight. “Now curtsey pretty as you ask me.”
Chad wasn’t sure if he wanted to run out the door or hit her. Having little choice however, he dropped his curtsey and repeated his request.
The receptionist giggled again with delight. “Oh, that’s so much better!” she teased. “Okay, I’ll find Cassie.”
“Thank you,” Chad said.
“Uh-uh! Curtsey please!”
Chad felt like hitting her more than ever! But instead, he curtseyed yet again as he repeated his thank you.”
Her eyes showed nothing but delighted mischief as she finally walked off to find Cassie.
Chad had to wait a few minutes before they returned. As he was waiting, two women came out to leave. Unfortunately, one of them recognized him right away. “Oh! Look who’s here!”
Chad’s face turned red as the two suddenly delighted women walked right up to him. “We so enjoyed your little visit the other day!” one of them said.
Chad just nervously nodded. “Thank you,” he replied, rather embarrassed.
“Are you coming back to do it again?” the other one asked hopefully.
Chad shook his head. “I hope not.”
The two women laughed a bit. “Well, we just wanted you to know how much we enjoyed it. It was quite a show you gave us.”
“I know I’ll remember it for a long, long time,” the other woman added.
That wasn’t exactly what Chad wanted to hear. “Thanks,” he mumbled yet again. He was ever so glad when the two women just said goodbye, one of them giving him a tiny wave with her fingers. Women! He watched them as they both walked out of the gym.
“You’ve made some friends,” Cassie’s voice said, causing him to turn quickly back around.
“Not really,” Chad replied.
“It sure looked like it to me. They didn’t complain about you, did they?”
“No.” Chad felt a bit of disappointment over the fact that they didn’t complain. “In fact, they both told me how delighted they were to see me.”
Cassie nearly laughed. “See, like I said, you’ve got some new friends.” Chad wasn’t so sure at all.
A little while later, Chad was drinking from another baby bottle while Cassie was removing his sodden diapers. As usual now, Cassie took careful note of the size of his penis inside his chastity device. Just as small as ever. “Does that thing ever get hard anymore?” she asked.
Chad stopped drinking only long enough to answer. “It can’t,” he replied. “That thing won’t let it.”
Cassie realized that she had only asked something obvious. “Well, does it ever get any bigger inside there?”
Chad stopped drinking again. That was a different question. “I don’t really know,” he replied. “It’s always covered up with my diapers. I can’t see it. All I can really tell you is that at least it doesn’t seem to hurt me like it used to. I don’t think about it as much anymore.”
Cassie nodded and went back to work on him as she tried to completely digest what he had just told her.
Chad was also trying to digest what he had told her, but from his point of view. What he had just said was the honest truth. He didn’t think about it that much anymore. Getting harder, or bigger, while wearing the chastity device was not an option, it only brought pain. He was so glad that he hadn’t felt any pain from there in a long time now. In fact, the chastity device didn’t allow him to feel much of anything from that part of his body anymore since the plastic cover prevented him, or anything else, from even touching his penis. The only thing he could say that he felt there anymore, was pressure. Not so much the pressure from where the device was locked onto him, but a deeper lingering pressure that was more inside of him. The pressure from having no sexual relief in such a long time. His entire life was nothing but major sexual stimulation, while he was entirely denied the reward of relief. Frustration! Pure and simple frustration!
“Okay,” Cassie said. “Roll over. Let’s do your other side now.”
Chad set his baby bottle aside and rolled over. A moment later, he was feeling the wonderful sensations of Cassie’s hands spreading the lotion all over his backside. Would she play with him again today? There hadn’t been time yesterday. He felt her hands leave him again.
“Scootch your knees up for me,” Cassie said.
Chad felt nothing but elation at her words. A moment later, he felt the hard tip of her toy as she placed it against him. He was a bit surprised that she didn’t start with her fingers today, but he really didn’t care. Her toy was the closest thing to having sex that he was capable of feeling – even if he couldn’t ever get any true release from it. The moment she started to push on it, he opened himself up and pushed back again. He wanted that toy inside of him. He wanted to feel it going in and out of him. He wanted to feel… excitement!
Cassie was a bit surprised at how fast he took her dildo today. She had purposely not worked her fingers into him before she used her toy. But today, he was obviously ready for it… and obviously wanted it. She had seen it many times before, but today he seemed to work himself up to a very excited state very quickly. “Does that feel good?” she asked.
Chad barely registered her question, he was too intent on the feelings in his bottom. “Uh huh,” he grunted as he kept up his pumping, trying desperately for the release he wanted.
“Is it as good as the way you used to have sex?” Cassie asked.
Her question floored him. His pumping slowed quickly as he thought about it. Then came to a stop altogether. He was glad that Cassie had left her toy up inside of him so he could still feel it. But her question bothered him. Did it feel better? Or not as good? He honestly didn’t know. Worse, he honestly couldn’t remember how it felt to have sex the other way… the normal way. Especially not with her toy still in him, still stimulating him. With her toy still there, that was the only part of him that felt any pleasure. It was too hard to think about anything else. “I don’t know,” he finally replied. “I honestly don’t know.”
Cassie wasn’t sure if she was surprised by his answer or not. In a way, she was sorry she had even asked the question, but in a way, she wasn’t. She had been genuinely curious. And whether he believed it or not, she honestly felt some sympathy for the poor guy. She felt him pulling away from the device she was still holding against him, then pushing slowly back into it again. He pumped himself a few more times then stopped, his head slumping to the floor as if he were defeated. She knew he was done and pulled it all the way out of him again. Had her question spoiled the fun for him? She hoped not. But then, why should it matter to her anyway? She told herself that it didn’t.
Frustrated, in so many ways, Chad rolled back over again so she could rediaper him and grabbed his baby bottle. There was a comfort that very few people probably knew about in sucking on a bottle – well, except for real babies that is. Cassie’s question haunted him. Did it feel better, what she was doing to him – or for him? Or was it better the old way, the normal way? And why couldn’t he really remember how it felt the old way? He tried to chase the question out of his mind by concentrating instead on the feeling of Cassie diapering him while he sucked on his bottle – like an infant. More and more of an infant. Exactly like he had been thinking earlier that morning.
Cassie watched him as she grabbed the jar of suppositories and opened the lid. He wasn’t watching her again. Instead, he seemed to be lost in his own thoughts. She didn’t even bother to take the lid all the way off this time. As she had done many times now, she stuck only her finger up inside of him, pretending to stick one of the little gems way up there. The look on his face as she did it was certainly not pleasure. She knew that he hated the darn things. But the strangest part was that he really couldn’t tell when she was faking putting one into him or not. “Do these things still work?” she asked.
Chad’s face registered nothing but disgust as he pulled the bottle out of his mouth. “Too well!” he replied, then stuck the bottle back in again.
“Do they work every day?” she asked, curious to know if there was a difference in the days when she only pretended to do it to him.
“Every damn day,” he replied, the frustration of it clearly in his voice. “Just once, could you try not putting one into me… and not tell Mel about it? Please?”
“Sorry, I can’t do that,” she replied. He made no answer, he only looked away from her again as he sucked on his bottle. He couldn’t tell when she wasn’t sticking them up into him, and now it looked like whether she did or not was having exactly the same result. Was Mel really winning here? She couldn’t be sure, but it looked like she might at least be making some headway.

“Thanks, Cassie. I appreciate it.” Mel hung up her phone and sat back to think for a minute. What Cassie had just told her really wasn’t anything new. Not really. But it did confirm her suspicions – or hopes – or both.
She found it odd though that he didn’t know if he ever got any bigger inside his chastity device than he seemed to be lately. She figured that guys, with their odd piece of flesh hanging off of them, would always know what it was doing. Especially since it was supposed to be so sensitive. But did the chastity device cancel out any of that sensitivity? She wasn’t a man, so she really didn’t have a clue.
And as to him not knowing if the anal sex was a good as his old ‘normal’ way, well, she was fairly sure that he knew the answer to that one too. Of course it wasn’t! Was he just trying some kind of ploy in hopes that she would relent and let him feel sex like a man again? If so, he was going to be very disappointed!
And as to the suppositories working whether or not they were in him, well, she pretty much already knew that. But it was nice to have some extra confirmation.
All in all, so far, things were going mostly pretty good. Now if only she could solve his peeing problem so he couldn’t hold back at all anymore. Of course, Gloria could probably solve that in a few minutes, but Gloria was refusing now. She had been forced to settle for a compromise with Gloria that she wasn’t really all that happy with.
She was trying to win this bet, and in some ways she knew that she was winning. She just wasn’t so sure about the one main part, the only part that really counted – making him completely incontinent.