The Bet - Chapter 35 (Friday – week 5 Part 4 of 8)

The Bet
by Karen Singer

Chapter 35 (Friday – week 5 Part 4 of 8)

Chad was miserable. More than miserable. He didn’t want to play poker with the guys – at least not till after he won the bet. As he walked back toward his desk, he kept trying to imagine what she would do to him there. He could just see himself showing up at the game in one of his sissy dresses… maybe even the one that was so babyish and didn’t even begin to hide his diapers. For that matter, would Mel make him wear only one diaper there, with instructions to make it leak before the night was over? Talk about embarrassing! And then there was his stupid sissy voice that she was so instant that he use all the time… as if he could! He could just see the guys all laughing at him over that! Or maybe she’d dress him up like a slut and somehow talk them into playing strip poker… with instructions for him to lose – and eventually he’d be down to just his diapers. What then? Embarrassing! And while his friends all drank from beer bottles, would he be drinking from baby bottles? Damn!
Maybe it would be better to just tell her that George had said no. But the minute he thought that, he pictured himself being abandoned at work wearing nothing but a pink ballet costume. Nowhere to run. Nowhere to hide. As humiliating as the thought was, and it did kind of turn him on, he knew he could never manage coming to work that way. He would have to find some way to convince George to let them both in the game.
Still picturing himself in a pink ballet outfit, he opened up the company phone book and found George’s number. He sat down hard in his chair, then quickly got back up again and almost angrily pulled his skirt out from under him before he sat back down again. Damn! The things women had to put up with! A minute later, he was listening to George’s phone ringing. Maybe George wouldn’t be there. Maybe George was home today. Maybe he’d have a good excuse for not getting into the game that Mel would approve of. And maybe he’d be wearing a tutu to work next Wednesday! It was almost with relief that he heard George’s voice finally answering.
“Hey George. This is… Chad.”
“Hey Chad. What’s up?”
“Uh, you know that poker game you’re holding next week… Are you still having it?”
“Of course. Why?”
“Um… I know this sounds strange, but… I really need to be there… Me and a lady friend of mine!”
“What?”
Chad could just picture how annoyed and angry George probably was. “Please, George. Please. It’s important.”
“Important? Why?”
“Trust me, it just is. To me anyway.”
George paused for a moment. “I don’t know Chad. I mean, the games are just for the guys, you know? Heck, you’ve been to some of them yourself! And you don’t exactly qualify as a guy anymore.”
Chad knew it was true. He knew it, but it still hurt to hear. “I know, I know! But please, I’ve got to be there.”
“Chad… or is it Sissy… you’re not a guy anymore. You can’t come!”
“We’ll bring the beer!” Chad replied quickly, trying to force the issue.
George paused again. “I thought you didn’t drink beer.”
“I don’t. Not usually anyway. I’ll bring my usual soft drinks too.” Inwardly though, Chad was wondering if he would be bringing baby bottles instead. He heard George pausing again. “Please, George,” he pleaded almost pathetically. “I really want to be there.”
“Who’s this lady friend you want to bring?”
There was no way Chad could tell him that Mel was his Mistress. Although he had no doubt that if they did get into the game that George would find that out fairly quickly. “Uh… she’s just a friend. A good friend.”
“Uh huh. I see.” George wasn’t at all sure what it was that he saw though.
“Please,” Chad pleaded again.
George sighed. “Look, Sissy… or Chad… whatever! I don’t think it’s going to happen, but I’ll ask the other guys and see what they say. Okay? That’s about the best I can do.”
Progress! At least he wasn’t totally saying no anymore. “Thanks George... Hey! Who’s playing?”
“Just Derek, Ray, and Steve… and me of course.”
Chad did some quick thinking. Maybe he could appeal directly to the other guys. “Why don’t I ask them about it, personally?”
“No way!”
“But, I mean, it is my problem. I could handle asking them so you wouldn’t have to bother. I’d be glad to do it.”
“Not just no… but hell no! I’ll ask them myself! I don’t want to hear about you whining about your little problem from them… whatever your little problem really is.”
“Thanks George. I owe you. Please try to convince them.”
“I’ll ask, but I’m not so convinced myself.”
“Thanks, George. I appreciate it.” Chad was about to hang up when he heard George’s voice again.
“Hey Chad!”
“Yeah?”
“This lady friend of yours. Is she good looking?”
“Very!”

Robin stared at the top of her cubicle wall, not sure she believed what she had just heard. It wasn’t that she had been really trying to listen, but he had gotten louder and louder the longer he had talked. Mostly anyway. Before she knew it, she was on her feet, heading for his desk. “Hey Sissy,” she said as she entered his cubicle.
Chad turned around, knowing instantly that Robin had heard his phone conversation.
“Did I hear you asking to get into George’s poker game?”
“Yeah,” Chad admitted sheepishly.
“Why?”
Chad searched for an answer. He couldn’t tell her what Mel had threatened him with, but that did lead him to another answer. “Because I made the mistake of mentioning the game to Mel, and now she wants to be there.”
Robin tried to digest that for a moment. “Wow, you must really like her then.”
Chad just shrugged, but offered no answer to her question.
“So is George letting you in… even though I thought it was a ‘guys only’ thing?”
“I don’t know yet.” He sighed. “Right now, it doesn’t sound like it.”
“So what’s Mel going to say if George says no?”
“Knowing Mel, she’s not going to be happy at all!”

Chad was a bit hesitant as he approached the door to the gym. He just knew that the receptionist would try to make him do something humiliating again – no matter that whatever she asked him to do was usually mild compared to other things he had done elsewhere. And if he didn’t do whatever she asked, then Cassie would find out… and if Cassie found out, then Mel would soon know it. There was just no winning. Reluctantly, he opened the door and went in.
“Hi Sissy,” the receptionist called brightly.
“Hi,” Chad returned, reluctantly. “Will you please…”
“Oh come on! Can’t you greet me nicely? You know how I mean.”
Here we go, Chad thought. Reluctantly, he dropped a curtsey to her and using his sissy voice, again said hello.
She giggled. “That’s much better. Thank you.”
“Now can you…”
“Hey,” she interrupted him before he could finish asking her to get Cassie. She leaned as far across the counter as she could toward him. “Are you wearing diapers again?”
“Yeah. That’s kind of why I’m here.”
She giggled again. “What do they feel like?”
Chad was shocked. “What do they… They feel bulky and wet!”
She giggled once more. “Real wet?”
“Yes real wet!”
“And you said bulky?”
“Yeah, very!”
“Because you wet them so much?”
Chad was getting fairly exasperated. Where was this going? “Yes!”
“So you really wet them a lot this morning?”
“Just like I always do!” Chad was beginning to get a bit more angry now.
She tried to lean further across the counter. “Can I feel them?”
Chad was shocked once again. “Can you… No! Besides they’re all covered up under my other clothes. You know that. I can’t even get to them without a lot of trouble.”
“No,” she replied quickly. “I mean, can I just feel around your bottom? From the outside?”
She wasn’t giving up, and Chad knew that if he didn’t let her then she’d tell Cassie.
“Okay,” he finally agreed… If… you get Cassie for me afterwards.”
“Of course,” she giggled as she hurried out from behind the counter.
Before he knew it, she was pulling up his skirt all around. “Hey!”
“Shhh! I’ve got to get close enough to feel, don’t I?”
Chad wanted to tell her that she didn’t have to get close at all, but he held his tongue and let her have her way. She held his skirt high up out of the way with one hand while she felt all around him with her other hand, at times, pressing firmly to see just how bloated his diapers were. She even tried to feel him directly under his crotch.
“Geez,” she said. “I can tell you’ve probably got diapers on under there, but everything is packed so solidly on top, that I can’t really feel much at all.”
“That’s kind of the point,” Chad replied.
“Oh pooh!” she said as she dropped his skirt. Then she giggled. “Still, it was fun.”
“Are you going to get Cassie now?” he asked.
She smiled. “Of course!”
Chad was very glad to see her go. He smoothed his skirt back all around the minute she was out of sight. Women!
As soon as Cassie got there, Chad quickly dropped another curtsey and greeted her. He was anxious to get on with his changing and away from the receptionist. “Hi Sissy,” Cassie replied, sounding almost bored. “Are you ready? Let’s get this over with.”
Chad followed her back to their usual small office and began undressing while she started pulling diapers, suppositories, wipes, and a baby bottle out of his diaper bag. As usual, it took a few minutes for him to get out of his dress, shoes, pantyhose, all-in-one girdle, and finally the plastic panties – till all he had on was his waist cincher, glued on breast forms, and his diapers. It was a lot of trouble to go through every time he needed to be changed, but then that’s the way that Mel wanted it.
He laid down on the floor and Cassie gave him the bottle, which he stuck directly into his mouth and started sucking on the nipple. The liquid felt good against the back of his dry throat. He didn’t have to look to see what Cassie was doing, feeling was just as good. Within moments, he felt her pulling open the tapes that held his diapers tight against him. Then he felt the front of his bulky, soggy diapers being pulled down through his crotch, exposing his damp bare skin to the open air… well, almost bare skin, his chastity devise did cover some of it.
He felt the cold shock of the baby wipe as she wiped off everything on his front that she could reach. Unfortunately, she couldn’t touch the one main thing there that he would like touched, the part of him trapped inside the chastity device – the part he tried not to even think about anymore - the part that had wanted so much to give him relief from his sexual frustrations, but was denied any ability to do so – the part that Mel had rendered – useless!
“Lift up a bit,” Cassie requested.
Chad lifted his bottom off of the floor and felt her pulling the soggy diapers out from under him. Quickly, he felt her shoving two new ones back in their place.
“Okay, Sissy. Roll over.”
Chad set his bottle down and turned over onto his stomach, his freshly wiped front side now resting on the fresh diapers under him. He remembered when Cassie had spent more time on his front side, trying to get a response out of his trapped penis. How long had it been now since she had done that? He couldn’t really remember, but he didn’t think it had been all that long. Of course, he hadn’t had any kind of response to her touch in quite a while now. For that matter, he didn’t remember that part of him responding to anything anymore. Somehow that seemed a bit humiliating to him and something touched and stimulated his deeply rooted sexual need that resided in his whole body now. But that stimulation did nothing to the one organ that it used to affect.
The feel of the baby wipe wiping his backside felt better than it did on his front. There was more open flesh there to appreciate being cleaned. Despite the cool wipe being rubbed all over his exposed flesh, he felt the shock of the colder baby lotion as she began wiping it thickly all over him back there. He closed his eyes at the pleasure. The cold lotion quickly warmed to his skin temperature as her hands slid smoothly over his bottom. All of his bottom. Then closer to his asshole. Closer still. Till suddenly he felt her finger there… then it was gone.
He couldn’t see what she was doing, but he hoped he knew. It took a few moments.
“Scootch your knees up now,” she requested.
Yes! This was the part that he was waiting for almost as much… no… maybe more than the joy of clean diapers. He felt the point of something hard touch his asshole. It wasn’t shock that ran though his body the moment it touched him, but it was a closely related feeling. He wanted that device of hers… he wanted it up inside of him. Without realizing it, he opened his bottom up wide, trying to do everything he could to accept the toy she was using on him.
He felt her pushing it slowly inside… oh, the feeling! He felt each of the tiny little ribs on it going into him – each one adding a slight bit of extra pressure as it passed through the opening in his bottom. He was tempted to just thrust himself against it, but he held himself firm, letting himself enjoy the slow buildup of pleasure this time. Then she was pulling it out, just as slowly. He felt the little ribs of the device going out now, feeling just as good as they did going in. Without pausing, she was pushing it back into him now, pushing harder, faster. Then out again, just as hard. Then in… then out… He couldn’t stop himself if he tried. His body was suddenly doing the thrusting – in and out. Back and forth! Over and over. Trying – vainly – to reach that unreachable pinnacle of sexual release.
It seemed to go on forever, yet as good as it felt, he couldn’t get there – couldn’t achieve what his body longed for so badly. Sadly frustrated, he slowed his actions, slower and slower… then stopped. As hard as he tried, it was useless. He just couldn’t do it. He felt her pulling her toy out of him then, his asshole feeling strangely empty. As his body got used to being empty again, he suddenly felt her finger intruding its way inside of him once more. He grunted in distaste. She was shoving another of the damn suppositories up inside of him again. The stupid little pills that robbed him of having any chance to control the mess that came out of his backside. He wished – as he did every day – that just once she would forget to do it.
“Okay, roll over again.”
Chad rolled over onto his back again and once more grabbed his baby bottle, putting it right back to his lips. He felt her hands between his legs as she grabbed the first of the two diapers under him and pulled it tightly up and over him, adjusting it to where it needed to be. He felt the pressure as she firmly taped the right side of the inner diaper into place then the added pressure all across the front as she closed the other side and pressed that tape closed as well. Her hand dipped back between his legs again and pulled up the outer diaper, adding much more bulk between his legs and around his hips… but at the same time, adding that much more security. The taping was repeated with the second diaper, and suddenly he was done.
“Okay, Sissy. That’s it,” she said. “Nice and easy. You finish your bottle and I’ll be back to check on you in a little while.”
It was nearly the same every day. He laid right where he was and finished his baby bottle. When he felt the urge to pee before it was done, he held it for as long as he could while he kept drinking. But something about adding additional liquids to his system while he had to pee so badly didn’t work and he quickly lost the battle, wetting his freshly replaced diapers. Oh well, he liked them wet anyway. They felt better that way.