The Bet - Chapter 13 (Thursday – week 2 Part 3)

The Bet
by Karen Singer

Chapter 13 (Thursday – week 2 Part 3)

Just before lunch, Robin stopped at Chad’s desk. “I’m going out for a burger, want to come?”
“No thanks, I can’t,” he replied.
“Why not? Got another heavy date?” Chad thought for a minute. “Something like that.”
“You’ve got a lunch date? Good for you.”
“No, not really.”
“But you just said you had one.”
“No… well yes I did, but… It’s complicated.”
“So explain it to me.”
Chad sighed. “No. I don’t want to talk about it.”
“Ok,” Robin replied. “See you later.” She had tried and he had clammed up again. But now she was really curious. She went down to her car and waited.
She had to wait about five minutes before Chad finally came hurrying out of the building and then got into his car. As she saw him walking, she noticed that he was walking a bit more awkwardly than he had been this morning. A little bit straddle legged maybe? Probably not, she decided.
When his car pulled out of the parking lot, she followed. Again, he drove directly to the gym and she pulled into the driveway past it. As before, he got out of the car carrying not only his purse, but the big pink bag as well. Robin drove off to get some lunch. Obviously, Chad was going to the gym almost every day. One thing was for sure, she admired his determination. Exercising everyday was not her idea of fun.

“Hi Sissy,” the receptionist said teasingly, and all too loudly.
“Uh, Hi,” Chad replied, embarrassed that she had called him Sissy. “Is…”
“I’m going. Just be patient.”
Chad waited while the receptionist went back to find Cassie. He was glad that this time she and Cassie came back a lot faster.
Cassie stopped about ten feet from where Chad was standing. “Hi Sissy,” she said. Again Chad felt embarrassed by the name. He started to walk towards her, but she held up her hand, stopping him. “Aren’t you going to say hi to me?” she asked, as if she were hurt.
“Uh… Hi Cassie,” he replied.
“Oh come on! You can do better than that! I want you to do it like you did last night.”
Chad looked around. He couldn’t curtsey to her here. “Cassie please… not here!”
“I’ll tell Mel.”
Chad suddenly wanted to scream. He had no doubt that Mel would be mad at him if he didn’t do as Cassie said. Since he had his purse in one hand and was holding on to his diaper bag in the other hand, he just dipped down in a quick curtsey as he said, “Hi Cassie,” one more time.
The receptionist went into fits of laughter and Chad’s embarrassment skyrocketed. “Much better,” Cassie said as she turned and led him through the room full of exercising women.
As soon as Chad got back to the now familiar room and Cassie had closed the blinds on the door, he began to get undressed. Cassie watched him closely as he did it. As soon as he had gotten his girdle pulled half-way down however, Cassie immediately noticed a bit of a smell that hadn’t been there before. “Are you finally messy?” she asked as he pulled the girdle off completely.
“Very,” he replied. “Since I left for work this morning.”
Cassie just nodded and waited till he had removed his plastic panties too. Then she told him to lay down on the floor as usual. She opened his diaper bag and gave him his bottle to start on first. Then she began unpeeling his diapers. “Pew! Wow, you’re a real mess!”
“It’s the girdle,” Chad replied pulling the nipple out of his mouth. “It makes it hard to go and then the mess just slides around wherever it can.”
“I can see that,” Cassie said as she pulled out the box of baby wipes and another plastic bag from his diaper bag to put them in. It took a few minutes and plenty of wipes, but eventually, she had him completely clean. Chad wasn’t quite finished with his bottle yet. She looked closely at his cock restraint, and especially at his flaccid penis inside it. She could see some red marks up around where the little teeth had dug into him. Has somebody been naughty and been trying to get hard?” she asked. He didn’t answer. She didn’t expect him to.
With an evil grin on her face, she grabbed his cock restraint lightly and gently rocked it back and forth, trying to get a response. But the only response to that motion was the sudden look of worry on Chad’s face. She pulled on it and saw Chad’s face register a little bit of pain. She suddenly felt frustrated. How was she going to try to stimulate him if she couldn’t touch or even pull on the damn thing?
She reached under and cupped his exposed balls, massaging him gently. The look of worry on Chad’s face suddenly increased. “Please don’t,” he suddenly said. The worry in his voice was very evident.
“Just drink your bottle like a good baby,” she replied as she kept working on him. But it was plain that he was trying desperately to control himself. She could see the little teeth inside the device digging in deeper now as his cock had grown a tiny bit, but mostly it was still staying soft inside the thing.
“Please,” Chad begged again.
“Let me guess,” she said. “I’m betting you want this really bad. Don’t you?”
“Yes!” he replied. “But I can’t. It hurts! It hurts a lot!”
Wickedly, Cassie kept at it. The look of pain was now evident on Chad’s face. He couldn’t drink his bottle anymore and wasn’t even trying. Despite the teeth digging in to him, his cock inside the device was growing, filling the inside of the restraint more and more. Then almost completely. Chad was now thrashing around under her and she was having more and more trouble keeping at it.
Chad couldn’t take the pain anymore. He roughly pushed Cassie’s hands away and curled up on his side, both hands wrapped protectively around his plastic covered privates.
Cassie backed off. “You seem to have a long way to go in learning to control yourself. But I guess you’ve just started so I can’t expect much more than that.”
Chad didn’t say anything, he just rocked himself on the floor till the pain subsided enough. Cassie helped him roll onto his back again. She slid two fresh diapers under him and coated him wherever she could with the baby lotion. Then she taped him up again. A few minutes later he was completely dressed again.
“Feeling better now?” Cassie asked.
He nodded. “Yeah, the pain has gone down a lot.”
“You know, Mel asked me to do that.”
Chad groaned but didn’t say anything.
Cassie led him out to the front, but before he could get out the door, she stopped him. “Chad! Aren’t you going to thank me?”
Chad turned around aghast. He wanted to run out of there. The receptionist was watching all too closely again, anticipating it. He quickly curtseyed and said “Thank you, Cassie.” Then he all but ran for his car as he heard the peals of laughter from both the receptionist and Cassie behind him.

Robin was standing just inside the door of the building after lunch, talking with a couple of other women. Out of the corner of her eye, she noticed Chad hurrying back from his lunch. As he came through the door, she watched him closely. No, it had just been her imagination. There was nothing wrong with his walk at all. The other women with her were staring at him too, watching him hurrying back to his desk. “And you said he went to the gym again?” one of them asked.
“Yeah. Just like yesterday.”
“What I wouldn’t give to see what goes on in there. I wonder what kind of exercise routines they’ve got him on?” another woman remarked.
Robin was wondering exactly the same thing.

Chad felt a lot better after lunch, mostly because he was wearing clean diapers. That feeling alone was like heaven. He had even thrown caution to the wind and ordered an extra large size fries with his burger before coming back to work, because he was hungry. He realized that the baby cereal he had eaten for breakfast hadn’t really filled him up as much as he would have liked. Unfortunately, the extra large fries also came with an extra large drink. He hadn’t finished all of it, but it had just been such a pleasure to drink out of something besides a baby bottle for a change. As he predicted though, because of the extra drink, he was peeing more than he would have liked. But there was nothing he could do about that now.
He was getting down near the end of the project he was working on and he could clearly see the overall end results now. He felt a lot of pride in his work, especially this time. He knew the clients would love what he had done. As he was working intently, he suddenly realized that he was peeing. He stopped working completely and just sat there, trying to remember if he had known beforehand that he was going to pee. He had been working hard, not concentrating on peeing or having to pee. His mind had been completely busy elsewhere. Did he know he was going to pee and just put it out of his mind? He wasn’t sure, he couldn’t remember. He went back to work, but started watching himself. It had been another strange experience for him today.
Robin stopped by a little while later to ask if he wanted to go down to the break room with her. He didn’t even have to think of reasons not to go. “Not now,” he replied, still mostly intent on his work. “I’m getting close to finishing this thing and I’d really like to keep at it.” Then he ignored her again. But Robin didn’t leave. “Chad, I know you want to finish that, I understand, but do you think that later you can take a few minutes and look through this next project with me? I’ve come to a complete standstill on what I’m working on now.”
Chad didn’t really want to look up from what he was doing, but he understood her problem. “Yeah, maybe later, ok? I’m going really well on this thing right now and I’d like to keep at it.”
Robin seemed much happier. “Ok. Thanks Chad,” she said as she headed to the break room to talk with her friends.

Mel’s text message came in earlier than usual. She wanted him to head directly to her office after work instead of going home. He guessed the reason was because of the therapy session they were scheduled for later. He was looking forward to it. Unfortunately, it probably also meant that Mel would take him out to dinner somewhere beforehand. He prayed that for once she wouldn’t make him drink from another baby bottle while they were out. That was so embarrassing! But then with Mel, what wasn’t?

It was late in the afternoon when Robin stopped by Chad’s cubicle again. “Chad, can you please spare a few minutes to go through this thing with me? It’s getting late.”
Chad stopped working and looked at his watch. It was getting late. He had gotten a lot done though. He looked up at Robin. “Yeah, I guess. Let’s see what’s in the folder.”
Robin realized that he hadn’t even looked over the new material yet. “Chad, there’s a lot of stuff here and a lot of screen shots to look through. We need to lay it all out where we can see it better. Let’s take it down to the break room where we can use one of the tables.”
That was something that Chad really didn’t want to do. “Can’t we just spread it out here?”
“Chad, look at your desk. It’s a mess! And mine is pretty much the same. Besides, it’s still not enough room.”
Chad picked up his folder and flipped through it. “Shit!” he exclaimed softly. “There’s a ton of diagrams in here.”
“I know, I looked already. That’s why I suggested the break room.”
Chad nodded. It would be the only practical way. But he was still concerned. “You don’t think there will be too many people there right now, do you?”
“Chad, really! You’re the one who’s been coming to work dressed that way. If you can come in here like that, then I don’t see why you should have a problem going down there either.”
“Yeah, but here I’m hidden. Not many people stop by here.”
“Is that why you’re doing this? Just because you want to and you don’t think anybody is going to bother you down here?”
“No, that’s not why I’m doing it.”
“Then why?”
Chad shook his head. “You just don’t give up, do you?”
Robin smiled. “No… I don’t! So, what’s really going on?”
“Like I said, don’t ask!”
Robin was frustrated again. But they still had the project to look over. “Look Chad, we still have to go through this stuff.”
“Yeah, yeah,” Chad replied, clearly trying to put off what he was reluctant to do. But Robin was right, they needed room to spread the stuff out. “Ok,” he finally said as he got to his feet. “But I don’t know what I’m going to do if there’s anybody down there.”
“That’s a dumb question,” she replied, “you’ll stay there and work.”
The trip through the hallways was about like the day before for Chad, except that this time Robin walked next to him instead of holding his arm all the way. She also seemed more intent on talking to him as they walked. “So how come you’re wearing those shoes?” she asked. “I would think someone like you would have gone for higher heels instead.”
Chad groaned. “Someone like me?”
“You know, one of those guys who likes to wear women’s clothes.”
Chad looked for a way around her question. “So you’re automatically lumping me in that category?”
“Well yeah. What else am I supposed to think?”
This was getting harder by the second. “I don’t know… It’s complicated.”
“So explain it to me.”
“No.”
“So you don’t like to wear women’s clothes, but you’re wearing them anyway. Chad, you have to know that doesn’t make any sense!”
Chad sighed. She just wouldn’t leave it alone. “Like I keep telling you, it’s complicated!”
But Robin kept at him. “So you do like to wear women’s clothes.”
“Yes… I mean no… not…” he stopped. Trying to figure a way to keep her from asking any more questions.
“Ok,” she said. “Let’s leave it at that. You do like wearing them.”
Chad wanted to scream. But by that time, they had arrived at the break room. Chad was elated to see nobody there. They chose a table at the far end of the room and spread their materials out. While Chad was busy looking at the various diagrams and screen shots, Robin got herself a cup of coffee.
“Look at this,” Chad said as soon as she came back with the hot cup in her hand, “Their old site looks really pitiful. This stuff is way out of date.”
“I know. I went to it on my computer. There’s a bunch of links that don’t even work.”
Chad saw her taking a sip of her coffee. “That looks good,” he said.
“So get some.”
But Chad was already a lot wetter than he really wanted to be. Anymore and he would be worried about it starting to show despite the girdle he was wearing. Besides, he figured that later, Mel would be pouring drinks down him again and the last thing he needed was coffee. But it did look good. “No thanks,” he replied, turning his attention back to their work.
But a few moments later, his attention was again brought back to Robins drink. “Chad, get yourself a cup if you want it.”
“No. Not today.”
Robin rolled her eyes. “Oh for heaven’s sake.” She set her cup down on the table and walked over to the coffee pot and poured him a cup. Then she brought it back and handed it to him. “Here! Now stop being contrary!”
“I’m not being contrary.”
“Then why wouldn’t you get a drink when you obviously want one?”
“Like I said, it’s complicated.”
Robins was suddenly very frustrated. “What the heck does getting a drink of coffee have to do with anything else? I’ve seen you drink coffee before. You had some right here yesterday!”
But Chad’s only reply was, “I told you…”
“I know! It’s complicated!” Robin finished for him. “What the heck can be so complicated about getting a cup of coffee, I’ll never know!”
But Chad had no real answer. He sipped at his coffee since he was now holding it and went back to studying the papers before him.
“So how do you want to divide this stuff up?” Robin asked.
“Why don’t you do the initial layout design, then we’ll take it from there. I’m still trying to finish what I’m on now.”
“Ok, that sounds good.” “You’re better at the artsy stuff than I am anyway,” Chad admitted.
Robin was slightly pleased by his compliment, but it was true. She had been an art major in college first. She started packing papers up in the folders. “Let’s get back so I can get started.”
“Fine with me,” Chad said as he took a bigger gulp of his coffee to finish it. As he did, he felt himself peeing again. And again, he wondered if he had realized it before hand that he was going to pee. This time, he didn’t think so. That was troubling… and a bit interesting.
Robin waited for him by the door while he threw his cup away and grabbed his folder. “So,” she started as they entered the hallway, “we know now that you like to wear women’s clothes.”
Chad inwardly groaned.
“Now we just have cut through all this complicated crap.”