The Bet - Chapter 12 (Wednesday – week 2 Part 3)

The Bet
by Karen Singer

Chapter 12 (Wednesday – week 2 Part 3)

At lunchtime, Chad again hurried out to his car and drove to the gym. The receptionist inside looked him over all too carefully again as he walked in. “Hi Sissy,” she said tauntingly.
“Hi,” he replied. “I’m here to see…”
“I know, I know,” she interrupted. She was still looking him over carefully. “Love your eye makeup,” she said.
Chad blushed. Now he knew why he should have washed it off earlier. “Look, will you please just get Cassie.”
“I’m going,” she said sassily as she sauntered off, slowly.
She came back with Cassie in tow a few minutes later and Cassie again led him back to the office. He didn’t feel quite so embarrassed walking through the room full of exercising women today as he had before, but it was still bad enough.
“Pretty eyes,” Cassie said as soon as she had closed the door behind her.
Chad blushed. “I was going to wash it off, but figured why bother – because of everything else I’m wearing.”
“You’ve got a point,” she replied. “So, you’ve been washing it off every morning?” she asked as Chad started to get undressed.
“Yeah, but it was really only some mascara. Before, you couldn’t really tell that I was wearing anything… different.”
“Well, you can certainly tell a bit more now, although to be honest, I think you’ve got a long way to go… Like your shoes by the way,” she added quickly as she saw him kicking them off. “I’m surprised they’re not heels.”
“They were Mel’s idea,” Chad said. They’re a bit too small for me. He looked up at her then, “They are a lot more comfortable than heels though.”
“Sissy, you don’t have to tell me. I’ve worn out more pairs like that than I can count. Now lay down and let’s get you changed.”
Chad laid down on his back and Cassie knelt over him and began untaping his diapers. He suddenly thought about his chastity device, did Mel tell her about it? He didn’t have to wait long to find out.
“What the hell? What the heck is that?” She reached down and grabbed it lightly. Little spikes of pain suddenly registered in Chad’s brain.
“Mel put that on me last night,” he told her. “Please… don’t pull on it. It hurts! I’m having a very hard time getting used to it.”
Cassie examined it carefully. She pulled on it gently a few times, rocking it back and forth to see it better. His penis was completely encased in the thing. And it seemed to be firmly locked in place. She squeezed as best as she could on the hard plastic. “Can you feel that?” she asked.
“Only you pulling on it,” he replied.
“Nothing else?”
“Just pain.”
She gave up touching it. “So what hurts? I can see that the thing is fairly small, but there is still plenty of room inside. You don’t fill it completely – as small as it looks.”
Chad actually blushed. “There are these spikes that dig into me painfully any time I even think about getting a little bit hard or if I try to pull it off. And they really hurt.”
Cassie bent down and examined it a bit closer. Finally she located the tiny spikes. “You mean those little things hurt so much?”
“Like you wouldn’t believe!” he replied.
Cassie sat up straighter and sighed. “Mel’s taken away all my fun.”
“Mine too.”
She laughed. “Yeah, I guess she has.”
From that point on, Cassie was all business, inserting a new suppository and replacing his wet diapers with fresh ones. Then she realized that she had forgotten his baby bottle. She reached into his bag and grabbed one. “Better drink this before you get dressed, baby.” And don’t be too slow about it.
Chad reluctantly did as he was told. He had been hoping that maybe she would have forgotten the bottle.

A little while later, as soon as Cassie had led Chad back out again, Cassie grabbed her cell phone and dialed Mel’s number, hoping that Mel might not be too busy to pick up. She got lucky.
“Hello,” Mel said into her phone.
“What the heck was that?” Cassie asked immediately.
Mel instantly smiled. She recognized Cassie’s voice and also knew instantly what she was referring to. “That’s his latest phase of training,” she replied.
“God, I couldn’t even touch the thing. And he says it hurts if I pull on it too much.”
“It’s supposed to hurt. That’s to keep him from removing it.”
“Well it looks like it works well enough. Hey, speaking of removing things. Did you know he’s been washing off his mascara in the mornings. He told me. I didn’t even know he had been wearing any.”
“Was he wearing any today?”
“Yeah, full eye makeup. And it didn’t look too bad either.”
Mel was all smiles. “Good. I figured he was probably washing it off. I’m really just surprised that he didn’t remove it today.”
“Hey, you know that that plastic thingy you put on him as taken away all my fun too. I hate to say it, but I was kind of enjoying being really mean to him by teasing him and making him all hard before I wrapped him back up in his diapers again. I know how frustrating that’s supposed to be for a guy. I hope you don’t mind.”
Mel laughed. “Mind? Not at all. In fact, I’d like you to continue if you will. Do whatever you can to stimulate him down there. He’s supposed to be learning not to get hard from it anymore.”
“Not at all?”
“Nothing!”
“God! Why?”
“Because he can’t pee when he gets hard and I need him to be able to pee at the drop of a hat. I don’t want anything to interfere with it.”
“Okay…” Cassie replied, dragging the word out. “So you want me to keep playing with him.”
“Yeah, if you can.”
Cassie sighed. “I’ll try… Oh hey… I almost forgot… Sandy wants you to stop by tonight. She has something she wants you to look at. You know, she’s very jealous of me because I get to play a bit with Sissy and she doesn’t.”
“She’s jealous?”
“Yeah, she grills me about it every night.”
“She sounds a bit like my secretary, Andrea. What’s Sandy got for me to look at?”
“I have no idea. She just phoned me about it this morning and asked me to tell you.”
“Ok, I’ll stop by after work.”

Chad yawned and stretched his arms. He immediately felt a slight need to pee again and let it out. He had gotten a large coffee with his lunch after his diaper change because he had been so tired all morning. The coffee had helped, some, but it had also helped to keep him peeing too. He realized that he didn’t really even care about that part. But now, it was getting on in the afternoon and the affects of the caffeine had defiantly worn off. He was feeling so tired again he could just lay his head down on his desk and fall asleep.
Did he dare go down to the break room and get some coffee? Break time was over for most people, but there were no real rules about going down there anytime. Most people stopped in to grab coffee all day. He stifled another yawn. Did he dare?
He rolled his chair out to the opening of his cubicle and glanced down the hallway, there weren’t many people around just then. Did he dare?
He was just about to roll back to his desk again when Robin walked out of her cubicle. “Oh… Hi,” she said to him, clearly surprised to see him there. “What’cha doin’?”
“Just looking around a bit,” he replied.
“Why?” She saw him blush a bit.
“I was kind of thinking of getting some coffee.”
“And you’re afraid to walk down there because of the way your dressed.”
“Yeah, something like that.”
“So just go! You came to work that way.”
“It’s not that easy…” He yawned again. He just couldn’t help it.
“It looks like you really need that coffee.”
“Will you get some for me?”
She looked at him for a moment before she answered. He had been stubborn and rude to her earlier. “No. You can get it yourself.”
He sighed and rolled his chair back to his desk again. Robin followed behind him into his cubicle. She pulled on his arm. “Come on. I’ll walk down with you. Will that help?”
She really wasn’t giving him much of a choice. And he did need something to keep him going for the rest of the day. Reluctantly, he let her pull him to his feet. He would have stopped at the opening to his cubicle to look around, but she dragged him right out into the hallway and just kept going, keeping a hold on his arm all the way. Chad wasn’t sure if she was helping him, or showing him off.
It was a long walk, through several hallways to the break room. Mostly, the hallways were empty, but there were a few people that they passed. Too many of whom eyed Chad closely with looks of surprise. Chad realized that the ones who seemed to react mostly to him were all women. Maybe the men weren’t really noticing him yet – he hoped.
The hallways had been carpeted, but the break room had a tile floor. As soon as they walked into the room, Chad could clearly hear the sound of Robin’s heels on the floor… and his too. There was only one other man in the break room, pouring himself a cup of coffee. The man at the coffee pot looked up briefly, then looked back down at his coffee again. As soon as it was ready, he grabbed his cup and turned around. But Chad and Robin were closer to him now. Chad saw the man’s eyes lock onto him and stare, all too closely, at every detail of the way he was dressed.
The man looked like he was about to say something, but Robin was walking up to him. “Excuse me,” she said before he had a chance to say anything about Chad, “can we get at the coffee?”
The man stepped aside and Robin walked right up to the coffee pot and picked up a cup from the stack. The man backed away toward the door, sipping at his own coffee, never taking his eyes off of Chad. Finally, he turned and left the room. Chad kept watching the doorway behind him.
“Aren’t you going to get some coffee?” Robin asked as she dumped a little creamer into hers.
Chad turned around and grabbed a cup and poured some coffee into it.
“Creamer?” Robin asked holding it out to him like there was nothing out of the ordinary going on at all.
“No thanks, I like it black,” he replied. He was about to head back to his desk, but Robin sat down at one of the tables instead. What was she doing? He couldn’t stay here. “Don’t you want to go back?” he asked.
“No, I need to get away from it once in a while. Don’t you?”
Reluctantly, he sat down with her and took another sip of his coffee. She was staring at him, not taking her eyes off of him while she sipped slowly at her drink. “What?” he finally asked.
“Nothing,” she replied. “I was just trying to imagine how you would look with a little more makeup. That’s all.”
Chad rolled his eyes. Women!
“So how come just the eyes?” she asked.
Chad’s nerves were suddenly grating. But he answered her anyway. “Because that’s all I know how to do.”
“Oh,” she answered. “I guess that kind of makes sense… in a way.”
Then she was silent again, but she still looking intently at his face. Chad kept sipping slowly at his coffee. “So why the eyes?” she suddenly asked.
“What do you mean?” “I mean, why not lipstick or foundation, or anything else? Why just the eyes?”
Chad’s nerves were starting to grate again. “Because that’s all she showed me how to do!” he answered angrily. Then he realized what he had just said. Had he said too much? Given too much away?
But Robin picked up on it instantly. “She?”
Oh God! Why couldn’t she just leave him alone? “I don’t want to talk about it!” he replied.
Robin knew she had just made a small dent. But it was only a tiny one before he had closed down again. But she wasn’t quite ready to give up yet. She sipped at her coffee for a few more moments, giving him time to settle down again. Then she asked. “So did you ask her to teach you?”
Chad just shook his head. She wasn’t going to leave anything alone! “No… Yes… well, it’s complicated.
“What’s so complicated? Either you asked her to show you how to do your makeup or you didn’t? Which?”
Chad was beside himself and almost angry with her for asking. “No, I didn’t ask her to show me how to put on makeup. It was part of something else we agreed on.”
“What?”
But Chad was really getting frustrated. Too frustrated. “I said I don’t want to talk about it! Ok?”
Robin took the last sip from her coffee and stood up again. “Ok, I get it! I’m just trying to help, that’s all. I was just trying to look out for you a bit. But if you don’t want me to…”
Chad felt even more frustrated. He knew she really meant well, but women… They could be so nosy! “Look,” he replied, “I’m sorry. I didn’t mean to make you mad. But this isn’t exactly easy for me.”
“So what isn’t easy for you?” she asked.
Chad just looked at her, then he turned away and headed for the door by himself, his head hung down and looking at the floor all the way. He threw his empty cup into the trash on the way out.
Robin stood there and stared after him. She had made some progress, finally, but did she know any more than she did before? She wasn’t really sure. All she knew was that she was right, there was something major going on here, a lot more than it looked like on the surface. Knowing the only way she was ever going to learn anymore was to stick to him, she ran after him, and again put her arm through his as they walked together back to their desks.