The Bet - Chapter 14 (Friday – week 2 Part 2)

Quick Announcement – Just a quick reminder that tomorrow (Saturday) I’ll tell you about the new story I have for anyone who might be interested.


The Bet
by Karen Singer

Chapter 14 (Friday – week 2 Part 2)

When Robin left work at lunch time, she wasn’t really sure where she wanted to go, so she turned out of the parking lot in the direction she had gone all week now, towards the gym. When she had left, she hadn’t seen Chad come out from work yet. As she passed the gym, she was reminded that Chad had been going in there every day. Her curiosity again got the best of her and she quickly turned again into the driveway just past it. This time, she parked her car in one of the parking places while she waited to see if Chad would show up. While she waited, she debated what it was that she really wanted to do. Did she want to go in and inquire about joining the gym after he got there – really just snooping… or should she wait till tomorrow? Five minutes later, she saw Chad finally drive up and again go in with his pink gym bag. Not really sure she was ready to be snooping that obviously yet, she started her car and left to get something to eat.

“Hi Sissy,” the receptionist said, or almost sang, sassily, as he entered through the gym door.
“Uh, Hi,” Chad replied, not at all happy about her embarrassing attitude toward him.
“You want me to get Cassie for you again… Sissy?”
Yeah, she was being a real pain. “Yes, please,” he replied. There was always something about the way she spoke to him that always made him want to search for some kind of a hole he could crawl into.
She came back with Cassie a few minutes later. Chad started walking toward Cassie as soon as he saw her. “Oh no!” she said directly to him, stopping him in his tracks. “I expect you to greet me politely first!” She stood with her arms crossed, waiting.
Chad felt the total embarrassment of his situation again. Worse, his chastity device began to send sharp needles of pain into him for the first time since he had gotten up out of bed. She wasn’t giving him a choice. He quickly dropped a short curtsey. “Hi, Cassie,” he said. The receptionist went into fits of laughter again. Yeah, there had to be a hole in the floor somewhere around there that he could crawl into. He was sure that everyone could see how red his face probably was even through his thick makeup.
“Oh come on,” Cassie complained. “You can do better than that!”
Chad was aghast. She wanted him to do it again, only better! Where too many people could easily see him! Where was that hole in the floor? Where was the earthquake? Nervously, he curtseyed slower and much more fully so he could get it over with. “Hi, Cassie,” he repeated.
The receptionist was almost doubling up with laughter. He noticed that the noise she was making had attracted the attention of everybody in the big room behind her. Cassie had a very pleased smirk on her face. “Ok. Much better. Let’s go get you changed.”
Chad felt more embarrassment walking through the room full of exercising women than he had ever felt before. Especially since he had realized that most of them had stopped their exercising and were just watching him as he walked through. He regretted more than ever the need to have his diapers changed.
Cassie closed the door behind him and once again closed the blinds on the window. “Ok, Sissy, start getting undressed.”
Chad undressed completely down to his diapers while Cassie found his baby bottle in his diaper bag. As soon as he was laying on the floor she handed it to him. Then she untapped his diapers. “No mess again!”
Chad wondered why she should sound like she was complaining. “Yeah,” he said through the nipple still in his mouth, “but you should have seen the mess I made early this morning.”
Cassie laughed. “I can imagine!” She took a baby-wipe from the container and wiped him clean with it, then she grabbed the baby lotion and squirted a large handful into her hand.
Chad saw Cassie squirting the baby lotion into her hand. He suddenly became very worried. The one part of all this that he had once really enjoyed had now become his biggest nightmare. “Do you have to?” he asked, pleadingly.
She smiled wickedly at him. “Yes I do! Now keep drinking your bottle.”
Chad stuck his bottle back in his mouth and sucked on it, but his attention was completely on the feel of her hands as she carefully and sensually spread the baby lotion all over his bottom and whatever front parts that she could. His whole body was tense as she did it, his breathing very shallow. When she finally started working on his exposed ball sac, he stopped breathing altogether and tensed up completely. He groaned between the incredibly stimulating touch of her hands massaging him and the strain of trying desperately to control himself. His need for relief hit him full force. He couldn’t remember ever feeling his need that much. He desperately struggled against so many impossible forces working on him. His breathing was now coming in gasps. And for a while, it was working. But as Cassie continued working on him, it was his need that began to come through more and more. He clenched his fists against it, his hand holding the baby bottle was down near his side, ready to pound the bottle into the floor. Despite his situation, he wanted desperately to feel her hands touching his penis, but that was one place she couldn’t touch.
He felt the tiny pinpricks beginning. “Noooo,” he groaned through his clenched teeth. But Cassie was still working on him and the pain was still growing. Through all the sensations in his body, he opened his eyes and looked at her. She was staring wide eyed at him, but she still had a very determined look on her face. He looked away, he didn’t want to see her face at all. He had to focus on his need and trying to control it. But the pain from the pinpricks was now a deep burning pain. He could feel himself losing the battle more and more. He felt his cock filling the inside of the restraining device. With a loud groan he shoved her hands away again and rolled onto his side. He realized there were tears in his eyes as he cupped his private parts between the baby bottle in one hand and the open palm of his other hand. He rocked himself back and forth, trying in vain to will the pain away. His need was so much! And he was totally denied. His whole world dissolved into his struggle to become soft again so the pain would go away.
Cassie sat on her knees watching him writhing on the floor. She had hurt him again. Purposely. But he had done so much better this time. He was learning already. As she watched him, she realized that she really couldn’t imagine how powerful the need inside him must be. She knew her needs, but she had always heard that men had different, more powerful and urgent ones. She thought she was witnessing just a piece of that right then.
When his writhing seemed to stop, she rolled him over onto his back again. There were real tears still in his eyes. “You did real good today,” she said softly. “Real good.”
“Not good enough,” she thought she heard him mumble.
She reached down and grabbed the wrist of his hand that was still holding his baby bottle and directed the bottle back into his mouth. “Drink up, Baby.” Then she finished diapering him.
Chad finished dressing and she escorted him out after that. He was still recovering, but doing a lot better. She didn’t delay him at the door, she just watched him head out to his car without a glance at anything or anyone around him. She had hurt him. A lot. She felt sorry about it, very sorry. But at the same time, watching him through it all had been one of the most fascinating things she had ever seen. She had hurt him. But he had done good! Somehow, someway, she would find a way to make it up to him.

Robin only ordered a burger and some fries for lunch, but the fast food restaurant was busy and incredibly slow. When she finished, she started driving back to work again. As she passed the gym, she decided to throw all caution to the wind and she turned into the parking lot, fully intent on going in to see if she could spot Chad. But once she was in the parking lot, she realized that his car wasn’t there anymore. What had happened? She hadn’t been gone all that long. Did he decide to cancel his exercising for the day? Feeling disappointed, she headed back to work again.

Mel checked her messages the first chance she got and saw one of them was from Cassie. She called her back quickly. “Hi Cassie. It’s Mel. How did it go today?”
“Hi Mel. It went pretty good. Mel… I hurt him again today… a lot. But I have to tell you that he really did good today. I could see him trying so hard and he really stayed soft for a long time. I really should have stopped but I didn’t, and I’m afraid I put him into some real pain again.
“Don’t worry about it Cassie. You said he lasted a lot longer though?”
“Yeah, like I said, he did real good.”
“That’s great to hear. It means he’s learning. Listen, Cassie, we dare not stop yet. This is probably the most critical time in the game. If we back off at all right now it will take twice as long to achieve what we need.”
“I understand. I’ll keep at it. I just wanted to let you know that he did better.”
“That’s good.”
“Oh, and you said you wanted me to check to make sure he was still wearing his makeup? He was. Like you said, his foundation was a bit on the awful side.”
“Good, Cassie. Maybe tomorrow he’ll have some incentive to do better.”
“Yeah, it certainly can’t get much worse. You know, as much as I hate hurting him, I’m still really enjoying it too.”
“Yeah, I know what you mean, you have no idea what it’s doing to me. I mean the power, sometimes it stimulates me to the point where… Oh God, I’m sorry, I shouldn’t have said that!”
“Why? We’re both big girls now. Sandy and I both figured you were getting your jollies from him… you know?”
“Well, once maybe… I mean definitely. But lately… well, you know, it’s that time and...”
“Mel! What’s wrong with you?”
“What’s wrong? Well, it’s not right… I mean, the mess and all.”
“Geez Mel, it’s like I always say, if you’re not making a mess, then you’re not having sex!”

Robin flipped back and forth from one screen to the next, trying to make up her mind as to which layout she liked the best. They were all good. She really needed a second opinion before she could go any further. She got up from her desk and walked around to Chad’s cubicle. He was working intently. “Chad?”
He paused in his work and turned his head. “Yeah?”
But Robin immediately lost all thoughts about the project she was working on. “Chad! My God! What happened to you?”
Chad was surprised. “Happened to me? What’s wrong?”
Robin was clearly surprised. “What’s wrong? Your face! I thought you were going to wash your makeup off.”
Chad sighed and turned back towards his computer. “Well, I wanted to,” he mumbled.
“Then why didn’t you?”
“I can’t.”
“Why not?”
“Don’t ask.”
“Chad, look at me!” He finally turned back around. “Not only is your foundation all smeared, but now your eye makeup is all over your face. Did you rub your eyes or something? Because it’s really a mess.”
Chad was surprised. He had rubbed his eyes to get the tears out of them earlier. Unfortunately, he didn’t think about his eye makeup running. But what could he do? Mel had said he couldn’t wash it off, and he would be seeing her right after work. She would see immediately if it was gone. He didn’t know what to do. He didn’t know what to say to Robin. “I… I… I guess I must have rubbed them during lunch.”
“Well listen then, if you’re going to wear makeup, then you have to learn to keep your hands off of your face! Dummy! Now come on, go wash it off right away.”
He turned around again. “I can’t.”
“Why not?”
“Because I can’t! That’s all.”
“Don’t give me that. You can’t go around looking like that. Have you even seen how you look? No, of course not. Do you have a mirror in your purse?”
Chad turned back around. “A mirror?”
“Yeah. One of those little things to look at yourself with. You know, a mirror?”
Chad had to think for a second. “I don’t know. I don’t think so.”
“You don’t even know if you have a mirror in your purse?” She threw her hands up in exasperation. “I’ll be right back.” She hurried to her own desk and dug her mirror out of her own bag and brought it back to him. “Here,” she said holding it out to him. “Look at yourself.”
Chad grabbed her surprisingly large mirror and looked at his face. He had black smudges all down his cheeks and out to the sides of his eyes. It looked like his eye makeup was everywhere but on his eyes. He looked awful, and it was all too noticeable. But what could he do about it. He rubbed at a few places with his fingers while he looked in the mirror, very little came off.
“Oh for God’s sake!” Robin exclaimed grabbing the mirror from him. She threw it on his desk and grabbed his arm and pulled him out of his chair. “Now go wash it all off! Now!”
“But I can’t,” he protested as she began pulling him out into the hallway.
“Don’t give me that. Yes you can. You have to!”
“Please, I’m not supposed to wash it off,” he told her.
She stopped where she was for a moment. “What do you mean you’re not supposed to?”
Chad looked down at the floor. “I can’t tell you that. It’s complicated.”
But his answer made Robin even angrier. “It’s complicated, it’s complicated! Everything is complicated! It’s not complicated!” She pulled on his arm again, pulling him towards the rest rooms further down the hall. He went, but not willingly. “Just wash it off. That’s not complicated!”
Chad stopped at the entrance to the men’s room. Was there anyone in there? He hoped not. Mel had told him to not wash the makeup off. He knew he would get punished if he did. And that was something he really didn’t want. He couldn’t wash it off. He turned to Robin again. “I can’t.”
“Yes you can! Now you either go in there and wash it off right now or…” she paused trying to think what to say. “Or I’ll take you into the ladies room with me and wash it off myself!”
Chad was shocked. She wouldn’t!
She saw the shocked look on his face. “Maybe that’s where you belong anyway,” Robin continued, “seeing as how you’re dressing now.” She pulled slightly on his arm in the direction of the ladies room a few feet away.
Chad pulled back. “No… I’ll take care of it.” She wasn’t giving him any choice in the matter at all. As he went into the men’s room he prayed that it would be empty. He also prayed that Mel wouldn’t punish him too much for what he was about to do.
He was lucky, there was no one there. He wet his face at the sink, the water actually felt good against his skin. He had to scrub and scrub at his face with a paper towel to get everything all off, but finally his face was completely clean again. It felt good to him. Really good. He spent a moment looking at his reflection in the mirror, enjoying the sight of his face without makeup again.
As he turned to leave, he glanced quickly at all the toilet stalls and then the urinals lined up against the wall. He wished desperately that he could use any of them. As he looked at them, he suddenly felt himself peeing into his diapers again. So frustrating.
Robin was waiting for him just outside the men’s room. She smiled when he walked out. “That’s much better. Don’t you feel better?”
“Yeah,” he agreed. “A lot… sort of.”
“What do you mean sort of?”
“Never mind,” he said as they walked back toward their desks, his mind more on what Mel might do to him later.
“Geez! You’re the most frustrating person I know lately!”
Chad headed back to his desk, but Robin stopped him. “Oh no you’re not! I need your help now.”
“What?”
“That’s what I came to see you for in the first place. I need you to look at what I’ve got.”
“Oh, ok,” he said as he turned back toward her cubicle instead of his.
He leaned over her shoulder as she sat in her chair and brought up her first idea. “Wow,” he said quietly. “That’s great!” She flipped to her second idea. “Gee, another really good one.” She opened her third idea. “Wow,” he said again. All these are all incredible. I love them all.”
“Yeah,” she replied, “so do I. That’s why I was having such a hard time deciding what to work with the most.”
“Go back to the first one.” She flipped the screen. He stared at it for a moment, “Now the second.” She turned to that one. He stared at that one too, then let out a small laugh. “Wouldn’t it be interesting if we took your header and completely animated it?”
“Animated it?”
“Yeah, instead of just doing the normal stuff, we could have little cartoons that pop up and move around whenever you hover over anything.
Robin laughed. “Chad, that’s brilliant. But I don’t have a clue as to how to do that stuff. That’s your department.”
“Yeah, well I can’t design layouts that look like this either.”
They looked at each other, each appreciating the others compliment. But as they stared for a moment at each other, Chad again looked closely at her face. What did she do about foundation? How did she do her eyes? She only used eyeliner on her upper eyes, like Mel. He tore his gaze away before she could notice that he was staring.
But Robin noticed. “What?” she asked suddenly. “Is something wrong?”
“No, no! Nothing at all. Let’s work with your second idea. I’ll send you some of the animation ideas I have in mind in a little while.”
“Ok,” she said, still wondering if he had been staring at her.
He retreated back to his own cubicle quickly and sat down. Her mirror was still on his desk. He picked it up. It was fairly big, bigger than any of the mirrors he remembered other women carrying. It would certainly take up a lot of space in his purse. But then she always carried that big tote bag. He looked at his face in the mirror. Clean! Nice! How had she done her eyes? It was hard to remember because he had looked so quickly. Where had she started and ended her eyeliner? He couldn’t remember. He stared into the mirror still. Mel had told him to start just in from the corner…
Robin sat in her chair staring after Chad, still wondering if he had been staring at her. She needed to check her face again. She opened her tote bag, and immediately remembered that she had left her mirror on his desk. The urge to check her face grew stronger as she got up to retrieve her mirror. And then it hit her. She wasn’t sure, but it just made sense! She walked around to his cubicle and stopped in the doorway. He was looking at himself in the mirror. “You’re wondering about my makeup,” she said.
Chad turned quickly at her question. He could feel his face turning a bit red. “No, not really… well… yeah, just a little.” He could feel his face turning very red now. He was so embarrassed. “I didn’t mean to stare or make you feel uncomfortable. I’m sorry. I won’t do it again.”
“Chad, don’t you think other women check each other out all the time… in fact constantly?”
“Well, I guess I figured…”
“Geez!” she said as she came further into the room. “It’s only natural Chad. If you’re going to wear makeup, then obviously you’re going to be interested in the way everyone else does it. Don’t you look at the models in the magazines?” “No.”
Robin was surprised. “Well, you should. Women talk about makeup all the time. It’s only natural.”
“Yeah, but I’m not a woman.”
“No. Maybe not. But you’re dressing more and more like one and you’re wearing makeup like a woman. So you have to be interested in what other women are doing.”
“I guess,” he answered, turning his chair around away from her. This whole situation was so embarrassing. Why did he ever enter into this bet? It was so stupid! But he realized that underneath, he was interested. Very interested. And being a male, discussing makeup was something that was always considered taboo. Not to mention what any other women might think if he suddenly wanted to talk about it.
Robin walked up behind him and put her hand comfortingly on his shoulder… and stopped dead, completely surprised. She moved her fingers quickly around his shoulder. “Chad! You’re wearing a bra!”
Chad realized what she had just done and quickly shook her hand off. “No I’m not!”
“But I felt it. You’re wearing a bra.”
“I am not! It’s not a bra.”
“Then what is it?”
“I’m not wearing a bra!” Robin quickly reached out and pressed her hands against his chest before he could stop her. Chad tried to block her hands but was a fraction of a second too late. “Chad, it’s there! I felt it! You can’t deny it!”
“I’m not wearing a bra!” he said angrily.
“Then what is it?”
Chad turned away from her again.
“Chad admit it!”
“No! I’m not wearing a bra.”
“Then what are you wearing? And don’t tell me nothing, because I felt it.”
Chad didn’t say anything for a moment, then finally answered. “It’s complicated.”
Robin wanted to hit him. She actually raised her hand to do it, but stopped herself. “It’s complicated, it’s complicated. Everything is so damn complicated!”
“Well, it is!”
“Yeah… Sure!” She turned away, frustrated, and started to walk out. But she noticed her mirror laying on his desk and picked it up first. She paused in the doorway and looked down at her mirror. She turned back to him. “Look, later, when you’ve calmed down and gotten your head screwed on right, do you want to talk about makeup?”
He was still turned away from her. “No… yes… No… I don’t know!”
“Why don’t you come down to break with me later. I’m sure the other women wouldn’t mind talking about it too.”
He turned around quickly. “God no! Not that!” He turned away again.
She was about to leave and stopped again. “How about if I take a late break and we go down there together again, just you and I?”
She had to wait a moment for his answer. And when it came, she barely heard it. “Maybe.”
She left him for her own desk and sat back down. She was still learning things about him, but overall, she had really learned very little. She desperately wanted to talk with the other women about him and discuss it, but she had told him she would wait for him and take her break later today. To hell with it! She would take her break with her friends and then another one later with Chad. Tom Robinson never came down anyway to check up on her. He probably wouldn’t even care!