The Bet - Chapter 14 (Friday – week 2 Part 3)

Reminder – My new Baby Bobby story is available for anyone who still wants it.


The Bet
by Karen Singer

Chapter 14 (Friday – week 2 Part 3)

“Giiirrrlfriend…” Robin turned her head towards her friends who were all waiting for her as soon as she entered the break-room. She quickly fixed herself a cup of coffee and carried it over to the table. There were no chairs available because there were already too many women sitting there waiting to talk with her. She set her cup on the table and looked for another chair to drag over. “We heard that you and Chad were arguing in the hall a little while ago…” the same woman asked.
Robin blushed. Sorry, I didn’t mean to be so loud. It’s just that he can be so….” She shook her head in frustration.
“I know what you mean,” another of the women replied as Robin finally spotted a chair and started to drag it over. Almost magically several of the women moved to make space for her because they were all so interested in whatever she could tell them.
And tell them she did… everything she could think of that she knew already. Which was a lot, but at the same time, almost nothing!
“Oh my!” one of the women said when she was done. “Wouldn’t it be fun if he did come down here to talk about makeup? Can you just see it?”
There was a lot of laughter from everyone. “Oh dear!” another woman said through her laughter. “I’m going to have that picture in my head all afternoon now. I’ll never get any work done.” There were more squeals of laughter.
But Robin’s laughter was suddenly more muted. Yeah, it was funny, but at the same time she felt for the guy, as frustrating and as contrary as he was. There was something major going on that she still didn’t know about. Yet.

Robin sat at her desk. The project she was working on was on her screen, but she wasn’t seeing it. Her mind was completely occupied by Chad. The guy wanted to discuss makeup… sort of. She understood his reluctance… sort of. After all, he had been wearing it to work all week! Could she use that in any way to learn more about what was going on? She just wasn’t sure. It seemed so unlikely. Little kids liked to play with makeup – well, girls anyway. She thought of him like a little kid playing with it. Playing at it and not really having any idea of what he was doing. She could play makeup with him, she guessed. But to be honest, she wasn’t too keen on the idea, especially in the break room where everyone could see them.
She looked at her purse with all her makeup in it, not really a lot, only what she needed, but it was probably enough, especially for him. He had a purse full of makeup too. At least, that’s what he had said. Now she wondered. If he did, what kind of makeup did he have? He didn’t even know if he had a mirror earlier.
Maybe that was a place to start though. Instead of really playing with the makeup, they could talk and compare. And in the process, maybe she’d be able to find out what was really going on.
It wasn’t much, but at least it was a plan.
She looked at her watch, it had been about an hour now since she had taken her last break. Now was as good a time as any.

Chad was working on his project when he heard Robin call his name behind him. He turned around and glanced at his watch. “Oh Robin, I’m sorry, I’ve been working on my project and I didn’t even start on the animations yet.”
Robin smiled at him. “That’s not why I’m here. Come on, it’s break time. Time for some coffee.”
Chad was surprised. He had almost forgotten. He was fairly sure he hadn’t actually promised he’d go down to the break room with her. “Uh… I’m not sure,” he replied, “I’m still working on this piece.”
“Oh come on Chad, get up out of that chair for a while and live a little. I’m going with you. It won’t hurt you to just get a cup of coffee. And while we’re there, if you still want to talk about makeup, then that’s fine. I don’t mind!”
But Chad still felt too uncomfortable about it. “Robin, I just can’t…”
“Oh come on!” she said. Then to help him along, she reached down and pulled out the drawer where she guessed that he had now stashed his purse. It was there. She grabbed it and handed it to him. “Here! Now come on!”
For the first time, Chad realized that she had her large tote bag with her too. Why was it that when a woman carried a purse you didn’t always notice? He seriously doubted it would be the same for him. “But…”
“Oh for heaven’s sake. Just stand up and walk with me.” It was like talking to a child. But finally he stood. Not wanting him to back down again, she linked her arm through his and walked him out into the hallway. She kept hold of him till they had gone well past the first turn.
If Chad thought he had been scared and embarrassed by the way he was dressed every time he walked down to the break room before, it was nothing compared to how he felt now, carrying his purse. But then he realized that at least this time he wasn’t wearing any makeup. That thought made him feel a bit better – very little, but a bit.
“So you’ve really got a bunch of makeup in there?” Robin asked as they walked.
“Yeah, all of it.”
“All? Then you can’t really have very much.”
“I think it’s a lot. Too much!”
“Chad, no woman ever thinks she has too much makeup.”
“I’m not a woman.”
“Then why are you doing this?”
Robin was hoping for a better answer, and she felt like she almost got one, but instead, he said. “It’s complicated.”
She sighed.

Neither Robin or Chad noticed the woman peeking around the corner of the hallway after they passed. She had sat at the break table earlier and laughed along with Robin over Chad. She followed them quietly. After they were inside, she stayed just where she couldn’t be seen and tried to peek around the doorway to watch them, hoping that neither of them would realize that she was there.

Robin went straight to the coffee pot and poured herself another cup. Chad waited behind her. When it was his turn, he took a cup, then had to figure out how to juggle his purse, the coffee cup, and the coffee pot all at the same time. Not for the first time did he wish for pockets again. He had to hang his purse on his left arm, and hold the cup in that same hand while he poured his coffee with the other hand. He was just glad he drank it black so he wouldn’t have to mess with the creamer or sugar too. He followed Robin to the back corner table where she had sat down. Her tote bag was on the floor. He set his purse down there too.
“Don’t put it down there,” she said, “I want to see what you’ve got.”
Chad hesitated, still not sure about the whole situation. He looked around, there was nobody there to see him. Throwing caution to the wind, he set his purse on the table and opened it.
Robin wanted to peer inside, but she controlled herself.
“You really want to see all this stuff?” he asked.
“Of course,” she replied.
Shaking his head and wondering why on earth he was really doing it, he began dragging all his makeup items out and setting them on the table.
Robin was a bit surprised to see quite so much. Picking up a powder compact, she opened it. “See, you do have a mirror,” she said, showing it to him.
“Not like yours.”
“Are you ready to carry something as big as this?” she asked, indicating her tote bag.
He almost laughed. “Not yet.”
“I’m surprised you bought so much since you’re just starting,” she said.
“Well, it wasn’t exactly my idea.”
“Your makeup lady?”
He nodded. “Yeah.”
“Does your makeup lady have a name? I mean, it might be easier than just calling her your makeup lady all the time.”
He was a bit reluctant to tell her, but finally he just said, “Mel.”
Robin smiled even though she literally had to drag every little bit out of him, but at least she had a name now. It was better than nothing.
“So what has Mel taught you?”
“Not much,” he admitted. “Really, she’s just concentrated on my eyes and then this morning she started with the foundation.”
“It was pretty bad this morning.”
“Yeah, I know. But it was the first time she’d really shown me anything about it.”
“What did she show you?”
Chad picked up one of the liquid foundation jars and started telling her about what Mel had him doing. Robin asked a few questions, and soon Chad found himself showing her other things. It wasn’t till his coffee was half gone that he realized he had been sitting there totally engaged in girl-talk with her. The very thought of what he had been doing quickly stimulated his overly repressed system, sending pinpricks of pain right where he didn’t want them. The pain reinforced his thoughts about talking about makeup like a girl, which quickly made the pain even worse. He winced against the pain, but it was too late, Robin had noticed.
“Is anything wrong?” she asked quickly.
“No!” Chad replied a bit too forcefully. But he couldn’t continue talking about makeup anymore. It was too painful. As quickly as he could, he started packing everything back into his purse again.
“What’s wrong?” she asked again.
“Nothing!” he replied. “Come on. I’ve got to get out of here.”
Robin had to hurry to catch up with him. She still didn’t know what had gone wrong. For once he was beginning to relax and open up to her, and then all of a sudden he had closed down… again! And the only thing she really had now was a name – Mel. Completely useless information!

The woman who had been watching them hurried back down the hallway before either of them could know that she had been watching them the whole time. She hadn’t been able to hear any of what they said, but she had seen most of it. He had really been there showing her his makeup. Amazing. A funny idea struck her. The more she thought about it, the more she wanted to do it. But it was Friday, her idea would have to wait till Monday.

Shortly before quitting time, Chad looked away from his computer. He really hadn’t been working all that much since he had taken the break with Robin. Had he really shown her all his makeup and been talking about it with her? He couldn’t believe it. But now his thoughts were more and more on Mel and what she might do to him for washing all his makeup off. Would it be better if he reapplied it before he went home? He decided, it was his only hope. Nobody was around. He pulled his purse back out of his desk drawer. Robin had shown him the tiny mirror in the compact. He found it and opened it. It was so small. He could hardly see any of his face at all. Carefully, he put some of the liquid foundation on his finger and began dabbing it in spots around his face. He began spreading it out, trying desperately to see it properly in the tiny mirror in his hand.
“You know, that works better if you use a brush.”
Chad turned in horror to see Robin standing at the entrance to his cubicle watching him.
“I don’t have a brush,” he admitted.
“Well, you can use your fingers like you’re doing, but if I were you, I’d get a brush. A good one.”
“Thanks,” he said as he went back to work. He was glad to realize that Robin had left him again. But she was back all too quickly.
“Here,” she said walking back into his cubicle and brandishing a small brush in her hand. “Let me help you.”
Chad was shocked and surprised, but before he could really protest, she had planted herself against his desk and was starting to run the soft brush over his face. Not knowing what else to do, he let her work on him. “There,” she finally said. Do you want me to add some powder or blush too?”
“No thanks,” he replied, wondering how the job she had done looked.
“You’re sure?”
“Yeah, thanks.” He grabbed his tiny mirror and tried to see what she had done.
Robin left again and came back a moment later with her larger mirror. “Here,” she said, “use this.”
He grabbed her mirror gratefully. Yeah, she had done an amazing job. He promised himself he would get some brushes to work with real quick.

“Are you going to do your eyes too?” she asked.
He was planning on it, but he wasn’t sure he wanted to do it with her watching. “I was thinking about it,” he finally said.
“Let me watch,” she said softly. “Maybe I can offer some advice.”
He looked at her for a moment then began sorting through the makeup in his purse.
She watched him doing his eye makeup, very, very slowly, but surely. Not really too bad at all. But then he had been wearing it all week now.
“You did very well,” she told him when he was finally all done. I’m sure that Mel would be proud.
He could only hope. Mel was his next big obstacle to face. His cell phone buzzed and he quickly pulled it out of the pocket of his purse. A text message from Mel. He read it quickly, then put it away again. He let out a big sigh. Her instructions were just what he had expected – go home and change his diapers, no pantyhose, and wear the open toed sandals, pad the cups of his girdle, and a big emphasis on not being late!
“Your makeup lady… Mel?” Robin asked.
He was shocked that she should ask. “Yeah,” he replied softly.

Mel hurried quickly up the steps towards Chad’s apartment, praying that he was ready. She was the one who was running behind and having to stop to pick him up took extra time. She fished the keys out of her purse while she was still going up the steps and had the door unlocked almost instantly. The first thing she saw when she opened the door was the surprised look on Chad’s face. “Are you ready?” she asked quickly without even closing the door.
Chad didn’t know if he should curtsey and greet her properly or answer her question first. He opted for the curtsey. “Hello, Mistress.”
She smiled broadly at him. “Hello, Sissy. Now are you ready?”
“Yes, Mistress,” he said being careful to remember to curtsey.
“Good! Come along, I’m running late.” But Chad’s curtseys had reminded her of something else that she had planned for the evening. “Damn,” she swore softly. She had to really hurry now. Chad was standing next to her, his purse in his hand, his pink diaper bag slung over his other shoulder. “Sissy, before we go, we need to practice something.”
Chad looked at her questioningly.
“Now show me how you’re going to say thank you to me all evening.”
Chad was suddenly shocked. All evening? Was she talking about doing this in public? Warily, he dropped another curtsey with his hands full and said, “Thank you, Mistress.”
“Good, and now show me how you say yes or no to me.”
He curtseyed again, saying “Yes, Mistress.”
“Good enough,” she said quickly as she headed out through the door. “Now come on, I don’t want to be late.” She closed and locked his apartment door behind them and hurried to catch up to him on the steps. As soon as she had pulled her car out of the parking space she said, “I expect to see you curtseying properly to me, all night… everywhere we go!”
Chad already had horrible visions of doing just that running through his head. His stupid chastity device was suddenly causing him pain again. But he obediently said, “Yes, Mistress.” He was going out in public again. He was wearing women’s heels, women’s pants, makeup on his face, the bra cups of his girdle each held a pair of pantyhose to pad them way out… and he was carrying a purse. He mentally screamed. And then he remembered again that they were heading straight to have their nails done! Aaaarrrrggghhh! It was becoming too much. The devilish little teeth of his chastity device felt like they were burning his skin. But fortunately, that’s all they did. He felt so stupid. He felt so embarrassed. He felt so incredibly excited! And at the same time, his need felt so denied.
It wasn’t till a few moments later when Mel made another comment. “You redid your makeup.”
Chad was suddenly very worried. “I’m sorry, I had to. I wore it all morning, but then after lunch…”
“What happened?” Mel asked.
“Well, Cassie…”
“I know very well what Cassie did. Did you cry?”
He was embarrassed to say it. “Yeah, a little. But it hurt!”
“So?”
“So, afterwards… I guess I rubbed my eyes, and I didn’t know it but it got all over my face.”
“You shouldn’t rub your eyes… wait a minute, you said you didn’t know it had gotten all over your face?”
“Yeah, Robin told me.”
“Robin?”
“She works with me.”
“Oh.” Mel digested that. One of his coworkers. “What did she say?”
“She made me wash it off.”
“She made you?”
“I tried to resist, but she threatened to drag me into the ladies room and do it herself if I didn’t.”
Mel almost laughed. She could just picture it. “So you decided to wash it off.”
“I’m sorry. But she wasn’t giving me much of a choice.”
“And then you decided to put the makeup back on again.” She turned her head towards him as she drove. “Good girl!”
Chad felt really good at her compliment. “Thank you, Mistress.”
Mel smiled broadly. “I noticed you did a really good job with the foundation this time.”
“Actually, that was Robin’s doing. She kind of helped me.”
Mel turned her head and looked quickly back at him. Suddenly she wasn’t so sure about things. She didn’t know why, but she suddenly didn’t like Robin. Not that Robin had done anything at all wrong. Was Robin pretty? Did Chad love her? Was she another reason that Chad was getting divorced? She knew she shouldn’t feel jealous, but she did. It was a woman thing she knew. She had unknowingly staked out her territory on Chad as part of this bet and she didn’t like any other women messing with her property. She brooded about that all the way to the nail salon.

“Hello, Sissy,” the little Asian woman who had done his nails last week said as he walked in.
“Hi,” he replied.
“Sissy!” Mel’s voice suddenly sounded like a gun being fired at his head.
He hated doing it, more than he realized he would, but he had no choice. “He dropped a quick curtsey and said, “Hello.”
The stare and look of astonishment on the nail technician’s face was almost priceless. It took her a moment to fully recover. “Ok, Sissy. Let’s get started.”
Mel smiled as she watched Chad walking away. His embarrassing evening was only just beginning. She was determined to make it even worse now after hearing about Robin.
“You cut you fingernails!” the little Asian woman complained after his toes were done and they had sat down to start on his hands. “And you did a bad job. You should have let me do it.” Chad said nothing as she tried to smooth the edges where he had left them a bit jagged. A little while later, Chad was looking at his almost electric pink fingernails. They didn’t look nearly as feminine as they had last week, not because of the color, but because they were so short. But he was very embarrassed by them never the less.
“Let me see,” Mel called again from the table where she was having her nails done.
As he had done last week, he walked over and held his hands out so she could see.
Mel gasped and pulled her hands away from the woman who had been working on them. “Sissy, you cut your nails!”
Chad knew she would be angry, but he was still glad he had done it. “I had to,” he explained, “they were getting in the way when I typed.”
Mel looked at him angrily in the face. “It won’t be happening again! Now thank the lady who worked on you properly, and make sure you leave her a good tip again.”
Chad figured he’d probably get punished a bit later for cutting his nails, but he still didn’t care. It was like a tiny way that he had found to deny her. He almost laughed to himself as he dropped another curtsey to the nail technician and said “Thank you for doing my nails.” He heard laughter from a few women who were sitting by the door waiting their turn. He didn’t care. After he had paid his bill and left her a tip, he sat in one of the few vacant chairs, proud of himself, not caring in the least about the other women watching him all too closely. The way things had been going lately, even minor victories seemed like major ones, and they needed to be savored.