The Bet - Chapter 19 (Wednesday – week 3 Part 2 of 5)

The Bet
by Karen Singer

Chapter 19 (Wednesday – week 3 Part 2 of 5)

Chad sat down at his desk and noticed that Robin must have turned his computer off last night. He mentally thanked her, the company didn’t like for the computers to be left up and running every night. As soon as he could, he opened up his spreadsheet for tracking his progress on the bet. Forty-four days to go. And eternity! He had done really well holding back yesterday, but he didn’t really know how long he had held it. He put down thirty minutes as a conservative estimate and closed the spreadsheet. Still on track!
“Morning Chad,” Robin called as she walked past his cubicle on the way to hers.
“Morning,” he called back as he started opening the project they were working on. He needed to do a lot more with the animations they had planned on today.
“Hey Chad,” Robin said a few minutes later, from the entrance to his cubicle. He was startled because he hadn’t heard her come back. “What happened to you yesterday?”
He turned around to face her. But before he could say anything, she let out a little squeal. “Chad! Look at you. You’ve had your hair done… and finally… you’re wearing a blouse!”
He could feel himself blushing. “Yeah, well…”
She came all the way into his cubicle so she could see him closer. “Where did you get your hair done?” she asked.
“A friend,” he replied.
“Mel? Your makeup lady?”
“No, someone else.”
“Well, whoever it was did a nice job. I like it.”
“I think it looks too girly,” he replied.
“Well for heaven’s sake! Look at the way your dressed. And you’re worried about it being too girly? Is that how you asked her to cut it?”
“No, she just did it.”
“Well, I like it. And finally… finally… you’re wearing a blouse! Very pretty, by the way. It’s a big improvement.”
“Improvement?”
“Yeah. Seeing how everything else you’re wearing is female. It looked dorky before… stupid!”
“Maybe,” he admitted.
“You know,” she said, “that blouse would look a lot better with some padding in your bra. A lot better! You should do it.”
He rolled his eyes. Now he was sorry he had decided to wear the blouse. “That’s ok,” he replied. I like it just the way it is.”
“But it needs something!” she replied. “It’s tapered for breasts. It doesn’t look right without anything! You need breasts!”
She was pushing at him. Asking him to do something he didn’t want to do. “That’s alright. I like it the way it is!” he replied a bit too forcefully before she could argue anymore.
She backed off and just stared at him for a second. Had he yelled at her? She wasn’t sure. But he certainly hadn’t been very polite! “Suit yourself. I’m only trying to help,” she replied, sounding just as put off by him as she felt. She turned to walk away and stopped. “You know, you could really use some color on your face too. Just eye makeup and foundation makes you look too pale. A little lipstick wouldn’t hurt you.” She left then, not wanting to stay around him any more. In fact, her last comment, while totally practical and the way she really felt, had been said more as a way to strike back at him for his attitude a few moments earlier. She tried to force him out of her head as she got down to work.
Chad stared at his computer screen trying to concentrate on his work, but all he could think about was his last conversation with Robin. He hadn’t meant to be so forceful, it had just happened. But damn, the woman could push. Why couldn’t she leave things alone? She was always after him, peppering him with questions about what was going on, and he didn’t want to tell her. He wasn’t going to tell her! It was none of her business! And now she wanted him to pad his bra? Well, the cups of his girdle anyway. It wasn’t going to happen!
But he still felt bad about the way he had spoken to her and she had been obviously put off. And she had shut his computer down for him last night so he wouldn’t get in trouble. Damn her! Damn all women! Why couldn’t life be simple? And so what if his face looked pale? Mel hadn’t said he had to wear anymore makeup. He didn’t have to please Robin – only Mel!
He sat back and sighed. But Robin was still a friend. One of the only friends he had left – maybe THE only friend. He shouldn’t have gotten so angry with her. But damn, the woman had been pushing at him again. Damn her! He pulled his purse out of his desk drawer and found the little compact with the mirror in it. He looked at his face as best as he could. He needed a peace offering. Some small way to say he was sorry - friend or not, he did have to work with the woman. He selected a lipstick… and then some blush… and then something to fix the tiny smeared spot from breakfast.

“Robin,” he said contritely from the entrance to her cubicle.
“What?” she asked without turning around. She was still put off.
“Is this any better?”
His question startled her, as did the tone of his voice. She turned around and was shocked. She smiled. “Yeah, a lot better.”
“Look, I’m sorry for my attitude a few minutes ago. This isn’t easy for me. And when you push so hard sometimes, I guess I get frustrated. That’s all.”
She looked a bit sheepish. “I know I can be pushy sometimes, but that’s just the way I am.” She suddenly had a questioning look on her face. “If it’s so hard for you, then why do you do it?”
“I can’t tell you that.”
“Why not? Why can’t you just come out and admit that you’re doing it because you like it?” She was sounding angrier again.
He shook his head. “You don’t understand.”
“Then explain it to me!”
“I can’t!”
“Why not?”
“Because… it’s complicated!”
She threw her hands up in the air in exasperation. “Get out of here!”

In the middle of the morning, Mel checked her computer between clients and found an email from Cassie. She was very surprised to see an email since Cassie always called. When she opened it, the email just said that she thought Mel would like to see some pictures of Sissy from last night. There were three pictures enclosed. The first picture was a close-up of his face. It showed him right after Cassie must have finished fixing his hair. She looked closer. His hair looked different in the picture than the way it looked this morning. Much more feminine and really pretty… and not just because of the pink bow tied into it. The difference she decided was that it was fixed the way a woman would fix it. Obviously Cassie had used a curling iron on it.
She opened the second picture and almost laughed. Chad’s hair was totally covered in bows and hairclips of all kinds. She looked closer. She could hardly see any of his hair at all.
She opened the third picture and smiled. Chad playing with the baby toys on the floor. It was actually cute.
She went back to the first picture and stared at it. Cassie really had done a nice job on his hair. She made a mental note to talk about it with her later. Unfortunately, she had another client to meet just then. But she did do one thing quickly before she closed the email. She forwarded it to Chad at work.

Chad opened the email from Mel with a little trepidation. He was surprised to see the email because she had never emailed him before. He was happy to see however that the email didn’t contain any instructions for him, just some pictures. He glanced around to make sure that nobody was walking past his cubicle that could see in – especially Robin. Then he opened the first picture. He stared at himself for a long time. It was the first chance he had to see what Cassie had really done to his hair. It looked far more feminine in the picture than it did when he had seen it in his bathroom mirror this morning. Maybe it was the pink bow. But he really knew that the bow had very little to do with it.
He opened the second picture and let out a small laugh of surprise. His head was completely covered in their hairclips. It really was a funny picture.
He opened the third picture - him playing on the blanket with the baby toys. He was very relieved that more embarrassing pictures weren’t included. These were all “safe.” As far as he could tell from the email, that’s all that Cassie had sent to Mel. He opened up the first picture and stared at it again. Had he really looked like that last night – with the makeup and the big pink bow? Embarrassing! He closed the picture and quickly deleted the email to make sure that nobody at work would ever “accidentally” see the pictures.
“Do you want to come to break with me?” Robin’s voice asked from behind him.
He turned around, horrified to see her standing there. Had she seen any of the pictures? She didn’t act like she had. She was just standing there waiting for an answer. He shook his head. “No thanks,” he replied, praying that she hadn’t really seen anything.
“Ok,” she replied as she walked off.
He breathed a sigh of relief. It looked like it was ok.

Late in the morning, Mel checked her messages and called one of the numbers back. “Hi Gloria, it’s Mel.”
“Hi Mel. I was just wondering how you and Chad are getting along now.”
“Much better. And Gloria, I’ve really got to thank you for getting my head straight yesterday. I guess it was kind of a wakeup call.”
“So things are all honky-dory between you two again?”
“As far as I can tell anyway.”
“Good. So how about your date last night?”
“Ugh! I can’t begin to tell you how awful it was – from start to finish!”
Gloria laughed. “Want to tell me about it during lunch?”
This time Mel laughed. “Sure. And this time, I’m buying.”

Robin watched as Chad hurried out to his car at lunchtime. She knew exactly where he was going, just not exactly what he was doing. It frustrated her a bit, but then there was a lot about him lately that frustrated her. Not wanting to think about it anymore, she purposely drove off in the opposite direction.
While the change in her routine felt refreshing and good, it only served to remind her more that she had been following Chad everyday. As she ordered lunch in a place she hadn’t been to in weeks now, her mind dwelled on him. What was he really doing at that gym? While she ate, she continued to think about it. She couldn’t help it. She knew that she needed to start going to lunch with some of her girlfriends instead! It would be so much better than thinking about Chad while she ate. But then, even during their breaks at work, Chad was a major part of every conversation. There was no getting away from it.
By the time she finished eating, she realized that she was more determined than ever to get to the bottom of what was really going on. Sissy? Was he really calling himself that at the gym? It didn’t seem likely, but by the way the receptionist had reacted, she actually believed it. How about anywhere else? Where else did he go? What else did he do with his life? How could she find out? He was like one big puzzle – and she loved puzzles!

Chad walked into the gym and saw the receptionist immediately put a big smile on her face. Was there a twinkle of mischief in her eyes as well? “Hello Sissy,” she greeted him all too loudly.
He hated his life. He dropped a quick curtsey to her and said a simple “Hello.” The receptionist instantly began giggling. Why? She had seen him do it before. Fortunately, she immediately went in search of Cassie. She and Cassie were back a few moments later.
“Hi, Sissy,” Cassie called as soon as she spotted him. Chad curtseyed to her and returned the greeting. Then he followed her back to their usual office. While he began getting undressed, Cassie pulled one of the baby bottles out of his bag for him. “I like your blouse today,” she said as he was getting undressed.
He wasn’t sure how to answer. “Thanks,” he replied.
“It could use a bit of padding in the breasts though.”
Ugh! Once again he was sorry he had worn it. “I know,” he replied.
She looked up at him as he was pulling his pants off. “Then why didn’t you pad them?”
He shook his head. “I was at work before I found out.”
“You found out at work?”
He blushed. “Yeah, from one of the women I work with.”
“What did she say?”
He shook his head. “I’d rather not talk about it.”
She shrugged her shoulders. “I was just asking. By the way, I’m glad you finally added some color to your face. It looks much better.”
He didn’t want to tell her that it was because of Robin that he had done it. “Thanks,” he replied simply. He suddenly felt the need to pee again. It would be better to do it now than after she had changed him.
She saw him stop undressing for a moment and just stand there. “What’s wrong?”
“I’m wetting myself again. Better now than later.” Cassie laughed.
A few minutest later, Chad was once again sucking on the baby bottle while Cassie was rubbing baby lotion all too intimately into the front of his private areas. She watched him closely. He was staring at her. Even with the bottle in his mouth she could tell there was a worried look on his face. His chastity device prevented her from really touching him where she needed to, but she did her best to excite him anyway. His bottle was half-finished when she finally smiled and pulled her hands away. He had never stopped staring at her. He had never stopped sucking on his bottle. And he had never even begun to get hard. “You’re definitely getting a lot better,” she said. He said nothing, but she thought she saw him blush a bit.
She remembered all too well how he had reacted last night when they had played with her little toy in his asshole. He had done amazingly well then too. Her voice was almost a whisper. “Would you like me to play with your backside a bit again?”
He didn’t know how to answer. Yes he did… but no he didn’t. When she did it, it was the closest thing to a sexual sensation he could feel – other than peeing. But at the same time, it disturbed him way too much. He couldn’t decide.
Her voice was still soft. “You really seemed to like it last night. I don’t have to do it today, I was just wondering.”
She was leaving him a way out. But he had liked it last night. A lot! Without realizing it, he let out a small whimper in his indecision. His need for sexual relief was so much. But the humiliation!
She smiled down at him and took the bottle away from him. “Roll over. I’ll just do it a tiny bit for you, ok?”
He needed it, but he hated it. He despised the fact that it should affect him like it did, but he also wanted it. She put her hand on his hip and pushed. He rolled over and brought his knees under him, lifting his rear end high into the air – totally exposed and open to her touch. Again, he whimpered in his need, and frustration, and humiliation.
Cassie lubed her hands again with the baby lotion and began massaging his backside again. Within moments, she could feel him moving almost rhythmically back and forth under her touch, and she hadn’t even gotten to the good part yet. But when she did start to go there, his movements stopped, completely. She touched him lightly there again and saw the quick shock that seemed to run up his spine. She pulled her finger away, then did it again. No shock this time, just acceptance and waiting. She pushed till her fingertip entered him, then she wiggled it. He arched his back and neck at the sensation. She pulled her finger away again and he almost collapsed back into his original position.

Chad closed his eyes and concentrated on her hands. Once again he felt her place her finger, this time ever so lightly against him. He waited patiently wanting more. Very, very slowly, he felt the pressure increasing, till her finger finally slipped in. Then her finger paused. Would she wiggle it again? But now the pressure was increasing. He could feel her finger going deeper inside of him, then deeper still. He unconsciously let out a small moan. Her finger pulled back, but not out, then pushed in again. Then she repeated the motion. Then she did it faster. All of his muscles began to contract. It felt amazing! He wanted more! But suddenly her finger was gone. No! A minute later it was back again pushing deep inside him. Yes! But then it was gone again. Why? He wanted more. But suddenly she was pushing on him.
“Roll over again,” she said softly and kindly.
He felt so frustrated as he rolled back over again onto his back. He accepted the baby bottle again and he put it back to his lips while he felt her diapering him again.
She leaned over him. Her voice was almost a whisper. “You did really well today, didn’t you!” It was at that point that he realized that his chastity device had never hurt him at all. Not one little bit. And during that last part, he hadn’t even thought about it.