The Bet - Chapter 17 (Monday – week 3 Part 2 of 3)

The Bet
by Karen Singer

Chapter 17 (Monday – week 3 Part 2 of 3)

Mel checked her messages between clients and saw one from Will Grey. She had been waiting to hear from him about the case. She dialed his number. “Hi Will, it’s me.”
“Mel! Hey listen, I just wanted you to know that we just made a small bust on some of the info your favorite kid client gave us last night. We’ve got another one lined up for a little while from now.”
“So we’re good with him then? You can let him go?”
“Just as soon as you tell me you’ll go out to dinner with me tonight.”
Oh God! And worse, he sounded so smug. “Will, not tonight,” she protested trying to put it off. “I’ve already got plans.”
“No problem. I can easily hold the kid for a few more days till we know everything we’re gonna get from these other raids. And you know how long the paperwork can take.”
Shit! He was so damn manipulative! And the kid’s parents had already called twice this morning. They wanted him home. She hated herself. “How about tomorrow night? I’m free then. Will you let him out this morning if we go out tomorrow instead?”
She could almost hear him thinking. “Tomorrow it is!” he finally agreed. “You can come down and sign the papers anytime. I’ll have them ready.”
She breathed a sigh of relief, sort of. She still dreaded going out with him. “Thanks, Will. I appreciate it. I’ll be down in a little while. Just as soon as I call his parents.”
“Oh, and Mel… don’t forget, I expect you to look good tomorrow.”
“Yeah, yeah. I haven’t forgotten. See you in a few.” She hung up on him. Geeze! The guy was a pain. “I expect you to look good tomorrow,” she mimicked angrily into the air. But they ran up against each other a lot. She had no doubt that if she didn’t at least try to look a little better, which in his case meant sexier, then the next case he might not be so compliable. It was always give and take with these things… speaking of which, she had a very good phone call to make to the kid’s parents just then.

Chad was working intently when he suddenly felt a hand placed lightly on his shoulder. “Hey Chad,” Robins voice said softly.
He jumped a bit because he hadn’t heard her come in behind him. “Hi Robin,” he replied as he finished typing his line of code. He could feel her fingers feeling for the straps of his girdle under his shirt. “Please don’t,” he said, shrugging her hand away. He turned his chair around towards her.
“I just needed you to look at my idea for one of the pages for this new project,” she said.
“Oh, ok, no problem.” He got up from his seat and followed him into her cubicle. Her design was already up on her screen. “I love it!” he said enthusiastically. “And I have no doubt that the clients will too. In fact, we can use part of that on the home page too if you want. I think it might look good.”
“That was kind of my idea too,” she admitted. “I just wanted to see how you felt about it.”
“I love it,” he said as he leaned back against her desk to look at it more closely.
“Hey Chad,” she said quietly. “Do you know your makeup is a little messed up around your chin? It looks like you wiped some of it off and the areas around it got all smeared.”
He suddenly felt so embarrassed. Why was she looking at his face instead of their work? “Uh… I didn’t know,” he lied. Actually he had totally forgotten.
“You’ve got to be more careful if you’re going to be wearing makeup.”
“I guess I’m not used to it yet,” he admitted. Well, he wasn’t!
“You better fix it,” she said. But she suddenly noticed his necklace half hidden under his shirt. “Oooo. That’s pretty,” she said as she reached out and pulled it out so she could see it better. When did you get that?”
“Friday night,” he said slightly exasperated.
“Your ring too?” she asked.
“Yeah.”
“Nice. I love them.” But before she let go of his necklace, she was careful to arrange it more outside his shirt than inside. “You need to let that show more,” she said.
He wanted to ask why, but he decided not to. It would only lead to more embarrassing conversations.
“Hey, tell me something Chad.”
He was suddenly wary. “Yeah?”
“Why is it you always wear your old male shirts, when everything else that you wear is for women? Don’t you have any pretty blouses?”
“Yeah, I’ve got a few.” He admitted.
“Then why don’t you wear one?”
He tried to find and answer that he could tell her but he couldn’t. “It’s complicated,” he finally replied.
She rolled her eyes and turned away from him, obviously put off.
“Well, it is!” he protested as he started to leave.
“Oh Chad,” she called after him sarcastically. “Don’t forget to fix your makeup!”
He didn’t answer.

Mel was feeling both good and bad when she got back from the police station. Good because the stupid kid was out of jail, and bad because she had to deal with Detective ‘All-To-Smug’ again. When she checked her messages, she was surprised to see one from Sandy. She called her number. “Hey Sandy, it’s Mel.”
“Oh hi Mel. Thanks for returning my call.”
“No problem. What’s up?”
“I just wanted to let you know that I got the highchair back this morning. The carpenter did a really great job!”
“Wonderful! So when will you have it ready?”
“Probably by Wednesday at the latest. Maybe tomorrow night. It depends on how things go.”
“That’s great Sandy. I appreciated it.”
“Well, just don’t forget that you promised to let me babysit someday.”
Mel laughed, but only for a moment. Instead of talking, she found herself saying nothing, thinking long and hard about what she was considering.
“Mel? Are you still there?”
“Yeah Sandy. I’m here… Listen, Sandy. I’ve kind of got this date lined up for tomorrow night…”
“Wonderful Mel. Good for you!”
“Yeah, well, maybe not so good. I’ve been out with this guy a few times before and he’s a lousy date… if you know what I mean.”
“So? Go enjoy yourself anyway.”
“Unfortunately, I’m kind of stuck going out with him this time. Anyway…” she paused slightly for another breath. “I was thinking… if you still want to babysit with him… then how about then?”
Sandy’s squealing was loud enough that Mel had to move the phone away from her ear for a moment. “Tomorrow? You mean it?”
“Yeah, tomorrow.”
“Of course Mel. I can’t wait!”
“Great. I’ll give you the details later. Ok?”
“Super Mel. Super!”

Sandy hung up her phone totally excited. She was going to get to babysit with the sissy. She had no doubt that Cassie would be equally excited too. She was supposed to be searching for fabrics and furniture for a client just then, but somehow she was no longer interested. Instead, she pulled her car into the parking lot of a store that specialized in things for little girls. She needed some ideas and this might be the perfect place to start… oh, and then there was that new baby store further up the street, and then the toy store, and …

Chad stared at his purse. It was almost lunchtime. It had been a good morning. He had gotten plenty of work done and even better, his spreadsheet now proudly announced that he had held back for twenty minutes – and that was a conservative estimate. But his problem now was his makeup. He remembered that Mel had told him to fix it when he got to work. Even Robin had noticed the problem. He just didn’t want to do it. But Mel had said she was going to call Cassie to check up on him. He knew she would. He had the impression that Cassie told Mel everything.
Having no choice, he searched through his purse for the compact that held his little mirror. It was really difficult to see much in it and he felt cross-eyed before he looked away. He pulled out the things he thought he would need. He didn’t have to do all of his face, just a tiny touch up. But the darn foundation could be so tricky. Once he had the things he needed out, he dabbed a tiny bit of makeup over the areas that were bad. Then he grabbed one of his makeup brushes and went to work.
“Cool! I see you got yourself some brushes too,” Robin’s voice said from the entrance to his cubicle.
He suddenly felt very embarrassed by what he was doing. “Yeah, you said I should.”
But Robin was now looking at the makeup on his desk that he had pulled out. “Hey, this is some new stuff. You didn’t have this last week.” She picked up one of the bottles. “Oh, this is nice. I love it, but I can’t always afford it.”
“Yeah,” he answered. “Well, I don’t really buy all that much anyway.”
“Lately you seem to be.”
He had to admit, she had a point. “Maybe,” he answered noncommittally.
“Hey,” she said. “I’m going to lunch. Want to go?”
“No, I can’t,” he replied.
“Another date?”
“Something like that.”
She stood there for a moment looking at him, wondering what was really going on. “Ok, suit yourself,” she finally said before she left him. Did she want to follow him again? Not really… but…

Chad struggled with his face, trying to fix it the best that he could. By the time he was done though, he knew he was going to be a few minutes late meeting Cassie. He hurried out to his car and drove to the exercise place where she worked.
“Hi Sissy.” The receptionist called out way too loudly as he walked in.
“Uh… hi,” he replied.
The receptionist suddenly put a funny pout on her face. “I’m disappointed. You don’t ever curtsey pretty when you talk to me.”
Why did this woman want to tease him so much? Why did any of them want to tease him for that matter? “Knowing that she’d only make things more difficult than they already were, he dropped a quick curtsey for her and said “hi” again.
She giggled terribly! “Oh, you’re sooo sweet! I’ll find Cassie for you.”
Chad was just grateful that she hadn’t delayed things any longer. The receptionist was back a few minutes later with Cassie. Chad didn’t wait this time, he immediately dropped another curtsey as he greeted Cassie.
Cassie smiled. “You’re learning, Sissy. I’ve got to say that much for you. You’re learning. But are you learning anything else? That part we’ll have to see about. She crooked her finger as she turned around and Chad followed her toward the back. He was suddenly not looking forward to getting his diapers changed again.
Once again in the back office with the blinds closed, Cassie had him get undressed down to just his diapers while she pulled one of his baby bottles out of his diaper bag. She had him lie on the floor to change him again and handed him the bottle to suck on. She removed his diapers. “Oooo, not messy again?”
“I haven’t had any suppositories in a while now,” he replied.
“And why is that?” she asked. He shrugged as best he could while on his back. “Don’t know,” he said around the nipple in his mouth. “I guess Mel’s been too busy.”
Cassie didn’t say anything to that. She just removed his diaper and put two fresh ones under him. “Ok, let’s get down to business now.”
Chad was already mentally preparing himself for the pain… dreading what was to come more than ever.
Cassie squirted some baby lotion into her hands and began messaging what she could touch on his front side. To Chad, it felt like heaven. He wanted more, much more… while at the same time he didn’t want it at all because he knew that in the end it would hurt. He tried very hard to keep what Cassie was doing somewhere in the back of his mind while he attempted to think of work issues instead. It was working – sort of. At least his chastity device wasn’t hurting him yet.
“You’re doing so well,” she said softly. But she wasn’t stopping. “Raise up your bottom a bit so I can coat your rear end too. He did as he was told and soon felt her warm hands massaging his back side. It too felt incredibly good. But then she was moving closer to his tiny little hole. And the feelings seemed to increase ten-fold. She touched his hole, and he moaned. She noticed his reaction and was a bit surprised by it. She touched it again and felt him pushing himself ever so slightly towards her finger. “You like that?” she asked softly.
He didn’t answer. He was too wrapped up in how good her hands felt and wishing more than ever that she would touch him there again.
She touched his asshole again, only this time she left her finger there. Once again he was pushing against her finger. She glanced at his face. His eyes were closed. He was sucking on his baby bottle furiously again. Ever so slightly, she increased the pressure of her finger till it slid just barely into him. She saw his whole body shiver. She removed her finger. He was breathing faster now, his baby bottle would be finished soon at the rate he was sucking on it. She quickly grabbed one of the suppositories and got it ready. Then she went back to playing with his tiny asshole. Again, she put just enough pressure on it to where he was trying to push against her finger again. Then she pressed it inside, further this time. All the way to her first knuckle. She slid it in and out a few times then removed it. His eyes were still closed and he was still sucking furiously on his bottle. He was breathing hard. The base of his cock was now more swollen than it was before, yet he wasn’t complaining.
She picked up the suppository and held it against him till he started pushing against it, then she slowly slid it in along with her entire finger, as far as she could push it. She saw his face wince in pain as the teeth of his device dug deeper into him. She pulled her finger out again. She doubted that he even knew she had put the suppository into him.
She moved her hand back to his ball sac and his rear end automatically dropped back down to the floor. She massaged him again and again till he began moaning. She could see that he was so thick now inside his device that it had to be hurting him. She wanted to do more for him, but the darn plastic device was preventing her. She grabbed the whole thing in both hands and pulled gently on it. He groaned as his trapped cock tried to become fully erect in the tiny space that it had. Once again, he pushed her hands away and rolled over onto his side, trying to quell the pain.
When she felt he was more under control, she rolled him back over and took his empty bottle from him. Then she finished diapering him. “You did pretty good again today,” she said, but you’ve still got a ways to go. I think you enjoyed that today more than you have before.”
Chad felt his face burn with shame. He didn’t know what to answer. It had felt good. He was just now more horny than he had felt in a very long time. “Can I go now?” he asked, still deeply embarrassed.
“Yeah,” she said. “Get some lunch.”
He hurried out and back to his car, never once looking at anybody else. He himself was still trying to figure things out. Why had it felt so good when she had played with his asshole? He wasn’t sure he liked any of the implications of that.

“Hi Mel, it’s Cassie.’
“Hi Cassie. Everything go ok today?”
“Yeah, just fine. Hey, I noticed something different today.”
“Different?”
“Yeah. When I played with him trying to get him hard, he was doing real well till I started playing just a bit with his asshole. Touching it kind of kick-started his system. It was like he wanted me playing with it.”
Mel had to think about that for a moment. “Ok… Um, have you ever noticed that before?”
“No, never. How about you?”
“I’ve never played with that – other than to shove suppositories up his butt.”
“Never?”
“No, why?”
“You don’t get out much girl, do you?”
“Not as much as I probably should. But I am going out tomorrow night – with someone I’d rather not be going out with at all. Did Sandy tell you?”
“No, I haven’t talked to her today.”
“Yeah, I’ve agreed to let her… and I guess you, babysit with Sissy tomorrow night while I’m gone.”
“Oh hey! That should be fun! I know Sandy’s been jealous because I get to play with him every day and she doesn’t.”
“Well, she can have at him tomorrow night then.”
“Great. I just wanted to let you know how it went today, that’s all.”
“Ok, thanks Cassie. I’ll talk to you later.”
Mel hung up her phone. What a strange conversation. So his asshole was becoming more sensitive lately. That was interesting. Had she read something about that? She’d have to look it up. And first chance she got, she’d have to experiment for herself.