The Bet - Chapter 25 (Tuesday – week 4 Part 2 of 6)

The Bet
by Karen Singer

Chapter 25 (Tuesday – week 4 Part 2 of 6)

Mel watched the clock. It was just about time. His knock came at her door a minute early. She opened it and smiled.
“Good morning, Mistress,” he said with his usual curtsy.
“Good morning, Sissy,” she said as usual, stepping back to let him inside. She noticed immediately that he had decided on wearing slacks once again. Not a problem. But one day this week she knew that he would be forced to wear a skirt to work again. Probably Friday. She had a feeling he would try to put it off as long as possible.
She took his bag of empty bottles from him, but she didn’t bother to look at them – there was really no need. They were always perfect. She stared at him carefully, looking him over critically. His shape was really much better today. She remembered putting the instruction in his note for him to wear the waist cincher and there was no doubt that he had it on. She smiled – yes, he was really looking good now. She noticed that he was wearing high heels once again instead of the low heeled shoes he usually wore, but his slacks didn’t seem as short as they should have. She was puzzled. “I don’t remember those slacks being that long,” she stated.
He seemed to sigh with frustration before he replied. “They’re not. It’s because of the girdle and the waist cincher. The pants ride down too far on my hips now.” He grabbed the waistband of his pants and pulled them up, then released them to show her his problem. The pants fell right back down where they were before. They obviously wouldn’t stay up as high as he wanted them to. “I have to wear the heels or the pants drag too much on the ground. They don’t fit right with the waist cincher.”
She nodded as she suppressed a small giggle. The waist cincher was giving him a much more feminine shaped waist. But she was glad he had found a way to deal with the problem of his pants. “They look good with those shoes though,” she finally replied, letting him know that she approved of his solution.
Chad stood there for a moment, then he finally asked. “Mistress, what should I do when I have to wear the longer slacks though? I don’t have any heels that would be high enough.”
Mel shrugged. “Don’t wear them.”
“But I need them. I only have four pairs of pants.”
Mel smiled. “You’ll just have to wear something else.” She turned and walked off toward her kitchen with a devilish smile on her face. “Come along now, Sissy. I’ve got your breakfast ready.” As she led him into the kitchen though, her mind was concentrating on only one thing. If Chad couldn’t wear the new, longer length slacks, then he was now going to have to wear skirts to work more than once a week. She giggled slightly again as she wondered when the next day would be. Thursday? Probably.
Chad’s mind was on the same thing as he followed her into the kitchen. It would mean yet another day in skirts – at work! Damn! It wasn’t something he was looking forward to – at all! As he climbed up into the highchair, he asked. “Is there any chance I can buy some more slacks that fit better?”
Mel paused before she put the tray into place. “Maybe, Sissy. I’ll have to think about it.”
Chad never looked forward to her baby food breakfasts, but he had no choice in the matter. In just a few minutes, he had a bib around his neck and was shoveling baby cereal into his mouth… as much as he was able to get into his mouth without it dripping off of the tiny baby spoon he was using. Maybe he should try to put less on the spoon so it wouldn’t drip so much. Of course, then it would take him all that much longer to eat… not to mention that more of the foul cereal would wind up in his stomach. That was the only good thing about trying to eat with the tiny spoon - much of the cereal wound up on his bib or the chair and he didn’t have to eat it.
Mel sipped at her coffee as she watched him struggling to eat his breakfast. Yes, he was a real joy to watch. It certainly brightened her morning every day. But that reminded her, he was going to probably have an interesting evening later, something he didn’t know about yet. Which reminded her of something else… What was he going to be doing with the rest of his day today – while he was at work? Thoughts of him spending yet more time with his friend Robin filled her head. “Are you going to be working today, or reading magazines again?”
He shook his head. “I don’t know. It depends on how soon the client lets us know what he wants.”
Mel wasn’t exactly happy about that, but what could she do about it? “How long does that usually take?”
“Usually a few days at most. But this time we’re hoping to know right away. We really did some super work for them. I can’t see where they wouldn’t like anything we’ve got.”
Mel knew there was no help for it and it was silly, but she couldn’t help it. She was jealous of Robin and the time she spent with him. But he worked with Robin… it was part of his job. Was there any way she could limit the time he was spending with her at work? It was something she’d have to think about.

Chad shifted uncomfortably in his seat as he drove to work. He had wet himself a few minutes ago and now the wetness had worked its way toward the bottom of his diapers a bit… and for some reason, it was irritating his backside. He hadn’t expected that. He did coat his backside liberally this morning with the baby lotion, but it seemed that it wasn’t working very well yet. He had only wet his diapers once so far today. He was now a bit concerned over wetting them even more.
He pulled into a parking space and got out, forcing himself to ignore the urge to rub his padded and irritated backside as he walked into the building. He turned his computer on and sat down, a bit more carefully than usual. Not too bad, just a bit itchy on his bottom. As he checked his emails, the irritation faded to a more tolerable level that he hardly noticed.
“Hi Chad,” Robin called as she walked past his cubicle.
Chad looked up from his monitor but Robin had already passed. “Hi Robin,” he returned over the cubicle wall.
Two minutes later, Robin was at the entrance to his cubicle again. “Any word yet on the project?”
Chad turned his chair around to face her. “Not yet. I just checked the email. Although it is a bit early yet.”
“Yeah, I was just hoping. That’s all. So what are we supposed to do again today?”
He shrugged. “No clue! I’m not sure I want to read anymore magazines again though.”
Robin nodded. “Ok. Let me know if you do though. I’ll see if I can round up some more.”
Chad watched as Robin left and went back to her own cubicle. He turned around and opened up the spreadsheet he kept for the bet. Next to the date for yesterday, he entered twenty five minutes. He stared at the number. Geez! He was going backwards. But really, yesterday had been a bit tough in a few ways. He supposed that he probably could have tried harder while Robin had been sitting with him yesterday afternoon. Why hadn’t he? He vowed that today he would do better… well, he’d do better this afternoon anyway. He always had way too many bottles of Mel’s tea in his system in the mornings to control himself much.
He stared at the number of days still left. Thirty eight. He shook his head. A very, very long time still. Thirty eight more days of total… complete… humiliation. He hated it. But then he had to admit to himself that he loved it too. He was living his fantasies… and then some. It was the “and then some” part though that was bothering him the most. Who would have ever thought that he would be dressing completely as a female… all the time – even to work! Damn! And wow did he need some relief!
He glanced at the last part of his spreadsheet. Self-respect, friends, and a life! Worthy goals – and his main reasons for winning. He had none of those things now. Not at all! Yet he was living his deepest fantasies… and then some.
It would be so easy to make it look like Mel had really made him incontinent, so she could win and he could continue living the dream. Of course, he knew he’d have to fake it. There was no way she could really do it to him. Although he had to admit, there had been a few times already when it had seemed like she had already done it. Troubling times… yet also thrilling.
One thing he had learned in all this though, was how much he really did love wetting his diapers. And it was really so much easier than having to go find a toilet to use somewhere. Much easier, not to mention how really good it felt every time he wet himself. He was surprised at how good it always felt – every time! He never would have imagined it before.
Live the dream… With nothing better to do, he allowed his mind to drift into the fantasy of being totally incontinent, completely unable to control himself in any way… sucking on pacifiers, drinking from baby bottles… and not to mention wearing high heels and skirts. Totally conflicting fantasies – yet they were his fantasies… and he was living it all right then – in reality!
What would happen if he really did go along with Mel’s program? Maybe even tried a little extra harder to achieve his goals? Would it really happen? Could he really do it? He imagined it again, the total humiliation as he wet himself uncontrollably… And as he imagined himself wetting himself in his dream, he also began wetting himself in real life. And he loved doing it. And his need for sexual release went up several more notches.
But he was quickly reminded that he had no way to get any relief at all, and the frustration sunk heavily into him once again. He sighed with frustration as reality crept completely over him and he realized what he could and couldn’t have. It would never work anyway. He knew himself too well. Mel couldn’t actually make him incontinent, no matter how much he tried to go along with it.
And then there was the rest of it too – self respect, friends, and a life. Were they really worth it? Deep down, he knew that they were. But remnants of his dream still crept around the edges of his mind. Were his reasons for winning really that important? Really?
Frustrated, he closed the spreadsheet. Now what was he supposed to do with himself?
He sat back in his chair and stared at the walls of his cubicle. It was a bit like standing in Mel’s corner… or was it his corner? Either way, it was boring. Although standing in her corner hadn’t been quite as bad last night since he had been thinking about something interesting. And that turned his mind back once again to his new favorite subject. Just what would he do if he could get hard again? He knew it would feel great. He knew he wanted it. He just didn’t know exactly what he would do. And why, why, why did he keep thinking about something going in and out of his backside now instead of what it would feel like to stimulate his cock instead. It made no sense. Yet for some reason, it was easier to imagine the feelings from his backend than from his front! Why? Probably because of the damn chastity device and because he needed relief too much. Damn!
“Hey Chad.”
Chad nearly fell out of his chair as Robin’s voice startled him so much. He came to reality and saw her standing in his cubicle. “Yeah?”
“I’m going down to get some coffee. Want to come? There shouldn’t be anyone down there for you to worry about right now.”
Chad considered her offer. It would be nice. He wasn’t sure he needed any more to drink again this morning, but getting away from his cubicle for a few minutes would be a welcome change, especially since they didn’t have anything to do anyway. He nodded his head and smiled. “Sounds good,” he finally replied as he pried himself out of his chair. Getting up changed the pressure on his backside once again and he felt the tingling from his diaper rash. Once again he had to force himself to not rub it.
As he walked with Robin toward the break room, he felt the need to pee come over him yet again. He quickly checked his watch so he could time himself… not that he thought he would be holding it very long since it was still morning.
As they entered the break room, he was a bit annoyed to see another woman there making a fresh pot of coffee in one of the coffee pots. He also wasn’t happy to see her looking him over all too carefully and smiling, almost wickedly, at him. He tried to ignore her as he picked up a full pot of coffee and poured himself some.
“Hey, look! Doughnuts!” Robin exclaimed as she headed further down the counter toward several large, flat boxes.
Chad had been so intent on looking at the other woman that he hadn’t noticed the doughnuts. He was a bit hungry… baby cereal didn’t exactly fill him up much every morning. He carried his coffee over to the donuts and selected one – sugar-coated and filled with raspberry filling… yum! He stood back, waiting for Robin to finish pouring herself her coffee before walking back to their desks with it all. But as soon as Robin poured her coffee, she headed to one of the tables instead. “You’re not going back?” he asked.
“Why? It’s a lot easier to eat these here. Besides, what have we got to do back there anyway?”
Chad shrugged his shoulders and joined her at the table. It was good to get away from his desk for a while. And at least there was just the one other woman still there… hopefully, she’d leave soon. He carefully took a bite of the doughnut, enjoying the fresh taste of the raspberry filling as it filled his mouth.
“Hi Robin. Hi Sissy.”
Chad looked up in horror as the woman sat down with them. She had called him Sissy! And he didn’t even know her name.
“Hey girl,” Robin replied, obviously the two women knew each other well.
“It’s about time you got away from that desk and got out to see the world,” the woman said directly to Chad.
Chad was stunned and totally at a loss as to what to say. “Uh… I guess so,” he finally replied.
“By the way, you’re looking good there, Sissy. Real good. Better than last week. Did you lose some weight? To me, you look thinner.”
“You know,” Robin added. I was wondering the same thing. You are looking a lot thinner. In fact you look like you’ve lost a lot of weight recently. What kind of diet are you on?”
Chad wasn’t really sure what to say. His apparent weight loss wasn’t really from any kind of diet, it was mostly from the waist cincher and the girdle. Of course, he had been eating a lot of baby food lately… far more than he was happy about. He supposed that might have added to the affect. “Uh… he finally blurted out. I’ve been eating a lot less… and a lot more of the basics too.” How much more basic can you get than baby food?
“We’ll sister,” the woman replied, “whatever it is, it’s workin’ for you. It’s working, girl!”
“Uh, thanks,” Chad replied. Being referred to as ‘girl’ was both exciting and humiliating at the same time. He quickly shoved a lot more of his doughnut in his mouth. Not only would finishing it give him an excuse to leave, but it’s hard to answer questions with your mouth full.
“So how’s the baby,” the woman asked Robin?
Chad was grateful that the conversation finally moved away from him. Robin could talk all day about her son… which was just fine with him. He took the opportunity to finish his doughnut and coffee while Robin and the woman talked. Since he wasn’t the center of the conversation, he enjoyed it a lot more. Why couldn’t the women always leave him alone? Why did they have to make such a big deal about the way he was dressed all the time? Was it that exciting that they always had to talk about it? He rolled his eyes at his own thought. Yeah, in their shoes, he’d probably be just as excited and curious… what was he talking about? He was in their shoes – in a way. Wasn’t he wearing high heels on his feet too?”