The Bet - Chapter 47 (Wednesday – week 7 Part 2 of 8)

The Bet
by Karen Singer

Chapter 47 (Wednesday – week 7 Part 2 of 8)

Robin pulled her car into the parking space and turned the engine off. But she didn’t move to get out of the car. For the first time all week, she didn’t actually dread going into work. Which meant, she really didn’t dread seeing Sissy.
She sat without leaving her car because everything seemed so different now. She was entering a new role in their relationship. A role she wasn’t familiar with at all. She also wasn’t even comfortable with it. But right now, it was the only role that would work for her. So… she would go with it… for now. At least, till she figured out something better. But going back to their old relationship just seemed totally out of the question. Totally! She couldn’t think of him as a man anymore, that just didn’t work. And she couldn’t think of him as one of those transsexuals either, because he wasn’t really. He was… a sissy. It was the only way she could adequately relate to him now. Anything else only made her angry. A sissy… and he… craved being dominated and humiliated. How bizarre!
She grabbed her things and with fully loaded arms, worked her way out of the car. Dominating someone wasn’t really her, yet she was about to do it. And the strangest thing of all was that, because of that, she wasn’t dreading seeing him! Something about it was feeding her a tiny boost of confidence, of power. But it was only a tiny amount because she didn’t really know how to go about doing what she would be doing – whatever it was that she would be doing. Maybe she should email Mel and see if Mel could be a little more forthcoming with some of the help she had offered at lunch yesterday, because she really had no idea of what to do with him.
As she was passing his cubicle, she noticed that he was already at his desk, booting up his computer, but she didn’t bother stopping or even pausing. Her arms were full and she just wanted to unload them. As soon as she reached her desk, she carefully dropped the whole batch of things she was carrying onto her desk. She really needed to stop bringing so much. She rarely used most of it anyway. But… what if she needed it? She opened her purse and dug her mirror out and checked her face and hair, then she stowed the mirror away and put her purse into her desk drawer. She stopped and stared. Now what?
She pushed the button to start booting up her computer, but her mind wasn’t on her computer, her mind was on Sissy. Now what was she supposed to do with him? Did she have to think up something to make him do? Or did she have to pay any attention to him at all? This domination business was confusing! Especially when you didn’t have any idea of what you were supposed to do!
She supposed she had better at least talk to him. Tell him good morning. But should she? Why should she make the effort if she was supposed to be the one in charge? “Sissy,” she called over the wall. “Are you just going to ignore me all day? Get over here and at least say good morning. Let me see what you’re wearing today.”
Chad was very surprised to hear her calling him. He quickly got up and went over to her cubicle. “Hi Robin,” he said somewhat brightly in his girly voice, hoping she would be in a good mood for a change.
“Hi Si…” Robin stopped before she got any further and stared at him for a moment. “Hey,” she said a bit perturbed, “weren’t you supposed to be using only your sissy voice around me from now on?”
Chad blushed. He had remembered, he had just been hoping that she hadn’t really wanted him to do that… or perhaps that she had forgotten. “Sowwy,” he said in his sissy voice.
Robin nodded as if more satisfied, then she shook her head. “Just like a child. Always trying to get away with something!”
Chad blushed, he really hadn’t meant… okay, so he did try to get away with it. And he guessed it was a bit childish. But… It was just so embarrassing talking like a sissy all the time! And here at work especially! What if someone else heard him?
“The zebra print again,” Robin remarked with a smile about his dress. “I haven’t seen that dress in a little while now.”
Chad smiled. “I just thought I’d pull it out again.”
“Well, it still looks pretty good on you. Which reminds me… Now that I know a little more about what’s going on and there are less… secrets between us… So tell me, how did you really lose so much weight so fast? I still find it hard to believe that it’s all due to some diet you’re on.”
Chad hesitated before speaking. He wasn’t sure just how much of the truth he wanted to tell her. But Robin saw him pausing and immediately figured that he was going to try to hide something again. “And don’t try to hold back on any of the details,” she said sarcastically, knowing now that he couldn’t be trusted, “because I’ll be checking with Mel to make sure you tell me all of it.”
Chad was shocked. She would ask Mel too! But tell her all of it? Some of it was awfully embarrassing. “Well,” he started, trying to search for what he should tell her. “Um… Most of what I cook really is diet dishes. I have this great cookbook that I use to help me.” He didn’t add that it had been a while now since he had eaten any of the dishes he had made out of that book since Mel had been keeping him on mostly baby food lately. “And… um…” He wasn’t sure what else he should really tell her.
Robin could see that there was definitely more to it than the diet cookbook, especially since he looked so embarrassed about it. “And what else?” she asked. “I know you’ve got to be doing something other than just eating diet dishes. I eat nothing but diet dishes. I have for most of my life. They don’t help!”
Chad didn’t really want to add any more but she wasn’t giving him much of a choice. He decided to go with the most obvious. “Um… Well, what I’m wearing under this dress has a lot to do with it too.” He finally said.
Robin sat back in her chair and smiled. “What you’re wearing under that dress? That’s another subject I’ve been dying to ask about for a while now. Just what are you wearing under there? I know those breasts aren’t real, but what else do you have under there?”
Chad hesitated a bit because he was embarrassed to talk about it. “Well… um… under here I have this kind of all-in-one girdle thing that’s really tight.”
“Girdles are supposed to be tight,” Robin commented.
“Well, this one is extra tight. Mel got them too small to begin with, then later went down another size. It’s not fun, believe me.”
“Oh, I do believe you. I’ve never worn a girdle that was fun. So, anything else?”
Chad actually blushed a bit as he hesitated before answering again. “Um… Under the girdle, I’m also wearing a really tight waist cincher too.”
Robin’s eyes went up. “And that’s under the girdle?”
Chad nodded. “Yeah. So it’s all extra tight and compresses my waist so that I really can’t eat all that much anymore. And I think that had a lot to do with me being able to lose so much weight so fast.”
But Robin wasn’t so sure about everything. “So, while I’m sure you have lost some weight, it could be really all those tight things that just makes it look like you’ve lost much more. Right?”
“Um… Yeah. That’s some of it. But I have lost a lot of weight!”
“Oh, I know you have. It’s obvious.” She looked at him. He had seemed very embarrassed about telling her about it. The words were out of her mouth before she knew she was going to say them. “I want to see it all.”
Chad was shocked! “You want…”
“Yeah. Take your dress off. I want to see everything you’ve got on under there.”
Chad just stared at her for a few moments in total shock. He couldn’t believe it! “Here?”
“Yes, here!”
“I mean… now?”
“Of course!” Robin replied more agitated. “Now get that dress off so I can see everything you’ve got on!”
Chad still couldn’t believe it! He looked around to make sure nobody was near her cubicle, then he slowly started removing his dress.
Robin sat in her chair enjoying what she was seeing. No, it wasn’t at all like a man doing a striptease for her. Not one bit! But still she was enjoying watching him undress immensely! And the fact that he seemed to be so embarrassed about doing it added a bit to her thrill too. A moment later, she smiled broader as he stepped out of his dress. Now she could see his all-in-one girdle. Only his pantyhose covered part of it. She could also see a little bit of his breast forms now too. But now she saw him pausing, obviously he either didn’t know if he should continue or not. “All of it!” she said. “I want to see everything!”
Everything? Chad actually shook a bit at that. He also wasn’t sure he wanted to show her everything. But then, he also hadn’t wanted to show her this much either. He tried to figure out what he should remove next. Maybe he could just peel down his girdle to show her the waist cincher underneath. He started to pull the straps off of his shoulders.
“Don’t you need to remove your hose first so you can get that thing off?” Robin asked.
Chad stopped what he was doing. Obviously, she really was serious about seeing everything. Not having much choice, he removed his shoes, then he carefully peeled down his pantyhose and pulled them off as well.
Robin felt like laughing – although she didn’t. Oh my, this was fun! Who would have ever thought? And the fact that he seemed so reluctant to strip in front of her like this was making him do it slower, so she was enjoying it more. She actually leaned forward when she saw him starting to peel down the obviously very tight girdle he was wearing. She was very surprised when it fully uncovered his breasts and they didn’t fall off of him. They just stayed right where they were as if they were real breasts. Huh? Now his waist cincher was revealed as he struggled to pull the girdle down. But her eyes were still on his breast forms. They were somehow stuck to his chest! But a moment later, her eyes were torn from his breasts to something else as his plastic panties started to come into view. She stared as if transfixed. Yes, she knew now that he was wearing diapers, that was part of what his whole bet was about. But still, she hadn’t thought about it much.
He was struggling more now to peel the girdle down over top of his diapers. She could see how really tight the thing was. He hadn’t been kidding about that at all. And then the girdle moved down a bit more and finally came free. He pulled it all the way down and stepped out of it. He was staring at the floor, obviously too embarrassed to look at her. Well, that was just fine. In fact, she rather liked it. But she couldn’t help staring at the childish pattern on his plastic panties. Where had he gotten those? She saw him starting to reach for the fasteners that held his waist cincher together. “Do you have anything under that thing?” she asked.
He shook his head. “No,” he said simply, still unable to look at her.
“Then don’t bother to take it off.” But she was so fascinated by what she was seeing that she didn’t even realize she was getting up till she was out of her chair and moving closer to him. Staring at the odd breasts dangling from his chest, she reached out and touched one. It felt… soft… but firm too. Almost like a real breast. She almost laughed. She had touched it and it still hadn’t fallen off! She grabbed one and pulled a bit. It seemed to be stuck – firmly! She pulled on the other one too and found the same thing! She looked up at his face, although he was so embarrassed that he was still staring at the floor. “How do you get them to stay like that?”
Chad couldn’t believe how embarrassed he felt standing like he was in front of her in just his diapers and waist cincher. “Uh… They’re glued on,” he replied.
“Must be fairly strong glue,” Robin remarked.
Chad nodded. “It is. You’ve got to use this special stuff just to get them off.”
That surprised her. “You do? You mean you don’t take them off every night?”
He shook his head, still staring at the floor. “I can’t.”
She was surprised. “You mean… you can’t get them off? You have to wear them all the time?”
He just nodded. “Mel removes them once a week, but only overnight. Then she glues them back the next day.”
Robin almost laughed. “So it’s almost like you have real breasts. You can’t go anywhere without them.”
Chad didn’t bother replying. He just continued to stare at the floor.
But now Robin’s attention was turned to what he was wearing further down. She reached out and tentatively patted the patterned front of his plastic panties. They seemed thicker than she would have imagined. Her son’s diapers were a lot thinner than what he seemed to be wearing. “Pull those panties off too,” she said as she stepped back to give him more room.
Chad’s eyes bulged wide! But he slowly stuck his fingers into the waistband of the panties and started to work them down over his wet diapers. He didn’t really want to take them down at all, so he pulled them down just a little and held them there.
“What are you stopping for?” Robin asked.
Moving quickly, because otherwise he couldn’t have done it, he pulled the plastic panties all the way down and stepped out of them, discarding them on top of the pile with all the rest of his clothes on the floor.
Robin stared at his diapers as if transfixed. And then she noticed that the bottom of them appeared a bit wet! But then she figured that they probably should be wet. She just hadn’t expected to see it so plainly. But they still seemed to be thicker than she would have thought they would be. She again reached out and patted the front of them, right over top of the wet area. They were thick! Wait a minute! “How many diapers do you have on there?” she asked.
Chad held up two fingers as he softly replied, “Two.”
“Two? But aren’t they disposable ones? What do you do, rip the plastic off of the first one?”
Chad shook his head. “No, we just cut slits in the cover… all over.”
Robin nodded. “So what I’m seeing as wet now, is really spill-over from what the diaper underneath couldn’t handle?”
Chad only nodded.
Robin reached out and felt the front of his diapers again, now trying to feel just how wet he really was. But in doing so, she encountered something strange. It felt like there was something hard inside there. She tried to grab it through the material and discovered that there really was something hard there! “What’s that?” she asked totally surprised as her hand actually managed to somewhat grip the thing even through his wet padded diapers.
Chad didn’t want to answer at all. But her hand was still holding on tightly and the teeth inside the device were hurting him a bit. Still looking at the floor he stammered, “Um… M… My... ch… chastity device.”
Robin was shocked. “Your what?”
“My… chastity device,” he repeated.
Shocked, Robin let go and pulled her hand away. She didn’t know if she should laugh or what! “Your chastity device?” she asked, finding it hard to believe what she had just heard. He only nodded as he continued to stare at the floor. “Really?” she asked, totally dumbfounded. But he only just nodded a little again. She was curious about it. What did it look like? How did it work? In her mind, all she could picture was a huge belt worn by medieval women. But what she had felt didn’t feel anything like that. But did she dare make him strip totally naked? And especially here at work? But she had already gone this far and besides, the other people in the company didn’t come around where they worked too often. But… could she really make him strip totally naked? Did she have that right? She looked at him. He was still standing bashfully staring down at the floor. She was surprised that she actually asked him… “Can I see it?”
He looked up quickly, shocked once again. He swallowed hard. “You… you really want to see it?”
She nodded. Almost contritely she replied. “I’ve never seen one before. So… that is, if you don’t mind and… if it’s not something that you feel you shouldn’t do.” A bit frustrated she added. “I don’t know what the bounds are of things I can order you to do or not.”
Chad stared back down at the floor again as he shook his head. Very quietly he replied, “That’s just it, there are no bounds.”
“No bounds?”
“Well, not unless it’s something that would go against Mel’s wishes,” he added. “She has to come first to me.”
Robin shook her head. No bounds? She could order him to do anything? That was a lot to swallow. But as she looked at him bashfully staring at the floor again, she knew without a doubt that it was true – at least as far as he was concerned. And she fully understood why Mel’s wishes had to come above her own. “So that means… if I want to see it, then you have to show it to me?”
Silently he nodded – still staring embarrassedly down at the floor.
“So what are you waiting for?”
Chad paused only for a moment before tearing his eyes from the floor to his diaper. He started to reach for the tapes that held the outermost diaper closed, when he realized one big problem. He looked up at Robin who was watching him intently. “But if I pull these open, I won’t be able to stick them closed again.” He was starting to feel a bit elated over the fact that he wouldn’t have to show her after all.
Robin blinked. He was right! And that would be a problem. “Do you have any more diapers?”
“Only out in the car,” he replied, worried that she might actually send him out to get them.
Robin had to think about it for a minute. Was it worth it? She watched him standing in front of her wearing only diapers – wet diapers at that – and that waist cincher. Did she want him to get all dressed again just to go out and bring in more diapers? Was it really worth it? She took one more look at him. Hell yes! “Get dressed,” she ordered. “Go get them! You’ve got nothing better to do anyway. Not as far as I’m concerned at least.”
Chad couldn’t believe it, she actually wanted him to get all dressed, go out and get his diaper bag, and then he would have to get all undressed again – just so she could get a look at his chastity device!
“Well what are you waiting for?” Robin asked. “Hurry up!”
Chad grabbed his plastic panties from the pile on the floor and started to put them on.
“Can’t you skip them,” Robin asked. “Just throw your dress on and forget everything else. Let’s make this quick!”
Just his dress? But he figured he could do that with no problem. He slipped the zebra print dress back on and slipped his shoes onto his feet. Then without another word, he hurried out to get his diaper bag.
Robin chuckled to herself as she watched him leave. He was actually going to do it! She finally turned to her computer and turned it on.