The Bet
by Karen Singer

Chapter 33 (Wednesday – week 5 Part 4of 8)

“There you are,” Robin replied happily as Chad came back to the front with Cassie. “You don’t look all worn out.”
Chad shook his head. “Trust me, I don’t think I can take much more!” He headed for the door and Robin followed.
As they went out, Robin took a good look at his crotch as well as his backside as he walked in front of her. She had been right, she had just imagined it. No, his crotch didn’t really look all that feminine, but it wasn’t really bad either. And his backside didn’t look all that big at all – just its usual size, which she couldn’t quite remember if it was actually bigger than she remembered it used to be or not. “So what do you want for lunch?” she asked as they got into his car.
“Something I can sink my teeth into!” he replied. “I’m hungry!”
“Yeah, dieting is tough! I ought to know!”
Chad wasn’t really dieting, but she didn’t know that.
“Hey,” she said, “Since we don’t have much time, how about just stopping at the first fast food place we come to. Most of these places have salads available.”
“Fine with me,” Chad replied, although he planned on getting a lot more than just a salad to eat.
A few minutes later, he pulled into the parking lot of a fast food restaurant and they went inside, although Chad would have preferred to stay in the car. Whenever he went inside these places, he got way too many interested looks.
Robin ordered a salad for herself like she said she would. “A salad for you?” she asked before Chad could give his order.
“No, I was thinking of trying their Mega-Burger instead. And I definitely want fries!”
Robin laughed. “Silly. Don’t even joke about it! If you’re going to be dressing like a woman then you better be eating like one too. But you’re right, I do wish I could eat something bigger. And I ‘adore’ fries.”
Chad was about to order the Mega-Burger, but after Robin’s comment, limited himself to just the same salad that she had ordered. But then as an afterthought, he ordered a large order of fries too. “You can share them with me, if you want,” he offered.
“Deal!”
As soon as they sat down to eat, Robin asked, “So what kind of exercises do they have you doing? I looked for you during the tour they gave me, but I didn’t see you.”
She had looked for him? Of course she would. “Uh… They have me stuck in the back, out of sight.”
“Why?”
Chad searched for a good answer. “Uh… Because it’s a ladies gym?”
“Oh, that makes sense. I guess you would probably make a lot of them nervous.”
Chad was relieved that she had accepted the answer so easily.
“So like I asked before, what kind of exercises do they have you doing?”
Now Chad had to think quickly again. He knew that she wouldn’t leave things alone unless she was satisfied. To stall, he shoved a bunch of salad into his mouth and chewed on it – not what he really wanted to eat. As soon as he had swallowed he said, “Well, most of the time is spent on… kind of… some stretching exercises.
“Stretching?” She nodded knowingly. “That’s always important. “Are they trying to limber you up? Make you more flexible?”
“Yeah, you can definitely say that,” he replied. “And the funny thing is, that I’m finding that it’s increasing my… uh… sensitivity, in ways I never thought possible.” He almost laughed at his own joke. Sensitivity was right… to his asshole!
Robin stuffed a few more French fries into her mouth. Chad noticed that she was eating more of them than her salad. “Really? Sensitivity? I didn’t know that was possible. But I guess it might make some sense if you’re learning to move your muscles differently.”
“You have no idea!” he replied.
“I’m sure,” she said as she grabbed a few more fries. “So how did you get to join in the first place, since it’s a ladies gym? Did they let you in just because you’re dressing the part?”
Geez she was full of questions! But this time the answer came easily. “Cassie is my neighbor,” he explained.
“Oh, well that explains it. You’re lucky.” But she immediately wondered if Cassie’s apartment was the apartment she had seen him going into the one time she had followed him home to see where he lived. “So what package did you sign up for? That’s my problem right now. Do I sign up for just the six-month package, or do I go for one year, or more? It’s a lot cheaper if you go for longer.”
Chad wasn’t signed up for any package. He wasn’t exercising. The only thing he did there was get his diapers changed. “Um… I guess you could say I’m on a special package, just for me. I think it just goes from month to month.” That was the best answer he could come up with to keep her satisfied.
She nodded. “Must be nice to have a neighbor who works there!”
Chad didn’t answer. Instead he just shoved more salad into his mouth. He was relieved to see Robin digging more earnestly into her lunch, instead of just talking. His relief was short-lived however.
She shoved a few more French fries into her mouth and looked right at him, her eyes bright with excitement. “So what do you wear while you’re exercising?”
“What do I wear?”
“Yeah!”
She seemed so interested. “Uh… not much of anything actually.” And that was certainly the truth!
“Oh come on! That’s one of the most important parts! What kind of outfit do you keep in that pink gym bag of yours?”
“Most important part?”
“Of course, silly. What you wear is always important. And don’t tell me you’re not interested in that because isn’t that one of the main reasons you’re dressing like a woman in the first place? For the clothes? I don’t see this as being any different! So what do you wear?” She giggled. “I’ll bet it’s a pink leotard and tights! I can just see you in it now.” She giggled some more.
Chad’s eyes nearly popped out of his head. “Pink leotard? Uh…”
But before he could continue, she was charging forward with more. “I wonder if you’ve got a pink tutu to wear with the outfit too! Do you?” She giggled again. “I can just see you in that too. Damn, I’d love to see you in that!”
“Pink tutu?” Chad was fairly aghast. Where did she come up with these things? “Uh… not really.”
“Oh come on. I’ll just bet you have one. Isn’t that what all the sissies wear?”
“All the sissies?”
“Well yeah.”
Chad had never worn a tutu in his life, let alone a leotard. “So is that how you’re classifying me now? As a sissy?”
She shoved another fry into her mouth. “Shouldn’t I?”
She did have a point. Besides, he really was a sissy. In fact, Mel had just proven to him that he was a bigger sissy than Robin thought. He couldn’t really deny that much at all. “I guess you do have a point,” he finally replied.
“So, is it a pink tutu, or white, or what?”
“Sorry, not tutu. No leotard either.”
“Darn! That’s no fun!” She grabbed the last of the fries. Chad had gotten very few. “So what do you wear then? And don’t tell me that you just wear shorts and a T-shirt like most of the women I saw there.”
Chad realized that she had just given him a way out. “Okay, I won’t tell you then.”
“Darn you! That’s what you really wear?”
“Uh…” Chad didn’t think he needed to correct her misinterpretation at all.
“But I’ll bet you’ve got some kind of cute saying on your shirt!”
“Um…” He was about to say that he didn’t but he never got the chance.
“What is it?” she demanded with more than a hint of laughter in her eyes.
“Uh… Nothing.” He replied.
“Don’t give me that. “I’ll bet it’s something appropriate for you like… ‘Girl Power’ or something similar. Is that it?”
“Nope! Sorry, you’re way off.”
“What is it then? It’s got to be something!”
There was no way he was going to tell her that he was naked – or just in diapers. How could he explain that he didn’t wear anything? “Uh… It’s nothing really.”
But she didn’t really believe him. “That embarrassing, huh?”
“You could say that!” Again, very much the truth!
But she took his words differently than he intended. “So it is something embarrassing, huh? Tell you what, if I guess it, will you tell me?”
“Guess it?”
“Yeah. Like is it... Oh I don’t know. ‘Fem and Fit?’”
“No. Definitely not! Are you done eating?” he asked, trying to move the subject away from the current one.”
“Yeah. We better get back.”
Chad got up from the table and Robin followed him out. He was glad they were leaving. Talk about awkward.
The minute they were in his car though, she said, “Pink and Pretty!”
Chad just groaned.

Mel’s phone rang as she got back from her lunch with Gloria. She wasn’t the least bit surprised to see that it was Cassie calling. “Hi Cassie. What’s up?”
“Hey Mel. I just wanted to let you know that Sissy’s little friend Robin was back again today. And this time, she’s joining the gym. I’m afraid I didn’t get any time to do more than quickly change his diapers for him. I did make sure he drank his bottle before he left though.”
“She’s back? Now what’s she up to?”
“I think she just wants some exercise. Most of our customers do. I can tell you that Sissy wasn’t at all happy about her being here. He kept asking me to do something so she wouldn’t join – which I won’t do. We need the customers.”
Mel thought about things for a moment. “Okay, Cassie. Thanks. We’ll just wait and see what happens. Okay?”
“Fine with me, Mel.”
Mel hung up her phone. The damn Robin woman again! Now what was she up to? And looking for some exercise? Mel seriously doubted that! She also seriously doubted that Robin needed any exercise at all! But at least it didn’t sound like Chad was in favor of her joining the gym. What was she up to? Robin and her continually increasing involvement with Chad was really starting to grate on her nerves! Eventually, something was going to have to be done!

Gloria watched as her last client walked from the building out to his car. Her next client would be arriving in a few minutes. She purposely tried to schedule them far enough apart that they rarely ran into each other. She wandered back to her office and sat for a few minutes to think. She was going to get her shot with Chad tomorrow night. She needed to figure out a way to make sure he would tell her the whole truth, and at the same time completely minimize Mel’s presence. Because with Mel there, he might still be influenced into giving her answers that weren’t quite correct.
She was a trained psychologist. She had even tried making her living that way for a while. But more and more she had found herself helping people deal with too much stress in their lives. So she had begun offering “sessions” where she tried to teach them to deal with their problems through relaxation. But she quickly found that all her clients were more interested in the sessions with her helping them relax than with them trying to do it for themselves. So she had delved deeply into the subject of relaxation therapy, and the result was her new business. Most of her clients came in the afternoon or early evening. It was a bit of an awkward schedule for her, but the number of clients, and their money, certainly helped to make up for that.
As part of her training, she had studied hypnotism – enough to know quite a bit about it, but certainly not enough to make her even close to being an expert. Many of the basic principles of hypnotism corresponded directly with what she did with her clients. In a way, she was partially hypnotizing all of them, but only enough to get them to relax completely.
But Chad would have to be different. She had already taken him very deep, and she knew now that she could get him to that point fairly easily again. Now she would have to go even deeper. And to minimize Mel’s presence, she had to show him other things, use other techniques. It was going to take a lot of work, and would probably take a lot of time as well. But there was no way around it. She grabbed a pad and began making notes for what she would have to do. Careful planning. Complete planning. It would be the only way.

Chad heard talking. He stopped typing and listened for a moment. It sounded like Robin was on the phone with someone. No big deal. He couldn’t really hear very well anyway. He was about to start typing again when some words came across louder and more clearly.
“But Honey, you want me to be beautiful for you, don’t you?”
He immediately wondered if she was talking to her husband about joining the gym. He gave up all pretense of work and listened harder.
“We can just have dinner a little bit later, that’s all!... Yes, I know it’s expensive, but I need this!... This is for me, for us!… So I can feel good about myself again. No, it’s important to me!...”
Her voice dropped in volume and intensity again and her words were lost. Chad looked back at the work on his computer, but his mind was on Robin. He wasn’t sure by listening if her husband had agreed or not. He hoped that he hadn’t. But knowing Robin, she would get her way no matter what.