A Nice Quiet Little Adventure

Hi All,

I know I’ve probably been remiss in not telling you what’s been going on with me, but basically, things have been mostly boring. Since my wife is away tending to her father, but my stepson is still in the house, I’ve been very limited in my “play time.”

I should tell you right now though, that things are not going well with my father in law. At this point, he is not expected to live more than another day or two. So there will probably be a few posts to the story in the next week or two that will be missed because I won’t be here.

Anyway, with that business out of the way…

Since I love diapers and high heels, I was able to indulge in my passion for both last week, every night after my stepson left for work – usually around eight PM. I usually wore four or five diapers all night long to bed, letting my body go into incontinent mode as soon as it was capable. By morning every day, I was barely telling that I had to go. In fact, I had one morning where twice, I caught myself peeing, only as I was finishing doing it! I almost missed it entirely. I know it’s just my thing, but I find that so fascinating – and fun.

I’ve also been enjoying my new boots whenever possible. I think the noise the heels on these things make might be louder than any other heels I’ve ever worn.

With that in mind, I had a bit of an adventure last night with them.

Remember last week, when I started all this? I wanted to wear my new boots into a fast food restaurant but I chickened out? Well, here’s what happened last night…

I got dressed in some normal clothes around nine PM. Okay! I was also wearing two soaking wet diapers under them and pantyhose… and of course the high heeled boots. I needed gas in my car for the week – it was near empty. So I drove out to a super busy truck stop not too far from where I live that usually has the best gas prices around. I figured that by nine PM on a Sunday night, things wouldn’t be too busy.

When I got there, I found I was right. Very often, there’s a long line of cars at all the gas pumps waiting their turn. Last night, a few of the pumps were open and I was able to pull right up to one. The first thing that frightened me, was how bright the lights were. No hiding in the shadows there. The second thing was the two vans full of high school kids that were parked just in front of the gas pump I had pulled up to. I’m not sure what the kids were doing, but they were all busy just talking or goofing around. Occasionally, one of them would walk up to where the pumps were to throw away their drinks.

Anyway, I braced myself, and got out of the car. I walked around it to the other side where the pumps were and put my credit card in. Then I started the pump running. I just stood there, watching all the kids and the other customers (quite a few) while the gas continued to run into my tank. Yes, I did worry quite a bit that someone would notice the heels on my boots. Especially when I moved. Did I mention how loud those heels are? But I pumped my gas with no visible signs that anyone noticed.

So it was time for part two!

Inside that same busy truck stop is an Arby’s restaurant. I parked my car and got out again. Now as I got out of the car, it wasn’t the kid’s I was mostly worried about, it was the woman who was sitting in her car waiting for something, or someone. She had a perfect view of me as I walked from my car up to the door and inside. I did my best to ignore her and kept going.

There were more people inside than I hoped there would be, but oh well, I was there now. I walked up to the counter (noisy heels on a tile floor) and had to wait for someone to come out to help me. As I waited, more people suddenly came in – a lot more people. I suddenly had a long line right behind me. Someone finally came to the counter and I ordered my meal. But when I was asked if I wanted it to go or for inside, I said, “to go!”

I had to wait quite a while for my meal, all the while standing up near the counter, with a long line of people right behind me. I’m afraid I never once turned around to look to see if anyone was looking at my feet. I just did my best to act tired and bored. Yes, I was tired. No, I was not bored!

Finally, my meal came! I then had to fill my drink cup which was another time consuming exercise, especially when the fountain splashed the drink all over my hand. Find the napkins. Find the lids for the cups. Find the straws. All right in front of everyone who was sitting in there eating.

I finally got everything I needed, but instead of turning to leave, I made a decision. I walked over to one of the tables and sat down! I opened my bag and sat there and ate my meal. All of it. And of course, the minute I took a sip of my drink, my bladder suddenly let loose again, sending another big amount of pee into my already soaked diapers – which really didn’t worry or bother me in the least.

By the time I was finished eating, there was another long line waiting to order food. Surprisingly, it wasn’t all the men in the line that worried me, it was the women. I would have to walk right past all of them, knowing that the heels on my feet made me walk differently and… did I mention earlier how much noise those heels make? But since I was inside and I had to get outside, there wasn’t much choice, so I just bucked up my courage and headed toward the door, stopping at the trash can along the way to throw out my trash.

So that was it. I never looked back to see if anyone was staring at me – too chicken I guess to know for sure. But at least I never heard anyone laugh or make any comments – that I could hear anyway. Will this embolden me to try something else? Who knows? I hope so. But then of course, the question is… what?

Hope everyone is staying happy. Remember to smile once in a while,
Karen

The Bet - Chapter 33 (Wednesday – week 5 Part 5 of 8)

The Bet
by Karen Singer

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

Tom Robinson walked slowly down the hallway. Since the last time he had seen Chad, he had purposely gone out of his way to avoid seeing him again. However, the rumors flying around the company about him were many and wild! Everyone was calling him “Sissy” now? Was he supposed to call him that too? Not unless Chad himself purposely requested him to do it!
This was the first project where he had requested that Chad and Robin work together. And the results, as far as he could see, were spectacular. But other things that needed to be done were backing up. Things that couldn’t be ignored anymore. Besides, from all indications, this project was almost finished. Hence, his reason for meeting with them… both of them!
Dreading seeing Chad again he braced himself more and more with each step he took.
Chad and Robin’s cubicles were just ahead. Chad’s first. He stopped just before the entrance for a brief moment, then collecting his courage, stepped into the entrance. Chad was working… at least he figured it was Chad. From the back, it looked like a woman. “Chad.”
Chad was startled by someone calling his name from right behind him. He turned quickly and was surprised to see his boss. He hadn’t seen him in quite a while now, a situation that surprised him. “Tom! How are you?”
Tom ignored Chad’s greeting and just stared at what he saw. And what he saw looked – mostly – like a woman. He had heard the rumors, but seeing him in the flesh, up close…
Chad was very much aware of the awkward silence between them as his boss continued to scrutinize him. But he remained silent. Tom would speak when he was ready.
“You look… surprising,” Tom finally got out.
Chad didn’t know whether to take that as a compliment or not. “Thanks,” he replied.
In the next cubicle over, Robin heard the voices and recognized Tom’s. She stopped working and listened intently. Tom hadn’t been down here in quite a while now. What did he want?
“I heard the rumors of course… lots of rumors… about how much more you were dressing… and acting… but, well, I haven’t been able to get down here in a while.”
Chad didn’t know how to respond. Was he about to lose his job?
“Anyway,” Tom continued, “I need to talk about a few things with you.” He looked up into the air. “Robin! I know you’re probably listening. I need to see you too.”
Robin was quick to get up and go over to see what was going on. “Hi Tom,” she said the moment she got into Chad’s cubicle.
Tom ignored her greeting too. “From everything I can tell, and from what Robin has sent me on your progress, you’re both about done with this latest thing, aren’t you?”
Chad nodded. “Yeah. Another day or two at the most.”
“That’s how I see it,” Robin agreed.
“Then as soon as you’re done, we need to get caught back up on some other things that I’ve held off on.”
“Other things?” Robin asked.
Tom turned to her. “You’ve got some updates to take care of and Chad, we need you to make some major changes to our own site. I’ll forward the specs to you later.”
Chad shrugged. “No problem. I can handle them now if you like.”
“When this thing is finished. It can wait till then.” He looked at both of them for a moment before he continued. “Since you’re about done, then I want to set up a meeting with the client and I need one of you there. I’d rather have both of you, but… well…” He turned to Chad. “No offense, but I think it would be better if you didn’t attend.”
Chad couldn’t agree more. “No offense taken. I agree completely!”
Tom was relieved that Chad felt that way. Not that it really mattered. He was the boss. His decision would stand.
“Hey,” Robin spoke up. “If Chad’s not going to be there, what if any questions come up that I can’t answer? He did a lot of work on this thing too and his areas of expertise are different than mine.”
Tom’s face creased with worry. “That’s why I’d rather have both of you there, but under the circumstances, I’d much rather have only you.”
“You could always phone me,” Chad suggested.
Robin’s face brightened a bit. “Yeah, that would work. That’s a great idea.”
Tom was relieved. “Good. I’ll try to set this meeting up for Monday then. I’ll let you know what time.” He took one more long look at Chad, studying carefully the way he looked, then nodded goodbye. “Chad… Robin…” And he walked off, relieved to have it over with.
As Tom walked back up the hallway, he mused about Chad. He definitely looked more like a woman now than ever. Obviously all the rumors he had heard were true – very true. But at least he still sounded like the old Chad. The quality of his work certainly hadn’t suffered either. Did he dare check on him and Robin more often now? Something inside of him hesitated at that. It was rather unnerving seeing Chad this way now. But he decided that he had better force himself to at least make his presence a little more known once in a while. Once in a while anyway… no need to push it too much!
Robin stared at Chad for a moment. “I hope you don’t mind not being there.”
“Are you kidding? I’m much happier staying out of sight!”
“Why? I’m sure you wouldn’t be dressing the way you are, everywhere – all the time – unless you had a bit of exhibitionist in you.”
“Let’s just say that I’m not that comfortable, or proud, of the way I look.”
Robin smiled, “Not yet, but you’re certainly getting there! Enough that you’re making me go to the gym now!”
“I’m not making you go. That’s your idea. Besides, I don’t think you need it at all.” He knew it was a vain attempt to make her give up the idea, but he tried anyway.
Robin smiled. “You’re sweet. But I do need it. I have for a long time.” She turned to walk out, then stopped. “Hey, if I’m going to phone you, then I need your number. Let me get my phone so I can program it in.”
Chad watched her run out. He was a bit jealous that she was going to get to meet with the clients and he wasn’t, but not that jealous. He would feel much better being left out – and out of sight!
Robin hurried back in with her phone in her hand. “Okay, give it to me.” Chad gave her his number. “Great,” she said as soon as she finished punching it in. “Hey, do you want mine too?”
“Sure,” he replied. “Why not.” Robin gave him her number as well and waited till he had programmed it into his phone. “Good. Back to work then. We’ve got a deadline on this thing now.”
“Back to work!” Chad agreed as she left. He stuffed his phone back into his purse, closed the drawer again, and turned back to what he had been working on. Two minutes later, he heard his phone ringing. As quickly as he could, he dug it out of his purse again. He was careful to check to see who was calling this time – Robin! “What do you want?” he asked into the phone.
He heard her giggle. “I wear girl’s panties!” she said.
“Huh? Um… Of course you do… I guess.”
“No! Is that what it says on your T-shirt?”
Chad rolled his eyes. She was still trying to guess the nonexistent slogan on his nonexistent t-shirt! “Nope,” he replied. “That’s not it.”
“Am I getting close?”
“I’m not telling!”
“Oh pooh!”
Chad was suddenly holding a disconnected phone. He put it back into his purse and closed the drawer again. Robin! Women in general for that matter!
Robin set her phone down and went back to work, but only briefly. A minute later, she reopened an internet site she had visited earlier. She had done a web search on sissy t-shirts and was amazed at how many she had found. The only thing she really knew for sure about Sissy’s t-shirt was that he considered the slogan to be embarrassing. So she had gone with the first embarrassing one she found. And some of the slogans on the shirts were truly embarrassing – for anyone, let alone a guy – or a sissy, as in Chad’s case.
Okay, her first choice hadn’t been correct, but there were still a lot of possibilities. She opened up a new spreadsheet and began copying the slogans from the website into it. She was going to get it if it was the last thing she did. And if the slogan wasn’t on this list, well, there were a lot of other sites with a lot of sissy t-shirts too.
She thought about possibly getting into his car and opening his gym bag to find out. Could she? Without a doubt, if she got the chance she would definitely try it! That way, she would know for sure. She wondered if he usually locked his car.

Chad stared at the colorful bouquet of flowers on his desk. It wasn’t looking so good anymore. The flowers were definitely dying. He pulled a few of the worst ones out and threw them away. The bouquet looked smaller, thinner. It made him feel sad in a way.
He sat back and stared at what was left of it. The flowers made his cubicle more colorful, more interesting. He thought again of the blank walls in his apartment, not colorful, not interesting. But his apartment could look great… would look great, as soon as this bet was over with – and he won of course.
He spent a few moments again thinking about the things he wanted and the way he thought it all should look. And again he realized that to make it really look good he needed some outside help. But who? And again, only Sandy’s name came to mind. But did he dare call her? She would undoubtedly tell Mel. Did it matter? And would she be willing to help in the first place? One thing was for sure, if he didn’t ask, then he’d never know.
He didn’t have Sandy’s phone number, he didn’t have Cassie’s either. But he could look up the number for the gym where Cassie worked. He was sure he could get Sandy’s number that way. He found the phone book that he rarely ever used in the bottom of one of his desk drawers and found the number for the gym. A moment later, he recognized the receptionist’s voice on the other end. “Hi,” he replied. “This is… uh… Sissy.”
“Sissy!” the receptionist’s voice squealed excitedly. “I really missed talking to you earlier today.”
“Yeah. I’m sure,” he replied sarcastically.
“Hopefully we’ll be able to have fun again tomorrow.”
Fun? Not what he really wanted. At least not the kind of fun she had in mind. “Uh… listen, will you please leave a message for Cassie to call me back. Tell her I’m looking for Sandy’s phone number. Got that?”
There was a slight pause. “Okay, I got it. You want Sandy’s number. I’ll tell her.”
“Great! Thanks.”
The minute he set his phone down, he noticed an email notification pop up on his screen. He opened it and was very surprised to see it was from Robin. The email was short. “I am a sissy gurl!” He couldn’t believe it! Now she was trying to guess the t-shirt by email! He quickly typed back, “Nope!”
His phone rang again a few minutes later. He carefully checked who was calling and saw that there was no name and the number wasn’t one he was familiar with. Hopefully, it would be Cassie. “Hello?” he answered.
“Sissy? You want Sandy’s number?”
Chad breathed a sigh of relief. It was Cassie. “Yes, please,” he replied.
“No problem. Ready?”
“Yeah.” He took down her number and thanked her. Did he dare call Sandy now? Throwing caution to the wind, he punched her number into the phone. She answered it quickly. “Hi Sandy. It’s Sissy.”
“Sissy? What do you want? I’m working right now.”
“Uh… Sorry to bother you, but I’m looking for a favor. A professional favor… and I’m willing to pay you for it.”
“You want my professional services? For what?”
“To design my apartment.”
“You mean for if you win?”
“Yeah. Exactly.”
“And you really think you’re going to win this thing?”
“I’m sure of it.”
“What does Mel say about this?”
“I haven’t mentioned it to her yet.”
There was a slight pause. “Tell you what. Before I say yes or no, I’ll talk to her and see what she says. Then if it’s alright with her, we’ll get together and discuss it. How’s that?”
“Perfect,” Chad replied.
“Okay. I got to go. We’ll talk later.”
Chad set his phone down again. Sandy would talk to Mel. He had no doubt he would hear about it from Mel later. But hopefully everything would work out just fine.

Mel ended a meeting with one of her clients and found a message asking her to call Sandy. That surprised her. What did Sandy want now? Probably another chance to babysit with Sissy. She picked up her phone and called.
“Hi Mel,” Sandy’s voice returned a moment later. “Hey, I wanted to check with you on something. Sissy called me a little while ago. He wants me to design his apartment for him for after he wins your bet!”
Mel was shocked. “You’re kidding?”
“No! He really called. He offered to pay me and everything. I just wanted to check with you first before I told him yes or no.”
Mel considered it for a moment. Was he really that sure that he could win? Or was he looking for inspiration to help him win? Either way, two could play at that game. “Okay, Sandy. Here’s what I want you to do. Go ahead and do it for him. Whatever he wants – and the sky’s the limit! But before you show him anything, I want you to do something else. Here’s what I need…”

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.

The Bet - Chapter 33 (Wednesday – week 5 Part 3 of 8)

The Bet
by Karen Singer

Chapter 33 (Wednesday – week 5 Part 3 of 8)

A little while later, Chad was back at his desk again, struggling to hold back his peeing. His efforts quickly became fruitless as he felt it starting to leak into his diapers. With a tiny grunt of relief, he just let it go. He glanced at his watch – eight minutes. Terrible! But it was still early in the day. Things always went better in the afternoons when he had less liquid in his system… and today he decided he would drink a lot less at lunchtime!
He heard Robin’s phone ring, then she talked briefly. A moment later he could hear her typing. She was busy. He opened his spreadsheet for tracking his bet progress. He stared at the row for today’s date. Thirty more days to go before the testing started. Basically, still one more month. But at least it was only one more month. Very slowly, the days were counting down. He put the cursor into the column for how long he had been able to hold back yesterday and filled in twenty-one minutes. Not very good. On Friday he had been able to hold it for an incredible twenty-nine minutes. Somehow, he had lost eight minutes from his record. But then yesterday had been a bad day. He had had way too much to drink – all day. That was a big mistake. He would watch himself more closely today. Of course, the coffee he had just finished a little while ago didn’t help things at all. He decided to have nothing this afternoon to drink at all – except of course his one required baby bottle while he was visiting Cassie.
That thought led him back to his current problem. How could he keep Robin from joining the gym? With a big sigh, he closed the spreadsheet. He had no ideas!

Gloria got out of her car in the restaurant parking lot. She saw Mel driving in and waited for her friend. They walked inside together. Two minutes later, they were sitting across from each other at a table. Neither of them said much. Both picked up a menu to glance at the contents, even though they both knew it by heart, as well as what they were going to order. The waitress was there to take their orders before either of them put down their menus. But once the menus were gone, there was no longer any excuse not to talk. They each stared at the other for a moment, wondering where to start, or who should start.
This time, Gloria jumped in first. “Look,” she said. “I really need to talk to him – alone! It’s eating me up inside that I might have done something unethical.”
“Of course you didn’t. I would never let you do something unethical!”
“Well, hypnotizing him without him knowing it sure seems unethical to me!”
“That was your idea, remember? And it was the right decision! Besides, would you rather he knew?”
“I’d rather I never did it at all!”
“This isn’t about ethical or unethical, it’s about helping out two friends who are trying to accomplish something together – something we both want! And there’s nothing unethical about it!”
“That remains to be seen.”
“You know he wants it, as much as I do. Probably more.”
Gloria shook her head. “He can’t want it more if he threw off the suggestions so fast. And he had some darn good reasons!”
“Maybe, but in the beginning he didn’t have any reasons.”
“Yeah, none that we know of at least.”
“He had none! That was why we entered into this bet in the first place – because he wanted it. And he couldn’t do it by himself. He’s too weak!”
“He’s not that weak. He threw off those suggestions by himself.”
“He is weak! And he knows it! He never did anything like this before because he doesn’t have the will-power to see it through – no matter how much he wants it. And that’s where I come in. I’m the will-power that he doesn’t have!”
Gloria shook her head. “I just don’t know! If I could just talk to him.”
“But why alone?”
“Because if you’re there, then he’ll react to your presence. I may not get a truthful answer. And I want the truth!”
“Isn’t there some way you can work around that? Convince him to tell you the truth even if I’m there?”
Gloria thought about that for a second. “I don’t know. It’s a very maybe thing. I don’t know that I can rely on it.”
Mel sat back and they both just stared at each other for a moment, each with their own separate thoughts. “I want the truth too,” Mel finally said. “But I want a different truth… well, about something different anyway.”
“What?”
Mel leaned forward. “I need to know how much progress he’s making toward holding back! You heard for yourself last week how well he was doing. I’ve got to find out if anything I’m doing now is making a difference!”
“You’re doing something different?”
Mel nodded. “Several things actually. But I really would like to know if I’m making any progress at all.”
Gloria thought about that for a few moments, saying nothing. Before she could respond, the waitress brought their coffee. They both sipped at the drinks, figuring out what to say, or argue, next.
Mel set her cup back down. “Look,” she began. “We both want him hypnotized again… we both want truthful answers out of him. Isn’t there some way we can come to an agreement on this? Some way we can both get what we want?”
Gloria thought about that. She did want answers and she knew perfectly well that Mel would never let her have him alone. She also knew that she wasn’t willing to set anymore suggestions into him that might affect his behavior one way or another. But what Mel had just said she wanted, answers – truthful answers, that wouldn’t be so bad. Not really. But was that unethical in any way? She wasn’t sure. There was still the bit about doing it without him knowing about it. But would it really be any worse than what she had already done? That was her hang-up.
But she did want answers – desperately! And she didn’t dare allow him to realize what she was doing. And if she only did what Mel was asking, just get answers, then she didn’t see any other way. She had to do it. Ethical or not, she wanted to know the truth. And that meant going along with Mel’s suggestion. Like it or not.
Mel was just sitting there watching her. She felt foolish, but it was better to be careful. “Okay,” she agreed.
Mel breathed an audible sigh of relief.
“As long as you remember, I’m not setting anymore suggestions in him. I just want to know the truth, and I guess I can find out what you want at the same time.”
“Perfect!” Mel replied happily. “That’s all I want.” It wasn’t really all she wanted. They had only reached a compromise. But it would be one that she would have to live with.

Chad glanced at the time on his computer monitor, it was lunchtime. He quickly closed all the programs he had open and pulled his purse out of the drawer.
“Hey Chad. Ready?” Robin’s voice called from the entrance to his cubicle.
“Ready for what?”
“To go to the gym, of course. Since we’re both going to the same place, I figured we might as well ride together. Then we can grab something quick to eat afterwards.”
Chad was shocked. All he could think about was Robin finding out what really went on at the gym. His worst nightmare was about to come true! “Um… You’re going now?”
“Well sure. I’ve got to sign up, don’t I?”
“Oh yeah. I guess so.”
“Then let’s go. Do you want to take your car or mine?”
She wasn’t going to back down from this. She was all too determined to go – one way or another. Why did he have to wear this stupid pink top today? That’s what started it all! “Uh… Wouldn’t it be better to take separate cars? I don’t really know how long I’ll be there.”
“Don’t worry, I’ll wait for you. I’m sure there’s going to be plenty of paperwork for me to fill out and maybe I can get another look at the place too.”
Chad well remembered the last time she had been there – at the same time he went. It was when she had found out that he was being called Sissy now. Ever since then, she had insisted on calling him Sissy too. And the name had spread rapidly around the entire company. Was there any way that he could delay going? Or maybe not go at all? Unfortunately, his diapers were really wet – again. He had to go. And he knew that Cassie had other responsibilities, she couldn’t wait for him forever. He had no choice at all. “Uh… Okay… I guess we’ll take my car then.”
“Great!”
Just thinking about needing his diapers changed caused Chad to glance briefly down at his crotch. Yes, he was sure it looked bulkier and more noticeable now than earlier. These new tighter pants weren’t hiding that very much at all. But would Robin notice when he got up? He hoped not. Getting slowly out of her chair, he prayed that she wouldn’t notice anything about his pants at all! Fortunately, the moment he started getting up, she turned toward the hallway. Chad walked next to her the entire way out to his car to minimize the chance of her seeing his pants. He had to throw his pink diaper bag from the front passenger seat into the back seat before she could get in with him. Searching desperately for a way to keep her from knowing what he really did at the gym, Chad drove out of the parking lot.
When they got there, Chad reached into the back for his diaper bag again. Robin stared at it while they were walking to the front door. “Did you have to get a gym bag like that? The darn thing looks more like a diaper bag than a gym bag.”
Chad nearly choked. “Um… It was a gift,” he lied. “Besides, I like it.”
“You would. Sissy!” She giggled as Chad reached out to open the door for her. All Chad could think was that she really had no idea! But would she know the truth soon? Probably!
The receptionist brightened excitedly the moment she saw Sissy opening the door, but then she got a bit of a shock as another woman – the same woman who had been here asking about him before – walked through the door ahead of him. “Hi…” she started to say, but the desperate look on Sissy’s face and the fact that he was trying to mouth something silently to her stopped her from saying anything else.
“Hi,” Robin returned politely, thinking the receptionist had been talking to her in the first place. “Remember me?”
The receptionist glanced back at Sissy. He was still desperately mouthing something at her. “Sure, I remember you,” she said to Robin. “Are you going to sign up this time?”
“That’s why I’m here.”
“Fantastic!” the receptionist replied happily as she glanced back at Sissy one more time. This time she understood what he was mouthing – “Get Cassie!” She nodded toward him that she understood. She grabbed a thick stack of forms that has been put together already and handed them to Robin. If you want to get started on these, I need to see if I can find someone. I’ll be right back. With another nod toward Sissy, she left quickly to find Cassie.
“Geez!” Robin said as she looked through the stack of forms. “I expected a lot of paperwork to fill out, but not this much.” She picked up a pen from a cup on the counter and started working.
Chad felt relieved. So far, so good. But he knew it couldn’t last. At least the receptionist hadn’t asked for another curtsey today… or to see his diapers either. But with Robin going to the gym with him now, how long could that last?

“She’s with him?” Cassie asked the receptionist, not believing she heard right.
“She’s filling out the forms right now.”
“Wow! And how is Sissy acting?”
The receptionist shrugged. “Scared. Nervous. But I don’t know why he should. I mean, the cat’s totally out of the bag now, isn’t it?”
Cassie thought about that for a moment. “Maybe not so out of the bag as you think!”
Cassie led the way back up to the front of the gym. The moment she spied Sissy, she could see how worried she looked. Obviously, he hadn’t planned on his friend being here with him. But his friend was another customer, and customer’s had to come first! “Welcome back,” she said to Robin, totally ignoring Sissy. “Remember me?”
“Sure,” Robin replied. “Cassie, right? You showed me around last time.”
“Right and you’re…”
“Robin,” Robin reminded her.
“Of course! Forgive me for not remembering.”
“No problem.”
Cassie glanced again at Sissy. He looked a bit desperate. “Do you have any questions?” She asked Robin.
“Not now, but before I leave, is there any chance I can get another tour and maybe talk about what I think I’d like?”
“Definitely. Tell you what, I need to get Sissy here… uh…” She wasn’t sure how much Robin knew about him. What could she say? “Started,” she finally finished. She glanced back at Chad as he rolled his eyes. “Then I’ll be back and we’ll start from the top. Okay?”
“Perfect,” Robin replied. She turned toward Chad who had been happy to stay somewhat unnoticed. “See you later.”
“Uh… See you later,” he replied as he followed Cassie toward the back. How awkward!
As Chad followed Cassie, Robin glanced up from the paperwork to watch them before they turned out of sight. Something about Chad caught her attention. Something about his bottom looked different. Did it look bigger? Then he was gone. No, it had to be a trick of the shadows. She had only imagined it. She bent back down to filling out the forms.
“Hi Sissy,” someone in the gym called out to him as he walked through. Chad turned. A woman on one of the machines was waving to him. He waved back. Would the customers here ever forget what he had done on Monday? Probably not. A minute later, Cassie was closing the door to the little office behind them.
“What’s going on?” she asked.
“She insists on signing up!” Chad replied. “Is there some way you can stop her?”
“Stop her? You’ve got to be kidding. She’s a customer now. And customers always come first – unlike you! Besides, we need some new ones, and she looks like a prime candidate.”
“But she’ll find out what I did. Worse, she’ll find out what we’re doing here!”
“You mean she doesn’t know?”
“No! And I’d like to keep it that way.”
“Cassie shook her head. “I don’t think there’s anything I can do for you. Everyone’s still talking about you. She’ll probably find out sooner or later.”
“I don’t want her to find out at all! Isn’t there anything you can do?”
“Sorry. Besides, it’s not really my problem… it’s yours! You might try telling her the truth – yourself – before she finds out from someone else.”
Chad shuddered at the thought. “I can’t! I don’t want her to know at all.”
“Like I said, sorry. Okay, are you going to get undressed or what? I’m afraid we’ll have to skip the fun part for you today so I can take your friend on another tour.”
Chad reluctantly began undressing. As soon as he was down to just his diapers, he laid down on the floor. Cassie handed him a baby bottle to start on while she removed his diapers. Her actions were faster and less personal than usual. A fact not lost to Chad. Before he realized it, she was pushing up on his legs and sticking another of the stupid suppositories up inside of him again. He hated it! More so because she wasn’t playing with him at all this time. Quickly, she fastened two more diapers onto him and before he knew it, she was done and standing up. He felt like he had lost something.
“Okay, she said. I’ve got to go take care of your friend while you finish that bottle. Maybe you better stay here till I come back. Besides, Mel asked me to make sure you get a bottle every day so I can check it for her before you leave.
She was out the door and gone before Chad could do anything else. He just laid there and sucked on his bottle – while he fretted about Robin joining the gym. What was he going to do?
It was a long time before Cassie finally came back. Chad had plenty of time to finish his bottle and get dressed again. “All ready?” Cassie asked as soon as the door was closed.
“Yes. What did Robin say?”
“About you? Nothing. We just walked around again and talked about what she wants. You’re in luck there by the way, she wants to come a few nights a week right after work and is very interested in one of the exercise classes we have.”
“So she’s not going to be coming here at lunchtime?”
“Not unless she wants to. Once she joins, she can come anytime she wants.”
“You mean she hasn’t joined yet?”
“Not officially. She hasn’t paid for anything yet because she hasn’t decided what plan to go for yet. But trust me, she’s joining!”
That was mostly good news for Chad. Maybe he could still convince her not to join. He was struck by another thought. “Maybe if she only comes in the evenings she won’t run into anyone who was here on Monday.”
“Don’t bet on it. There’s a few of those women who come to the later classes too. Sometimes they come early in the day, sometimes they come later.”
Chad was not happy at all to hear that.

The Bet - Chapter 33 (Wednesday – week 5 Part 2 of 8)

The Bet
by Karen Singer

Chapter 33 (Wednesday – week 5 Part 2 of 8)

“Hi Sissy,” Robin’s voice called as she walked past the entrance to his cubicle. He turned to return her greeting because she had paused briefly at his cubicle, but by the time he turned around, she was moving away again. He turned back to watch his computer booting up.
“I’m back,” Robin said to his back a minute later.
Chad turned around, surprised to see her so soon again. “Morning,” he finally got to return.
“Pants today,” she noticed right away. He nodded happily. “And new ones,” she noted. He nodded again. “Well…”
Chad was confused. “Well what?”
“Well, stand up so I can see. That’s what!”
“Oh.” He felt like he was being inspected all over again. But as he got up out of his chair so Robin could see what he was wearing better, it struck him that her little “critiques” of his outfits every morning had also become the “usual.” Typical.
Robin’s face went from happy to frustrated… or was it angry. She rolled her eyes. “Humph!” A moment later, she stomped off to her own cubicle.
“What?” he called after her. But the entrance to his cubicle was empty. He glanced down at what he could see of his outfit. It all looked okay to him – as far as he could tell.
Earlier this morning, Mel hadn’t said that anything was wrong. Nothing! So what was eating Robin? He walked out of his cubicle and went into hers. Her back was to him as she sat, slumped over, watching her monitor as her computer booted up. “What’s wrong?” he asked. “I thought this looked fine.”
She didn’t turn toward him at all. She just waved a hand in the air. “Oh, it is fine. Perfectly fine! You look great!”
Chad was confused even more. “So what’s wrong then?”
“Nothing! There’s nothing wrong with you at all!” She half turned toward him. “With the way you look, anyway.” She turned away again and typed her password into the machine.
“So what did I do to piss you off?”
“You? You didn’t… Ugh! Just leave me alone!”
Shaking his head, Chad backed out and went back to his own desk. “What had gotten into her? She had seemed so happy one second then the next, she was upset. Women! He’d never understand them – even though he was dressing like one all the time now. He logged into his own computer and pulled up the things he was working on. Women!
“Sissy?” Robins voice called over the cubicle wall.
“Yes?”
“I’m sorry. Okay?”
That surprised him. “Sure. No problem.” He still didn’t understand what was going on.
“Look, it’s just that…” He heard her mutter a soft curse word. A moment later she was walking into his cubicle. He turned to look at her. She seemed a bit upset. “Look,” she said again. “I’m a woman, and you’re not. You’re only pretending to be… no offense!”
“None taken,” Chad replied, wondering where she was going with this.
“Well, you’ve only been dressing like a woman for a short while now but…” she stopped, trying to find the right words.
“But?” he prompted.
“But… Damn it! Did you have to wear a top like that?”
His top? He briefly looked down at it. It seemed okay to him. “What’s wrong with it?”
“What’s wrong?” She threw her arm up in the air, totally exasperated. “What’s wrong?” she repeated. “Shit! Look at you. You’re not a woman, and I am!”
“So?”
“So your shape looks a whole lot better in that top than mine ever does – in anything!”
His shape?
“I mean… Look at you! All nice and slender and well, curvy in all the right directions. While I’m just… dumpy!
“You’re not…”
“Oh shut up!”
Chad shut his mouth. He had been married before. He had been around women enough to know when to just let them rant.
“It’s not fair! I don’t eat that much. And I diet… whenever I can. A lot actually. I used to look like you, in fact, better! But since I got married… And then after the baby… And then you come along and suddenly change your whole… “outlook” on life. And within a month you go from looking like a guy to much more like a woman. And you’ve lost weight. A lot of weight! Do you know how hard that is for me to do?”
Chad knew when not to answer. He just let her rave on.
“Very hard! But you make it look so easy! And the results! Okay, I know a lot of what you’ve got there is fake, but still, it’s not fair that you should look better in a blouse like that than I do! Damn it!” She pointed her finger at him. “I’m going with you today to that gym, and this time, I’m going to sign up!”
Chad immediately realized the implications of that. “No!” But she was already stomping out. He got up and followed her. She was sitting at her desk with her head in her hands. “Robin, you don’t want to go to that gym.”
“I need it. Obviously, I need it,” she said into her hands.
“No you don’t. You look great!”
“Get lost!” she said, none too kindly, still not looking at him.
“But…”
“Just get out of here!”
Chad backed away and went back to his own desk. His shape? Would she really sign up to go to the gym? That gym? The very thought of it worried him tremendously. If she did… and even if she didn’t go at lunch time with him… then undoubtedly, she would still hear about what he had done there on Monday within a very short time. Everybody there was still talking about him. As Cassie had said, he was “all the buzz.”
He stopped his thinking short. And what if she went there today… at the same time he went? A sick feeling ran though him. The receptionist! The damn receptionist. She had tried yanking his chain a little bit yesterday. If Robin was there and she tried it… He stared at his computer, but he was unable to work for worry about what Robin might do.

Gloria unlocked her office building and went inside. She went directly into her office where she set her purse on her desk and sat wearily down in her chair. Her mind was on Mel though. Actually, Mel and Chad. She had no doubt that Mel would call her again to set up another lunch date and try to persuade her yet again to hypnotize Chad and help her to win their crazy bet. But that was the one thing she would never do.
Yes, she did still want to hypnotize him again, but only to get answers. How badly had she screwed up by setting those instructions in his mind in the first place? It had all seemed like such fun. She had honestly believed that he really did want everything she had done to him. And that was her problem! Almost everything had worked – brilliantly. Better than she ever hoped they would. So somewhere in there, he had to really want what she had done to him. So she felt totally good with everything she had done.
But then she had found out how hard he was fighting the most important part of it all – for Mel anyway. His incontinence! The suggestions seemed to have stuck, but only for a short while. That was common for hypnosis suggestions. If you didn’t maintain them then they eventually wore off. But there were other things… he had reasons why he was fighting it so hard. Darn good reasons too, as she saw it. Although what was really important was that they were good reasons to Chad. They were strong enough reasons that they allowed him to quickly break the hypnotic conditioning.
So he did want what she had done to him… but now he didn’t want it. Which left her confused and feeling guilty. If he didn’t really want it, it wasn’t ethical. Of course since they had done it all without his knowledge, it wasn’t ethical anyway… but she could look past that on the pretense that he really had wanted it in the first place. Wasn’t that the reason behind their bet anyway? That he did want it?
Ugh! She was going around in mental knots! How could she get Chad alone for a while to hypnotize him and really talk to him? There had to be a way!

Mel stared at the back wall of her office, not really seeing it. Her thoughts weren’t on work, they were on Gloria, and how could she get Gloria’s help with Chad again. She only knew a little bit about hypnotism, but she was very certain that it would be easy for Gloria to hypnotize him again and reconvince him that he really did want to be incontinent – and she knew for a fact that he did. Why was he fighting against it so hard now? Okay, so he had some reasons. But in the beginning, he had no reasons at all. The result was that she and Chad were firmly locked into a battle of wills. And time was growing shorter!
She wasn’t even sure if she had made any progress with him anymore. She had thought she had. But after hearing how long he was capable of holding back, she wasn’t sure of anything anymore. Gloria could get the answers out of him. Truthful answers. She could do so much to help, but she wouldn’t. There had to be a way!
And the first step in getting Gloria’s help again was to keep talking to her. Their lunch yesterday had been better, but strained. She had to keep talking, keep trying! And to do that, meant more lunches. Every day for the rest of this bet if that’s what it would take.
She picked up her phone and punched in Gloria’s number. “Hi Gloria. It’s me.”
“Hey Mel. How are you?”
“Fine. Lunch again?”
Gloria sighed. She had known Mel would ask. “You know I’m not going to change my mind.”
“I know. But we’ve still got to talk.”
Gloria paused for a moment, thinking about it. If only she could convince Mel to let her have him alone for a while! “Okay Mel. The usual?”
“Yeah, that’s fine. See you later?”
“Later.”

Chad was working, getting things accomplished. What he was doing at the moment was repetitive and simple, but necessary. The redundancy of the job was beginning to wear at him, but he was almost done with it. He was surprised though when his concentration was broken by Robin walking into his cubicle and leaning up against his desk. He turned in his seat to look at her. She didn’t exactly look happy, but at least she didn’t seem to be mad at him anymore. He just raised his eyebrow quizzically.
“Sorry,” she apologized sheepishly.
He shrugged. “For what?” and then he grinned, letting her know that everything was alright. He was pleased to see her smile.
“Ready to go to break?” she asked.
Chad remembered the doughnut from yesterday. He suddenly wanted to go very much, but he was almost done with what he was working on. “I just need a minute,” he said as he turned back to his keyboard.
Robin stayed where she was and watched him working. She noticed something as he worked, something she had noticed before. Something about his hands. “You know, ever since you got those long nails last week, you’ve been moving your hands much more like a woman.”
He turned his head and looked up at her, then went back to his task.
“Not that that’s a bad thing. I mean, I think it’s really good in fact… seeing as how you dress all the time now.” She watched him for a few more moments. “And now that your nails are shorter, but still pretty long, I think you move them even more femininely.”
Chad stopped what he was doing and stared at one of his hands. He stretched the fingers out then curled them up, then stretched them out again. He still thought his fingers looked much more feminine with these nails… and it still pleased him. “Thanks,” he said… “I think.” She laughed a bit. Chad quickly finished up and with a flourish, minimized the project on his desktop. He got out of his seat. “Do you think they’ll have anymore of those doughnuts?” he asked as they both headed out into the hall.
“I sure hope so,” she replied. “You know. Your outfit really does look nice today. I’m sorry I got all huffy earlier. I just couldn’t help it.”
“Thanks,” Chad replied. “And for the record, I don’t think you need to be worried about going to the gym. Not at all.” The last thing he wanted was for Robin to be going to the gym with him. She would find out way too much!
“No, I think I do need it. Desperately! It’s about time I got off my bottom and made more of an effort to lose some weight.”
“But the gym? That gym?” How could he convince her not to go?
“What’s wrong with that gym? It’s a ladies gym and it’s supposed to be a good one. Besides, you go there!”
Chad had no answer for her. The last thing he wanted was for Robin to go to the gym where he got changed every day. The worry was still foremost on his mind as he entered the break room. He spotted the doughnuts again right away, but this time he followed Robin through the coffee line first before they each grabbed one of the pastries. Then together they made their way back toward the table the women usually favored. There were still some empty seats, but the table was filling up rapidly. Chad devoured his doughnut quickly. Yum! Solid food! Nothing like it! He began thinking about lunch. What would be good? Maybe a steak?
“Hey Sissy,” one of the women interrupted his thoughts of food. He looked up as he took a tiny sip from his coffee. “Love your top today. It really shows off your necklace nicely.”
“Thanks,” Chad replied. “I thought the same thing when I put it on this morning.”
“That reminds me,” another one interrupted. “Why do you always wear the same old necklace every day? You’ve always got new clothes on. In fact, I don’t think I’ve seen you wearing the same thing twice.”
“You haven’t!” Robin agreed. “He never wears the same thing twice, not that I’ve noticed either. And I get a good look at what he wears every day.”
“So how come you never wear any other jewelry?” the first woman asked.
“And how come no earrings yet?” Still another woman added. “I’ve been suggesting them to you for weeks now.”
Chad had no answers for them – that he could tell them. He always bought just what Mel ordered him to and that was it. In fact, that was enough! “Uh…” he searched for a decent answer. “Uh… I guess I’ve just spent so much time looking at clothes that I haven’t really gotten around to the jewelry yet.”
“But you are planning on getting some new jewelry then?” the first woman asked.
“Uh… Probably,” Chad replied.
“Good,” another woman said. “I can’t wait to see what you get. Your clothes are all really nice. I’m betting you have the same taste in jewelry.” There seemed to be a complete agreement among all the woman about that.
Chad inwardly gulped. Had he just agreed to shop for a bunch of new jewelry – nice stuff? Nice meaning probably expensive? He didn’t think he had promised to buy any, but maybe he did.
“So are you trying to be another one of those women who never wears the same thing twice?” someone else asked.
Chad was taken by surprise by the question. “No. Of course not.”
“Then how come you never wear the same thing again?”
He shrugged while he tried to think up a decent answer for that. “I guess just because I’ve been buying a lot of new clothes and I just wanted to try them out.”
“A lot of new clothes. That’s for sure!” someone added. “I wish I could afford it.”
“You and me both!” Robin replied. Again, there was a lot of agreement among them all. “You know,” Robin added, “if I join that gym, then maybe I’ll have an excuse to get a bunch of new cloths too.”
“You thinking about it?” someone asked her.
“Yes. Seriously! I mean, have you seen the way he looks? It’s starting to get embarrassing for us real women! At least as far as his shape goes.”
Chad didn’t know whether to be embarrassed or proud.

Playing Again

I’m sitting here this morning, wearing four very wet diapers. The bulk between my legs, up my front, and up my backside is huge. My legs won’t even begin to come any closer together than a very wide legged spread.

My wife left in the wee hours of the morning yesterday for her little trip. I had bought some pantyhose to wear to work yesterday, and let me tell you, I really enjoyed that. When I’m at work, I mostly sit behind a desk and hardly move at all. But the few times I walked from one building to another I was able to really enjoy the feel of the hose under my pants.

On the way home after work, I finally bought myself some diapers that I put on (two) as soon as I got home. Later, I went out shopping to Wal-Mart, looking for a few things. Would you believe that I didn’t see even one skirt in the store – in any size or type! Not one! And I looked at their shoes – nothing! Pitiful! Anyway, I’m heading out shopping again early this morning to try somewhere else.

But I did enjoy wearing my diapers all last night. Since I hadn’t wet them much before bedtime, I left on the two that I had and added two more to get me through the night. Then, all night long, I managed to keep my muscles down there totally open and relaxed – allowing nothing to give the least bit of hindrance to my peeing.

Things didn’t really kick in though till about two AM. That’s when I let loose with a fairly good pee. It was all I could do to not tense up in any way. All night long, the few times I noticed my body trying to tense those muscles even the slightest bit, I admonished myself and instantly relaxed. I’m happy to say that my body responded and stopped tensing up even the slightest, so my muscles down there are still wide open even now. The result was that I kept wetting and wetting and wetting. Mostly in very small amounts, but as morning grew closer, I noticed a few of them were getting to be bigger and bigger amounts. A few times during the night, I felt the pressure suddenly build, then I felt nothing more, and other times I never noticed anything except that I was suddenly peeing a little bit.

I’m afraid that since I spent the last few hours lying on my stomach, I leaked out over the top of my waistband in the front and left two small wet spots on the sheets. It’s a good thing I remembered to put some plastic under the sheet. I’ll have to wash it later.

A few times, mostly toward morning, I was also wondering if I wasn’t going to be doing something else in my diaper too. Quite a few times, I let loose with a lot of tiny gas bubbles. But nothing else came out. I may very well be messy though before I get changed this morning.

I really hope my shopping goes well this morning – and quick. I’m so looking forward to relaxing as a big sissy all day!

Stay happy everyone,
Karen

The Bet - Chapter 33 (Wednesday – week 5 Part 1 of 8)

A quick note – My wife left for a short trip to Louisiana in the middle of the night so I’m going to have a few days to play again. On the way home from work yesterday I made a quick stop and bought some pantyhose that I’ll be wearing to work today. After work I’m planning on stopping to buy diapers again (one of my passions) and then later tonight I’ll probably be shopping for a pair of heels to wear this weekend. I wonder what else I’ll think up to do.

So I’ll probably be blogging daily for the next few days.

Karen


The Bet
by Karen Singer

Chapter 33 (Wednesday – week 5 Part 1 of 8)

Her dreams were short and sweet, each one lasting only a few minutes. None of them seemingly related to each other. She dreamed of work, then nothing. She dreamed of love, then nothing. She dreamed of Sissy, then nothing. She dreamed of shopping, then nothing. She dreamed of the home she would someday have… with Sissy there to take care of it, then nothing. And again she dreamed of Sissy.
Each dream was different. None of them related. But as the night wore on, more and more of her dreams included Sissy… or Chad. Or Chad-Sissy.
Her dreams of Sissy gradually grew more disturbing as her conscious mind began injecting doubts and worries. Again and again she rolled over, throwing away the dream in favor of a new one. A better one. But the dreams kept coming. Some good, some not so good.
The dreams of Sissy and the worries and doubts began returning, again and again. Her troubled feelings mounting with each succeeding dream. Worry, worry, worry! Upon worry, worry, worry! Till at last she rolled over one more time and glanced at her clock.
With a groan, she forced her legs over the side of the bed and sat up. She brushed her long hair back off her face with both hands and pulled on it from the back for a moment, trying to clear her sleepy mind. With a sigh, she brought her hands back down to her lap and just sat. It was morning. Her alarm would be going off in a few minutes. She reached out and switched it off.
Her mind seemed still fogged with sleep as she made her way to the kitchen to start the coffee brewing. She stared still half asleep at the coffee maker for a few moments before she found the brain-power to fill it with grounds and turn it on. But as she stood there, watching the coffee brew, her mind slowly began to regain its function. The smell of the freshly brewed coffee began to wake her up, bring her back to life. Her thoughts turned finally to the day ahead… and then to Sissy.
Sissy! He would be up by now, probably long up! At least he better be up! She had set his alarm again last night while he was sleeping so he had no reason not to be up! She was always amazed at how soundly he slept every night. She wished she could do the same. She saw the coffee finish and she poured herself a cup. Mmmm! Wonderful. She carried it into her living room and curled up in her favorite chair. She had worked late last night on her laptop. Work got that way once in a while. It was just something she had accepted long before as part of the job.
While she had worked, she had made Sissy stand in his corner. The thought of it amused her. She had made him stand there, unmoving, for a very long time, and he had managed it just fine. It amazed her how much power over him she held now. Yes, he still rebelled – a bit – but overall, she was firmly in control. It still surprised her how much pleasure she received from having him so firmly in her grasp – and making him do the most outrageous things – and denying him the ability to be… a man!
And speaking of Sissy… She glanced at her clock. It wouldn’t be too long before he was due here again. She quickly finished the rest of her coffee and got up from her seat. It was time to throw some clothes on and make his breakfast. A baby-food breakfast! She giggled to herself at the thought.

Chad stared at his face in the bathroom mirror. His makeup job was… acceptable. He toyed with the idea of creating a different look for himself, something different. Women did it all the time. But he quickly discarded the idea. It had taken him forever to learn how to do just what he did now, not to mention that he didn’t have a clue as to how to do anything else with his makeup. And besides, his look was… acceptable.
His makeup was now done. He had already done his hair. He was already wearing his two diapers for the morning, along with plastic panties, a waist cincher, his overly tight and small all-in-one girdle, and his pantyhose. He hurried out to the kitchen where he grabbed his third and final baby bottle for the morning, this one, luckily, filled with apple juice. He started drinking it as he walked back toward his closet to decide what to wear.
He opened his closet door and glanced around. The only clothes in it were women’s clothes. Mel had long ago removed every masculine item he had in his apartment and put them… somewhere. His eyes quickly fell on the two new pairs of slacks that he owned. A hint of a smile crept onto his face. He hadn’t been able to wear slacks in… days! He grabbed a pair and pulled them off of the hanger. Now, what top to go with them? His eyes fell on a pink short-sleeved top that was fairly stretchy. It would fit a bit tight, but it was made to do that. And after wearing his colorful dress to work yesterday, the pink top actually seemed tame. He pulled it down too.
The pants fit tighter around his hips than the previous pairs that he had owned – much tighter. But he didn’t think they were too bad. Heck, the women in the break room had all said that he needed better fitting pants, and from everything he could see, these did fit a lot better. He stared at the front crotch. He couldn’t tell from looking at it that he was wearing diapers underneath it all, but… well… he wasn’t really sure, but he didn’t think it looked totally feminine either. Of course though, with two diapers and the chastity device crushed under his girdle, he supposed it couldn’t be perfect. He just hoped that his diapers wouldn’t become too visible later, when they were wetter, or worse.
He pulled the stretchy top on over his head and pulled it down over his fake breasts and pulled it into place. The bottom of it ended just over the top of his slacks. He looked at himself in the mirror. The first thing that he noticed was how well the pink color and v-neck of the top showed off the pink stone in the necklace he was wearing. He fingered the necklace for a moment and his eyes were drawn to the pink stone in his ring. Seeing them made him feel funny, both embarrassed and excited at the same time. He put his hand down and kept staring at his reflection. The tight top, over top of his waist cincher and girdle accentuated his “new” more feminine figure – quite a bit. That made him feel funny too, for the same reasons. He stared again at his necklace. There was a bit of a decoration on the top, right at the “V” that bunched up the material, adding visual interest to the top. The decoration did nothing to distract from his necklace though and seemed to accentuate his “boobs.” That made him feel funny too. Oh well. He had worn worse. Much worse. In fact, this was fairly tame. Comfortable too. Almost casual.

Feeling better, he slipped into a pair of three inch heels that were high enough to keep the bottoms of the pants from dragging on the ground. He checked his image one more time – acceptable – maybe even pretty good. Putting the baby bottle to his lips, he quickly finished off the last of it. He was ready. It was time to grab his purse and diaper bag and go. Mel would be waiting for him… Mel, and probably her idea of breakfast for him – baby food! Ugh!

Mel smiled as she heard the knock at her door. He quickly stirred the baby cereal in the pot one more time, then turned the stove off. It was ready. She hurried to open her front door. The wonderful sight of Sissy in a clingy pink top greeted her.
“Good morning, Mistress,” Chad said as he dipped a quick curtsey.
“Good morning, Sissy,” she replied as she stepped back out of the way to let him in.
He set his purse and diaper bag on the floor by her table and turned for her usual morning inspection. He handed her the bag of empty baby bottles which she didn’t even bother to check. Again. He wondered if he could get away with not drinking some of them, but decided he’d better not try it. Whenever she did open the bags, she would know for sure!
Mel looked him over carefully, very pleased with what she saw. She reached out and pulled on his necklace a bit. “That looks really nice with this top,” she remarked.
“I thought so too.”
She walked around him, studying his figure. “Those pants do fit better. A lot better.”
Chad was tempted to tell her that he was worried that they might show his diapers later, but he held his silence. Two minutes later, he was sitting in his highchair, bib tied around his neck, staring at the bowl of pasty colored baby cereal she had just put in front of him. Yummy – Not! He picked up the tiny rubber coated baby spoon she had set next to the bowl and began trying to shove it into his mouth. The stuff tasted awful, even though he was well used to it now. His problem was that it still kept falling off of the tiny spoon with every bite he tried to take. It took forever to eat it all.
Mel poured herself another cup of coffee and leaned back against the counter to watch him trying to eat. It never seemed to get old, watching him struggle like an infant. It seemed like the harder he tried, the more he failed. Sometimes she wanted to laugh out loud – occasionally, she did. Over and over again, she watched as he picked up his baby bottle between spoonfuls of cereal to wash it down. She had tasted the cereal many times herself while she cooked it. She didn’t think it tasted quite as bad as he claimed it was, but then she only took the tiniest of bites each time. Just enough to check the flavor. But then, it didn’t really have much flavor. None of the varieties she had did.
Denied masculinity. Denied the ability to be and adult… well, she was sort of working on that last part she supposed. But then there were so many ways and reasons she would never be able to take it all away from him. But still, the thought of it aroused her more than just a bit. Denying him everything he used to be, everything he probably ever thought he would be in the future. Remolding him into her own little plaything. Of course, all too many of those directions she was pushing him came from his own wantings, his own fantasies. Way too many. But still, she was surprised at how many of them she was really enjoying. And she knew without a doubt that the forced reality of the situation for him was far more horrible and embarrassing than his fantasies had ever led him to believe they would be. So she felt very satisfied in what she was doing to him. Very satisfied!

Just a typical morning. That’s what was mostly on Chad’s mind as he drove to work. He looked down and saw his pants covered legs. It had been a while since he had been able to wear slacks. They felt, and looked, strange to him now, yet he was oddly proud and relieved to be wearing them again.
Just another normal day… his “new” normal day. His life had been turned upside down and been twisted around in knots like he never knew existed since this bet had started. And “normal” lately didn’t seem to last very long. Just off the top of his head he realized that Mel had increased his nighttime bottles, his morning bottles, and he now only had two pairs of pants that he could wear. Only two days a week now that he could go without wearing skirts – to work anyway. Once he got home, the most likely scenario would be for Mel to have him change out of his pants into… something else.
Yet the day did feel normal to him. And for once, he was glad. In his new world, where things changed all too often, “normal” or “usual” were reasons to celebrate. A short while later, he was still feeling pretty good about things as he fired up his computer and stowed his purse in his desk drawer.