Friday, November 27, 2009

The Bet - Chapter 13 (Thursday – week 2 Part 3)

The Bet
by Karen Singer

Chapter 13 (Thursday – week 2 Part 3)

Just before lunch, Robin stopped at Chad’s desk. “I’m going out for a burger, want to come?”
“No thanks, I can’t,” he replied.
“Why not? Got another heavy date?” Chad thought for a minute. “Something like that.”
“You’ve got a lunch date? Good for you.”
“No, not really.”
“But you just said you had one.”
“No… well yes I did, but… It’s complicated.”
“So explain it to me.”
Chad sighed. “No. I don’t want to talk about it.”
“Ok,” Robin replied. “See you later.” She had tried and he had clammed up again. But now she was really curious. She went down to her car and waited.
She had to wait about five minutes before Chad finally came hurrying out of the building and then got into his car. As she saw him walking, she noticed that he was walking a bit more awkwardly than he had been this morning. A little bit straddle legged maybe? Probably not, she decided.
When his car pulled out of the parking lot, she followed. Again, he drove directly to the gym and she pulled into the driveway past it. As before, he got out of the car carrying not only his purse, but the big pink bag as well. Robin drove off to get some lunch. Obviously, Chad was going to the gym almost every day. One thing was for sure, she admired his determination. Exercising everyday was not her idea of fun.

“Hi Sissy,” the receptionist said teasingly, and all too loudly.
“Uh, Hi,” Chad replied, embarrassed that she had called him Sissy. “Is…”
“I’m going. Just be patient.”
Chad waited while the receptionist went back to find Cassie. He was glad that this time she and Cassie came back a lot faster.
Cassie stopped about ten feet from where Chad was standing. “Hi Sissy,” she said. Again Chad felt embarrassed by the name. He started to walk towards her, but she held up her hand, stopping him. “Aren’t you going to say hi to me?” she asked, as if she were hurt.
“Uh… Hi Cassie,” he replied.
“Oh come on! You can do better than that! I want you to do it like you did last night.”
Chad looked around. He couldn’t curtsey to her here. “Cassie please… not here!”
“I’ll tell Mel.”
Chad suddenly wanted to scream. He had no doubt that Mel would be mad at him if he didn’t do as Cassie said. Since he had his purse in one hand and was holding on to his diaper bag in the other hand, he just dipped down in a quick curtsey as he said, “Hi Cassie,” one more time.
The receptionist went into fits of laughter and Chad’s embarrassment skyrocketed. “Much better,” Cassie said as she turned and led him through the room full of exercising women.
As soon as Chad got back to the now familiar room and Cassie had closed the blinds on the door, he began to get undressed. Cassie watched him closely as he did it. As soon as he had gotten his girdle pulled half-way down however, Cassie immediately noticed a bit of a smell that hadn’t been there before. “Are you finally messy?” she asked as he pulled the girdle off completely.
“Very,” he replied. “Since I left for work this morning.”
Cassie just nodded and waited till he had removed his plastic panties too. Then she told him to lay down on the floor as usual. She opened his diaper bag and gave him his bottle to start on first. Then she began unpeeling his diapers. “Pew! Wow, you’re a real mess!”
“It’s the girdle,” Chad replied pulling the nipple out of his mouth. “It makes it hard to go and then the mess just slides around wherever it can.”
“I can see that,” Cassie said as she pulled out the box of baby wipes and another plastic bag from his diaper bag to put them in. It took a few minutes and plenty of wipes, but eventually, she had him completely clean. Chad wasn’t quite finished with his bottle yet. She looked closely at his cock restraint, and especially at his flaccid penis inside it. She could see some red marks up around where the little teeth had dug into him. Has somebody been naughty and been trying to get hard?” she asked. He didn’t answer. She didn’t expect him to.
With an evil grin on her face, she grabbed his cock restraint lightly and gently rocked it back and forth, trying to get a response. But the only response to that motion was the sudden look of worry on Chad’s face. She pulled on it and saw Chad’s face register a little bit of pain. She suddenly felt frustrated. How was she going to try to stimulate him if she couldn’t touch or even pull on the damn thing?
She reached under and cupped his exposed balls, massaging him gently. The look of worry on Chad’s face suddenly increased. “Please don’t,” he suddenly said. The worry in his voice was very evident.
“Just drink your bottle like a good baby,” she replied as she kept working on him. But it was plain that he was trying desperately to control himself. She could see the little teeth inside the device digging in deeper now as his cock had grown a tiny bit, but mostly it was still staying soft inside the thing.
“Please,” Chad begged again.
“Let me guess,” she said. “I’m betting you want this really bad. Don’t you?”
“Yes!” he replied. “But I can’t. It hurts! It hurts a lot!”
Wickedly, Cassie kept at it. The look of pain was now evident on Chad’s face. He couldn’t drink his bottle anymore and wasn’t even trying. Despite the teeth digging in to him, his cock inside the device was growing, filling the inside of the restraint more and more. Then almost completely. Chad was now thrashing around under her and she was having more and more trouble keeping at it.
Chad couldn’t take the pain anymore. He roughly pushed Cassie’s hands away and curled up on his side, both hands wrapped protectively around his plastic covered privates.
Cassie backed off. “You seem to have a long way to go in learning to control yourself. But I guess you’ve just started so I can’t expect much more than that.”
Chad didn’t say anything, he just rocked himself on the floor till the pain subsided enough. Cassie helped him roll onto his back again. She slid two fresh diapers under him and coated him wherever she could with the baby lotion. Then she taped him up again. A few minutes later he was completely dressed again.
“Feeling better now?” Cassie asked.
He nodded. “Yeah, the pain has gone down a lot.”
“You know, Mel asked me to do that.”
Chad groaned but didn’t say anything.
Cassie led him out to the front, but before he could get out the door, she stopped him. “Chad! Aren’t you going to thank me?”
Chad turned around aghast. He wanted to run out of there. The receptionist was watching all too closely again, anticipating it. He quickly curtseyed and said “Thank you, Cassie.” Then he all but ran for his car as he heard the peals of laughter from both the receptionist and Cassie behind him.

Robin was standing just inside the door of the building after lunch, talking with a couple of other women. Out of the corner of her eye, she noticed Chad hurrying back from his lunch. As he came through the door, she watched him closely. No, it had just been her imagination. There was nothing wrong with his walk at all. The other women with her were staring at him too, watching him hurrying back to his desk. “And you said he went to the gym again?” one of them asked.
“Yeah. Just like yesterday.”
“What I wouldn’t give to see what goes on in there. I wonder what kind of exercise routines they’ve got him on?” another woman remarked.
Robin was wondering exactly the same thing.

Chad felt a lot better after lunch, mostly because he was wearing clean diapers. That feeling alone was like heaven. He had even thrown caution to the wind and ordered an extra large size fries with his burger before coming back to work, because he was hungry. He realized that the baby cereal he had eaten for breakfast hadn’t really filled him up as much as he would have liked. Unfortunately, the extra large fries also came with an extra large drink. He hadn’t finished all of it, but it had just been such a pleasure to drink out of something besides a baby bottle for a change. As he predicted though, because of the extra drink, he was peeing more than he would have liked. But there was nothing he could do about that now.
He was getting down near the end of the project he was working on and he could clearly see the overall end results now. He felt a lot of pride in his work, especially this time. He knew the clients would love what he had done. As he was working intently, he suddenly realized that he was peeing. He stopped working completely and just sat there, trying to remember if he had known beforehand that he was going to pee. He had been working hard, not concentrating on peeing or having to pee. His mind had been completely busy elsewhere. Did he know he was going to pee and just put it out of his mind? He wasn’t sure, he couldn’t remember. He went back to work, but started watching himself. It had been another strange experience for him today.
Robin stopped by a little while later to ask if he wanted to go down to the break room with her. He didn’t even have to think of reasons not to go. “Not now,” he replied, still mostly intent on his work. “I’m getting close to finishing this thing and I’d really like to keep at it.” Then he ignored her again. But Robin didn’t leave. “Chad, I know you want to finish that, I understand, but do you think that later you can take a few minutes and look through this next project with me? I’ve come to a complete standstill on what I’m working on now.”
Chad didn’t really want to look up from what he was doing, but he understood her problem. “Yeah, maybe later, ok? I’m going really well on this thing right now and I’d like to keep at it.”
Robin seemed much happier. “Ok. Thanks Chad,” she said as she headed to the break room to talk with her friends.

Mel’s text message came in earlier than usual. She wanted him to head directly to her office after work instead of going home. He guessed the reason was because of the therapy session they were scheduled for later. He was looking forward to it. Unfortunately, it probably also meant that Mel would take him out to dinner somewhere beforehand. He prayed that for once she wouldn’t make him drink from another baby bottle while they were out. That was so embarrassing! But then with Mel, what wasn’t?

It was late in the afternoon when Robin stopped by Chad’s cubicle again. “Chad, can you please spare a few minutes to go through this thing with me? It’s getting late.”
Chad stopped working and looked at his watch. It was getting late. He had gotten a lot done though. He looked up at Robin. “Yeah, I guess. Let’s see what’s in the folder.”
Robin realized that he hadn’t even looked over the new material yet. “Chad, there’s a lot of stuff here and a lot of screen shots to look through. We need to lay it all out where we can see it better. Let’s take it down to the break room where we can use one of the tables.”
That was something that Chad really didn’t want to do. “Can’t we just spread it out here?”
“Chad, look at your desk. It’s a mess! And mine is pretty much the same. Besides, it’s still not enough room.”
Chad picked up his folder and flipped through it. “Shit!” he exclaimed softly. “There’s a ton of diagrams in here.”
“I know, I looked already. That’s why I suggested the break room.”
Chad nodded. It would be the only practical way. But he was still concerned. “You don’t think there will be too many people there right now, do you?”
“Chad, really! You’re the one who’s been coming to work dressed that way. If you can come in here like that, then I don’t see why you should have a problem going down there either.”
“Yeah, but here I’m hidden. Not many people stop by here.”
“Is that why you’re doing this? Just because you want to and you don’t think anybody is going to bother you down here?”
“No, that’s not why I’m doing it.”
“Then why?”
Chad shook his head. “You just don’t give up, do you?”
Robin smiled. “No… I don’t! So, what’s really going on?”
“Like I said, don’t ask!”
Robin was frustrated again. But they still had the project to look over. “Look Chad, we still have to go through this stuff.”
“Yeah, yeah,” Chad replied, clearly trying to put off what he was reluctant to do. But Robin was right, they needed room to spread the stuff out. “Ok,” he finally said as he got to his feet. “But I don’t know what I’m going to do if there’s anybody down there.”
“That’s a dumb question,” she replied, “you’ll stay there and work.”
The trip through the hallways was about like the day before for Chad, except that this time Robin walked next to him instead of holding his arm all the way. She also seemed more intent on talking to him as they walked. “So how come you’re wearing those shoes?” she asked. “I would think someone like you would have gone for higher heels instead.”
Chad groaned. “Someone like me?”
“You know, one of those guys who likes to wear women’s clothes.”
Chad looked for a way around her question. “So you’re automatically lumping me in that category?”
“Well yeah. What else am I supposed to think?”
This was getting harder by the second. “I don’t know… It’s complicated.”
“So explain it to me.”
“So you don’t like to wear women’s clothes, but you’re wearing them anyway. Chad, you have to know that doesn’t make any sense!”
Chad sighed. She just wouldn’t leave it alone. “Like I keep telling you, it’s complicated!”
But Robin kept at him. “So you do like to wear women’s clothes.”
“Yes… I mean no… not…” he stopped. Trying to figure a way to keep her from asking any more questions.
“Ok,” she said. “Let’s leave it at that. You do like wearing them.”
Chad wanted to scream. But by that time, they had arrived at the break room. Chad was elated to see nobody there. They chose a table at the far end of the room and spread their materials out. While Chad was busy looking at the various diagrams and screen shots, Robin got herself a cup of coffee.
“Look at this,” Chad said as soon as she came back with the hot cup in her hand, “Their old site looks really pitiful. This stuff is way out of date.”
“I know. I went to it on my computer. There’s a bunch of links that don’t even work.”
Chad saw her taking a sip of her coffee. “That looks good,” he said.
“So get some.”
But Chad was already a lot wetter than he really wanted to be. Anymore and he would be worried about it starting to show despite the girdle he was wearing. Besides, he figured that later, Mel would be pouring drinks down him again and the last thing he needed was coffee. But it did look good. “No thanks,” he replied, turning his attention back to their work.
But a few moments later, his attention was again brought back to Robins drink. “Chad, get yourself a cup if you want it.”
“No. Not today.”
Robin rolled her eyes. “Oh for heaven’s sake.” She set her cup down on the table and walked over to the coffee pot and poured him a cup. Then she brought it back and handed it to him. “Here! Now stop being contrary!”
“I’m not being contrary.”
“Then why wouldn’t you get a drink when you obviously want one?”
“Like I said, it’s complicated.”
Robins was suddenly very frustrated. “What the heck does getting a drink of coffee have to do with anything else? I’ve seen you drink coffee before. You had some right here yesterday!”
But Chad’s only reply was, “I told you…”
“I know! It’s complicated!” Robin finished for him. “What the heck can be so complicated about getting a cup of coffee, I’ll never know!”
But Chad had no real answer. He sipped at his coffee since he was now holding it and went back to studying the papers before him.
“So how do you want to divide this stuff up?” Robin asked.
“Why don’t you do the initial layout design, then we’ll take it from there. I’m still trying to finish what I’m on now.”
“Ok, that sounds good.” “You’re better at the artsy stuff than I am anyway,” Chad admitted.
Robin was slightly pleased by his compliment, but it was true. She had been an art major in college first. She started packing papers up in the folders. “Let’s get back so I can get started.”
“Fine with me,” Chad said as he took a bigger gulp of his coffee to finish it. As he did, he felt himself peeing again. And again, he wondered if he had realized it before hand that he was going to pee. This time, he didn’t think so. That was troubling… and a bit interesting.
Robin waited for him by the door while he threw his cup away and grabbed his folder. “So,” she started as they entered the hallway, “we know now that you like to wear women’s clothes.”
Chad inwardly groaned.
“Now we just have cut through all this complicated crap.”

Tuesday, November 24, 2009

The Bet - Chapter 13 (Thursday – week 2 Part 2)

The Bet
by Karen Singer

Chapter 13 (Thursday – week 2 Part 2)

When Chad finally left for work, he was still angry, but it was a different anger, much more muted. And what he was really angry at now, was not so much her, as himself. Feeling disgusted with himself for ever signing that contract in the first place he began descending the stairs toward his car. He could feel Mel’s eyes watching him from her apartment door. Halfway down the stairs, all the baby cereal he had eaten for breakfast finally triggered the suppositories in his system. He stopped dead on the steps as he began struggling against the inevitable. The mess began seeping out of him. He clamped down harder, straining against it. He took another step down and more leaked out of him. He stopped again, still struggling, realizing he was losing the battle. Another step… and he couldn’t stop it, not at all. Giving up, he slowly descended the last of the steps and walked gingerly to his car as the mess inside of him continued to come out of him and spread itself slowly all around his diapers. A process made all that much more miserable because of the girdle he was wearing.
Very gingerly, he eased himself into the driver’s seat and finally sat down. He fished his keys out of his purse and began his short drive to work. The main thought on his mind just then was his lunchtime diaper changing. An event that was all too far away!

“Hey Chad! Wait up!”
Chad turned as he was walking toward the building and saw Robin hurrying to catch up to him. He waited.
“Hi Chad,” she said a bit breathlessly as she slowed to a walk. She was carrying a huge tote bag slung over her shoulder.
“Hi,” he said back to her as he started walking again.
“Well you sound a bit dull today.”
“I what?”
“I mean you don’t exactly sound very happy.”
Chad mentally realized she had a point there. “Why should I?”
“I don’t know. So what are you so unhappy about?”
Chad just shook his head. “Everything!”
“So tell me about it.”
He glanced over towards her. She was still trying. Still prying like women tend to do all too much. He sighed. “Not today.”
“Hey,” she said a moment later. “You know you’re walking kind of funny today?”
Great! Just great! He was only thankful for everything he was wearing that would keep the smell from coming out.

Tom Robinson, Chad’s boss, turned the corner and hesitated just a second. He had almost stopped completely, but that wouldn’t seem normal. He had hesitated because he was afraid he might see Chad in the hallway… which was really dumb because he was on his way to see Chad right now. He had heard a few vague rumors, but nothing really concrete. He was almost afraid to see.
His problem was made all that much more terrible because of the meeting he had had with Mr. Baxter himself up in the executive offices yesterday. Mr. Baxter had told him, personally, that he wasn’t to take any kind of notice as to anything strange going on with Chad at all. He couldn’t yell at him or fire him… nothing. Not even talk to him about it, whatever it was. He had to completely ignore anything strange about Chad at all. And Mr. Baxter had pointedly made clear that he would be instantly fired if he didn’t comply… completely!
But he was still Chad’s boss. Ok, he didn’t see Chad all that often because Chad and Robin were stuck down here away from the rest of the department because it was the only place there was room for them. But he talked to him on the phone everyday, and he did keep up with Chad’s progress on his projects. So far, he hadn’t noticed any drop in the quality of Chad’s work. It continued to be excellent.
Which brought him to the reason he was coming down here now to see him… them. He turned into Chad’s cubicle. Chad was hard at work. He recognized the project on his computer screen. “Hi Chad.”
Chad was startled by his boss’s voice and he turned quickly. His fear grew just as fast as he had turned. His boss! Was he here to fire him? As Tom continued to look… make that stare… at him, he was more certain about that than ever. “Hi Tom,” he said, pitifully. Knowing what was about to come.
Tom wanted to say something about the way Chad was dressed, but Mr. Baxter’s threat stopped him. He couldn’t believe what he was seeing though. Chad was wearing eye makeup, and it looked like women’s pants, and a moment later he realized that he was wearing women’s shoes as well. He noticed the purse on the floor by the desk. He desperately wanted say something about it. Comment somehow, but he forced himself to bite everything back.
“Robin,” he called, knowing that she should be able to hear him over top of the cubicle wall. It took her only a moment to come out of her own cubicle and around to Chad’s.
“Hi Tom. What’s up?” she asked as soon as she saw her boss. But the one main thought that hit her brain was that Chad was about to get fired. So why had he asked for her?
Tom held up a couple of thick file folders. “New project. I’m going to need you both to work together on this one.” He looked up at Chad, feeling better about talking business. “Chad, you should be almost done with what you’re on now, aren’t you?”
Chad couldn’t believe his ears. Why wasn’t he being fired, or at least yelled at… or something? “Yeah,” he replied. “Probably anther two or three days and it will all be wrapped up.”
“Good,” Tom replied. “Robin’s project is going slower because the clients don’t really know what they want yet.”
“As usual,” Chad replied.
Tom nodded. It was so much easier sticking to business. “So I need you two to start looking through this and make notes and suggestions.”
“What’s the time frame?” Robin asked.
“There isn’t one yet. We don’t officially have the contract yet, so I need you two to help us get it. This could be worth a lot of money.”
Robin laughed, “As usual,” she replied, echoing the comment that Chad had just made.
Tom nodded. What was going on here? Robin was acting like there was nothing out of the ordinary wrong with Chad at all? Did she know what was going on with him? Would she tell him if he asked… privately? “Ok,” he said to the two of them. “Have at it and keep me informed.”
“Will do,” Robin replied.
Tom backed out glancing back and forth between Robin and Chad. In truth, he was retreating from the situation. He still desperately wanted to ask Chad about what was going on but Mr. Baxter’s threat was still ringing in his ears. With one last look at Chad he turned around and walked away. Maybe it was better if he didn’t know. For once, he was glad that part of his department was located so far away and isolated from the rest of it.
Robin looked at Chad. He was looking back at her. She had no doubt at all that the same thing was on each of their minds. It had been something that neither of them had mentioned before, but she brought it up now. “He didn’t fire you.” She said.
“No, he didn’t.” The amazement was clearly in his voice, even though he still sounded depressed. “Yet.” He added as he turned back toward his computer.
Robin walked further into his cubicle and picked up one of the folders that Tom had placed on his desk. “We’re going to have to talk about this,” she said as she glanced through some of the papers.
Chad turned back around again. He was still trying to come to grips with the way their boss had acted. “Yeah, I know,” he replied, although clearly his mind wasn’t on Robin’s subject.
She set her folder back down on his desk and leaned up against the doorway, watching him. “He didn’t even mention how you’re dressed.”
“No, he didn’t. But he noticed.”
“So why didn’t he say anything?”
“I have no idea. I’m still trying to figure that out myself.”
Robin picked up her folder again. “Well, if it had been me, you know I’d be all over you asking about it.”
Chad chuckled through his depression. “Haven’t you been?” “Yeah, maybe, but still, I’d be asking. Hey, I’m going down to the break room now, want to come?”
Chad shook his head. “No way, no thanks!” In truth, he was still trying to figure all too many things out, not the least of which now was his boss. But going down where, no doubt, he’d be attacked by all the women who would probably be there sounded like a really bad idea.
“Ok, see you later then,” Robin replied as she walked out.
Chad realized he was grateful he still had a job. But now that his boss had seen him, he had to wonder how long that was going to last.

“Hey girlfriend,” one of the women who was already in the break room called out as soon as Robin walked in. “What’s the latest with Chad?”
Robin shook her head as she headed to the coffee pot. “I still don’t know. And you wouldn’t believe it. Tom Robinson came in just a few minutes ago and handed us another project to work on… and he didn’t even mention the way Chad was dressed. Not a word.”
“You’re kidding!”
“I swear!” Robin replied. “Hey, who left all the donuts?” she asked picking up one from a box on the counter.
“We don’t know and we’re not asking,” another of the women said. “They’re not on my diet… but who’s going to tell!”
“So is there anything new about Chad today? I saw him walking in and the only different thing I could see was the tan slacks he was wearing, but I wasn’t that close to him. He did look like he was walking with his panties in a wad though.” That remark brought a bunch of laugher from all around.
“No, nothing different that I could see. And yeah, I did notice that he was walking a bit strangely, but he didn’t say anything about it.”
“Well dig deeper girl. Dig deeper. We want to know!”
“Yeah,” another one echoed. “How soon before he plans to wear a dress to work. Honey, I can’t wait to see that one.” That brought a lot more laughing.
“I’m trying,” Robin replied. “Believe me, I’m trying.”

Mel read the messages that Andrea had left for her while she had been with her last client. One of them was from Gloria, her therapist. She dialed the number quickly.
“Hi Gloria, it’s Mel.”
“Oh hey, Mel. How are you?”
“Doing just fine.”
“Good. I just wanted to touch base again before we get together tonight. You and Chad are still coming, aren’t you?”
“We’re both looking forward to it.”
“Good. Listen Mel, about your last request. I think that’s going to be a hard one.”
“Well, I understand perfectly if you can’t do it. It is a bit off the wall.”
“No, no. It’s nothing like that. It’s just something that I think is going to take a lot longer. Listen, what I want to do is to go back to my original plan with him. I don’t think we’ll have time for anything else, especially since it will only be his second time.”
“That’s fine,” Mel replied, only slightly disappointed. “Whatever you think is best. I just appreciate anything you can do to help me.”
“Good,” Gloria replied. “Now listen, I’m going to signal you again when I need you to stop listening, just like last time, ok?”
“Got it. No problem.”
“Then, once I think I have him under far enough I’m going to start working slowly on the incontinence thing. I want to do this in such a way that he won’t really notice anything different after the session. Since we don’t want him to know that he’s being hypnotized in the first place, I think that would be best.”
“Yeah,” Mel agreed. “That does make sense.”
“Ok, good. See you later then.”

Friday, November 20, 2009

The Bet - Chapter 13 (Thursday – week 2 Part 1)

The Bet
by Karen Singer

Chapter 13 (Thursday – week 2 Part 1)

In the early morning hours, before consciousness could take hold of him, he dreamed. In his dream, he was wetting his diapers, strongly. Something fought its way through to his sleeping conscious mind and Chad woke up with a start to discover that he really was peeing into his diapers. He was a bit unnerved because he realized that he had woken up, not because he had to pee, but because he was already peeing. It was a strange, and troubling, feeling. Yet, somehow, he found it exciting. His diapers felt bulky, more than he would have expected. Had he wet himself while he was sleeping? He didn’t think so because he was sure he would have remembered it. Besides, he had woken up this time. He pressed his legs closer together against the bulk of his diapers. They were full and heavy. Familiar and comforting. Still surprised that he had actually started to pee without waking up, he allowed himself to drift slowly back to sleep again. To dream.
But morning dreams are very different than late night dreams. Morning dreams are more sexually stimulating and therefore much more urgent. Little pinpricks of pain began seeping their way into his dreams. Disturbing little things. Adding elements to his dream that fueled his need even more, which in turn increased the pain of the pinpricks. He started to come more awake, but he still held on to his dream. A dream that was nothing but need and desire. Like a raging bull, that need seemed to overcome him, he reached for that need inside of his dream. The abrupt swelling of his penis brought instant severe pain to his half-asleep mind. The tight confines of his cock restraint suddenly added yet another misery. Even through the pain, he tried to will himself to get bigger, he wanted and needed it that much. Yet the restraint denied him completely. It’s diminutive size foiling him utterly. Losing the dream now and only wanting the feeling of getting hard, he fought harder against the pain and the device. But there was no way to win. No way to even come close to realizing any piece of what he wanted… needed. Foiled and in great pain, he came fully awake. He slapped both his arms against his blow-up mattress in frustration. “Aaarrrggghhh!” he yelled into the still dark room.
He rolled over onto his back and concentrated on the feelings he was getting from his device. Horrible feelings. The pain from those little teeth burned enormously. For the first time he could feel pain in the very tip of his cock from where the slits in the device for his pee to come out of were pressing all too tightly up against the tip of his penis. Pain from tip to base, and no way stop it. Even if he could get at it inside his all too bulky diapers, there would be nothing he could do about it. The only remedy for him was to get soft again… somehow. He slapped his bed and screamed again. He hated the dread device more than ever.
Not being able to sleep anymore, he got to his feet and made his way toward his living room, turning on his bedroom light as he went through the door. That light was enough to get him to his kitchen, not that he had to worry about bumping into any furniture anyway. He turned his kitchen light on and immediately noticed the note that Mel had left him sometime during the night. He walked over and read it.

One bottle as soon as you read this.
Get cleaned up and into two fresh diapers
Second bottle
Girdle and tan pants today, everything else is up to you
Don’t do your makeup at home, bring it all with you to do here
Third bottle
Don’t forget your pacifier when you’re not drinking

Chad read it and felt his anger grow. “Everything else is up to you,” he mentally repeated. The very phrase made him furious. She knew perfectly well that the only choice he really had was what shirt to wear. Of course he could always wear a pair of high heels to work instead of the low heeled shoes he had worn yesterday… but not likely!
He noticed again the bulk of the diapers between his legs. They were so full… so heavy that they sagged. Had he possibly wet himself without knowing it? Couldn’t be! He remembered again waking up that one odd time when he caught himself already wetting. It had been strange, really strange! Angrily, he grabbed Mel’s note and wrinkled it up into a ball and threw it at the bag he was using for a trash can. It went right in. He cared that it went in, but he didn’t care. The device was still hurting him. And he was angry.
He was suddenly very sorry he had ever agreed to this bet. He was tired of wearing diapers. He was tired of being so constantly humiliated that he’d never ever live it down. He had never dreamed things would be like this. He had never dreamed it could hurt so much. He wanted out. He wanted it to end. He had had enough.
He walked back towards his bedroom, intent on removing his diapers and ripping off the cling wrap that Mel had put around everything. Denying him. He was finished.
The bright light from the kitchen behind him mixing with the dim light of his bedroom cast strange shadows around his empty living room. As he waddled through, he couldn’t help but notice the framed contract that hung on his wall, one of the few things that was in the room. He stopped in front of it and just looked at it. He didn’t have to read it, he knew what was in it all too well. Mel was a lawyer, and he had no doubt a good one. His eyes fell on the signatures where the contract had been properly notarized… made all too official and binding. By the terms of the contract, the only way he could come out of this well was to win it. The reality of anything else was too horrible to think about. He wasn’t a quitter. He never had been. The contract was legal and binding. Quitting would only condemn him to a life of exactly what he was going through already. He had no choice, he couldn’t quit. His only real solution was to somehow win this bet. A bet he had no doubt at all that he could win… would win. But winning was still a long time away. In the meantime, he was stuck with whatever wicked and weird things she could think up to make him ever more miserable. And he knew now that she could be particularly devilish.
Disgusted and angry with his whole life, he headed to his bathroom to change his diapers early. Wow, they felt full. Had he wet himself in his sleep last night? Couldn’t be! He would have remembered it.

Mel allowed herself to sleep an extra half hour. When her alarm went off, she was already mostly awake. She stretched, enjoying the fact that for once she wouldn’t have to hurry out to unlock Chad’s onesie and he could change himself. She was fairly sure she didn’t have to worry about any of the reasons she had locked him in the onesie in the first place. With his chastity device now firmly in place and his toilet all sealed up, there wasn’t much he could do anyway. Thinking about how much under her thumb she had him now, stimulated her sexual need tremendously. She sighed. If only she wasn’t on her period!
She got up and went into her kitchen to make some coffee, then headed to take her shower while it was brewing.

Chad sat dejectedly in the only chair he had, finishing his third baby bottle of the morning. He had already peed twice since he had changed himself earlier. He considered changing himself again before he went to work. But glancing at his watch told him he didn’t have enough time. Feeling angry and depressed, he finished his bottle, then dropped it into a small bag with his other empty bottles to carry over to Mel’s apartment because he was sure she would want to see them.
He picked up his purse as he headed for his door and stopped. His purse. He was carrying a damn purse like a girl… full of makeup! Not to mention the way he was dressed. Thinking about it fueled his driving sexual need, which sent pain to the root of his cock, which made him angry again… well, more angry. Damn the woman for doing this to him! Not knowing any way out of it, he opened his door and walked over to Mel’s apartment.

Mel was fully dressed and enjoying her coffee by the time that Chad knocked on her door. She set her cup down and went to let him in. She opened the door and purposely stood in the way, waiting, not letting him in. He stood in front of her, looking at her silently. Did she detect a hint of anger on his face? “You have something to say?” she asked.
“Good morning, Mistress,” he said to her. There was definitely a hint of something not right in his voice.
“I can see we need to do more practicing tonight,” she replied. “Now do it right and curtsey!”
Chad was aghast. “Out here?”
“Of course! There’s no reason why you can’t do it anywhere!”
Chad wasn’t happy about it, but she wasn’t giving him much of a choice. Realizing that his hands were full, and he couldn’t reach down like he was grabbing his skirt, he replied, “But my hands are full.”
“Then you do what you can!”
Chad held back his anger only with great restraint. He put his right foot behind his left and dipped down. “Good morning, Mistress,” he said again.
Mel nodded and stood back. “Much better.” As he walked past her and she closed the door behind him, she was more convinced than ever that something was eating at him.
Chad dropped his purse on the floor and handed her the bag containing the empty baby bottles. “Thank you,” she said as she grabbed the bag and looked at the contents inside. He had been good again.
“Can I get started on my makeup now?” he asked flatly.
“Not yet. I’ve been nice to you this morning and made you some breakfast. Now come into the kitchen and eat it.”
Breakfast? He couldn’t believe it. She… had made him some breakfast? He followed her into the kitchen where she pointed at his usual spot on the floor. He sat down.
“Where’s your pacifier?” she asked as she pulled a baby bottle full of her tea mixture out of the refrigerator and handed it to him.
Chad rolled his eyes. “I left it home. I forgot it. Sorry.”
“You can get it later,” she replied as she headed toward her counter. She picked up a bowl and the spoon that was laying next to it. She turned around and handed Chad the bowl. “Some nice warm cereal for you this morning,” she said.
Chad took the bowl from her hands and looked at the contents. It looked kind of like oatmeal, only completely smooth. The bowl felt slightly warm so it probably was some kind of oatmeal. Well, that was fine with him. He would have preferred pancakes or something like that, but he appreciated the effort. “Thanks,” he said.
Mel stood up straight. “I think you can do better than that!”
Chad corrected himself quickly. “Thank you, Mistress.”
“I can see we still have a lot of work to do with you.”
Chad was about to start trying to stuff the oatmeal into his mouth with his fingers when Mel stopped him. “I think we can let you use a spoon for that this morning,” she said.
Chad detected something in the tone of her voice, but couldn’t tell what. He quickly found out though as she produced a tiny rubber-coated baby spoon and held it out for him. He took it hesitantly. The thing was so small. But it was better than eating with his fingers. He stuck the spoon into the cereal and scooped some up. He was dismayed to see how little the spoon had picked up. Not much to put into his mouth. He tasted the cereal, bland, very bland, but eatable. It didn’t taste like any oatmeal he had ever had. He tried to scoop up a bigger amount and put it into his mouth, but the baby spoon was too small and part of it dripped on his chin before he could get it all into his mouth.
Mel laughed when she saw him dripping on his chin. “Maybe we need to get you a bib too.” She turned and opened one of the drawers and pulled out a dish towel. She draped it around his neck to catch any further drippings. “More and more like a baby,” she teased. “How does your baby cereal taste?”
Chad was shocked. “Baby cereal!” He looked down at the bowl then back up at Mel. No wonder she had made him breakfast. It was baby cereal! “Kind of bland and not really very good,” he replied.
“That’s what’s best for babies,” she replied. Then she turned away while he continued eating.
As Chad ate the baby cereal, he felt even more humiliated. The damn woman could certainly come up with the darnest ways to make his life more miserable. That was for sure. As he continued eating, he quickly discovered that trying to eat with that tiny spoon was far more difficult than if he had been using just his fingers. It certainly took a lot longer too. Worse, the more he ate, the worse the stuff started to taste. When he started eating it, it had seemed to taste fine, just a little bit bland. But soon he was having to put a little in his mouth, then take a swig from his bottle just to keep eating it. By the time he was half-finished, he was forcing himself to continue eating. “Mistress!” he called desperately.
Mel came quickly back into the kitchen. “I can’t eat it anymore. I can’t even get it down. It’s horrible!”
“Awww,” Mel crooned. “Babies love it. So I guess you’re going to have to learn to love it too.” She noticed that the bottle next to him was almost empty. She pulled yet another one out of the refrigerator and set it down next to him. “Just in case you need it,” she said. “Now finish it all up like a good little baby.” She was chuckling to herself as she walked away.
Chad just stared at her retreating back. Damn the woman. “Finish it all up,” she had said. Yuck! He went back to work on the bowl of mush. He wasn’t happy about having another bottle to drink either, but he’d need it to get this all down.
By the time he finished, his stomach really wasn’t feeling all that well. “Mistress, I’ve finished,” he called from his spot on the floor.
Mel came back quickly and took the bowl from him. “Oh what a good baby you were. See, that wasn’t so bad now, was it?”
Chad wanted to tell her in no uncertain terms how awful the stuff was, but he said nothing.
“Oh come on,” Mel crooned at him like he was a baby, “tell me how much you liked it.”
Liked it? His stomach felt sick now from the junk! He got to his feet, the anger in him slowly building again. He felt the need to pee again as soon as he was standing. Frustrated at having no where else to go except in his diapers he let it out.
“Aren’t you going to tell my how much you liked it?” Mel asked again, this time in a much more angry tone of voice.
Something in Chad began to snap. “Like it? It was terrible! I feel sick now from it! I feel sick now from all of this crap!” He walked off into the living room.
Mel followed right behind him. “What are you saying?” she asked menacingly.
Chad’s anger finally came all the way through. “I’m sick of all this! I’m sick of wearing diapers. I’m sick of being constantly humiliated. I’ve had enough. I’m finished. And I want this damn… thing… removed from my cock… now!”
But he was up against a well seasoned lawyer who was well used to fighting back and winning. Mel had been in a lot of battles in court that were a lot worse than this. Her lawyer instincts and training took over. “So you’re quitting?” she said almost gleefully.
“Damn right!” he replied.
“You know what that means, don’t you? It means that I win and that you have to continue to do anything I want you to. Which means that I’m going to keep doing just what I’m doing now… and more!”
“Like hell!” Chad replied. He was frustrated. He already knew what the contract had said. He just didn’t want it anymore.
Mel went quickly to her desk and grabbed her framed copy of the contract and brought it back to him. “See that?” she asked. She pointed at the signatures. “See where you signed it? You signed it because you knew you might want to back out someday. You signed it to make sure you wouldn’t have any way to back out. You signed it to make sure that no matter how much you wanted to quit, you wouldn’t be able to. You signed it… yourself. And you did it in front of not only me, but another outside witness. You signed it in front of a legal notary. And there’s her stamp of certification! And you did it willingly didn’t you?” She waited for his answer. She knew she had him, but he had to fully realize that again. “You did it willingly, didn’t you?” she repeated, pressing him.
Finally he nodded his head. “Yeah,” he replied softly. She could see the anger in him starting to subside, but it was still there, mixed with confusion.
“Yeah,” she repeated back to him, mocking him. “Yeah… you signed it willingly, knowing full well what this meant. Knowing that the only way out for you is to win this bet. Isn’t that right? Hmm? You knew it!”
Chad nodded his head again. He was looking down at the floor now, felling sorry for himself. “Yeah, he said again.
“Yeah,” she repeated. Again mocking him. “So which is it now, are you saying that I win so I can get on with turning you into exactly what I want? Or are you just feeling sorry for yourself?”
Chad’s mind had dropped into total numbness. He was trapped and he knew it. Furthermore, she had quickly pointed out that he had trapped himself. He had done it to himself. By signing that thing in front of the notary, he had locked himself into all of this. And he had done it willingly. No matter that he didn’t want it anymore, he was stuck. His only way out now was to win the bet. A bet he was still fairly sure he couldn’t lose, which was a good thing because he wasn’t at all sure he liked any of this anymore, at least not right now. He was stuck, stuck, stuck!
“Well?” Mel asked again. “Do I win? Say it. Say it plainly so there’s no misunderstanding for either of us.”
His only way out was to win. And he could win. He had no doubt of that at all. A tiny spark of life seemed to return to him. A spark of life and confidence. “No!” he said. “You don’t win. This bet is still on! There’s no way you can win.”
Mel had been sure from the start. She had just been surprised at the way it came out. “So you’re just starting to feel sorry for yourself, is that it?”
Chad took a deep breath. “Yeah,” he said.
Mel had worked with enough clients with heavy troubles to know there was a time to push hard and a time to go easy. She returned the framed contract to her desk, giving him more of a chance to recover himself. She had no doubt at all that he was feeling really sorry for himself, but that was something he was going to have to get past. It was time to make him realize that he was still riding her train. Time to show him he was on her track… But only just a little. “Tell me you’re sorry,” she said.
It took a moment, but finally he let out a small, “Sorry.”
“That’s not an answer!” Her voice whipped at him like a lash. He looked up at her, clearly startled. “You do it properly… and curtsey!”
Chad was so startled and off balance that he didn’t even pause. “I’m sorry, Mistress,” he said as he dipped into his curtsey.
Mel nodded as if she were satisfied. “That’s better!” she replied. “Oh, we’re definitely going to have to do a lot more work with you tonight! Unfortunately, we can’t get started too soon because we have therapy this evening. But you can bet you’ll be practicing a lot more, later!”
Therapy… Chad had forgotten all about that. It had been the one, and only, really good thing he had done last week. Suddenly he had something bright to look forward to today.
Mel saw Chad’s face change a bit as soon as she had mentioned the therapy session. He was recovering from his bout of anger and quickly. It was time to keep him moving. “Ok, Sissy, do your makeup now.”

Tuesday, November 17, 2009

The Bet - Chapter 12 (Wednesday – week 2 Part 6)

The Bet
by Karen Singer

Chapter 12 (Wednesday – week 2 Part 6)

Even though Sandy had been there once before, this time she was looking carefully around at Mel’s apartment. “Nice place,” she said. “Even though none of your furniture looks like a matching set, it still works well together and it looks nice and comfortable.”
“I’m afraid I only do what decorating I can. It’s not something I’m good at. Do you want to see the rest of the place?”
“Sure,” Sandy answered.
Mel started showing them around. When they were passing the empty corner where she had been making Chad stand whenever she ate, she said, “And that’s the corner where I’ve been keeping him when I don’t want him doing anything else.” She paused for a moment, then added, “I just need a way to make sure he stays there a little better, he fidgets too much, but I’m working on it.” Sandy glanced at Cassie as they moved from the living room into the kitchen.
Suddenly there was a very loud ding from the kitchen timer. “Sissy! You can stop now,” Mel said. Chad gratefully stopped his practicing. He was really starting to hurt. “Have you peed yet?” she asked.
“No Mistress,” he said, and then dropped into a quick curtsey, slightly after the fact.
“You better start getting it together pretty quick,” she told him. “Practice that now!”
Chad started curtseying all over again, only this time saying “No Mistress.”
“Just don’t forget to tell us the minute that you pee,” Mel said as she turned back to showing her guests around.
“It was another five minutes before Chad felt the first signs that he was going to pee. He stopped what he was doing. “Mistress, I think I’m going to pee soon.”
“Did I tell you to stop?” Mel asked.
“No Mistress,” Chad replied as he went right back to his curtseying again.
“You need to learn that peeing is never a reason to stop what you’re doing. It should happen automatically! Now don’t forget to tell us when you’re done peeing.”
Chad’s curtsying response changed from “No Mistress” to “Yes Mistress.” While the women were ignoring him, Chad concentrated on the feelings of needing to pee. He desperately wanted it to happen so that he could stop curtseying. Finally, he felt it coming out. He was very careful to keep practicing while it was happening. The bottle attached to him began to get heavier and heavier as he continued to pee. When he finished, he called, “Mistress, I’ve finished peeing,” and he dropped another curtsey as he said it just to make sure she wouldn’t yell at him again about it.
“Very good,” Mel said sounding very pleased. “You can stop now.”
Chad stopped and tried to catch his breath. His legs were starting to cramp. He was very embarrassed over the bottle half-full of pee attached to him, but coupled with everything else he was already embarrassed about, it meant almost nothing.
“What do you say Sissy?”
He immediately curtseyed again and said, “Thank you Mistress.”
Mel smiled. “Maybe you are leaning.” She turned to Cassie, “Will you set the timer for twenty minutes?”
“Sure,” Cassie replied and reset the timer, not knowing why she was doing it.
Mel smiled wickedly at Chad. “You now have exactly twenty minutes to pee again or get punished for it.”
Chad inwardly groaned. Twenty minutes wasn’t a very long time at all!
Mel looked at the clock. It had taken him an extra ten minutes longer to pee than she wanted. She went over to inspect the bottle attached to the front of him. It was a little more than half-full. Too full to continue without emptying it. She untied the cord that was wrapped around Chad’s body, then pulled hard on the bottle. Chad suddenly started to double over in pain. She realized the chastity device was hurting him as she pulled on it. The bottle was being stubborn though and she still had to get it off. She brought him into the bathroom and coated everything she could with baby lotion to lubricate it. Then she pulled again. The tiny teeth again stuck painfully into Chad, but this time the bottle came off. She emptied it, then put it all back in place again, tying it firmly around him.
She brought him back to where he had been practicing in the living room, then she picked up her yardstick. “You took ten minutes too long to pee. That means ten strokes! Now, every time I hit you, I want you to thank me… properly!”
Chad was suddenly scared. He wanted to cry. He knew how her yardstick could hurt. He couldn’t help it if it took him too long to pee. He didn’t get to think about it much longer though since her yardstick suddenly came swooshing at his backside. He let out a little cry of hurt and jumped.
“I’m waiting,” Mel said, ready to brandish her yardstick again.
Chad immediately curtseyed and said “Thank you Mistress.” Then she hit him again. The process was repeated for ten full, hard strokes. At the end of it, Chad really wanted to cry, but he didn’t.
“You can sit for a few minutes and rest now,” she told him. “And don’t forget to tell me if you pee!” She then went to her refrigerator and brought out one of the cold bottles of tea. As she did it, Sandy’s eyes went wide at seeing so many baby bottles in her refrigerator. Mel handed the bottle to Chad. “Drink up, baby. Let me know as soon as you finish that. And if you take too long, I’ll punish you for that too.”
Chad put the bottle to his lips and drank furiously, afraid of any more punishment. But the truth was that the cold liquid felt really good on his throat. He was dry from talking almost constantly. And the beating he had just gotten hadn’t helped either. If he wanted to avoid any more beatings, then he was going to have to figure out how to make himself pee sooner. One thing he realized quickly about that… he had no idea as to how he could possibly do it.
It seemed like all too soon that Chad finished his bottle. He had been trying to stretch his legs while he sat on the floor. It helped some, but not really a lot. They still felt really tired. He felt really tired, all over. He prayed that Mel would let him go to bed soon, but she was still talking with Cassie and Sandy. “I’ve finished my bottle,” he called to Mel.
Mel stopped talking and turned her head. “You’ve what?”
Her tone surprised him. She sounded angry. He was so tired that it took him a moment to realize what she wanted. “I finished my bottle, Mistress,” he corrected himself.
Mel smiled and walked over to him and grabbed his bottle. “That’s better,” she said. “Now stand up and start practicing again.”
Chad couldn’t believe it. He still hadn’t recovered from the last round. But Mel was standing over him, waiting. Wearily, he got to his feet.
“You’re doing better,” Mel said.
Chad curtsied and said, “Thank you Mistress.” And as Mel stood there and watched, he did it again, and again, and again… even though she had long ago walked off.

Chad was beginning to feel like he was going to pee soon when the dreaded timer went off. He had almost made it, but almost wasn’t good enough.
“Have you peed yet?” Mel asked.
His phrase while he was curtseying changed immediately to “No Mistress.” Chad concentrated hard on trying to pee, and was rewarded when very soon he was filling the bottle again. He was about to tell Mel what he was doing, but stopped himself just in time and continued his curtseying practice. When he was sure he was done, he called. I’ve finished peeing Mistress.” Then he went back to saying “Thank you Mistress,” as he continued curtseying again.
“Very good!” Mel replied. “You can stop now Sissy.”
Gratefully, Chad stopped curtseying, then catching himself, he dropped one more, saying “Thank you Mistress.” After that, he tried shifting his weight and bending his legs to get the pain to subside. It wasn’t working very well.
“Will you please put another twenty minutes on the timer,” Mel asked Cassie. Cassie got up and immediately went into the kitchen while Mel again led Chad into the bathroom to empty the bottle.
When everything was back in place again, Chad had to thank Mel for the three strokes from her yardstick for each of the three extra minutes it had taken him to pee. Then he had to sit back down and drink yet another bottle. He both hated and loved it. He hated it because he knew he’d be awake peeing all night long. He loved it because he really needed the drink.
All too soon again, he found himself back in curtsey practice while Mel and her friends talked and ignored him. The strokes from her yardstick had hurt. He hurt all over from curtseying so much. And he was dead tired. He desperately tried to make himself pee. Every time he dipped down to curtsey, he pushed at it. Loosening his muscles, trying to get something. And then it happened. The suddenness of it came as almost a surprise. No long buildup this time, just quick pressure then release. He was doing it, peeing into the bottle before the timer went off. Happily, he dropped one more curtsey saying, “I’ve finished peeing again, Mistress.” Then he went back to saying “Thank you,” as he continued his practicing.
Mel was really surprised. But she got up from her chair all smiles. “Cassie, check the timer. How long did it take him?”
“Thank you Mistress,” Chad said as he dropped another curtsey… not to Mel, but because she hadn’t told him he could stop yet.
“You can stop now Sissy,” she said. Gratefully, Chad said one more thank you and stopped. Mel was still smiling, you’re learning nicely.
Chad’s curtsey and “Thank you Mistress,” was almost a reflex.
“Fifteen minutes!” Cassie called from the kitchen. “Do you want me to reset it?” “No,” Mel replied. “I think he’s had enough for tonight.” She walked up to Chad. “Fifteen minutes. That’s a lot better than I had hoped for. We have a new goal for next time now.” Chad inwardly groaned. He had no doubt he would be getting a lot more beatings next time.
“Ok baby, let’s get you ready for bed.” The words were like heaven to Chad’s ears.
A few minutes later, Mel was diapering him while Sandy and Cassie looked on, all too closely. She shoved two suppositories up his backside, coated him liberally with baby lotion and taped four diapers firmly into place. Then finally she pulled his plastic panties up. “Let’s take you home now,” she said to him.
Mel grabbed his skirt and pantyhose that he was no longer wearing. Chad grabbed his purse that he had set by the front door. He dug his keys out of it before they left her apartment so he wouldn’t have to stand outside too long dressed like he was. Then all of them went over to his apartment.
“It’s so empty,” Sandy noted as they walked inside.
Mel helped Chad remove his blouse and the bra he had been wearing underneath. Then, instead of locking him in his onesie for the night, she put the baby-doll nighty set on him again. Chad was clearly surprised, but he said nothing. He just wanted to go to sleep.
Sandy and Cassie were clearly fascinated by the whole thing. “Oh, how sweet,” Cassie chided when he was finally ready for bed.
Mel led him over to his blow-up mattress and had him sit down on it. He yawned. “I’ll be right back with your bottle,” she told him. Sandy giggled behind her. She returned shortly and handed him the bottle she had pulled from his refrigerator. Chad immediately put it to his mouth and started drinking it.
Sandy laughed. “I just can’t get enough of watching him do that. He drinks it just like a little baby.”
Mel smiled. “I know. I only allow him to drink from the bottles and nothing else, even when we’re out in a restaurant.”
Both Cassie and Sandy went into fits of laughter. “Oh God! How I’d love to see that!” Cassie stated.
While Chad was drinking his bottle, Mel busied herself setting up his diaper bag again for the next day. Then she went to his alarm clock and set it herself for the time she wanted him to get up. Chad was just finishing his bottle and she took it from him.
She helped him lay down on his mattress and she covered him with his blanket. She grabbed his pacifier from where she had set it earlier by his clock and put it into his mouth. His teddy bear she tucked under his arm. “I’ll be back later tonight and leave your instructions for you in the kitchen. Good night, baby.” Then she kissed him on the forehead and got up.
Cassie giggled softly. “May I?” she asked. Mel nodded. Cassie too went over and kissed him goodnight. She was followed immediately by Sandy. Both girls giggled softly as they left him for the night.

Chad gratefully closed his eyes. He was so dead tired he could barely think. He was very grateful that his day was finally over. Once again Mel had found a way to make things even worse and more embarrassing than the day before. Again he didn’t want to think about tomorrow. Tomorrow would have to keep. He was too tired.
He realized that he had to pee again. He had just peed a few minutes ago as soon as he had started drinking his last bottle. He let it out without any thought of holding back. Holding back did no good and only made him miserable. Why couldn’t he have been able to pee this soon earlier? It would have saved him a lot of pain.
Now if only he could get some sleep. The stupid chastity device she had locked on him wasn’t hurting him at all. He could feel the tightness of where it was connected to him, but that was all. His only problem now was waking up to pee too often. He really wished just then that he really was incontinent, then he could at least pee in his sleep without waking. He had even dreamed of it several times that week. If only, if only, he dreamed.
Chad fell asleep. Deeply asleep. He half woke a bit later when he had to pee again like he usually did. The next time, he didn’t wake at all. He was too tired.

Friday, November 13, 2009

The Bet - Chapter 12 (Wednesday – week 2 Part 5)

The Bet
by Karen Singer

Chapter 12 (Wednesday – week 2 Part 5)

As Chad was busy with the dishes, he suddenly felt the suppositories that had been in his system all day going to work. It wasn’t as sudden as it often was, but the pressure couldn’t be denied. Grunting, not from exertion, but from the discomfort and not wanting to do it at all, he let it all out into his diapers. Then because he had no other choice, he simply went back to work. He noticed that the suppositories were working more and more often after he had eaten something. Could he go for the next two months and never eat again? Unfortunately not.
Mel heard Chad’s noises as she was working on the baby bottle. She smiled. “I need to know every time you pee now,” she yelled to him. “Make sure you tell me!”
Chad shook his head. What did she need to know that for?
“Did you hear me?” she yelled.
“Yes!” he replied.
“Yes what?”
He sighed. “Yes, Mistress.”
Mel got up from her desk to see how far along he was with the dishes. Half-way to the kitchen, she saw him yawning. She had forgotten how tired he must be. She doubted he had slept much last night at all. Fortunately, he was just finishing up and wiping everything down. She could have just let him put everything into the dishwasher, but she figured a little extra hands-on work never hurt.
When he had finally finished, she went to the refrigerator and handed him yet another baby bottle to drink. Chad couldn’t believe it. He had already had far more than normal, but he took it reluctantly and sat down in his usual place on the floor while Mel busied herself making more of her tea mixture. Chad wasn’t exactly happy to see her doing it.
Halfway through his bottle, he felt the urge to pee again. He figured he’d probably be doing it every ten minutes all night long now with everything she had already made him drink. “I have to pee,” he told her as she was stirring the tea in her pot - like a witch brewing her dark and deadly potion, he thought.
“Good,” she replied without even turning around. “Let me know when you’re done.”
Two minutes later, he replied, “I’m done.”
She cocked her head without turning. “You’re done… what…”
“I’m done peeing… Mistress,” he added at the last second.
Mel nodded her head far more satisfied. “Finish your bottle now.” Then she glanced at the clock and took note of the time. She finished making her tea and poured it all into the empty baby bottles. In the meantime, Chad had finished his bottle and just sat on the floor waiting for her to finish.
Finally, she took the bottle from him and said, “Ok, come on, let’s get you out of those messy diapers.” She reached out her hand and Chad got to his feet, and he let her lead him like a child into the bathroom. He couldn’t believe his good luck. She was actually being nice to him. He yawned again as they entered the bathroom. Now if she would only let him go to bed early tonight.
But she saw him yawning. “Tired?” she asked.
“Very,” he replied.
“Well, maybe we can get you to bed early tonight.”
“That would be good,” he replied as he removed his skirt.
“Of course, it all depends on how cooperative you are tonight,” she replied.
Chad wasn’t sure he liked the sound of that. He removed his shoes and his pantyhose but Mel had him keep his blouse and bra on so that he would only be naked from the waist down. He was about to lay down on the floor so she could change him when he noticed the urge building that told him he would have to pee again soon. “Mistress,” he said, “I think I’m going to have to pee again.”
Mel stood back. “Good. Just let it out and tell me when you’re done.”
But it was just some preliminary feelings. The two of them had to actually wait a few minutes before he was finally able to pee. “I’m done now, Mistress,” he said. “Finally!” Mel replied. “Ok, lay down and let’s get you cleaned up.”
Mel removed his messy diapers and used baby wipes to clean him up. Then she examined his chastity device closely. It didn’t appear to be irritating him too much she noticed. She was very glad of that. But instead of rediapering him, she had him get to his feet. Chad was confused. He was still naked.
Mel took him by his hand and led him out into the living room to an area near the corner where she had made him stand earlier. “Wait here,” she told him. Then she dug through one of her desk drawers and pulled out a small piece of rope. She brought it back to him and tied his hands loosely behind his back.
“Now what?” was all Chad could think. He was beginning to be afraid of getting beaten again since that’s what the rope usually meant. But instead, Mel went back to her desk and picked up the baby bottle she had been working with earlier. Chad could see that she had tied a piece of cord around the neck of it.
Mel knelt down in front of him. “Now hold still!” she commanded. She grabbed his chastity device and tried to push it into the opening of the baby bottle, but it didn’t want to go. She pushed harder. Chad had to struggle to stay still and not get knocked over. But suddenly, with a soft pop, the bottle slipped into place. “Good,” Mel said sounding very satisfied. “That was a bit tighter than I thought. For a minute there I thought we’d have to remove your device.” Looking at the baby bottle now attached to the front of him, Chad had mixed feelings about removing the device or not.
Mel brought the cords attached to the bottle up around his waist and tied them securely to make sure the bottle wouldn’t come off. Then she stood back and admired her work. She again felt a rush of sexual pleasure over the power of what she was doing. If only she wasn’t on her period!
“Ok, Sissy,” she said as she walked around and untied his hands. “Time for some new training.” She stood back. “Curtsey for me.”
Chad was really very surprised. Curtsey? His cock immediately started to try to get hard and the awful spikes immediately dug in. Mel noticed the look of pain on his face and laughed. “I’m glad you think it sounds like fun,” she said. “But you’re going to have to stay all nice and soft I’m afraid. Now… curtsey!”
Chad did his best. It was actually something he had never even tried before. Mel shook her head. “Not very good,” she said. “Now, this time I want you to pretend you’re wearing a skirt like you usually would and spread it out wide. And put your right foot behind your other foot further! Now try it again.”
Chad felt incredibly silly, especially with the baby bottle now dangling from the front of him. He tried it again, pretending he was grabbing the sides of a wide skirt and holding it out. “Better,” she replied. “Now I want you to say, ‘Thank you, Mistress,’ as you’re doing it… Now!”
Chad immediately curtseyed again and said “Thank you, Mistress.”
Mel smiled. “I like that. Oh, I like that so much! Dip lower this time and bring your right foot back even further! Now again!”
“Thank you, Mistress,” Chad said as he curtseyed again, trying to get it just the way she wanted it. It felt weird, not only because it was something he had never done, but much more so because of the baby bottle dangling from the front of him.
Mel smiled. “Do you need to pee yet?”
“No, not yet,” he replied. He was a bit stunned by her question since he had just peed a few minutes ago.
But suddenly Mel wasn’t smiling. “It’s ‘No… Mistress!’ Now do it right!”
Chad was a bit taken aback by her suddenly yelling at him, but he immediately said, “No, Mistress.”
“You still haven’t got it, do you? You curtsey every time you say it! Now do it again!”
Her manner was leaving Chad with no question that she was demanding to be obeyed. He curtseyed again and said, “No Mistress.”
“That’s better. Now let’s try it again. Do you need to pee yet?”
“No Mistress,” Chad said, dropping another curtsey.
Mel smiled. “See how good you can be? Now, I figure it’s been at least ten minutes since you peed last. So I’m giving you ten more minutes to pee. If you don’t, then for every minute longer that it takes, I’m going to give you a really hard smack with my yardstick. Understand?”
Chad’s eyes went wide. “Yes… Mistress,” he added.
Mel instantly walked up to him and slapped him. “You didn’t curtsey! Now do it right!”
Chad was stunned. It took him a moment to recover. “Yes, Mistress,” he said as he dropped another curtsey.
“Good,” she said sounding satisfied. “Now, you’re going to stand there and practice curtseying over and over again till I tell you to stop. And I want to know the minute you pee. Got that?”
Chad hesitated, but then he dropped into a curtsey and said, “Yes Mistress.”
“Good. Again!” Over and over again, Mel had him practicing, establishing the rhythm for what he was doing, and never letting him stop. Finally, she left him practicing and went into the kitchen where she found and set her kitchen timer. She set it for ten minutes to give him the benefit of the doubt.
As Chad droned on in the background with his “Yes Mistress” over and over again, she went and found her yardstick. She leaned it prominently up against the end of her couch in front of him. “Keep practicing,” she ordered as she saw him hesitate and his eyes opened wide. He went back to it, but the look on his face clearly showed more worry than anything else.
Chad’s eyes never left the yardstick as he dipped up and down, practicing and reciting the words that had now become a meaningless phrase. He wasn’t happy in the least to see it. The yardstick could only mean more pain for him and he had enough just then from the stupid device he was wearing. The calf of his left leg was really starting to ache. His right knee was getting very tired too. He was using muscles he wasn’t used to using this way. But the sight of the yardstick kept him at it.
Mel turned on her TV. She wasn’t the least bit interested in watching it, but she was trying to act like she was ignoring him. The power of what she was doing was really turning her on. If only, if only! But then someone knocked at her apartment door. She quickly turned the TV off. Chad had stopped. “Keep practicing!” she ordered. Hesitantly, he went back to it. She had no doubt that he was scared now because there was someone at the door.
She went to her door and opened it. Cassie and Sandy were both standing there. She had almost forgotten that she had invited them. “Hi,” she said, seeing the two women there.
“Hi Mel,” Sandy replied. “We came to see how Sissy is doing.”
Chad hesitated again as he saw Mel suddenly step back and let Cassie and Sandy into the apartment. But noticing the menacing look on Mel’s face, he only hesitated for a moment before he went back to it again. He was suddenly far more embarrassed than ever.
Cassie’s eyes went wide as she stopped and stared at him but Sandy just squealed with delight. “Aaaahhhh! Look at him! Mel, what the heck do you have him doing?”
“I’m killing two birds with one stone,” Mel replied. “He’s learning to curtsey and to address me properly, and he’s learning to pee more often.” She turned to Chad. “Sissy, say hello to Cassie and Sandy.”
Chad stopped what he was doing. He was embarrassed out of his mind. But stopping quickly brought a little physical relief for his aching legs. “Hello Cassie and Sandy,” he said.
Mel moved like lightning and in a flash she had her yardstick in her hand and was hitting him over and over again. “That’s not any way for you to greet someone properly! From now on you curtsey and address them by name – separately!” Chad had retreated all the way back into the corner to get away from the blows, even though not a single one missed him. “Now get out here and do it again… right!”
Chad slowly moved back out to where he had been standing before. He looked briefly at Mel, she was waiting, holding her yardstick at the ready. He curtseyed and said, “Hello Cassie.” Then he did it again and said “Hello Sandy.”
“That’s better,” Mel told him. And then she waited a moment. When he didn’t reply, she said, “And what should you answer to what I just said?”
Chad’s eyes went wide, then he dropped into another curtsey and said, “Thank you Mistress.”
“That’s better,” Mel replied. “Do it again.”
Chad again curtseyed and said, “Thank you Mistress.”
“Keep doing it!” Mel ordered.
Chad inwardly groaned, but he went back to practicing, this time with the slightly different phrase.
Cassie and Sandy both had been alarmed as soon as they saw Mel beating Chad, but now they were all smiles. “You’re really turning the screws,” Cassie said.
Mel smiled. “I’ve got to. It’s about time he learned to behave properly.” All the women giggled while Chad droned on in the background.

Tuesday, November 10, 2009

The Bet - Chapter 12 (Wednesday – week 2 Part 4)

The Bet
by Karen Singer

Chapter 12 (Wednesday – week 2 Part 4)

Chad’s cell phone beeped again just before quitting time. Again, it was a message from Mel, telling him to go home again where he would find more instructions. He was glad. He was way too tired to do anything else. He just hoped that whatever Mel had in store for him for the evening would be easy. He really just wanted to go to bed and sleep – forever!
When he finally got home, he found a note again on his kitchen counter.
Sissy,Drink one baby bottle.
Change your diapers.
No girdle today
Wear a bra and stuff it with more pantyhose
Same skirt, blouse, and shoes as yesterday.
Do better with your makeup!
Drink another bottle.
Pacifier in your mouth whenever the bottle isn’t!
I put the key in your top dresser drawer today.
More instructions at my apartment if I’m not home before you get there.
Your Mistress

The note didn’t really surprise him, except the part about no girdle tonight. That alone made him glad. He was also glad that he could finally get changed. Going to his refrigerator he pulled out another baby bottle and started drinking it while he walked through to his bathroom. As soon as he started drinking, a small urge to pee hit him and he let it out immediately, as he had been doing for quite a while now. He undressed while he was drinking his bottle.
As he rediaperd himself, he was aware that for once he wasn’t going to have another suppository stuck up his backside. But the last one that Cassie had put in him had yet to do its job, so he was still worried about that situation.
He was a lot more comfortable without his girdle, and there was a lot less pressure on his chastity device. He realized that he had felt hardly any pain from it all afternoon. Was he starting to get used to it already? He really hoped so. The darn thing could really hurt. He also hoped that Mel wouldn’t wait too long to grant him some relief.
But as he started working on his makeup, he couldn’t help thinking about what he was doing, while wearing diapers, and having to wear the chastity device. The more he looked at himself applying makeup like a girl, the more the little pinpricks started to become something more painful. He tried to not think about what he was doing, but it was impossible. The more he thought about doing something girlish, the worse things got. Finally, he had to stop applying the makeup and just walk around a bit, trying to let the pain calm down. He grabbed his baby bottle to drink from while he walked around, but just putting the thing to his lips reminded him of that sissyness too, and it set the pain off all that much more. He was forced to put his bottle back down again. The damn device was taking all the fun out of everything for him. Desperately, he waited till things calmed down a bit more before he once again continued applying his makeup.
It seemed like every little sissy thing that he did was setting off the pain now. But he kept at it because there was nothing else he could do. He just kept trying desperately to control himself to limit the pain. And eventually, it worked – to a point.
With his makeup finally on, he fastened his bra around his chest then put his pantyhose on. Fortunately, neither of those actions made his pain any worse. It did kick up a bit however when he started to stuff his bra, but fortunately it didn’t last long.
He opened his closet to get his clothes. The first thing there that he noticed was the box that hadn’t been there before. The box couldn’t be missed because it was wrapped up in layer after layer of Mel’s cling wrap. The next thing that he noticed was that he couldn’t see a single pair of his male shoes. He had no doubt at all as to what was in the box. And he wasn’t very happy about it. It would mean that from now on, wherever he went, he would only have women’s shoes to wear. But then, didn’t he have the same problem with his pants now too?
When he was finally dressed, he finished his first baby bottle, then grabbed his second one. But by now, he needed to pee again. Mel’s darn tea always did that to him. Wishing he had been able to keep his diapers dryer for at least a little while longer, he allowed himself to wet again as he started on his second bottle.

Mel parked her car in her usual space in front of her apartment. She noticed that Chad was there already – as he should be. She also spotted Cassie’s car and Sandy’s too. “No time like the present,” she muttered to herself as she got out of her car. She walked up the stairs and knocked on Cassie’s door. It took a moment, but finally Cassie opened it.
“Hi Mel,” Cassie said immediately as she stood back to let her in.
“Hi Cassie,” Mel replied.
“Sandy!” Cassie yelled toward their bedroom. “Mel’s here.”
Sandy came out almost immediately.
“Hi Mel. How are you?”
“I’m fine,” Mel replied. “Cassie said you wanted to see me?”
Sandy was all smiles. “I wanted to show you something I found.” She went over by her cluttered work area and dragged a bar stool into the living room where she set it on an open piece of the floor. The stool had kind of a captain’s seat on top with arms and a backrest. It didn’t look like the swivel kind, but rather a cheaper one with fixed legs. In fact, the whole thing looked a bit shabby. Sandy stood back beaming. “Well, what do you think?”
Mel was at a loss for words. “About that?”
“Uh huh!”
“Well, I don’t really need a bar stool and it won’t go with any of my furniture.”
Sandy shook her head. “Not for you. For Sissy.”
“Oh! Well, he doesn’t have any furniture except just the one chair. But why should he need that?”
Sandy looked at her like she was crazy. Then she just shook her head. “Mel, you have no imagination!” She turned and went back to her work desk and picked up a drawing pad and bought it back for Mel to see. She turned the cover over and handed the drawing to Mel.
Mel looked at the drawing. It was certainly done well. “It’s a baby’s highch…” But that’s as far as she got before she noticed something else. She glanced from the drawing to the bar stool and back again. Then she did it again. Her mouth open wide. “This… is that!”
Sandy was all smiles now. “What do you think?”
“It’s great! Better than great! And your drawing is beautiful!”
“Thanks,” Sandy replied, pleased by Mel’s compliment. “Are you interested?”
Mel looked up from the drawing again. “Of course I am. But what will it take to make that,” she pointed at the bar stool, “look like this?” she held up the drawing.
Sandy laughed a bit. “Less than you might think. I got the stool for free from a house I’m redoing. They were throwing them away. There’s a carpenter I work with who I think can do the other modifications fairly easily. Then there’s just the matter of painting and finishing it.
“And how much will your carpenter charge?”
“For this? I wouldn’t think it would cost too much at all. The chair doesn’t really need much work and that would be the hard part. Of course, the final amount would also depend on if you want to do the finish painting yourself or not.”
“I’m not the handyman type at all. How much for everything, completely finished?”
Sandy frowned. “Well, I guess I can do the painting and finishing myself, but I’ll have to check with my carpenter for the rest first. I’ll let you know.
Mel nodded. “That’s fine. And when you see him, try to get a good price for the work… then tell him to go ahead. I’ll pay it! But let’s just try to keep this a secret from Sissy till it’s ready.”
Sandy and Cassie both giggled. “That much we can certainly do,” Sandy replied.
“So what’s new with Sissy?” Sandy asked. “Cassie told me about that thing he was wearing when she changed him earlier.”
Mel sat down and told them about the latest with Sissy. Between them and Andrea she was wishing she could get them all together for one conference and get it all over with at the same time. But she was polite about it.
“You know, of course that I’m jealous,” Sandy said when Mel had finished. “Cassie gets to play with him every day and I don’t.”
Mel shook her head, “I don’t know what to tell you. But if I can think of any way you can help, I’ll let you know.” “That would be great!” Sandy replied. “Maybe I can babysit for him sometime or something.”
Mel raised her eyebrows. “Now that might be a possibility. I just don’t know when.”
Sandy and Cassie both giggled like schoolgirls together. Mel wasn’t sure if she wanted to picture Chad in their clutches or not. Then, because Sandy seemed so interested and because she had made such and effort with the high chair, she said, “If you like, you can stop by later. I have something new I’ve been kicking around in the back of my mind for his training tonight. You can watch for a bit if you like.”
Both girls jumped at the idea and squealed with delight. Mel wasn’t sure she should have really extended the invitation, but they both were helping her – a lot she realized.

Chad was busy cutting up lettuce for the salad that Mel had requested for dinner. Just a salad she had specified. Nothing heavy or fancy. So he was almost done when she walked in. She stood looking at him for a moment. “Hello, Mistress,” he said to her through his pacifier.
She smiled. “You’re learning, but you’re still slow. We’ll work on that later. Hello Sissy. How was your day?”
Chad had to think about that for a moment. “Frustrating!” he replied. “And I was so tired all day that I had to drink too much coffee, and you can guess what that did to me!”
She came around and brushed her hand against his face. “Good baby!” she crooned.
While Mel was putting her things up, Chad laid out her meal, putting the bottle of salad dressing on the table for her along with a few other things that she might want to mix in with it. Then he fixed his own salad the way he wanted it, only with a lot less dressing since he figured he would be eating it with his hands again. His salad he put directly into the refrigerator. At least it’s something that should be cold when I eat it he thought happily.
When Mel came back, she immediately sat down to eat. She looked at everything and appeared to be pleased, but she didn’t say anything at all. Instead, she looked at Chad, then she pointed to the corner she had sent him to the night before. Chad wasn’t happy about that at all, but he went, slowly. “All the way in again!” her voice cracked behind him.
He scrunched his body even tighter into the corner and attempted to keep it there. Standing in the corner was certainly not fun. It was extremely boring. A good punishment for kids. And that was how she was treating him. But what was she punishing him for? Nothing that he could think of. And all he could do was to stand there and think.
He closed his eyes since the walls were way to close and he couldn’t see anything anyway. He stood there for a long time. Mel never saying a single word to him. He couldn’t even hear her. The only sensation he had to concentrate on was sucking on his pacifier. The one interesting moment that he had was when he realized that he had to pee and he let it out. Standing in the corner like he was with no other stimulation made the whole thing all that much more noticeable and interesting. But the sensation was gone all too soon.
He thought about his chastity device. He could still feel the pressure where it was locked around him. Less now because he wasn’t wearing the girdle, but still firmly there. He was glad it wasn’t hurting him just then.
He began shifting his weight from one leg to the other to take the weight off of them. He was glad he wasn’t wearing high heels, they would have been unbearable. The longer he stood there the more he began shifting his weight and moving his legs up and down to keep the circulation going and take the pressure off.
“Sissy! Stop fidgeting and stand still!” her voice cracked behind him. He immediately stopped moving his feet – so much.
How long was she going to take to eat anyway? He was tired of standing there. He inadvertently yawned and almost lost his pacifier, fighting against the wall to keep it in his mouth. That had been close, he realized. If Mel had seen him drop it she probably would have killed him.
He heard Mel finally getting up from the table. “Ok, Sissy. You can come and eat your own dinner now.”
He pulled himself away from the corner and blinked his eyes. It had seemed like an eternity! He glanced at the clock. Only fifteen minutes! He couldn’t believe it.
He went to the refrigerator and pulled out his salad and sat down on the floor with it, he didn’t even bother to ask for a fork, he knew better. He put his pacifier in his lap and began grabbing pieces of lettuce with his fingers.
Mel watched him grab his salad and sit down to eat it where he was supposed to. That much he had done correctly, but he had forgotten to get himself a drink. She went to the refrigerator and pulled out two bottles this time. She set them down next to him. “Both of them,” she instructed. Then she walked off to start catching up on some of the work she had brought home with her.
It was a while later before she finally heard the water running in the sink as Chad started on the dishes. She had reached a stopping point and put her work up. She went into the kitchen. He had already washed a number of used baby bottles and had them stuck in the dish drain to dry. She looked them over quickly and selected one that was perfectly clear and she thought had a wider opening than some of the others.
She took the bottle back to her desk and examined it closely, then she searched through her desk drawers till she found some thin cord that she remembered she had saved from a long time ago. Her preparations after that were simple.

Friday, November 6, 2009

The Bet - Chapter 12 (Wednesday – week 2 Part 3)

The Bet
by Karen Singer

Chapter 12 (Wednesday – week 2 Part 3)

At lunchtime, Chad again hurried out to his car and drove to the gym. The receptionist inside looked him over all too carefully again as he walked in. “Hi Sissy,” she said tauntingly.
“Hi,” he replied. “I’m here to see…”
“I know, I know,” she interrupted. She was still looking him over carefully. “Love your eye makeup,” she said.
Chad blushed. Now he knew why he should have washed it off earlier. “Look, will you please just get Cassie.”
“I’m going,” she said sassily as she sauntered off, slowly.
She came back with Cassie in tow a few minutes later and Cassie again led him back to the office. He didn’t feel quite so embarrassed walking through the room full of exercising women today as he had before, but it was still bad enough.
“Pretty eyes,” Cassie said as soon as she had closed the door behind her.
Chad blushed. “I was going to wash it off, but figured why bother – because of everything else I’m wearing.”
“You’ve got a point,” she replied. “So, you’ve been washing it off every morning?” she asked as Chad started to get undressed.
“Yeah, but it was really only some mascara. Before, you couldn’t really tell that I was wearing anything… different.”
“Well, you can certainly tell a bit more now, although to be honest, I think you’ve got a long way to go… Like your shoes by the way,” she added quickly as she saw him kicking them off. “I’m surprised they’re not heels.”
“They were Mel’s idea,” Chad said. They’re a bit too small for me. He looked up at her then, “They are a lot more comfortable than heels though.”
“Sissy, you don’t have to tell me. I’ve worn out more pairs like that than I can count. Now lay down and let’s get you changed.”
Chad laid down on his back and Cassie knelt over him and began untaping his diapers. He suddenly thought about his chastity device, did Mel tell her about it? He didn’t have to wait long to find out.
“What the hell? What the heck is that?” She reached down and grabbed it lightly. Little spikes of pain suddenly registered in Chad’s brain.
“Mel put that on me last night,” he told her. “Please… don’t pull on it. It hurts! I’m having a very hard time getting used to it.”
Cassie examined it carefully. She pulled on it gently a few times, rocking it back and forth to see it better. His penis was completely encased in the thing. And it seemed to be firmly locked in place. She squeezed as best as she could on the hard plastic. “Can you feel that?” she asked.
“Only you pulling on it,” he replied.
“Nothing else?”
“Just pain.”
She gave up touching it. “So what hurts? I can see that the thing is fairly small, but there is still plenty of room inside. You don’t fill it completely – as small as it looks.”
Chad actually blushed. “There are these spikes that dig into me painfully any time I even think about getting a little bit hard or if I try to pull it off. And they really hurt.”
Cassie bent down and examined it a bit closer. Finally she located the tiny spikes. “You mean those little things hurt so much?”
“Like you wouldn’t believe!” he replied.
Cassie sat up straighter and sighed. “Mel’s taken away all my fun.”
“Mine too.”
She laughed. “Yeah, I guess she has.”
From that point on, Cassie was all business, inserting a new suppository and replacing his wet diapers with fresh ones. Then she realized that she had forgotten his baby bottle. She reached into his bag and grabbed one. “Better drink this before you get dressed, baby.” And don’t be too slow about it.
Chad reluctantly did as he was told. He had been hoping that maybe she would have forgotten the bottle.

A little while later, as soon as Cassie had led Chad back out again, Cassie grabbed her cell phone and dialed Mel’s number, hoping that Mel might not be too busy to pick up. She got lucky.
“Hello,” Mel said into her phone.
“What the heck was that?” Cassie asked immediately.
Mel instantly smiled. She recognized Cassie’s voice and also knew instantly what she was referring to. “That’s his latest phase of training,” she replied.
“God, I couldn’t even touch the thing. And he says it hurts if I pull on it too much.”
“It’s supposed to hurt. That’s to keep him from removing it.”
“Well it looks like it works well enough. Hey, speaking of removing things. Did you know he’s been washing off his mascara in the mornings. He told me. I didn’t even know he had been wearing any.”
“Was he wearing any today?”
“Yeah, full eye makeup. And it didn’t look too bad either.”
Mel was all smiles. “Good. I figured he was probably washing it off. I’m really just surprised that he didn’t remove it today.”
“Hey, you know that that plastic thingy you put on him as taken away all my fun too. I hate to say it, but I was kind of enjoying being really mean to him by teasing him and making him all hard before I wrapped him back up in his diapers again. I know how frustrating that’s supposed to be for a guy. I hope you don’t mind.”
Mel laughed. “Mind? Not at all. In fact, I’d like you to continue if you will. Do whatever you can to stimulate him down there. He’s supposed to be learning not to get hard from it anymore.”
“Not at all?”
“God! Why?”
“Because he can’t pee when he gets hard and I need him to be able to pee at the drop of a hat. I don’t want anything to interfere with it.”
“Okay…” Cassie replied, dragging the word out. “So you want me to keep playing with him.”
“Yeah, if you can.”
Cassie sighed. “I’ll try… Oh hey… I almost forgot… Sandy wants you to stop by tonight. She has something she wants you to look at. You know, she’s very jealous of me because I get to play a bit with Sissy and she doesn’t.”
“She’s jealous?”
“Yeah, she grills me about it every night.”
“She sounds a bit like my secretary, Andrea. What’s Sandy got for me to look at?”
“I have no idea. She just phoned me about it this morning and asked me to tell you.”
“Ok, I’ll stop by after work.”

Chad yawned and stretched his arms. He immediately felt a slight need to pee again and let it out. He had gotten a large coffee with his lunch after his diaper change because he had been so tired all morning. The coffee had helped, some, but it had also helped to keep him peeing too. He realized that he didn’t really even care about that part. But now, it was getting on in the afternoon and the affects of the caffeine had defiantly worn off. He was feeling so tired again he could just lay his head down on his desk and fall asleep.
Did he dare go down to the break room and get some coffee? Break time was over for most people, but there were no real rules about going down there anytime. Most people stopped in to grab coffee all day. He stifled another yawn. Did he dare?
He rolled his chair out to the opening of his cubicle and glanced down the hallway, there weren’t many people around just then. Did he dare?
He was just about to roll back to his desk again when Robin walked out of her cubicle. “Oh… Hi,” she said to him, clearly surprised to see him there. “What’cha doin’?”
“Just looking around a bit,” he replied.
“Why?” She saw him blush a bit.
“I was kind of thinking of getting some coffee.”
“And you’re afraid to walk down there because of the way your dressed.”
“Yeah, something like that.”
“So just go! You came to work that way.”
“It’s not that easy…” He yawned again. He just couldn’t help it.
“It looks like you really need that coffee.”
“Will you get some for me?”
She looked at him for a moment before she answered. He had been stubborn and rude to her earlier. “No. You can get it yourself.”
He sighed and rolled his chair back to his desk again. Robin followed behind him into his cubicle. She pulled on his arm. “Come on. I’ll walk down with you. Will that help?”
She really wasn’t giving him much of a choice. And he did need something to keep him going for the rest of the day. Reluctantly, he let her pull him to his feet. He would have stopped at the opening to his cubicle to look around, but she dragged him right out into the hallway and just kept going, keeping a hold on his arm all the way. Chad wasn’t sure if she was helping him, or showing him off.
It was a long walk, through several hallways to the break room. Mostly, the hallways were empty, but there were a few people that they passed. Too many of whom eyed Chad closely with looks of surprise. Chad realized that the ones who seemed to react mostly to him were all women. Maybe the men weren’t really noticing him yet – he hoped.
The hallways had been carpeted, but the break room had a tile floor. As soon as they walked into the room, Chad could clearly hear the sound of Robin’s heels on the floor… and his too. There was only one other man in the break room, pouring himself a cup of coffee. The man at the coffee pot looked up briefly, then looked back down at his coffee again. As soon as it was ready, he grabbed his cup and turned around. But Chad and Robin were closer to him now. Chad saw the man’s eyes lock onto him and stare, all too closely, at every detail of the way he was dressed.
The man looked like he was about to say something, but Robin was walking up to him. “Excuse me,” she said before he had a chance to say anything about Chad, “can we get at the coffee?”
The man stepped aside and Robin walked right up to the coffee pot and picked up a cup from the stack. The man backed away toward the door, sipping at his own coffee, never taking his eyes off of Chad. Finally, he turned and left the room. Chad kept watching the doorway behind him.
“Aren’t you going to get some coffee?” Robin asked as she dumped a little creamer into hers.
Chad turned around and grabbed a cup and poured some coffee into it.
“Creamer?” Robin asked holding it out to him like there was nothing out of the ordinary going on at all.
“No thanks, I like it black,” he replied. He was about to head back to his desk, but Robin sat down at one of the tables instead. What was she doing? He couldn’t stay here. “Don’t you want to go back?” he asked.
“No, I need to get away from it once in a while. Don’t you?”
Reluctantly, he sat down with her and took another sip of his coffee. She was staring at him, not taking her eyes off of him while she sipped slowly at her drink. “What?” he finally asked.
“Nothing,” she replied. “I was just trying to imagine how you would look with a little more makeup. That’s all.”
Chad rolled his eyes. Women!
“So how come just the eyes?” she asked.
Chad’s nerves were suddenly grating. But he answered her anyway. “Because that’s all I know how to do.”
“Oh,” she answered. “I guess that kind of makes sense… in a way.”
Then she was silent again, but she still looking intently at his face. Chad kept sipping slowly at his coffee. “So why the eyes?” she suddenly asked.
“What do you mean?” “I mean, why not lipstick or foundation, or anything else? Why just the eyes?”
Chad’s nerves were starting to grate again. “Because that’s all she showed me how to do!” he answered angrily. Then he realized what he had just said. Had he said too much? Given too much away?
But Robin picked up on it instantly. “She?”
Oh God! Why couldn’t she just leave him alone? “I don’t want to talk about it!” he replied.
Robin knew she had just made a small dent. But it was only a tiny one before he had closed down again. But she wasn’t quite ready to give up yet. She sipped at her coffee for a few more moments, giving him time to settle down again. Then she asked. “So did you ask her to teach you?”
Chad just shook his head. She wasn’t going to leave anything alone! “No… Yes… well, it’s complicated.
“What’s so complicated? Either you asked her to show you how to do your makeup or you didn’t? Which?”
Chad was beside himself and almost angry with her for asking. “No, I didn’t ask her to show me how to put on makeup. It was part of something else we agreed on.”
But Chad was really getting frustrated. Too frustrated. “I said I don’t want to talk about it! Ok?”
Robin took the last sip from her coffee and stood up again. “Ok, I get it! I’m just trying to help, that’s all. I was just trying to look out for you a bit. But if you don’t want me to…”
Chad felt even more frustrated. He knew she really meant well, but women… They could be so nosy! “Look,” he replied, “I’m sorry. I didn’t mean to make you mad. But this isn’t exactly easy for me.”
“So what isn’t easy for you?” she asked.
Chad just looked at her, then he turned away and headed for the door by himself, his head hung down and looking at the floor all the way. He threw his empty cup into the trash on the way out.
Robin stood there and stared after him. She had made some progress, finally, but did she know any more than she did before? She wasn’t really sure. All she knew was that she was right, there was something major going on here, a lot more than it looked like on the surface. Knowing the only way she was ever going to learn anymore was to stick to him, she ran after him, and again put her arm through his as they walked together back to their desks.