Friday, May 28, 2010

The Bet - Chapter 24 (Monday – week 4 Part 1 of 5)

The Bet
by Karen Singer

Chapter 24 (Monday – week 4 Part 1 of 5)

Her dreams were fuzzy… mixed up… colliding. She was successful – she wasn’t successful. She had everything – she had nothing. She was loved – she was scorned. None of her dreams made sense. None of her dreams were fulfilling. And when her alarm clock woke her up, that’s exactly how she felt – unfulfilled. Not to mention feeling cotton headed and having a bad taste in her mouth once again from the wine the night before. Ugh!
She rolled out of bed and turned her alarm clock off. She found the courage to grab her robe and went directly into the bathroom to brush her teeth. Better… somewhat. She went into her kitchen to start the coffee and stared at the machine for a few moments before she actually did anything with it. Why did she feel so lousy? Must have been the wine last night. No, it wasn’t that she really felt lousy, well, she did, but it was more than that, she felt a bit depressed. Why?
She stood there and watched the coffee dripping down into the pot. When it finished, she took a mug and filled it. She took a sip. Mmmm. Liquid. Hot and wet. She took another sip and headed into her living room to curl up into a chair and enjoy her drink. Why should she be depressed? There was no reason. None at all. And if there was no reason, why was she dwelling on it? Dumb!
She thought about Sissy. He had been so good last night – again. She thought again about the way he had told her last night that her body was beautiful – while blindfolded. Just thinking about it sent warm fuzzy waves through her. She smiled. He could be so nice.
He had brought her to orgasm after orgasm again last night. But was it her imagination, or did he seem to be colder about it this time… just going through the motions? She wasn’t sure. But he had told her she was beautiful. And he had never even seen her body naked. Never.
She smiled again as she took another sip of her coffee. If only he were someone else. If only he were a real man instead of… whatever it was that he was. She supposed that the word “sissy” really summed it all up for him. He was a damn sissy! And as such, he craved… no, he really deserved… everything she was doing to him. Damn him! Why couldn’t he have been… normal!

Chad stared up at his blank white ceiling. His alarm clock hadn’t gone off yet. The morning dawn was just now starting to send tiny tendrils of light around the shades at his windows. It was Monday. Another day. A work day. It would be another day of humiliation for sure. Just like all the rest of his days. Ugh!
His pink alarm clock suddenly began blaring loud rock music into his room and he forced himself up off of his blow-up mattress to turn it off. Blessed silence. It felt like a relief.
His whole body felt weighted down. The bra and breast forms that were stuck to his chest felt heavy. His overly bloated diapers felt heavy, and wet, and messy… and warm, and sensuous, and wonderful. Oh how he wished he didn’t have that miserable chastity device locked onto him! Oh how wonderful it would feel to finally be able to get hard again. And if he could get hard… oh what he would do! He thought about that for a moment. What would he do? He needed relief, that was for sure! But he didn’t want to just shoot his load and be done with it all at once. A need as great as his deserved to be acknowledged… savored… used… rewarded. What would he do if he had the freedom to get hard and get the relief he so craved? Damn. His brain couldn’t even begin to wrap itself around that question. He smiled. But it sure would be fun to think about all day.
He slowly waddled his way into the kitchen to see if she had left him a note. He was glad to see that she had.


First bottle.
Get cleaned up.
Second bottle.
Get dressed. No waist cincher or bra, but wear one of your new girdles. You know the rest.
Third bottle.

That was it. Nothing really out of the ordinary. He was glad he didn’t have to wear one of the waist cinchers, but those new girdles… They were a size smaller than his old ones and he had no doubt that just getting one of the darn things on was going to be difficult.
He went to his refrigerator and pulled out one of the many baby bottles of her tea mixture and went into his living room to sit in his only chair to drink it… and to think about what he might do if he could get hard again. He felt the first tiny stings of pain from the teeth in his chastity device, yet he couldn’t stop examining his interesting question of the day. When his bottle was finally empty, he was ever so glad to realize that the stings from the chastity device had never gotten any worse… they hadn’t gotten any better either, but at least they hadn’t gotten any worse. His only real problem was, that he had never come up with any decent ideas – none at all. Troubling!

Mel dressed in one of her more conservative suits. One that she thought made her look more professional than some of her others. She would be spending a lot of time in court today and this judge seemed to be overly interested in professionalism. Well, she could certainly show him that. What she wasn’t sure was how this case would come out. But she would do her best.
As she looked at herself in the mirror, she once again remembered Sissy telling her that he knew she was beautiful. What would he think about her when he saw her wearing this suit? Would he care? He was a sissy after all. Maybe he didn’t care. But deep down, she had a feeling that he did care… she hoped anyway.

Chad struggled to pull his girdle up his body. The task was made all that much more difficult because of the extreme nails on his fingers, he couldn’t grab anything the way he really needed to. But he persevered because he had to. He finally got the thing up and over the breast forms that were stuck to his chest, then he pulled the straps over his shoulders and breathed a small, quick sigh of relief… sort of… the damn girdle was way too tight! Ugh! And he’d have to wear it all day! Double ugh!
He felt how tightly it compressed his whole body – especially around the thickness of his diapers. And the straps… he had adjusted them to their longest setting, but they were still too small and the entire thing seemed to pull on him too much. It was going to be a long day – a very long day – as usual.
He turned to his closet. Finally, he could wear some pants again – even if they were women’s pants. He had worn nothing but skirts for the last three days in a row! Three horrible… humiliating… days! What a luxury it felt to pull the pants on. Except that with the new girdle, he noticed that the waist of the pants was a bit looser now than usual and the pants kept falling down to ride further down on his hips.
He selected one of his blouses to wear with the slacks. It fit tighter over his new breasts than he was used to, but it did fit.
He grabbed the low-heeled shoes he usually wore and slipped them on. Comfortable. But then he noticed that the bottom cuffs of his pants were too long because they had slipped down so far. He pulled them up, and they slipped down again. The smooth fabric of the girdle wasn’t going to let them stay all the way up. His girdle was too small… and because of it, his pants were now too big. Not quite knowing what to do about it, he took his shoes off and selected another pair with a slightly higher heel. At least his pants wouldn’t be dragging on the ground now.
He stood in front of his full length mirror for a few moments to see the overall affect of how he looked. His hair was ok. His makeup he thought was ok too. The new breasts definitely made a difference in his shape as did the tighter girdle. He thought about the waist cincher he had worn yesterday… that had really made a difference. Too much of a difference. He was just glad he didn’t have to wear the damn device today to work. The girdle was bad enough! Overall… he supposed he looked ok. From a distance – a long distance – someone might even think he was a woman. But the closer he looked, the more he saw a man underneath. Ok, maybe not a real man… a sissy. But that’s what he was… wasn’t he?
He walked back to his kitchen and grabbed his third baby bottle for the morning. The tape wrapped tightly around the top made sure that he couldn’t remove the nipple and pour it out or even drink it any way except through the nipple. He sat once again in his only chair and thought about what he would do if he could get hard. A dream. He knew it. He wanted it so badly… but what would he do? That was the question. He wasn’t coming up with any ideas at all. He only knew that he wanted… badly… to get hard!
He did know that he’d like to shove his long hard cock into something… something exciting… but what? And then what would he do? He wanted to prolong the experience, he was definitely sure of that, but if he got to shove himself into something, he had no doubt that he’d cum immediately, which was what he didn’t want. And shove his cock into what? His first thought was Mel. Yeah, that would definitely be nice. But he wasn’t fooling himself, she’d never allow that and he knew it.
He remembered making love to his wife – make that ex-wife. It really had never been all that fulfilling for him. He had gotten through their love making by fantasizing about sissy things – every single time. Their two and a half years of marriage were over now… well, it would be officially over later this week. The thought of that made him feel bad. He was a failure! Without a doubt, a failure. All because he was a damn sissy. And what could he do about it? Nothing! For that matter, what did he really want to do about it? Nothing! Nothing, except perhaps embrace his sissyness even more now that he was single again. But wasn’t that what he was doing right now with Mel? Definitely. It just wasn’t working out exactly the way he wanted it to. Things were far more difficult and humiliating than he ever believed they could be. Mel had taken everything way too far. It was this damn bet! She didn’t want to lose. He thought about it for a moment while he finished his bottle. She didn’t want to lose, but then, neither did he. He would win this bet in the end… no matter what he had to do! “Self-respect. Friends. And a life!”
He glanced at the tiny dial on his watch. It was almost time. He quickly found a plastic bag and put all his empty bottles into it to take to Mel. He checked his hair and makeup one more time, then grabbed his purse and slung his diaper bag over his shoulder. He was ready. It was time to get humiliated again.

The knock on her door came right on time. Mel opened it and smiled.
“Good morning, Mistress,” Chad said as he dropped a small curtsey.
“Good morning, Sissy,” she replied as she stood back out of the way, allowing him to enter. It had quickly become a morning routine… one that she absolutely delighted in. It was good to see what he had already become. And it was especially pleasing to see him curtsey so often. What immense fun!
She took the bag of bottles from him and examined it quickly while he put his purse and diaper bag on the floor by her table. Perfect as usual. He was standing still now, waiting for her to inspect him. She began looking him over carefully. She was mildly disappointed to see that he had worn slacks instead of a skirt, but after not being able to wear slacks for the last few days she had no doubt that he’d choose slacks today. She walked all around him. Yes, he looked good… except for one tiny thing. “Sissy! Where’s your pacifier?”
He couldn’t believe it! He had forgotten it again! “I’m sorry, Mistress, I forgot it again. I don’t believe it!”
“Go get it!” she ordered. “And quickly!”
He grabbed his keys out of his purse and made a rush back to his own apartment to get the darn thing. He stuck it into his mouth, not even thinking about not sucking on it and rushed back to her apartment. She was standing there with the door still open, waiting for him. “Sorry, Mistress,” he mumbled past the pacifier in his mouth as he reentered her apartment.
“Don’t forget it again!” she warned as she turned her back to him and headed to her kitchen. “Come along now, it’s breakfast time.”
Ugh! The last thing he wanted just then was more of the baby cereal that she fixed him every morning. Yuck! But as with everything else, what he wanted made no difference. Very quickly, he was trapped into the big highchair and was attempting to feed himself the tasteless mush that she called cereal with the tiny baby spoon. And as usual, all too much of it dripped straight off of the spoon, onto his chin, then down onto his bib. He cared, but he didn’t care. He was becoming too used to it now. It was just part of his typical humiliating morning routine.

Tuesday, May 25, 2010

The Bet - Chapter 23 (Sunday – week 4 Part 3 of 3)

The Bet
by Karen Singer

Chapter 23 (Sunday – week 4 Part 3 of 3)

Dinner was nearly ready, there was very little left to do, but Chad wasn’t about to admit that since he didn’t want to wind up in the corner again. He kept busy in the kitchen anyway. But shortly before Cassie and Sandy were due to arrive, Mel wandered into the kitchen to see how he was doing. “Are you almost finished?” she asked.
Chad looked around him. Everything was really ready, as much as he wanted it to be anyway. “Everything is going perfectly,” he replied.
“Good,” Mel said. “Can you stop for a few minutes?”
Chad looked around, then nodded. “Yes, Mistress.”
“Good. Follow me. Let’s get you changed.”
Getting into a fresh diaper for the rest of the evening sounded good to Chad, even though he was surprised at the offer, so he quickly followed her back to her bedroom where she ordered him to get undressed. He immediately went to work removing the apron that was tied around his waist. Mel pulled down the zipper of his dress so he wouldn’t have to struggle with that and eventually she stripped him of everything except his bra and his waist cincher. Then she put him into some super thick cloth diapers with fresh plastic panties on top.
Chad was about to reach for his pantyhose to put back on again but she stopped him. “Not this time,” she said. “I have something else for you to wear tonight.” Chad was instantly a bit wary.
Mel went into her closet and came out with a pair of white socks that she put onto his feet. The socks were turned down at the top and had row after row of baby blue lace stitched all around them for decoration. Chad didn’t quite know what to make of them. Why the socks? But then Mel went back to her closet, this time bringing out the new blue shoes. Chad stared at them in disbelief as he let her strap them onto his feet. They were blue Mary Jane style shoes with tiny colorful flowers on the toes. Talk about humiliating.
Mel went back to her closet one more time, stopping at the entrance to turn back toward him with a quick wicked smile. Chad suddenly inwardly gulped. He just knew she had something very humiliating in there for him to wear. It took her a moment to come back out again, but when she did, she proudly held up the baby blue dress so he could see it. She still had that same wicked smile on her face as she said, “Don’t you just love it? Isn’t it just… you?”
Chad couldn’t believe what he saw. It was yet another little-girl style party dress, only this time in blue and white. And again this one had a super full skirt and tons of lace and ruffles. The chastity device on his cock suddenly began stinging wildly again as Mel walked towards him with the dress – the dress that he couldn’t take his eyes off of.
Mel turned it around in her hands and he saw that the back was already unzipped as she held it out for him to take. Slowly and gingerly, he took it in his hands. He lowered it to the floor and stepped into the back. Slowly, he dragged it up his body. The super full skirt was awfully short and all too soon his bare legs were exposed again. The netting under the skirt wasn’t nearly as sensual as what had been under the last dress, yet its very stiffness let him know that it was always there – always fluffing out his skirt.
He put his arms into the dress as Mel walked around behind him and zipped it up. It fit very tightly around his new breasts, but not too bad. He stood still as Mel tied the white sash tightly around his waist. He took a step and heard the soft rustle of the netting under his skirt. His chastity device instantly sent him another warning. As he turned around toward Mel and felt the dress moving a fraction of a second behind him, he knew without a doubt that this was going to be another very difficult and embarrassing evening.
Mel stood back laughing as she just looked at him. He looked adorable… no wait! He needed something else! “Come with me,” she ordered as she quickly headed for her bathroom.
Chad dutifully did as he was told, although he didn’t move nearly as fast as Mel was going. At least the shoes were very comfortable… and he decided that the dress was actually comfortable too. It was just going to be impossible to work in with that huge full skirt surrounding him. And the diapers she had put on him were so thick that even dry, he was already mostly waddling. As he looked down, he realized he couldn’t see his feet at all because of the skirt. It was just as well, he didn’t want the sight of his sissy shoes to cause him any more pain from his chastity device. He was having enough trouble with that as it was.
Mel dug through her makeup stash as quickly as she could, finding the things she decided she would need. Then she grabbed a washcloth and began cleaning Sissy’s face with it. “You need something different with this outfit,” she explained, but she didn’t say anything else. Then she went to work on him.
A little while later, Chad stared at his reflection in the bathroom mirror. Mel had finished with him a few minutes ago but he was still too much in shock to leave the bathroom. His face… yes it was definitely his face – it just didn’t look like his face. The foundation she had put heavily all over him was far lighter in color, very pale. He had two very prominently red cheeks where she had put the blush almost in a circle on each cheek. His lips were bright red and somehow shaped to make them look a bit more pouting. And his eyes… He now had very, very long black eyelashes and the blue eye-shadow that she had put on him nearly matched his dress. The first impression that really crossed his mind was “a doll.” She had somehow made him look like a damn doll!
And then the doorbell rang. Damn! “Sissy, you better get that!” he heard Mel calling. Sighing, he tore his gaze from the mirror and went out to open the door and greet their guests.
“Aaaahhhh!” Sandy squealed the moment he opened the door. “Don’t you look precious!”
Chad dropped a curtsey as he said “Hello, Sandy.”
“Darling! Absolutely darling!” Cassie added as she stood looking at him too.
Chad dropped a second curtsey. “Hello, Cassie.”
Mel walked up as Chad stood out of the way, for the two women to come into the apartment. “Doesn’t she look good?” she asked.
“Fabulous!” Sandy declared, still not taking her eyes off of him. “He’s just so… precious!”
“I can tell right now that this is going to be even more fun than last week,” Cassie declared.
Mel looked at Chad. “Aren’t you supposed to be getting dinner ready?”
Chad hurried back to the kitchen. “I just love the way you can see his diapers and plastic panties under that dress!” Sandy declared as he headed away from them. Chad’s chastity device suddenly went into pain mode as he realized what Sandy had just said. Damn! His diapers showed! How much more humiliating can things get? And there was nothing he could do about it!
Chad dished the meal out onto three plates. There was plenty of extra for him, but he wasn’t at all sure that he’d get to eat any of it. He was hoping he would though. He poured the wine and told Mel that everything was ready for them. Then he stood back out of the way in the kitchen in case they wanted anything. But a few moments after the women sat down to eat, Mel looked over at him. “Where do you belong, Sissy?” Reluctantly, he headed to his corner once again.
He wasn’t sure if he could stand on that bar with the shoes he had on, but even the small heel of the shoes was enough to catch over the top of it. So he was once again thoroughly stuck there, unable to move, scrunched into his corner – boring, boring, boring! All he could hear from the women was occasional laugher and nothing else. He couldn’t put his arms all the way down at his sides because of the stiff skirt he was wearing, so he left his hands folded together in front of him – resting on the top of the skirt. Still, he couldn’t move – well, he wasn’t supposed to move anyway.

Oh, this is another good dish,” Cassie declared about the food they were eating. “He really is a dream. Isn’t he?”
“That he is!” Mel agreed.
“I just wish I could see him better while we’re eating,” Sandy complained. He’s too far away to really appreciate.
Mel looked at her for a moment then stared back at Sissy. Finally, she had an idea. “Sissy,” she called. “Come here.”
Chad was startled to hear Mel calling him – already. Did he do something wrong? He quickly got himself out of the corner and went back to her table. “Yes, Mistress?” he asked as he dropped a small curtsey.
Mel looked over at Sandy with a bit of a mischievous look in her eye, then she looked back at Chad. “Sissy, go get your perch out of the corner and put it right in the middle of the floor behind you.”
Chad blinked. Get his perch? Not having a choice in the matter, he did as he was told. As he picked it up out of the corner, he was surprised at how heavy the thing was. He turned it over as he carried it and saw the heads of two heavy duty steel bolts sticking up through the base. He realized it was so heavy because it was so well built. “Here, Mistress?” he asked as he set it on the floor of the kitchen.
“That’s good,” Mel said and watched as Chad set the thing down. “Now stand on it right there.”
Chad was surprised. “Here? Without any walls?”
“Right there. See if you can do it.”
Very carefully, Chad placed one foot over the bar, then the other one. He almost lost his balance for a moment, but once he found his footing he was safe enough.
“Good,” Mel declared with some satisfaction. “We couldn’t see you well enough where you were.”
Chad stood there as best he could while the women began eating and talking again, but all too soon, he saw Mel looking at him with a disapproving look on her face. “Where’s your pacifier?” she asked sternly.
Chad tried to drop a curtsey while standing on his perch and almost fell over. He heard Sandy laughing. “It’s in my purse,” he replied.
Mel got quickly up from the table and went in search of his pacifier. She was back a few moments later and shoved it forcibly into his mouth. “Much better!” she declared as she stood back to survey the difference. Both Cassie and Sandy were giggling noticeably as she sat back down to finish her dinner.
Chad had to stand there and endure all three women watching him very closely as they ate. But a few moments later, Cassie asked Mel if she could make a small adjustment on him.
Mel had no idea what Cassie had in mind but of course she agreed. Cassie got up from the table and walked over to Chad. “Your arms are all wrong,” she declared. She grabbed his left arm and had him put his elbow up against his waist, then she extended the rest of that arm out to the side and up at a slight angle. His wrist she bent down. “Do the same with your other arm now.” Chad dutifully did as he was told, feeling like a super sissy now with the limp-wristed way she had him posed.
Cassie smiled. “Much better.” She turned around and stood out of the way. “What do you think?”
Sandy was laughing. “I love it. He looks like a little Dresden doll.”
“You mean a big Dresden doll,” Mel corrected her as they all laughed.
Chad had no choice but to stand there in his super sissy pose while the women continued eating and enjoying more wine and conversation. His arms got tired but he did his best to keep them where they should be. His feet and legs ached from standing on the bar too, but his damn perch didn’t let him move his feet at all. He did feel a bit like a doll stuck standing there like that – not allowed to move.
As the women continued to drink their wine and talk, he started having more and more trouble not moving. There were no walls around him to help keep him still. Eventually, he began swaying slightly from side to side as he got more tired and his balance began to fail. He expected Mel to yell at him whenever it happened, but instead, the women laughed at him instead. He could tell they were all starting to get a bit buzzed already.
Mel sat back and took another sip of her wine. “Watch him,” she said as he swayed just a bit once again, then caught his balance and corrected his pose. “It almost looks like he’s dancing for us.” Cassie and Sandy both laughed. “Dance for us, Sissy. Can you do that? Can you stand there on that thing and dance for us?”
Chad was horrified. Dance? While standing on the bar? No way! But he tried anyway. He couldn’t move his feet, so he swayed his body ever so slightly and moved his arms around. It was all he could do. He was surprised that it felt good to be able to move his body at least that much – much better than having to stand perfectly still. But moving his body now had another unanticipated affect on him, he suddenly felt the need to pee again. Not wanting to hold back this time, he let it out while he tried to dance. It felt so good. He unconsciously closed his eyes to enjoy it and spread his knees ever so slightly. Oh wow did it feel wonderful.
“What’s he doing?” Sandy asked.
Mel giggled. “I think he’s peeing.” All three women burst into laughter.
Chad heard Mel’s comment and snapped back to reality. His face went red with shame. He hadn’t thought about them realizing what he was doing. It had just felt so darn good. He continued to try to dance while standing on the bar.
“Get off that thing now and keep dancing for us,” Mel ordered.
Chad was surprised by her order, but he was also ever so glad to get off of his perch. As quickly as he could, he got down and kept dancing, now moving more and more around the kitchen as the women watched.
Mel got up from her seat and went into the living room while he was dancing in the kitchen. A few moments later, Chad heard music coming from the living room. Not his style at all, it sounded very classical. Mel came back. “Show us what a pretty ballerina you can be again,” Mel said as she sat back down to watch him.
Ballerina? Chad realized that the music she put on must have been from some ballet. She had strange taste in music, but he wasn’t exactly in any position to argue. Once again, he did his best to imitate a ballet dancer – while the women all laughed.
“I think he needs some lessons,” he heard Cassie say at one point.
“Definitely!” Sandy agreed through her laughing.
“Maybe,” Mel replied, “but he’s funny as hell!”
Chad was trying, but he didn’t really know anything about ballet dancing – why should he? Besides, his diapers were so thick that they made moving a lot harder. And the damn dress he was wearing was impossible. He moved one way, and the skirt took a few seconds to catch up with him, then it rustled back and forth while he didn’t want it to. The result was that the damn skirt was constantly moving and he constantly felt it tickling the very tops of his legs. At least the netting didn’t feel as sensual as the last dress had, but it still was bad enough.
He was tiring now, getting very tired. So much so that he was ever so glad when Mel finally told him he could stop. “Ok, Sissy. Clean up the table now.” Chad was very glad to do some “normal” work while the women all went into the living room to talk. Mel grabbed his perch from the floor and carried it herself back to his corner. He had visions of himself standing on it once again later. He heard the music being turned down, but not off as he cleared the table.
He was loading the dishwasher when the three women came back into the kitchen again. Mel went straight to his highchair and removed the tray. “Dinner time, Sissy,” she declared. “Hop up.” Chad looked at her, then at Cassie and Sandy standing nearby. He turned the water off in the sink and quickly dried his hands before slowly waddling over to his highchair and climbing into it. He held his arms out of the way and Mel put the tray down onto the chair, semi-crushing his wild skirt in the process. At least she didn’t buckle him in. Sitting down made him all that much more conscious of his thick wet diapers – and how much he enjoyed how they felt. Bulky and lovely. If he could just get some relief! But he couldn’t dwell on them for more than a quick moment.
“Here Cassie,” Mel said as she took his bib out of a drawer and threw it onto the counter in Cassie’s direction. All too quickly, Chad had to put up with Cassie fastening the thing around his neck, making him feel even more babyish than he already did. But as Cassie finished, he saw Mel and Sandy staring into one of her cabinets, discussing what to feed him. Unfortunately, the cabinet they were standing in front of held all the baby food she had bought earlier. Yuck!
Minutes later, Sandy was giggling as she spoon fed him some kind of orange glop off of the babyish plate they had dumped it all out onto. He would much rather have been fed some of the meal he had just cooked, but obviously, that was not to be. What surprised him though, was how much Sandy seemed to be enjoying feeding him and playing all the baby games. She was really getting into it as she made choo-choo train noises or airplane noises, getting him to open his mouth so she could shove more and more of the awful tasting baby food into his mouth. She was actually being entertaining. So much so, that he hardly thought about how lousy the stuff tasted as he paid more and more attention to her babying him. And dare he think it?… He was enjoying it. It almost seemed all too soon before Cassie was wiping his face and hands with a wet cloth and Mel was taking the tray off to release him again. And once again, Mel set him to cleaning up the kitchen.

He was very surprised a short time later to hear Mel saying goodbye to her guests as he heard her ushering them out of her apartment. With Cassie and Sandy gone, Mel turned off the background music. The apartment suddenly felt quiet and almost peaceful. Chad breathed a slight sigh of relief. Hopefully, his humiliation for the day was over.
He was a bit surprised to see Mel come back into the kitchen and sit down at the table to watch him cleaning up. “We enjoyed your dancing,” she giggled as he started wiping the counters down.
He blushed a bit. “I’m afraid I’m not very good at it,” he admitted.
Mel giggled again. “No, but we enjoyed it anyway.”
Was she a bit drunk? Definitely. “I’m sure you did,” he replied as he put a bit more elbow grease into cleaning a spot on one of the counters. The skirt of his dress shook back and forth. He heard Mel laughing at him.
“Do you like your new dress?” she asked.
He stood back from the counter and looked down at himself. Did he like the dress? Just thinking about it sent a small wave of pain from his chastity device. And the skirt drove him crazy as it swished back and forth… and it didn’t even cover his diapers! Did he like it? What a question! “Yes, Mistress,” he replied with a small sigh. He looked up at her and smiled. “I love it – unfortunately.”
Mel laughed again. “You really are a sissy, aren’t you?”
One more smile to himself… one more look down at the dress he was wearing. “Yes, Mistress,” he agreed.
Mel got up from her seat. “Well then, come along Sissy. It’s time to see what else you can be good for tonight!”
Chad dropped what he was doing and dutifully followed her into her bedroom, easily guessing what she had in mind. His suspicions were confirmed fairly quickly as she pulled his dress off of him along with his new shoes and socks and then blindfolded him. He knew better than to try to remove the blindfold as he stood there listening to her moving around him. She was humming softly to herself.
Mel was slightly buzzed from all the wine, but fortunately, not too far gone. Watching Sissy all night had left her feeling a huge need for his attentions. And now the time had arrived for him to take care of those needs. She looked at him, bra and breast forms, waist cincher molding his figure, and of course his bulky diapers and plastic panties. Diapers that she could see were already soaked. She figured the wet diapers would only add to his inability to get any pleasure from what she was about to do.
She laid down on the bed, still staring at him – naked except for his diapers. “Ok, Sissy, come to me. I’m here waiting for you on the bed.”
Chad moved forward, searching with his hands till he found the bed. He climbed up and moved forward till he found her. He put his hand on her and gently massaged one of her breasts as he kneeled next to her on the bed. But he made no other move yet to do anything else. “I know why you won’t let me see you,” he said suddenly, as he continued to knead that one breast.
Mel was startled. She placed her hand over top of the hand he was touching her with, holding it in place. “You do?” She herself didn’t know that answer to that one. “Why is that, Sissy?”
His voice was almost flat. “It’s because I’m nothing but a sissy. I’m not worthy to see you naked… and I know it. But don’t think that I don’t know how beautiful you are. Because I can tell. I’ve touched you all over. I know every inch of you from touching you. You’re beautiful. All over. And I know it… Just like I know that I’m not worthy to even be near you.”
Even slightly buzzed from the wine, she was totally taken aback. He sounded so sad. Yet he was also being so honest. And his words had touched her to the core. She didn’t think she had ever been told that she was beautiful in nicer or more touching words. She got to her knees and hugged him. Then she planted a huge kiss on his lips. “Thank you, Sissy,” she said softly. “Thank you for that.”
She laid back down again like she was and grabbed that hand that had been touching her again. She pulled it back over the breast that he had been playing with earlier. She kept her own hand over top of his as she guided it round and round over that breast while she looked up into his blindfolded face. He was wrong of course… his reasons for her not wanting him to see her naked. But she couldn’t tell him that. She couldn’t tell him because she didn’t understand it herself. And part of the problem was that he was a sissy. A flake. And she wasn’t going to allow him to make love to her in any way that would be meaningful – to him. Even now, she didn’t want to tell him that she derived so much of her pleasure from denying him everything… because denying him fueled the power that she felt. The unmistakable sexual thrill of power. And she was quickly becoming addicted to it. “Love me,” she said as she suddenly pulled him down on top of her. “Love me completely.”
It was harder for Chad to feel her wonderful body under his as he laid on top of her. His huge breasts inside the bra he was wearing got in the way. The waist cincher that made it hard for him to breathe got in the way. The huge bulk of his wet diapers got in the way. And more than that, the little chastity device inside of those diapers got in the way. He was doomed to being able to just go through the motions and nothing else.
Yet he did feel her. He felt her with his hands and his arms and his legs. And later, he felt how wet and hungry her private sex spot was as his tongue brought her to orgasm after orgasm… while he remained frustrated and denied. Sexless. He hardly cared any more. Although she was enjoying herself, his efforts were at most, half-hearted. Why should he bother? He could receive nothing from any of it. He was a sissy. Unworthy to even see her naked. He understood that. He understood that it was his lot in life. Doomed forever.

And somewhere in the back of his brain, just before her final orgasm, a few remembered words seeped into his consciousness. “Self-respect. Friends. And a life!”

Friday, May 21, 2010

The Bet - Chapter 23 (Sunday – week 4 Part 2 of 3)

The Bet
by Karen Singer

Chapter 23 (Sunday – week 4 Part 2 of 3)

Chad glanced at the watch that he had struggled to fasten around his wrist. Damn, he didn’t have much time. And he still hadn’t been out for breakfast yet. Trying to get rid of his new breasts had taken way too much time. He finally decided to forget going out for breakfast, Mel would probably never know anyway.
He grabbed his grocery list that he had already put together and went over it as he drank his third bottle of the morning. He added yet a few more items that he remembered that Mel was running low on. When his bottle was finished, he put it, along with his other empty bottles from last night and this morning into a plastic bag to take with him to Mel’s apartment. He glanced at his watch again. It was almost time – close enough anyway.
With the bag of bottles in one hand, he slung his diaper bag over his shoulder, then slung his purse down into the crook of his arm. Fully loaded, he faced his front door and took another deep breath. It was time to go. Time to be her maid again. Time to face yet more humiliation. Why couldn’t he have just one day that was easy? He couldn’t remember a single day since the bet had started that had been easy for him. Not one! And now he was going out wearing a damn maid’s dress again. This would be his third day in a row without wearing pants. It still surprised him that he was actually doing it. With one more big breath for courage, he opened his door and went out.
He knocked on her door and took half a step back. As soon as the door opened he dropped a curtsey and said, “Good morning, Mistress.”
Mel smiled and let him in. “Good morning, Sissy,” she replied.
Chad dropped his diaper bag and purse on the floor next to the table near her door and handed her his bag of empty bottles. He saw her look into the bag and smile before she took put it in her kitchen for later.
“Do you have your shopping list?” she asked.
“Yes, Mistress,” he replied dropping yet another curtsey. “I’m afraid it’s a long one today. Some of the recipes I chose take a lot of ingredients.”
“That’s fine,” Mel replied only half caring as she quickly checked her hair and makeup in the mirror. She grabbed her purse to go out, then turned directly toward Sissy. She looked him over more carefully than she had before – and smiled. “You’re looking better and better,” she declared as she turned toward the door. “Time to go.”
Chad paused as he watched Mel opening the door and going out. He was dressed as a maid again and would once again be going out shopping as her maid. Would the humiliations never end? No, he knew the answer all to clearly to that question. With Mel, everything would be total humiliation. Taking a quick big breath for courage, he grabbed his purse and diaper bag and followed her down to her car.
The parking lot at the grocery store didn’t seem to be quite as crowded as it had been before, but that did nothing to ease his nervousness. He thought back to two weeks ago, the first time she had made him wear a skirt in public – she had actually called the police to get him out of the car. Now, he was not only wearing a dress, but a maid’s dress at that… and he was getting out of the car and following her inside like it was something he did everyday. Like there was nothing out of the ordinary about it at all. Mentally, he was screaming inside, but on the outside, he did his very best to look calm and confident – praying that people would see him as more of a woman than the sissy that was really inside the maid’s dress he was wearing.
As he pushed the cart around the store, Mel talked mostly about what foods she liked and also about what she liked about the dishes he had already prepared. He was grabbing item after item from the shelves and putting them into the cart while Mel put almost nothing in. Mostly, she grabbed a few snacks for herself but as far as Chad could tell, she wasn’t interested in shopping for anything else. Yet he needed so many things that their cart was filling up.

Mel felt good and relaxed as she walked with Sissy up and down the aisles of the store. It was good to be out with her maid. It made her feel good – important – powerful. She was making a man do her shopping for her, while dressed as her maid. The thrill she felt over it was electrifying. She let him do all the work, after all, he would be doing the cooking and he was the one who knew what would be needed. There were very few little things that she added to the grocery cart, mostly things that just kind of caught her fancy – that is till they got to the aisle where the baby food was. Then she stopped and looked at it all carefully.

Chad stopped and watched as Mel looked over all the baby food. His nervousness about that grew by leaps and bounds. He didn’t want her to buy any baby food, yet he now knew that she would – without a doubt. And he wasn’t the least bit surprised when she started to pick up jar after jar from the shelves and put them into the cart. She also picked up two more boxes of the baby cereal he hated to eat every morning. So much baby food in the cart. Way more than he wanted to see, yet the sight of it, knowing it was all for him, brought instant pain from his chastity device. Damn he needed some relief! It was all he could do to not show too many outward signs that he was in pain.
He watched in horror as she came across a display of baby bibs and started looking carefully though them. She pulled out a large plastic one and held it up, then with a smile, she turned and showed it to him before throwing it into the cart. Ugh! Another bib. At least this one just had pictures of farm animals on it and didn’t actually say sissy. He was so glad that Mel finally moved on.
The checkout line wasn’t bad at all, only one other person in front of them. Chad was all too aware though of the close scrutiny of all the people around him – especially while he was loading the groceries onto the conveyor belt – but there was nothing he could do about any of it. He was – in reality now – her damn maid. Her damn sissy maid. As he stood back and watched the purchases being rung up, that was the one thing that kept going through his mind. He actually was her sissy maid now. There was certainly no denying it. He was dressing the part and totally acting the part now. And he saw no way out – except eventually winning the bet. That thought reminded him of something – would Mel ask him if he needed to wet his diapers? He realized then that he had already been holding back without knowing he was. Total control. That was what was going to win the bet for him – especially since Mel knew nothing about that.
As she was about to pay for everything, Chad saw Mel turning toward him. He knew then that she was going to ask. “Do you need to wet yet?” Mel asked.
Chad desperately searched for an answer that wouldn’t get him in trouble. “No Mistress, I’m already wet,” he replied. It was a total lie. He was completely dry – for now. But Mel had no idea of the real truth. However, as he pushed the groceries out to the car, he allowed himself to thoroughly wet his diapers, reveling completely in how wonderful the sensation felt as he did it. Wet diapers were really so much better than dry ones! He should have wet them sooner – just so he could enjoy it more.

Once they were back at Mel’s apartment, Chad made trip after trip, carrying the groceries up to her apartment. The more he was out in public dressed as her maid, the more he felt like he actually was her maid. A point driven home again and again with each trip up and down the steps while wearing his maid’s dress.
He actually spent a quiet and fairly nice few hours with Mel after that. He put all the groceries up and made them each a salad for lunch – although he had to eat his with his fingers while sitting in his highchair. After which he lightly cleaned her entire apartment again – which didn’t need much cleaning and he washed what few clothes she had that were dirty. As he was doing that though, just as usual for that time of day, he once again felt the dire need to mess himself. Even though he hadn’t had any suppositories shoved up him that day, he knew that there was still enough of their chemical still in him to make it impossible to hold back so he didn’t even try. Besides what would have been the point?
But this time, he wasn’t wearing one of his girdles over top of everything and fairly soon the smell from what he had done was all too evident. He noticed it first, but there was nothing he could do about it. Mel noticed it though a few minutes later. “Sissy, it smells like you’ve got a very messy diaper!”
“Yes, Mistress,” he replied dropping a quick curtsey, then going right back to work on her laundry.
Mel got up from her seat to take a closer look. The closer she got to him though, the more she could smell him. She smiled at him as she approached, “And we didn’t even give you another suppository earlier.”
Chad stopped what he was doing. “Yeah,” he replied, “but there’s still so much of them up inside of me that it doesn’t matter. Until more of it get’s out of my system, I doubt I’ll be able to control it at all.”
Mel smiled again and lightly brushed his face. “Good baby. But then I’m sure a big sissy baby like you doesn’t really want to control it anyway.”
Chad didn’t really know how to answer that. As far as this bet went, yes he did want to control it, but otherwise…
“I’ll change you in a little while,” Mel said as she walked off again. Chad had to endure his wet messy diapers for another half-hour before Mel finally couldn’t stand the smell anymore and changed him. Then she handed him a can of air freshener and made him spray her whole apartment with it.
Chad did what he could around her apartment after that, including as much pre-preparation as he could for dinner. But eventually, he had nothing left that he could do. He approached Mel who had been sitting and reading a book. “Excuse me, Mistress,” he said dropping his usual curtsey.
She looked up, “Yes?”
“I’ve done about everything I can for now. Is there something you need me to do?”
“You’ve done everything?” she asked.
“Yes, Mistress,” he said as he dropped another curtsey without even thinking about it.
Mel smiled. She loved to see him curtsey that way to her. But he had nothing to do? That wasn’t really good, yet she suspected that just might be true. Her apartment wasn’t that big after all. “What time do you need to start dinner?”
“Probably about five,” he replied.
She nodded. “Ok, Sissy. Go stand in your corner then till I tell you to come out.”
Chad’s eyes went wide. In the corner! Why? He searched for any sign that she might not really mean it, but he quickly realized that she had really meant it. He sullenly walked over to his corner and spied the perch that was on the ground there. He turned back to her. “Do I have to…”
“Yes!” she said, already knowing what he was going to ask. “I want you standing on that thing whenever you’re in your corner – from now on!”
Dreading it even more, Chad climbed onto the darn perch. His feet were pushed close together and held at an awkward angle, as if he were wearing really high heels. He half fell into the corner with his arms dangling at his sides. He closed his eyes because there was nothing there to see. Stuck in his corner again! And once again standing on the damn bar. The stupid bar made it almost impossible to move his feet, denying him even that tiny bit of relief.
He stood there, and stood there. Boring! Boring! Boring! When he felt the need to pee, he held it for just a few minutes, but he was too bored. He let it out just for the pure joy of the sensation. Then he went back to standing there – totally bored!
He heard no sound from Mel at all and knew she was engrossed in her book. Why couldn’t he be allowed to read something instead of standing in the corner? But he wasn’t allowed to do anything except what he was doing – which was nothing! His feet ached horribly, more and more as he stood there. His legs ached more and more too. He suddenly wished he had his pacifier. He thought about putting his thumb into his mouth to suck on, but Mel wouldn’t allow him that much movement – besides, the damn long nails on his hands made sucking his thumb almost impossible anyway.
Why was she making him stand there so much? Just because there was no work to do? It was like putting him out of the way when he wasn’t needed – like a damn vacuum cleaner. Is that what she was doing? Putting him away like an appliance that she didn’t need just then. The more he thought about it, the more likely it sounded.
And then his bored mind realized something else – usually, children were made to stand in the corner for a reason – to teach them something. But he certainly wasn’t learning anything – except perhaps what a total sissy he really was. Standing in the corner like a complete child! Certainly not like the man he thought he was. He was a sissy baby, standing in the corner like a little child. Not a man at all. Not a man! A baby! A big sissy baby! He probably deserved to be treated this way. He was such a sissy. And then his chastity device started hurting him once again – damn! He probably deserved that too.

Mel looked up from her book occasionally to watch him. As far as she could tell, he hadn’t moved hardly at all since she had sent him to the corner. She wondered what he thought about as he stood there. He certainly couldn’t do anything else except to think. He had been there for a long time now – much longer than she had ever kept him there before. Yet the perch he was standing on seemed to be working perfectly. She hadn’t seen him move his feet even once – that she noticed. She really had been enjoying the book she was reading. She glanced at her clock. It still wasn’t five yet. She put her book down and went over to him. “Are you enjoying standing in your corner, Sissy?”
Chad was startled and a bit scared as he felt Mel approaching him. Would she release him? He could only hope. He was more surprised at her question. “No, Mistress. I don’t enjoy it at all.”
“Ummm. Too bad. I’ll bet you’re getting very used to it now though, aren’t you?”
Unfortunately, Chad knew the answer to that one. “Yes, Mistress.”
She laughed a bit. “Your perch is helping too. I haven’t seen you move your feet even once.”
His perch? Is that how she thought of the bar he had to stand on? He thought about her question. “I can’t move them,” he replied.
She giggled a bit once again. “Do you like how it keeps you standing there, as if you’re wearing very high heels?” she asked. “I already know you’d love for me to train you that way.”
He thought carefully for a moment before he answered. “My feet really hurt,” he finally replied.
“I’ll bet they do,” she said with yet another giggle. “Maybe I should have had you wear your highest heels today, so that when you finally get off of that thing, your feet will hardly know the difference. I’ll bet you would really like that.”
He thought briefly about what she had said, then shuddered. His feet really did ache horribly. Having to wear high heels after this would only keep them hurting. Yet at the same time, the thought did appeal to him – very much! “I’m not sure,” he finally admitted. “I think my feet hurt too much.”
“Maybe that’s just because you’re not used to it yet. Give it time, Sissy. Give it time.” She laughed again. “Ok, Sissy. You can leave your corner now. Go start dinner.”
Chad let out a huge sigh of relief and very carefully got off his perch and out of the corner. Even though he was wearing one inch heels, stretching his feet even that flat was difficult. His calf muscles ached horribly too. It took him a few moments of stretching before he felt confident enough to go into the kitchen to work.
“Get yourself another bottle while you’re fixing dinner,” Mel ordered. “You probably need it now.”
Chad thought about it and agreed. He really did need the drink!

Tuesday, May 18, 2010

The Bet - Chapter 23 (Sunday – week 4 Part 1 of 3)

The Bet
by Karen Singer

Chapter 23 (Sunday – week 4 Part 1 of 3)

Her dreams were different this time. In a way, far more serious than they had ever been before – not that she would remember any of them though. She had dreamed many times before of love, but this time it was different. This time, in her dreams, she was in the arms of the man she loved. At least she loved him. And that was why she felt so distressed in her dreams, because she knew that the one she loved didn’t return her affection.
In her dream, she writhed, over and over again, in wild turgid love sessions with her man. Yet through it all, she was aware of the coldness of his heart. She tried over and over again to show him her love – yet he still distained her. His total distain causing her to try harder and harder to win him. Yet her efforts earned her nothing but heartache.
Later in the night, her dreams became nothing but a quest for the unobtainable – the unobtainable love she yearned to feel from the man. And maybe because it was unobtainable, she was fixated on it. She had to have it. There was no way around it. She loved him desperately. She would do anything in the world for him, just to feel him loving her in return. But dream after dream ended badly, till she could take it no more.
She awoke and looked at her clock. It was a bit earlier than she wanted it to be, but not by that much. She still felt the emotions from some of her last dream slightly lingering within her. Coffee. She must need coffee. By the time she had slipped out of bed, and slipped into her robe, she had forgotten even the last lingering emotions from her dreams. Fortunately.
As she stood in front of her coffee maker and smelled the aroma of fresh coffee dripping down into the pot, she breathed in deeply and started to feel much happier. She thought about the way Sissy had made love to her the night before. It had been great – better than great – it had been fabulous! Hopefully, tonight, she would do it again with him.
But then she remembered his seeming distain of her when she had kissed him after what she had done to him. In a way, she understood it, yet in a way she couldn’t. Wasn’t everything she was doing to him part of his own demented fantasies? Why couldn’t he appreciate that? Why couldn’t he seem to appreciate anything she was doing for him? Why, why, why?
Or did he appreciate it and just didn’t show it? He had been cold during her final kiss last night – yet he hadn’t been… before. She supposed she understood why he had been so cold, yet she was very surprised that she felt hurt by it. She hadn’t even realized she felt hurt till just then. Why? Why should she care? There was no good reason for it.
She pulled a clean mug out of her cabinet and poured herself a cup of the freshly made coffee. She took a small sip. Mmmm. She closed her eyes for a moment and took another big breath. She took a bigger sip of coffee and immediately felt better. It was the coffee, nothing more. She had just needed her morning cup. She smiled as she headed out to her living room to sit in one of her big comfortable chairs… and dream about Sissy making love to her.

Strange and unfamiliar pressures bothered him, even in his sleep. He had so few comfortable ways to lay in bed, now he seemed to have even less. Fortunately, he was used to not laying on his stomach anymore because the damn chastity device she had locked onto him was too uncomfortable to lay on that way. Yet the bra he was wearing now and the breast forms inside of it were new and different… and they bothered him.
He woke up, but didn’t open his eyes. Instead, his brain was fixated on all the different sensations his entire body was feeling. The newest sensation of course was the bra and the pressure from the breast forms. He still couldn’t believe he was wearing them – even to bed. The bra felt like it was irritating his skin wherever it touched him. He couldn’t wait to get it off and take a shower. The breast forms in it were heavy too and he was tired of the constant pressure. He couldn’t wait to remove them with the bra. He wanted nothing more than to scratch his chest under it all. It would feel so good!
His pacifier was in his mouth again. He barely remembered grabbing it last night after he had finished his last bottle. He was sucking on it without really realizing he was doing it. He had barely even registered that the thing was in his mouth. Yet it felt good and comforting to have it there.
He wanted so much to make a fist with his hands, even a light one, but the nails on his fingers were so long he couldn’t even come close. He constantly felt his long nails dragging against his covers, getting in his way, even while he was sleeping. Basically, they were just irritating and a nuisance. He wished desperately that he could get rid of them. They forced him to keep moving his hands in ways he’d rather not. Ways he wasn’t used to. Ways that he knew for sure were all too feminine.
Below the bra, further down, forcing his legs to remain splayed apart, were his diapers – a huge, thick, massive ball now because he had again wet and messed himself heavily during the night. It still troubled him that he had slept soundly through it all and didn’t remember doing anything at all in them. Yet he now loved the way the huge diaper mass felt as it surrounded him and encased him. The huge bulk of his diapers was warm and very wet inside… and comforting… and stimulating.
He felt the pricks again from the new wicked teeth she had mounted in his chastity device last night. Teeth that were far worse than what had been there before. He had been surprised last night before he fell asleep how often he felt those teeth. They seemed to start hurting him long before the previous ones did anything at all. If he didn’t stay absolutely calm and even less stimulated than normal, they dug into him. Even in his normal un-stimulated state, they seemed to hurt him. His only refuge from the pain seemed to be in becoming smaller than he normally was. Smaller even than in his everyday un-stimulated state. He had no idea how he could stay that way, but the darn teeth were certainly making him try – already. It was very frustrating… well, another very frustrating thing to add to his long list of other frustrations.
The growing irritation from the teeth made him open his eyes and get up from his blow-up mattress. He had to get his mind on other things and away from anything that might sexually stimulate him. Yet everything in his entire world stimulated him now. There would be no winning. How could he stop the pain?
His pink alarm clock suddenly began blaring loud music and he quickly reached over to turn it off. Another day. Another damn day. Another day for Mel to humiliate and hurt him more than she already had. He was sick of it and wasn’t looking forward to it. Why had he entered into this damn bet in the first place?
He forced his legs to waddle his body out to the kitchen to read whatever note she had left there. He saw the cookbook on his counter before he saw the note. That figured. It was Sunday… grocery shopping day. Ugh!


First bottle.
Get cleaned up and into a fresh uniform – I will inspect as usual.
Wear a bra and one of your waist cinchers but no girdle.
Try to get the breast forms where they belong!
Second bottle.
Go get breakfast on your own.
Put together your grocery list – Cassie and Sandy will be having dinner with us tonight!
Third bottle
Be here at ten o’clock sharp!

He grunted softly. Wear a bra and a damn waist cincher. He well remembered how tight the thing had been the night before. Still a bit wooly headed, he opened his refrigerator and pulled out a baby bottle. The refrigerator that had been so empty yesterday seemed to be all too full of the bottles now. Not really caring, he grabbed the cookbook from his counter as he went past and sat in the only chair he owned. He pulled the pacifier out of his mouth and replaced it with the nipple from the bottle. The cool liquid going down his throat felt wet and refreshing. The wetness reminded him of how nice and wet his diapers felt… which stimulated his overly suppressed sexual need slightly… which in turn made his chastity device quickly start hurting again. Damn!
To get his mind off of the pain where he didn’t want any pain, he got up and found a pen and some paper to write his grocery list on. He sat back in his chair with his bottle and opened the cookbook. He flipped a few pages with his super long red nails, a task that strangely the nails seemed to be well suited for. He read through one of the recipes and awkwardly picked up the pen and paper and started writing down some of the ingredients he would need to make the dish. A lot of ingredients it seemed. No matter, Mel would be paying for them anyway. Who would have ever thought that diet cooking could be so interesting?
By the time he was done with his grocery list, his bottle was long finished. He looked over the list. It was a long one. It surprised him how quickly he was getting a lot better at writing with a pen with his long fingernails. It was all just a matter of how you held the pen… and of course getting used to holding it that way while you were writing.
He got up and put the empty bottle onto his kitchen counter along with his list and the cookbook. He picked up his pacifier and put it back into his mouth. Then he headed for his bedroom, not wanting to wait any longer to get the uncomfortable bra off of his chest!
He had less trouble than he thought unfastening the bra behind him. Maybe he was getting used to the long nails now. He really wasn’t sure about that though and mostly doubted it. Very slowly, because of the breast forms the darn thing was holding up, he pulled the bra away from his body, leaning forward slightly so the breast forms would stay in the bra cups as they came off of him. But the forms didn’t come off with the bra, they stayed right where they were on his chest. Startled a bit, he bumped one of them slightly with his arm, expecting it to pop off and land in the bra he was still holding under it. But it didn’t pop off.
He stood up straight and threw the bra onto the floor. He grabbed one of the forms. The moment he touched it, he realized that it was stuck to him fairly firmly. He grabbed it as well as the nails on his hands would allow him to, and he pulled. Then he pulled harder. Then he let go entirely as shock ran through his whole body. He grabbed the other breast form with both hands and tried to pull it off, but it too wouldn’t budge. Not a bit.
Panicking now, he began digging at the edges with his long nails. At last he had found something his nails should be really good for. But he couldn’t find any place around any of the edges that would let even the tips of his nails to get under. He stood there in shock, his body shaking from the realization. He couldn’t get the damn things off!
He didn’t know what to do. In desperation he ran for his phone and called Mel.

Mel was just about to get into her shower when she heard her phone ring. Shit! Wasn’t that always the case? She just hoped it wasn’t another emergency from work. She wasn’t really in the mood just then to run out to get somebody out of jail.
Stark naked, she picked up her phone. “Hello?”
“Mmss, ow kap paa eaa awww!”
It was Sissy’s voice she heard. She also heard how panicked he was, but she couldn’t understand anything he was saying. “Sissy? Is that you? What’s wrong?” But again she couldn’t really understand much more than she had the first time. “Sissy, are you trying to talk with your pacifier in your mouth?”
Chad was startled. He was still panicked, but he at last had the sense to remove the pacifier that had mumbled his desperate words beyond Mel’s ability to understand them. “Mistress,” he began again. “I can’t get them off… They’re stuck!”
“What are you talking about?” Mel asked, glad that she could finally make some sense form his words.
“The breast forms. They’re stuck. I can’t remove them!”
Mel blinked in surprise. Then she blinked again. They were stuck? The glue had worked? It certainly hadn’t seemed like it would hold last night. “Really?” she asked, still not believing it.
“Really?” Chad echoed in disbelief. “They’re stuck!” he shouted angrily into the phone. “I can’t budge them!”
Mel giggled. This she really had to see. “Ok,” she said, “calm down. I’ll be there in a minute.” She hung up her phone and giggled again. They were stuck on him and she guessed that he couldn’t them off. She giggled once again as she ran for her robe and wrapped it around her.

Chad opened his door carefully the moment Mel knocked, looking around the edge as he opened it to make sure it was Mel who had knocked. He also kept his body hidden behind the door till she was all the way in. Then he closed it tightly. “I can’t get them off!” he hissed angrily the moment the door was firmly shut. “Look at this.” He pulled on one of them with both hands. The breast form seemed to elongate as it stretched a bit, but it stayed firmly stuck to his chest.
Wide-eyed with disbelief, Mel put her hand over her mouth and laughed. Then she reached out with her own hands and grabbed them, pulling down on them a bit. She could see the skin around the forms pulling out just a bit and Chad was trying to pull back at the same time, but obviously, the forms were stuck on him but good. She giggled once again. “It worked!”
“What do you mean it worked?” he demanded angrily. He was now getting angry just because Mel seemed to be enjoying his predicament so much.
“The glue,” she replied. “It’s holding.”
“Yeah. Too damn well!” He pulled once again at the breast forms that were all too well stuck to his chest, but again it did no good.
“How do I get them off?” he demanded.
She giggled again. “You don’t.”
She was openly laughing now. “At least not without something to dissolve the glue first. You’re supposed to use some kind of solvent.”
“What solvent? Do you have any?”
“No,” she said as more laughter escaped her lips.
He stared at her. Damn the woman. She was really enjoying this. Damn! Damn! Damn! “So what am I supposed to do?” he demanded.
“Wear them,” she replied as more laughter escaped her lips.
Chad threw his arms up in the air in exasperation. The damn woman was loving this! He angrily waddled past her and back into his bedroom.
Mel followed after him, enjoying the sight of him too much. His diapers were so full she couldn’t believe it. Not just full, they were huge. She stood leaning against his bedroom door jam, watching him as he tried to get one of his fingernails underneath one of the forms, but obviously, he couldn’t even do that much. She let out still another giggle.
“It’s not funny,” he said angrily.
“No? I think it is,” she said as still more laughter came out. “It looks like you’re going to have to live with those things now – just like any other woman.”
The look he gave her was mean and angry. Yet she laughed at him again. “Awww,” she cooed, “is the poor little baby feeling like even less of a man?”
Once again he threw his arms up in complete exasperation. Damn the woman! He suddenly grabbed the front of his diaper as the teeth inside of his chastity device bit cruelly into his very tender flesh.
“Aw, what’s the matter baby?” she asked as she saw him dancing a bit around the room in pain. She knew very well what that something was, but she was just enjoying herself too much now.
“Did you have to put those new teeth into that thing? They hurt! They never stop hurting!”
“Good,” she replied mischievously. “I guess now you’re going to have to stay even softer and smaller than before.” She broke out laughing loudly once again. “Which should go very well with your new breasts.” Mel doubled over in laughter at her own joke. “Tell me something, am I doing a good job yet of destroying your masculinity?” Once again, she went back to her doubled over laughter.
Chad wanted to punch the walls in frustration, but of course he could no longer make a fist. Instead, he was forced to bend over and grab the front of his all too wet diapers as the pain from his chastity device instantly doubled. He cursed loudly as he danced a few steps and tried to calm the pain. The darn woman was crazy. Certifiably crazy! He finally shook his head and turned away from her so he wouldn’t have to see her laughing anymore. What was he going to do? In frustration, he reached out again with both hands and pulled on both breasts, but as usual, they weren’t going anywhere. He sighed in total disappointment. He was going to have to live with the darn things for a while… like it or not.
“I have to get a shower now,” he said with more than an ounce of annoyance, wanting her to leave.
“Don’t let me stop you,” she replied in a very mock tone. “I’ll just stay here and watch for a bit. I’m enjoying this too much to leave right now.”
Damn the woman! With a great deal of effort, Chad got his plastic panties off from around his too bulky diapers and pulled them off of his legs. As soon as he did, he found Mel right by his side, examining his bulky diapers closely. “What?” he asked, still very angry and annoyed.
“Nothing,” she replied with a small giggle. His diapers were so huge. She couldn’t believe it. She wondered how he felt having that much bulk trapped around him. But it really didn’t matter, he was stuck with the problem so she didn’t bother to ask. She was just fascinated, that was all.
She watched as he removed the diapers and made a quick bee-line for his shower. She was betting that he moved so quickly just in case he might have to pee and he didn’t want it to wind up on the floor. She giggled at that thought once again.
With nothing left to watch, she went back to her own apartment. She was still giggling at his plight as she climbed into her own shower to wash off. If there was one thing she could definitely say about this bet, it was certainly providing her with lots of amusement!

Friday, May 14, 2010

The Bet - Chapter 22 (Saturday – week 3 Part 6 of 6)

The Bet
by Karen Singer

Chapter 22 (Saturday – week 3 Part 6 of 6)

Later that evening, Chad made dinner for Mel, then had to stand on the bar in his corner while she ate. After dinner he was actually relieved to get to sit in the highchair and eat his own dinner, even if she did make him wear the bib and eat with his fingers. He was just grateful by then to get off of his feet.
While he was cleaning up the kitchen later though, Mel was busy in the bedroom. And as soon as the kitchen was spotless once again, she practically dragged him into the bedroom behind her.
Once again, Chad saw her bed heavily protected by layers of different things. But this time, Mel seemed to be all over him as she helped him undress completely down to just his diapers and bra. With each item of clothing she removed, Mel seemed to be getting more and more excited, breathing heavier and heavier. He realized what was about to come next, but had been surprised because she usually did this in the living room.
He wasn’t surprised when she brought out one of her scarves and tied it tightly around his eyes. Wrapping it several times around and making sure it was very secure. She tugged on it a few times in different directions to make sure that it couldn’t possibly come loose. Chad automatically reached for it as soon as she was done, but she slapped his hand back down. “Don’t you dare touch that,” she warned, “or I’ll tie your hands again!”
Chad was very surprised, she wasn’t tying his hands? But he chalked that up as a small miracle. He heard her moving around near him, probably undressing, but he was totally surprised to suddenly hear the commanding tone of her voice. “Hold your arms out to the side a bit,” she ordered. He dutifully did as he was told, although he had no idea why.
Mel watched him standing in the middle of her bedroom, clad in only his diapers and bra. She felt the thrill of power run through her when she told him to hold his arms out. Holding his arms out let her see his body better. And it seemed to make his diapered state all that much more apparent.
She didn’t know why, she no longer even tried to reason it out, but she still couldn’t commit herself to being seen naked by him. But sex with him, in her own way, was driving her on. The power she held over him was again thrilling her to the core. She had another idea, perhaps inspired by his new perch out in the living room. “Stand on your toes,” she commanded. She thrilled as she watched him standing on his toes now, his arms seeming to rise up a little higher too.
She finished taking her top off and wandered back over next to him. She walked around him and giggled a bit. She leaned in close to his ear. “Like a little ballerina,” she said. Even with the scarf wrapped around his head she could see the small shudder as it raced through him. She giggled again as she went back to removing her clothes. “Just stand there like that, my little sissy ballerina.”
She removed her bra and panties, so that she was totally naked, but she was still watching him, still enjoying the amazing sight of him. Still enjoying – the power! “Dance for me sissy ballerina, dance. And make sure you stay on your pretty toes – like a good sissy ballerina should.”
Chad couldn’t believe it. His toes were starting to ache and his arms were getting tired. Not really knowing what to do, he started taking tiny quick steps on his toes and spinning around in a slow circle. He moved his arms this way and that. He got bolder and took bigger steps, still on his toes. He heard Mel giggling at him. He supposed he would giggle too if he were in her place. He couldn’t imagine how ridiculous he must look. And when his feet faltered and he accidently dropped down from his toes, he expected her to yell, but she didn’t say a word. Instead he heard her humming some kind of melody that he had never heard before. He tried to dance to it.
The blindfold around his eyes hampered him somewhat and he had to be careful because he could easily lose his balance, but he still did his best. But the blindfold prevented him from seeing what was around him, and in one of his movements, his arm accidentally slammed against the post at the foot of her bed with a fairly loud bang. “Damn!” he exclaimed as he dropped down off of his toes and grabbed his arm. He shook it and flexed his hand.
“Are you ok?” she asked. There was nothing but concern in her voice.
“Yeah,” he agreed. “It just hurt a bit.”
He heard her giggle again. “Come up here on the bed with me now,” she said.
Chad carefully climbed up onto the bed. Once there, he kneeled where he was, waiting for further instructions. He couldn’t see her, but he knew she was on the bed there with him. Somewhere.
“Come over here and lay next to me,” her soft voice told him.
He carefully moved forward till his hand contacted her body, he left his hand there for a moment, feeling her. Then he carefully laid down on his side. He was more surprised when she seemed to scoot her body even closer to him.
“Make love to me,” she whispered. “Make love to me and please me as best you can.” A small quiver seemed to enter her voice. “I need to feel you doing everything you can to love me tonight.”
They were words that Chad had only dreamed he would ever hear from her. Yet the moment he realized what she was saying, he also remembered the little chastity device that was locked onto him – along with all the wet diapers he was wearing and his plastic panties. He couldn’t make love to her the way he wanted to, and he knew that she knew that. Yet despite his situation, he still wanted to touch her, to feel her, and to dream about what it was he couldn’t ever have.
He put his arm around her and held her tightly for a moment. The feel of his new breasts pressing between them felt odd to him, yet oddly erotic. He raised himself up and found her waiting lips. His kiss was filled with not only passion, but with his huge sexual need. A need so great that his body was crying inside for the relief he desperately wanted.
As he wrapped his arms and legs around her, pulling her tighter to him, moving his bare skin up and down, all around, over her bare skin, the sexual want in him rose to a completely new level. He wanted to thrust his aching cock into her so badly, yet all he could do was to think about such an act. She had totally denied him that privilege.
He felt her writhing under his touch. He slid down her body and grabbed the nipple of one of her breasts in his mouth. It wasn’t really like sucking on a bottle or his pacifier, yet he sucked hard. He felt her arching her back and heard her moan with delight. As he sucked on one breast, he massaged the other one. He heard her whimper a bit, then more, then more still.

Mel was all need. His attentions were amazing. She was feeling things she never felt before. She wanted to feel him inside of her, yet she gained even more pleasure from the power of knowing how denied he was. She needed more suddenly. She needed release. She pushed down on his shoulders, pushing his head down toward her waiting sex. She spread her legs wider and wider in anticipation. And then she felt him there. His free hands were pressing against her hips, moving up and down her sides as she felt the first tiny lick from his wonderful tongue. She wanted to cry out in ecstasy, but her muscles were too locked up under the strain of waiting for the release she yearned for. She grabbed his hair as she felt his tongue searching further and further inside of her. And then the waves of pleasure began to hit her. And when his hands made their way underneath her bottom, pressing her even tighter into him as he worked on her, her cries of pleasure could no longer be contained. She screamed with wonderful abandon.

A little while later, Chad found himself still blindfolded, but laying by himself on her bed. His face was wet with her sex. He had loved feeling her, every bit of her. It had been nice to have his hands free for once, to touch and feel her like he had never been able to do before. Yet the one part of him that longed to touch her the most was unfortunately locked away where even he couldn’t touch it. He could get no pleasure at all except the feel of her body against his. Denied. Totally denied.
He dreamed about what her body must look like. The body that he had not only touched with his hands, but now with the rest of his body too. He knew she was beautiful. He knew that she was well built. If only he wasn’t the perverted sissy that he was. If only… if only! He supposed that being the kind of person he was, he didn’t deserve to actually see her. Another small reminder of what he was… nothing but a sissy! And a sissy baby at that! Completely unworthy.

He heard her coming back again, and suddenly a wet washcloth was cleaning his face. It felt good in ways that he couldn’t describe. He was surprised when a minute later she grabbed his arm and tied it to her bed. Then his other arm, leaving him helpless once again… helpless in additional ways to the one big helplessness of his sexual need.
He felt her pulling his plastic panties down, then he felt her removing his diaper. He felt a cloth diaper quickly being put over top of his chastity device. “That’s just incase you have to wet,” she whispered. “But either way, I’ve got the bed well protected, so don’t you worry about it.”
A few minutes later, Chad felt her removing his chastity device, completely. The cool air became even cooler as she carefully cleaned him with her washcloth. Then he felt the drag of her razor as she made sure there were no hairs anywhere around. The soft diaper was placed over him again and he was left alone, waiting, helpless.
Mel carried his device out to the kitchen and cleaned it thoroughly. He had been great again. Not only great, better than ever. She wondered again why she was so reluctant to stand naked in front of him. It bothered her, yet it didn’t bother her as much as it did before. She thought again about the feel of his arms and legs as they wrapped themselves around her, as if to try to pull her completely into his own body. She realized her sex was becoming wet again from thinking about it. If she didn’t stop this line of thought she’d have to change her panties! Yet she couldn’t help it. She had loved the way he had made love to her… and at the same time, she had loved the fact that he couldn’t completely make love to her.
She carried his now clean device back to the bedroom and began putting it on him once again. This time, she made one minor, or maybe not so minor change. Instead of putting the same points of intrigue teeth into the device again, she pulled the biggest ones out of her nightstand and put them into it instead. As she pressed them into place, she saw him suddenly stiffen as they bit slightly into him. She giggled.

Chad made no protest at all, not even mentally when he felt her wrapping the base of the chastity device around him once again. He was completely expecting that, but then, suddenly the little teeth that she added to the device felt different when she pressed them into place. They felt a lot different. They were suddenly bigger and sharper. “What…” he started to say.
“Shhh!” she whispered, silencing him. “Let me finish.” He made no more protest as she continued to reassemble the device onto him, completely encasing the penis he longed to touch. And then with a very satisfying click, she lock it shut. The click of the lock was satisfying to her, but she saw him shake his head slightly in frustration.
She ran her hands tenderly over his body, then up and down his legs. She kissed his hairless chest, then she moved up and kissed him tenderly on the lips. He arched his head up to meet her, wanting the kiss as much as she did. As he laid back down again, she lightly kissed the top of his head.
She untied his hands. She whispered gently into his ear, “Roll over and get on your knees.”
Still blindfolded, Chad turned over and got onto all fours on top of her bed. He hoped he knew what was coming next. He wasn’t the least disappointed when he felt her start to rub the baby lotion all over his backside. After his frustrated love-making session a short while ago, the attention of her hands felt incredibly good. He felt her climbing up on the bed with him, then one hand rubbing his back and chest while the other hand kept working around his backside. Then her hands were gone – both of them. He wanted more, he needed more.
The feel of it was sudden, slightly cold, and definitely hard – and he arched his back and rocked backwards as she suddenly placed the tip of her vibrator up against his anus. But only the barest tip of the device went into him before she pulled it completely away again.
Mel smiled to herself as she saw him trying to move the vibrator into himself. She quickly lubed it completely with the baby lotion before she started to put it back up against him again. She put her hand on his back, then ever so slowly and gently, she brought the tip of it up against his little hole. She saw his body shudder the moment contact was made. She held it in place and ever so slowly, he began pushing himself back towards it again, trying to get more and more of it into him. And as he pushed towards her, she pushed it ever so slightly back towards him too.
Chad felt it finally going into him. He didn’t know why he liked it, he cared, but at the same time he didn’t care. It simply felt too good in his sexually repressed state. Within moments he was rocking himself back and forth against the device, forcing it to move back and forth within him. He felt her free hand start to rub his back, then move under him to rub his chest and stomach just below the bra he was wearing. He rocked faster, then faster still. But as good as it felt, there was no stimulation to the one place where he needed it the most – his all too flaccid cock. He felt the teeth from his restraint beginning to bite into him. The teeth felt different, far worse than ever before, he screamed in rage at the added pain and despite his need and continued rocking, tried to will himself to get smaller again. It worked, but only slightly. His need was still so great that he couldn’t stop rocking, despite not being able to climax.
And then he felt the faint urge to pee building within him. Peeing felt good, incredibly good. He willed himself to pee as he once again rocked faster and faster, harder and harder. The pee rushed out of him, soaking the protective towels she had placed under him, but even that sensation, as good as it felt, wasn’t enough to bring him the relief he needed so desperately. In total frustration, he collapsed his arms, letting his head drop straight down into the bed where he cried into the pee soaked towels that were under him.
Mel watched him humping himself, still not believing what she was seeing. And when she saw him peeing in the middle of it, she thrilled even more. To her, it was more proof of his total lack of control. And when he finally collapsed and started crying, she finally removed her vibrator from his backside. She put her arm around him and kissed his naked back. “Shhh,” she whispered lovingly into his ear. “Shhh.”
She rolled him onto his side, away from the soaked towels and pulled them off the bed. Then she rolled him all the way over onto his back. She had slipped her robe on earlier before she cleaned his device, but now she cinched the tie at her waist a bit tighter before she removed his blindfold. He had been crying. He was still crying a bit. She wiped his face and the tears that were on it, then she diapered him heavily again for the night.
Then, one more time, she kissed his lips, but this time, he didn’t kiss back. She stood back up, disappointed. But the truth was, she couldn’t blame him. He probably hated her guts. She couldn’t blame him for that either.
Chad had never felt so sorry for himself as he did just then. His entire life was one big stimulation on top of other big stimulations. All of it adding to his over-stimulated, over-repressed sexual needs. And he had no way to get the least bit of relief.
Almost in a daze, he let Mel hand him his things to carry home. Then she led him, clad in only his diapers, plastic panties, and bra, back to his apartment where she dressed him in his baby-doll nighty and put him to bed. She brought him two more baby bottles to drink before he could fall asleep. He never said a word to her the whole time. And when she kissed his forehead goodnight, he never once looked at her or even acknowledged her kiss. He simply felt that sorry for himself.
The cool liquid from the baby bottle that he drank felt good against his throat. The nipple in his mouth felt comfortable and soothing to suck on. He didn’t even blink as Mel turned out the light, he only stared straight up at the blank ceiling above him. Blank like him. Blank like his feelings of self-worth. Blank like his entire soul.