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!”