The Bet - Chapter 20 (Thursday – week 3 Part 5 of 5)

The Bet
by Karen Singer

Chapter 20 (Thursday – week 3 Part 5 of 5)

Mel drove him back to her office where he got into his own car and followed her home. He carried his things directly up to her apartment. Then Mel sent him back to her car to get a box out of the trunk and bring it up. While he was doing that, she phoned Cassie and told her that they were finally home.
Chad had just reached the top of the steps with the box when Cassie and Sandy came out of their apartment. “Hi Sissy,” Sandy said as they followed him all the way to Mel’s apartment. “Whatcha’ got there?”
“Something for Mel,” Chad replied as he awkwardly opened the door with the box in his hands. “Mistress,” he called out, “Sandy and Cassie are here.”
Mel came out of her bedroom a moment later. “Hi girls,” she said with a big smile on her face. Then she turned toward Chad. “Set the box on my bed.”
Chad headed into her bedroom and was a little surprised to see all the women following him. He set the box on the bed for Mel and turned around, but he had to immediately move out of the way as Mel headed straight for the box.
“Are you ready for this?” she asked Cassie and Sandy with a big smile on her face. She opened the box and reached her hands into the mounds of ruffles and pulled the garment out. She quickly turned around and held it out at arms length. “Ta-daaaa,” she sang excitedly. Cassie and Sandy both began squealing while Chad’s legs suddenly felt like jello.
“Oh, it’s too much!” Sandy laughed delightedly.
“Too much is right!” Chad thought unable to take his eyes off of what he now realized was a dress – a dress from his worst – and best fantasies. Except for the pink bodice, it was all huge white ruffles. The skirt on it stood almost straight out all around – way out! He didn’t get time to think about it as Mel quickly ordered him to get undressed. She expected him to wear that thing? Yeah, of course she did. He took one last look at the “dress” and began to slowly remove his clothes. As he did so, he felt the one thing that he didn’t want to feel – the bite of the little teeth inside of his chastity device. He turned around so that, momentarily at least, he wouldn’t have to look at the dress.
All three women were watching him carefully and expectantly as he removed his clothes. He should have felt self conscious, but by now they had all seen him naked and in so many humiliating situations that their stare meant nothing to him. But the thought of the dress he was about to have to wear did. His little chastity device simply wouldn’t stop hurting him.
All too soon he had removed his shoes, shirt, and pants. Mel had him keep everything else on. She grabbed a few pairs of pantyhose from her dresser and quickly stuffed them into the cups of his girdle, instantly giving him the illusion of breasts once again. Chad saw her pull down the zipper in the back of the dress, then she held it out for him to take. As he reached for it, the pain from his chastity device increased. It had to be all those ruffles he thought. The damn thing just looked so sissyish! Almost babyish!
The ruffles felt incredibly soft against his hands. The pink bodice was all satin with a big pink bow in the front. The pain from his device increased as he carefully stepped into the dress. As he pulled it up higher on his body, his legs were caressed all the way up by the mounds and mounds of ruffles that not only were the skirt, but that supported the skirt from underneath – very soft, very full, very sensual ruffles. The smooth satin of the rest of the dress soon hugged his body as he pulled his arms through it. His arms were suddenly enclosed in their own version of the soft ruffles to just below his elbows. Mel came around behind him and zipped the dress all the way up in back. He was soon tightly hugged by the smooth pink satin – contrasting wonderfully with the soft sensual ruffles.
His chastity device was killing him now. He took one step and felt the ruffles all around him moving as the skirt bobbed up and down a bit. The pain from the device increased yet again and he reached to grab himself down there, doubling over to try to make the pain go away, but as he tried to grab it, all he got were handfuls of ruffles. There were so many ruffles under his skirt, supporting it, that he couldn’t even get his hands near the device.
“I think he likes it,” he heard Cassie remark.
“Without a doubt,” Mel replied.
“Really?” Sandy laughed, “Was there ever any doubt?” All three women broke out into peals of laughter.
Chad tried to deal with the pain of the chastity device, but nothing was working. The feel of the dress moving around him kept at him all too sensually. He knew he had to look all too ridiculous in the dress, and that made things all that much worse. Even when he tried to stand up straight and stand still with his hands down at his sides it didn’t work, because the skirt of the dress stuck out so straight that his hands wound up inside the mounds of ruffles in his skirt. That was when he realized how short the skirt really was. While it stuck out really, really far, it didn’t drop down very far at all. He had to wonder if it even covered his diapers! He had no way to see if it did.
“Put your shoes back on, Sissy,” Mel ordered.
Chad had to sit down on the floor and grab his shoes. But getting them onto his feet was a nightmare because the skirt of the dress didn’t even allow him to see his feet as he got them close enough to his body to slip them on. And buckling them was even worse. He had to keep pressing down on the mounds of skirt ruffles to get past them, but as he pressed down in one place, they just puffed up all the more all around his arms. And his chastity device was killing him! Arggghhh!!! The women all laughed through his entire ordeal of trying to get his shoes back on.
“Ok, Sissy. Model for us,” Mel ordered.
Model? What was he supposed to do? He stood up and turned all the way around, then stopped and faced them again.
“Walk back and forth, Sissy.” Mel ordered. “And swing those hips, girl.”
Chad did as he was told, heading a short way across the room, but every step he took only sent the skirt of his dress moving more and more, back and forth, and up and down. The darn thing felt incredible all around him. Embarrassingly incredible. Enough so that there were tears in his eyes now from the pain his chastity device was giving him. He could feel his cock inside of it growing harder and harder with each step that he took – despite the pain. As he turned around to walk back towards the women, the skirt of the dress swished back and forth a few times, emphasizing the feel of the ruffles all around him. He was suddenly thankful the dress didn’t come down much lower where he could feel it more against his pantyhose covered legs, it would only make the sensations all that much worse.
But the feel of the dress moving around him was more than enough for him. He let out a small whimper as he felt his cock straining against the tiny confines of the inside of his chastity device. It could grow no more. The pain from the tiny teeth felt like fire burning all around where they pressed into him. It had been a long time since he had had any relief, over a week now. A time filled with nothing but stimulation to his fantasies. Despite all the progress he had made in learning to control his erections, the darn dress foiled everything. As much as he didn’t want to get hard, the dress was giving him no choice – and his chastity device was also giving him no choice. He was caught between the proverbial rock and a hard place. Two opposing forces that wouldn’t relent. And the only result for him was pain. His knees bent together as he reached down desperately into the pile of ruffles that covered his front – a futile gesture that solved nothing.
“Oh, there’s no doubt that he likes it,” he heard Sandy saying through his pain.
“Poor guy,” Cassie added.
“What guy?” Sandy replied. All three women began laughing at him all over again.
“Come along now, Sissy,” Mel ordered. “Standing there like that isn’t going to help you any. Let’s see if maybe some work can take your mind off of your little problem.”
Chad tried his best to stand up straight again, but he didn’t quite make it. He headed out to the living room to the tune of all three women laughing at him all over again.
“Dust the furniture for us, Sissy,” Mel ordered as she followed behind him. “And make sure you do a really good job this time. And you’d better be extra careful not to mess up that dress while you’re working!”
Chad dutifully found her dust cloth and furniture polish and headed for the small table she kept by the front door. But as he got close to it, the skirt of his dress got there first. He stopped and reached out. He couldn’t even touch the table without compressing the skirt in front of him. He heard more peals of laughter from the women behind him.
He forced his way closer to the table, crushing the ruffles in front of him tighter against him. He moved some of the items on the table and then sprayed the bare wood. Then he began wiping it. But the wiping motion set the ruffles in his skirt moving all too furiously – which set off the women’s laughter all too furiously.
“More elbow grease!” Mel called from behind him.
He rubbed harder at the table which only made his skirt move all that much more. His hard-on began raging again, but he did his best to continue working despite the pain. He seriously doubted that any of the women had any idea how difficult it was for him or how much pain he was in. He finally moved on to the end table next to the couch, then to the rest of the furniture in the room.
When he finished, Mel let him put the dusting material away and he thanked her profusely. “Can I take this thing off now, please?” he asked, dropping a very serious curtsey – which only made all the women laugh again.
“No, of course not,” Mel replied. “We’re enjoying watching you in it.”
Chad felt a bit deflated, all he really wanted was to stop the endless swirling of the dress and get his chastity device to stop hurting him – or to have an orgasm which would be even better – not likely though. A sudden thought hit him. “Mistress,” he said dropping yet another curtsey, “please, I really need to get some of my laundry done tonight. May I get some of it started in the washer?”
“No, Sissy,” Mel replied. “We have company right now. Not till later.”
He understood, but he remained worried. Everything that was bothering him lately was things that he couldn’t do anything about. He’d just have to remind her later.
Mel turned to Cassie. “Any chance you can show him how to fix his hair properly now?”
Cassie smiled. “Of course, I’d love to. Let’s do it in the bathroom.” She turned to Sissy. “Do you have your curling iron and brush?”
Chad retrieved the curling iron he had bought earlier and pulled it out of the package, then he found a brush that he had never used in his purse. He wasn’t really all that happy about what he was about to learn – yet there was that tiny stimulating fascination to it too – which also didn’t help his pain.
In the bathroom, Cassie began showing him how to brush his hair properly, then pull out sections and wrap them around the curling iron. All over his head she had him pulling wide sections of hair and heating them up. When he was done, she had him brush it all again lightly, smoothing it to where it should be. As he looked at himself in the mirror, he could see how much fuller and thicker his hair looked – not to mention how much more feminine. Way more feminine. It was so embarrassing – especially since he was learning to do it for himself. He was also learning now to fight through the pain of the chastity device a little better. He noticed that the device wasn’t hurting him quite so much now too. He was just glad for anything that would ease the pain.
“Ok, Sissy,” Mel ordered, “start cleaning the kitchen now.”
Chad headed for the kitchen, all too conscious of not only his dress, but how his hair felt on his head. Parts of it tickled him as he moved now, especially the bangs across his forehead.
As Sandy watched Sissy heading for the kitchen, she said, “Mel, if you’ve got a minute, I’ve got something I’d like to show you.”
Mel was all curiosity. “Sure, Sandy. What’s up?”
Sandy giggled and pulled a piece of paper out and headed for Mel’s desk where she spread it out. Speaking softly so Sissy couldn’t hear her, she said, “this is what I’ve come up with for when he stands in the corner.”
Mel looked carefully at the drawing on her paper. “It looks like an upside down bird perch – sort of - except for the wide sides on it.
Sandy giggled. “Yeah, I guess it does, doesn’t it. But I think it will work perfectly. I’ve designed it to be narrow enough that it will be just wide enough for his feet if he keeps them together. The higher sides will keep him from moving his feet from side to side and off the ends.”
“Good idea,” Mel replied. “I didn’t think of that.”
“So shall I have my carpenter get started on it?”
“Yeah, Sandy. Definitely. Go for it!”

As Chad worked around the kitchen, the pain from his chastity device finally subsided somewhat and he was really relieved. The dress was still all too sensual, but the pain had finally dulled his ability to enjoy it the way he would have liked to. Without realizing he was going to, he suddenly felt himself peeing as he got soft enough to do it. The sensation was pure heaven and he breathed a deep sigh of pleasure.
About the time he finished wiping things down in the kitchen, Mel ushered Sandy and Cassie out the door. Chad was actually glad to see it. As soon as Mel had closed the door and turned around again, he dropped as nice a curtsey as he could and asked, “Please Mistress, can I start my laundry now?”
“No, Sissy,” Mel replied. “Not tonight. It’s getting too late.”
“But Mistress…”
“I said not tonight!”
“But…”
“I said no!”
“Mistress, I need…”
“I don’t want to hear it. Not tonight!”
“But…”
“No! Now I don’t want to have to tell you again!”
“What am I going to…”
“I said I don’t want to hear it!”
Chad reluctantly shut up. What was he going to do? He had no clean pants left for work tomorrow.
“Now let’s get you changed,” Mel said as she headed for the bathroom. Chad was ready to be changed, but he followed her reluctantly. He would have much rather done some laundry for himself.
Mel helped him out of his new dress and took it to her closet while he finished removing everything else he was wearing. Then she removed his wet diapers and cleaned him up. She inserted another suppository and put three fresh diapers on him again, followed by his plastic panties. “Let’s get you home now,” Mel said as she headed for her bedroom.
Chad followed her into her bedroom, intent on picking up his pants that he had left in there earlier, but by the time he got there, Mel already had his pants and shirt in her hand and was heading back out into the living room. “Coming?” she asked. Chad turned around and followed her. He was hoping that she would carry his clothes back to his apartment when they went, but instead she turned back into her bathroom and dumped them in her laundry hamper instead.
“What am I going to wear?” he asked.
“You can go back to your apartment just like that,” she replied as she headed for her door.
“No, I mean tomorrow? I don’t have any pants left.”
She sighed and shook her head. “You’ll just have to think of something.” Then she turned and went out her door leaving Chad to get his purse and diaper bag and follow behind her.
Chad’s mind was on one subject an only one subject – what was he going to wear to work tomorrow? He had no pants at all left in his closet. He didn’t know if Mel had planned it that way or not. It seemed like all week long they were doing one thing after another and he had never really had time to clean any of them. Now they were all in her laundry hamper and there were none left for him to even get at to wear.
He barely thought about anything else as Mel helped him into one of his onesies for the night and handed him two baby bottles to drink before he went to sleep. It was still the only subject on his mind as he laid down on his blow-up mattress and Mel turned the light off for him.
“Good night, Baby,” she said as she leaned down and softly kissed his forehead.
But Chad’s only thoughts were of the morning and having no pants to wear. What was he going to do? He put his first bottle to his lips and began drinking from it. The nipple and cool liquid felt good in his mouth, almost comforting. He greedily sucked on the bottle while he mentally fretted. And when he finished his second bottle, he continued to suck hard on the dry nipple without realizing he was doing it. Subconsciously, the action just felt good to him. He finally rolled over and put the bottle down. In the near darkness of his room, he spotted his pacifier waiting on the floor for him. He had a strong urge to pick it up and suck on it, but he stopped himself. He closed his eyes instead and tried to sleep, trying to push aside the worry that now resided in the pit of his stomach.
He suddenly felt himself wetting his diapers. The feeling was so good that for a moment he forgot all about the plight awaiting him in the morning. But the peeing never lasted long enough and all too soon he was trying to sleep again and forget his problem. Somewhere between half-sleep and completely asleep, his thumb found its way into his mouth. It stayed there all night long.

Mel’s mind was also on what Chad would wear to work tomorrow. She had planned this week carefully, and so far, everything had gone better than she expected. As far as she knew, he had no pants left. Tomorrow when he got dressed for work, he would be forced to wear a skirt. Would he do it? Of course his old pants were still in his closet, only kept away from his touch by the very flimsy cling wrap. He could always get at them if he was desperate enough. But would he actually be that desperate? Or would he get dressed for work and wear a skirt? Only time would tell.