The Bet - Chapter 30 (Sunday – week 5 Part 5 of 7)

The Bet
by Karen Singer

Chapter 30 (Sunday – week 5 Part 5 of 7)

Chad watched Sandy looking through his closet. His head was still spinning from walking around Mel’s living room for so long. He felt dull from all the countless times he had curtseyed and spoke his little greetings in his stupid high-pitched voice. At least that part was starting to get easier. He wasn’t particularly happy about Mel wanting him to use that voice, but at least she wasn’t making him speak in only baby language again.
Sandy pulled a wide multi-colored skirt off of one of the hangers. She turned around and threw it at him. “Here, put this on. That should be perfect.”
Chad turned the colorful skirt around and around and finally decided that the zipper was supposed to go in the back. He pulled it on and zipped it up easily. When he let go of it though, it settled a bit lower around his hips than he thought it should. But the skirt was fairly short so that when he looked down, he could still see his knees.
“Hmmm,” Sandy mused as she watched. “Looks like we need to fix that. It’s a bit big in the waist on you. Do you have any safety pins?”
Chad shook his head. “No, none.”
Sandy turned back toward his closet. “We’ll see if Mel has any when we go back. I’ll bet she does.” A moment later, she pulled out a simple top to go with the skirt. She threw it to Chad and watched as he put it on. She would have much rather seen him dressed like a baby again, but at least his stupid bra and waist cincher were covered now. And the skirt she chose was very full so it should be good for his curtseying practice.
Now, there was just one other thing she wanted to change. If he couldn’t be dressed as a baby, then she might as well see him struggling in some high heels! “Take those shoes off, Sissy. They’ve got to go too.”
She turned around again and started searching through his shoes. He certainly had a lot of heels for a guy. Most of them were fairly high ones too. She selected a pair of the highest ones she could find that strapped onto his foot and handed them to him. As he buckled them on, she was amused to notice that it looked like he had already had a lot of practice putting them on.
When he stood back up again she looked him over. “Good enough, Sissy. Better then you were at least. Maybe later we can do something else with your hair and makeup.”
Chad actually felt a lot better now that he was dressed. Or maybe it was the heels on his feet. Either way, he felt better, almost refreshed. He smiled to himself a bit as he followed Sandy back to Mel’s apartment.
“We’re back!” Sandy declared loudly as they walked into Mel’s apartment. “Just like you wanted, I chose something simple and easy. And see, that didn’t take any time at all.”
Mel looked Chad over as Sandy sat back down again. Yeah, he did look better. She noticed the heels he was now wearing. Not exactly practical for what he would be doing all afternoon, but that wasn’t her problem.
“His skirt’s a bit loose in the waist,” Sandy added. “Do you have any safety pins we can use on it?”
“I’m sure I’ve got a few,” Mel replied as she got up and headed for her bedroom. She came back a few minutes later with a large pin in her hand. “Come here, Sissy. Let me fix your skirt for you.”
Chad walked over to her, but all she did was to stare down at him, waiting. Letting out a big sigh, he curtseyed. “Yes, Mistress.”
“Turn around, Sissy,” she ordered. He turned his back to her. She pulled the skirt up where it belonged and pinned it tightly in the back. When she removed her hand, it stayed up where it belonged. Chad had been happier when it was loose, it was too tight now. She turned him around to face her again. “I’m waiting, Sissy!”
Ugh! “Thank you, Mistress,” he said in his sissy voice as he dropped another curtsey. One thing he noticed right away, he had been happier curtseying in his other shoes.
“I’d call that a half-hearted curtsey at best!” Sandy declared.
Chad wished with all his might that Sandy would just stay out of things!
“It wasn’t really very good,” Cassie agreed.
Sandy got up from her chair and headed for him. “May I?” she asked Mel.
Mel smiled. “Be my guest.”
“You’re not doing it very pretty,” Sandy told Chad. “Now grab the sides of your skirt as far down as you can easily reach.
With everybody watching him so closely, Chad grabbed his skirt and waited for what was to come next.
“Okay, now curtsey and hold it.”
Chad put his foot back and dropped into a curtsey.
“Spread you skirt out further.”
Chad pulled his arms open wider.
“Wider!” Sandy commanded.
Chad stretched his arms even wider.
“No, that’s not quite right,” Sandy said, half to herself, not at all happy with what she saw.
“Try having him hold his skirt up higher,” Cassie chimed in from her seat across the room.
Sandy was a bit surprised by her suggestion. “Higher? That’s not right.”
“Just try it,” Cassie replied.
“You heard her, hold it up higher.” Chad raised his arms. Sandy looked at it, but it just looked all wrong and kind of silly. “Is that what you wanted?” she asked Cassie.
Cassie was giggling in her seat. “It’s not exactly what I had in mind but close. I like it even better though because now I can see his diapers underneath.”
Suddenly Mel started giggling too. “Okay, Sissy. Curtsey again and hold your skirt as high and as wide as you can.
Chad was mentally screaming. What was wrong with the way he had always done it? It got the point across… whatever point curtseying was supposed to relay. He did as he was told though, dropping and holding his curtsey with his skirt held high and wide.
Cassie was giggling again. “Oh, that full skirt makes that look so much better. I just love it when his diaper shows underneath. He looks like such a… a… sissy when he does it like that. Although it’s not very lady-like at all!”
Mel was all smiles. That was exactly what she wanted. “Back to your practice, Sissy. And now we want to see perfect curtseys from you from now on.”
Chad wasn’t sure what to think. Curtsey like they wanted him to? Like a sissy? Okay, so maybe he was a sissy, but still! He started to turn around to begin walking around the room again, but Mel quickly reached out and grabbed him. “Are you looking to get punished?” she asked.
Damn! He had forgotten again! This was getting too complicated! He curtseyed again, as best he could, to Mel and said his “Yes, Mistress,” in his little sissy voice. Then he turned around and began walking again. Only half his thoughts though were on curtseying, the other half were on how his very high heels felt on his feet. He loved wearing heels. It was part of the fun of dressing up for him. But he could tell right away that if she kept him walking around and around again, then his heels were going to get very tiring, very fast. And the curtseying certainly wasn’t as easy in them either.
He stopped in front of the lamp again, dropped his curtsey – being very careful to spread his skirt as high and wide as they wanted, and said his little sissy greeting. Then he paused like he was supposed to.
“Smile,” when you do that!” Cassie commanded from her chair. “You look like you’re mad at the world!”
Ugh! Why couldn’t she just leave him alone? He dropped his second curtsey – trying hard to put a smile on his face despite the fact that he didn’t feel much like smiling at all, and again thanked the lampshade. Stupid! Totally stupid!
“You need to smile more!” Sandy said as he walked around the room. “Your attitude is all wrong. Act… happy!”
Happy? The next time, he addressed the lampshade, Chad did his best to put a happy smile on his face.”
“Happier!” Mel ordered. “You could sound a bit more enthusiastic too.”
Enthusiastic? Happier? They had to be kidding! They weren’t the ones who were forced to do this stuff! He didn’t ever remember ever seeing a real woman do anything like what they had him doing! Let them try this for an hour or so!
Round and round he went, each time trying to do exactly what the women wanted him to. Until finally, he was going round and they weren’t making any suggestions to him at all. Whew! This was hard!
Mel left the room and came back with a baby bottle in her hands. “You need to keep drinking,” she told him before he had even gotten to where he could curtsey for her.
He stopped, curtseyed, took the bottle, and said “Thank you, Mistress,” as he curtseyed yet again. Then he took off again around the room.
Mel was pleased. He was getting there, but there was still a long way to go. She walked over to Cassie and Sandy and whispered to both of them.
Chad put the baby bottle to his lips as he walked around the room. He was more than ready for a drink. All this walking and curtseying stuff had him tired and thirsty… not to mention having to use the sissy high-pitched voice all the time. He took a few swallows of the tea and felt the cool liquid running down his throat. Relief!
But suddenly, Sandy was standing directly in his way. What was he supposed to do? He stopped, confused. Hoping he was getting it right, he curtseyed and said, “Yes, Sandy,” in his silly sissy voice.
Sandy giggled. “I like your skirt, Sissy.”
She liked his skirt? She stopped him for that? He curtseyed again, “Thank you, Sandy.”
“Very good, Sissy. You can go now.”
He hesitated, then dropped another curtsey and thanked her yet again. She moved out of the way and he continued his walk. Geez! What was that all about? But suddenly Cassie was blocking his way now. What was going on? He stopped in front of her and curtseyed for her too.
“How are you today, Sissy?” she asked.
How was he? Stupid question! “Fine, Thank you,” he answered as he dropped yet another curtsey.
“You can go now.”
He curtseyed again, thanked her and continued his trek. He got to the lamp and once again did it for the lampshade. Then he was off on another round, sucking his bottle now for comfort. But suddenly Mel was in his way. He stopped, feeling more panicked because it was Mel. He curtseyed and said, “Yes, Mistress,” in his best sissy voice.
“Show me your diaper.”
His diaper? Now? He hadn’t hardly thought about it for a while now because he had been so busy with walking and curtseying. He realized though that his diaper was fairly wet. He reached down and pulled up his skirt a bit, exposing the bottom of his diaper.
Mel reached out and felt the front of it, although she could see perfectly well how wet it was. “Very good sissy. But time is still wasting. Better keep wetting it.”
Chad dropped another curtsey and was about to continue walking when Sandy yelled, “Wait!” Everyone looked to her. “Tell him to show you his diaper again.”
Chad fervently wished that Sandy had stayed home today. She could be such a pain!
Mel looked at Sandy quizzically, but she repeated her command to Chad. “Show me your diaper.”
Chad again pulled his skirt up exactly the way he had done it a moment before.
“He doesn’t do that very well at all for a baby!” Sandy declared.
“He doesn’t?” Mel asked.
“No. Babies and little girls don’t have any shame about showing off whatever is under their skirts. None at all. They hold them up as high as they can, quickly and proudly. They like doing it so much sometimes that you can’t get them to stop.”
“That’s true,” Mel mused. “And no matter how he’s dressed, he is still somewhat of a baby. Besides, if it’s for a diaper check, then he’s definitely doing it as a baby!” She turned to face directly at Chad, who was mentally gulping. “You heard her, from now on whenever someone tells you to show them your diapers, you lift your skirt as high as you can. And you do it quickly and gladly! Got that?”
Oh brother! Chad couldn’t believe it. It was so stupid! But he curtseyed like he was supposed to and squeaked out in his sissy voice, “Yes, Mistress.”
“Good! Now show me your diaper.”
Chad hesitated only a moment, knowing that if he didn’t do it right, they would keep after him until they were satisfied. He quickly pulled his skirt up in the front as high as he could and tried to act like he was proudly showing off his wet diaper underneath. He felt like such a fool doing it that way, not to mention like such a baby too.
“Very good,” Mel said. “You can go now.”
Around and around. Curtsey and talk. Around and around again. Over and over, one of the three women would stop him and ask him dumb questions or make some dumb remark, only to get him to curtsey to them. Occasionally one of them would ask to see his diaper. He was tired of doing it long before he had even started. He kept drinking from his almost empty baby bottle more out of habit now than anything else.
And then Cassie stopped him. Curtsey. “Yes, Cassie?”
“Show me your diaper.”
As he had done many times already, he enthusiastically pulled the front of his skirt way up and held it there. But Cassie face suddenly turned from bored to confused. “Hey Mel,” she called. “It looks like his diaper is getting awfully wet around the edges. You might want to consider changing it soon.”
“Let me see,” Mel said as she headed over to look. Chad just stood there with his skirt held high. He hadn’t felt anything running down his legs yet so he didn’t think he was leaking.
Mel looked at his diaper carefully. “Yeah, the outside of it is getting all wet around his leg openings. Why didn’t you tell me it was leaking, Sissy?”
Chad was surprised. “I didn’t know,” he replied in his silly sissy voice. “I never felt it running down my leg.”
Mel nodded as she glanced at the clock. “You’ve managed to make it leak almost twenty minutes early. Good job, Sissy. I’m proud of you.”
Chad felt very elated at her words. It was a strange thing to feel good about, but he was more than ready to take whatever he could get. He had made his diaper leak early… without much effort at all. He had been so busy that he hadn’t been thinking about it much. And now Mel felt proud of him!
“Aw, is the widdle baby aww wet?” Sandy teased as if she were talking to a real baby. “Does she need Auntie Sandy to put a fwesh didee on her?”
Cassie giggled. “Sandy stop! You sound more like a baby than he does.”
Mel laughed too. “Yeah, she does.” Then she stopped short and stared at Sandy. “That’s not right!”
“It’s not?” Sandy asked, wondering what Mel was thinking.
“No it’s not,” Cassie agreed, sounding more serious.
“It’s not at all right that you should sound more like a baby than him! Sandy, can you teach him to talk like that?” Mel asked.
Sandy was surprised. “I don’t know. It’s just something that I’ve always done with babies.”
The more Mel thought about the idea, the more she liked it. “Can you figure it out? I really want him to learn it.”
“Sandy looked really uncertain. “I don’t know what I do. I just do it.”
“Tell you what, see if you can figure something out while I change him. Okay?”
Sandy shrugged. “Sure, I guess.”
Chad wasn’t liking anything that he heard. Not at all! What they were considering would make him sound like even more of a stupid fool than he already did. And the idea scared him a bit.
“Come along, Sissy,” Mel said as she headed for his diaper bag. “Let’s get you changed.”
A few minutes later, Chad was in a fresh dry diaper with yet another two hour time limit to make it leak. Mel allowed him to get a fresh bottle to hold and drink while he was doing whatever else they came up with.
“I’ve been trying to figure out what I do,” Sandy said as soon as Chad was ready. “And I think I’ve figured out a few things we can try, but really, there are no rules to this stuff.” She looked at Chad. “God I wish you were dressed like a baby. It would make this so much easier.”
“I want him to talk like this all the time,” Mel said, “not just when he’s dressed like a baby. In fact, when he’s dressed like a baby, I’ll probably have him use the other baby talk that you’ve already taught him.”
“Oh!” Sandy exclaimed. “That’s an interesting idea. So this is going to be his… grown up language then? God, he’s going to sound like such a…” she tried vainly to search for the right word.
“A sissy?” Mel prompted.
“Yeah, that’s for sure!”
Chad was growing even more nervous. Talk like that all the time? Fat chance! But what other option did he have?
“Okay, Sissy,” Sandy said. “Let’s try to figure this thing out. The first thing we’ve got to do is to replace everything that has an ‘r’ sound with the letter ‘w’ instead. Try it.”
Chad didn’t know what to say. “And say what?” he asked.
“I don’t know. Think of words with the letter ‘r’ in them.”
Chad searched his brain. R? The word rabbit came to mind. “Rabbit?” he asked. Then he tried the new way. “Wabbit?”
“Yeah, that’s it,” Sandy said. “Perfect.”
“Wabbit!” It reminded Chad of Elmer Fudd. “I hunting wabbits,” he said, trying to sound humorous. “I’m going to get that wascally wabbit!”
“That’s it,” Sandy said excitedly while Mel and Cassie both laughed. “Just do that! It’s perfect!”
Chad shrugged. So they wanted him to talk like a high-pitched Elmer Fudd. Talk about dumb! It wouldn’t be the easiest thing in the world, but he could think of far worse.
“Okay, Sissy,” Mel said, “back to your practicing. And add this to your requirements for your sissy talk.”
Back to his practicing? She wanted him to start walking around and curtseying again? He wanted to scream! With a big sigh, he started walking around the room once again. He got to the lamp, stopped and curtseyed. “Hello, Mis…” he paused. The word had an ‘r’ in it. “Mistwess.” He said to the lampshade.
“Very good,” Mel said from across the room where they were all watching him.
“No it’s not!” Cassie interrupted. “I didn’t like the way he said the word ‘hello.’ I think that should be the same as with the ‘r’ sounds so that instead of ‘hello’ it should be more like ‘hewwo.’” She looked at Sandy and Mel both for approval.
“Definitely!” Sandy replied, looking to Mel for confirmation. “Good one, Cassie. Try it again Sissy.”
Oh brother! Now it was ‘l’ sounds too? This was going to be more difficult! He looked back at the lampshade, curtseyed again and said, “Hewwo, Mistwess.” He looked back at the women for approval.
“Yes,” Cassie declared.
“Good,” Mel agreed.
Chad just rolled his eyes, looked back at the lampshade, curtseyed again, and said, “Thank you, Mistwess.” As he stood back up, he was grateful that ‘thank you’ didn’t have any ‘r’ or ‘l’ sounds in it!
The women kept him practicing for a little while more, often stopping him to ask him different questions, forcing him to try to learn to use his new speaking requirements. He eventually got better, but it was obviously difficult for him.
Finally Mel looked at the clock and called a halt to it all. “I’m sorry, ladies, but Sissy has work to do now… that is if you ever want to eat tonight. So I need to get her busy in the kitchen.”
Chad was ever so grateful that it was all finished. He was tired of walking around the room in circles and talking stupid. He thought he sounded like a moron! And the heels on his feet weren’t helping matters either. Finally, he could relax and just make dinner – do something he actually enjoyed for a change!
“Sissy, don’t forget, you’ve only got about half an hour for that diaper!”
Damn! Didn’t it ever end? “Yes, Mistress,” he replied.
“Do it right!” Mel yelled quickly.
Did she mean for him to keep talking silly? Not to mention curtseying? He dropped another curtsey, being careful to spread his skirt like he did before… knowing that it probably showed his diaper underneath, and said, “Yes, Mistwess.” Damn! This wasn’t easy!
“Remember, Sissy, you never speak with curtseying… anytime! And I never want to hear anything except your new sissy voice. And that means either baby talk like Sandy taught you, or your new sissy talk. Never anything else! Period!
Chad wanted to cry. Did she really mean always? That would be almost impossible. “Yes, Mistwess,” he said rather forlornly as he dropped yet another curtsey.