The Bet - Chapter 35 (Friday – week 5 Part 7 of 8)

The Bet
by Karen Singer

Chapter 35 (Friday – week 5 Part 7 of 8)

Mel drove them to the same restaurant where they had eaten last week. As soon as she had parked her car, Mel once again told him to grab one of his empty baby bottles and carry it in with him – in his hand. Chad wasn’t at all happy to hear that. It was very embarrassing just to hold the thing let alone have to drink from it.
As they went inside, he was glad to see that there weren’t nearly as many people waiting as there had been last week. “Now don’t forget, Sissy,” Mel said as they walked through the door. “Just like last week. Curtsey, put your name on the list, and make sure you curtsey again when you’re done!”
Chad wasn’t thrilled to hear that. He had certainly made a fool of himself here last week. But then last week Mel had made him play a curtseying game with two little girls while they were waiting. A quick glance around at the waiting people turned up no kids at all… good! This would be bad enough! Feeling more than a bit apprehensive, he approached the waiting receptionist. He could see that she remembered him from last week. He wasn’t sure whether that was good or not. He grabbed both sides of his full skirt and pulled it wide as he dropped a curtsey to her. “How long is the wait?” he asked.
“Only a few minutes,” the receptionist replied with amusement in her eyes.
“Can you add us to your list?”
But before Chad had a chance to tell him his name, she asked, “Sissy, right?”
“Uh… Yes,” Chad replied, unhappy that she had remembered his name.
“Okay, I’ll call you as soon as your table is ready.”
“We’ll be right over there,” Chad pointed. Last week she had announced his name over their house system, even though she had been looking right at him.
“I know. I’ll let you know.”
“Uh… Thanks,” Chad replied. Then he dropped another curtsey, again spreading his skirt wider than he would have liked. He walked back to where Mel was sitting against the wall and stood near her.
“I don’t see your little playmates from last week,” Mel commented.
“No. They’re not here tonight.”
“Pity. They were delightful little girls.”
Chad didn’t exactly see it that way at all. The hostess called another party and the waiting room became a bit emptier. Right after that, Chad recognized the waitress that had served them last week coming up to the hostess’s counter. As she did so, she quickly glanced at the people still waiting to be seated. Her eyes fell on Chad and Mel and she smiled broadly. She glanced down at the waiting list then spoke to the hostess for a moment. The hostess nodded and made a notation on her list. She turned her microphone on. “Sissy, party of two.” Then she giggled. Chad wasn’t amused at all.
The waitress was still in the process of trying to grab two menus as Mel and Chad approached. “Can you change one of those menus for a child’s menu?” Mel asked.
The waitress looked back surprised, then stared at Sissy for a moment, then glanced down at the baby bottle in his hand. With a broad smile on her face she replied, “Of course.” She put one of the menu’s back and picked up a children’s menu instead.
“Do you have any crayons?” Mel asked.
Without answering, the waitress grabbed a box of crayons from a nearby container and held them up for Mel to see. “Please follow me,” she said as she turned and began leading them through the restaurant.
As they walked, Mel dug into her purse and extracted another twenty dollar bill. “Hand me your baby bottle,” she said to Sissy. As bad as it was to have to carry the thing, Chad wasn’t at all glad to get rid of it, because it meant that they he would soon have to be drinking out of it again – in the restaurant.
The waitress stopped in front of a booth and waited for them to be seated. Before Mel sat down, she handed the waitress the twenty dollar bill and the baby bottle. “And I’ll have coffee,” she said. The waitress left with a broad smile on her face.
Chad started to slide into the booth, but he quickly got back up again and grabbed his skirt to straighten it before sliding back in again. Sliding across the seat was a lot more difficult than just sitting down in a chair.
“It works better if you remember to straighten your skirt the first time you try to sit down.” Mel noted.
“Yeah, I know. Robin’s been on my case all day about it!”
The Robin woman again! Someday – soon – she was going to have to do something about her. But unfortunately, Mel realized that once again Robin was right. She had been ignoring too many of Chad’s male mannerisms. That couldn’t be allowed to go on much longer. Little things like just sitting down properly should have been addressed long ago. But that would have to happen later now, and certainly not here. It was time to delve into other things. She pointed at the children’s menu in front of him. “You might want to start getting busy with that.”
Feeling very foolish, Chad picked up the box of crayons and dumped them out on the table – four of them this time. At least he had one more color to work with than last night.
“So, who’s going to be at the poker game next week?” Mel asked.
Just being reminded of the poker game sent a cloud of worry across Chad’s face as he opened up the menu to find a decent picture to start coloring. “Besides you and me, just Derek, Ray, Steve, and George.”
“So there will be six of us? That’s a good number for poker.”
Chad shrugged. “Yeah.” He put the blue crayon to the page and began coloring in some sky.
Mel watched him for a few moments. “So what is it that you were so worried about earlier when we talked on the phone?”
Chad stopped coloring and looked straight at her. “What are you going to make me do?”
“You mean at the game?”
“Yes!”
“Like what?”
“I mean, like… While everyone else is drinking from beer bottles, are you going to make me drink from a baby bottle?” Mel didn’t get a chance to reply before he kept going. “And how about what you’re going to make me wear? Is it going to be one of those silly sissy dresses? I can just see me now, showing up in that really babyish dress with my diaper showing. I don’t think the guys would really appreciate that!”
Mel almost laughed. “They might not, but I would! You must really like those dresses if you’re so worried about it.”
“No I don’t!”
“Which really means that you do!”
Chad blushed and looked down at the page he was coloring. “Maybe,” he replied embarrassedly.
“Which means yes. What else?”
“I’ll tell you something else I don’t think the guys will appreciate, especially George.”
“What?”
“Me wearing only one diaper and then have it leaking all over his chairs.”
“Oh, I think we can find some way to deal with that too.”
It wasn’t exactly what Chad wanted to hear. “And how about my voice? This is… usually… a guys only thing. I don’t think they want to sit there all night listening to me talk like a silly idiot!”
Mel almost laughed out loud. “Oh I don’t know. I think they might get a big kick out of it.”
“No they won’t!” Chad replied sullenly as he went back to his coloring.
“But I would,” Mel replied. She watched him coloring for a few moments. “Anything else?”
Chad didn’t look up right away. “Lots of things! But I don’t want to mention them right now.” He thought of something else he did need to mention though and looked back up quickly. “Oh! And George wanted me to make sure you know how to play. He suggested I teach you a bit before the game if I have to.”
Mel looked at him and smirked. “Don’t worry. That’s not a problem. How do you think we spent all our time in the dorm rooms back in college when we weren’t studying?”
Chad just nodded and went back to his picture. Mel watched him for a few moments. “The truth is,” she said, “that I really had no idea what I’m going to do with you. I hadn’t even really considered it yet. But thanks for giving me so many good ideas!”
Chad stared at her – horrified! And then the waitress brought back his baby bottle.

Chad sat silently in Mel’s car on the way back to her apartment. He wasn’t sure if he should be glad or not that he was holding the children’s menu that he had colored. Why had Mel insisted he bring it home? She already had embarrassing pictures that he had done last night hung up on not only her refrigerator but also on his own living room wall. And all the pictures in this new book looked just as childishly colored as they had the previous night. It was impossible to color neatly while at the same time trying to constantly drink from a baby bottle. But then, he wasn’t sure if leaving the embarrassing book behind would have been any better. Would the waitress claim it as a prize of her own – and then show it off to everyone she could find? Ugh! Embarrassing! Even if he wasn’t there.
As soon as they had gotten back up to Mel’s apartment, she ordered him to prepare his punishment spot. “We might as well take care of that nasty demerit right now instead of later.”
As Mel walked off into her bedroom, Chad stood perfectly still for a few moments. He hadn’t exactly forgotten about the demerit, he had just been trying not to think about it. But trust Mel to not forget! He wasn’t looking forward to another beating, but there was no way around it… and he would probably be getting these beatings for a very long time to come since he had no intention of ever speaking in his sissy voice where anyone at work could hear him.
Almost lethargically, he grabbed a stack of disposable diapers and spread them out all over the floor where they would be needed. Then, because he knew what Mel would require of him, he began undressing, removing everything that covered him from the waist down except for his diapers. It was safer to leave those till Mel was ready.
Mel came out of her bedroom dressed casually in shorts and an old top just as he was finishing. She went straight to the corner where her yardstick was waiting and picked it up. Chad felt a twinge of fear running through his body the moment she grabbed it. Despite the number of times he had already been through this, the nervous fear continued to grow in him. Mel glanced around at the diapers that had been spread out on the floor. Good enough. “Okay, Sissy. Let’s get those diapers off of you.”
Chad stood still and let Mel rip open the tapes on each side of his diapers. She let go and they fell to the floor in a sodden heap. He suddenly felt even more exposed than ever. Slowly, as if trying to delay the inevitable, he moved into place and leaned over, putting his hands up against the back of the chair in front of him. He paused to brace himself, then forced his backside higher up into the air, making it a more inviting target for her wicked yardstick. All too soon he heard the quick swoosh of her stick as it sped through the air, but he didn’t have time to dwell on that sound as the sharp crack and pain of it hitting his backside interrupted all other thoughts. He wanted to grab his stinging backside, to rub the painful wound, but he forced himself to not touch it as he stood up. He dropped a curtsey to her. “Thank you, Mistwess,” he said in his silly sissy voice. Then he had to lean back over again, preparing himself for the next blow.
“I’m getting tired of punishing you for this,” Mel said just before she landed another stinging swat.
As Chad stood back up to curtsey and thank her, his main thought was that she couldn’t be nearly as tired of it as he was. But that didn’t mean that he was going to ever give in and let his coworkers hear him speaking like a fool. He just dared not tell her that.
As Mel watched him lean back again and prepare himself for the next blow, she said, “If we have to do this much longer, than I’m going to have to come up with an additional way to punish you!” Swish! Whap! She watched as he curtseyed and thanked her. He was starting to shake a bit now and tears were starting to form in his eyes. Good! “Speaking of additional punishments,” she said as he leaned back over again. “I hope I don’t have to give you five more swats again for not peeing during this!” Swish! Whap!
Chad was just registering her comment when the blow from her stick struck him. He realized that he hadn’t been trying to pee during the punishment yet. Another five blows would not be fun… he knew from previous experience! As he stood back up, he relaxed all his bladder muscles… sort of. Instead of holding back, he was now struggling to make himself pee. He curtseyed. “Thank you, Mistress.”
Another blow, another curtsey. Then another blow, then another curtsey. But this time, as he stooped down into his curtsey, the change in the muscle position at his crotch was enough to start him peeing. It was so sudden and without warning that it startled him. He was going to say something about it, but Mel beat him to it. “Just ignore it, Sissy, and keep doing what you’re supposed to. I see it. The fact that you’re peeing shouldn’t ever interrupt whatever it is that you’re doing. For you, it’s of no consequence at all.”
Still peeing, Chad did his best to ignore it and finished his curtsey. “Thank you, Mistress,” he finished. His peeing didn’t end till he was once again leaning over the back of the chair. Swish! Whap! At least he wouldn’t have to endure an additional five more blows.
When his punishment was over, Chad, openly crying again, curtseyed and thanked her for the last time. Mel set her stick back in the corner till next time, then while Chad was still blubbering pitifully, she searched the diapers that had been spread out on the floor for the one that looked the most wet. She had him lie down right where he was and diapered him with it. “Two hours now, Sissy. Don’t disappoint me or we’ll be doing this all over again in a little while.”
“No, Mistress,” Chad blubbered, promising himself that he would again do everything he could to get his diaper leaking before her deadline expired. He got to his feet and stared down at the diapers still strewn all over the floor. Thinking about what she had just said, he asked, “Do you want me to clean these up now?”
“Do you think you’re going to have a leaky diaper two hours from now?”
Chad had no way of knowing for sure, but he certainly intended on trying. “Definitely!” he replied confidently, hoping it would be the truth.
“Then go ahead and pick them up. But keep them handy just in case.”
Chad curtseyed and said, “Yes, Mistress,” but before he began picking up the diapers, he hurried to the kitchen and grabbed himself a baby bottle full of her awful green tea. He had a deadline to meet!