The Bet - Chapter 39 (Tuesday – week 6 Part 4 of 8)

The Bet
by Karen Singer

Chapter 39 (Tuesday – week 6 Part 4 of 8)

Mel’s phone rang before she got all the way home. She had been delayed slightly, but not too long. As she suspected, it was Sissy calling. “Hello, Sissy.”
“Hewwo Mistwess,” he replied in his sissy voice. “I’m just putting my diaper on now.”
Mel checked the clock in her car to note the time. “Good. Remember, an hour and forty-five! And if you’re late, then you’ll make us both late for your poker game – and you know I won’t be happy about that!”
Chad understood all too well. “Yes, Mistress,” he replied once again.
“Put your uniform on for now. We’ll find you something more appropriate to wear later. Oh, and Sissy, make sure you bring your pink patent heels with you.”
The pink patent heels! The ones she had bought him just to go with the sissy baby dress! Chad could almost feel the silly pink dress on him already – especially now that he was once again taped into only one diaper. “Yes, Mistress,” he replied again, this time with more than a bit of fear in his voice. It sounded like all of his worst nightmares were about to come true!
Mel ended the call and glanced at the passenger seat of her car. There were several bags there from her shopping trip this afternoon. She was going out tonight! Actually she and Sissy were going out tonight. Despite the fact that they were going to a poker game with Sissy’s friends, she found that she was looking forward to it – it would be someplace different to go with different people to talk to. She was determined that she was going to have fun tonight – despite her damn period!
The only worry in her mind was Sissy – and making him use only his sissy voice in front of his friends. Since she had called him earlier, she knew for a fact that the beating she had given him still wasn’t acting as a deterrent – or an incentive. She’d just have to talk to him again – and probably punish him again. She just wasn’t sure she wanted to start hitting him again – even though she was sure she wouldn’t get… carried away like she did last night. The question was… how should she punish him?
A few minutes later, she opened the door to her apartment, her hands and arms completely laden with the shopping bags. No smell of anything exotic cooking reached her nose. In a way she was disappointed. But the moment Sissy came out of the kitchen and greeted her with his usual curtsey, she no longer even thought about being disappointed. She just loved seeing him doing it that much – especially in his maid’s dress. “What’s for dinner?” she asked. “I don’t smell anything.”
Chad shook his head. “You said something quick and easy, so I just fixed a big salad. Will that be okay? If not, I can fix anything for you that you like.”
Mel smiled. “I know you can… and would. But a salad is probably a good idea tonight.” She didn’t add that with the way her stomach felt, the light salad would probably be the best thing anyway.
“I have the table all set if you want to eat now. I just have to dish it out.”
“Go ahead and fix my plate. I’ll be there in a minute.” She carried all her bags into the bedroom where she dropped them all on her bed. She’d open them and go through everything after dinner. She made a quick trip to the bathroom, then headed straight for her kitchen table.
Sissy had everything set perfectly – one very nicely set place for her with her dinner and coffee already waiting. She glanced at the kitchen counter before she sat down. There was a large bowl full of salad still there where obviously he had dished her salad out of. She figured immediately that he was hoping to eat some himself for dinner. She said nothing though and sat down. “I think I can manage to eat by myself. I don’t need your help for this part. Go to your corner.”
Chad turned away from her where she couldn’t see him rolling his eyes in frustration. He grabbed his baby bottle to take one last swig before being banished to his stupid corner.
“Are you wet yet?” she asked as she saw him drinking.
“Yes, Mistress,” he replied.
“How wet?”
He shrugged. “Moderately, I guess.”
“Show me your diaper!”
The command came quickly, but it took him a moment to process it. He reached down to grab the bottom of his skirt to pull it up, but suddenly she was coming out of her seat with a very determined look on her face. “You’re not fast enough with that!” she said angrily as she hurried past him – straight for her yardstick that she kept in one of the corners of the living room. She was back a moment later.
Chad was so surprised at her reaction that he paused right where he was, still bent over and holding the hem of his skirt without pulling it up. And then she was swinging her stick sharply at his backside… just once – fortunately.
“Whenever you hear anyone give that command to you, you had better react fast! Really fast! Now let’s try it again. Drop your skirt and stand up straight.”
Chad had never even had a chance to raise his skirt, but he dropped it again and stood up.
“Now curtsey for me.” Chad did and Mel inwardly smiled. She stood there staring at him, waiting, purposely, not wanting him to know when the command was going to come. “Show me your diaper!” she said suddenly.
Chad moved as fast as he could to grab his skirt and pull it up as high as he could, totally exposing his wet diaper underneath.
Mel looked at his diaper carefully. It was wet, enough that she would normally call it a lot more than moderately wet. But in terms of leaking anytime soon, she was fairly certain that it wasn’t nearly wet enough. “Drop your skirt and grab your bottle,” she said as she set her yardstick down and headed back to her seat. By the time Chad had his bottle in his hand again, she was sitting down in front of her dinner. “Just stand there and finish that thing as fast as you can. I don’t want to see you stop drinking it for even a second.” She saw him pause as he processed the information. “What are you waiting for? Drink!” Her order was like turning on an electric switch. His bottle flew to his mouth where he started nursing – furiously. She couldn’t help but smiling to herself as she picked up her fork and took a bite of the fresh salad.
She hadn’t planned on hitting him with her yardstick at all tonight, but the one little swat she had given him on his diapered covered bottom was only to get the point across so he would learn to move faster next time. And after hitting him just the once, she knew that she was totally in control of herself. If she decided to use it on him later, then she wouldn’t go overboard like she did last night.
His bottle had been about three quarters full when he started drinking in front of her. She let him drink for a few minutes while she ate. “I guess it’s appropriate,” she said as she chewed some of her food, “that I’m sitting here, like an adult, eating like an adult… and you’re... eating like a silly baby.” She nearly laughed. “It suits you so well!” She watched him closely. He never stopped nursing on his bottle, but did she see a bit of a blush come to his face? She was sure of it. She knew that he loved it when she made little teasing comments like that. It was all part of his warped fantasies. And the funny part was that she enjoyed making them just as much.
“Show me your diaper!” she suddenly commanded as he was still drinking. She watched how shocked he was to hear the command come then, but she did notice how he hurried to grab his skirt – awkwardly with the one hand still holding the bottle – and struggle to pull it up high. She was fairly certain that his diaper looked a bit wetter than he had just a few minutes ago. Good! “Finish your bottle now.”
Chad pulled his skirt back down into place and resumed drinking. There wasn’t a lot left in his bottle – fortunately. He had been shocked by her sudden command to show his diaper but at the same time, the brief respite from having to keep sucking so furiously was welcome. Drinking from a bottle, especially trying to do it quickly, was more work than most people realized.
He felt himself suddenly peeing again just before he finished the bottle. There was only a tiny bit of notice before hand that he was going to pee - not enough notice for him to have stopped it if he tried. He realized that his body had already gone back to the pattern it had been in all weekend. He was going to be peeing all night again with no warning and no control. He only hoped that all the progress he had made in holding back while he was at work today wouldn’t get undone.
He drained his bottle and finally pulled it out of his mouth. He noticed that Mel wasn’t quite finished eating yet. He fervently hoped that she would allow him to eat some salad too instead of baby food tonight. He really wanted something to chew.
“Show me your diaper!”
The command came fast and nearly caught him off guard. He grabbed his skirt as fast as he could and pulled it high.
Mel looked at his diaper. Yes, she was sure it was wetter than before. “Okay. Get yourself another bottle and start working on it.”
Chad’s mouth was tired from drinking. Usually, he sucked on his bottle a lot less hard. He could keep that up for hours – probably. It wasn’t tiring at all. In fact it was usually relaxing. But having to drink as fast as he could… that was a different ball game. He pulled another bottle out of her refrigerator and put it to his mouth.
As he drank, he was suddenly more worried than ever about the poker game later. One diaper! An hour and forty-five minutes to make it leak! And she was already loading him up with fluids at a frantic pace! How many hours would they be there? Certainly more than an hour and a half. Was she planning on changing him right in front of his friends? He shuddered at the thought. He shuddered as he remembered the fact that all his friends – his male friends at that – were about to see him as a complete and total sissy baby. How was he going to handle that? How could he do it? He couldn’t! He just couldn’t! But… how was he going to get out of it?
Mel got up from the table as soon as her dinner was finished. Before she had taken two steps, she once again commanded him to show his diaper. She thrilled to watch him rush to do it quickly. And yes, he was looking wetter. “You can pull your skirt down again,” she told him. “Then get in your highchair. I guess we better feed you before we go out later.”
Chad climbed up into his highchair, and was happy to notice that his bottom didn’t really hurt at all this time - not like earlier this morning, the last time he had sat there. He waited patiently as Mel put his tray in place, locking him into the chair. Then she tied his bib in place. Now, the big question was, what was he going to get for dinner? He was very disappointed to see her pulling one of the pink plastic baby dishes out – along with two jars of baby food. The baby food got dumped out into two colorful blobs on the plate. But instead of carrying the plate over to him, she set it on the counter next to his bowl of salad. Chad was elated to see her pull some of the salad out and put it on the plate for him. She grabbed one of his tiny baby spoons and brought it all over to him. “Enjoy,” she said simply as she set it down in front of him. Chad immediately reached out and grabbed a piece of lettuce and stuck it in his mouth. Something to chew! Heaven!
Mel stuck his bottle down on the tray for him so he could finish it. “I’ll be in the bedroom,” she said. Make sure you finish everything. I’ll be back to check on you in a little while.”
Chad didn’t care. He happily plucked a small piece of tomato out of the salad on his plate and stuck it into his mouth – totally ignoring the piles of baby food that he would still have to eat too.
In her bedroom, Mel dumped the contents of each of the bags out on the bed and smiled. Yes, tonight was going to be an interesting night for sure! She went through all the clothes she had bought, removing all the stickers and cutting off price tags. Most of the items she stuck in her drawers. Some of them went into the closet.
The bed was clear now. Out of the closet she pulled his pink sissy baby dress. She held it up and looked at it carefully. So adorable – especially on him! She laid it out flat on the bed. She found the pair of frilly socks she had bought to go with it and laid them out on the bed too. The added socks made her feel like the dress was even more adorable. She found his pink patent leather shoes – with the very high heels – in the living room next to his purse. She grabbed them and put them with his outfit too. Perfect! As an added touch, she searched around till she found one of his pacifiers and put that out with the outfit too. Accessories were so important! She smiled as she looked at the entire ensemble she had laid out on her bed. She hoped he was going to enjoy what she had planned for him!
Now… The question was… was he ready?
She walked out to the kitchen to check on him. He was just spooning the last of the baby food into his mouth. His latest bottle wasn’t finished yet, but that would have to wait. She took his plate away from him and wiped his face and hands. She removed his bib and tray, releasing him from his highchair. The moment he was standing, she again gave the command for him to show his diaper. She thrilled to see him reacting like he did. And now there was no doubt about how wet his diaper was. It was looking soaked! Good!
She smiled at him. “Before you clean up the kitchen, I’d like you to help me pick out an outfit for tonight. I need to know what would be more appropriate for your friends.” She led the way toward her bedroom.
The minute Chad entered her room and saw his baby dress all laid out for him, along with the socks and shoes… and even his pacifier… he stopped short. He had been trying to prepare himself all day for just this. But now, actually seeing them laid out for him, a wave of total fear ran though him. But he was surprised to note that a wave of excitement ran though him as well. How was he going to manage this tonight? He couldn’t! He just couldn’t!
Mel noticed him stopping and staring at the dress she had laid out for him. Good! She continued on straight to her closet where she opened the door. “What do you think, Sissy,” she said as she reached in and pulled out a couple of items on the hangers. “I was thinking of wearing this skirt,” she held out the very short stretchy mini skirt she had found earlier this morning, “along with this top I bought today.” She held up a pink clingy top, just over top of the skirt.
Chad could hardly tear his eyes away from the horror of his sissy baby dress laid out on the bed, but he forced himself to look at what Mel was holding up. The moment he saw what she wanted to wear, he gulped. “Um… wow!” he said before he could find anything better to say. The skirt appeared to be very short and the top had what appeared to be a very low cut neckline that would probably show her breasts… make that a lot of her breasts. “Don’t you think it’s kind of… um… fancy and overdressed for a poker game?”
“I don’t know. Maybe it will give me an advantage. Maybe the guys will be so busy looking at what I’m wearing that they won’t play as well.”
Chad nodded. “There is definitely that possibility.”
Mel turned away and hung the clothes back up. “Of course,” she said as she pulled down more clothes, “I can always wear something like this.” She turned around and displayed a pair of jeans and another, not quite so “flattering” top.
Chad looked at the clothes in her hand. “Now that’s definitely more appropriate,” he replied.
Mel shook her head. “I don’t know,” she said uncertainly. “I really kind of like the other outfit better. It’s fun to get all dressed up once in a while.”
“I love the outfit too,” Chad replied. “Believe me, I do. But I just think it might be a bit much for just a simple little evening of poker with the guys.”
“But it’s because of the guys that I think I was considering it,” Mel argued.
Chad shook his head. “Go ahead and wear it if you want. I know that they’ll all… appreciate it. I just think it’s a bit more than you need.”
Mel hung the clothes in her hand back up again. “I’ll think about it,” she replied, sounding slightly disappointed. “Go on out now and clean up the kitchen. And finish that bottle!”
Chad left, but not before taking one final glance at the sissy baby dress all laid out for him. How was he going to manage this? He couldn’t! He just couldn’t!