The Bet - Chapter 43 (Saturday – week 6 Part 2 of 8)

The Bet
by Karen Singer

Chapter 43 (Saturday – week 6 Part 2 of 8)

After five baby bottles, Chad wasn’t really all that hungry for breakfast, not that he was very interested in eating baby food anyway. Yuck! But if he didn’t get to Mel’s apartment fairly quickly, then he was going to be late – and he didn’t really want to be punished for that. Feeling sillier than ever, not to mention a bit nervous wearing nothing but one diaper and his bright pink heels, he grabbed his diaper bag and purse along with a plastic bag filled with empty baby bottles, and headed outside to walk the short distance to Mel’s apartment.
As soon as he got outside, Chad noticed one person about to climb into his car down below. The guy stopped with a startled look on his face as he stared up at him. Chad purposely tried to ignore him and did his best to not look in his direction. Things were embarrassing enough!
He rang Mel’s doorbell and waited. A moment later, she opened her door. He curtsied. “Good mowning, Mistwess,” he greeted her in his sissy voice.
Mel smiled. “Good morning, Sissy. Come on in, I’ve got your breakfast all ready.” The sight of him standing outside in nothing but a diaper and those pink heels almost made her laugh. As he walked past her she saw someone down below staring up at them. She waved to the man before she closed the door. “I see you were entertaining the neighbors.”
Chad blushed a bit. “I couldn’t help it. I tried to ignore him.”
“Why? I’m sure he would have liked to get a better look at you.”
Chad didn’t even want to contemplate such a thing.
“Your breakfast is all ready,” she said as she took the bag of empty baby bottles from him. Climb up into your highchair.” With no other clothes on, Mel had no trouble seeing how wet his diaper was. And it was already wetter than she had expected. Something she was glad to see. They had to go out this morning, and fairly soon. She briefly wondered if he was going to manage to get the thing leaking before they left. If not… She briefly opened the plastic bag and looked inside. Seven empty baby bottles. One of them he had drank before she got there last night. One would be the one she stuck in his mouth while he was sleeping – she briefly wondered if she could do that again. The third bottle would be the other one he was supposed to drink last night but didn’t. Plus four more from this morning. All of them there and accounted for. Perfect!
Chad soon found himself once again trapped in his highchair with a bib tied around his neck. Mel brought his breakfast of baby cereal over to him and handed him one of his tiny baby spoons to eat it with – held toddler style in his left fist. By the time she brought him yet another bottle to drink, he was already carefully attacking the cereal. He wasn’t the least bit happy to see the bottle she brought him, even though he knew she always gave him one with his breakfast. That would make bottle number six for this morning alone… and it was still early.
Mel poured herself another cup of coffee and watched him eating for a few moments. He was doing much better today than usual at not spilling as much of his cereal. She noticed that he also appeared to be going more slowly and carefully than he had yesterday. But yesterday he had been famished. She briefly wondered how hungry he was today. Obviously not nearly as hungry as yesterday, but he still had to be fairly hungry. Since he was eating baby food now and Sandy was going to give him nothing but baby food later, then she figured that he would be more than ready for something better to eat by tonight. Could she use that to her advantage somehow? She wasn’t sure how yet, but she decided to keep the idea in mind for later. Leaving him to his breakfast, she went into her bedroom to start getting ready.
Chad was surprised at being left alone for so long. He finished his cereal and began slowly attacking his latest baby bottle. There was nothing else he could do since he was trapped in the chair like he was. He had noticed that he was peeing fairly often again. Not huge amounts – as far as he could tell – but still, he was peeing often. But then he pretty much expected that, given all the bottles he had finished already today.
He was still working on his bottle when Mel came back into the kitchen with her empty coffee cup. She was dressed in a nice pair of jeans and a colorful top. Her makeup and hair were done and she looked ready to go out somewhere. He started to get nervous. He was only wearing the one very soaked diaper and his pink heels. “Mistress,” he called in his sissy voice, “are we going out somewhere this morning?”
Mel smiled back as she put her empty cup down on the counter. “Of course. I told you that in the note.”
“What am I going to wear?” Chad asked nervously.
Mel’s smile turned wicked. “What’s wrong with what you have on?”
Chad started panicking. “But… I can’t! Not like this!”
Mel ignored his protest and asked, “Are you leaking yet?”
In his highchair, it was hard to tell. “I don’t know,” Chad admitted, his mind mostly trying to wrap itself around having to go out somewhere dressed only in his diaper… and heels. “I have been wetting a lot.”
“Good! Finish that bottle. Then we’ll see how well you’re wetting today. If I think you’re doing well enough, then – maybe – we can find you something else to wear. Maybe! But it’s all going to depend on how much I can see that you’re wetting yourself today.”
How much she could see? That was going to be difficult to show her – despite how much he knew he was wetting himself. But any chance to not go out in just his diaper was something he had to try for. He attacked what was left of his bottle with a renewed fury. He saw her starting to leave the kitchen again and paused in his drinking to ask the next important question. “Where are we going?”
Mel was heading out of the kitchen when she heard him ask. Purposely, she ignored him and kept on going. He would find out in a little while. Let him wonder a bit longer.
Chad had finished his bottle and was wondering if he should call Mel to tell her when she suddenly came back to the kitchen again. “Where are we going?” he asked again.
“You’ll find out when we get there,” she told him. “Are you leaking yet?”
“I can’t tell in this chair,” he replied.
Mel removed the messy things from his tray and grabbed a washcloth and wiped his face and hands. She removed his messy bib – which was not quite as bad as it usually was, then she wiped off the tray. But instead of removing it, she left it where it was, keeping him confined to the chair. “I’ll be right back,” she told him. She went back to her bedroom and retrieved some makeup and brought it back to the kitchen. “This will be easier to do with you right there,” she told him as she set everything down on the tray.
Chad was puzzled about what was going on. Nothing at all was “as usual” today. Nothing! While Mel was attacking his face with the makeup, his thoughts centered around having to go out somewhere wearing only his diaper. And only one diaper at that. Two or three diapers would be better – he figured, if only because it would be like they were covering more. Besides, multiple diapers didn’t show as much how much he was wetting himself. Could he really go out like that, dressed in only one thin diaper? He didn’t think so. Not at all. But if Mel didn’t let him wear something else, then he had a feeling that he wasn’t going to have much of a choice.
Mel stood back and looked at his face. Good enough. Sandy could do better, but she didn’t think this was bad at all. She hadn’t used a lot of makeup and everything she did use was very light – no dark colors at all. Now, as he sat there in his highchair, he looked almost… she wanted to think angelic, but that wasn’t right at all. She finally settled for “youthful.” She should be so lucky herself!
“Okay,” she said as she put the makeup down and removed his tray. “Let’s get you out of there and see if you’re leaking yet.”
Chad desperately hoped that he was. If only to give him a chance to wear something other than the one diaper when they went out. Oh, and his pink heels of course. He slid down off of the chair. He knew his diaper was soggy, but was it leaking? He turned around to look at the seat of his highchair. It was wet! He had leaked! Already! “I’m leaking!” he cheered happily.
Mel smiled too. Not only at the sight of the wet seat, but at the fact that he was so happy about it. That was a good sign. Now she just had to keep him that way – for the next three weeks! She glanced up at her clock. She had no idea when he started to leak in that chair, but he had been wearing that diaper for less than an hour. Definitely a new record!
“Mistress, can I wear something else besides just this one diaper now?”
Mel did her best to put a stern look on her face. “That’s going to depend on how much I can see that you’re still trying to keep leaking.”
“But I am trying!” Chad protested. “I’m trying very hard!”
“I know. But I want to be able to see you keep trying like that. Let’s get you changed now.”
Chad wasn’t at all sure what she meant by how she thought she could tell he was continually trying. Wasn’t what he was doing enough? He followed her into her bathroom where he laid down on the floor. He was disappointed to see her grab only one thin diaper again. As she was pulling the tapes back on his soggy diaper, he suddenly realized he was peeing yet again. “Careful,” he cautioned her. “You may want to wait a second.”
Mel smiled. “That’s fine. Just keep at it.”
Chad tried to figure out if he was done peeing or not. He couldn’t really tell. “Okay… I think. At least I think I’m done.”
Mel cautiously peeled back the diaper to check, then pulled it back all the way as she realized that it was safe. It was times like these that made her really feel like she was winning this bet. But unfortunately, it was a false sense of security because every time he went back to work again, all the progress she made with him was wasted. She had to keep after him all the time. She had to push him harder and harder – if that was possible. It was her only chance to win this bet. It took only a minute to change him into the dry diaper. “An hour and forty five-minutes,” she announced as she checked her watch. It was almost nine-fifteen already. “And we have to get moving.”
Chad’s nervousness surged again. “Please Mistress, can I wear something else?” Mel looked at him and shook her head. “I don’t know yet. We’ll see by the time we’re ready to walk out the door. Maybe if I can tell that your diaper is wet by then, I’ll let you wear something else. But I had better be able to tell easily!”
Chad was ready to grasp for any lifeline. He was already wetting fairly often. “How long before we have to leave?” he asked.
Mel just smiled wickedly as she got to her feet and headed out of the bathroom. In about two minutes! Maybe you should grab another bottle and get busy with it.”
“Two minutes!” Panic hit him as he hurried to her refrigerator as fast as the heels on his feet would let him. He grabbed another bottle and began drinking furiously. He could feel himself peeing already, but since he had just peed a few minutes ago, it wasn’t much that came out. “Come on! Come on!” he urged himself as he sucked on his seventh bottle of the morning. “Pee! Pee!”
Mel purposely delayed coming out of her bedroom for a few minutes just to give him a chance. She was actually having fun with this. But then she loved dominating him all the time. “Are you wet yet?” she asked as she came back out and headed for her purse by the door.
“Yes!” Chad replied, although he wasn’t sure if he was wet enough to show.
“Show me your diaper!” Mel commanded.
Chad actually started to reach to pull up the hem of his skirt, except that he wasn’t wearing a skirt. He wasn’t wearing anything over his diaper at all. He walked over closer to her instead and tried to thrust his hips out so she could see that he had wet already. “I am wet,” he told her. “I just don’t know if you can see it yet.”
Mel shook her head. “Maybe you’re wet! It’s awfully hard to tell.”
“Please can I wear something else now?”
Mel just stared at him for a moment. “Very well. Since you wet a little bit... Take your shoes off, I’ll be right back.”
His shoes? But at least he was going to get something to wear other than just his diaper. He sat down on the floor and unbuckled his shoes. He stretched his toes as he removed each one. She was gone a bit longer than he expected her to be. But when she came back, he got quite a shock. The only article of clothing she brought back for him was a pair of white anklet socks with pink lace around the edges.
“Since you’ve wet only such a small amount, then I don’t see why you should get anything bigger than this to wear,” she said as she held the socks out for him to take.
Chad stared that the little girl style socks in her hand. They would probably be worse than wearing no socks at all. And they certainly wouldn’t cover up his diaper at all! “But Mistress…” he pleaded.
“Put them on!” Mel ordered in her no-nonsense tone. “Since you wet yourself a tiny bit already, then you’ve earned them. If you can show me that you’ve wet yourself more before we get out of here, then maybe I’ll consider letting you wear something more.”
Chad reluctantly took the socks from her outstretched hand. But before putting them on his feet, he took another long swig from his baby bottle. He pulled one sock on – then took another drink. He put the other sock on – then drank some more. He did the same with his shoes, trying desperately to pee again. But so far, nothing. He took yet another drink from his bottle before he climbed back to his feet.
He was about to plead once more with her to let him wear something else, when he suddenly felt himself peeing again. The act of standing up must have triggered it! “I’m wetting again,” he announced excitedly. And better, it felt like more than just a tiny bit. But again it didn’t last very long.
Mel looked at his diaper. “I don’t see anything different yet,” she said, then turned to pick up her purse. “Let’s go.”
“Maybe it needs a minute to start showing,” Chad replied desperately. He knew he had peed. It had to show!
As Mel looked back at his diaper, it did darken in the front a little bit. She smiled wickedly at him again. “Very well. I can see it now.” She put her purse back on the table again.
“So I can wear something else now?” Chad asked hopefully.
Mel nodded and turned toward her bedroom. “Yes,” she replied definitely. “I think you’re wet enough now. Come with me and let’s see what we can find for you.”
Chad happily followed her into her bedroom where she went straight to her closet. He waited patiently while she sorted through a few clothes in there. But when she came out carrying his pink baby dress he nearly died. “No!”
Mel took the dress off of the hanger. “It’s either this or just your diaper,” she told him.
Chad just stared at the dress in horror. He couldn’t! He just couldn’t! But he also couldn’t go out in just his diaper either. Unfortunately, it was no choice. He grabbed the dress and began pulling it on.
The incredibly short dress was more like a shirt in length because it was so short that it left the very bottom of his diaper exposed. The top of it was made to look like he was wearing a frilly white blouse under the pink and white check pattern of the rest of the dress, but it was actually all one piece. The whole thing was set off by the two white bows in front at the waist line of the dress – which was higher than his actual waist line.
Mel almost laughed as she watched him. Actually, she had planned on him wearing it all the time, but getting him into it this way was a lot more fun than just telling him to wear it. She glanced down at her watch. It was getting late. She hoped it wouldn’t be too late. Fortunately, the dress only took a moment for him to get on. “Let’s go,” she announced happily as she headed back toward her purse by the door.
Chad was in shock as he followed her out of her bedroom. The silly dress he was wearing hardly covered his diaper at all! The bottom of it was plainly visible underneath the bottom of his silly dress. He actually wondered if he would have been better to go out in just his diaper and nothing else.
He saw Mel grab her purse and was obviously waiting for him to get his. Was she really going to take him out dressed like this? Really? He didn’t know if she would or not. But it sure seemed like it. He paused a moment before he grabbed his own purse and the diaper bag right next to it. She couldn’t really be taking him out like this. It had to be a joke!
“Are you ready now?” Mel asked.
Chad gulped and nodded his head. “Yes, Mistress.”
“Curtsey when you talk to me!”
Chad curtseyed and repeated. “Yes, Mistress.”
Mel started for the door, then stopped and turned toward him. “Show me your diaper!”
Once again she had caught him off guard! He immediately dropped his diaper bag and with his purse over one arm, pulled up the hem of his dress that did little to cover up his diaper to begin with. Was he fast enough?
Mel shook her head. “At least you tried. But it doesn’t look like you’re any wetter. Maybe you better grab your bottle and finish it in the car.”
Chad grabbed the baby bottle he had left on the floor a few minutes earlier. But as he did so, he realized that she was delaying things. Maybe she really didn’t plan on taking him out anywhere dressed like this! Feeling much more confident now, he stood back up with the bottle in his hand and grabbed his diaper bag in his other hand.
“Are you ready?” Mel asked again.
Chad recognized the delay. She wasn’t taking him out at all.
He dropped another curtsey. “Yes, Mistress,” he said more confidently.
Mel opened the door and held it wide… and before Chad knew what was happening, she had ushered him right out through it and was closing it behind them. He couldn’t believe it!
“Let’s go, Sissy,” Mel said as she headed for her car. “We’re late!”