The Bet - Chapter 5 (Wednesday - week 1 Part 2)

My hopes have been dashed!

I almost had an adventure! For the last week, everybody here has been planning on me driving my in-laws and my wife out to Louisiana to stay for a week to take care of some business. That would have given me four or five days to dress and play. Just as everything was completely set and final, last night my mother in-law decided that they wanted to stay at home in Louisiana for at least a few more weeks. Possibly longer. So my wife will be coming home with me again and I won’t get to play!

My in-laws aren’t able to take care of themselves – and they know it. But suddenly my mother in-law is dragging her feet about moving in permanently with us. My father in-law thinks they already live here permanently. He’s so confused and getting more so all the time. I’m afraid it’s going to take another major episode for them to finally get it together enough to say bring us to your house for good.

I had really hoped to let you know today that I would be adventuring again soon. Now I’m beginning to wonder if I’ll ever have another adventure again.

Karen


The Bet
by Karen Singer

Chapter 5 (Wednesday - week 1 Part 2)

Andrea was working on the paperwork for another will when Chad finally came waddling into the office. She nearly burst out laughing just watching his straddle legged walk. The two clients that were waiting in the office were staring at him too. He looked horribly embarrassed. The poor guy was miserable, that much was for certain.
“Mel’s not back from court yet,” she told him as she got up from her desk. “She told me to have you wait in one of the offices in the back.” She led the way down the hall while Chad followed as fast as he was able to, which was really none too fast. The office she led him to had a beautiful leather couch. “I’ll be right back,” she told him.
Chad headed straight for the couch and laid down. He was so tired that he felt dizzy with relief when he did so. But before he could fall asleep, Andrea was back again – and holding a large cup of coffee in her hands.
“Mel wants you to drink this before you do anything else,” she told him.
Chad just looked at her. Did he have to do whatever Andrea told him to do too? Ok, so Mel had sent the instructions through her. He decided to err on the cautious side again and drink the coffee. As wet as he already was, it wouldn’t even matter if he had wet himself again. He took the coffee she was holding out for him and sipped it. At least it tasted good. Far better than the awful tea she usually made him drink.

“I almost hate to wake him,” Mel said a few hours later after she had finished with the last of her clients for the day.
“I know what you mean,” Andrea replied. “God, you should have seen him waddling in here when he arrived. It was hysterical.”
“I can’t get over it. Look at how bulky his diapers are, even compressed under that girdle. He better get used to it though because that’s just how I want to keep him. I’ll put him to bed early tonight. That part he’s probably going to appreciate.”
Mel left the room and came back a few minutes later with another cup of coffee in her hands. “He’s really going to hate me.” Both women giggled.
“Chad, wake up. Chad! Wake up!” Mel had to shake him a bit to break him out of his slumber.
Chad finally startled awake. “Can we go home now?”
“Just as soon as you drink this,” she said as she handed him the coffee.”
“Oh hell!”
Mel busied herself getting ready to go home while Chad finished the coffee. Chad was still bone-tired, but at least the coffee had helped wake him up a bit. “Go home and get yourself cleaned up. I’ll get some burgers for us for dinner, then I’ll be up to diaper you again as soon as I can.”
Chad gratefully went home. He was hungry, he was tired, and he had had enough to drink in the last few days that he didn’t ever want to drink anything ever again. And worse, the coffee was making him have to pee again. He sighed and relaxed as he wet himself yet again. Worse, he was beginning to feel the need to relieve himself in another way too because he hadn’t been able to get his diapers off earlier to do it. He had no doubt that that was going to be a problem tonight.
Getting his male clothes off was easy. Getting his pantyhose off wasn’t hard either. But that’s where the easy part ended. Just pulling the shoulder straps off from the girdle wasn’t easy. When he finally got them down, the straps had left deep, red, marks across his skin where they had been all day. He rubbed them to ease the pain. Then he had to struggle and struggle to get the rest of the girdle off. In doing so, he actually pulled his diapers and plastic panties off with it. There was just no separating them. But finally he was free from it all. He got into his shower and just soaked for a long time under the warm spray. He hardly even thought about it when he had to pee again and he simply let loose.
Mel rushed in as he was drying off. “Oh good, it looks like you didn’t have to wait too long for me.”
“I just now got out of the shower,” he admitted.
“When was the last time you peed?”
Chad blushed. “In the shower… I’m sorry, I know I shouldn’t have, but I just didn’t think about it. I’m really just too tired tonight.”
“Don’t be sorry. I’m glad you peed when you did.”
Chad was a bit confused, but he chalked that up to being so tired.
Mel prepared four diapers for him on the bathroom floor. Then she had him lay down on his stomach. She noticed that his backside was still a bit red from the night before. She was actually glad about that. She once again coated it liberally with the baby lotion. Chad was about to roll over again, but she stopped him. “Wait a minute.” She got up and went to a small bag she had in her purse from the drug store and brought out a small jar. She opened it and took out a glycerin suppository. Then she put the jar away again. Kneeling once again over Chad she said, “Now hold still.” Then she inserted the thing as far as her finger could reach.
Chad arched his back. “What are you doing?”
“Never mind,” she told him. “Just lay still.”
Chad didn’t dare move while Mel got up to wash her hands. He just couldn’t figure out why she had stuck her finger up his butt. When Mel came back, she rolled him over again and powdered him heavily. Then she taped all the diapers up firmly and put a clean pair of plastic panties on him. Chad was expecting her to make him wear the darn girdle again but she didn’t. Instead she dressed him in the baby doll nighty instead. After what Chad had worn all day, he actually felt very comfortable, even with four diapers on.
Mel picked out another pair of heels for him and had him put them on. Then she told him, “We’re going back to my place, and don’t you even think about giving me any lip about the way you’re dressed!”
Chad started to panic. But he had no way out. She practically pushed him out the door ahead of her. Unfortunately, several of the neighbors were walking up the stairs when she did it. Both of them women. Chad had no place to run to because Mel was right behind him, locking his door. The neighbors were staring and squealing with laughter. And Mel was standing there and smiling.
“What’s going on Mel,” one of them asked.
“Have you met our new sissy neighbor?” she asked.
“Oh, he’s just adorable, one of them replied.
“Oh he is,” the other one added. “He could use a little bit of makeup though.”
“And how about some nail polish too,” the other one added. They all laughed – except Chad who wanted to run – anywhere.
“Maybe next time girls,” Mel replied. Then she finally led the way to her apartment where she waved to the two women before she unlocked and opened her door.
Mel had picked up burgers for both of them and an extra large drink for Chad. She went straight to the kitchen and poured his drink into his baby bottle and handed it to him. “Get busy,” was all she had to say.
Mel made Chad sit on her kitchen floor while he ate, while she sat at her kitchen table and watched him. When he finished his first bottle, she grabbed it from him and refilled it again. “We’re going to have to get you more bottles,” she decided. She looked at how much more of the drink that she had bought him was still left in the original cup. “Maybe a lot more bottles.”
“Why can’t I just drink it from the cup instead?”
Mel handed him the second bottle, “Because I like seeing you drink from the bottles.”
Chad reluctantly put the thing back in his mouth and began sucking on it again.
He was just finished with dinner and on his third bottle when the feelings in his stomach hit him. Mel saw that he suddenly looked very uncomfortable and worried. A minute later a small cramp hit him and he definitely looked worried. “Feeling like you have to do something?” she teased.
Chad nodded his head as the intensity of the pressure quickly got worse. “Yeah,” he replied. Then he looked up directly at Mel. “Please! Please let me use the toilet. I have to go so bad I can’t stand it!”
Mel nearly laughed. “No! Never again. You know that. That little suppository I stuck up you earlier is simply doing its job. And that’s just one more thing you’re going to have to get used to. So I suggest you let it all out, because otherwise, obviously, you’re just going to suffer.”
“Suppository!” Chad grunted out. “Damn!”
“Watch your mouth! I don’t like swearing!” She watched as Chad struggled a bit more, then he started to get up. “No, no! Babies stay on the floor!”
Chad got back to his knees, but no further as the intensity became more than he was capable of handling. He had no choice, he let it all out into his diapers while Mel watched him totally fascinated. As he was nearly finished, he realized he had to pee too. He relaxed even more. He was so humiliated, he wanted to cry. This was something he had never done before and didn’t ever want to do again. When he was finally done and he had caught his breath, he looked back up at her again. “Please can I change myself now?”
“No,” Mel said again. Not till tomorrow morning. “Like I said, that’s something else you’re going to have to get used to. So I intend on giving you one of those things every night from now on.”
“Why?”
“Because I want to. No other reason necessary. Now sit back down and finish your bottle.”
Chad looked positively distressed. Sit back down? With what he now had in his diapers? But he had no choice. Very gingerly, he eased himself back to a sitting position. The feeling was not what he expected since the suppository had made everything come out so soupy. But it was fairly awful to him never the less.
As he brought his baby bottle back to his lips, she asked, “Did you pee yet?”
“Yes,” he nodded. “While I was doing the other.”
“Good,” she replied getting up from her chair. “Now finish drinking quickly, there’s still a lot more soda in this cup. And as soon as you’re done, you can go to bed.”
Bed! The very thought of it was like a beacon his soul had been searching for. It took two more bottles before Mel decided that he had finally had enough and let him get to his feet again. Mel noted how gingerly he was walking now that his diapers were messy. That thrilled her too. “I’ll be there tomorrow morning again to help you get dressed. I better not find any evidence that you’ve tried to remove anything. Chad didn’t answer. He was just too tired and humiliated, and just then more worried about going out through the door again in his present condition. But she held the door wide open for him and ushered him out.

Mel was catching up on some work she had brought home from the office a little while later when her doorbell rang. When she opened it, Cassie and Sandy, her two neighbors who had seen Chad earlier were standing there.
“Ok, dish girl!” Cassie said before Mel could even say hi. “What’s going on? We’ve been laughing about it ever since we saw him and now we just had to stop by and find out? Where is he?” she added looking in through her door.
“I sent him home to bed,” Mel replied, laughing a bit herself. These two girls had never come out and told her, but Mel had long ago pegged them as lesbians. They weren’t close friends, but they did see each other occasionally. Mel stood back. “Come on in,”
Neither of the girls needed a second invitation. “You sent him to home to bed?” Sandy asked as she walked past.
“Yeah,” Mel replied, “but he needed it. He hasn’t had much sleep in the past few nights now… and I’m afraid he may not get much tonight either.” While her two guests sat close together on her couch, Mel filled them both in on the details of the bet.
“I don’t believe it!” Cassie finally said, at which point, Mel got up and showed them her copy of the contract. “Unbelievable!” Sandy remarked as she read through it closely. “You should frame this thing and hang it on the wall.”
Mel’s eyes went wide. “That’s a great idea. I love it. In fact, I may do that to his copy too, so everyone can see it. Thanks.”
“So do you still call him Chad,” Cassie asked, “or do you have some other sissified name for him now?”
Mel was a bit surprised at the question. “No, I hadn’t thought of that. Really. I just call him Chad… But I like that idea too. But what do you think would be a suitable name for him now?”
The three women banded about name after name and laughed over most of them. But finally, Mel cut to the chase. After hearing name after name, one of them struck a note that she really liked. “That’s it,” she declared. “I’ve decided.”
“What?” both her guests asked at the same time.” Mel put a teasing look on her face. “I’m not going to tell you.”
“What?” the two girls said together.
“I think I’ll let him tell you himself.”
Cassie and Sandy both looked shocked. “I can’t wait!” Sandy said.
“When?” Cassie added.
Mel shook her head. “I’m afraid that’s going to have to wait for a while. There are other things I need to do to him first before I change his name.”
“Oh come on,” Cassie complained.
“You’ll just have to wait. But I promise you, when the time comes, you’ll be the first ones to know.”

Chad laid down on his inflatable mattress in misery. He had to pee… again. He barely gave it a second thought. Damn the woman. She was constantly coming up with more and more things to make his life miserable. But he was so tired he could barely think straight. He fell asleep, for a while. But all the liquid she had once again forced down his throat was waiting to get out. For the first time, he didn’t bother to roll over onto his back to do it like he usually did, he just let loose. It was easier. He immediately went back to sleep, for about half an hour. Then he had to pee again. Later still, the suppository did the rest of its work.