The Bet - Chapter 30 (Sunday – week 5 Part 4 of 7)

The Bet
by Karen Singer

Chapter 30 (Sunday – week 5 Part 4 of 7)

As soon as they got home, Chad began the arduous task of carrying everything from Mel’s car, up the stairs, and into her apartment. With so many heavy bags and so many trips to make, Chad was thankful with every step for the low-heeled shoes on his feet. If he had been wearing higher heels, he doubted he could have managed it. Whew!
Mel watched as Chad made trip after trip carrying the groceries in. Another reason why he was handy to have around. She had done the same thing countless times and hated the chore every time she had done it. She’d much rather leave the job to him while she relaxed.
As soon as he was done bringing in the groceries and the door was closed again, she checked the clock. He only had a little while left before his diaper was supposed to be leaking. They had spent a long time in the store where he couldn’t get anything to drink. It would be very doubtful that he would be able to avoid punishment this time. She briefly considered going easy on him, but she ruled that out quickly. If she did, then she’d set a bad precedence. He would expect that more often and wouldn’t do what he was supposed to be doing – all the time. But how wet was he now? She couldn’t tell with his dress on. “Take that dress off, Sissy,” she yelled from her living room. “I want to be able see your diaper.”
Chad removed his dress and folded it neatly by his purse next to the front door. He felt oddly naked without it. He felt worse because he knew that he wasn’t going to be able to overflow his diaper before time ran out. He figured Mel wanted to see how wet he was now. Well, he had been trying, but the trip to the store hadn’t helped matters. He went into the living room where Mel was and curtseyed. “Did you want to see my diaper?” he asked in his silly new voice.
Mel could see that he wasn’t nearly wet enough, but she still reached out her hand and felt his diaper too. No, he would have no chance. She almost felt sorry for him. But rules were rules and he had to learn to wet profusely no matter where he was or what he was doing. “You’re running out of time, Sissy.”
Chad curtseyed again. “I know,” he answered sorrowfully. He was tempted to not even bother trying to drink another bottle. But there was still the diaper he would be wearing after this one… and the one after that… and so on. No doubt for the rest of the day.

Mel had requested just a salad for lunch and Chad had just started preparing it when his time ran out. This time, Mel didn’t count down the last few seconds. She already knew he didn’t make it. “It’s time,” she announced. “Go bring me your diaper bag and get over here,” she ordered.
Chad stopped what he was doing and took a deep breath. Then before she could yell at him again, he curtseyed and said “Yes, Mistress,” in his squeaky voice.
Mel watched him as he walked toward his diaper bag by the front door and picked it up. She wondered what he was thinking. She knew that he had tried, but circumstances had simply been in the way. But the truth was that she had to get him used to peeing constantly, no matter what he was doing, no matter where he was, no matter what it took. Otherwise, she stood very little chance of winning this bet.
As she saw it, her biggest obstacle to this was his job. That was the one place where she wouldn’t be able to control him as much… as far as she could figure so far. So she had to make every moment when he was not at work count in her favor. At work he was holding back, working hard to gain more and more of the very control she needed him to lose. For every ounce of effort he put into holding back, she figured it would take at least ten times that effort to make him lose it again. No, there could be no letting up on him. No matter what!
With head held down, he stood before her, diaper bag in hand, and curtseyed to her. He didn’t say anything even though they both knew that he was supposed to. This time, she didn’t care. She took the diaper bag from him and dropped it on the floor. Then she knelt down and pulled open the tapes on the wet diaper he was wearing. “I know you tried,” she said as the diaper fell to the floor. “I know that we were out and it was hard to get enough liquids into your system to make that diaper leak.”
She stood up again and pointed toward the back of the chair. Still staring sorrowfully at the floor, he slowly turned toward the chair and leaned against it. She picked up her stick and waited. It took a few moments, but eventually he raised his bare backside up to her, offering it to her for his punishment. A soft sob escaped him. She finally continued with what she had been saying. “But we can’t let circumstances get in the way of what you’re supposed to be doing.” Whap!
Even though Chad had been prepared for it, the stinging blow caught him by surprise. His whole body jerked. The lingering pain continued to sting terribly, but he knew now from plenty of experience that this was just the beginning. He stood and turned toward her, curtseyed, and thanked her. Then it was back into position again.
“So if it looks like circumstances might get in the way…” Whap! “Then you’re going to have to make sure that you find a way, no matter what the circumstances.” He dropped his curtsey and thanked her again. “Next time, if you’re worried about not getting enough to drink, maybe you should consider taking your bottles into the stores with you.” Whap!
Despite his current distress, Chad tried to picture himself walking around the stores drinking from a baby bottle. It would be worse than having the darn pacifier in his mouth. “Thank you, Mistress,” he said in his high-pitched voice again, the words now coming out amid his crying. Carry a bottle into the stores? She had to be crazy!
“In fact,” Mel continued, “I see nothing wrong with a baby carrying a bottle into a store and drinking from it.” Whap! “Babies do it all the time.”
Chad curtseyed again and thanked her. Yeah, she was seriously crazy if she thought he was going to go around drinking from a bottle in the stores all the time. But then, he was already going shopping wearing a dress and sucking on a pacifier!
“So if that’s what it takes, to keep you wetting enough…” Whap! “Then that’s exactly what you’ll have to do!”

“Excuse me, Mistress,” Chad’s sissy voice interrupted. “Your lunch is ready.”
Mel looked up from her work and smiled. This was living. This was what life was all about! Having your own personal servant take care of all the little menial things for you. She got up from her seat and glanced at the table in the kitchen. It was set nicely with her salad plate out and waiting. But she didn’t head there yet. It had already been a busy day and she had a lot of other things planned for the rest of the day. There was very little time to do the one thing she needed to do the most. And the person that it all concerned the most, Sissy, was also going to be busy with things such as cooking and cleaning for company later. But still, there was something special that she needed to accomplish with him too.
No use wasting time. He didn’t need to be doing anything else while she ate. His diaper was fairly fresh and hopefully the suppository she had stuck up inside of him when she had changed him wouldn’t do anything for a while yet. It was time to start – brainwashing him.
Now, how should she go about it? She headed for the area between the kitchen and her living room where there was a little bit of room. “Okay, Sissy. I want you to walk around the room, stop in front of me, curtsey and greet me with that cute little sissy voice of yours.”
Chad was confused. What for? What was she really after? But there would be no way of knowing till he tried it… as easy as it sounded.
He started around the room but her voice lashed out and quickly stopped him. “Ah, ah!” she admonished. “You didn’t curtsey after I told you what to do and you didn’t say ‘Yes, Mistress!’”
What a pain! He dropped a curtsey to her and repeated, “Yes, Mistress,” in his high-pitched voice past the pacifier still in his mouth. Then he again started walking around the perimeter of the room, rarely taking his eyes off of her for a moment. When he got back to her again, he curtseyed, said, “Hello, Mistress,” and stood there waiting.
“Good. Now curtsey again as if I’ve just finished telling you something, say ‘Yes, Mistress’, and then do it all over again.”
Huh? Do it over again? What was the point? But he dutifully curtseyed, said his little bit in his tiny voice, and then started around the room again. Why? When he got back to her again, he again curtseyed and said “Hello, Mistress.”
“Good,” she replied. “Now do it again, and keep doing it, over and over while I eat.”
Chad stared at her in surprise. She wanted him to keep doing it? Why? It made no sense. But she was waiting, and he didn’t see any way out of it. “Yes, Mistress,” he replied, mumbling around his pacifier. Then he started once again around the room.
Mel sat down at the table and watched him as he came back to the same spot again, but this time she wasn’t there. He looked confused. Then he turned and headed towards her at the table. “No, Sissy. Make believe I’m right where I was!”
Huh? Dumb! He backed up, repeated his curtsey and greeting, then immediately launched into another curtsey saying “Yes, Mistress,” and he was off around the room again.
“Next time, wait a few seconds after you initially great me… as if I’m talking to you. And pretend I’m right where I was. Not at the table here.”
Chad came back to the spot and did as he was told, but he kept glancing back toward Mel at the table. Mel could see that it just wasn’t working the way she wanted it to. He needed something else, something to focus on. She got up from the table and glanced around the room. What could she use? Her eyes fell on a tall floor lamp next to one of her chairs. Perfect! “Grab that lamp, Sissy, and bring it over here.”
Chad had no idea what was going on or what she was trying to accomplish, but he unplugged the lamp and brought it to her. “Where do you want me to plug this in?” he asked.
“I don’t!” she replied. “And you didn’t curtsey again!”
Ugh!
Mel set the lamp exactly where she had been standing. “Okay, Sissy, just pretend this lamp is me. Pretend I’m not at the table, but right here. Talk to the lamp.”
Chad couldn’t believe it. Now she wanted him to talk to a lamp? This was sooooo dumb! But since he really didn’t have much of a choice, he dropped a curtsey to Mel – not the lamp, said, “Yes, Mistress” in his sissy voice, and took off around the room yet again. Mel stood back out of the way.
Chad glance briefly at Mel as he approached the lamp, but then he turned his attention to the lampshade. He stopped and curtseyed. “Hello, Mistress.” He paused, then curtseyed again and said, “Thank you, Mistress.” Then he started another lap. As he began walking, he glanced at Mel to see if that was what she wanted.
“Perfect!” she declared. “Now just keep doing it.”
Round and round Chad walked, repeating the same ritual over and over again while Mel ate. She was halfway through her salad though when she realized that she was keeping him from drinking anything. What she had him doing was important, but not nearly as important as keeping him wetting. She quickly got up and found his bottle. “Wait a minute, Sissy,” she said as he finished greeting the lamp. She held out his bottle for him. “Here, you can drink this if you need to while you’re walking.”
Chad took the bottle from her and waited while she pulled the pacifier out of his mouth herself. He had mixed feelings about having to keep drinking even while he was doing this… whatever it was that he was doing. But then, if he didn’t keep drinking, then there would be no way that he could overflow his diaper. So he supposed he was actually grateful. “Yes, Mistress,” he said yet again, this time directly to her, and this time in a much clearer voice without the pacifier.
As Mel sat down to finish her lunch, she felt much more satisfied. He was walking around the room while drinking his bottle. He was practicing nicely with the lamp. His silly high-pitch voice thrilled her every time she heard it. And whether he realized it or not, these things would eventually become more and more of a habit to him. Yes, this was working out very well.

Chad was no longer paying much attention to what he was doing. His mind had long ago ceased to be interested as he walked around and around her living room, curtseying to the lamp each time. The only break he had had was when Mel let him eat a plate full of baby food in his highchair. Then it was back to the mind-numbing walking and curtseying. What a major pain. In some ways, he’d rather be standing on his perch in the corner… well, maybe not.
The only minor little distraction had come when Mel had replaced the bottle he had been drinking with a fresh one. Now that bottle was almost empty too. Curtsey. Talk to the lamp in the stupid high-pitched voice. Curtsey again. More sissy talk. Walk. Over and over and over again… Boring!
Mel was barely paying attention to him the whole time he was doing it… or it seemed that way anyway. The least little time he did anything not right or even hesitated a bit, she yelled at him from the kitchen where she filling baby bottles with tea and fruit juices again. He noticed that most of these bottles were getting sealed with her tape again so they couldn’t be opened without her knowing it. He had no doubt where each of those bottles would be going very shortly – the refrigerator in his apartment.
As he walked, he could feel his diaper gradually getting wetter and wetter, which he was very happy about. He was peeing in smaller and smaller amounts now, but at least he seemed to be doing it more and more often. But because he wasn’t peeing in large volumes, it was becoming harder and harder to feel himself peeing. In fact, very often he really couldn’t tell if he was peeing or not. But at least his diaper seemed to be getting more and more soaked.
And then it happened. He approached the lamp and curtseyed, but as he put his leg back and dipped down, he suddenly felt the unstoppable suppository that Mel had put up inside of him going to work. There was almost no warning. One moment he was about to curtsey, the next he was filling his diaper as his legs seemed to lock in place, holding his curtsey for an impossibly long time. He didn’t talk to the lamp, he couldn’t. He hated the feeling of what the suppositories did to him. He hated having to mess his diapers every day. It was demeaning. It was humiliating. It was messy and uncomfortable. Yet, underneath it all, despite hating it, he loved the humiliation of it too. If only he could get some relief… but then, did he really want any relief anymore? He had lived with the constant feeling of needing release for so long now that it had become almost a part of him. Sometimes, he wondered if it was the only thing that helped him get through the daily trials and humiliations that Mel put him through. Did he really want release? Damn yes!
Mel saw him stop his endless rounds. Surprisingly, he seemed to be almost stuck in his curtsey position. Strange. What was going on? She headed for him as he very slowly stood back up. But the smell reached her before she even got close. Part of her was disgusted, but the other part of her wanted to laugh. He had just messed his diaper while he was trying to curtsey. What a laugh! Obviously, he had no control over it at all – which was just what she wanted.
He turned to face her with a very forlorn look on his face. She almost felt sorry for him… almost. “Come on, Sissy. Let’s get you cleaned up. Things like this are going to happen… in fact, they better happen!”
A little while later, Chad was again going round and round in Mel’s living room, curtseying and talking to her lamp. His diaper was clean and fresh, and he again had only two hours to make it leak. Damn! Would these endless torments that Mel put him through never end?
Once again, Chad started to succumb to the monotony of what he was doing, but the sudden knocking at Mel’s door jolted him back to reality. “Get that please, Sissy. And make sure you greet whoever it is… properly!”
Chad was always nervous about answering her door, especially dressed the way he was. He actually felt a bit disoriented as he now headed in a different direction instead of walking back towards her floor lamp. He opened the door and was relieved to see Sandy and Cassie standing there. He curtseyed, “Hello, Sandy.” Another curtsey, “Hello, Cassie.” Both women looked startled the moment he had opened his mouth.
“Hi, Sissy,” Cassie replied as she pushed her way past him. Chad closed the door behind them.
“I see you’ve been playing with the way he talks again,” Cassie noted to Mel as she walked in.
Mel smiled broadly. “You like it? I loved the baby language Sandy taught him, especially in the new higher voice. But it got to be too much of a pain trying to figure out what he was saying all the time. So now he can either talk in Sandy’s baby talk, or now his new sissy talk.” She giggled.
“Sissy talk?”
“Yeah, that’s what I decided to call it. This way…” she stopped suddenly and looked over at Chad who was standing out of the way and just listening. “Sissy… I don’t see you walking!”
Chad’s knees nearly buckled. Did she expect him to keep doing her stupid little exercise even with company there? But again, Mel was glaring at him all too threateningly. “Yes, Mistress,” his voice squeaked as he dropped another curtsey. Once again, he began his trek around the room.
The eyes of the three women followed him and watched him closely.
“What’s he doing?” Sandy asked after Chad had addressed the lamp twice and was once again circling the room.
“Learning!” Mel replied in no uncertain terms. But she didn’t elaborate further.
The three women continued to watch him closely. “I hate the way he’s dressed,” Sandy declared. “It looks awful. Besides, if he’s going to learn to curtsey properly, then he should at least be doing it in a skirt.”
“I think she’s got a point,” Cassie agreed. “Besides, I don’t care for the way he’s dressed either.”
Mel felt frustrated. She looked Chad over carefully as he continued his trek around the room. He did look kind of lousy without his maid’s dress on. Just wearing a bra, waist cincher, his diaper, along with his low-heeled shoes didn’t help him look very feminine… or even babyish. But there had been a purpose to him being dressed that way. “I had him remove his dress to make it easier for me to see how wet his diaper was,” she explained.
“Looks kind of wet to me,” Cassie replied.
“Me too,” Sandy agreed. “But I still think he needs a skirt to practice with.”
“Like I said, I think she’s got a point,” Cassie agreed.
Mel watched as Chad curtseyed to the lamp again. Yeah, they were probably right. Without a skirt he wasn’t doing it very gracefully at all. “Okay,” she agreed.
“What do you suggest? I have his maid’s dress here. He can put that on again.
“Boring!” Cassie stated. “How about one of those new outfits you bought him? They’d be perfect.”
Mel smiled. “They’re for later,” she whispered.
Sandy giggled. “Then I guess we’ll just have to find something from his closet at home. Why don’t you leave him to me?”
Mel stared at her for a moment. She really couldn’t think of a reason to refuse Sandy’s suggestion. “Go ahead if you want,” she replied. “Just don’t take too long. I want to keep him practicing and he’s got dinner to prepare later too. But remember, I’ve got to be able to see his diaper without too much trouble.”
Sandy practically jumped out of the chair she was sitting in. “Don’t worry, we’ll be real fast. Just something basic, I think.”
“Oh, and Sandy,” Mel added, “please don’t remove his diaper.” She glanced at the clock, he’s still got a little while to make that thing leak and I don’t want anything to get in the way of that.”
“Make it leak? Why?”
Mel didn’t want to blurt out the whole reason in front of Chad, even though he could probably figure it out easy enough. “Because that’s what I’ve been making him do, all weekend!”
Sandy shrugged. “Sounds dumb to me, but if that’s what you want… Come on, Sissy. Let’s see what else you have in your closet.”
Chad had been mindlessly continuing with the exercise while the women were talking. He immediately turned toward Sandy, dropped a curtsey and said, “Yes, Mistress.”
Sandy giggled. “He’s funny!”