The Bet - Chapter 44 (Sunday – week 7 Part 3 of 9)

The Bet
by Karen Singer

Chapter 44 (Sunday – week 7 Part 3 of 9)

Rearrange the kitchen. Keep the laundry going. Drink more baby bottles. Keep trying as hard as possible to wet his diaper so it could leak before the time limit was up. His mind was so occupied with everything he had to think about that when Mel’s phone rang it startled him. After several rings, he heard her finally answer it.
“Hi Ray.”
Chad listened as hard as he could. Unfortunately, he couldn’t hear very much from the kitchen. Maybe he could hear better if he checked the laundry? He wandered out past her. He saw her sitting back with a smile on her face and laughing, as if she was enjoying talking to him. Was she? He quickly berated himself. Why shouldn’t she enjoy talking to Ray? She was a grown woman. She knew what kind of guy Ray was. And why should he get upset over her talking to him? It wasn’t like she was ever going to go out on a date with … a sissy! She was a beautiful woman. She deserved to go out with someone – more qualified – once in a while. He barely noted that the washer was still running before turning around and heading back into the kitchen, where he grabbed his latest baby bottle and did his best to not listen. He felt like such a sissy as he sucked on his bottle… such a loser.
“Sissy…” Mel yelled a few minutes later.
Chad hurried out to the living room, his hands already grabbing the hem of his dress, preparing to lift it straight up if she gave the command. She was off the phone. He curtseyed, but his hands never left his skirt. “Yes Mistress?”
“That was Ray. He and Derek will be here about six and we’ll all go in Ray’s car tonight.”
Chad wasn’t all that thrilled. He really wished this date wasn’t going to happen at all. He especially wished that he wasn’t going. The very thought of having to go out with Derek, even on a double date, bothered him a lot. Not to mention that having to be out on a date dressed as a woman was going to be very… very embarrassing! And then… then there was the end of the date! But what could he say to her? He curtseyed. “Yes Mistress,” he replied.
“You don’t seem very thrilled about it,” Mel noted.
Chad shrugged. “I’m not.”
Mel was out of her seat faster than he thought possible. Her stick caught the side of his leg with another harsh stinging blow. He didn’t have to ask what it was for. He quickly curtseyed again. “Sorry, Mistress,” he apologized. Gee! It was hard to remember to keep curtseying every little time he even thought about opening his mouth!
Mel sat back down again and set her stick within easy reach. “Why aren’t you thrilled?” she asked. “Any girl would be excited to be going out with these guys, either one of them.”
Chad was careful to curtsey this time, in fact, he did it slower than usual to make sure she saw him doing it. “But… I’m not any girl,” he replied. “In fact, I’m not a girl at all!”
“Well, you’re certainly not a man!” Mel replied quickly, and all too firmly.
Unfortunately, Chad knew that fact all too well – as badly as it hurt to admit. He curtseyed, but it was a slight curtsey this time. “I know, Mistress. I know,” he sighed.
Mel forced herself to smile sweetly. And she really did understand… but what was happening was just too much fun to not press the issue further. “So what is it you’re upset about, having to be on the date with Derek, or you’re worried about going out as the girl this time?”
Her question made him feel embarrassed and queasy – all at the same time. He almost didn’t curtsey but he remembered just in time. “I think… both, Mistress,” he admitted.
“Why?”
She would have to ask! He curtseyed again – he was getting really tired of doing it. “First of all, Derek is my friend. I don’t feel right about it since he’s going to have to go out with me instead of a real woman. That’s just plain… a horrible thing to do to him!”
Mel shrugged. “He lost the bet. It’s the consequence he has to pay. He understands that, otherwise he wouldn’t be doing it.”
Chad knew that, but he still didn’t like it and it still didn’t feel right. He almost spoke again without curtseying. The slight delay as he did so seemed to interrupt the flow of the conversation. “I think it’s worse because he has to go out with me.”
“Because he’s your friend?”
Chad nodded, then curtseyed. “Yes, Mistress.”
She shook her head. “It doesn’t matter. He still knows what he’s getting into.”
Chad was about to speak, but he remembered to curtsey just in time before he spoke just the one word. “Unfortunately.”
Mel almost chuckled. “And what about the other thing? What about you being the girl this time? Why are you worried about that?”
Chad stared at her wide eyed for a moment. How could she ask such a question? Wasn’t it obvious? He didn’t even have to think about curtseying this time, he just did it unconsciously – and almost angrily. “Because I’m not a girl!”
“As I said, you’re not a man either.”
His curtsey was again automatic. “And I’m also not a girl.”
Mel smiled. “But I think we can now safely say that you’re a lot less of a man now than you are a girl… Or… You’re now more of a girl than you are a man.”
That statement made his head dizzy. More girl than man? He paused as he tried vainly to find a reply to that statement.
Mel noted his lack of response and pushed on. “Tell me, in what ways do you still think of yourself as a man.” Actually, once she asked the question, she was very interested in his answer because she had been systematically trying to erase every manly trait she possibly could.
Chad went from being dizzy over what she had said before, to being shocked and dizzy over her current question. In what ways was he still a man? That had to be obvious! Again, he almost forgot to curtsey before opening his mouth, but he remembered just in time. “I… I am a man!” he replied.
“Are you sure?”
He curtseyed again – gee it was getting tiring. “Okay, yes, I’m a sissy… a big one! But I’m still a man.”
“In what way?”
He couldn’t believe she was pushing this.
“What about you is the least bit masculine?”
He had to stop to think for a moment, but a decent answer was not coming to his mind. He curtseyed, just to get it out of the way and also to stall while he still searched for a good answer. An answer that should be all too obvious. “Well,” he finally said. And the first thing he could think of was his under-used and caged male appendage. “I have a penis. That makes me a man.”
Mel laughed. “Are you sure? As far as I can see lately, all you’ve got left is a bit of a ‘growth’ down there. Certainly not anything you could really call a male penis anymore. And saying it’s a penis implies that you’re going to be capable of using it on a woman and satisfying her with it. Somehow, I seriously doubt that that little ‘growth’ can do that. Besides, it’s all covered and locked up. You can’t even touch it or play with it, so it certainly can’t give you any pleasure either. No, I’m afraid that that one won’t hold up. You’ll have to come up with something more than that!”
Chad was shocked – again. Something more? Okay, so maybe it wasn’t the biggest cock in the world and maybe it didn’t respond like it used to anymore… but it was still there, little or not. But since she wasn’t accepting his answer he searched for the next item. Again he curtseyed as his brain fought to come up with an answer. “My body!” he finally exclaimed. “I don’t have a woman’s body!”
Mel was surprised at his answer and the look on her face showed that plainly. “Your body? How can you say that? Since you’ve lost so much weight, and since we’ve been keeping you in a waist cincher and the girdle, your body shape has changed drastically. Okay, so maybe your breasts are fake, but you can’t tell that with your clothes on. And even without the girdle now, your body shape is definitely more feminine than anything else. I seriously doubt that if you started dressing like a man again, that your body would look much like a man in the clothes! In fact, I’ll bet most people would think that you’re a woman wearing the clothes. Okay, maybe a small-breasted woman, but still a woman.”
Chad was startled again. Was it possible? Had he changed that much? He wasn’t really sure. He would have to think about that one. Of course he had lost a lot of weight, and Robin kept telling him how good he was looking now… But… The realization startled him. Was it possible? He really didn’t thing so, but… Was it possible?
Mel watched him struggling with what she had just said. It was time to move in for the kill. “Now let’s look at the other side of the coin. Since you’ve lost so much weight and you have been wearing that waist cincher all the time, your body does look more feminine than masculine. Your hair is styled femininely. You wear makeup like a woman. Your nails are long and polished – and you’re obviously used to having them that way. You only wear women’s clothes – and mostly dresses and skirts at that! In fact, you’re probably more comfortable wearing high heels now than I am. Let’s see… You can’t use your male voice anymore. Your little body movements and habits are starting to get more feminine every day.” She paused for a moment before continuing. “You certainly can’t have sex like a man anymore. In fact, you get a lot of pleasure from being penetrated like a woman now. Isn’t that right? Don’t deny it, because I know for a fact that it’s true.”
Chad’s ego was wilting more and more under her onslaught. The problem was… that everything she was saying was true!
“And we won’t even get into your baby habits!” Mel continued. “What man would wear a diaper, and drink from a bottle, and suck on a pacifier all the time? Why I’ll bet that right now you’d like nothing better than to sink down to the floor and suck your thumb like a baby! Am I right?”
Chad absolutely hated to admit it, even to himself. But under her long string of accusations, now that she had made the suggestion, he’d like nothing better.
“Am I right?” Mel asked again.
Chad curtseyed. “Y... y… yes, Mistress.”
“Well, don’t let me stop you if you feel the need!”
Chad was shocked. More than shocked. And it was worse because he saw her staring at him, waiting on him to do just that. Surprisingly, he felt his body sinking slowly down to the floor and his thumb rising to his mouth. He sat and sucked his thumb like the big baby that he was… and felt like the absolute biggest sissy in the world. A feeling that sent a major stimulation to his under exercised sexual need. It was true. It was all true. Everything she had said was true. He wasn’t a man… not at all. He was a sissy. More of a sissy now than he used to be. Much more! Enough of a sissy that he couldn’t even think of himself as a man anymore.
Mel leaned over and smiled down at him evilly. “If it looks like a duck and quacks like a duck, then it has to be a duck… or in this case… one big sissy! Certainly not a man. Not by any stretch of the imagination. Not… any… more! All that’s left is… a sissy!” She almost giggled as she watched him sucking his thumb harder and harder. There was more she wanted to say. Another direction she wanted to take him. But it would have to wait till later. He wouldn’t be overly receptive to it… yet. She leaned back again. “Don’t just sit there sucking your thumb. You probably need your bottle more than your thumb. Especially since your deadline is only a few minutes away!”
His deadline! In the heat of the moment, he had actually forgotten about it! He quickly climbed to his feet and started for the kitchen where his bottle was.
“Sissy!” Mel’s voice lashed out.
Chad stopped in his tracks and almost forgot to curtsey again. “Yes, Mistress?”
“You didn’t curtsey before you left.”
Curtsey before he left now? He curtseyed again. “Sorry, Mistress. Can I go now?”
“Just as soon as you curtsey for me again,” Mel giggled.
Chad curtseyed, then hurried out toward the kitchen again.
“Sissy!” Mel’s voice lashed out once again before he got very far.
This was getting really annoying! He curtseyed again. “Yes, Mistress?”
“Show me your diaper!”
Once again she had caught him off guard with the command, and despite his struggling to get his skirt up on time, by the time it was fully up, she was already swinging her stick at his exposed legs. Ouch!
“Now go get your bottle,” she told him.
He quickly lowered his skirt – most of the way down, then turned toward the kitchen again.
“Sissy!” her voice lashed out once again. As Chad turned back to her again, her swinging stick caught the side of his arm. “You didn’t curtsey before leaving again!”
Ugh! He curtseyed again. “May I go now, Mistress?”
“Of course!”
Then, just for good measure – or maybe just to be safe, he curtseyed yet again, before running to the kitchen to find his bottle.
Mel laughed to herself as she watched him hurrying away. She was having fun today, more than she expected to. And all his constant bobbing up and down as she made him curtsey for the least little thing was amusing her to no end. Darn she loved seeing him do that! Still. After all this time. It was like it never got old. She glanced at the clock. He still had five minutes left before he had to be leaking. Fortunately, it looked like his diaper was about to explode already. But would he make it? She twirled the stick in her hand once again.
Chad glanced at the clock as he put his bottle to his lips and began sucking furiously. Leak! Leak! Leak! Time was running out! He knew his diaper was totally soaked, he just didn’t feel it leaking yet. He pulled his skirt up and lightly felt all around the leg openings. No wet spots as far as he could tell – darn it! Leak! Leak! Leak! Why was it that some diapers leaked easily and others resisted so much? He was concentrating as hard as he could on trying to pee. Leak! Leak! Leak!
The minute hand on the clock moved again – as much as he wanted it not to. His desperation increased. Why was it that whenever he wanted to pee the most, he couldn’t?
Mel was watching the clock too. Time was running out awfully fast. She almost felt sorry for him, but rules were rules. And in this case, the rules were designed to help her win this bet! No let up could be possible. He needed all the incentive she could give him to keep peeing with no control at all. She only prayed that everything she was doing was going to be enough.
The clock continued to run. Chad’s eyes were glued to it, just as his mouth seemed to be glued to the baby bottle in his hand. Drink, drink, drink! Pee! Pee! Pee! Leak! Leak! Leak! But the peeing and the leaking just weren’t happening yet. His attention turned from the minute hand to the second hand. One minutes left. Why couldn’t he pee? He had to pee! He had to!
With every second that passed, his spirits sank lower and lower and as the final second ticked by and the minute hand moved once again, he knew he had failed – again.
“Are you leaking yet?” Mel called from the living room.
He hated saying it. “No, Mistress.”
“Did you curtsey before you answered me?” Mel called back.
Curtsey? She was in the other room for heaven’s sake! She couldn’t even see him! He could lie of course… “No, Mistress.”
“Did you curtsey again, this time?” she asked again.
Geez!!! This was getting ridiculous! This time he took the time to curtsey before yelling back. “No, Mistress, but I just curtseyed now.”
“Good! I’ll add some strokes to your leaking punishment later for not curtseying!”
Chad sighed and curtseyed again. “Yes, Mistress.” Now he just had to get his diaper leaking sooner rather than later or his bottom was going to be awfully sore!
Two minutes later, Mel yelled back again. “Are you leaking yet?”
“No, Mistress.”
“Did you curtsey again?”
Darn it! He should lie for sure! “No, Mistress.”
“That’s another one for later! Sissy…”
This time Chad remembered to curtsey. “Yes, Mistress.”
“Did you just curtsey?”
He curtseyed again. “I’m curtseying every time now.”
“Good. Keep doing it,” Mel called back. “I’m getting hungry. Can you whip me up a nice chicken salad while you’re trying to leak?”
Chad curtseyed. This was so dumb! She wasn’t even anywhere where she could see him! “Yes, Mistress!”
Mel didn’t exactly laugh out loud, but she was highly amused. She stared at her laptop. She was supposed to be working, and she supposed she was working, but she was only marginally getting anything done. She was having too much fun with Sissy instead. Curtsey, curtsey, curtsey. It was so silly. And absolutely the perfect thing for a sissy to be doing – she thought anyway. And even if it wasn’t, she absolutely loved seeing him do it all the time, so it didn’t really matter. All that mattered was what she wanted.
She briefly wondered if she could ever get him so paranoid about curtseying all the time that he’d actually do it at work too – without thinking about it. She guessed it was possible, but since she couldn’t be there, then she would have no way of knowing. Unfortunately, that thought led her to think about Robin. It was such a shame that she had told Robin the truth about Sissy. Things had not worked out well at all as far as that was concerned. And now Sissy was worried about his job. And she guessed that he should be. It was possible that by Monday he wouldn’t have a job anymore. She had really messed up! Big time, as they say. But that was water under the bridge now. Now they would have to deal with things as they came up.
Her current thoughts completely ruined her happy mood. Tomorrow would just have to bring what it brought. For now, she would concentrate on enjoying Sissy as best she could. And tonight… Well, she was very much looking forward to tonight. Tonight should be… interesting!
“I’m leaking!” Sissy’s voice suddenly called from the kitchen.
It was about time! She glanced at the clock as she called back. “Did you curtsey again?”
His reply was a bit delayed and much softer… “No.”