The Bet - Chapter 50 (Saturday – week 7 part 1 of 10)

The Bet
by Karen Singer

Chapter 50 (Saturday – week 7 part 1 of 10)

It was the vision she had seen several weeks ago now – the vision of Derek kissing Sissy. A kiss so filled with passion it made her hot and tingly all over. The kind of kiss every woman yearns for. Yet he had only kissed… Sissy.
But her dream was able to take things further than real life ever could. In her dream, Derek turned away from kissing Sissy, his lips smeared horribly with all the lipstick she had made Sissy wear. Derek turned towards her. His eyes locked onto hers… and she felt weak. Helpless. There was something about the power of his gaze that riveted her. And then he was there, standing right in front of her, looking only at her, only into her eyes. His deep eyes… looking deeply into hers.
He reached out and grabbed her, tenderly, yet powerfully. He pulled her into him, holding her tightly to his body... his beautiful, powerful body. Very slowly, he brought his head down to meet hers. He kissed her lips, first softly, then stronger and stronger, more and more passionately, till she was writhing in his arms with desire. It was the same kiss he had given Sissy, only more so. A kiss that she could feel as much in her wet and aching sexual zones as in her lips. He seemed to be all hunger and need, just like she was. And when that kiss finally ended, he continued to hold her tightly to him, staring down into her eyes.
Ray and Sissy evaporated into nothing as he turned her toward her apartment, and led her slowly toward her bedroom… and her bed. He scooped her up in his arms and laid her down on top of her bed, ever so gently, and still fully dressed. Then he climbed on top of her and slowly began removing her clothes. His touch was so careful… so sensual! She writhed with pleasure as he released each fastener, removed each piece of clothing. She wanted him so much.
She was naked now, yet he was fully dressed. His hands played tenderly over her body, igniting feelings she had rarely ever felt in real life. Feelings that made her whimper in her sleep. And then he let go of her and grabbed his shirt and ripped it from his body. Somehow, that single motion removed every stitch of clothing he had been wearing so the two of them were naked on her bed – together. He had such a beautiful body, muscular and smooth. And down below, where it counted, he was just as impressive… and erect.
Ever so slowly, he brought his body back down to meet hers, but not putting any of his weight on her. Her nipples just barely touched his chest as he began sliding his body back and forth against her. Very slowly, he increased his weight on her, lowering his body down… down… till he was fully on her. And that’s when she felt his hand reaching down… down… between her legs, opening her up, making her ready – which she was. More than ready. She hungered for him.
She felt him lifting his hips, guiding his turgid manhood into her. And with one powerful thrust of his hips…
Her alarm buzzed, crashing its way into her dream world. Ripping her away from a dream so intense it hurt. She tried so hard to ignore the intrusion… tried so hard to hold onto the Derek in her dream… tried so hard to hold on to the wonderful erotic feelings her body craved… But the ever invasive alarm would not be denied. It was too powerful to be ignored. Too powerful to let her have the few minutes more she so desperately wanted. With an angry slap of her hand, she turned the darn thing off. Such a great dream – ruined! What a lousy way to start the day! Especially when it had almost been so good!
She sat up on her bed, aware of how moist her sex was. Darn it! She got to her feet, grabbing her robe at the same time, and put it on as she headed out toward her kitchen, and her coffee pot. Coffee! She didn’t even have to think about it. It was a given. Still, it would be nice to have someone deliver a freshly made cup to her in bed. Sissy would be doing that very soon. She hoped. But five minutes… It seemed so impossible!

Very gradually he became aware of things. He was lying on his blow up mattress. The huge bulk of his soggy and messy diapers kept his legs splayed wide apart. Perhaps the biggest thing he noticed, not to mention perhaps the biggest pleasure, was that his ever present breast forms weren’t there. None! Not even the bra he usually wore to bed to support them as he slept. It would only be for the one night he knew, but still, it felt so good!
Without thinking, he shifted the pacifier in his mouth a bit to yawn deeply. Then his lips closed back around it again. And that’s when he realized that it was morning. But was it time to get up yet? His alarm certainly hadn’t gone off as it always did. He remembered that today was Saturday, but still… Mel always set his alarm for him. Since he was awake, he rolled off of his mattress, more carefully than usual, only knocking down one empty baby bottle in the process. He got to his knees and turned to look at his pink alarm clock. As far as he could tell, it was way past time to get up! He looked at the clock more closely. The alarm hadn’t even been set! And that realization brought a new worry to his mind. Did Mel leave him a note last night? It didn’t look like it.
He forced his way to his feet and waddled out of his bedroom to his kitchen. Relief washed over him the moment he saw the little piece of paper there. So why hadn’t she set his alarm?
He read the note.

Sissy,

Three bottles before you clean up. As usual, call me the minute you get your one diaper on. I’ll have more instructions for you then.

More instructions. He could pretty much guess what they would be. But still, why not just put it all in the note?
He didn’t even have to think about it as he went to his refrigerator to remove three of the bottles that should be there, but he stopped as his hand reached out toward the bottles. His hand… or more accurately, his fingernails! His crazy fingernails that now spelled out Sissy – one letter on each nail – both hands! It was… crazy! He dreaded anybody seeing it. How could anybody notice his nails and not know immediately what he was? It was so… embarrassing! Purposely turning his hands so he couldn’t see his nails, he reached in and removed three of the bottles from his almost depleted supply. He carried them to his chair where he sat gingerly on his messy padded bottom and started drinking the first one. How was he going to get away with nails like this? He couldn’t see any way possible.

Mel kept glancing at her clock. No call from Sissy yet! Maybe she should have set his alarm after all. In fact, she should have set his alarm and not set hers! She was still a bit miffed over being awakened at exactly the wrong place in her beautiful dream. Question – would Derek be anything like that in person? She looked forward to finding out tonight!
So why hadn’t Sissy called yet? She knew he was a very sound sleeper – very sound! And she often pushed him fairly hard every day. She had worked with his little ballet till late last night again too. So the guy probably needed a little sleep. But still, he should be up by now!
She grabbed her phone angrily and dialed his number – and listened, and listened to it ringing without being answered! Where the hell was he?

Chad was in the shower when he thought he heard his phone ringing. He stuck his head out to be sure. Yes, darn it! The sound was heavily muted since his phone was in his purse, but he couldn’t mistake that ring. Dripping wet, he hurried for his purse to find his phone. He heard it stop ringing long before he got to it. Breathlessly, he pulled it out and checked to see who had called. Mel of course. Who else? He quickly dialed her number. “Hewwo Mithtweth,” he said in his sissy voice.
“Sissy! Where were you, still in bed?”
“No Mithtweth. In da showa.”
“Well, what’s taking you so long? I expected to hear from you long ago!”
“I slept late,” he replied in his silly sissy voice. “My alarm wasn’t set.”
“I know. I purposely didn’t set it. I was trying to be nice for a change, but I didn’t think you’d sleep this late!”
“Sorry, Mis… Oh shit!” he suddenly exclaimed. He had started to say he was sorry, when he noticed he was peeing on the floor – almost on his purse.
“What was that?” Mel asked angrily.
“Um… Sorry Mistress, it’s just that I… well… I just almost peed on my purse. Fortunately, it’s only on the floor and I can clean it easily.”
Mel almost laughed as the anger seemed to drain right out of her. She could just imagine! “Well, hurry up then,” she replied. “I’ll be expecting another call from you in a few minutes as soon as you get that diaper on. And don’t get dressed yet!”
“Yes, Mistress,” he said – into an already dead phone. He stared down at the puddle of pee at his feet. Geez! Why did it have to happen now?

Mel carried her phone with her as she headed back into the kitchen to pour a fresh cup of coffee. He had peed on the floor! And obviously, he hadn’t known he was going to do it! She really wished she could have been there to see it. Once again she had been left out – even if he was alone this time. But still, right now, that one sign seemed encouraging as far as their bet went. But she also knew that overall, it probably didn’t mean much.
She chuckled a bit again at how surprised he had been when it happened. Not to mention how bothered he probably was over having to clean it up. She stopped as an odd thought struck her. No, it was a totally dumb idea! Totally! But… Darn if she wasn’t going to try it later! At the worst it would be fun to watch!
She figured that by now he had to be getting ready to get his diaper on. With her phone in one hand and her cup of coffee in the other, she grabbed her keys and headed out the door. Her phone rang just as she was about to put her key into his door lock. Instead of answering it, she pushed his door open. She saw him standing not far away, his purse on the floor in front of him, his cell phone in his hand. “Don’t bother,” she said, “I’m already here.”
As she walked in, she could see where he had peed on the floor. It still hadn’t been cleaned up.
“Um…,” he said embarrassedly, “I haven’t had time to get that yet.”
“Don’t worry about it, you can take care of it in a few minutes,” she said as she headed straight for his bedroom.
She didn’t really like seeing the breast forms not glued on him, but it was starting to get late and she didn’t want to take the time to glue them on right now. In his bedroom, she went directly to his cheap set of cardboard drawers and opened the top one. Fortunately, it held just what she hoped it would. She pulled out one of his bras and handed it to him. She pointed at the forms that were lying on the floor nearby. “Don’t forget those.” As he was putting them on, she searched two more drawers before she found what she was looking for – jumbled in amid his many pairs of pantyhose. As soon as he was ready, she handed him a pair of his white sissy socks with pink lace around the top. She didn’t bother watching him put them on but went straight to his closet instead. There she pulled out his pink patent leather high heels. She had to hold them in her hand for a minute till he was finished with his socks, then she handed them to him. “When you’re ready, you can clean up your mess in the other room. Then drink another bottle and fix your makeup and hair. Don’t wear anything else. Bring all your empty bottles to my place as soon as you’re ready. I’ll see you there. And hurry up. We have a lot to do this morning!” She left him without another glance and went straight back to her apartment.
It was almost forty-five minutes before Sissy knocked on her door again. Actually, Mel figured that he had done fairly well to take care of all his makeup, hair, clean up the mess on his floor, as well as drink another bottle in that time.
As soon as their usual morning greeting was over at the door, Chad followed her straight back into her bedroom. Earlier, when she had handed him his frilly socks and told him to wear his pink patent heels, he had been afraid of what she wanted him to wear today. Last week she had made him go to the drug store wearing his pink baby dress. That had been horrible! Was she going to make him wear it again today? He certainly hoped not, but it was starting to look more and more like it.
He waited as she went into her closet. She pulled out his pink baby dress and held it up to look at it. His heart cringed more than a bit at the sight of it – especially when she laid it down on the bed. But then she went back to her closet again and pulled out his blue sissy dress. Was she going to switch this time and make him wear that one instead? But that dress also went on her bed on top of the pink one. She went back to her closet one more time, and brought out the last of his silly sissy dresses, the white one with the pink bodice. The one with so many ruffles that the skirt stood almost ridiculously straight out!
“Here,” she said as she handed it to him. “You can wear this one today.”
The dress was practically torture since it was loaded with ruffles all over. Would she really take him out in public wearing this monstrosity? Unfortunately, he knew the answer to that one was a big yes! She had taken him out wearing the baby dress last week, so he figured that Mel wouldn’t consider this one any worse at all. His hands were shaking a bit as he reached out to take the dress from her. But now he still had to get the darn thing on.
It had been a long time since he had last worn it, but the moment he started to pull it on, he quickly remembered the main problem with the dress – there were so many darn ruffles that the whole thing seemed to be alive! Every tiny little movement of his body seemed to translate into a bigger movement of the skirt – that was so full it stuck straight out. The satin material of the dress itself felt sensual against his skin, but it was nothing compared to the mounds and mounds of very soft ruffles that were layered over it and also supported the ruffled skirt as well. Ruffles that didn’t allow it to remain stiff, but instead let it move and sway all too sensually. The whole thing was a nightmare! And worse, once he had it on, the skirt stuck so far straight out that he couldn’t tell if it covered his diaper or not. And he had no way to tell one way or another. If he tried to reach down with his hand, he had to push the skirt down as well, so that didn’t tell him anything! Nightmare didn’t begin to describe the crazy thing.
Mel shook her head. “Why have we let that thing just sit in the closet for so long? I love it! I think it will be the perfect outfit for you today. Especially with everything we have to do.”
Chad didn’t love it. He was still trying to picture himself going out in the stupid thing. And worse, he was starting to worry about his darn chastity device hurting him again because of it! So far, so good, but he hadn’t taken more than two steps in the dress yet! What would happen when he had to keep moving?
Mel looked him over critically and smiled. Perfect! “Okay, Sissy, grab those clothes from the bed and get your purse. We have things to do and places to be.”
Just walking to the bed made his skirt swish back and forth alarmingly. As he picked up the two sissy dresses, he wondered what Mel had in mind for him today. Why would he need all three dresses? He followed Mel out to the living room where she was just checking his diaper bag. He saw her close it and pick it up herself.
“Grab your purse and let’s go,” she said just before she opened the door and walked out.
Chad paused a moment for courage. He was going outside in the silliest dress he could imagine – carrying two more dresses just as bad in his arms. He had to force himself to step out through her door – and close it behind him. Outside, in a mountain of ruffles, with more ruffles filling his arms. What a nightmare!