The Bet - Chapter 20 (Thursday – week 3 Part 1 of 5)

The Bet
by Karen Singer

Chapter 20 (Thursday – week 3 Part 1 of 5)

In her dreams, she was a horrible monster, a Doctor Jekyll and Mrs. Hyde, whose split personalities were constantly at odds with each other. Part of her tried so hard to be kind and loving, while at the same time, the other half of her was committing atrocious acts of evil - acts that she delighted in completely.
Her two halves battled for control, but more and more the evil half was winning. They were disturbing dreams – more so because she realized that even in her dreams, the evil held a distinct fascination for her. She felt confused, unable to help herself. Do one nice thing for someone, then turn around and do two things that were cruel! Over and over again. She hated it… she loved it… Evil wasn’t what she wanted to be, yet she continued to commit act after act of cruelty - and she laughed at each one!
Her alarm clock buzzed a long time before she came fully awake, chasing the evil dreams away, erasing them from her mind – fortunately. She didn’t even bother throwing her robe on as she went into her kitchen. She only knew that she needed coffee. Was she becoming addicted to it? She didn’t really care. She just wanted a cup to clear her brain!

Chad’s whole body jolted awake at the sound of the loud music blaring into his room from his pink clock radio. God! Morning already? What had happened to the night? It felt like he had just fallen asleep.
He rolled over and struggled to his feet. His diapers were over-loaded again, not just from wetting them, but from the damn suppository that Mel had stuck up inside of him. A horrible mess. He barely remembered waking up when it happened last night. But then he had to stop to think… he didn’t remember waking up at all for anything else. Not once. Yet his diapers were soaked to overflowing. That was a troublesome thought. For the second day in a row now, he had woken up with soaked diapers and not once during either night did he remember wetting himself.
As much as the idea of it thrilled him, it was going to cause him trouble with winning the bet. But he didn’t know what he could do about it. He had to sleep at night… and Mel’s stupid bottles of tea kept him peeing all too frequently. It was too early to wrestle fully with that problem. He headed to his kitchen to see if she had left him a note.
It was there, on the counter where he hoped it would be. His heart soared a bit at seeing it, even though he really didn’t care much about what was in it. She had cared enough to leave it for him and that was all that mattered.

Sissy,
First bottle.
Shower and shave (don’t forget your legs – I’m not going to mention it again).
Second bottle.
Get dressed.
Third bottle.

Nothing. Nothing really at all. He realized now why she had stopped leaving the notes before, he no longer needed them. Yet he wanted them. For some unknown reason, they were important to him. Even notes like the one she had left for him today. He grabbed his first bottle and headed for his lonely chair to sit and drink it.

As Mel’s coffee began to kick in, so did her thinking about Chad and what had happened last night. Certainly not what she had intended. With her robe finally wrapped around her, she sat with her coffee in one of her living room chairs and pulled her legs up under her. She took another sip and leaned her head back. What was she going to do about him? That was her ultimate question. She pretty much knew what she wanted from him, but she knew more than ever now that even this kind of relationship was a two way street - perhaps even more so than a normal relationship. A relationship? Could she call it that? Yeah, it was a relationship for sure, just a type she had never thought of before.
A week ago she had begun training him to never get hard so he could pee whenever the need hit him. She had really loved the unintended consequences of his being denied the basic ability to receive any pleasure at all – while she herself received all the pleasure. She smiled at the thought. It really was deliciously wicked – yet she loved it. But last night she had purposely tried to stimulate him, ok, she had left the damn device on him so he couldn’t get hard just to see how he was really reacting to the anal play, and she had wound up ruining his ability to have an orgasm. She hadn’t meant to and she felt really bad about that – especially since she had promised him. Yet the fact that he couldn’t orgasm still held a fascination for her. What did she really want?
She realized that as of last night she was sending him mixed signals. That was never good – no matter how you tried to justify it. Mixed signals… not good… why was she doing it? She took another sip of her coffee. Why? Why? Why? That was always the one big question in her life. With Chad, there were lots of reasons why… too many. And that was part of her problem this morning, too many reasons and too many thoughts about Chad… all of them leading back to her original question. What did she, herself, really want with him?

Chad faced his closet door, afraid to open it. Before, when he had started wearing the women’s pants and shoes, Mel had taken their male equivalents away from him by wrapping them up in layer after layer of her cling wrap. Yesterday he had worn a blouse to work for the first time. Would his male shirts be taken away now? He hoped not. He hadn’t noticed any more of her cling wrap in his closet after work yesterday.
He opened the door and looked in carefully… and breathed a sigh of relief. All his male shirts were still hung up where he could get at them. Yesterday had turned out to be a nightmare after he had decided to wear the blouse. How was he supposed to know that the blouse he had selected needed that much padding in the cups of his girdle to make it look right? Ok, he should have realized it easily, but he hadn’t.
Because he could, he pulled down one of his male shirts to wear and put it on - he wasn’t going to make the same mistake he did yesterday. But then he turned to his pants – women’s slacks. He had only one pair left in his closet because all the rest were in Mel’s laundry hamper. This pair was his new pair - the slacks with the longer length. As he pulled them on over his diapers and pantyhose, he noticed that they were way too long, he was standing on the bottoms of them. He slipped his low heeled shoes on and took a few steps. He quickly felt a slight tugging at his pants as his heel caught under the bottom of them. They were still too long for the shoes he was wearing.
He knew it would happen. It was why he had avoided wearing the new slacks before. They had to be worn only with higher heels… much higher heels. Having no other choice, for the first time, he put his low-heeled shoes back into the closet and selected a pair of his highest heels to wear to work because they were the only ones that would keep his pants legs from dragging on the ground. It felt like he had lost something again. It also felt a bit like when he had put the blouse on yesterday, like he was taking a huge chance by doing it. Was he?

Mel watched the clock, waiting for Chad to arrive. By her estimation, he should have only one pair of slacks left in his closet, the new ones. Would he be wearing his higher heels today? And how about a blouse? He had worn one for the first time yesterday. And for that matter, how about padding the cups of his girdle… and his makeup? Too many questions. Fortunately, there were only a few moments more till she would have some answers.
The knock came at her door only a few seconds late. She opened it. “Good morning, Mistress,” he said as he dropped his accustomed curtsey.
She took in the entire sight of him quickly. Her face fell just a bit at the sight of his male shirt – but then she had a strong feeling that he would choose one today. “Good morning, Sissy,” she replied and stood back out of the way to let him in. She quickly noticed his new slacks, the heels on his feet, and the makeup on his face. She instantly felt better.
When she had closed the door, she took the bag of empty baby bottles from him and checked it – perfect, but then she didn’t expect anything less. She turned her sight on him and started looking him over carefully. “It’s about time you wore those slacks,” she commented, trying hard to hide her amusement. He made no reply.
For the first time, his makeup was fully done and actually looked pretty good. Maybe Sandy didn’t need to teach him anything else. His male shirt was an obvious disappointment as was the lack of breast padding, but then she had never specified either of those for him. Those things were still his choice… but for how much longer? His jewelry was all in place and his hair was neatly combed – she made another mental note to talk to Cassie again about teaching him to fix it better, maybe tonight.
Everything about him was perfect – except for one thing. “Where’s your pacifier?”
He rolled his eyes. “I’m sorry, Mistress,” he said as he dropped another curtsey. “I forgot it again.”
She shook her head. “One of these days I’m going to remember to punish you good for forgetting it so much… maybe one day very soon!”
“Yes Mistress,” he replied with yet another curtsey.
“Come on, Sissy,” she said as she turned toward her kitchen. “It’s breakfast time.”
Chad set his purse and diaper bag by the front door and followed her. She walked straight to the highchair and pulled the tray off and waited for him. He stopped for a moment and stared at the chair. Ugh! He hated the thing – yet at the same time, he loved it! It was so demeaning to have to sit in to eat from, while at the same time, it fueled all too well his unrelieved fantasies. Having no other options, he climbed up into the chair and held his arms up out of the way while Mel replaced the tray.
A moment later, she fastened the bib around his neck. Wasn’t it nice of Sandy to get you this pretty bib?” she asked. “I should have gotten you some before. I think it’s much better than that nasty old dish towel we were using.”
He looked up at her and rolled his eyes slightly looking for a reply. But he couldn’t think of one that would keep him out of trouble so he said nothing. A minute later, he was spooning awful tasting baby cereal into his mouth with the tiny rubber coated baby spoon.
Mel stood back by her sink and watched him eating. It was so much more rewarding seeing him eating now in the highchair and wearing the bib instead of having him sit on the floor. He looked all that much more ridiculous… and she loved it. She didn’t really like being a cruel person, but damn it, they were his fantasies! She just happened to enjoy being on the other side of them.

Robin hurried into work, technically a few minutes late – not that anyone would really care or even notice. As she hurried past Chad’s desk, she quickly noticed that he was still booting up his computer, so he hadn’t been all that early either. “Hi Chad,” she called as she hurried to her own desk.
She dumped her big bag on her desk and pulled out her mirror to check her hair. She touched a few strands and returned her mirror to her bag and crammed it into her bottom desk drawer. She hit the power button on her computer so it could start booting up. While she waited, she wandered over to Chad’s cubicle. “Hi Chad,” she said again as, this time, she stopped for a minute to talk.
Chad turned around in is seat and smiled. “Hi Robin. How’s things today?”
“Ugh! What a morning! The baby was up all night crying. I think he’s coming down with a cold. He was a real handful this morning!”
“Oh,” Chad replied. “I’m sorry to hear that. Did you still take him to daycare?”
“Yeah, I don’t think he was all that bad this morning. I just hope I don’t get a call from them later.” She looked at him quizzically. “Hey Chad, why aren’t you wearing a blouse today? You’re back to your old stupid male shirts again.”
Chad looked down at his shirt and shrugged. “After yesterday, I thought this was a lot better. Besides, I don’t have to worry about how much to pad my breasts.”
Robin laughed. “Ok, you’ve got a small point there, but it still looks dorky. Your makeup looks good today though. Much better, and new shoes?”
Chad looked down at his feet and stretched his leg out a bit, showing more of his high heeled shoe. “Not really, just different. I’ve had these a while.”
“You have?”
Chad blushed. Without meaning to, he had just confirmed that he had been into cross-dressing for a while now. “Yeah, sort of,” he admitted sheepishly. “I had to wear these today because the pants I have on are too long without them.”
“Stand up and let me see.”
Chad got out of his chair and stood so she could see better. “I think I’d be happier with these pants if they weren’t so long.”
“No, they’re perfect. Very much in style. Have you had the pants for a long time too?”
“No, I got these last weekend.”
Robin nodded. “Let me see you walk a bit so I can see it all better.”
Chad didn’t really understand why, but at least she wasn’t being too pushy today, just nice. He took a few steps out into the hallway, thankful that it was all carpeted, then walked back into his cubicle again.
“Yeah, they’re really a good length with those shoes,” Robin stated, still watching his feet. She looked up at his face and smiled. “I see you really don’t have much trouble walking in them. You must have had them for a while.”
Chad blushed again. “Yeah, well…”
Robin chuckled a bit. “It’s ok, Chad. I just wish you’d finally come out and say that you’re doing all this because you like it and want to… instead of all this ‘it’s complicated’ crap!”
Chad sat back down in his chair. “Well, that’s just it, Robin. The reason I’m really doing it all is complicated.”
“So explain it to me.”
He shook his head. “I can’t.”
Robin just shook her head and rolled her eyes. It was time to change the subject. “Hey, so have you heard any feedback on our project yet?”