The Bet - Chapter 27 (Thursday – week 4 Part 5 of 6)

The Bet
by Karen Singer

Chapter 27 (Thursday – week 4 Part 5 of 6)

As per Mel’s usual instructions for Thursday evenings, Chad headed straight to her office after work. Andrea actually gasped a bit as he walked into the office. “Well, don’t you look pretty good today,” she commented.
“Thanks,” Chad mumbled, he was a bit embarrassed by her compliment. There were several other people in the office, all of them staring all too interestedly at him. They were making him uncomfortable.
Fortunately, Andrea got right up from her desk. “Let’s get you out of here,” she suggested. Chad followed her back to the usual vacant, but richly appointed office. “You’ve got another bottle yet?” Andrea asked.
“Yeah. Right here,” he replied holding up his pink diaper bag.
“I’ll leave you to it then,” she replied as she closed the door and left him alone.
Chad pulled out the one remaining baby bottle that was still full from his diaper bag, stretched himself out on the comfortable leather couch, and put the bottle to his mouth. His thoughts were far away though as he laid there drinking. Jumbled images ran though his mind. Particularly, he thought about his short encounter with Derek earlier. He felt particularly bad now about everything. Why was he doing all this? The words self-respect, friends, and a life crashed into his brain. That was why he had to win this bet.
But on the other hand… he sighed around the nipple in his mouth as he paused in his drinking to let some air back into the bottle. On the other hand, he was actually living his dream. For real! Unbelievably! Who would have ever thought… Even he hardly believed it. And as much as he wanted to win the bet and all the things that came with winning, he wanted to lose just as much – along with all the things that came with losing.
He could literally feel his sexual need. It had changed over the last month. While it always raged, at times it was starting to move more into the background where he didn’t notice it as much. Sometimes he was almost comfortable with it. But always, he actually enjoyed it. The big problem however, was that he really did want some sexual relief! No matter how much into the background it moved at times.
His baby bottle startled gurgling as he finished the last of it. He put it back into his diaper bag and laid back on the couch. He was living his dream. Yet he wanted his self-respect back too. Which way should he choose? They both called strongly to him. His encounter with Derek filtered back through his mind again, along with how bad he felt about it. Derek was his friend… scratch that! Derek used to be his friend! Not anymore. He didn’t have any real friends anymore. Self-respect, friends, and a life! As much as he wanted his dream, it was too difficult. He had to win this bet!

Mel sat at her desk and leaned back in her chair. Chad was waiting in the next office for her. Andrea had just left for the day. She needed to go in and change Chad’s diapers so they could go and get some dinner before going to see Gloria. But her problem was what Cassie had told her earlier about how Chad had behaved at the gym. Was it wrong? She really wasn’t sure. And then there was the other question that Cassie had brought up, just how much authority should Cassie have over him?
She glanced at her clock, it was running late. Her last few clients had taken more time than she thought they would… a common occurrence. But now she had to deal with Chad… or rather Sissy. Should she punish him? Or was he right in the way he had acted? She just didn’t know. She wasn’t one of those professional dominatrix women she had read so much about lately. They always seemed to know how to deal with everything. She wasn’t a dominatrix, she was a lawyer. This was all new to her. And as much advice as she tried to pick up from the web, she was mostly just winging it on her own.
So what should she do about him? Having no answer, she decided to put the decision off till later. She got up from her seat and headed toward the door to her office. She was going to have to hurry now and changing his diapers was going to take a few more precious minutes. Change his diapers! Yuck! But it was a small price to pay for gaining her dream. She paused as she placed her hand on the door handle leading into the office where Chad was. Should she go ahead and start looking for a house to buy? It was obvious that he had already lost. Maybe she should. There was really no reason why she should put that off any longer.
With a smile, she opened the door to go in and change Sissy’s diapers.

The restaurant was their usual one. Chad did notice however, that this time, the staff didn’t seem to give him as many of their overly curious glances as they usually did. Was he becoming less of a curiosity? The glances he was getting from some of the other customers however, still made him very uncomfortable. He was a bit surprised, not to mention pleased, to notice that Mel didn’t even pull one of his empty baby bottles out and put it on the table – to taunt him. Instead, she just ordered both of them a cup of coffee when the waitress asked what they wanted to drink.
“So how was your day?” Mel asked as they waited for their coffee.
Chad rolled his eyes. “Miserable!”
“Why?” she asked with some surprise.
“I ran into an old friend today. It was the first time I’ve talked to him since this all started. It was very awkward… to say the least.”
Mel nodded. She could only imagine what it must have felt like for Chad… yet strangely, she didn’t have much sympathy for him. This was his dream after all. “And that made your day so miserable?”
“Mostly,” Chad replied.
“So there were other things then?”
Chad shook his head. “Oh, a lot of little things, I guess.”
“Like what?”
“Well… I got felt up today by Robin, for one thing.”
“You what?”
“She can be so conniving sometimes! She started out by complementing my figure, and the next thing I know, her hands were all over my breasts! Damn the woman!”
“Don’t swear!”
“Sorry,” Chad replied contritely.
But Mel was trying to figure out how she felt about Chad’s latest encounter with Robin. On the one hand, Robin was obviously getting more physical with him. But on the other hand it sounded like Chad wasn’t all that happy about it. While she was very annoyed with Robin, she decided to put that on her list of things to think about later too. “Anything else?” she finally asked.
“Ugh!” Chad grunted. “Just the usual mess I guess. All the women at break spend too much time talking about me. And they’re all after me to get my ears pierced now.”
Mel’s attention was suddenly completely on Chad and that situation. Unfortunately, that was when the waitress brought their coffee. Mel ordered Chad his usual huge steak, but she only ordered a chicken salad for herself. There was no way she was ever going to let herself get fat! Finally, the waitress was gone and they could talk again. “So what do you think about getting your ears pierced?”
“I don’t really know. On the one hand, it is kind of exciting. I mean, most women have their ears pierced, don’t they? And I have no doubt I’d probably feel embarrassed as hell about it.”
“Careful with your language!” Mel cautioned.
“Sorry… And I guess earrings would help make me look a bit more feminine… maybe anyway.”
“Maybe,” Mel agreed.
“But… Well, I don’t know that they’re really necessary. And then once I have it done, it would stay done. And when I win this bet, then what would I do?”
“When you win? Aren’t you jumping the gun a bit?”
Chad shook his head and smiled wickedly at her. “I’m not going to lose!” he said overly dramatically.
“We’ll see about that,” Mel returned with a sinister tone in her own voice. They both laughed, but Mel was very conscious of the fact that Chad still didn’t think he could lose. At least not that he was admitting yet. Why was that? “So what are you going to do?” she asked.
“About what?”
“Earrings.”
“Oh. I don’t know. Shouldn’t that be your decision?”
Mel thought about that for only a moment. Actually, this was falling right in line with her plans for him. “No, I don’t think so,” she replied. “I think you should decide. I’m going to leave that totally up to you!”
Chad was surprised. Up to him? Now what was he going to do?
Mel stared at him. He obviously had a dilemma to figure out. But by making him decide what to do, it was more like he was now feminizing himself instead of her doing it to him. She wanted him to get to the point where he was pushing himself, adding his own humiliations, not just her. And obviously, he was starting to get there. That tiny spark of progress made their dinner much more enjoyable to Mel.
When their meals finally arrived, Chad dug in quickly. He was famished and the steak was great. Mel almost laughed at the look of pure enjoyment on his face the moment he took his first bite. But Chad’s fast eating didn’t last long. Mel was actually very surprised when a short while later, he looked at her with a pained expression on his face. “I can’t eat another bite,” he complained.
Mel looked at his plate. More than half his steak was still there. “What’s wrong?” she asked with total concern.
“I’m too full!”
“You’re full?”
“Yeah! Well, with all the baby food you’ve been making me eat lately, and now this darn waist cincher squeezing my stomach, I can’t seem to eat as much as I could before.”
“You can’t?”
“Chad shook his head.”
“So you’re going to waste most of your dinner?”
Chad looked really crestfallen. “I hate doing it. It really tastes great. But I just can’t eat another bite!”
“That’s all you’re going to get tonight. So if you can’t eat, then you can’t eat.”
While Mel finished her dinner, Chad sat and just sipped at his coffee while they talked. He tried to take a few more bites of his steak, but his stomach just felt too full to eat much more.
“So is it tomorrow that your divorce will be final?” Mel asked at one point.
Chad set his coffee cup down. “Yeah,” he admitted. “I’ve been trying not to think about it.”
“Is it bothering you?”
He shrugged. “A little… maybe more than a little. Like I said, I’ve been trying not to think about it.”
“How come?”
He let out a big frustrated sigh. “Because I’m such a failure! It’s all my fault!”
“Do you really think you’re a failure?”
“Well, look at me!”
She shook her head. “I don’t think you’re a failure at all. I just think that you and your wife couldn’t come to an agreement over your desires. That’s all.”
“Ex wife!”
She nodded, slightly amused. “Ex wife. Under different circumstances, I think that the right woman would be lucky to have you.”
“Yeah right!” Chad replied, obviously not agreeing at all.
“So do you want to celebrate it tomorrow? Some people are glad when it’s all over.”
He shook his head. “No. I’m really not happy at all. I’m just trying to forget it and move on with my life instead.”
She nodded her head again. “Moving on sounds like a good plan. I’m not so sure about forgetting it though.”
“It hurts to think about.”
“You loved her?”
“I guess so.”
“You guess so?”
“I know I did once. It’s just… my stupid, fucked up, sexual needs! I can’t control them. And she couldn’t accept them. So all we did was to argue and hate each other over them. In the end, I think I started hating her. She just couldn’t understand. Nobody can.”
Mel very much wanted to say that she was trying to understand. But she let it go unsaid. A few minutes later though, as she was paying the bill, she took one last glance at the huge amount of steak still left on his plate. Under any other circumstances, her comment would only have caused scorn and resentment, but in this case, it was probably one of the few things to take Chad’s mind off of his troubles. She put a sly smile on her face as she said, “Maybe we should be ordering from the children’s menu for you from now on!”
Chad blushed furiously. He could only imagine how humiliating it would be to have to order all his meals out from a children’s menu – from then on.