The Bet - Chapter 24 (Monday – week 4 Part 2 of 5)

The Bet
by Karen Singer

Chapter 24 (Monday – week 4 Part 2 of 5)

As Chad drove to work, his thoughts once again turned to his upcoming divorce. It would be final on Friday. Everything would be over completely. Irreversibly over. Yet wasn’t it really that way right now? And would he go back even if he could? He knew the answer to that one easily… no. A great big no! And how could he even think about going back – locked in this battle of the bet. What would his wife – make that ex-wife – think if she could see him now? He wasn’t wearing a single thread of male clothing at all… to work no less… and then there were the diapers he was wearing under everything else. No, going back to his ex-wife wasn’t an option he would even consider… especially not now.
He was probably better off anyway. He was a sissy. He had to accept that. And Mel was hammering that fact into him more and more every single day. He hated it… but he loved it too. It was because he was a sissy that his marriage hadn’t lasted – so there would be no going back. He was a failure as a man. A very depressing thought. Very depressing! Actually, he was a failure because he wasn’t a man… not really. He was a sissy instead. A damn sissy! And a failure! Failure! Failure!
Felling very depressed about himself, he turned into his company’s parking lot and found his usual parking space. He turned his engine off and just sat there for a few moments. Failure! All because he wasn’t a real man. All because he was a sissy. He hated it… and yet, he didn’t really want to do anything about it either. All the things he loved most in life… were the sissy things. Even all the humiliations. Deep down, he loved them. Only the sissy things made him really feel alive. Why? Why? Why? There was no answer. No solution. And because of that, he was a failure.
He was startled by a knock on his car window. He looked up to see Robin standing there. He finally opened his car door as she stood out of the way. “Good morning, Chad,” she said as soon as he opened his door.
“Morning, Robin,” he replied as he stuffed his keys into his purse before picking it up.
“Are you alright?” she asked. “I saw you just sitting there.”
He looked up at her briefly before he got out of the car. “Yeah,” he replied. “Just feeling a bit sorry for myself today. That’s all.”
“Why?” she asked as he climbed out of his car. “Because of something you’re wearing today?”
He thought about that for a moment as he closed and locked his door. “No. Not really. I think it’s just that my divorce will be final later this week. It’s just a bit depressing.”
“Ohhhh. You poor thing,” she said. “Yeah, I guess that would get me down too.” Before Chad could take a step toward the building, she linked her arm through his as if to give him whatever support she possibly could and together they walked, arm in arm, toward the building. “You look nice today,” she said as they walked.
“Thanks,” he replied. “I guess.”
“What do you mean… you guess?”
“I guess… I’m not used to people telling me I look nice. Especially not while dressed like this.”
“Oh. Then I guess I understand. But you do look nice. I see you’ve got bigger breasts today. Much bigger.”
He looked down as he walked. What could he say about that? It wasn’t by his choice. “Yeah,” he replied, “they’re breast forms this time.” He didn’t want to say anything else about them, but a funny thought struck him a moment later and he couldn’t resist mentioning it. “I’m getting very attached to them.” He actually chuckled a bit.
Robin took his comment totally different since she didn’t know his forms were glued on. “Well, I guess that’s good then. They do look good on you. Much better than whatever you were doing before. So are you starting to come out of your funk now?”
He smiled. “Yeah, I guess so. Somewhat anyway.”
“Good,” she replied as she finally dropped his arm. “Because we’ve got to finish this proposal today. Not that I know how you’re going to be able to do anything with those whopper nails you’re wearing! Why the heck did you get them so long? How are you going to type?”
Chad held up his nails to look at them. They still looked like huge claws to him. “Robin, I don’t know what I’m going to do with them today. I’ll just have to do the best I can.” He stopped at the entrance to his cubicle, still staring at the super long nails on his hands and shook his head. “You wouldn’t believe what a nuisance they are!”
“Yes I would believe it! Why the heck did you get them then? You had to know they’d be difficult to work with.”
He nodded and dropped his hands. “They weren’t my idea. Not my choice.” He turned into his cubicle, leaving her behind him.
“Mel? Your makeup lady?” she asked.
He use one of his long nails to punch the button that started up his computer and half turned around. “Mm hmm,” he acknowledged. Then he sat down with his back to her, wanting nothing more just then but to end a conversation he didn’t want to get any further into. He was glad to hear Robin leaving for her own cubicle.

Boring! Boring! Boring! Mel sat primly and tried to look like she was paying strict attention, but there wasn’t much to pay attention to. The judge was spending a lot of time reading everything over and was wasting everybody’s time. Typical of this judge. While she sat and waited, her mind wandered back to last night and how Chad had told her that she was beautiful. Then she wondered once again if his love making had been colder. He had honestly said she was beautiful… but was he colder about making love? Was that possible? She really had to wonder.
Logically, the bottom line for her was that she had gotten all the orgasms she wanted. But was that really the bottom line? He had said she was beautiful… well, he had said that he knew her body was beautiful… same thing! Every woman wants to be told that she is beautiful. But somehow, he had really touched her with the way he had said it.
And why should she care so much? He was a sissy! A damn sissy! It made no sense. She had gotten everything she wanted from him last night… physically. And him telling her she was beautiful was an added bonus. A big plus. But did he seem colder afterwards? Less into it? Did he try less than usual? She wasn’t sure. The more she thought about it, the more she thought that it just might be the case. Or was she wrong? She just didn’t know. And if he didn’t try as hard, should she do anything about it? And what did it matter anyway? She had gotten what she wanted… or did she? The fact that she was wondering about it now made her think seriously that she hadn’t gotten what she needed… even though she certainly thought so last night. It didn’t really make sense on any logical plane, yet to her, from her female perspective, it made perfect sense.
She glanced over at the opposing attorney and saw her roll her eyes over the judge’s slowness. She nodded ever so slightly in agreement. This was stupid, waiting all this time like this. She had better things to be doing. Her mind went back to Chad once again. She was suddenly convinced that he hadn’t been paying as much attention to her last night as he should have been. She would have to find some way to correct that. Because of this bet, ‘she’ was supposed to be the most important thing in his life. His needs and thoughts didn’t matter!
As she sat there brooding about that, she started getting angrier and angrier… even though she knew that it made no sense. She knew she probably wouldn’t have, if the judge wasn’t wasting so much of her time. She knew she was mentally taking her frustrations out on Chad, but then, wasn’t that something else he could be good for?
She hadn’t punished him in a long time now. Everything she had seen about him lately had been perfect… well, nearly… good enough anyway. Or was he? Was she being too lenient? Yeah, she was sure she was. Maybe what he needed was a good reminder of exactly who was the boss and exactly where all his attention should be! Tonight! Tonight, whether he liked it or not, he would get that little reminder. In fact, she hoped he wouldn’t like it! But then, he was a sissy. He’d probably get off on it. Well, mentally anyway. She had fixed him so anything more was completely out of the question. That thought sent a small wave of pleasure throughout her. He was a sissy! Nothing but a damn sissy! And she controlled him – completely! Tonight!

“Well, what do you think?” Robin asked.
Chad smiled. “It’s ready. More than most proposals we send. Let’s see what they think.”
Robin smiled. “That’s kind of what I thought. You want to do the honors?”
Chad opened his email program and with the tips of his long nails, awkwardly typed in Tom Robinson’s address – his nails making strange clicking noises with every key that he touched. Then he added a short note telling him that the proposal was ready for the client’s opinion. Then he hit the send button. “That’s it,” Chad said as he sat back.
“I just hope they don’t come back with too many changes to this thing.”
“They better not. This is one of the best sites we’ve ever done.”
“I agree,” she replied. She stared at his computer screen for a minute, then she looked down a him. “Now what do we do? We can’t do any more work on this till they approve it. I don’t have anything else on my desk right now either.”
Chad stared up at her. She was right. Neither of them had anything to work on. “I don’t know,” he admitted. “Strange, isn’t it?”
“Yeah.” A moment later, she brightened. “So, let’s go get some coffee and celebrate.”
Chad’s face brightened. “Good idea,” he replied as he started to get out of his chair. But then he quickly checked his watch and sat back down again. “Uh… It’s a bit too close to break time for me. I think I’ll stay here instead.”
Robin looked at him totally surprised. “So what? All the women there have seen you already. In fact, last week they saw you in a dress! What are you worried about? Come on, live a little!”
He shook his head. “No. I just can’t. Not yet.”
Robin shook her head and let out a loud grunt. “You’re just too stubborn for your own good! When are you going to get over this?”
He shook his head. “Not yet, I’m afraid.”
She shook her head and walked out. “Suit yourself!”
As soon as she was gone, Chad opened up the spreadsheet that he was using to track his progress in the bet. He really wasn’t all that sure about how long he had held things back over the weekend. For the most part he either hadn’t bothered to time himself, or he wasn’t able to time himself. Under yesterday’s date, he put down a conservative thirty minutes. He was sure he had lasted at least that long… at least at some point.
This morning was still another matter. He looked at the number of days to go… thirty nine. Thirty nine horrible days. The only good thing he could see about that number was that it was finally less than forty. For all the good it did… which was none. Because of all the baby bottles of her tea he had already drank that morning, he hadn’t been able to hold things back for more than ten minutes yet. But he knew that the time would improve as the day went on and more of her nasty tea got out of his system. He closed the spreadsheet, still disappointed with himself. He had to win this bet!
But now what could he do with himself? He had nothing to work on. Coffee did sound like a good idea, but everybody would soon be heading to the break room. There was no way he was going to expose himself to all the women there again. All they wanted to do was to humiliate him. He had enough of that in his life. He opened one of his desk drawers and spotted the magazines that someone had left on his desk last week. He pulled them out and began looking thorough one of them closely. Very closely. He swore as he looked through some of the pictures. Damn. He really wished he had a better looking body. He would love to wear some of the clothes these models had on. Women… how do they know what clothes to put together to make their outfits look so good? He really didn’t have a clue.
He read some of the articles. With nobody around to see him doing it, it felt like a distinct wonderful freedom. He not only found the articles interesting, he was really enjoying himself.
“Oh, that was a good issue,” Robin said from the entrance to his cubicle. “Did you get this week’s yet?”
Chad looked up with a sense of horror on his face. Robin had caught him looking at the magazine. Yet she knew about the magazines. There was no way to really lie to her about what he was doing. And she didn’t really seem to be teasing him at all – not yet anyway. “Ummm… No, I haven’t been shopping for magazines,” he said. “I was just board and found these in my desk.”
Robin disappeared for a moment but she was back very quickly, pushing her own desk chair into his cubicle. “Move over,” she said. “Have you seen the article in there on the new colors they’re coming out with? It’s really good. I love them. I can’t wait to see what actually makes it into the stores.”
“No, I haven’t gotten that far yet,” he replied as he moved his chair over a bit to let Robin put her chair right next to his. Actually, she didn’t seem to be giving him any choice.
She pulled the magazine out of his hands and began thumbing through it till she found the article she was looking for. “Here. Look at this.” She opened the magazine out wide where he could see the pictures she was talking about. “Aren’t they gorgeous? Most of these fall perfectly into my color pallet.”
Chad looked at the magazine and saw a whole page of lipsticks in many different colors. But what did he know about what he was looking at? Nothing! So he said nothing.
“What are you, an autumn?” she asked as she still looked intently at the lipstick picture in front of her.
“I don’t know.”
“You don’t? You’ve never had your colors done?”
“No.”
“Geez,” she replied as she went back to staring at the picture. “You really aught to consider having someone analyze your skin tones really soon.”
Chad sat back. Analyze his skin tones? It was something he had never really thought about before. He had heard about it of course, but had never seriously considered having it done. It was always something that would be too embarrassing. But now? Now that he was dressing as a woman? No. He still wasn’t ready for even that little step yet.
Robin turned a few pages in the magazine. “Oh. Did you see these?” she asked pointing at one of the pictures. “I just love those earrings. I wish I could afford them.”
Chad dutifully leaned over and looked. Diamonds. What else? Of course Robin loved them. He thought briefly about his own wife. She had loved anything with diamonds in them!
“Hey Chad. Why haven’t you had your ears pierced yet? I mean, you’ve done just about everything else. You don’t even wear clip-ons. And earrings would add a lot to the way you look. You’ve got to accessorize Honey.”
“I do?” Chad replied, more than a bit surprised.
“Of course, silly.”
He did? That was news to him. But then he wasn’t a woman. Not really anyway. He was a damn sissy - and even at that, it was obvious that he was still in the infancy stages of being a sissy. Speaking of infancy, the thought led him to thinking about his diapers. He almost chuckled. If she only knew! “Uhhh… I guess I never thought about it,” he replied.
Robin never even looked up from her magazine. “Well you should.”
While Robin looked through the magazine on her lap, Chad grabbed another one from his desk and opened it. What did he know about the things in these magazines… nothing! He wasn’t raised as a girl. He didn’t know anything about makeup or fashion or hairstyles. And how could he learn? And did he want to learn? He supposed he could ask Robin to teach him a few things. But the honest truth was that he was still too afraid… too embarrassed to talk about those things. At what point in a sissy’s life is it finally ok to talk about things like that? At what point is it finally ok to really open up and embrace it all? He really wondered about that. Unfortunately, he also knew that he still hadn’t reached that point where he would be comfortable doing it yet. Unfortunately.
He was a sissy. He was very interested in knowing. But he was still too embarrassed and scared to discuss it.