The Bet - Chapter 41 (Thursday – week 6 Part 4 of 8)

The Bet
by Karen Singer

Chapter 41 (Thursday – week 6 Part 4 of 8)

“Sissy…” Robin called over the wall. “What are you doing?”
Chad almost yelled back ‘nothing!’ but he stopped himself just in time. It wouldn’t be good to be yelling that – just in case anyone else might hear it. “Working!” he yelled back. “Why?”
“Girly voice, Sissy. You’ve got to use your girly voice!”
“It’s hard to yell that way.”
“It doesn’t matter! You need to get used to it in all situations.”
“So what do you want?” Chad yelled back – in his high pitched voice. What a pain!
“Come look at this.”
Tired of yelling over the wall, Chad got up from his seat to see what she wanted. He really didn’t have anything better to do anyway.
“What is it?” he asked as he walked into her cubicle.
“Look at this,” Robin said. “This store just posted the latest dresses they got in.”
The major part of Chad really was interested, but there was still something in him that made him hold back – male pride perhaps. “And why should I be interested?”
“Geez! You really have a long way to go,” Robin replied – something she had said many times to him before. “I just thought that you’d enjoy looking at them. Besides, maybe you’ll find something good for your date with Derek this weekend.”
His date with Derek! The one thing he didn’t want to be reminded of! “I don’t think I need anything special for that.”
“So? It never hurts to look does it?”
Chad didn’t want to admit that he had been filling some time at his own desk looking at shoes. “I guess not,” he replied.
She looked at him. “You know, maybe if you tried softening your voice a bit, then it might sound better. I mean, the higher pitch is one thing, but you’ve got to start working on making it sound better now.”
“Softer?” Chad asked, dropping his voice to almost a whisper.
“Not that way! Just not as harsh! Try it!”
Chad wasn’t really sure that it was what Mel wanted, but he tried. “Is this better?” he asked, trying to take some of the edge out of his ‘girly’ voice.
Robin just looked at him. “I think so… Maybe… It’s a step in the right direction anyway. Why don’t you go get your chair and we’ll look at these dresses together. See if there’s anything you like. Then you can practice talking a bit more… femininely.”
Chad didn’t know what he should really do, but knowing Robin, he wasn’t going to have an easy time getting out of it. So he left momentarily and came back pushing his chair ahead of him. Together they sat and discussed each and every dress, one at a time. Robin constantly tried to figure out little ways to make his voice sound better. By the time they reached the last dress – an hour later, he was sounding a bit better, but only a bit.

Mel sat on the toilet and glanced down to check the pad protecting her panties from the ravages of her period. It was obviously soaked. Time to change it – again! Ugh! She hated her periods… mostly. Unfortunately, they were all part of being a woman. Why couldn’t men have at least a similar problem to deal with every month?
She briefly toyed with the idea of making Sissy go through some kind of monthly period, but she quickly abandoned the idea. The total lack of control she had over her bloody mess – wasn’t that pretty much like the total lack of control she was trying to create in him – permanently? And pads would never be enough for what Sissy was experiencing. Sometimes, three heavy diapers weren’t enough. No, what Sissy was feeling was probably much worse.
Of course, there were the cramps and bloating issues to deal with. But the cramps were probably nothing compared to the pain she inflicted on him – and not just once a month. And the bloating? Well, she was forcing him to drink a fairly extreme amount of liquids all the time. She had no doubt that despite all the weight he still seemed to be losing, his body was probably overly waterlogged to boot.
But at least her period was slowing down now. It wouldn’t be long till it was over – at least for the next month. She looked forward to it ending. Of course there were also the fringe benefits of no period to think about too. Like a little sexual stimulation from Sissy’s talented tongue. That thought made her smile! And from somewhere in the back of her brain, she remembered a phrase that Cassie had said to her last month – “If you’re not making a mess, then you’re not having sex!” That stopped her in her tracks. Could she really do that with him? Did she dare? Even now, when she still had another day or so to go? She almost giggled. There was nothing there that would really hurt him. In fact, since she blindfolded him every time, he might not ever know! Did she dare? The thought did kind of turn her on. This time, she did giggle out loud.

“Break time!” Robin called from the entrance to Chad’s cubicle.
Chad turned in his seat. “Good! I could use a break,” he replied in his usual male voice.
“From what?”
“From doing nothing!”
Robin giggled. “Hey! Say that again, but try to make it sound better.”
“Can’t we just go to break?”
“Come on! I’m trying to help you! The least you could do is to try to cooperate a little!”
Ugh! “What did you want me to say again?”
“Anything!” Robin shook her head. “Never mind, let’s just go!”
Chad mentally cheered. Had he actually won that round? He got up and followed Robin out into the hallway.
They were early enough that the break room wasn’t crowded at all when they got there. Chad and Robin each poured their coffee and were the first to sit down at the women’s table. Chad sipped his drink and watched as some of the usual women entered the room. It was amazing how many of these women he knew now… although most of them he associated with how much they liked to tease him. Still, he guessed that each of them was now a friend… of sorts. He was still embarrassed about being “one of them.” Even if he wasn’t really. But he was sitting there in a skirt and blouse – just like… some of them – because the majority of them wore nice pants to work.
“Hi Robin. Hi Sissy,” one of the women greeted them as she walked up with her coffee and sat down. She was quickly joined by two more, then three more, then… more. Within minutes, the table was buzzing with different conversations. Chad tried his best to stay out of most of it, but there were times when some of them would ask for his opinion on something or just made a dumb comment about something. And the odd thing that Chad noticed, was that for once, they all seemed to be friendly. None of them were teasing him… yet.
And then his eye just happened to catch Derek walking into the break room. He saw Derek glance at the table full of women, and then at him. Derek stopped dead and stared at him for a second, then turned around and walked out again. Chad suddenly felt bad. He had no doubt that Derek had left just to avoid him.
“Hey, wasn’t that Derek?” one of the women asked.
“Yeah, he just turned and left,” another woman relied. “I wonder why he did that?”
Robin looked at Chad. “Why don’t you go after him?”
“Why would I want to do that?” Actually Chad was glad that Derek had left. He didn’t want to be seen with him any more than necessary either. The rumors and teasing were already too much.
“Well,” another woman replied. “Aren’t you supposed to be his girlfriend?”
“I’m not his girlfriend!” Chad replied. “We’re just stuck having to go out on a date together… and I don’t think either of us is happy about it.”
“You’re not his girlfriend?” one of the women noted. “But you’re his friend, and right now, you’re certainly the girl in the relationship. Am I wrong?”
Chad looked for a way out of that argument and quickly realized that anything he said would probably turn out bad. “Well, I guess that’s sort of true. But I’m not really his girlfriend.”
“Sure you are Honey. Now why don’t you start acting like a girl and go after him? You don’t want him to think you’re not interested, do you?”
Go after him? They wanted him to go after him? “He shook his head, then smiled broadly. “I’m playing hard to get.” He replied. “Let him come to me.” His answer brought a round of laughter from most of the table.
“Hey Sissy,” another of the women said. “It sounds like your voice is starting to get a little better.”
“It still has a long way to go though!” another woman added.
“Yeah, but I think it does sound better,” the first woman replied.
“We’ve been working on it a bit,” Robin explained. “The problem is though, that he doesn’t want to keep trying!”
“It’s difficult!” Chad complained. “Not to mention embarrassing.”
“Honey, you think wearing a dress and sounding like a man isn’t embarrassing enough?” one of the women asked. “And who ever said that being a woman was easy?” There was some general laughter and agreement around the table.
“You should try it from my perspective,” Chad muttered.
“Well if you’re trying to live your life from our perspective, then try listening to your heart a bit more. Try acting like a woman more. That man is definitely fine! So go get him! Let him know that you like him.”
Chad quickly realized that this was starting to go exactly where he didn’t want to go. “But I’m not really his girlfriend. We’re just friends.”
“Don’t matter Honey. Relationships are important to a woman! Any relationship. If I were you, I’d get my panty covered fanny out there and make sure you and he are still good!”
Panty covered fanny? If she only knew what he was really wearing on his fanny! “But we are good!”
“Didn’t look like it to me! Like I said, relationships are important. If you want to be the girl, then you go make sure that he knows things are still okay.”
“She’s right, you know,” Robin added. “You should go and make sure that he’s not mad at you.”
“I feel like you’re all trying to get rid of me,” Chad complained.
“Honey, we’re trying to help you! Now get!”
Chad sighed, this wasn’t a good idea. He got up from his chair though to do as they suggested. “See you all later.”
“Go get him, girl!” one of the women called after him.
Chad wasn’t sure but he thought he heard more laughter behind him. He was supposed to be the girl in the relationship? Well, he supposed that that part was true. He just wasn’t used to having to act like a girl… not that he’d really have the first clue as to how.
As he left the break room, he wondered where Derek had gone. Probably back to his desk upstairs. He wasn’t about to go all the way up there… period! Chad half heartedly searched the hallways for Derek – on his way straight back to his own desk. He really had no intention of talking to Derek. He knew perfectly well how Derek felt about the situation because it was exactly how he felt. But as he passed the doors across from the elevator, he noticed someone standing just outside leaning up against the wall. Even from behind, he could tell that it was Derek. Should he go out there, or not? Was it really a girl thing to want to patch things up? Not that there was anything wrong between them to begin with. But he could tell that Derek wasn’t exactly happy. Before he knew what he was doing, he was opening the door and walking outside.
“Hey, Derek,” He said… cautiously, in his male voice.
Derek looked up at him in annoyance. “You want something?”
“I just want to make sure that you’re not totally mad at me,” Chad replied. “I’m not too thrilled about this date situation either.”
“Yeah, well trust me, it’s even more embarrassing from my point of view,” he replied. “I mean, look at you, you’re obviously okay with going out with anybody at all!”
“Not really.”
“Well, at least you don’t care what gender they are then. You are the one wearing the skirt here.”
Unfortunately, Chad couldn’t deny that part at all. From Derek’s point of view, he was probably completely right… even if he was really wrong. Chad was suddenly more aware of the skirt around his legs and the way that he was dressed than ever. “I know it looks that way, but… things aren’t always what they seem. I’m not interested in going out with guys.”
Derek shook his head. “It doesn’t matter. With the way you’re dressed, nobody would ever think twice about who you’re with!”
Chad couldn’t deny that statement either. “I just wanted to make sure you’re not avoiding me because of this stupid date we’re stuck with.”
“I was,” Derek replied. “You have no idea the amount of teasing that Ray has been heaping on me over this. You don’t have to put up with that problem at all!”
“I have every woman in the company teasing me and riding my ass instead. Not just one person, a lot of people.”
Derek looked at him. “You’re kidding? They’re teasing you about it?”
“Constantly!”
Derek smiled. “I’m glad it’s not just me then.”
“I just don’t want you to have to walk out of the room if I happen to be there,” Chad said.
Derek nodded. “Thanks, but for now, it may be better if I do.”
Chad nodded disappointedly. “I understand. Is there anything I can do to help?”
“Other than not be anywhere I’m going? I don’t think so.”
“That’s going to be hard. I don’t want you to not be able to use the break room. We were doing fine till this stupid date thing popped up – although the women were all teasing me even before that about me and you.”
“You’re kidding!”
“No, but that’s just women. They have to have something like that to talk about all the time. Relationships are more important to women than to men.”
“I guess you should know… now.”
Chad was about to deny that, but wasn’t that the reason he was taking to Derek now? “I’m… learning,” he finally replied. “I guess I still have a lot to learn about women… or even about being one.”
“Well, good luck with that. I can’t help you there.”
Chad smiled. “I guess not.”
“You know though…”
“Yeah,”
“You could try being a bit more… consistent.”
“Consistent?”
“Yeah. I mean, look… You’re out here wearing a skirt and heels, and you’re talking to me like a man. At least, I mean, you’re talking in your old male voice. By the way, weren’t you supposed to be trying to stop that? It makes me feel funny to be talking to you when you look like a woman, but then you open your mouth and I hear the old you instead!”
Chad actually blushed. “Sorry,” he replied, this time in his new, more feminine, girly voice. “I thought it would make you feel… more at ease.”
“Yeah, I get it. But it just seems weird. You know?”
“Yeah, I guess so.”
“And then there’s the way you dress.”
Chad was surprised. He quickly looked down at what he was wearing. “What’s wrong with it, other than the fact that it’s totally feminine?”
Derek shook his head. “It’s not that! You look fine – now! I guess anyway, for what you’re trying to do. It’s… well… the other night. What was with the crazy way you were dressed then? It was stupid! What were you trying to do?” He shook his head. “I sure hope you’re not going to dress like that for our date Sunday.”
The problem was that Chad couldn’t really guarantee that at all. Knowing Mel, she might come up with anything! “Sorry, no guarantees,” he replied.
Derek rolled his eyes. “Think about it! For my sake! Please! Don’t make things any worse than they already are.”
Chad just nodded. “I’ll… think about it.” Unfortunately, it was a matter he knew he would have no say in whatsoever. “So… Are we good then? I mean, still friends?”
Derek just looked at him, but finally nodded. “Yeah, still friends. I just wish you hadn’t… changed.”
Chad hung his head sheepishly. “Sorry,” he replied. “It kind of caught me by surprise too.”
Derek just shook his head. “I don’t think I’ll ever understand.”
“It’s okay. I don’t expect you to. Just don’t hit me when we’re together,” he joked.
This time Derek smiled. “If you can’t guarantee what you’ll be wearing for that date, then I’m not going to guarantee that!”
Robin had almost missed seeing Sissy and Derek talking together outside. She desperately wished she could eavesdrop on that conversation, but that was out of the question. So she waited inside across the hallway for him. Finally she saw the two of them shaking hands together and together they turned and walked back inside. It was the handshake that bothered her though – it was all wrong! She shook her head at Chad the minute they got through the door. “I guess you two are still friends?” she asked.
“Yeah, we’re good,” Sissy replied. “There was never any doubt.” He looked up at Derek for confirmation. Derek’s non-spoken shrug left a bit of doubt though.
Robin looked back to Sissy and shook her head again at him. “You really have an awful lot to learn!”
“What now?” Sissy asked. “I thought I was doing pretty well.”
“Women don’t shake hands like you two just did. In fact, what you probably should have done was to give him a small hug instead. But even shaking hands, you shouldn’t do it like a man!”
Derek looked down at Sissy. “I see what you mean about them being on your case all the time. And just for the record. I’m glad you didn’t try to hug me, because then I might have had to hit you for it!”
Chad would have laughed his comment off, but just then the stupid suppository that Cindy had put up inside of him at the gym earlier decided to do its thing. Without warning, he suddenly felt his insides rushing out into his diaper.
“Hey,” Derek exclaimed, seeing the look on Sissy’s face, “I didn’t really mean it… it was just a joke… sort of.”
“It’s okay,” Sissy replied, carefully trying to not show what was really happening. “It just kind of caught me by surprise.” He just wasn’t going to mention what that ‘it’ really was.
After Derek left, Robin said, “You know, you did go white as a sheet there for a moment. But then, I guess I might too if someone that big threatened to hit me.”
There was no way that Chad could tell her anything about what had really happened. “Like I said, it just kind of caught me by surprise.”