The Bet - Chapter 26 (Wednesday – week 4 Part 2 of 6)

The Bet
by Karen Singer

Chapter 26 (Wednesday – week 4 Part 2 of 6)

“Hi Chad,” Robin’s voice called breathlessly as she hurried past his cubicle. She was running a bit late… not that anyone would really care. But before she got fully into her own cubicle, she stopped short. Had she noticed his bare legs again as she walked past? She had the distinct impression that she did. Of course, she had been hurrying and had just barely glanced. With her arms still heavily loaded, she took a few steps backwards till she could just see into his cubicle again, and this time she quietly took a closer look. “Sissy! You’re all dressed up again. And that’s the same outfit you wore last week.”
Chad turned around at the sound of her voice. He was startled because he hadn’t heard her come back. “Hi Robin,” he replied as he felt himself blushing. He looked briefly down at himself. “Is there something wrong with this outfit?” he asked, still unsure of himself.
She stared at him, totally surprised at his question. “You’re a guy, who wear’s nothing but women’s clothes every day, and you’re asking if there’s something wrong?” She shook her head. “For what you are, it’s great!” She shook her head one more time and walked back to her own cubicle so she could unload all the things she had been carrying.
Chad stared after her. For what he was? What did she mean by that? He got up and followed her around to her own cubicle. She had set a large pile of things down on her desk and was just opening her big bag as he got there. “What do you mean, for what I am?” he asked.
She pulled her big mirror out of her bag to check her face, but before she could look into it, she stared at him instead, totally annoyed by his question. “What do I mean? Well look at you, for God’s sake! Obviously, you’re one of those stupid transvestite people. Only one who seems to carry things further than most that I’ve read about.” She looked at him more carefully. “Or are you really… what do they call themselves… transgendered or something? One of those men who are actually trying to change what sex they are. Because that’s what you seem to be!”
Now it was Chad’s turn to be surprised. “Me? Transgendered? Is that what you think?”
“Well what else am I supposed to think?” she asked testily. “It’s not exactly normal for a guy to suddenly turn up in women’s clothes and then that’s all he wears from then on.”
Chad shook his head. He supposed what she thought only made sense. No doubt it was probably the impression he gave everyone. But because of the bet, he had no choice in the matter. “That’s not exactly it,” he said softly.
“So what is it?” she asked, still agitated.
He shook his head again. “It’s complicated. I don’t want to talk about it.”
She almost threw the mirror in her hand at him. “Get out of here!”
Chad quickly retreated back to his own cubicle. What was eating her today? Ok, maybe she had a right to be angry at him, but he still couldn’t explain anything to her. The last thing he wanted anyone else to know was about the diapers he had on under everything else… or even about the bet itself! He supposed he’d just have to keep giving everybody the impression that Robin already had. He smiled to himself. It was somewhat true. He did like wearing women’s clothes… deep down. It was totally humiliating… but he did like it.
He turned and faced his computer. The email this morning had still not contained anything about the project they had been working on. So what was he supposed to do with himself again all day? He leaned back and laced his hands behind his head… and noticed his skirt, and his pantyhose covered legs. Damn! He was actually doing it again! He was actually wearing a skirt – at work! He still found it hard to believe.
He stood up and looked down at his clothes. If he leaned over far enough, he could see past his breasts and the hem of his skirt all the way down to the tips of his shoes. He swung his hips back and forth a few times to watch the skirt swish around him. It was fascinating to see how it moved… not to mention how odd it felt against his legs.
“What are you doing?”
Chad jumped at seeing Robin leaning around the edge of his cubicle. He immediately felt his face blushing a deep red. What could he tell her? “I’m just trying to get a feel for how this skirt moves,” he replied. Well, it was the truth… mostly.
She nodded. “Yeah, I can see that.” She came all the way into his cubicle. “By the way. I’m sorry if I sounded angry earlier, the baby had kind of a rough night last night.”
Chad nodded. “Didn’t get much sleep?”
“Not really.”
“Diaper rash bothering him?” Chad asked… hopefully.
Robin looked at him strangely. “Diaper rash! Not on your life. That’s easy to fix. No, sometimes he still gets colicky and he can’t sleep. He cries for hours.”
“Oh,” Chad replied. “Sorry to hear that.” He really wanted to ask her about how she fixed her baby’s diaper rash, but he chickened out. Instead, he looked back down at his skirt, then back up at her. “So is there really anything wrong with wearing this again?”
She shook her head. “Of course not. It’s just the same thing you wore last week – the last and only other time you wore a skirt to work. I just would have figured you’d wear something different this time. That’s all.”
“Oh,” he replied as he pulled on his top, stretching it back down into place again after the swishing back and forth he had just done. “The truth is, I didn’t know what else to wear today.”
“And you didn’t want to wear slacks like you usually do?”
“Um,” how could he put it without giving anything else away… “not today.”
“Well, just to be different, you might try getting a few more skirts and dresses… if you’re going to be wearing them, that is.”
He shrugged his shoulders. “Actually, I’ve got quite a few.”
“So why did you wear the same thing again?”
He shrugged his shoulders. “I’ve got several skirts and a bunch of tops, but I don’t know how to mix and match them together.” He looked down at what he was wearing again. “I know these go together so there’s no problem.”
Robin looked at him trying to figure out if he was serious or not. He certainly seemed serious. When you bought your other clothes, didn’t you buy things that you had some idea what you’d be wearing with them?”
Chad shook his head. “Not really.” He couldn’t tell her that it was Mel who had picked out most of the things he had now… except for the few things he had had from before.
Robin shook her head. “You might want to think about that the next time you’re out shopping.”
“Yeah, I’ll do that,” he agreed sheepishly. It was a thought, knowing in advance what would go with what. Even when Mel was picking them out.
He sat down again in his chair. But instead of leaving, Robin moved all the way into his cubicle and leaned against his desk. “So what other clothes do you have… women’s clothes that is?”
Chad raised his eyebrows at her question. The last thing he expected to be discussing with her was the contents of his closet. “Well,” he began, trying to find a place to start.
“Do you have a lot?” she asked, interrupting him before he could get started.
He shrugged. In the last month, Mel had made him buy a lot more than he had ever planned on. “I guess,” he replied.
“Wait a minute then,” Robin said just before she hurried out. She came back a moment later, pushing her chair ahead of her. “I may as well sit down while we talk. This should be interesting.”
Chad was a bit surprised by her forwardness, but he shrugged it off and began describing the contents of his closet – purposely leaving out his maid’s dresses and anything else he didn’t want her to know about. With every item he tried to describe, Robin grilled him for more information as to style and color and in some cases, who the designer was. But she quickly learned that Chad knew nothing at all about the clothes he had. He couldn’t even describe the colors or the prints properly. “Geez, for a sissy, you really don’t know anything,” she declared at one point, thoroughly disgusted and frustrated with his lack of knowledge.
“For a sissy?”
“Well, yeah. Don’t most guys like you know a lot about this stuff? I thought they did anyway.”
“Obviously not,” Chad replied. Despite her comment, and despite the awkward topic for him, he suddenly felt like a bit more of a failure.
“I mean… geez! A four-year-old girl knows more about her clothes than you do. It’s like talking to a complete baby!”
Chad was completely taken by surprise by her statement. Especially the part where she practically called him a baby. Worse, he knew she was exactly right… more right than she even realized. “Uh,” he said, trying to find some way to reply.
“Look,” Robin said. “I’ve got an idea. We’ve got nothing better to do anyway.” She disappeared for a few moments, then came back again with a handful of magazines. She set them on his desk in front of them. “Let’s go through these together. I’ll point to some pictures, and then you tell me if you have anything even remotely similar. Ok?”
Her idea startled Chad a bit. It also embarrassed him some. But he agreed to go along with her suggestion – mostly because he was truly interested… deep down inside somewhere. Besides, he had a feeling she wasn’t exactly giving him a choice in the matter.
Robin flipped through the pages of the magazines, stopping often to point at pictures and comment about the clothes the model was wearing. Despite having nothing to really say about the pictures she was pointing at, Chad found this far more interesting than just looking at the magazines on his own. Then, something about a skirt in one of the pictures caught his eye. “Wait a minute,” Chad said, leaning forward to peer at the picture more intently. He pointed to the skirt the model was wearing. “I’ve got one that’s almost just like that. But mine doesn’t have a belt like that one.”
Robin peered closer at the skirt he had pointed to… happy that he had actually been looking for clothes that were similar to what he owned. “Yeah,” she said with a lot of interest. “That’s a nice one. Nice color too. It looks like a basic A-line skirt. You could probably wear that with almost anything.”
Chad felt glad that he had finally found a picture that was similar to something that he had. As Robin kept turning the pages, he had to stretch his imagination a bit to relate the clothes that he owned to anything in the pictures. But the process was really made a lot more difficult because he didn’t remember much about most of his newer clothes since the only time he had ever worn them was in the dressing room at the store. Yet he tried his best to find matches for Robin to see.
It was a while later, that he realized how interested and comfortable discussing the clothes and the fashions he had become with Robin. Surprisingly comfortable. And dare he say it, he was really enjoying himself. Was he finally getting to the point where he could enjoy talking about feminine things… or possibly just engaging in normal “girl-talk” without being embarrassed by it? He seriously doubted it. In fact, he knew he wasn’t. It was only the situation right there with Robin that made it seem comfortable for him.
Robin closed the magazine they were looking at and leaned back. “I need some coffee!” she declared. “Let’s go get some.”
Chad checked his watch. It was just getting close to everyone’s break time. “No thanks. Everybody will be heading to break right now.”
Robin looked at him and rolled her eyes. “Oh come on! Everybody’s seen you in that dress before anyway.”
Chad shook his head. “No thanks.”
Robin stood up, then stopped. “You’re being stubborn and stupid again,” she declared. She reached out and grabbed his arm and pulled. “Come on! You’re going whether you like it or not!”
“Robin… No!” he replied, resisting her efforts to pull him out of his chair.
“Look, if you don’t go willingly with me, then I’ll get everybody to come back here and drag you down there again!”
“You wouldn’t!”
“I did it before, didn’t I?”
Chad looked up at her in horror. “You would, wouldn’t you!”
“You better believe it!”
He shook his head. There was no winning with women… anytime. “I’d rather not,” he said… trying to get out of it one more time.
“Get up and walk!” she ordered as she pulled again on his arm.
“Ugh!” he grunted in total frustration as he got out of his chair. He was heading for yet more humiliation that he didn’t really need just then – or anytime for that matter. As he walked beside Robin toward the break room, he was more aware than ever of his exposed legs and the looseness of his skirt as it lightly brushed his legs. Just the fact that he was again wearing a skirt at work embarrassed him and made him feel extremely self-conscious. Despite the fact that his skirt was actually comfortable to wear, he felt very uncomfortable in it. He wasn’t used to showing his legs in public like that – especially at work… around all too many people that he knew. He felt silly and embarrassed doing it. He realized that even though the pants he wore now were all women’s pants, they brought him a lot of comfort just in the fact that his legs weren’t so exposed.
He was overly conscious of his skirt and his legs all the way to the break room. But halfway there, he was also aware that the humiliation from what he was wearing was again fueling his unrelieved sexual needs. Damn! And the closer he got to the break room and the people he imagined that would be there, the worse it got. He hated it! Yet he loved it! And his nervousness grew along with his sexual excitement as the break-room came into sight.
Nervously, he entered right alongside Robin, as if she could somehow protect him from some of the humiliation he knew he was in for. There were a few people already in the break room, pouring coffee or sitting together at the tables. Chad followed Robin to the coffee pot, then to Robin’s delight, further down where they each grabbed one of the donuts that were still left. Chad did his best to not look around the room while he got his refreshments… he didn’t want to see who might be staring at him. But as soon as he had a donut in his hand, he had no choice but to turn and look around the room for a place to sit. He wanted badly to go back to his desk, but instead he meekly followed Robin over to one of the tables.
As he and Robin started in on their donuts, they were joined by more and more women, who all seemed to make a point of saying “Hi Sissy,” a lot louder than he liked. Of course, he knew they were all just trying to be friendly – friendly that is, if being a friend meant humiliating him.
As they talked, Chad noticed other people in the break room out of the corner of his eye. He glanced quickly at them, then just as quickly glanced away. They were his friends too… or they used to be. They were the men who would no longer talk to him… not that he wanted them too. At least they all respected him enough to stay away from him – totally. He really couldn’t blame them. If he were in their shoes, he wouldn’t go anywhere near someone like him at all either.
He couldn’t help glancing quickly at some of the men in the room again. He inadvertently locked eyes with a man over by the coffee pot – a friend he had known fairly well… before. He saw his former friend scowl at him and purposely turn away, walking purposely out of the room. Chad couldn’t blame him a bit. Seeing his reaction only made him feel that much worse about his situation than he already did. But unfortunately, there was nothing he could do about it.
The conversation around him brought him back to where he was. It took him a moment to realize that Robin was telling everybody about what they had been doing all morning. Oh great!
“Girl, you need some accessories!” one of the women declared. “It ain’t about what top you wear with what skirt… it’s all about what you dress it all up with!” As she said it, she pulled on her long necklace with one hand and held her other hand out, proudly showing off the rings covering each of her fingers. The women all laughed.
“I don’t have many… accessories – yet,” Chad replied.
The woman laughed. “You come shopping with me sometime, Honey. I’ll find you lots of interesting things you can wear.”
Chad rolled his eyes a bit. “I have no doubt!” Fortunately, everyone around him, including the woman laughed heartily.
“By the way,” the woman continued, “how come you don’t wear any earrings? I’m surprised by that, ‘cause even guys are wearing them these days.”
Chad was totally surprised by the question. “I guess because I don’t have any,” he replied.
“Why? You got something against them?”
“No, not at all. I just don’t have any… yet.”
The woman smiled and nodded her head. “Yet! You got to at least have the basics, girl. Now it’s none of my business, but I’d think that someone like you would at least own a pair of earrings.”
“Um… maybe soon,” Chad replied. Actually, he had mixed feeling about earrings. Yes the thought of them excited him greatly, but at the same time, earrings would be like another nail in his coffin. And he wasn’t sure he really needed that. But should he get some? It was certainly a question worth considering… or dreaming about, which would be safer.
As they talked, Chad still felt very awkward around the women, especially trying to talk about the things they were discussing – which was mostly clothes… and him! Girl-talk. It was so inviting. Yet he still couldn’t bring himself to get fully into it or even allow himself to enjoy it. He had to wonder yet again, at what point in a sissy’s life is it ok to just relax and let go… and truly let yourself enjoy something like girl-talk. At what point? He wanted to… he just wasn’t there yet.