The Bet - Chapter 35 (Friday – week 5 Part 3 of 8)

The Bet
by Karen Singer

Chapter 35 (Friday – week 5 Part 3 of 8)

“Break time, Sissy,” Robin called from his cubicle entrance.
Chad turned around. “Already?” He leaned back in his chair. “I’m ready though. I need a break from this.”
“I know what you mean! But we’re almost finished.”
“Yeah, we should be able to tell Tom it’s done by lunchtime – I think.”
“I hope so. I’m ready to move onto something else for a while. This was a big one.”
“You can say that again,” Chad agreed as he closed the programs on his computer and got to his feet. As he followed Robin out into the hallway, he was more conscious than ever of the skirt he was wearing, probably because it was so full and he kept brushing his hands against the loose material. His legs also felt like they had a lot more freedom underneath.
“Okay, Sissy,” Robin said as they approached the break room, “this time, try to remember what everyone is wearing… Or at least some of them.”
“Sounds like a lot of trouble to me.”
“Just do it!”
As usual, Chad followed Robin in line for the coffee. They were both disappointed to see that there were no doughnuts though. “Oh well,” Robin said. “I wouldn’t want to undo everything I worked so hard for at the gym.”
No magical space opened up at the table for them as they approached it today, but they still had no trouble pulling up seats around it. Chad sat down, then had to stand up again to straighten his skirt before he sat down again.
“Hey Sissy, that’s another new outfit!” One of the women noted as he did it. “I like it.”
“Thanks,” Chad replied. “I kind of like it too.”
“Well, I guess you should, you bought it!” another woman added with a slight laugh. A few of the other women laughed with her.
“Your closet must be getting almost as full as mine is by now,” one of the women noted.
Chad just shrugged. “There’s still a bit of room left in it.” He didn’t tell them that the main reason there was still room in his closet was because Mel had carted all his male belongings off – to somewhere.
“Yeah?” another woman replied. “But at the rate you’re buying new stuff, it should be full pretty soon! I aught to know, my closet is stuffed to overflowing and so is the one in my guest room! Of course half the things I have don’t fit anymore. I only keep them because I figure I’ll be able to get back into them again… someday.
There was some general laughter from around the table.
“Shoot! I don’t throw anything away!” another woman added. “I’ve got stuff in my closet from back in high-school!” There was more laughter.
“Me too!” another woman added. “I just can’t seem to part with any of it!”
As the laughter from around the table continued, Chad would have thought they were pretty much joking, but he had been married! His wife – make that ex-wife – had been pretty much the same way – a ton of clothes she never wore and that he was sure she would never wear again.
“Hey Sissy!” one of the women suddenly added. “I’ve got another one for you.” Chad briefly wondered another what. “How about… Totally sissified man!”
Chad was shocked as the laughter rang around the table.
“Are you kidding?” another woman laughed. “He’s not a man. Look at him!”
To Chad’s embarrassment, there was another huge round of laughter.
“He’s not a woman either though!” someone else called out, Chad didn’t even see who. The women all seemed to be getting worked up into a laughing frenzy.
“Well then, how about… Totally sissified sissy!” Someone offered, modifying the suggestion that had been made a few moments ago.
Chad’s face burned red with embarrassment. Their comments were beginning to hurt, even though they were all true – more than they even knew! He had thought that these women were friends. Obviously he was wrong. He was seriously contemplating getting up and leaving when one of the laughing women suddenly leaned over and put her arm around him. She hugged him slightly as she laughed and said, “Don’t worry, we all still love you.”
Chad wasn’t totally sure, but he finally realized that they were all just having fun. And of course he would be the brunt of their teasing. What else could he expect? He was a sissy after all! And didn’t he inwardly love the humiliation? He just wasn’t totally sure about that just then.
On the way back to their desks, Robin asked him, “Well, did you notice what they all were wearing?”
“I tried,” Chad said, “but mostly I didn’t think about it. I was too busy being embarrassed by the things they kept saying.”
“They did come up with some funny slogans for your shirt,” Robin chuckled.
This time Chad chuckled a bit too. “Yeah, they did.”
“Maybe you should have another shirt made with one of their suggestions.”
“Uh… I’ll pass on that for now!” Robin laughed as he turned into his cubicle and sat down. Then he had to stand up again to straighten his skirt before he sat down again.
“You’ve got to stop that!” Robin complained.
“What?”
“Not fixing your skirt before you sit down.”
“Well… I don’t think of it.”
Robin rolled her eyes. “Stand up again!”
“Why?”
“Just do it!”
Chad groaned a bit, but he got to his feet.
“Now sit down.”
“You just…”
“Sit!”
Chad sat quickly.
“No, you idiot! Fix your skirt first! Now do it again.”
“But…”
“Just do it!”
Chad stood up feeling annoyed.
“Grab your skirt and pull it out.”
“Ugh!” But he did as he was told.
“Now sit down!”
Chad sat. “Okay?” he asked sarcastically.
“Now do it again.”
“What?”
“Do it again! You’re not going to learn to do it right unless you get used to it!”
Chad groaned again, but he once again got up. This time he was more flamboyant in the way he grabbed his skirt, as if he was mocking Robin’s guidance.
“This time,” Robin said, “sit more gracefully.”
Chad wanted to say something, but he bit his tongue. “He sat down slowly, again as if he was mocking her suggestions.”
“Better!” was all that Robin replied. “Try it again.”
Chad almost shouted his complaint, but he stopped himself and just stood up. This time, he quickly grabbed his skirt, but he sat down slowly again.
Robin shook her head. “It’s actually better, but you’re making a game out of it. This stuff has to be natural to you. Completely second nature. You shouldn’t even have to think about it.”
“Well, you’ve been doing it a lot longer than I have,” Chad returned.
“All the more reason why you need to be practicing it now! So do it again.”
Chad looked at her like she was crazy.
“Do… it… again!”
Women! Why couldn’t they just leave him alone! But he knew that Robin would only hound him if he didn’t make the effort. With another groan, he got to his feet. He paused, then grabbed his skirt, then sat down – trying to be at least somewhat graceful. But Robin’s only comment was, “Again!” Four more times she made him do it. Then she finally left with one parting comment. “Now keep doing it that way.”
It was childish, but Chad actually stuck his tongue out at her as soon as she was gone.

Mel reread the paragraph for the third time. It was simple basic stuff, but it still had to be checked. Unfortunately, her mind kept wandering, so consequently, she didn’t remember anything about what she had been reading. The problem, of course, was Chad – Sissy. She didn’t want him to go to the poker game, but something deep inside of her was still telling her to do it. Why? It made no sense! It was all wrong!
She thought again about what Andrea had said, if she couldn’t get it out of her head, then maybe she should send him. Maybe her subconscious was trying to tell her something. Maybe something important. And she’d never know what it was if she didn’t send him.
With a sigh of frustration, she reached for her phone.

Chad heard his cell phone ringing inside his purse – inside his desk drawer. As quickly as he could he opened the drawer and pulled his phone out of his purse. Shit! It was Mel. Quickly getting to his feet, he hurried up the hall, even as he opened the phone and answered the call. “Hello,” he said, careful to use his high-pitched voice.
“Sissy!” Mel’s angry voice replied. “What took you so long again?”
“I can’t get my phone out of my purse that fast. I keep it closed up in my desk drawer.”
“Then keep your phone out of your drawer, on top your desk! And you sound like you’re hurrying somewhere again!”
Chad stopped where he was, hoping nobody could hear him as he spoke. “How did you know?” he asked.
“Your breathing is practically panting and I can hear your heels on the floor!”
“Oh.” He hadn’t thought about the sound his heels might be making.
“You’re still trying to hide again!” Mel proclaimed.
“But I can’t let anyone hear me talking like this!” Chad whined in his sissy voice.
“I don’t care! You can! And you will! Next time, it’s another demerit!”
But all Chad could think about was that he couldn’t. There was absolutely no way!
“Sissy!” Mel’s voice brought him back to reality. “I need you to do something – something you’re probably going to love.”
Love? “What is it, Mistress?”
“Remember that poker game you told me about that your friend is throwing? I want you to get in it.” The minute Mel made the request, she realized she was leaving out something important. “Not just you, but me too!”
Chad was shocked. Something he’d love? Maybe under different circumstances! “But Mistress…” He searched for a way out. “That’s kind of a ‘guys only’ thing. No women.”
“I know, and I don’t care! Just do whatever you have to, to get us in that game! Tell them we’ll even bring some beer – lots of beer!”
Why was she being so insistent? She had to have some kind of humiliating motive behind it – strip poker maybe? But the guys would never go for it… well, if she was there, maybe they would. She did have a gorgeous body. Maybe he hadn’t seen it with his eyes, but he had certainly felt every inch of it. He didn’t even want to imagine himself at the game, talking in his silly voice… and what would she make him wear, one of his sissy dresses? No way! “But Mistress, they’ll never go for it!”
“See to it that they do. Cause if you don’t…” Mel tried to quickly think of some appropriate punishment. An odd picture came to her mind. “If you don’t, then the day after, I’ll be driving you to work personally and leaving you there so that you’ll have no way home. But instead of leaving you there in one of your pretty sissy dresses, you’ll be spending the day in a pink ballet outfit complete with tutu! Now wouldn’t your friend Robin just love to see that?”
Chad was horrified. “You wouldn’t! You couldn’t!”
“Yes I would!” Mel returned. “I told you before how many times I was sorry for not taking you to work in your sissy dress the last time!”
She had told him. More than once! She was just looking for another excuse to really do it. “I… I… I’ll try,” he stammered into his phone.
“Don’t just try… do it! I’ll expect to hear from you later that you’ve succeeded, or after you get your nails done tonight, you’ll be trying on ballet slippers!” Mel hung up her phone and smiled. She hoped she had sounded sufficiently mean. She thought she did. At least she had convinced him to try to get them into the game. She wasn’t really sure if he could manage it or not, but she had to properly motivate him to try hard enough. And if she didn’t… we’ll she wouldn’t really do it, but the thought of him in a pink leotard with white tights, pink ballet slippers, and a white tutu – at work, was enough to make her feel very amused. And strangely, the more she thought about it, the more she realized that the idea was making her wet in a very pleasant place.