(Continued thanks to Rotorhead450 for bugging me to hurry up and finish my stories and publish!!)
Jill was smirking at Bobby as she ordered. It was a lunch-date of sorts, at the restaurant on the 100th floor of the ICC building in Hong Kong. The Carton Hotel had a wicked lunch steak, and you can imagine the price. Just the bottled water cost more than a meal down on street level.
"We have to change this," Bobby moaned. "It doesn't make any sense."
"Stop complaining," Jill admonished him. Bobby was arguing that by losing the sales battle that month, he was already behind financially - so paying for a ridiculously expensive lunch was a double hit.
"Penalties shouldn't cost money if you already lost money. Not this much."
"You agreed," Jill shrugged.
"Next month, we do something that doesn't cost money."
"Okay, fine. But today...waiter!"
Bobby was a Chinese-speaking white-boy Brit, a rarity in Asia. He was great at selling and almost always led the way - but he was all over the place and disorganized. Jill was an English-speaking Chinese girl, dime-a-dozen in Hong Kong, even with her made-for-the-bedroom looks. Jill's advantage was her judgment; she had a handle on exactly when her deals would come off, and a better sense of Bobby's deals than Bobby did. When he was bragging about being number one for each of the first six months of the year, Jill smiled and put up a challenge. She knew what was going to drop in the following two months. When she won in July, it was a simple ramen lunch. When she taunted him for August, he bit hard not knowing Jill's biggest deal of the year was set to be signed on Aug 31, purposely timed for her client's IPO launch announcement. So they were up in the clouds eating melt-in-your-mouth steak on Bobby's purse.
"Okay, no September challenge, we call it quits," Jill said, knowing she was dry that month.
"No way, I need to catch up."
"Don't need to! Cut your losses," Jill said, knowing Bobby was hardly the type.
"No way. If you lose September, on October first, you go to the office wearing only one of my shirts. Nothing else."
"Nothing under?"
"Nothing."
"Nothing over?"
"Nothing."
"No shoes?"
"You can wear shoes," Bobby laughed.
"Stockings?"
"Thigh-high only. Nothing that covers your cunt."
Jill shuddered at the word. She didn't like swearing of any kind at work, and especially that. But she had to keep her cool. She had no deals to play with, it would need to be a clever bluff to get him to drop the monthly challenge.
"October first, right?" she said, thinking of a technical loophole.
"The second, October the second!" Bobby clicked. The first was China Day, a public holiday. "Are you trying to get out of this?"
"Of course not," Jill smiled as confidently as she could. "But if I have go to work with no underwear and just wearing your shirt, the same deal applies to you."
Bobby smiled. Clearly that wouldn't happen. A shirt that size on Jill would fall down below her ass and pussy. On Bobby, he would be tackle-out. He shook his head and Jill didn't argue.
"Okay, if I'm wearing a man's shirt with no underwear, you can wear a woman's dress without any either."
Bobby shrugged, "Okay."
"Not a Kaftan, if that's what you're thinking. A proper dress."
"I'll wear a kilt."
"No way. Something short, where the slightest breeze shows your penis," Jill challenged. She had to get him to a point of disagreement on the deal. She had to get Bobby to refuse the bet.
"Okay, but it has to be so either of us standing up straight, right in front of a policeman, wouldn't get arrested."
"You'd wear a dress to the office?" Jill frowned.
"I'd figure out a way. Better than the money I'm spending here."
"Have you no shame? Think of what people will say about you."
Jill sighed. He was a salesman, of course he had no shame. If he did he wouldn't be able to get past all the rejections to find a deal that can be closed. Perhaps a miracle deal would come in and save her.
It didn't. Jill lost the bet.
They met in a shopping mall near the office. Jill had to be sure her husband knew nothing about it. They'd only been married a year, and he was possessive of her body - as she expected her man should be. People walked through the mall to work, though none of the shops were open. Jill used the wheelchair toilet to change.
"There's no mirror in there," Jill said from a quiet hallway. "Can you tell?"
"Tell what?" Bobby asked.
"I've got nothing under?"
"No," Bobby lied.
"Why did you have to get one so short?" Jill complained. "You can see the tops of the stockings."
"You look good," Bobby said truthfully. Her stockings were black with lace grips on her thigh, the shirt was square rather than tailed, short and wickedly thin. The color of Jill's skin and small patch of pubic hair showed through. A Brazilian cut? Bobby tried to hide his erection. "Don't worry, you could stand straight in front of a policeman and not get arrested."
"What if I lift my arms?"
Booby looked. Shit. Jill had a shaved slit with the tiniest patch of hair. The gap between her thighs was gorgeous.
"Can't tell," he lied, "But if you're worried, just don't lift your arms."
"You are so going to pay when I win next," Jill growled.
Dressed as she was, there was only one way to approach the day - normally. Jill knew that if she showed any hint of embarrassment, it would only accentuate her situation. If she acted normally, then it was simply a piece of fashion. She hoped.
For the mostly male staff population, they discovered what previously they could only imagine. Depending on the light, they could see Jill's ass through the shirt. Regardless of the light, they could see she had small areola. And for the lucky few who were around during a careless moment, they could see Jill had a hairless slit.
Bobby took her to lunch at Shake Shack to make her feel better. He sat next to her, rather than opposite. It gave him more view.
"See, even when I win I'm buying you lunch," he smiled.
"So you should. This shirt is ridiculous. It's too thin, and too short. Can see everything through this."
