Hong Kong Story 01

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Newlywed Jill thinks she's smart enough to win all her bets.
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Part 1 of the 5 part series

Updated 06/11/2023
Created 05/22/2022
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Ooshnafloot
Ooshnafloot
1,008 Followers

(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."

"You don't like guys seeing your body?" he asked, looking through the gap in the buttons at bare breast.

"I can tell you, if my husband came in here right now, he'd go nuts."

"Well, I've got your clothes here in my bag. You wanna change back now?"

"I don't know," Jill sighed. "Then it would look like I'm so stupid I didn't know what I was wearing."

"Up to you. Let me know if you want your clothes back."

"Eat your burger," Jill smiled, "Eyes to the front."

"Come on. I'm a guy. Your body is hot."

"You like it?"

"Best I've seen," Bobby said truthfully. And he saw a lot of it that day. Walking around after lunch through the market streets, Bobby kept as far apart as he could so he could watch and appreciate her body. In many ways, Jill was naive, not thinking when she bent forward or reached up, not noticing the gaping mouths of guys that saw her ass or the lips of her pussy.

"She married young," Bobby sighed, envying the shaggings her husband must give her young body.

After work Bobby followed her to the mall to change, soaking in the last moments of Jill's naked silhouette on parade. Once she was dressed, they had a coffee before heading home. Bobby praised her as a worthy sales colleague and someone he could trust to stick to her word.

"So...," he grinned. "What's the October challenge?"

"Not October," Jill said, feeling more comfortable after she was dressed sensibly again. "Annual billing. There's three months left. At the end of the year, we'll see who has the most."

Bobby burst out laughing. He was so far in front and he had more to bill. Jill knew about all of it. But he didn't know about hers. Amongst the giddiness of walking around the office with no pants under her short hem, Jill had received the email she was hoping for since June. Her big tender. The bosses had agreed to keep it under wraps and let the client announce first. It was her first Eastern deal. Even though they were in Hong Kong, all the existing clients were from Europe. This was the first from mainland China. And of course it was huge. The client would announce on New Year's Eve, as part of the celebrations, and in time to get the deal into this year.

"There's nothing you can do to catch up that much. If something that big was brewing, I would know about it."

"Then you don't have to worry," Jill said smugly.

"Oh yeah?" he frowned.

"Don't you think?"

"I think? What are you thinking? You must have something in mind...," Bobby frowned.

"I want your Porsche."

That made Bobby stop and stare, even more than he had at the gap in her shirt at lunch. His Porsche?

"Is that a joke?"

"No. If I win I get your Porsche."

"That's not going to happen."

"Me winning, or me taking your Porsche?"

"Either!"

"Right, so we have a deal?"

"Against what?!" Bobby laughed. "What have you got? A monthly bus ticket?"

"What do you want?"

Bobby leaned back and thought. There had to be a catch. No way could he be beaten, Jill knew that. Why was she putting dibs on his car?

"Well, come on," Jill pushed him. "Or do you give up?"

"You would really take my car?" Bobby asked.

Jill stopped to think. She wanted it, for sure. But if Bobby lost the year and the car, it would be a massive hit.

"Yes...but I'll buy it off you. The deal is you have to give me a bargain price for it. Thirty percent off whatever my husband's mechanic says it's worth."

"Are you serious?"

"Sure."

"You really want my car that bad?"

"I love it."

"But you're so far behind. What's the point?"

"Then no need to worry," Jill smiled.

"Okay," Bobby sighed. "At the company party. New Year's Eve. You wear a dress I pick out. No underwear."

'That's a given, knowing you," Jill smiled.

"And if someone tries to bed you, you let them."

"Okay."

"Okay?"

"It's a deal."

"There's some catch. Do you actually want to be fucked by someone? You want to lose, you want the punishment?"

"Of course not!"

"But... how can you even pay up? You're going to go back to someone's house and fuck them with your husband home waiting for you?"

"It's New Year's Eve. He won't expect me back 'til late, he's going out himself, I have time."

"Okay, it's your cunt. If you're happy to cough it up to someone on a bet, that's your choice."

"Do you have to use that word? I can use a condom right?"

"Of course."

"I'm fine, then."

"Wow. Are you really so easy to lay?"

"Only for bets," Jill beamed, thinking that Bobby would get the shock of his life on New Year's Eve. The company's biggest ever deal, all sourced by her.

Jill and Bobby spent October and November refining the details of their bargain, and all the time the comms and copy of the deal announcement went back and forth in secret. Jill booked the garage for the appraisal on January fourth, their first day back from the holidays. She readied the transfer forms. Bobby showed her the dresses he wanted her to try. To keep up appearances she went to some fittings, albeit leaving her underwear on. The one Bobby wanted was a mini-dress version of the dress Kang Han Na wore to the 2013 Busan Film Festival. If you see that dress, imagine a version so short that you knew her bare ass was just millimetres out of reach under the hemline. By default bare pussy, too. Jill would not let him buy it until they knew the result, but by early December Bobby couldn't wait. There was no chance he could see her pulling any rabbit out of the hat. No one had wind of anything small or big that was close to signing.

"You shouldn't have done this yet," Jill said, opening the bag. They were at the mall again, by the wheelchair toilet. "If you wanted to see me in it again, I could have gone to the store."

"You need to see it without your pants and bra, you need to know what you're in for," he warned her. With a head shake, Jill went in to change. Opening the door a crack, Jill invited him in to look. She wouldn't be wearing it New Year's Eve, so she took pity and let Bobby see it on her once with nothing under.

"Come in. I'm not going out there like this."

Bobby went in. Facing him, it looked like a regular little black cocktail dress, albeit with obvious braless nipples protruding and a length so short it showed her thighs curling open, it was so close to her pussy. Turned around, wow. Most of her back and two-thirds of her ass were nude through the lightest of mesh. It was clear that little dress was all she had on.

"These are the heels you would wear?" he asked.

"I think so."

"Face me again? Now lift your arms."

Sleeveless, the dress didn't pull up far. Holding the material, Bobby pulled the hem up to her waist.

"Doesn't slip up very easily," he said, stepping back to take a proper look at Jill's pussy. "You'll be safe enough until someone tugs it up like that. How come you leave that bit of hair at the top, why don't you just shave it all?"

Jill felt a rush of pride watching him stare between her legs and his pants bulge outward. She hadn't made anyone but her husband hard for over two years. Not knowingly.

"Are you really going to let someone use that?" Bobby asked staring at the gap between her legs. Jill's pussy lips fell down, slightly parted. Bobby was amazed the deal had come even this far.

"Won't have to if I get your keys instead," Jill beamed.

"You're a kamikaze optimist," he warned her. "You're going to get fucked. A dozen guys are going to try and get into you wearing that."

Jill smiled and turned around.

"You think they'll enjoy it?" she grinned cheekily as she spun around, leaned forward and stuck her ass out, teasingly offering her bare slit from behind. "You think they'll want to do me like this?"

"Does your husband?" Bobby asked.

"Of course. He enjoys very much."

"He's a foreigner, right? Not Asian?'

"Uh-huh."

Bobby was rock hard in his pants. "You must be stretched."

"Hmmm, it took a few dates 'til I felt comfortable putting him in," Jill lied. In fact, her husband had teased her from the outset that she was too loose.

"I need to go," Bobby sighed. It was all he could do not to reach out and run his finger through that bare slit. He could smell Jill's heat. "If I don't..."

"Go, go, let me change back," Jill said, kicking him out, before bouncing back home to look at car spaces for rent.

During the last proper work week before Christmas, Bobby was in his small office when all hell broke loose. Jill was screaming and swearing, wailing on Chloe, one of the comms juniors who was translating the contract. She had translated a message from the client as New Year's Eve, Dec 31. However, in Chinese the client had written Chinese New Year's Eve, without any date at all.

"How could you? You lying little bitch!" Jill screamed. Jill never ever swore.

"I thought I was being helpful, I put in the date," Chloe cried. Western New Year's Eve was Dec 31. Chinese New Year's Eve wasn't until late January. The big bosses literally had to pick Jill up and pull her away from pulling the girl's hair out. Whilst not the end of the deal, the error caused chaos everywhere. The start of the contract would roll into the following year, leaving a hole in the sales P&L and particularly in executive bonuses. And it wasn't just the junior in trouble. Fingers were being pointed everywhere, at all layers of management. In retrospect the error explained a number of confusing exchanges with the client in terms of location and availability of people for the signing.

For Jill, it came with a double hit. Suddenly December 31 took on an enormity in a way only she and Bobby could comprehend.

"Shit," she said, slumping her head onto her desk.

"What's wrong?" Bobby ducked in to ask.

"Ah," Jill sighed. "Delayed signing of a deal."

Bobby smiled, his eyes widening. "Holy shit. You really did think you were going to get my car!"

"Not going to happen now," Jill slumped again.

"Wow, you sneaky little thing!" Bobby teased her. "You had no intention at all of coughing up your cunt."

"Can you stop using that word?"

"No wonder you agreed so easily."

"Too late to change the deal?" Jill smiled weakly.

"Ha! This will be even more enjoyable to watch now, knowing how close I was to losing. Shit, must have been a huge deal?"

"Ugh. I don't want to talk about it."

"Oh baby, some lucky guy is going to enjoy this New Year's Party."

"I'm married," Jill said meekly.

"Well, why did you broker the deal?"

"Who do I have to do it with?" Jill frowned.

"The first guy to ask you to go home with him."

"No matter who?"

"No matter who."

"What if no one does?"

"In that fuck-me dress?"

Jill hmmphed. No chance. Guys hit on her in bars even if she was in her trainers. In that dress, so obviously naked underneath, no chance of being un-propositioned.

"I'm ill," she moaned.

"Oh no, you can come to my place before the party to change into the dress. We're going to have some fun that night."

"Grrr," hissed Jill, tossing a Hello Kitty pencil-sharpener at him as he left. Her poor Stephen. If he ever found out...it would kill him. Right after he killed her.

Ooshnafloot
Ooshnafloot
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1 Comments
auhound49auhound49almost 2 years ago
I would recommend one change...

Jill should not be allowed to use a condom, and it should be made clear she does not use the pill ether - let her risk her belly on the bet.

Your other stories all have preg risk sex, so why not this one?

I do like gambling with pregnancy. Perhaps in new stories you can have some type of bet where losing it may result in an unwanted pregnancy.

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