A Game Gamble

Note: This is a story written in competition with my wife, who is also a member here. We are seeing who can get the best rating, so feel free to take a moment to leave a rating or any feedback. There are stakes in play here people! Cheers

Emily felt a tingle of excitement as her mobile phone vibrated on her desk. She had been swapping messages with her new boyfriend, Henry, for a couple of hours. They had been seeing each other for a couple of months and the sex had been fantastic. Frequent, filthy and, above all, imaginative. They took a great deal of pleasure in each other and both found a certain thrill in trying things neither had ever done before. They had experimented with bondage, dialled up the dirty talk and started sending each other suggestive material whenever they could.

Today was Henry's turn to set the program and he had been toying with her all afternoon, making references to the tricks she was going to have to perform. Her desk job required a quite strictly professional appearance and sitting there in her buttoned blouse and dark rimmed glasses covered the ache in her breasts and slippery feeling in her damp pussy as she thought wildly about the possibilities every time the phone vibrated.

Slowly, she slipped the phone below the level of her table, spread her legs and hiked her skirt up, then took a photo and sent it off with the question, "How much do you want this?' She then made a respectable effort to pretend she was doing some work, flicking her eyes to the phone every few seconds to check for the telltale flash. After what seemed like an eternity, the vibrate sounded and she snatched up the phone and brought up her message. The answer read, "I want it. I want to own it. And I want to pay for it!"

She moved, and felt an almost unbearable urge to push her hips into anything that would resist her. They had played role-plays before and it drove them both wild. Schoolgirls, policemen, strippers and taxi drivers had all featured. The combination of submission and control in playing a whore made her want to rush into the role.

"Yeah Baby? You want to take a turn? I think I could find you some time. I'm in demand you know." She gave up all pretence of working and just sat staring at her phone until the response came.

"That's what the guys who recommended you to me said. You fucked three of my mates at a buck's night last month and they gave me your mobile number." The answer came. The smallest moan actually escaped her lips as she read it and imagined the scene he had described. She desperately wanted to respond immediately but just then a co-worker dropped by her desk to ask her about some mind numbingly boring report. This happened a lot. There was quite a group of young staff in the office and her blonde hair and full round breasts meant a decent proportion of them spent the day passing her by and trying desperately to flirt with her. She didn't discourage it. It did make the day go faster and she enjoyed the way they would hover abover her and pretend to be looking anywhere but at her cleavage, pushing out of her slightly undersized top.

Now, however, she had games to play and just wanted a moment. If anything, her breathless flush clearly added to her drawing power and it was several minutes before she could muster a stern enough look to send her admirer scampering. When she looked back at her phone there was another message waiting. "This is how it's going to work Emily. If you want to do this, it's going to be real. The next message I send will be to my hooker. You can negotiate however you want. I'm sure these girls have their own rules! But whatever rules you set will be genuine and I WILL be paying you whatever we agree. Let's be clear, I want to fuck you for money and I want you to be in it for the money. And I want you to go straight from work to buy an appropriate outfit from scratch and be ready for our meeting tonight. Remember, the cheaper you look, the more you earn. On top of your earnings tonight, I will pay you tomorrow for anything you spend. The only rule I'm setting is you can't break character. If you do, you get paid nothing, and I'll still use you like a hooker. So, if you don't want that, just say so and I'll happily take you home and fuck your brains out as usual. But, if you do, just text me back the name you want me to call you tonight."

Emily couldn't possibly stay at her desk to process this, so she snatched her phone off the table and made her way to the women's toilets. Once there she rushed into a stall and locked the door behind her. Then she sat on the seat and slowly read through the message again. Almost automatically, she stood and pushed her pencil skirt down past her knees, letting it drop to the floor and kicked it off one foot so that she could sit and start to spread her legs a little. Then she lifted her arse just enough to slip her stockings down along with her knickers. Leaning back, she held the phone up and began to read the message again, slowly, as she started to stroke her clean shaven, moist pussy with her right hand. Soon her hips started moving as her fingers got faster. She closed her eyes and began imagining the scene henry had described. She imagined herself dressed as a slutty hooker standing on a street corner and waiting for him to drive past. She dreamt of the conversation as she leant through his window and told him the things he could do to her and how much each would cost. Almost dropping the phone to the floor, she clutched at her left breast and began massaging it hard, no time to stop and unbutton the blouse. She grabbed at her nipple and tried to pinch it as hard as she could, picturing being fucked hard at the side of the road and walking away with smeared make-up and holding some crumpled cash. Pounding waves of orgasm began to crash through her and she braced herself against the left wall and stretched her head back and tried to dampen the moans escaping from her throat. Slowly, she came back to consciousness and looked down at the phone still clutched in her damp left hand. She licked her lips, pushed some stray starnds of hair out of her face and typed the word "Jamie-Lynn" and hit send.

After leaving her cubicle, she spent some time in the mirror trying to look slightly less like someone who has just had a mind numbing orgasm, before leaving and heading back to her desk. She slowly managed to get her day going again, even spending a few minutes concentrating on her job, before the phone buzzed again.

"Hi Jamie-Lynn, my name's Henry. I was given your number by a few friends who saw you last week. I'm in town tonight and was wondering if you might be free to see me?"

After thinking about her response for a while. She tapped out, " Sure Henry. I have a few appointments but can meet you about 9pm. Your friends weren't lying, I'm worth waiting for."

"I bet you are, my friends have talked about you non-stop since seeing you. I have a room booked at the Grand Chancellor Hotel. Can you meet me in the hotel bar? How much money should I bring?"

This made her smirk. It might be his game but she wasn't going to make it that easy for him. " Sure, I'll meet you there at 9 Honey. We can talk about arrangements when we meet. Sorry, two guys have just arrived and I'm going to be busy for a while. You just think about what you'd like when we meet."

She then slipped the phone back onto her desk and tried to get some work done. Her mind kept slipping back to the evening's plans though. However, when a couple of messages came though from Henry she studiously ignored them. After all, if she was in role he could hardly expect her to be answering messages while sucking off strangers!

Finally, the day ended and Emily grabbed her things and headed out from the office. She worked quite close to the city centre and knew there would be no issue with finding stores open to browse for just the right costume. She decided to start with the easy things first and walked into a pharmacy to buy some make-up. She had plenty at home but liked the idea of browsing with the object of buying whatever looked the most whorish. Soon she had settled on just the right shade of red lipstick and some matching nail polish. Then she chose some dark mascara and at the last moment decide to add some long and delightfully curled false lashes.

Next was a trip to a costume jewellery shop. She removed her own small ear studs and bought a big pair of gold hoops. Big enough that she could easily slip her hand through them, and then a bundle of cheap bangles. Mostly gold, but a few brighter colours as well. Once she had at least a dozen on each wrist she practised moving them in front of her face. She liked the sound they made and giggled, thinking about the possible distraction once she started giving Henry a hand job with them.

Finally she took a deep breath and wandered into a clothes shop. It was a typical young person's fashion store, which seemed to stock everything from denim through to latex and faux feathers. The prices were quite cheap and the actual work probably left a fair bit to be desired, perfectly in keeping with the goal here she suspected. Emily began browsing through the racks trying to decide exactly the look she was going for. The shop attendants, like most of the customers, appeared to be between 17 and their very early twenties. At 27, they probably viewed Emily as something of a dinosaur. But she didn't mind that, confident that when she dressed to turn a man on, she would have them all beaten. The question of price gave her a thoughtful pause. It was no seceret between them that Henry made a lot more money than she did. Not that she was on the poverty line. But since starting to date hime she had gone to restaurants and shows which she would never have been able to afford yourself. Tonight he seemed determined to pay to make the experience more 'real', and since she knew that she would be up for anything he suggested anyway, she certainly wasn't going to refuse to accept the money on principle. In fact, the idea of being paid somehow made the whole thing even more of a thrill for her. On the one hand it made her the professional and so some sort of authority. On the other hand she then became an employee and would 'have' to do what she was paid for, she had plenty of experience of that at work!

So, how did that affect her wardrobe? Does an expensive whore dress differently to a cheap one? And which did she want to be? There was no denying there were a lot of unpaid bills sitting on her desk at home. And yet, somehow, the idea of doing all sorts of unspeakable things and only charging 50$ seemed to turn her on more than charging 500$!

A perky 18 year old red head bobbed up behind Emily and broke her reverie by asking if there was anything she could help with. Emily was about to brush her off with a polite shake of the head when she couldn't resist the urge to prove that fun didn't wither away and die at the stroke of 24. "Actually, maybe you can," she mused, "I'm attending a surprise for my partner and I want something a little but special for him."

The girl nodded with a smile and said, "Something a bit sexy, then?"

"Sort of," Emily replied, and became a bit stuck. She hadn't really thought through how far she was going to go in explaining. "really, it's a kind of dress-up costume that I need."

"Ok," the girl responded and smiled again, "what will you be going as?"

Now or never Emily thought. And after all, I'll probably never see this person again. "A hooker!" She stated bluntly and tried to soften it with a smile, matching the bubbly little thing grinning back at her and wearing a name badge that said Erin. Erin didn't stop smiling but had that momentary pause which told Emily she was having the same trouble in deciding on the best response. Somehow, starting had opened the flood gates for Emily though and suddenly she felt that she could see the fun in the situation. "It's like this," she continued, "my partner and I are playing a little game. It's his birthday (she lied) and I'm going to surprise him with a little role play. And since I'm normally always dressed quite conservatively, I just thought that tonight I would do something a bit unusual. So, I want to dress up like a prostitute for him and give him a thrill."

Whether it was just time, the greater explanation, or just the friendlier tone was unclear, but Erin immediately relaxed and her grin somehow managed to get even wider. "Cool!" she said and this time it seemed like something more than an automatic response she gave 25 times a day while staring at her phone. " Let's start looking." She almost grabbed Emily by the hand and started taking her around the store. Inevitably, a couple of her bored colleagues eventually noticed that this was more than a standard job of direct-the-customer, and when one with beautiful olive skin and dark hair wandered closer Erin couldn't resist filling her in and suddenly the group became three young women, eagerly seeking out the sluttiest combination the store could offer. After twenty minutes they all retired to the change rooms with a few armfuls of options. For an awakward moment Emily wondered if they were going to try and push into the change rooms with her. Instead, they managed to block off the area and bundle her into a curtained-off room while shouting out advice on which combination to use. After each change Emily would pop out and do a twirl, accompanied by wildly encouraging remarks and some suggestions. It was turning into something resembling a bizarre hen's night.

Eventually they all agreed on a combination. She was wearing quite a tight white tank top with thin straps and a low cut scoop neck. This allowed her boobs to leap quite alarmingly from the top. Their beautiful white skin spilled up to the point where it seemd nipples must follow. And at Erin's insistence she had also chosen a red bra with a high frilly cup so it was plainly visible under the straps of the tank top and all the way along the top of the cups. It was even visible under the shirt itself. The tank top was short enough to leave her pierced belly button on display. Under that she wore a black faux leather skirt with severel chunky looking zips and studs. She was definitely very much the hooker that Motley crue would allow on the bus.

Under the skirt was a red gstring to match her bra and some very dark stocking she had intentionally put a couple rents in. And finally some high heeled stilletos made her feel that her legs were on display and her arse pushed up in the air. Her new friends all gushed about the look and how she could add to it with accessories. When she admitted that she had already bought some they flat out insisted that she duck back into the change room and complete the look for their approval. When she finally came back out, the transformation seemed complete. If her glasses still made her look bookish, she looked like the most bookish hooker in town. As a final touch the girls added a dark black handbag for 'professional essentials' and a heavy stone necklace designed to make sure her top stayed pulled down between her breasts. This last was a cheap item and the grils tried to insist that Emily accept it as a gift from them until she explained that Henry was paying for everything anyway. They laughingly agreed that he was going to get more than his money's worth and could foot the bill. As she tucked her credit card, keys and phone into her new bag the girls asked if she minded if they had their photo taken with her. "Sure," she smiled and struck a few poses with her boobs and ass stuck out at improbable angles. As she waved goodbye, Erin went to tag her photo and called out, "I never asked you your name." Emily, flicked her red coated finger tips in a wave and said "Jamie-Lynn" over her shoulder.

It was now about 8.30 pm and she was about ten minutes walk from the hotel. As she strode from the store she knew that most of them women she passed and all of the men gave her a second look. She figured a good proportion figured her as exactly what she was 'meant' to be. What the others must have thought she had no idea. The problem she had not anticipated was what do with with her regualr clothes, shoes and bag, which were all now stuffed into a couple of shopping bags. She lived far too far away to make a trip home, and she figured taking a bag of day clothes probably counted as breaking character.

The only option was to quickly run her bag up to her office. It was only a block away and there should be no-one left at this time. Would any of them even recognise her in this outfit? She tottered to her building, occasionally catching sight of herself in windows and uable to resist checking herself out. Provocative yes, but there was no denying that the only word to describe her appearance was sexual. Even if you didn't want it, the whole look from top to toe screamed sex. And she was beginning to feel her chest push even further out every time she caught someone staring at her boobs from the corner of their eye.

She reached her building and sighed with relief as she made her way across the empty lobby and caught an elevator up to her floor. From there she made her way through the door of her company and quickly stuffed her bag beneath her own desk where it would be fine until Monday. She spun and made her way back through the maze of desks. Half way there she froze as she saw a door open and a man, with his head down make his way towards her. Unable to move she recognised the wavy hair of James, one of the friendly young things that found a reason each day to spend at least ten minutes hanging over her desk. Becoming aware of someone else in the destered room he stopped abruptly and looked up. It was clear he did not at first even recognise her and simply wondered who the hell had managed to find their way in here late at night. Meeting her eyes at last she saw the jolt of recognition.

Before he could say a thing she stammered, "You're here late." Nothing like the bleeding obvious to break the ice.

"Umm yes, I am," he added, obviously agreeing with the sentiment. "Are you out... with friends?" he gulped.

"Not really," she answered, but then suddenly realised that that probably left her needing to offer an alternative. "I'm about to meet someone, for an appointment." She finished weakly, slowly letting the possibilities of that statement sink into her own mind.

James did not seem to reach any definite conclusion but after staring so long at her breasts there was a real danger of him falling into a coma he seemed to remember this was a girl her knew and found his voice. "Anyway, I, um, have to go now, was just leaving anyway.." and he stepped back in the direction he had just come. As much as she knew he had said that to allow himself an escape, Emily now had no real choice but to follow. She could hardly claim that she had been on her way to sit at her desk and work. So they walked in silence out to the elevator. Then he pressed the down arrow and they stood umconfortably until the elevator arrived. Emily nervously pushed her hair back from her face and was painfully conscious of the dozen bangles clattering on her arm. It also reminded her of the heavy stones sitting between her prominent breasts and pulling her top into her body.

When the elevator finally opened, James entered first and stood at the back of the small space until Emily entered and turned and stood in front of him. Once the doors slid shut, the smooth metal surface was reflective enough that she could clearly see him behind her ogling her arse and legs. At least he was confortable enough now he felt he wasn't being watched. Emily found that not having to meet his eyes meant that she could now actually enjoy the obvious effect her appearance was having. She ran her hand back through her hair and flicked it free down her back. Then she let her hand sit on her hip so she could show off her nails at the same time as making sure her arse was accentuated. When they finally reached the floor she stepped out and threw a smile back over her shoulder, "So, I'll see you Monday." She told him with a smile and a wink.