A Game gamble

"Sure," he replied, "Monday. And have a good, appointment." He added with raised eyebrows.

"Oh, I will," she said with another smile. "And so will he!" Then she turned and walked out of the fornt doors, with her stiletto heels making a clear clicking sound on the marble floor that she knew James would be hearing in his sleep that night.

Leaving her office she started making her way back to the hotel. About half way there she had a sudden thought and decided it wasn't too late to pick up a last couple of items. She popped into an open chemist and headed down the first aisle. Ater a couple of minutes searching she looked up to see if anyone could help her, she was running late after all. Two girls were working behind the counter and both were watching her walk the aisles but showed no interest in helping her. It suddenly dawned on Emily that they probably weren't simply entranced by her, they were trying to make sure she didn't steal anything. Fine! There's one way to deal with that. Sticking her boobs out as far as they woud go and tossing her hair over her shoulder she walked slowly up to the counter where a rather prim looking, middle aged woman raised her eyebrows and asked pointedly, "Can I help you?"

Emily stared directly into her eyes and without blinking or glancing away answered, "Sure, Honey. I need a 6 pack of condoms and some lube." They both stared at each other for a moment and Emily felt a thrill when eventually the assistant broke eye contact first and reached under the counter and dropped the two items on the counter. As they were rung up Emily casually picked up a pack of tutti frutti bubblegum from the counter and waved it and then ripped it open and popped a piece in her mouth and began chewing lazily.

"That will be 11.99 please," the woman managed to get out and without responding Emily pulled a crumpled twenty from her purse and handed it over. Then she slowly pushed all the items into her bag and walked out. There was no question now that the overwhelming feeling of knowing that her arse was being stared at was one of unalloyed pleasure.

Emily walked on to the hotel and strode across the foyer. She knew she was now about ten minutes late but figured a little anticipation could only add to the thrill. As she entered the bar she knew that she caught the attention of everyone in it. There were probably twenty people scattered around the room in small groups, although only 3-4 women. She spotted Henry immediately, sitting at a table by himself, but without making direct eye contact she made her way to the bar and sat down. The barman approached her with a smile and asked if she was after anything special. She smiled and asked for a martini. As the barman went to mix it up, Emily glanced around the room and noted a few men smiling in her direction. She returned their smiles and crossed her legs easily.

Henry walked up to the bar behind her and cleared his throat. She could swear there was a hint of nervousness. "You must be Jamie-Lynn."

Emily smiled and extended her hand. "Well, hi, I'm glad you got in touch, I hope we can have some fun tonight."

Henry stood for a moment and appeared unsure of what to do next. Suddenly, the bartender appeared and placed her martini on the bar in front of her. Emily turned back to him and gave him a big smile. "Thanks Sweetie, just pop it on his room account," she said tossing her head in Henry's direction.

"Certainly," smiled the barman. "What is the name?"

Emily looked coyly at Henry and gave him an apologetic grin, "Sorry Darlin' I've forgotten your name."

Henry looked taken aback for a moment and then stammered, "uhh Henry Stafford. Room 478" The barman smiled again and wandered away to the till while Emily got up and carried her drink back to Henry's table. She sat with her back to the wall so that Henry had to sit facing her and she could easily watch the room. There were several tables nearby which would not have too much trouble overhearing an average conversation.

"Hard day at work?" Henry asked, taking his seat with a beer. She thought about her response and decided to see exactky how much fantasy he woud like.

"Well, if you must know, I got a little tied up," she then flashed him a wink.

"Do you get a lot of that sort of thing he asked," and hesitated, "you know, kinky stuff?"

It seemed like he wanted some details, so Emily took a sip of her drink and smiled at him. "The customer always gets what they want. So I guess there isn't really much that's off limits, if the price is right." She gave him a knowing look and she could almost swear he got stuck mid swallow. "I mean the main reason guys ring a girl like me is they want to do some stuff they just can't bring themselves to ask their girlfriends or wives for." She slowly took another drink and let that sink in. Glancing around she noted that there were a couple of tables near them where the conversation seemed to have died off.

"So what do you actually like?" Henry managed to ask her.

"I like to get paid," she replied and smiled to lessen the bluntness. "But I also really like the expression a guy gets when he carries out a fantasy he's had for ages and not been able to tell anyone. You know, a mixture of disbelief and gratitude. Just recently, I was with a college student and he was so thrilled to fuck an ass for the first time, I couldn't help smiling. And that was tough, because he had a pretty huge cock and really fucking stretched me out." After that she settled into the silence that descended on the whole corner of the bar and sipped the last of her cocktail.

"God," Henry whispered. "So, how much for that?" Emily took a couple of thoughtful chews on her gum and leant across to run a hand up Henry's leg.

"Sweetheart, why don't we go back to your room to discuss that, we might be able to get a little more comfortable."

Henry nodded dumbly and they both got up to walk out. As they stood waiting for the elevator she slipped her hand into his and whispered, "Don't worry, Henry, I'll take good care you get exactly what you want." They finally reached his room and Henry walked in first and then turned and stood a little awkwardly. Emily followed more slowly and cast a professional eye around the room. Then she put her purse on the table and gave him a smile. "Why don't you fix me a drink, and you should have one too if it will relax you, I'm not on the clock yet." While he poured two drinks she stood in front of the mirror and generously reapplied lipstick.

When Henry approached with the two drinks she left him with one in each hand for a moment and gave him a far more girlish look than any she had tried so far. So, you asked about prices?" He nooded and stared down at her bulging tits. "Well," she drawled slowly, as she reached forward and gently grabbed his rock hard bulge through his pants. He started suddenly and almost spilled both drinks. "Sorry," she murmured seductively as she unzipped his fly, "but I like to take a certain precaution before discussing prices. I just need to know you're not an undercover cop. They generally won't allow me to do this." Saying that she quickly pulled his penis out of his pants and gave it two or three quick pumps. She really enjoyed the feeling of the bangles sliding along her forearm as she pumped his beautiful hard cock. Satisfied, she then tucked him away and took the drink out of his shaking hands, pausing only long enough to lick the tip of her finger.

"Well, assuming you can get what you need done in an hour or less it's 100 bucks for a hand and blow job, for which you can cum in my mouth or on my face. 200 for sex, with a condom, or 300 for anal, ditto on the condom. Or since it's my last booking for the evening, for 400 you can just have me here for as long as you want me and fuck any hole you like as many times as you can get it hard. Of course 'extras' are negotiable."

"Extras?" Henry asked, as she had hoped he would.

"You know," she shrugged. "If you want to bring in any friends, if you want to film me, or do me bareback, or," she almost tailed off, "if you'd like to get a bit rough." Henry met her face and slowly took a sip of his drink. After another moment he pulled out a bulging wallet. He pulled out a wad of fifty dollar notes that were bound in a small rubber band.

"There's 500 dollars. For that you stay here as long as I want. I fuck you any way I please, without a condom, and I talk to you any fucking was I please, and you do as I tell you. And that includes telling me every slutty thing you've ever done."

Emily gave him a open mouth smile and licked her lips. Holding out her hand for the cash she said, "You've got yourself a deal, Babe."

But Henry did not hand over the cash straight away and appeared to enjoy seeing her holding out her hand expectantly. "Or..." he said, and slowly pulled out three more identical bundles and held them just out of her reach "... there's 2000 dollars."

Emily pulled her hand back and stared a little open mouthed. For the first time she realised she may not be the only one trying to run the game tonight. Unsure of what to do, she put her hand back on her hip and tried to look like this sort of thing was a regular occurrence.

"The 2000 dollars," Henry went on slowly, "is for a blow job." And then he appeared to weigh the cash in his hand and looked ready to wait as long as it took for Emily to make the next move.

"So, what's the catch?" Emily asked. "I've already accepted 500 to be used for anything you want. Exactly how do I earn 2 grand for sucking your dick?"

"I'm sorry," Henry replied, feigning a little confusion. "I haven't been very clear. The blow job is not for me. You have to earn the blow job, and you will have to be reasonably confident in your ability to get just about any guy to stick their dick in your mouth." Henry then smiled openly. She felt he was enjoying playing the role of gamesmaster as well as using graphic language he had never used with her before.

"Here's the 'catch'. You can choose the 500 now and we can get started. I don't think either of us will be disappointed. Or, I ring down now for a bottle of champagne. In a few minutes whichever poor schmuck they have working at this time of night will bring it up to the room. You accept it, invite him in and then before he goes I want you to suck him off. And I don't care who he, or she, is. You take your chances. If it's an 18 year old stud or a 65 year old happily married woman who's pussy you have to try to get your tongue into. If you can get them to orgasm with your mouth you get 2000 dollars. But..." and here he paused with one finger raised, "if you fail then you still have to stay here and be used like a whore by me all night, but you get paid nothing for it. You'll leave here with a sore pussy, a sretched ass and a valuable lesson in humility."

Emily had to admit she was confused enough to have no idea what her immediate response was. She had the presence of mind to avoid blurting out anything that would break the scene but she paused and covered her hesitation by going to the bar and opening another 2 small bottles of bourbon. She then sauntered back to the middle of the room and handed one to Henry as nonchalantly as she could.

"And are you joining in this little exercise," she asked. "After all, you're paying. Or are you just going to trust me when I tell you I've gotten a mouthful of cum?"

"I'll stay," he said, pouring out his drink. "Before they arrive, I'll be out on the balcony, and they'll have no idea I'm there. I want to see how hard you are willing to work to get a cock in your mouth when there is 2000 dollars at stake."

Emily slowly started her second bourbon and chewed loudly on her gum. Henry was giving her an intense look. There was no indication of his thoughts. She couldn't decide whether he really wanted to see her suck on a stranger's cock, or if he was hoping she would accept the challenge and fail. Would he be excited by the spectacle of her trying desperately to pick this guy up, behaving like the hooker she was supposed to be, and by the thought that he would then get to use her for free. Or was he hoping she would decline the challenge and he would somehow 'win' the game by having been willing to go further than she was.

He was beginning to smile now. She still had no idea what he really wanted but she knew he was enjoying being the one in control. So, what did she want? She had been loving the game, she loved having the license to behave as explicitly as she wanted and the thought of spending money on whatever she wanted while thinking back to the way she had earned it. The truth? She wanted to take the bet. She wanted to show Henry that she could get any guy she wanted to want to fuck her pretty mouth. She wanted to know he was watching her as she took some stranger into her mouth. And, she wanted 2000 dollars! Could it back fire? Yes. It could be someone she was not attracted to, a disgusting old guy or a woman. She had never been with a woman before. The idea didn't turn her off, but presumably she would be less likely to succeed. And what if she failed? Then she would have to be a whore for nothing. Putting all other thoughts out of her mind she looked at Henry and thought about what she most wanted to be doing in 20 minutes time.

"Make the call."

Henry nodded slowly and walked to the bedside table. He turned his back to her and dialled the phone. After just a moment she heard him say, "Yes, this is room 478, Henry Stafford. I'd like a bottle of Bollinger brought up immediately. Thank you." He hung up the phone and turned to look at Emily. Neither of them said a word, but she tossed her hair back and stood tall, throwing her chest out, daring him to be the one to break the deal. But after taking a slow drink he walked to the balcony door and stepped through into the night. She looked and realised he was right. With the change in light and reflection on the glass there was no way that anyone standing inside would be able to see anything outside. She could see her own reflection staring back at her. She smoothed her black skirt and casually repositioned her breasts making sure everything from the top of the nipple up was visible. It was more than visible, it was prominent and inviting. There was little doubt that whoever knocked on the door would be clear as to what was on offer.

She loved the idea that Henry was standing out there in the dark watching her. Would he like it? Would he masturbate and cum seeing her kneeling for a stranger. In the complete silence of the room, the knock on the door almost seemed to momentarily suspend her heart. Turning away from the window she walked down the short corridor to the door. She stopped and took a deep breath and resisted the urge to look through the peep-hole. She had made her decision and she now wanted to start. Trying to get a peek now could only make her second guess herself.

She opened the door and her first thought was relief that it was a guy. She noted he was much taller than either her or Henry. He was probably 6 foot 1 or 2. However, he was also significantly older, perhaps late 40's or even 50. He wasn't unattractive but to be honest, in no way the kind of guy she would normally look twice at. Be that as it may, she was certainly loking at him now and he took a quite comical double take as she opened the door wide. But his training took over and he soon flashed a controlled smile and enquired, "Bollinger, Ma'am?"

Emily stood back and waved him into the room and smiled as he pushed a small trolley past her. Closing the door she followed him down the corridor where he stood and looked around. He seemed a little surprised to see no-one else in the room, yet he was unruffled as her turned to her. "Would you like it opened?"

"Sure," Emily replied and came close to freezing. How do you ask a guy you just met if you can give him a bow job? Do you ask, or do you just drop to your knees, open your mouth and assume he's watched enough porn to do the rest?

As he popped the cork she looked again at his size. There was something very prepossessing about a guy of his size and she found herself wondering briefly if his cock was to scale.

"Just the one glass?" he asked as he began to pour.

"Sure," she answered. When he finished pouring, she continued, "I had a date, but he kind of cancelled on me." He held the glass out to her but she did not step forward to accept it immediately, as she became worried he would leave oearly if he had the chance and she would miss her opportunity.

"So, here I am alone... Michael," she pouted, looking at his name badge. For just a moment a brief look of surprise flittered across his face. She chose the moment to step closer to him. "Any chance you can share some champagne with me?" As she took the glass she made sure her fingers closed around his and did not remove them but held his eyes closely.

"Aaah I'm afraid I really can't," but then tapered off, if he had planned to offer a reason it must have gotten stuck somewhere between his brain and his mouth. Most importantly he had not yet gone anywhere and Emily noticed how often his eyes flicked down to her breasts. She followed his gaze down and when she did she noted with something like surprise how close her left hand, the one not wrapped around the champagne flute, was to the front of his trousers. Looking back up and catching his eys she bit on her lower lip. She slowly moved her hand forward and allowed her fingers to brush his cock thorough his pants.

Michael swallowed hard but, again, stayed still so Emily decided to go for broke. "I just promised myself some action tonight and now I need a cock or I think I'll have a breakdown. I promise I won't be long. That OK?" Michael was still standing with a bottle in one hand and her hand in the other but eventually he grunted a gruff, "Ok." and seemed to shudder from head to toe. Emily left him holding the flute and sank to her knees in front of him. When she lifted her hands to his fly she was worried her boobs might pop out of her top. The thought of Henry standing on the balcony watching her go to work flew through her mind.

When his fly opened Emily slipped her hand inside and pulled his rapidly hardening cock out. It was already longer than Henry's and considerably thicker, she could see he was not circumcised and veins ran on all sides. If she held her knees and back straight her eyes were just level with the swelling head. She started to move her right hand along the shaft while using her left to remove his balls from the front of his pants. Her slow powerful movement was accompanied by the rhythmic slide of her bangles up and down her forearm. Michael groaned once when she first opened her mouth and rested his head against her bright red lips. She made sure he looked her in the eyes before starting to move her lips forwards down his thick shaft.

He muttered a quick, expletive under his breath and reached over to the trolley to put the drinks down. He then stretched his hands down by his side unsure of what to do,. "Sit on the bed," she told him, pulling his pants down below the knees. He really only had to take one step back to do so. When he did she crawled forward before kneeling again between his now slightly spread legs. Now by kneeling up she was almost at his eye level and she found it easier to start pumping his cock and moving her weight backwards over her heels. He seemed unsure of what to do with his hands again. "You can use your hands on the back of my head if you want. I like to have my face fucked." This time when she bent forward to take him in her mouth he grabbed two handfuls of her blonde hair and groaned as he pushed his thick cock forward into her face. Soon she was moving steadily up and down his cock and could feel her hair and huge earrings banging into the side of her face. This was the part of cock sucking she had always loved. The feeling of momentum building towards orgasm and the heat of a guy who just wants to push harder and harder.