Riley went with her four best friends to Las Vegas as a summer vacation from their jobs. Each woman was in her late twenties and just establishing themselves in their various careers. After years of school and early success at work each of them wanted to do something special to celebrate being young, beautiful women.
The ladies knew each other from their college volley ball team, so each was tall, fit, athletic and confident in her physicality. As such they had collectively made a pact for this trip. All the ladies had sworn to indulge in any reasonable offers they got from men during their vacation. None of them had boyfriends currently; that was a condition of the journey, and the pact was that they would all get laid at some point this trip.
Riley wasn’t one to sleep around, she was no prude, and had as high a sex drive as any of the women on this vacation, but she usually found men to be unimaginative in their approach. Riley was intelligent and enjoyed having her brain stimulated as much as her body.
So as she and her hotel roommate Cassie dressed for the night Riley was cautiously optimistic about her chances of meeting a man worth bedding tonight.
For this first night the ladies agreed to dress their best for a night on the town. Riley wanted to look accomplished and alluring so she wore a simple, elegant black dress that showed her figure to its best advantage.
The hem was high and showed off her long legs to great advantage. Her lean limbs were toned and sculpted from years of aerobics and jogging and the recreation league volley-ball the ladies all still competed in. Her bare arms were tanned and firm, not an ounce of fat to make her hesitate to show off. Her back was exposed in the dress, and showed no tan lines, as she enjoyed lying out topless in her back yard.
The front plunged further down than any of her friends dared because Riley had the smallest breasts of the group. Her A cups were taut and firm, but small and perky. Her constantly hard nipples poked through the thin material, but she had stopped worrying about that years ago, accustomed to the attention her chest drew went she went out.
She wore her long golden hair down so it could cascade over her shoulders and back, the soft tresses caressing her sensitive skin. Her make-up was subtle and classy showing off her high cheekbones and elfin features to great advantage, her hazel eyes seemed warm and inviting when she glanced at herself in near-by reflective surfaces.
Riley didn’t really think any of them would actually find a partner on the first night. All of them were intelligent, considered women, not prone to wild indulgences, and so as the ladies began to play games in the casino she paid little attention to the men that began to gravitate toward her and her attractive friends.
Wherever they went, from table to table, and even switching casinos the group of them drew men to them like magnets. The six of them were between five foot six and six foot one, and in heels Sonja, the tallest, was six foot four. They all wore sleek sexy dresses over their lean, tanned, athletic bodies and men flocked to them whenever they stood still long enough to be approached.
All night they didn’t pay for a drink as men approached, individually seeking to cut one off from the herd, or as groups of other vacationers hoping to set up an even bigger party.
Riley herself was asked at least three times if she were an escort. At first she was very insulted until she spotted and eventually spoke to an actual escort in one hotel casino. These women were everywhere and looked just like she and her friends; beautiful single women dressed up nicely wandering the casino floor.
It was an exciting evening, and Riley was more than a little tipsy from all the free drinks, as well as being high on all the attention from men. Riley was used to being hit on, in college she had even dabbled in modelling, so she was attractive enough to draw attention pretty much anyplace she went, and at five eight, thin and blonde she knew on some level that she was a type often idealized in the media as a being “perfect”.
Riley didn’t see herself as perfect, but she knew she was pretty. Yet, even so, tonight was crazy. Every which way she turned men were looking at her, assessing her, lusting after her and she found the attention overwhelming.
Yet it was also arousing. Suddenly for the first time in her life she understood her power as a sexual being. Looking around the room right now she made eye contact with as many men as she could. Every man who met her eyes looked longingly at her and studied her figure and face, some smiled, some didn’t, but they all raked her with their eyes.
It dawned on her that she could sleep with any of these men. It might take a little more work with some, but none would prove difficult. Not here and now, in Vegas, in these hotels.
The realization made her horny. It was embarrassing too, but arousing more than anything.
She was standing near the back poker tables, and clusters of players and non-players were grouped around the small tables watching the intense action of high stakes poker. The limits at these tables were higher and the players better than elsewhere on the floor.
Riley made eye contact with a man in a very nice suit, he looked to be in his early forties, tanned lean and confident. Something about the way he was looking at her caught her eye. He seemed more wistful than sexual. His posture, although seeming calm on the surface, looked on some subtle level frozen, or even nervous.
Whatever it was, Riley met his gaze and she too stopped in her scan of the room. His eyes caught hers and they shared some kind of significant moment she couldn’t explain. She was sure they had never met, but she felt intimately connected to him immediately.
The eye contact lingered for a moment that seemed poised on the edge of something almost dangerous. Then he broke the looming sense of danger by smiling a warm friendly smile that utterly disarmed her. His smile seemed bashful, self-deprecating and amused. He shook his head as if laughing at a private joke and he sort of half shrugged as he looked back and saw her still watching.
When he began to move toward her as she stood staring back at him Riley saw that he moved smoothly, like a dancer or something, every limb in perfect harmony as he negotiated the ten feet between them.
“Hello. I apologize for staring. I hope I didn’t bother you.” His voice was low and smooth and he spoke just a hair too quietly for the volume of the space. Riley instinctively moved closer to hear him speak and found herself brushing her arm along his.
“It’s funny, but for a second I wondered if we had met before or something.” She said, her own voice sounding high and weak after the confident tone in his.
He stood just over six feet and Riley in heels was five ten, so she was happy that she had to look up into his warm blue eyes. His dark hair was short and wavy, and she had a strong urge to mess it with her fingers. His strong, handsome features reminded her of an actor, but at the moment she couldn’t think who. Riley found herself attracted to him and hoped he was single.
With a flash of his white teeth the stranger smiled back at her, “I had a similar sensation myself. It was a little unnerving if the truth be told.” There was something about his voice, a slight accent, a certain delivery that thrilled Riley. It was intimate and familiar in ways she couldn’t process. “My name is Josh, pleased to meet you.”
He took her hand and as they shook, his warm, slightly callused palm pressed to her own soft one, Riley felt a true frisson of pleasure tingle along her nerves at the contact. “Hi. I’m Riley.”
A look of sadness flashed across his eyes as she said her name, and she felt his hand release slightly from her grip, but instinct told her to hold on to him and she squeezed his hand slightly as he appeared to begin letting go.
They finished the handshake with a couple more gently pumps of their hands and then let go more organically.
“Well, it’s been nice to meet you… Riley.” The slight hesitation before her name was full of emotion, and Riley felt herself immensely curious about this man. He appeared to be excusing himself and Riley was at a loss as to how to keep him talking to her, or why she should. He was older and obviously very wealthy from the look of his clothes, he wouldn’t be interested in her, a physical therapist that made less than forty thousand a year.
He turned away, then stopped and turned back. He flashed a rueful grin and asked, “Have you ever seen the private poker room?”
Riley was so happy that the interaction would continue that she didn’t even hesitate, “No. I would love to though.” She could care less about poker but she wanted to spend more time with this compelling man.
“I am on the list, and should be called in soon. It might be boring watching a bunch of professional poker players- I don’t know if you play, but you are welcome to be my guest. You can’t play, but then again you need a pretty big pot just to get on the list, so…”
“I’m good just watching. I’m really curious.” She sounded so young to her own ears. Everything she said when compared to how he spoke sounded childish to her ears.
“Great. Shall we?” He offered her his arm and she slipped her own through his without any hesitation.
It wasn’t until they were across the room that it occurred to her that she might want to tell her friends where she was going. Looking back quickly she saw that they were all out of sight already. With a mental shrug she figured she could text one of them when she was inside the poker room. She felt no fear; she was in a crowded casino going into what was likely a highly secure room.
The next few minutes impressed Riley by an order of magnitude she was challenged to accept. The opulence of the room, the deference of the staff, and the ostentatious show of wealth all stunned her more deeply than she would have imagined.
Riley realized that she was suddenly moving in a circle so far beyond her norm that it may as well have been another planet. The clothes, the jewels, the way people moved, spoke and played poker all indicated an opulence she had only glimpsed in movies. She felt like an imposter immediately.
The staff spoke to Josh and called him Mr. McAllister with familiarity and respect that put her on high alert. The man she was with was Somebody. She noted not a few querying glances her way, but everyone was too polite to inquire as to what she was doing here.
As he sat at a table and a large stack of chips was placed in front of him and he ordered them both drinks and began to play.
Riley couldn’t follow the game at first, she couldn’t keep her eyes off the beautiful women standing behind many of the male players, and their jewels dripped of them and glinted blindingly. The perfumes she smelled were far richer and more subtle than any she had smelled before, and when her cocktail came it tasted better than any she’d ever tasted in her life.
After fifteen minutes of gaping around her like a bumpkin Riley began to pay more attention to the game in front of her.
It took her a couple hands to comprehend that Josh was holding his own. He played quietly and confidently, and the other players seemed to respect him.
Conversations, what little there were, came out muted and hushed as the games at the various tables went on and on. Josh kept his cards on the table rarely touching them, taking quick peaks as they were dealt then not touching them again.
When he folded, which happened every few hands, he would turn to Riley and comment on what was happening, whispering in her ear, his warm breath intimate on her skin as she bent over to listen.
More than once she caught the men and women across the table looking down her top as she bent to hear Josh, her low plunging neckline obviously displaying her breasts to popular advantage.
It occurred to Riley then that she might be able to use that to Josh’s advantage.
Riley knew that on the surface society seemed to prefer large breasts as a rule. Movie magazines and reality T.V. rewarded large breasts with a lot of attention, but in her experience over the last ten years of having breasts, (she was a late bloomer, and her blooms were small,) Riley had noticed that almost any breasts partially exposed would attract a lot of attention.
The next time Riley saw things heating up for Josh, his pile of chips was mostly in the middle of the table, she shrugged her shoulders forward and pressed her arms together under her breasts to plump them up and out as best she could and she leaned over to ask Josh a question.
“Do you want another drink?” She whispered it in his ear, getting very close to him and bending far over to show as much of her breasts as she could. Josh barely looked her way, his focus on the game, and said “No, thank you.” His drink was almost full.
Riley leaned an arm on the back of his chair as if considering what he had just said and she allowed her breasts to do their work.
The neck line of her dress plunged below the bottom of her breasts in a deep V, and by bending over and shrugging her shoulders forward she could let her boobs hang unfettered by cloth. From straight in front her breasts would swell into small round mounds that threatened to spill out of her top, from the sides anyone low enough, say sitting at the table… they would have a good chance at seeing nipple as her tiny buds hung free of her dress.
Riley had always been a bit of an exhibitionist. By developing late she had appreciated the changes in her body more than other girls who grew large breasts early. Riley had been thrilled to grow any boobs by the time she did at sixteen, and having A cups meant she never wore a bra unless she absolutely had to.
All through her late teens and early adulthood she had taken most opportunities to show them off. She was proud of the perfect little mounds she had grown. She had the same sort of perfectly circular tits that so many models had. Her small firm nipples centered prettily and the meat of her flesh aesthetically positioned on her chest. She knew they were great, small though they were.
Tonight proved her point once more. As she slouched over Josh she could sense eyes wandering over her skin. She grew flushed as she saw the glint of eyes twitching from cards and looking for tells from opponents to glance at her exposed flesh.
Feeling naughty and salacious Riley shifted ever-so-slightly this way and that adjusting her position to display her body for the other players. She did this for the next few hands and saw that Josh won three out of four of the successive pots.
The pile in front of him grew bigger and Riley enjoyed her own game of peek-a-boo, challenging herself not to get caught, but to distract as subtly as she could.
Using her experiences as a model to display her body this way and that, revealing her charms while appearing to be interested in the game, she boldly flashed her breasts, legs and her back as much as she dared without being too overt.
After a time the other players polarized.
Some grew numb to her tease and were able to focus on the game, but half of the players, including one woman became so distracted by her that they began to lose rapidly and expensively.
Riley could tell it were her breasts doing the majority of the work. The poker hands she focused on exposing her tits during were the hands that Josh won most often. It was thrilling her to be such a big part of his winning, and as he spoke to her from his chair, filling her in on the proceedings quietly, or flirting with her subtly she felt like an old partner in crime to him.
They were a great team, and he didn’t even know it.
As the drinks flowed and her confidence grew Riley began to have even more fun in this foreign world of wealth. Josh clearly liked her, even as distracted as he was by playing high stakes poker he still had time and focus enough to flirt with her and make her feel pretty and desirable.
Riley didn’t need any man to tell her she was special, but it was nice none-the-less to know she was attractive and interesting to such a compelling man. More than once she had been able to make him laugh a genuine, surprised sounding laugh, and it excited her almost as much as showing her breasts to the others.
She had no idea how much time had passed in that back room, but she was getting ready to leave, to maybe take this man home and spend the night with him when things at the table grew suddenly more intense.
The major players had been whittled down to three big spenders, and Josh had a huge pile of chips in front of him after many hands and much flashing of skin on Riley’s part.
The current hand was really heating up. It seemed that all three players had good hands; the chips in the middle were a bigger pile than Riley had yet seen and people were gathering to watch the game. No-one was watching the pretty girl behind one of the big players; all eyes were following the play.
The bets kept climbing and Riley felt dizzy when she realized the pots were climbing into the hundreds of thousands of dollars.
The player to Josh’s right debated long and hard over the last raise, which had been ten thousand dollars. The crowd around the table held their breath as the player considered his move.
After a small age, and quick check of his cards the guy folded, to the shock of the watchers. It was now down to Josh and one other.
Taking his time assessing the other player Josh looked him up and down. The other man in turn went still and tried to give Josh nothing to read in his demeanor telling what his hand might be.
“One moment please.” Josh said to the dealer and he turned to Riley and made eye contact. She bent over, displaying her chest once more, but this time with little aim to flash the last man at the table.
Whispering into her ear, hidden behind the curtain of her golden hair Josh said, “I thank you for your efforts this evening. Your distractions have been very helpful. I would like to reward you if you will let me.”
Riley was surprised on two levels; first that Josh had noticed what she had been up to, second that he could disengage so fully from the game at this moment to speak to her like this. He had never done that in any other hand that carried so much weight.
Going along with it Riley asked “How so?”
“If I win this hand I will give you the entire pot, which you helped earn, if you will spend the night with me and let me do anything I want to you.”
Riley was stunned.
It was such a provocative offer, like something out of movie, and the amount of money in the middle of the table was huge. She would have spent the night him anyway, he was sexy, interesting and she was very aroused from all her flashing, but the added incentive of all that money had her breathless.
But she was an independent woman not prone to having her head turned so easily.
“What if you lose?” she asked coyly.
The crowd were murmuring among themselves curiously about what on earth they could be talking about at such a time. She ignored them looking into Josh’s eyes instead, daring him to come up with a suitable answer.
“I will pay your hotel bill, and not bother you again the rest of your stay.”
Riley’s room was paid already, but if he would reimburse her for the five hundred her stay had cost that would be fine with her. But she wanted him to bother her again. She wanted that very much.
“In that case you’d better win.” She looked into his eyes and then planted a long lingering kiss on his lips in front the dozens of onlookers. When Riley stood back up she could feel a blush spreading down over her cheeks and across her chest.
Riley suddenly felt more aroused than she ever had in her life. Her body was on the line as a prize and it had her squirming with sexual energy.
All eyes were on the two of them as Josh returned to the game and Riley glowed with a powerful sexual dynamism. Between her legs she felt a slithering awakening of sexual need. She wanted this game over and to be in bed with this man.
Without looking at his cards Josh pushed all his chips into the middle of the table making the watching crowd gasp. There were thousands of dollars in chips there, and now the pot in the middle was huge. All those colourful chips made Riley even wetter. She rubbed her thighs together and stared at the pile as if it were her own naked body on display before this crowd.
Unaware that she was doing it Riley’s hands began to roam her body, lightly touching her here and there as she gazed at chips representing hundreds of thousands of dollars. She gently rubbed a finger along her neck, and down between her breasts aching to touch her pulsating nipples. One hand stroked her belly down low imagining being filled with Josh, his cock stuffed inside her hungry core.
The raw sexuality of her display, her near orgasmic reaction to Josh’s play captured more than one eye around the table, and the sexual tension in the small space around the packed table grew thick and heavy.
The dealer was counting the chips when Josh’s final opponent pushed all his chips into the centre of the table too. Another gasp went around the room and more people arrived to watch this hand.
Riley felt a tiny tremor between her legs and knew that she had just experienced a tiny orgasm just from knowing that she was one more of those chips on the table. Still subtly rubbing her thighs together she prolonged the pleasure and tried to control her panting.
Riley wanted everyone to know that she was being wagered tonight. She wanted her body to be spread out on that table for all to see as these men competed. She wished that she were the prize for both men, the winner taking her there on the table in front of everyone.
As her body clenched tight in a spasm of pleasure Riley gripped one hand on Josh’s shoulder as the cards were flipped and revealed.
The cards on the table in order were: the nine of hearts, the seven of spades, the six of spades, the jack of clubs, and the nine of spades. It appeared that the two nines were the best chance to win and when that other player flipped the other two nines the crowd gasped, sure that he had it with four of a kind.
But Josh had already flipped his cards too, and once the dealer called the winner all eyes shifted to see Josh had the eight and ten of spades. He had a straight flush, one of the best hands in the game. The crowd applauded him and the conversations immediately grew loud and raucous as the viewers determined how well the two players had done in that hand.
However Riley only had thoughts of the sex she was about to have. She belonged to Josh for the night, to do… how had he said it? Anything he wanted to? The vagueness, the implications of something lewd and nasty had her once more on the cusp of climax.
“What is wrong with me?” she wondered to herself. “Why am I so turned on by being a prize?”
But she knew why? She had been a competitor all her life, and she was thrilled to be thought of as a prize worth so much money.
Even before the dealer had pushed Josh’s chips over to his side of the table Riley squirmed onto Josh’s lap and began to kiss him passionately. She clutched his face and pressed her mouth to his and slipped her tongue into his mouth to caress his own tongue.
His hands lifted to her sides, cupping her just under her breasts and holding her still as they kissed greedily in front of the gossiping crowd.
Then Josh broke away abruptly and lifted her gently from his lap. People immediately swept in and began to pat Josh on the back and shake his hand while Riley tried to collect herself. She felt faint with desire after that kiss.
For the next few minutes the winnings were collected by a hotel staff member, Josh was surrounded by well-wishers and Riley was able to go lean against a wall and collect herself. She couldn’t believe what was going on in her body, and what was about to happen to it. It took an act of will power to keep her hands off of her breasts or from between her legs. Her body was flushed and desperate for attention.
She was so caught up in the sordidness of the exchange that it took her long moments to realize that all that money on the table was now hers.
She was now rich.
If Josh would uphold his end of the bargain.
Suddenly Riley felt cooled. She needed to start thinking a bit more clearly. This was the kind of money that people did stupid, dangerous things over. She would have to actually work out an exchange with him, not just fuck him and hope for the best.
Josh looked for her and saw where she was. She smiled at him and he looked relieved to see her. He pointed to the door and she made her way through the throng and met him with a security guard and a cashier who had the chips.
The small parade of them made their way to the cashier’s cage and started the process of exchanging the chips for money.
Chapter Two: Dinner
At the cashier window Josh asked for a cheque and then turned to Riley and asked how she wanted the cheque made out.
She didn’t need a plan to get the money, but she would still need to negotiate a few details about the night.
“We should set some ground rules about tonight.” She said, but she said it gently, while touching his arm and letting him know she was still interested.
“The rules are… anything I want to do to you. The price…?” He asked the cashier, “How much is the total?”
“The payout is $374,650, sir.”
Josh turned to see her grow pale as she heard. “I think that earns me the right to let my imagination run wild.”
Riley couldn’t comprehend the number, but she could read Josh’s face. He seemed pleased, and indulgent but not angry or cruel. Maybe she could do this with no rules, no protections. She had more money than she could earn in ten years of work waiting to have her full name written on it.
Nodding sharply Riley adopted a mock serious business demeanor. “Alright sir, I believe that brings our negotiations to a close.” Then she smiled, her excitement brimming over.
Riley spelled her name for the cashier and took Josh’s hand in hers and while the cheque was printed she slipped Josh’s hand up under her low hem and placed his warm fingers in her underwear.
Josh cocked his head at her, as if to ask “Are you sure?” even as his fingers began to explore her slippery sex. His eyes widened as he discovered that she was soaking wet, her pussy leaking pleasure over him.
In preparation for lying out by the pool in the tiniest bikini she dared wear, Riley had waxed her pubic hair off two days ago. Her soft, bare skin was slick with her juices as Josh fingered her in public.
Riley leaned in and began to kiss him desperately as his fingers found her burning clit and she had to cover her gasp and shudder as yet another climax threatened to explode between her legs. Clinging to his shoulders, her arms around his neck, Riley held on as she fought the need to cum as Josh stoked her tender button in view of dozens of people.
Before it got too bad, and she either broke away violently to avoid embarrassment, or what she wanted to do more, obviously orgasm in a very public place, the cashier interrupted and passed her cheque through the window.
Josh stopped what he was doing and using the same hand, now glistening with her juices, and picked up the cheque and ostentatiously handed it to her. Cameras clicked as she reached for the paper and grinning people pressed in to see.
Josh held on tightly when Riley tried to pull the cheque from him and he smiled wickedly and clutched it so that she had to tug on it. He said loud enough for anyone to hear. “Anything I want to do.”
Riley blushed deeply, but refusing to be cowed she replied. “For one night only.”
Josh let go of the cheque and whispers spread out around them like a pool of water, rippling out farther and farther away with every passing moment.
By the time Riley had the cheque folded and placed inside her tiny clutch purse the whole casino seemed to know that she had made some sort of deal with the guy who had won a huge poker game. Everywhere she looked she could see speculating faces wondering if she were a hooker or call girl or something.
Feeling more desirable than she ever had in her life Riley took Josh’s arm and asked, “Where to?”
“Let’s go eat.”
A small crowd followed them as they moved to a dining room. Josh requested a seat that overlooked the casino floor, thus exposing the two of them to the full view of the room and all the curious onlookers.
Gossiping gawkers watched them as they ordered drinks and sipped them while trying to ignore the crowd. Riley was getting uncomfortable with all the eyes on her. Josh seemed quite at home, and he ordered a big steak and salad to eat.
Riley had little appetite but she ordered a shrimp dish and hoped to be able to nibble when it came.
Before it did however Josh began to collect his debt.
When they had sat he told her to sit facing the casino floor while he sat beside her to her right. Sitting up straight in the low, comfortable chair he said, “You flashed those gorgeous tits of yours for everyone else, time for me to see what I’ve been missing.”
Riley gaped at Josh. Was he telling her to bare her breasts here in full view of the whole casino? Could she do it? Was this enough money?
Josh didn’t give her time to decide. He reached over and slid his fingers just under the edge of her dress, right where it plunged below her breasts. He wasn’t cupping her breast, just lightly brushing it. Looking her in the eye he smiled. “Anything I want to do to you. Or we could bet each other.”
His fingers moved up and down along the edge of her dress, the back of his fingers stroking the swell of her right breast, his warm hand stroking feather light along her highly-sensitized skin.
“What do you mean?”
“I mean another wager. Not that I am not completely pleased with the way things are right now, but…” His hand cupped her entire breast and voices whispered all around them while cameras flashed capturing her debauchery as she let a man fondle her in public. “I offer you a dare. If you take your top down now and eat with me with both breasts fully exposed I will pay you $50,000 on top of your other winnings. If you won’t do it, then you pay me back $50,000. What do you think?”
The thrill Riley was getting from having his hand massaging her sensitive mound while people snapped pictures and whispered judgmentally had her so aroused that she could feel her panties growing damp from her leaking fluids. This was the most outrageous experience of her life and she loved it.
Remembering all the times she had stretched out on her back in her back yard, knowing somewhere above her in one of the many buildings that looked over her yard that prying eyes witnessing her exposure, Riley thought that Josh had no idea who he was dealing with. Sure Riley was somewhat shy, and certainly not sleazy, but this situation had her more aroused than anything in her life had before. She was totally up for the challenge.
“Lets’ see the money.” She said with a wicked grin.
Taking his hand from her breast Josh lifted it and waved over a server.
“Would you please call a casino manager over for me?”
“At once Mr. McAllister.”
“Who are you?” Riley asked pointedly.
“Clearly no-one you’ve ever heard of, so not important.” He smiled to take the sting out of his words and took a sip from his drink.
In moments a man walked over and asked how he might be of assistance.
“Would you please bring me a blank marker made up for $50,000? The lady and I are placing a wager with each other.”
“Right away sir.” And the man left.
“What was that?” she asked unclear how this worked.
“When you reach a certain status with these hotels the understanding is that gamblers will gamble on anything. The hotels acts as the holder of the mark. For a five percent fee they will hold any marker for any amount that the person in question can be considered capable of paying. It is like a bank issuing cheques. They will take the terms of the bet and uphold the rules for us.”
Riley was surprised and intrigued at the efficiency of the whole thing. In moments, long enough for the crowd around the floor outside their restaurant to double in size, the manager returned with a mark printed out for the amount of $50,000.
“Thank you. Now the terms of the wager are that my lovely companion will dine with me and have both her breasts exposed for the entire time. If so she wins the money, if she refuses, or stops before the end of the meal she owes me the money. Agreed?” He held out a hand for Riley to shake.
She couldn’t see any loopholes that would force her to fail, but just to be careful, she added. “But if I am interfered with, or forced to stop by a third party then the bet is void.” She awaited his response.
He considered for a moment, and then agreed. They shook hands and the crowd murmured curiously knowing a wager had just been agreed to.
Before she could balk or reconsider Riley reached up and pulled the straps of her dress down over her shoulders and lifted her arms free exposing her whole chest to the onlookers. Cameras flashed and voices called out encouragement and cat calls.
A loud buzz began and the whole restaurant began to crane their necks to see her. The manager with the marker stood to the side out of the way, and a server brought their meals hesitating for a beat when she saw Riley’s exposed breasts.
Riley couldn’t even begin to eat; her mouth was dry and her throat tight with mortification. What was she thinking? Her bared bosom was being recorded by every conceivable device and probably put on the internet, sent to friends of the observers, sent to T.V. and newspapers and recorded on the security cameras and who knew what else. Her privacy was so fully violated that her life from before was being eroded before her eyes.
And she loved it. Her nipples stood tall and proud, long points of hard pink flesh thrilled to be seen, her small coral colored areola matched the bright pink of her blush covered chest. Feeling hot and sweaty under the gaze of dozens of eyes Riley pretended to nibble her food and took great gulps of her drink.
The meal seemed to go on forever. Josh took his time savoring his perfectly cooked steak and the view of Riley’s perfect breasts. Her chest was lightly tanned usually, although stained pink with her blush at the moment. The top of her exposed stomach showed the sculpted abs she worked so hard on. But for now all eyes were on the smooth circular orbs of her bosom sitting daintily on her narrow torso.
Riley managed to eat a little bit while Josh consumed his full meal. The crowd around the restaurant had grown so large that security had come by to force them away from the nearby slot machines so people could keep playing.
No-one told her to pull her dress back up.
By the meals end she was more comfortable, and had even begun to pose slightly, showing off as best she could while sitting. Her slit was still wet, but no longer leaking with need.
Josh put his knife and fork down and asked if she was finished eating. She nodded yes and as a server approached to remove the plates Josh held his hand out for the marker and a pen. He signed over the $50,000 unperturbed and gave Riley the marker.
“You won.” He shook her hand and applause rang out over the assembled by-standers. Riley smiled and blew some kissed to the cameras and, still exposed, put the marker into her purse.
Only then did she pull her dress up and once more cover her chest.
“Shall we move on to our next stop?” Josh asked.
Chapter Three: The Dance
Riley was slightly put out, she had hoped, even expected, that they would adjourn to his hotel room or someplace private and have sex. It seemed he had other ideas when he asked for another marker from the hotel. One for $100,000.
What was he up to now?
$100,000 dollars? She had over $400,000 in her purse at that moment, what could he offer to entice her to risk any of it? The thought had her nervous, and titillated.
When everything was settled up at the restaurant Josh took Riley’s arm and the two of them, two body guards that had been hovering close enough that she now realized they were with Josh, and a few curious by-standers all paraded through the casino and out onto the strip.
A short walk along the strip and some flirty conversation with Josh and Riley was once more calm and charmed to be with such a fun, confident man. Josh was amusing, intelligent and seemed genuinely interested in Riley without prying. He drew conversation out of her as easily as one of her girlfriends, only the conversation was more about what fun things she had done in her life, or would do with her money.
Josh effortlessly herded their small group and the hangers-on over to a club, and through the doors into the largest strip club Riley had ever seen, or heard of.
The place was massive, utterly massive and filled top to bottom with gorgeous women with almost no clothing on. Riley suspected that there were hundreds of dancers either performing on stages, small platforms, on cages or on many, many laps.
Seeing so many naked women surrounded by so many clothed men was confusing to the eye. As Riley was swept along with Josh and his men she couldn’t help staring at the amazing variety of female forms on display.
Never before had Riley seen such an array of gorgeous breasts. Each pair was unique, appealing and on display. Small ones, big ones, white ones, brown ones, large nipples, small nipples, and every measure between.
The asses, the legs, the faces, the bellies; Riley felt surrounded by soft female flesh, and it all looked wonderful. Riley wasn’t gay, but she enjoyed a drunken make-out with a woman as much as the next gal and these ladies were appealing.
With her head swiveling on her neck she was suddenly stopped short when she ran into Josh as he stopped. He began talking to a man in a suit who looked official, only because he wasn’t drunk, or ogling anyone.
As the two men spoke Riley watched a dancer close by. The sexuality of this woman was unbelievable. She was undulating on a small stage with a pole in the middle and she was putting on a show for twenty or so men seated at tables near-by.
The young woman was a light-skinned black woman. The dance was provocative, raw and compelling. She undulated her hips in an open invitation to imagine her having sex with someone. Her face was a passionate mask of pleasure, her body lean, lithe and so supple her bones seemed fluid.
Riley was mesmerized by her.
After a few moments Josh turned to Riley. He looked to where she was looking and smiled.
“Do you like the way she dances?” He asked.
“I do. She is amazing.”
“Do you think you could do that?”
“Oh, I don’t think so.” She laughed, then looked at his face, and saw the wicked, amused glint in his eye.
“Could you do it for $100,000?”
The penny dropped. This was the next wager. Even as her mouth began to form the word ‘No.’ she felt her body respond with arousal. Riley looked back at the sexually charged dance the black woman was doing and felt her body’s desire to be doing that in front of all these men.
“What is the full wager?” she asked instead of saying no outright.
“You dance, on the main stage over there and do a full strip, down to your panties, and if you can earn a hundred bucks in tips from the crowd you win the hundred thousand.”
“Wait. Where is the challenge for you?”
“What do you mean?”
“I say you should have to be part of the challenge too. I did all the work last time. I want you to sit in a chair on stage. I’ll strip and do a lap dance for you, and if you can keep yourself from getting an erection for my whole dance then you only have to pay me half for the dance. But if you get hard I get it all. And I get half an hour to pick up a few pointers from these ladies.”
“Okay, I like that deal.” He was smiling like a schoolboy, and Riley suddenly had the fear that he couldn’t get an erection.
“Hold on. I need to prove something first. Look over there and watch her.” Riley pointed to the black woman and as Josh watched the woman dance Riley boldly reached down and began to stroke Josh’s penis through his pants. He flinched for a moment but then laughed when he realized she was proving his ability to get an erection.
Riley was shocking herself over and over tonight. Feeling as if she were another woman she masturbated a near stranger in a public place while they ogled a stripper. But she was beyond caring, this was competition and $100,000 was on the line.
Riley was studying the woman carefully as she moved, and as Riley did so she was pleased to feel Josh’s penis grow much larger and harder under her hand. Rubbing him up and down his length through his pants she felt him get substantially bigger, and she grew increasingly wet.
When Riley was starting to wish they could just leave and fuck each other already she felt Josh take her wrist and stop her. “I think I have proven I can fulfill my end of the bargain. You have 25 minutes to prepare for the dance.” And then Josh walked away, a big Maori looking man stayed with him, and a slighter, but taller black man stayed with Riley.
Wandering the floor Riley observed the ladies dancing, and she got herself a drink, and the half hour went by far faster than she would have believed.
“Excuse me miss, but the time is up.” The bodyguard gestured her toward the stage. Suddenly Riley was very nervous. She had never done anything like this outside the safety of her bedroom. She hadn’t taken any time to think about how to get out of her dress while looking sexy, she hadn’t considered the hundreds of people that would be watching her try and get Josh hard. And she hadn’t thought about what this said about her as a woman.
She had simply been trying to take in beautiful women dancers and absorb what they were doing into her own body. The task suddenly seemed impossible.
The bodyguard took Riley backstage behind a curtain and a female stage manager came over and looked at her.
She nodded yes.
“Okay, you’re on next. You need anything?”
“Is there a chair for my friend?”
“Yeah, he is out there, and we will be getting him onstage while they announce you. Anything else?”
Riley looked around at a loss. Then her eye landed on a few random objects heaped near the wall, feather boas, bras and hats, the detritus of earlier performances. “Can I look through there?”
“Yeah go ahead, you have thirty seconds.”
Riley’s belly clenched in terror at the short time span, but her competitive brain overrode her fear and she began to rummage through the mass of cast off clothes. She found a fedora she liked and a blazer, and she quickly put them on. She glanced in a mirror to the side of the stage entrance and adjusted the hat over her hair artfully. The shrugged the blazer over her shoulders. It was a bit small, but would do for now.
A voice on the sound system suddenly boomed out over all the music and conversation.
“Ladies and gentlemen I would ask you to direct you gaze to the main stage at this time. We have a special performance tonight. A new dancer to our stage, the lovely Riley will be taking it off for your viewing pleasure. Please give it up for Riiiiileeeeeyyyy!!!”
Some trashy techno beat slammed out of the speakers and the lights on the stage went on. Riley hesitated for a split second and then her natural competitive nature and exhibitionist factor propelled her out into the light.
Riley had always loved dancing, she had even taken a dance class in college just for fun, she was a high calibre athlete and a born show off. The second she hit the stage she struck a pose, her left hand went up to the hat, her right arm out to the side like Elvis, and her knees bent her head turned. She was channeling Michael Jackson, Elvis and every rock star she had ever loved from Lady Gaga to Gwen Stefani, Britney Spears and the Spice Girls.
The driving electronic beat pumped and Riley strutted the stage showing off to everyone watching. She walked all around the stage, claiming the space, finding out how much room she had. All the way down a long runway she came across Josh sitting comfortably in a big leather chair with no arms.
She trailed her hand across his face, mussing his hair as she passed, barely acknowledging him as she sashayed by. She had more important things to do. She needed to win over the men watching her.
Strutting the length of the stage, her stomach in knots Riley made eye contact with the men sitting along the edge of the stage letting them get a good look at her long legs in her short dress.
Then after a full circuit of the stage she stopped at the very back, at a place where everyone could see her and she faced away from the crowd and pulled her dress up toward her buttocks, threatening to show them her ass.
Peeking over her shoulder to watch the crowd she waited until she had everyone’s attention on the appearing globes of her ass, then she twirled a full circle and with a lewd hip thrust let her dress fall back down as she humped her pelvis toward the observers.
Now she did a sassy bump and grind the entire length of the stage, strutting and humping while dancing her way toward the far end where Josh sat.
Over and over she lifted the hem of her skirt and played peek-a-boo with her bum and pussy. Her little black panties barely covered her ass, and cupped her bald sex tightly so she was giving quite a show.
When she got back to Josh she twirled and sat on his lap while pulling her dress up over her hips. She plopped her practically bare ass on his thigh and ground her buttocks along his legs provocatively.
Before she could settle long she stood once more and did her bump and grind back to the middle of the runway. Then she faced the back once more and began to open and close the jacket, flashing her shoulders to the men behind her.
She was beginning to get some cheers and she enjoyed knowing she was starting to win them over.
Taking the jacket off of one shoulder she slowly seductively revealed her bare arm. Turning sideways so everyone had a view she bared her left arm and made it seem as if she were exposing something far more intimate. Then she did the same on the other side, holding the jacket to cover her chest.
When she had the jacket off she used it like a bullfighter’s cape and played peek-a-boo once more. Slipping out from behind it, she flashed her body, still hidden in her dress, but pretending she was showing far more.
When she heard a crescendo growing in the music she timed her movement to it and when a crash happened in the song she threw the jacket away standing in her revealing dress before the crowd.
She started seeing money being held up to her and she danced over to the men holding dollar bills up and as she had seen other girls do she bent down so that they could put the money in her top, their hands brushing her breasts as best they could while stuffing her top with bills.
That seemed to be a signal to dance for them so Riley began to pull the straps of her dress down for this clump of money waving men.
She didn’t know how much time she had left so she pulled off her dress straps right away, holding her top over her breasts as well as she could while trying to look seductive.
More money appeared so she must have been doing it right.
Now she went back to Josh and turning her back to him she offered him her zipper to undo. While he pulled the zipper down the back of her dress she wiggled her ass back and forth before him, clutching her top to her breasts and smiling at the men upstage from her.
When her zipper was all the way down she walked away and went far upstage. There she danced as much like the black woman as she could and let her dress slip down over her body. Keeping one of her hands over her boobs at all times she slithered out of her dress to loud cheers.
Stepping out of it was the hardest part, but she used her strong core strength to hold still in her high heels, she lifted one leg at a time to step out of the dress and stand before the hundreds of men watching dressed in only her tiny thong panties.
Then when the music built up once more she threw her dress to the back of the stage and opened her arms to show the world her body.
Deafening cheers met her nudity and she stood still for a moment basking in their adoration. Riley had a very toned, sculpted physique. She worked out a lot and had a firm stomach with lean, carved muscles. She looked perfectly feminine, but she looked like a swimsuit or a fitness model.
Her smooth skin had no tan lines to speak of and looked creamy and soft in the sultry stage lights. There were many other women prettier than she here tonight, but she had a special quality none of the other had: a girl-next-door innocence that any amount of living in Vegas seemed to rob other girls of.
The men loved her and cheered loudly.
Still wearing the hat, her heels, tiny panties and nothing else Riley now focused her attention on Josh. Walking through a litter of paper money she strutted back to him and gave everyone a show. Riley paused now and then to rub her body, squeezing her breasts like the other girls did, or running a hand along her sex as if she couldn’t stop herself she was so horny.
When she got to Josh she walked all around him running her hands over his shoulders and chest admiringly. She pressed her small soft boobs onto his head and rubbed her hard nipples on his scalp arousing herself even more.
Her fear was almost gone and she focused on getting him as horny as she was.
Facing him now she lifted one leg onto the back of his chair and leaned forward shoving her pussy almost onto his chin. She did a grinding undulating dance like that for a bit, stroking her breasts and rubbing her ass for those behind her.
Then she let the raised lag slip further past Josh and she went into the splits one leg pointing straight out past Josh’s head and one pointed straight out behind her. Her crotch was now planted on his chest, her belly in front of his face and she bounced a bit here showing everyone how flexible she was.
Lifting herself from that awkward position she turned and sat on him once more grinding her ass all over his groin, stroking his cock for all she was worth. She could feel that his cock was still soft, and she was pleased that she would have to try harder. Her soaking wet pussy wanted her to show off some more.
Now she faced him and bent over putting her tits in his face. She rubbed them both aggressively, stimulating her nipples, pulling on them and pinching them and squeezing her soft orbs lecherously.
Then placing her hands on his chest she lowered her face all along his body stroking him from chest to cock with her cheek. When her face was buried in his groin she lifted her ass high and spread her legs for the other men viewing this display.
With both hands on her ass, prying open her cheeks she offered her barely concealed holes to the men behind her while rubbing her face all over Josh’s cock like a cat looking for some scratches.
She felt his boner grow along her face and smiled knowing she had him now.
Standing and turning she stood before him one hand still playing between her buttocks, stroking her firm cheeks, the muscles rounded and sculpted from years of jumping in volley-ball. She let those fingers caress her globes for Josh, while she played with her breasts for the other men.
Riley was horny. She had never been so wet, so ready for sex as she was at this moment. If she didn’t think she would be arrested she would have pulled out Josh’s cock and sat on it right there in front of everyone, she was so inflamed.
Abruptly the song ended and the big voice asked everyone to “Give it up for Riiilleeey!”
Cheers erupted around her and Josh grinned at her from his chair. “I’d say you won.”
By way of reply Riley leaned over and kissed Josh deeply, her tongue driving into his mouth and claiming his own to wrestle with. With the stage lights still on and hundreds of men clapping for her Riley bent over, practically nude and passionately made out with Josh in his chair.
When the lights came down, and the crowd booed, Josh stood and took her hand leading her backstage where her dress had been swept up along with her tips from the men in the front row.
She earned $200 in tips and $100,000 from her wager.
“Josh, I am having the time of my life tonight, but if you don’t take me someplace and fuck me I am going to go nuts. And I won’t be responsible for my actions after that.”
Grinning at the gorgeous naked woman demanding sex from him Josh held out her dress and said, “I think that sounds like a wonderful idea.”
Turning to his hovering body guards Josh told one man to get the car and meet them around front.
Riley dressed, feeling like she would rather take everything off, and when she finished Josh took her arm and lead her from the club.
After they got into the classiest car she had ever ridden in, some kind of high end Mercedes, the two bodyguards in the front seat and she and Josh ensconced in the back, Riley finally had a moment to understand what she had just done in front of hundreds of people.
“Oh my God! That was amazing!” She hurled herself at Josh and began to make-out with him again. At first it was manic, uncontrolled lust. She couldn’t focus on any one thing; kissing him, rubbing his arms or shoulders, letting him kiss her neck, it was all a blur.
Then after a frantic few moments Riley calmed down enough to simply let Josh kiss her neck and upper chest, her body thrumming with warmth, open to indulgence.
“Anything I want to do.” He murmured into her ear as he nuzzled her nape.
“Anything.” She replied.
“Julian. Open the sun roof please.” Not what she expected Riley pulled back to look at Josh. She found herself momentarily confused, wondering why she had stopped caring that two other men were in the car with her while she made-out with Josh, but when the warm desert wind blew into car she began to wonder more about why Josh wanted the sunroof open.
“I want you to stand up on the seat with your head out the sunroof facing the rear of the car. Stay there until I tell you to come back down, okay?” He asked politely enough, but there was demand in his tone too, and that thrilled Riley on a deep level.
Smiling her confusing she stood daintily on the leather upholstery and poked her upper body out of the sunroof. The warm wind blew her hair every which way and the screaming wind deafened her. The bright lights of the Las Vegas strip rolled by dazzling her.
This was the best night of her life.
Then she felt Josh lift her dress and pull down her panties.
“Oh God.” She thought. “He is looking right at my pussy!”
Josh rolled her panties all the way down and lifted her legs one at a time to pull them off her feet. Then she felt him begin to play with her swollen lips, parting her slippery folds with his fingers as he began to explore her sex.
So many sensations flooded Riley she could hardly keep up. Her body was overjoyed to finally be fondled so intimately. She had to force herself to hold still she wanted to squirm with pleasure so badly.
Yet at the same time she had the nervous insecurity of a first time with a new lover. That always shook her up. She also felt a wash of humiliation knowing she was being exposed to the other two men in the car, should they care to look back.
And the added sordidness of being a prize with no volition of her won had her trembling with passion. Josh owned her for the night, as per their agreement. He could do anything he wanted to do. That made her feel both vulnerable and lascivious.
Then Josh’s mouth on her pussy eclipsed all of that. Now she was just a woman who wanted to cum very badly.
With both hands she tried to hold her whipping golden hair from her face while bracing against the stopping and starting of the car in the heavy evening traffic of the strip.
While Josh devoured her slit, licking her intimately, yet avoiding her clit, Riley gasped and shuddered delightedly and watched the people on the sidewalks watching her.
Above the roof Riley stood as calmly as she could, nodding and smiling at passer-byes, trying to keep her balance while below the roof her cunt was ravished thoroughly by an expert in cunnilingus. Riley had never had a man eat her so well. Josh seemed to know everything about her pussy, things she had never known she liked, such as having her delicate inner lips sucked on and lightly nibbled. Her orgasm approached far faster than ever before.
Then at last Josh sucked her clitoris into his mouth and flicked his tongue over that achingly sensitive bundle of nerves. Riley cried out her passion as her climax surged out from her cunt and enveloped her whole body.
The car pulled to a stop at some lights while Riley writhed helplessly on top of Josh’s ceaselessly wriggling tongue.
Juddering as she tried to control herself Riley looked into the next car. An older couple were watching her with small smiles, thinking perhaps that she was drunk and enjoying the night air. Riley whimpered audibly, her mouth gaping open, her eyes bugging out as another powerful wave of delight washed out over her from her burning clit.
Her fingers clawed feebly at the polished roof of the car while Josh lashed her mercilessly with his nimble tongue. The old couple stared now, confusion growing on their features as Riley’s face contorted lewdly as multiple waves of ecstasy ravished her body with delight.
Turning away from the couple, feeling vulnerable, Riley looked to her left toward the sidewalk. Even as her body shuddered ecstatically, her breathing tight and laborious Riley turned and saw a small group of fifteen or so people standing at the corner waiting for the light to change.
Each and every one of those people was staring at her as she twitched and strained to contain all the explosive delight her body was experiencing. Riley accidentally made eye contact with a middle aged woman with a big flowery dress on even as Josh’s tongue delved into her inner most ring of muscle.
As his tongue impelled her to cum harder and harder she bit her lip to stop from screaming, or to hold back the pleading for mercy she wanted to do. Josh’s strong hands held her buttocks tight, pressing her quivering hips to his wicked mouth as he tortured her with his agile tongue.
Unable to hold herself still Riley bucked her hips seeking escape, and/or more scalding pleasure from that cruel tongue. Whimpering audible, Riley knew she was making a spectacle of herself. People were nudging each other and pointing.
Then it got worse.
Josh slid his fingers inside her pussy and began to fuck her aching, ravenous cunt. Instantly, what Riley had thought of as delightful torment a moment before, expanded and multiplied into depraved euphoria.
The fabulous, fulfilling prodding of his fingers exploring the cock-starved depths of her pussy sent her body into a convulsion of orgasmic delight. The scream she had been holding back oozed out of her throat in a long, low groan. A part of her consciousness knew that she was putting on a sordid display for the near-by pedestrians, but she couldn’t concern herself with that when her body was engulfed in waves of such pleasure that she could hardly stand upright.
Josh still had his tongue slipping around her clit and as his fingers drove into her aching, clenching core she wailed a song of euphoria to the Heavens that was being filmed from the sidewalk by many phones. Once more her most private feelings and intimate moments were being captured by strangers and Riley found it all so intensely arousing that her climax lasted far longer than usual.
The light changed and cars, like the older couple next to her, drove away, but Josh’s car remained at the light, the car behind her honking as Riley’s orgasm went on and on.
Soon his tongue on her clit became too intense and almost painful, the tingling burn in her tender button far more intense than she liked, but his fingers pressing against her g-spot wouldn’t release her from the exquisite torment of her climax.
Riley tried to hide behind the fall of her hair, her mortification eclipsing her pleasure at being seen. This orgasm was too powerful, to all-consuming for her to take delight in showing it to anyone. She felt utterly exposed and humiliatingly displayed in this intimate moment of bliss.
She clamped down on her pleasure and swallowed the fulfillment she was feeling from Josh’s fingers and tongue after a night of growing sexual incitement. All through this evening she had been getting more and more aroused and now that she could finally climax it was happening in public, and people couldn’t even tell why she was cumming so hard. It simply wasn’t fair and Riley wanted it to end. She wanted Josh to take her someplace and fuck her properly.
But, the agreement was anything he wanted to do to her. She had the money in her purse. So much money that she had to endure this luscious defilement for as long as he wanted to put her through it.
The car behind them honked once more and Riley was profoundly relieved when Josh’s car pulled away from the filming crowd and drove of down the strip once more.
The second Josh let her go; pulling his fingers from inside her, his mouth from her clit and his hand from her ass she dropped through the sunroof and crumpled on the seat beside him. Sprawled across the seat, her legs akimbo, and her dress still over her waist she attempted to take a deep breath, her lungs seared from lack of air.
Josh used a white handkerchief from his pocket to wipe her copious flow from his mouth, and he grinned at her with a self-satisfied air making her blush and place a hand over her still throbbing sex.
Several times she tried to speak about what had happened, to explain her embarrassment, to beg him not to do that sort of thing again, but lack of air, and a deeper sense of emotional and sexual release made the words dry up in her throat.
The fact was that- as her body came down from the high of multiple-orgasms, and her heart felt free after sharing her pleasure with so many-, Riley was growing aware of just how much of an exhibitionist she actually was.
This last couple of hours had opened in her an unexpected sexuality that she could hardly fathom. Starting with some playful flashing she had progress to wanton behaviors and lewd displays she never would have thought herself capable of.
Even now, in the flush of humiliation and regret over her public exposure, Riley lay with her legs open her sex hidden only by her one hand. She hadn’t pulled down her dress, and she felt a resistance to doing so. Being exposed and having witnesses to her lechery was liberating and fulfilling.
She wanted, and feared wanting more.
Chapter Four: All In
The four of them drove in silence for a time, Riley grateful for the reprieve as she attempted to understand these revelations about herself. What did these behaviors show her about who she was? How could an otherwise decent, well-adjusted individual engage in this level of deviancy?
Even as she replayed the things she had recently done in her mind her fingers began to move, almost of their own accord, and fiddle with her soaking wet pussy lips. She stroked her outer lips and smeared her slippery juices around the swollen, tingling flesh tantalizingly.
There was no denying the powerful sexual charge she got from cumming in public. It had been intense.
The car pulled up under the awning of a tall building just off the strip and Josh pocketed her panties as the two bodyguards got out of the car and opened the back doors for the two passengers.
Riley stood on shaky legs and smoothed her dress over her legs covering her slick sex. Josh came around and took her arm and led her inside. What further degenerate activities awaited her inside this strange building? Riley felt both alarmed and thrilled by the potential.
One of the big men took the car away, and the other accompanied them into the building and into the elevator. As soon as the elevator doors closed Josh spoke. “I’m going to ask you to return the favour I gave you in the car. I’d like you to suck my cock now.”
“Here? But what about…” she looked around the small elevator and glanced significantly at the other man standing right beside Josh.
“What? Oh no, you don’t have to suck Maaka’s cock.” He grinned at the big Maori man. “Not unless you want to after.”
“No. I-, I just…” Riley felt mortified. Her brain was short circuiting from confusion and the fog of desire that she felt. Josh took her hand and placed it on his hard-on and she felt a profound desire to see it, to taste it and have it fill her.
Just having a cock in her hand freed her from her inhibitions. After everything she had done tonight how was this worse? She wanted Josh so badly that having another man watch seemed a small price to pay.
Even as she thought this, even as she negotiated with herself over what she was willing to do, or not do in order to keep the huge sum of money she had been paid to do these things Riley found herself dropping to her knees on the elevator floor and unzipping Josh’s pants to pull out his cock.
A couple times as a younger woman she had tried risky sex. Once in college she had fucked a guy in a bar bathroom, and she had once given a blow-job to a reluctant-but-willing boyfriend on their balcony in broad daylight knowing people could see them from surrounding buildings.
But doing it with a man standing inches away was a far cry beyond those adventures.
Yet as soon as she saw Josh’s beautiful penis, and felt the warm, soft skin she wanted it in her mouth.
Josh’s cock was long and thick, somewhere around seven inches she guessed, and it was a smooth pink tube of meat. His head was big and dark and looked tempting to suck, like a candy she loved.
With a brief glance at Maaka to see if he was watching, Riley saw that he was filming her with a cell phone and she shuddered with an sudden, overwhelming need to be seen servicing Josh. She sighed and licked the bulbous head of Josh’s cock. The feeling of his warm spongy head pushed all thoughts of humiliation from her mind.
Focused on experiencing this new penis Riley explored Josh with her mouth, happy to be tasting him and relishing the feel of his erection.
Every cock was different and Riley enjoyed the feel of the ridges and valleys the veins made on the shaft. Using her lips she spread her saliva all along the length of his shaft and thrilled as the nerves in her mouth awoke to new sensations.
With one hand around his shaft and her mouth adoring every inch of his pole she could reach, Riley lavished Josh with her attention, putting on a show for the camera while glorying in having her mouth so satisfyingly full of delicious manhood.
Riley couldn’t remember ever enjoying sucking cock more, and she had always found it enjoyable. Josh moved here and there slightly, groaning and moaning his delight as she savoured his erection gleefully. The fact that it was being filmed brought a sharp, raunchy quality to the proceedings even greater than the public orgasm she had recently experienced.
The climax on the street had happened to her, she was actively engaged in this event and the fact that she was the one giving pleasure gave her power and agency over her sexuality while at the same time displaying her participation in her own degradation to full effect.
A bell chimed indicating they were approaching whatever floor they were heading toward. Riley didn’t stop sucking on Josh’s cock however. He hadn’t told her to, and she was enjoying it far too much.
The elevator stopped and Josh lifted her head from his spit drizzled erection, her mouth open wide hungry for more.
Taking her hand, but not putting his cock away Josh helped her stand and the three of them exited the elevator, Maaka still filming. With his camera he captured the moment when Riley saw were Josh lived.
Josh’s penthouse suite was astonishing. It was an ultra-modern, open concept apartment. The space was clean and expansive with gorgeous furniture out of the most tasteful magazines. Riley was blown away by how beautiful everything was. Her tastes tended to run toward the homey, comfortable aspects of living, but Josh had cool clean lines to all his decorations. His home looked like a relaxing museum of modernity.
Chrome, sliver, white and a few powerful touches of colour here and there gave the place an austere feel with warmth brimming out from between features. Riley was very impressed.
“Who are you?” she asked him once more, awe in her voice as she looked at what easily had to be a multi-million dollar home.
“I’m Josh McAllister, and I would like very much to fuck you.”
“Well then I suggest you do just that Mr. McAllister.”
Josh came to Riley then and crushed her to him in a tight embrace, his mouth smothering hers and they kissed deeply like long lost lovers, not near strangers.
The two of them groped and wrestled as they kissed and fondled one another. Josh’s hard-on thrust up between them and poked Riley in the belly as she ran her hands all over his back and buttocks. His hands groped her breasts and ass as he licked and suckled her tongue and pressed his lips to hers ceaselessly seeking more stimulation.
Riley felt insatiable. She needed his hands everywhere, his mouth all over her. After hours of teasing, and working her up to a fever pitch she needed this man to take her and fuck the living shit out of her immediately.
Kissing was excellent, and the two of them continued for a few minutes, but Riley was too far gone to take things slow. She dropped to her knees once more and engulfed his cock in her mouth. Riley knelt on the amazing blonde hardwood floor and worked his cock like she needed it to live.
The feel of his erection was so exhilarating she couldn’t focus on pleasing him. She took him deep in her throat, then pulled back and licked the head, and then she ran her mouth along the side of his shaft slipping her lips all over it. Every few seconds she changed how she sucked him, her mouth tingling and needing to feel him every way lips and tongue could feel. She wasn’t even aware that she was making soft moaning sounds in her throat until he pulled her away and she heard herself whimper with disappointment.
Josh knelt down with her and kissed her some more, capturing her mouth and filling it with his tongue. Greedily Riley suckled that instead of his penis. As long as something was filling her mouth she didn’t care.
Then Josh went lower, kissing and licking her neck, then her shoulders and then he began to peel off her dress and as soon as her gorgeous breasts were in view Josh began to kiss and suck her nipples.
Riley loved having her nipples sucked. They were incredibly sensitive and she panted and groaned as he worked her bosom with both hands and his mouth. He devoured her breasts and Riley felt as if she might cum just from his ravishing her tits.
It had happened before, but not in years. Back in the early days of prolonged teenaged groping when guys weren’t sure if they would get to the next base, they would get her almost as worked up as she was now by sucking and nibbling her tits for what seemed like hours.
This had only been moments and already Riley felt a tremor in between her legs that threatened to spill her over the brink of climax one more time.
Riley opened her eyes looking for a place to move to that would be more comfortable when she saw Maaka still there filming.
“Wait. Wait, wait, wait.” She had to keep saying it to get Josh’s attention.
“Maaka is still here.”
“He’s filming us…”
“Yes. Does it bother you?”
“Well… yeah… I mean why?”
Josh sat back and looked at her for a moment. “Well not to be too crass about it, but I did pay $370,000 dollars for the privilege of fucking you. I think I deserve a record of the event. Plus the agreement was anything I want to do to you. I want to film you.“ He paused and the look in his eye became worried. “Are you backing out?” He sounded hurt and disappointed, like a kid finding out he didn’t get to go to Disneyland.
That was the first glimpse of the honest vulnerability she had seen from Josh in the first moments of meeting him. For one moment he was not the sophisticated confident older man he had been all night. Now he was that oddly scared man from earlier, and it made her want to comfort him, even though she was the one being compromised.
“No. I’m sorry it was a shock is all. Just send me a copy later. Now for God’s sake fuck me will you?”
Josh began to take off his jacket and Riley reached for his shirt and started undoing the buttons. It was frantic and inefficient and felt amazing to be tearing his clothes off. When she had his shirt off she was stunned at how fit he was. His body was practically sculpted, and he had tattoos. Not a lot of them, but a couple big ones, in some tribal pattern that wound around his muscles in a dizzying pattern.
With his shirt off and his rocking torso exposed, Josh then bent his attention on getting Riley naked. She helped him by lying back on the floor as he pulled her dress down her hips. When her dress became caught up in her shoes he pulled those off as well and then quickly pulled her panties down as well. Suddenly Riley was totally naked, her body utterly exposed. He had seen her nudity in pieces before but now that she was unveiled Josh took a second to observe her whole body.
“You are so sexy. Jesus Riley!”
Leaning back on her elbows Riley spread her legs for him, and the camera. Self-consciously she allowed both men and one machine memorize her nudity and she blushed head to toe while she did so. Her leaking slit was sopping wet from all this exhibitionism and Riley was beside herself with the need to be seen, filled and touched by this man.
Josh pulled off his pants and underwear in one move, his erection bouncing lewdly with his movements. Riley couldn’t take her eyes off of the long pole of meat. As Josh sat on the floor to pull his pants off his feet Riley swooped over and began to suckle his beautiful pole once more. She couldn’t keep her mouth off of him, his cock fit so well between her lips that she was compelled to take as much of him in as she could.
As he wriggled out of his clothes she jacked his shaft into her oral embrace and licked the tip of his cock happily. The smooth head of his cock slipped in and out of her lips, the feeling of his knob so glorious in the soft grasp of her mouth.
Then at last he was nude he pushed her mouth off his boner for the third time. This time however he pressed her to the hardwood floor and positioned himself at her steaming juncture, ready to fill her greedy pussy with manhood.
Riley held still quivering, but unmoving, needing to have him plunge into her depths.
As he entered her, passing the tight ring of outer vaginal muscle Josh held himself above her, his body trembling with the careful restraint he was showing. Riley appreciated being given time to allow her body to relax and open to him, but she wanted him inside more than she wanted his patience.
Lifting her hips she pressed upward against him, pushing more of his hard cock into her yielding depths. Then with both hands she gripped his tight buttocks and pulled him down into her.
Taking the hint Josh shoved himself deeply into Riley’s saturated slot. Gratified to finally be full she whimpered her pleasure, unable to speak as electric delight washed over her emanating from the hidden depths of her happy pussy.
Riley reached up and clung to Josh as he began to fuck her hard and fast.
“Don’t wait. We have all night. I want you to fuck me hard and cum with me.” Riley gasped, and bucked her hips up to meet his thrusts.
Josh grunted deep in his throat and began to kiss her.
The two of them clutched and ground themselves against each other intimately. Riley had been with long-term lovers who didn’t feel this in synch with her body. Josh fucked her exactly how she wanted to be fucked, even as she changed gears as her orgasm built, too large to contain, he altered and adjusted his thrusts and pace to match her own.
They kissed and stroked each other passionately and when she started to cum Riley begged him to join her.
“I’m cumming. Oh please cum in me, do it! Fill me up! Oh god! Oh god!”
Then she felt Josh ramming her faster and harder and she lost control and began to climax powerfully. She felt so much ecstasy that she couldn’t move anymore. She clasped him tightly begging him silently to stop pounding her so well; her rapture was ripping her sanity to shreds.
Trying to grip him with her arms, legs and the deep muscles of her cunt she clutched him tightly trying to keep him lodged deeply inside her ravenous slit. But her orgasm continued building until it broke over her in a wave like a tsunami.
Riley fell limp, unable to control her body any longer as she shuddered in the wake of the most powerful climax of her life.
Then horribly he pulled all the way out of her, his strength overwhelming her, her climax robbing her of the ability to hold on to him. Looking up with teary, unfocused eyes she watched as he jacked-off over her and saw the first spurt of his jism spray out over her belly and chest.
Feeling his hot seed land on her fevered skin made her spasm with exaltation and she exploded with another orgasm. As he spilled his seed over her she juddered arrhythmically on the floor helpless withstand the power of her climax until he too was rendered too weak to continue and he flopped down beside her on the floor.
Panting and weak from the extremity of her climax Riley lay spread eagle on the floor spattered in Josh’s sperm and feeling utterly gratified from the release of all that sexual tension.
“Holy shit that was incredible.” She sighed. Maaka continued to film them. With one lazy hand she began to smear the sticky sperm around on her skin, looking directly into Maaka’s camera. It was a sordid, depraved thing to be doing, but it felt good on her still hyper-sensitive skin and she liked looking into the camera knowing that one day Josh would watch this and remember her.
Then Maaka lowered his camera and turned it off. “You guys want a drink?” He asked, his light voice higher than his size would have indicated.
Both spent lovers agreed and Maaka went across the room to a full bar and began to make them both drinks.
Chapter Five: Triple or Nothin’
“You happy?” Josh asked.
“Yes. I feel wonderful, liberated actually.”
“Uh… I guess so. It hasn’t really sunk in yet.”
“By my count you have over half a million dollars now.”
The number stunned her. Riley quickly did the math. $375,000 from the poker game, $50,000 for the show at dinner, $100,000 for the lap dance. She did have over half a million dollars. She was filthy rich by her usual standards.
“Holy shit!” she sat up, jism trickling down her bare skin and she looked at Josh like he just told her he was an alien. “I do! I am rich!”
They both laughed, he at her joy and she with sheer delight.
Riley leaned over and began to kiss Josh again. She would have fucked him once more, but he put his hands on her shoulders and pushed her away a bit. Looking deeply into her eyes he spoke to her seriously.
“A lot of things are going to change for you after tonight. A lot. Everything. I know, I’ve been through it, in a way. And if you want me to- I can and will help you deal with everything, but first you do need to know who I am.”
Her mind was whirling, but his calm, serious demeanor caught her attention and she focused in on him. Sudden fear spiked in her belly. Was he trying to take the money back? Could he renege on the deal? ”Okay. So, who are you?”
“I’m a porn producer. I’ve made millions and millions putting out websites, and videos about real world women in sexual scenarios. Ex-girlfriends, webcam stuff, you name it. If it’s amateur porn I’m involved somehow. The difference I try and bring- the real point of pride I hold myself to- is that I know the names of each of the men and women in my videos. I work with them; get to know them a little as they enter a new world.”
Riley was appalled. She felt violated and suddenly feared all those videos the public had been taking of her. She would look like a slut to the whole world. She curled in on herself on the floor, covering her nudity, feeling his cum smear over her skin as she hugged her knees to her chest, suddenly ashamed of what she had been so proud of moments before.
“Okay, here let me get you something to cover up with.” Still naked himself Josh went to a couch and took a beautiful angora blanket from the back and brought it to her. “Come on, get up and join me on the couch for a moment. I’ll make this seem less horrible.”
Riley stood, took the blanket, wrapped it around herself and walked like a zombie to the couch and flopped down onto it.
“Now first off I didn’t target you or anything. Everything that happened between you and I in the poker room was a surprise to me. I had no idea you would flash those players. The bet was real. I was so turned on by what you were doing that I made the bet with you as a fun way to see if I could sleep with you. I wasn’t trying to manipulate you at all.” Riley tried to remember how much of that she had initiated, knowing what he was saying was true.
“You seemed so game, so fun loving, that I tried the stunt in the restaurant and you went for it. Everything after that was to see how you would react. To test how brave you were. I think you could make a shit ton of money.” He spoke gently, clearly trying to make her more comfortable. “My guys have already started collecting the names of anyone they could who was filming you. We will offer to buy any and all footage of you anyone took from tonight. You have the money to buy it from us if you like, or we can sign papers to legally stop the publishing of any photos of you, no problem. Or…”
Riley looked over at him, her fog of panic slowly lifting. “Or…?”
“Or we can finish what we started tonight. “
“What does that mean?”
“Riley, I’m telling you in all seriousness that you put on a fascinating show tonight. You looked amazing in everything you did, and men and women are going to want to see what happened when we got here. They are going to want to watch you have sex. They will pay to do it. If you are willing we- you, me and my company, could make a huge load of cash if we release the videos of you from tonight.”
“But- what about… my… life?”
“It will be different. Totally. But it’s going to be different anyway. Nothing will be the same for you now that you have that money. I made a fortune in less than a year when I started out. I made Ex-girlfriend videos. They appeared to be boyfriends getting revenge on their exes by posting sex tapes they made together. Actually I always found the women in the videos and worked out a deal, a four way split. The guy, the girl, me and my company. Every person in those videos knew what they were doing and made money off of them. But it changes everything. It does. I have a team of financial advisors, PR people, and best of all, therapists who are sex positive, who will help empower you about any decisions you make. It isn’t perfect, but it is not exploitation. Not without consent anyway.”
“This is insane.” Riley felt adrift, unmoored from what she knew.
“I understand exactly what you are going through. The very first video I released was my own. I was broken hearted, and felt betrayed and I uploaded my ex-girlfriend and myself. It was wrong and I have done everything I could to make it up to her. She is a partner in the company and she helps other women deal with this new exposure, if they decide to go ahead with it. So I do understand what you are feeling as much as anyone can.”
“I feel like this is too big for me. Too public.”
“I understand, I do. I’ve seen similar things to what you are going through in many others. The difference is that you already have a lot of fucking money so you don’t have to agree to anything. Other people usually need the cash or they wouldn’t be meeting with me.”
“Riley let me ask you something? Did you have fun tonight?”
“Did you enjoy having all those people looking at you, getting off on you… filming you?”
“Did you think about their eyes on when you were dancing, baring yourself, cumming in the car? Did you think about Maaka’s eyes on you while we had sex? Did you enjoy him filming us?”
“Yes.” She said in a small voice.
“None of that has changed because of who I am, or what I do. As far as you are concerned all of that was innocent fun, right?”
“Well… not quite innocent.” She smiled a little, knowing how much she got off on being watched like that.
“Okay. Fair enough. So… if you say the word my team will collect and buy all that footage, and block it from ever being released on the internet or anywhere else. We can do that. It’s easy and legal and doesn’t even cost much. That is far more control that you would have had if I wasn’t who I am. Right?”
“Yeah, I suppose so.”
“Okay, so as far as you have to be concerned that can be the end of it. A crazy night that cost very little compared to what you earned.”
“Okay, I get it.” she did feel relieved. The shock of her potential exposure was mitigated by the reasoned explanation he gave her.
“So, now all I’m asking is for you to consider the next phase.”
“I guess we could think of it as the next bet. I bet you the potential profits we could earn that if you let me release these videos on my websites that we could have a huge hit on our hands and make a shit ton more money for both of us.”
“You’re looking to release the film Maaka shot?”
“All of it. I’ve been thinking about this ever since we left the restaurant. The story would follow us all night, from the casino to the restaurant to the strip club and the car, to the elevator and here. We piece together all the found footage, like a Blair Witch thing. We could spin it a lot of ways. Who is this girl? Or the Greatest Bet Ever. I have marketing people who can make a meal out of this. Then we release the videos a bit at a time, as if they are being leaked by all the people who shot it. Which they would be. Through us. Then we release you and I fucking, and I have an idea for the finale as well. People will go ape-shit for this.”
“Man I don’t know…”
“If we never use your name we can always deny it is you. You don’t have any tattoos, there is no way to prove beyond a shadow of doubt it’s you, except in a court of law, I guess. Plus, think of how good it felt knowing all those men were getting off on you dancing. I know that felt good. This is even better. Millions of people jacking off, getting off, because you look so sexy. What a thrill.”
It was a thrill, she felt herself tingle even at the thought of it.
“What’s this finale you have planned?”
He sighed. “I don’t know if you want to hear this just yet.” He ran a hand through his hair, looking a bit self-conscious for the first time all night. Josh still sat naked on the couch beside her and as she looked at his lean, well-toned body she grew aroused once more. What sort of thrilling sexual adventure could he come up with to top what they had done already? Just thinking about it made her breathing shallow and her nipples poke hard against the soft angora of the blanket she was wrapped in.
Riley had always enjoyed the kind of porn Josh was talking about. She had let past lovers film them while having sex, enjoying having the camera to play to. The thrill of thinking that someday it might be on the internet had added a great deal to the experiences.
“I’m probably an idiot for telling you this, but I am so fucking horny thinking about being filmed and shown online that my pussy is throbbing. I really want to know what this finale is, because if it sounds sexy I’ll probably do it. But that isn’t consent to show it online yet.”
Josh smiled is old wicked smile from earlier.
“Okay… Well the next scenario would be just after you and I finish having sex. I think it would be super-hot if the guys, Maaka and Julian came out having been watching us all night, and then I bet you that you won’t let the two of them fuck you at the same time while I film it. But of course you do.”
Riley’s pussy had a spasm just thinking about having two men at once. That had always been a fantasy of hers. The sheer size of those two hulking body guards had her squirming to be taken by them.
“Jesus that’s sexy.” She gritted through clenched teeth. “But will they want to?”
Josh laughed out loud at that.
“Oh believe me, they will be thrilled. First off because they are straight men and you have had them rock hard all night, but secondly because they are both porn actors. They work for me as my body guards part time and as porn actors part time. They’re down, believe me.”
Riley got even wetter thinking about fucking two professional porn actors. What kind of life was she suddenly living?
“But what if I’m no good now that I know what’s going on? What if I get too self-conscious?”
“Riley you were born for this. You make this look easy, but it’s not. Plus I will direct you from behind the camera. I can make it seem natural, not like porn directing. I’ve never really done that anyway, but I know what works.”
Riley couldn’t believe she was seriously considering doing it, but the idea of fucking two men on camera was very arousing. It was the fulfillment of a long standing sexual fantasy. Also she felt like celebrating her new found riches, and as horny as she was this seemed like the best way to do it. But she had one thing to add to the mix.
“Do you have a tri-pod?”
“Then what if I fucked all three of you?” Under the cover of the blanket Riley had begun to stroke her burning clit. Three men would be amazing.
Josh’s smile indicated he agreed. “Sounds perfect.”
As Riley sat on the couch, her mind whirling about her choice, Josh went and got Maaka and the other body guard Julian and made all the arrangements for the shoot.
Sitting there alone Riley tried to prepare herself for what was about to happen. She was going to fuck three men at once making a porno film. This shift of everything she thought she knew about her life was numbing, complex and overwhelming so when the men all came back and Josh told them what was happening she was grateful to simply begin and stop trying to process it all.
“OK, I think the best thing to do is to pick up from where we left off before. The two of us on the floor, Maaka filming, and then Julian you can enter in a bit. Riley? What are we talking about here? What are you willing to do and not do?”
Riley sat still, flabbergasted. She was being asked what sex acts she would and wouldn’t do on film, or in life, she supposed. What were her limits? She had no idea right now she was so horny and confused.
“Um… I guess I’m not too into pain, so take it easy on me and let’s just see what happens.”
Josh smiled a proud smile, “Atta girl.” And he positioned himself on the floor where they had fucked not long before. “Come here.” He patted the floor lightly encouraging her to join him.
She lay down next to him and Maaka directed them into similar positions to where they had been, after he checked the end of the last shot. Then when Josh was once more beside her and Riley was spread out as she had been after Josh shot his load on her Maaka began to film as Riley pretended to still be spreading the now dried sperm over her belly and breasts.
When she saw that the light was on and the camera recording Riley moved over to begin kissing Josh passionately. She was still totally turned on. Knowing she was making a porno, not merely a tape for a lover to replay had her extremely wet. Even though she was more aware of the camera, she was no less into being seen than usual. She loved it, deep in her belly she relished knowing that thousands of men would masturbate to these images.
Kissing Josh she tried to get him going to fuck her once more, but he demurred.
“I’m sorry babe, you drained me, for now. If you still think you wanna fuck I’ll bet you ten thousand bucks you won’t fuck Maaka right now.”
Riley looked into the camera instead of Maaka’s eyes, bit her lip pretending to ponder the offer, then said “I’ll do it.”
She crawled over to Maaka and looking right into the camera she undid his belt and pulled out his flaccid cock. Even soft his penis was impressive. It was thick and girthy with dark skin and gnarled veins.
Riley took the head into her mouth and began to lick and suckle the knob as she stroked the soft shaft urging him to fullness with her eager mouth. She had never sucked the cock of a man she had never even kissed before, and suddenly it made her self-conscious.
Riley then closed her eyes and focused on sucking him the best way she knew how, with love and compassion. She wanted him to feel wonderful, to enjoy her attention. It was all about him. Not the unknown people watching.
She began to pretend he was a long loved partner, a person she cherished and wished to bring joy to. Riley lavished his growing cock with the adoration she would give to a cock that had given her hundreds of orgasms.
Feeling the big man’s cock grow large in her mouth and a growing affection for him in her chest she was able to open her eyes once more and look up into the lens of the camera. Letting it be her lover’s eye Riley gazed into the aperture and let her pleasure and affection beam out.
She lapped at the now large cock that she could barely fit in her mouth and stroked it gently bringing him to his full size. Taking her mouth from his knob she began to lick along the sides of his huge cock, she looked down at it and laughed as she realized his prick was bigger than her forearm.
She placed her arm next to his shaft and saw that he was thicker at the widest point than her arm was at its widest, and that the entire length was longer than the space between her elbow and wrist. It was likely eight or nine inches long and as thick as a soup can at the widest.
“Jesus. Where am I supposed to put all that?” she laughed.
“Now you know why I bet you ten thousand you wouldn’t do it.”
Still stroking the huge wang Riley looked over at Josh and said, “Fuck that. I’m taking all that beast. This is going to be great.” This wasn’t acting, she was desperate to feel this mammoth cock wedged inside her tight pussy.
Riley went back to sucking the massive pole and loving every second of it. This was the mightiest erection she had ever seen, even in porn, and she was going to enjoy all of it. Riley began licking and sucking Maaka’s balls and making a meal out of how much she enjoyed the size and taste of them.
Moaning and purring to herself Riley made love to this impressive penis from top to bottom with her yearning mouth until Maaka couldn’t take it anymore and pulled away. He pushed her back toward the floor and began to pull his clothes off.
Riley lay down panting in anticipation as Josh took over operating the camera and Maaka prepared himself to fuck the shit out of her.
This was it, Riley was about to fuck a porn star and become one herself.
Maaka finished undressing and knelt between her legs. Riley opened wide to stretch her thin legs around his big thighs, the muscular man a sculpted monster now that she saw him nude. His body was thick and meaty, but cut without any fat on him. Huge slabs of muscle coated him from head to toe and Riley felt a visceral reaction in her body.
This was a Man!
Riley never usually liked the body builder type, but something about the lurid, carnal nature of this encounter had changed her in some fundamental way. This big huge man had her shuddering with lust before he even so much as touched her.
Positioned between her thighs Maaka took hold of his member and aimed the large dark knob of it at her slippery opening. Running the head of his cock along the groove of Riley’s sex Maaka teased her, getting her ready to accept his imposing tool.
When his tip rubbed over her sensitive clit Riley bucked her hips seeking momentary escape from the electric frisson of his touch. Immediately afterward she tilted her hips up pushing her clit hard against his knob as he brushed it back and forth between the lips of her soaking wet pussy.
Riley mewled desperate sounds as he continued to tease her with his cock, holding his rod in one hand massaging all around her dripping sex moistening his whole cock-head.
When at last Maaka seemed to feel she was ready he pressed forward and opened her up with his large knob. Gasping as she felt her cunt stretched wider than it had ever been Riley did her best to relax as he crammed what felt like ten penises into her tiny opening.
It didn’t hurt at all, but the stretching felt profound, like a new yoga position she had never done before stretching her in ways she hadn’t dreamed possible.
Riley felt the invasion of his member deep inside and she trembled with the need to move and shove even more inside, but she resisted. Riley appreciated the slow pace Maaka was setting; it gave her time to adjust to so much cock within her small cunt.
Then when he bottomed out, touching her cervix Riley felt a huge orgasm begin to swell in her belly. The sheer size of him, the fact that he had hit the very depths of her insides and had more to offer filled her with so much desire, such profound sexual appetite that she felt like she was losing her conscious mind and becoming an animal in heat.
When Maaka pulled out almost all the way she felt hollowed out like a gourd. Her body tingled as it tried to readjust to being empty, but before the elastic walls of her pussy could squeeze closed again he once more shoved into her, and little more energetically than before and that was all it took. Suddenly Riley was cumming, hard.
Some orgasms were dreamlike and ephemeral, some were immediate and shocking, this one was relentless and profoundly powerful. It came from so deep a place in her mind and/or body that it felt distant and enormous.
The wave of delight started in her feet and tingled up her legs while simultaneously filling her belly like air. When the tingle in her legs reached the spreading pool of passion in her belly it exploded like one storm front hitting another, detonating up into her chest and filling her heart with volcanic lust.
Riley began to shove her ravenous pussy up onto the huge slab of meat impaling her meeting each of his thrusts as Maaka stabbed down into her, aggressively lifting up to meet the beast that gored her.
She had never had an orgasm where she retained such precise control of her body but this time she could maneuver perfectly and drive herself up onto the source of her pleasure. It was amazing.
A quick glance to the side showed her Josh sanding near-by, both the camera and his throbbing erection pointed right at her face. Embarrassed to be seen grunting and cumming so shamelessly, Riley pulled herself up Maaka’s massive arms and began to kiss him hungrily as he drove in and out of her violently quaking cunt.
The extremity of her orgasm had Riley whimpering encouragement to Maaka. “Yes. Yes. Yes.” She begged over and over needing him to continue pummeling her pussy.
Looking down she saw that only a couple inches of his huge cock remained outside her body, which made her start cumming even harder knowing there was more to go.
Maaka lifted her legs up over his massive shoulders and began to fuck her like a pile driver, slamming down into her pussy as she lifted her hips up to meet his down thrusts.
Riley felt so thoroughly fucked she thought she might black but, her orgasms throbbed and swelled every few seconds ripping any inhibitions she had left lingering in her tattered self-respect. She was a depraved slut begging to be filled full of strange cock. It was nothing like how she viewed herself normally but tonight there were no limits to the debauchery she seemed capable of.
Then Julian came into the room.
“Hey boss, what’s up?”
Josh moved so that he could view Julian over the two rutting figures in the foreground.
“I bet her she wouldn’t fuck Maaka, I guess I lost.”
“You think she’s take another bet? Will she take on both of us? I’ve been wanting to fuck this girl all night!”
Julian was a big black man, and Riley feared, and anticipated that he too would have a massive cock.
“Lemme see what you’re packing before I take this bet.” She said, her words coming out strained and punctuated by taking deep thrusts from Maaka’s substantial tool.
“Girl you can’t handle this shit.” Julian scoffed as he pulled on his clearly erect cock through his pants.
Even hidden it looked really big. That threatened to unhinge her feeble grip on her self-control. Desperately trying not to lose focus from yet another terrific climax Riley called out, “Let me see it!” while enduring a relentless assault from Maaka.
Julian unzipped and whipped out a long thick cock that made Riley’s mouth water. It was thinner than Maaka’s but potentially even longer, the ebony erection looking delicious to her in this frenzied state.
“Gimmie that fucking cock!” Riley shouted, suddenly a foul mouthed, cock hungry slut apparently. Julian began to undress.
“You gonna get it girl.”
As Julian undressed Maaka pulled out of Riley, her body now so acclimatized to his huge cock that she didn’t feel her vagina relaxing back into its smaller shape immediately. Maaka told her to get on all fours and Riley scrambled to obey, enjoying being the passive member of this trio.
Julian stripped down to his socks and came over to join the fun. Both men began to feed their big cocks into her willing orifices, Maaka back into her gaping pussy and Julian slipping his long rod between her lips.
Riley began to slurp on his smooth tool, relishing the warm, musky feel and taste of this new penis. Riley had never taken two men before and the intensity of the sensation was mind bending. Perhaps if the cocks involved had been smaller she might have felt differently, but being utterly stuffed and stretched to new openness in her pussy while trying to swallow a longer cock than she had ever seen seemed incredibly vulgar to her. The thrill of being so unabashedly wanton had her climaxing once more.
On her hands and knees she allowed her brain to shut down and her body to take over. Simply a vessel for pleasure she felt both men use her, driving into her body savagely while she opened to them as much as she was able while undergoing such a release of bliss.
The only part of her being she was able to in anyway control was her mouth, simple moving her lips and tongue around randomly over the hard flesh slipping in and out of her grip.
Meanwhile her body was well aware of the thick shaft moving in and out of her lower opening. Each thrust that penetrated so deeply she could feel her intestines moving drove her further from the person she thought she was, out into unknown territories of pure delight.
Every scrape of flesh on flesh, each slip of smooth skin over tender erogenous zones impelled her to new depths of depravity. When the men began to grope her breasts where they bobbled beneath her torso she wailed her gratification to the skies, a mouthful of manhood muffling her passion.
Riley rocked back and forth forcing either one end or the other of her athletic body to be impaled on one cock or the other. The men held still while Riley pleasured herself with their cocks, climaxing over and over as she filled herself with them.
Then she lost her ability to move, her body reached a new limit of pleasure and she began to convulse and clutch at her lovers as her entire being seemed to explode in one long sustained orgasm.
Riley lost awareness of who she was, what she was doing and why. All she knew was white hot, coruscating pleasure. Nothing remained by blinding, purifying sensation. Every cell in her body seemed to be achieving ecstasy at once and it was so overwhelming that she felt like a tiny piece of flotsam on a huge argent sea of pure delight.
Enveloped in this endless ocean of pleasure she was submerged in unadulterated rapture. And there she stayed for an eternity.
That ended as soon as the men lowered her to the floor.
She had gone limp so her lovers let her fall to one side and Maaka positioned himself behind her lifting her top leg high to expose her wide open juncture so the camera could capture his huge dong invading her deepest recesses.
Julian stuffed his cock back into her slack jaw and used her mouth mercilessly, stretching her neck back as her head was forced into an awkward position to allow him to kneel and fuck her face as she lay on her side.
The men held her immobile as they used her limp body, her brain still not able to fully take control of her limbs as they flopped and shuddered with aftershocks from her powerful climax.
Maaka reached around and mauled her tiny breasts as he drove most of his huge member into her sloppy pussy that leaked the fluid evidence of her orgasm all over them both. Drool seeped past Julian’s cock as she slobbered over his knob, her lips still feebly gripping his shaft and her tongue flicking around the underside of his head.
When Riley was at last once more able to control her body she wriggled and adjusted into a more comfortable version of the position the men had maneuvered her into. She began to participate, more actively sucking and fucking the cocks so wonderfully assailing her.
In flashes and glimpses she caught what Josh was doing, moving the camera here and there capturing on video whatever caught his eye. For an embarrassingly long amount of time he focused down between her legs.
With her head tilted back and slightly to one side to accommodate the cock moving in and out of her mouth Riley could only barely perceive Josh’s position. But she saw him bent way over with the camera aimed to the place Maaka was piercing her.
The idea of millions of people seeing her sex stretched wide around the massive tool filling her seemed the most lewd, vulgar and humiliating thing she could imagine right now. And knowing that her enflamed clit was exposed in all its tender glory compelled her to begin to touch it.
Her fingers drifted down and she began to slide her fingers all over the tingling centre of her sexual delight. The moisture there astonished her. Her pussy leaked so much fluid that her entire groin was slippery wet. Spreading her fingers around she rubbed the area to explore how much fluid she was seeping.
A few moments of delightful massaging revealed that her pussy, legs, buttocks and Maaka’s balls and belly were all coating in her cum. She found this so obscenely erotic that she began to cum once more as she rubbed her swollen lips and clit where they stretched impossibly around Maaka’s tremendous cock.
Now Julian lifted his prick from her mouth, cascading drool over her upturned cheek and while she shivered and quaked with a powerful climax he dipped his testicles down over her mouth and told her to lick.
Cumming in a series of tumultuous orgasms Riley slathered Julian’s balls in spit and sucked the round orbs down through the taut flesh of his scrotum. Lapping at his dangling sack she bathed him worshipfully while cumming and cumming again and again from frigging her own clit and being pounded by Maaka.
Never had she been so lewd, so perverted and it felt liberating.
Maaka tugged on her tender nipples and groped her breasts and driving her wild with excessive stimulation.
When her ministrations became distracted Julian once more began to fuck her face, taking control of her head with his hands around her forehead and throat. The aggressive manhandling, and semi-dangerous position made her cum harder until she once more lost specific awareness of her body and became a small consciousness enveloped by pure delight.
The men moving her into another position is what brought her back.
Glancing around as her body suddenly became emptied of cock Riley saw that Josh was getting the camera onto the tri-pod and that the guys were moving.
Like a cold splash of water she was suddenly awake, torn from her orgasmic dream-scape. Julian helped her stand and they all trouped over to the couch where Josh aimed the camera at the place Julian sat her.
Dazed and disoriented Riley tried to figure out what the men were doing. Julian went to the camera as Josh crawled up onto the couch behind her. Josh then spread her buttocks and smeared his cock around in her soaking wet nether lips. Each brush of his spongy cockhead on her tingling clit made her jump and moan.
Then Josh pressed his cum drenched member to her sphincter.
“You ever done anal?” He asked.
“No. Never.” Suddenly faced with the possibility she wondered how she felt about it.
“Get her face in the shot as I enter, it’s her first time.” Josh said to Julian and he hesitated while Julian adjusted the framing of the lens.
“Was he just simply going to do it without asking permission?” Riley asked herself. When his knob spread her anus open she had her answer. It felt similar to accommodating Maaka’s massive tool as Josh opened her virgin asshole with his insistent cock.
Riley felt herself pressing down onto him and opening up her sphincter, answering the unspoken question as to whether she wanted this to happen or not. She did, and it felt wonderfully sordid.
As Josh wedged himself into her ass Maaka approached and fed her his huge dong. For a fraction of a second she balked at tasting her own musky juices on his hard member, but the flavour and the sleazy nature of what she was doing was too intoxicating to resist.
Taking as much as she could into her small mouth Riley sucked him and slide her tongue everywhere she could, tasting her cunt on him, glad for the distraction from being pierced in her dark hole.
When she felt Josh begin to fuck in and out of her ass she thrilled at the tingling, slightly burning feeling of him moving in her bowel. His cock fit snugly inside her anus and she felt blooming pleasure with each thrust.
Meanwhile Maaka fed her grateful mouth his giant erection. Slavering appreciating over the huge boner that had given her so much pleasure Riley felt humbled by his size and the sheer joy he had given her with this magnificent manhood. Worshiping him she devoted as much of her attention as she could on him with hands, lips and tongue.
Then she felt Julian moving between her legs. Stunned by what was going to happen she pulled back a bit from the devoted grovelling she was doing to Maaka and sent some attention down to her pussy as Julian began to enter her drooling cunt.
It must have been awkward down there with so many legs to negotiate, and she felt someone lift her top leg and expose her more completely to be plundered by all the men. Finally Julian entered her and she was being fucked by three men at once for the first time in her life.
All in all something close to twenty five inches of cock was being shoved into her all at once and she felt like the biggest, dirtiest most degenerate slut in the world. She could hardly believe three big pricks were moving in and out of her petite body. The stretching, filling, sliding feeling of all that meat in so many places, of hands all grinding her tits and groping her ass and legs was bewilderingly tantalizing.
Every nerve in her body was alive with pleasure. Her being was suffused with pure joy as these men fulfilled her deepest, raunchiest fantasy. The one she saved for long weekend masturbations.
In no time at all she was once more climaxing, sobbing her pleasure around Maaka’s massive tool.
It seemed to last a long time, this orgasm. It was either one tremendous long one or so many little once crammed together she couldn’t tell where one started and one ended. All she knew was that she couldn’t breathe she was wracked with so much delight.
The dizzying moment, the vertiginous feeling of falling over that sometimes heralds sleep shook her back to awareness as she felt herself slip into unconsciousness.
The men were all hammering into her grunting and huffing as they pounded their way toward their own long withheld orgasms. They were whispering to each other appearing to try and time their climaxes.
“I can’t hold it anymore.” Julian hissed.
“Okay.” Josh whispered. “Riley get on your knees on the floor.” Al the men extracted themselves from her body and she felt lightheaded as her body was suddenly denied all that manhood.
She practically flopped off the couch onto the floor and Maaka helped her to her knees, she was so dizzy she nearly toppled over. Then the three men were all aiming their cocks at her and jacking off over her puzzled face.
Then she saw past the towering erections at the fierce faces of the men, all close to cumming and she understood what was about to happen.
They called it Bukkake .
Even as she adjusted herself to see the camera and allow it to see her, Julian began to spurt semen onto her face. Turning to him she opened her mouth hoping to catch his jism there, but he aimed away from her open mouth and shot over her cheeks and forehead, his load of spunk a large hot wet mass that gouted over her face.
Stretching her tongue as far as she could Riley attempted to gather some of the sticky fluid into her mouth, but it eluded her as it oozed across her features.
When Julian stepped back and then away Riley used her fingers to scoop the viscous mess into her mouth taking as much of it as she could.
Julian went to the camera and lifted it off the tri-pod and brought it over as the other two men jerked off over Riley.
“That’s great Riley, but leave the rest. Just lick it off your fingers for the camera. Don’t touch the other loads either. We’ll put some on your tongue if you stretch it out.” His voice was tense and he was pumping his cock the whole time he spoke and she wanted to help him cum so she reached up and began to lick his knob as it bounced before her. With her hands she took both cocks and began to massage their balls as she had seen porn stars do.
Then Maaka began to cum. His enormous balls produced an impressive load of sperm. The first spurt landed on her closed lips, she didn’t know it was coming, but she opened up and the next jet landed across her tongue and lips.
Holding her mouth open she tilted her face up and allowed a stream of jizz to coat her face. Over and over he spurted an eruption of thick cum over her. She had to close her eyes as he pasted them shut with more cum than she could imagine.
Then she felt even more, but heard Josh grunting over her upturned face. He painted her from forehead to chin in his thick sauce and Riley felt the hot mess sliding down her face and neck to cascade down her small heaving breasts.
She lapped at her lips tasting the jism and shivering with mini-orgasms as the men soiled her with their seed. Defiled as utterly as she had ever been Riley licked the endless supply of jism from her drizzled face. The taste making her cum harder and harder the more she got in her mouth.
“I’m cumming. This is so hot, so fucking filthy. I’m cumming.” She said between licking her lips and reaching for more sperm.
“Get it all. You can use your fingers.” Josh panted.
Riley reached up and scooped the gooey mess down her left cheek to her greedy tongue. Then she began to slide it around in her mouth, savouring the mingled loads. Reaching down with one spunk stained hand she began to masturbate as she swallowed the first payload her fingers delivered.
Then frantically she began to scoop and suck the sperm from her face. She cleared her eyes so she could see, and look into the camera showing how much of a wanton harlot she had become.
She spent several moments cleaning ever scoop of cum she could gather from her face and depositing it in her avid mouth. The camera tracked it all and she gazed deeply into the lens her eyes glazed with pure lust.
When she was done, when all the cum was gone, all the erections milked dry and the men spent Riley flopped backward onto the seat of the couch, her chest stained wet with mingled fluids and presented blatantly for the camera.
Gasping from the aftereffects of what seemed like thousands of orgasms Riley felt as weak as a kitten. The intensity of the last several hours numbed her and left her drained and depleted.
“Say goodbye to your new fans sweetie.” Julian whispered affectionately.
Looking up, her eyes half lidded from sheer exhaustion Riley smiled weakly and blew a kiss off her hand to the camera lens.
Julian shut down the camera and then flopped down beside her. Everyone relaxed, each of them clearly gratified and glowing from a wonderful sexual encounter.
“I can’t wait to edit that.” Josh said. “That was some of the best sex I have ever had. Riley you are going to be a fucking star.
Dubious, she sprawled unabashedly across the couch, her nudity no longer any concern what-so-ever.
“You own me twenty thousand dollars.” Was all she could say, and everyone had a chuckle.
“If you want to clean up there is an amazing shower in my room you should try.” Josh said. “It’s one of those rain fall showers. They rock. There are clean towels on the rack and lots of shampoos and things. Help yourself.” The idea of cleaning all that cum off suddenly appealed very much. She felt soiled, happy, but soiled.
Wandering around the place she stopped to gaze at art and décor all the way to the bedroom, marveling at the style and class of the furnishings.
In the bedroom a huge painting across from the bed drew her attention. The woman featured in the excellent portrait looked very familiar.
Stepping closer Riley stared at the young, slim, blonde woman and wondered where she had seen those elfin features and kind hazel eyes before. It bothered her, but not terribly so she turned away and went into the bathroom and there in the full length wall mirror she saw the elfin blonde woman standing naked, hair tussled, face smeared with glistening jism.
Stepping back out into the bedroom Riley saw that indeed the woman in the painting looked remarkably like herself, they could pass as sisters on the street. The odd, fearful reaction that Josh initially had to Riley suddenly made more sense.
After a fabulous shower in the rain fall Riley found a robe and returned to the living room to see that Josh was alone and similarly dressed in a robe.
He asked about, and she gushed about the shower, then they ate some cheese and fruit he’d prepared and finally she worked up the nerve to ask about the portrait.
“Oh, yeah. That is my old lover Maddie. It was her that I taped and then put online. I’ve never really gotten over her, I guess. It’s my thing, my fatal flaw, I suppose. I just love her, I can’t help it.”
“Does she know?”
“Probably. She is pretty bright.”
They lapsed into silence for a time, both thinking about Maddie and the nature of love. Then to move past the awkward moment Riley went to find her phone and saw a dozen messages from her friends.
The messages plunged her back into the reality of her life and she excused herself from Josh to answer her friends and tell them she was fine.
That began the long process of relating her night to her various worried friends and beginning to acclimatize herself to being very, very rich, by her standards.
Riley didn’t tell any of them about the porno, she wasn’t sure how she could do that just yet, but she told them she met a guy and won a lot of money. Josh came by at one point to tell her where a guest room was if she wanted to sleep, and that he was going to bed.
She used to room to talk to the girls on the phone and try to answer their questions one at a time, one phone call at a time. It took a while because they were drunk, but eventually Riley was able to hang up and go to sleep.
In the morning she braced herself to be a new person and stepped out of the millionaire’s spare bedroom in his borrowed robe and prepared to face all the changed that had happened.
Josh was there waiting, with Maddie and a lawyer and she spent hours beginning her climb to the top of the pornography heap. Everyone was enthusiastic, and helpful, and they offered her a chance to hire her own lawyer, asking her to sign nothing yet, just explaining things.
It was all so kind hearted, professional and friendly that Riley started to get excited about this turn her life had taken.
They made an appointment with the therapist that would help her deal with the negativity she might face with her friends and family, and the media storm that was already beginning.
Television, newspapers and internet chat rooms were buzzing with the story of the big winner and the nude woman. Footage was already out there showing Riley getting her cheque from Josh, naming who he was and wondering who she was.
If it weren’t for Maddie and Josh Riley knew she would have been nauseous with fear over the intrusive probing the media was doing trying to find out who she was. The tone of the writing was rabid and salacious, turning a wonderful night into a sordid tale of debauchery and drug fueled lust.
Josh had people who could turn this around, and in fact he was looking forward to making this a battle over the sex trade and how America viewed human sexuality. Riley was scared, but saw that Josh wanted to make this a crusade, and she found nothing distasteful in what he was saying about how wrong America was about sexuality, so didn’t try and stop him from making her the poster girl for change.
But before that could all get rolling she wanted to go and see her best friends and talk about things.
After the meeting Riley was driven back to her hotel by Maaka and when she was finally with her friends, safe and balanced by their long history together she was finally able to begin the long process of altering her whole life according to how she wanted to do it.
Riley bet it all, the life she knew before, All or Nothing, on change.