This story plays on the classic good girl gone bad theme. It tells the tale of a girl named Alison who leads a very typical college student life. She just happens to live with a wild and promiscuous female friend who discreetly works as an escort. Liana is intent on bringing naive Alison into her intoxicating world of sex, power and wealth and manipulates Alison into taking an escort appointment for her with unexpected results.
I actually based the character of Alison on myself and the character of Liana on a friend of mine that works as an escort but had always denied it to save her social reputation. She often dragged me (or tried to drag me) into unsavoury situations. While I always declined working-girl offers, I could easily see why some girls get seduced by the lavish parties, expensive trips and exciting lifestyle. This story plays on the 'what if' theme and the idea that every choice has its consequence.
Copyright ©2011 Ashleigh Lake. All Rights Reserved. This story may not be reproduced in any manner, without the express permission of the author.
My heart was pounding in a symphonic surge as I lingered in front of the hotel room door. I checked and rechecked the metal plate bolted to the rich, dark oak. Number 2412. Yes, this was definitely the right room. The hallway corridor was empty. The dimly lit sconces glowed invitingly along the richly textured walls. They had led the way from the elevator of the lushly swank boutique hotel, The Hazelton, just like beacon lights leading me towards the precipice of a decision I still wasn’t sure I was ready to make. I could already feel the beads of sweat, responsive to my unsettled nerves, prickling the back of my neck. I anxiously wiped them away, feeling the the tight pull of the ponytail I had been instructed to wear.
I rarely wore my hair in a ponytail outside of the gym or dance class, thinking it only made me look more childish. But it had been specially requested so I had pulled it into a long high blond mane, fastened with a leather tie. The bulk of it still hung past my shoulders and swung like a metronome against my back in rhythm to my quickly accelerating pulse, as I had walked the 4 blocks from the subway station to my destination. And now finally there, I could feel my knees clicking nervously together. Were my hands trembling too? I took a deep breath, recognizing that this was my last opportunity for second thoughts. Was I really ready to do this?
I thought back to earlier that morning, when I had been just another fresh faced college student, waking up after another night of partying with friends at the University Pub. I rolled out of bed, rubbing at my eyes, and started feeling the telltale beginnings of a hang-over headache. It was only when I had been rummaging in the cabinet for the Advil, and pouring myself a glass of ice water that I had noticed that Liana wasn’t home yet.
I had been sharing the apartment with Liana for the past two years and we had grown close, although we traveled in different social circles. I was still a student, and while Liana was the same age as me, she was definitely on a different life path. Liana modeled on occasion, and they were often dubious modeling projects. I had rarely seen anything credible in her portfolio to justify the depth of designer clothes, bags and shoes in her closet, or the way she spent money in cold hard cash as though it was in never-ending liquid supply. And indeed, the black lock box she kept in her bedroom always seemed to be full and was continually being replenished.
She had been very generous with me over the past two years. I was living the student life and dance training took up much of my spare time. What hours I had remaining, I had devoted to working as the hostess at the upscale lounge I was employed at, but those shifts were not nearly long enough and I was always teetering on the edge of being completely broke. Liana was accustomed to giving me loans while nodding to me with a wry smile.
“You’re wearing yourself down for nothing, Alison. Let me know when you want my help with some contacts. I know you will eventually. Why serve others at that bar that you work all night at when you can be the one being served, and be paid for it at the same time. It’s just a matter of time before you realize that it can be a gilded walk for girls like us. You’re just not taking advantage.”
Girls like us. It took me a while to understand what she meant by that statement. Certainly I felt like Liana and I had very little in common. She shopped at Barney’s and Bergdorf’s and I was still shopping at The Gap. She flew out on weekend getaways to Saint Tropez and Monte Carlo with wealthy and exotic men, while I spent my nights working long hour shifts and then meeting up with my high school boyfriend Seth for a last drink at the pub and clumsy sex that I was usually too exhausted to really enjoy.
Liana and I were nothing alike. But she had a beautiful kind of allure and charm that made her lifestyle seem more glamorous than seedy. Being an escort was very different than being a prostitute, she had explained one night over a bottle of wine. It wasn’t being a common whore, it was about being a smart business woman.
“Everywhere tonight, girls are getting drunk at bars and fucking pathetic strangers for free. They’ll wake up in the morning feeling far more cheap and used than I ever will when I wake up knowing I have nothing to do that day but count the green in my wallet.”
The way Liana spoke of her lifestyle was intoxicating to me on many evenings. It sounded so adventurous and exciting, and occasionally she almost talked me into wanting to try it for myself.
“Alison, you’re young, beautiful, and available. These are the years to set yourself up so you don’t have to rely on someone else. I mean look at Seth. Do you really think he’s going to be able to take care of you?”
It always hurt me when she criticized Seth. I hadn’t slept with very many men and I had been dating Seth since my junior year of high school. I knew Seth would never be a wealthy businessman, and our vacations would always be to Cancun and not the Riviera, but I did love him. He was the excuse I used to explain to Liana that I wasn’t interested in her kind of lifestyle. But sometimes, if I was really honest with myself, something within me longed to have a taste of the kind of luxuries that Liana indulged in.
My cell phone rang in the early afternoon while I was aimlessly surfing the net. It was Liana, and her voice sounded raspy and broken.
“Alison, I’m so wrecked. That appointment I had last night turned into an all-nighter. Fucking coke. I haven’t slept at all and I’m on this yacht and everyone’s passed out for the day. I’m trying to wake this fucker up, but he’s still snoring. I need your help.”
Liana often had nights like the one she had just described, but her strangled voice sounded more urgent this time.
“What is it?” I asked.
“You have to take my appointment this evening. It’s really important. He’s flown in from Munich on business. We’re talking about a multi-millionaire, Alison. It’s critical that I not let him down. I meet up with him every time he’s in town, and I don’t want to fuck up his schedule now looking for another girl. I don’t want to lose this contact.”
My mouth went dry. “Liana. You can’t be serious! I can’t just go turn a trick just like that! Why can’t you call your other escort friends?”
I could hear her sighing impatiently on the other end of the line. “Because my other escort friends will scoop his business from me, that’s why. Come on Alison, we’ve been talking about this for ages now. I’m telling you, this is your guy. He’ll be easy for you, I promise. He’s married, and he just like to fuck around when he’s traveling. He’s younger too, and he’s good looking. You’d probably even want to fuck him if you met him on your own.”
I could feel my mouth go dry at the rushed nature of her negotiations. Sure we had talked about it before, but now that the offer was on the table I was petrified. I thought of my boyfriend, my dignity, and my pride in making it on my own in an honest way. And yet looking at the bills stacked on my kitchen table, and the staggered shifts in my schedule, I felt an unexpected tug at my resolve.
“Alison…please. I swear I wouldn’t put you into a situation you couldn’t handle. It will be easy. It’s fucking $10,000 for a few hours! You can keep it all. I just need to keep my client. And it’s too late to cancel on him or make other plans. You have to do this for me. Just this one time.”
Eventually Liana’s pleading voice and rationalizations became more and more convincing. Before I had realized what had happened, she had talked me into it. She explained what I was to wear and what I was to do. She told me the name of the hotel and the hour I was to arrive. Midnight. The way she’d spun it made it sound dramatic and exciting, and I felt myself start to get wet in response to the adrenaline surge. In just one night I would have enough money to cover all my month’s bills and still have money left over. And it was just sex, as Liana had said. It wasn’t love. I looked away from the picture of Seth’s smiling face that I had tacked up on our fridge, feeling a swell of guilt. Liana had said it wasn’t cheating if it wasn’t love. It was a business transaction and nothing more. Her logic was loosely woven and irrational at best, but now having already agreed, I compelled myself to believe in it. And it was just this one time. Nobody would ever have to know.
I spent the next several hours getting ready for the appointment. I spent an extra long time in the shower, trying to drain the tension that was already creeping into my shoulders. I soaped my body, realizing that night I would be giving it over to a stranger to do with what he pleased for money. The idea of it turned me on. I had never cheated on Seth before. My body had known only him for the past 4 years. I wondered what it would feel like to have another pair of unknown hands on me and another cock inside me. The thrill of the idea in theory had my heart racing faster. The reality of it was quite another story. For all my fantasizing about Liana’s lifestyle, and her easy way of talking me into a scenario like this, I still wasn’t sure how I’d react in the moment.
That night I dressed carefully in the outfit she had suggested I wear. She had said this particular client, named Conrad, preferred his woman to be classy and meticulously groomed. Liana had told me not to dress like a common hooker walking into that hotel or I might not even make it past the security. She sent me into her closet to pick out one of her outfits to wear. I liked the idea of this because it helped to further remove myself from the world of being Alison. On that night, I would become someone else. Someone that was meant to fulfill the desires of a stranger… desires that were not my own. The separation of it in my mind helped keep me calm and resolute on following through with my promise.
I dressed in a very short tight black skirt and wore Liana’s 4 inch black Louboutin stilettos. My legs were long and toned from dance training, and the shoes made my tanned smooth legs look luxe. On top I wore a fitted white silk blouse, as the client had instructed with small pearl buttons. No padded bra, I had been told, and so I chose a sheer one that gave my breasts a natural shape and soft jiggle when I walked. My lips were painted red, and my hair was pulled up in a long high blond mane. The look was far more severe than anything I would ever have chosen on my own. Still, I wanted to please the client. And it helped transform my mind into seeing myself as someone other than who I really was.
These were the thoughts that were running through my head as I made my way to The Hazelton. I had several appreciative glances as I walked past the lobby bar, and strode authoritatively to the elevator. But now, as I stood in front of room 2412, my heart was hammering in my chest and I started wishing I’d had something stronger than the single shot of vodka I’d downed before leaving the apartment. This was my last chance to back out. And yet, how could I back out? Liana would be furious after I’d already committed. I’d look like an absolute coward. And she had already done so much for me with loaning me money when I was short on rent, and taking me along to swanky parties when she was invited. No, the time to back out had been six hours prior, and I’d neglected to take that opportunity. Suddenly, everything felt all wrong.
I had only instinctively started to back up when the door swung open on it’s own, and I gasped involuntarily at the unexpected reality of the transaction that had just begun. Standing in the doorway was a surprisingly good looking man that couldn’t have been more than 40 years old. He wore an inconspicuous white dress shirt and dark trousers but I could tell that he was all lean hard muscle beneath it. His hair was cut short, and his eyes were a steely yet piercing shade of blue and they seemed to look right through me.
“You are Alison, I presume?” he said, his eyes raking over me from head to toe in silent appraisal.
His good looks seemed to be offset by a kind of hard, dominant energy that he projected almost unintentionally, and I found something about it slightly unsettling. There was a confident purposefulness in the way he regarded me, almost lewdly, as though I was being served up on a platter for his salacious enjoyment. And indeed, perhaps I was. That was part of the bargain wasn’t it?
Realizing there was nowhere for me to go, I extended my hand to shake his. He just looked at it with amusement, obviously recognizing my nervousness and he let out a low laugh.
“No need for formalities. Come in.”
Embarrassed and uncertain, I walked on trembling legs into the highly modern and stylized hotel room. My heels clicked on the floor as he led me through the suite, presumably to the bedroom. My palms were sweating and I almost felt dizzy with a mixture of fear and excitement at what the next several hours might bring. The air conditioning was on high and I immediately felt my nipples constricting and rising up hard to poke obviously against the sheer silk of my blouse. I felt both exposed and aroused.
It was when we arrived at the main open concept bedroom suite that I stopped in mid-track. Someone else was there. A woman with short jet black hair and bangs was learning into a lounge chair near the bed with a bottle of champagne on a nearby table and a single glass that she was already sipping. She was older than Conrad, but had the looks of an ex-model, still extremely slender and willowy, and beautifully preserved. It was clear she was wealthy from her meticulously stylized image and the diamond jewelry that sparkled from well across the room. She had a feline coldness to her, however, and she regarded me with an amused kind of disdain.
“Another blonde Conrad?” she asked in a heavy intangible European accent. “Why am I am I not surprised.”
I became overtly alarmed. Liana had never mentioned there would be two of them and I started to look around the room, already calculating how I could back out of the arrangement.
“Well, what do you think of her Tamara… is she not to your liking?” Conrad asked, circling around me. He reached out and raked a finger up the back of my spine slowly, making me shiver at his touch. He ended the trail by flicking my ponytail and smiling at me with a cagey kind of hunger that set my nerves on edge.
“She looks just like the kind of little blonde whores you prefer most”, Tamara said with disdain. Her lips curled up in a twisted yet beautiful kind of smile.
I flinched. I had never been called a whore before. Anger and shame flamed through me instinctively, as I fought back my natural inclination to throw an insult back at her and turn on my heels and walk out. But in this situation she was right. I had willingly walked into this role. Suddenly, I began to consider what options I had in removing myself from it.
I tried to find my voice, and it faltered nervously. “Liana didn’t tell me of this arrangement,” I finally choked out. “She didn’t tell me there would be two.”
“Ah,” Conrad said standing back and clearly enjoying my nervousness. He left me standing uncertainly there, at the mercy of both of their scrutiny.
“I should introduce you to my wife Tamara then.”
The brunette tilted her champagne glass my way and then continued to sip it, without taking her eyes off me.
“The arrangement has not changed. Tamara is only here to supervise my pleasure. Not partake of it.”
My eyes widened in response, uncertain as to the kind of game they were playing. Perhaps it was her kink to watch her husband fuck another woman. Tamara’s expression seemed even more deviant than her husband’s. It seemed like she was challenging me, goading me, as though she knew something about me was not cut out for this world. She was waiting for me to burst into tears, or fold. I could see it in the wry smile on her face, and the unquestionable certainty that even though I would be the one fucking her husband, she was the one that held the lion’s share of the power dynamic in that room.
My back stiffened in response to it, and I held back the nerves and fear that had been threatening to overwhelm me since I’d walked into that hotel room. I cleared my throat and held my head up higher. “This was not part of the contract. For another person to be here, even on a voyeuristic level… I want more money.”
The both laughed in unison and I suddenly felt very small and very ridiculous.
“Liana told me this is your first time,” Conrad barked with amusement, “and yet you have the audacity to try to renegotiate before we even begin. Hmmm… I think I’m beginning to like this already”.
My lower lip began to tremble. “It’s just that… the nature of the arrangement was not set out beforehand.”
He crossed his arms and regarded me like a little girl. “Ok, what kind of financial compensation did you have in mind Alison.”
My mind blanked. I had no idea what I was doing even suggesting he pay me more money. But the demeaning vibe coming from Tamara had spurred me to speak.
“I want $13,000.”
Conrad grinned “13,000… really. Do you think you deserve such a price-tag based on your current expertise?”
Tamara’s sharp blue eyes were goading me on with her own private amusement as she continued to sip her champagne, clearly enjoying the interplay.
“I know my worth,” I said boldly.
“How do you know your worth if you don’t come with a pre-defined resume?”
Tamara stood up and crossed the room. Even her movements had a predatory, feral quality to them, and she exuded a confidence in response to my immature and uncertain posturing. Up close, she was even more beautiful, as she dissected me with her eyes. I felt myself shiver in response.
“Whores like you are rarely worth their price, in my experience”, she said with an eyebrow raised. “I think you still have to prove what your real value might be. So why don’t we make it an audition to set the bar. An oral audition is what I have in mind. Get on your knees and try to make him come. My husband has incredible restraint and control. You won’t be able to do it. But I’ll enjoy watching you try. If by some reason I have misjudged you, then you’ll get $15,000. That’s how confident I am in your failure.”
Heat flamed through my face at her offer. I should have turned and walked away. The easy intelligence of this choice was not lost on me. This was my opportunity to back out of the entire insanity of the night, yet a competitive head-strong stubborn kind of resolve had me cemented to where I stood. I was effectively paralyzed by my own ego. Perhaps she had known that I would be, and had played it masterfully this way all along.
As I nodded my agreement, she gave me a knowing smile, condescending and very aware of how easy it had been to push my buttons.
“But first, I believe we are entitled to taste the merchandise,” Conrad said, walking up behind me so that I was standing in between them.
My heart was hammering in my chest as I felt his hands on the back of my thighs. He ran them up the back of my legs before roughly yanking up the hemline of my skirt. I felt the cool air against my bare ass before his hands were on them, raking over the soft skin, squeezing and spreading the cheeks apart, before I felt a sharp slap and the resulting sting that made me cry out unexpectedly. I quickly composed myself as Tamara watched my expression clearly waiting for me to break.
Stubbornly, I kept my green eyes fixed on her cold blue ones as I felt her husband’s hand slide between my legs. His fingers were purposeful as he ran them across my slit, back and forth. He started to tease my clit and I could feel the light pressure of his hard body pressing against mine from behind, as well as his breath on the back of my neck, and I felt myself responsively becoming aroused. By the time he started to press into me, sliding a finger up into my pussy up to the knuckle I was surprisingly wet. The memories of the good girl Alison, my boyfriend Seth, and the moral life I had set out to lead seemed to fade away as I felt him slide another finger into me, moving it around inside me, and expertly stroking it against my g-spot. Just as I started to feel myself settling around the pleasure, he abruptly withdrew, and I was left breathing hard, and alert again to my surroundings.
Tamara was smiling at me, and I felt a deep blush at her knowing expression.
“You are indeed a natural little slut aren’t you,” she said, obviously bemused.
Before I could find the words to speak, Conrad reached around me extending his fingers dripping with my juices and pressing against me from behind so that I could feel the hard bulge of his cock against my ass. Tamara took a step forward, taking his hand in hers, and then drew his pussy soaked fingers past her crimson lips and into her mouth. My eyes widened watching her suck my juices from his fingers, her red lips moving as though it was a cock she was mouthing, all the while keeping her eyes directly on mine.
Finally she pulled each finger slowly from her mouth, and then stood back to regard me with a smile. “She’s sweet,” she admitted, “but now let’s see if this little fuck doll can perform.”
I watched Tamara’s deliberate swagger as she crossed the room to perch back on the chaise and refill her glass of champagne, before nodding to her husband to begin.
My heart leaped into my throat, realizing what was about to happen. Conrad walked around me from behind to face me directly. He was an imposing figure of lean tight muscle, and his jaw was square and seemed to be permanently clenched. There was nothing relaxed about him. Indeed, he exuded masculinity in a way that I wasn’t used to, having only dated guys similar to my own age, and I felt uncertain and out of my element being around him. There were little crinkles at the edges of his eyes as he smiled at me.
“Take off your clothes Alison. I want to see what I’m getting.”
He stood back and my knees started to click together again. I felt vulnerable with those four cold blue eyes on me, appraising me like merchandise. I could feel the air conditioning, heightened again, and the tangible chill was in the room as well as in their gazes.
I swallowed at the lump in my throat and began to fumble with the tiny pearl buttons on the blouse I was wearing. My nipples were hard as ice and they grazed my hands as I worked each button nervously. I tried not to think about where I was, or what I was doing. I tried not to notice how uncomfortable it was to be stared at and lewdly judged.
I slipped the white silk blouse from my shoulders, letting it fall to the floor. Then I slid the black skirt slowly down my thighs, wriggling out of it, before kicking it to the side until I was standing in just a sheer black bra, panties and stilettos. I glanced up and saw them both watching me, enjoying my awkwardness and obvious nerves. Conrad gestured for me to continue and I gingerly unhooked my bra and let it fall away from my breasts, my nipples rising up even harder under his gaze. Finally I slid off my panties, revealing my silky smooth snatch. I could feel the dampness in the panties and realized I was as aroused as I was terrified.
Conrad smiled and circled around me several times while I held my breath and fixed my gaze on the wall. I had no idea what his reaction would be, and my heart was hammering loudly in my chest. They both exchanged comments in German but from their intonation I assumed they both liked what they saw.
“Very good Alison,” he said finally. “You have a beautiful body. I think I will enjoy using it for my pleasure this evening.”
He purposefully stared me down while he unbuttoned and removed his shirt. He had an athletic body, with well-defined muscles that seemed to suggest a certain kind of masculine virility. Next he unbuckled the black belt around his trousers and slipped it from the loops until the entire length of it was in his hands. I flinched as he held it in front of me. In my naked vulnerability, I had no idea as to his intentions and a shiver of fear went down my spine. He smiled and approached me with it, and I began to back up, but his voice was low as he spoke.
“Easy.”
He caught me before I could move too far away and wordlessly, he snapped the belt between his hands and wrapped it roughly around my waist, looping it through the buckle and drawing it tight until the leather bit into my flesh. I gasped, and my breathing quickened. We were eye to eye and I could feel his breath on face as I stared back at him, wide-eyed and uncertain. The more I pulled away from him, the more the belt loop tightened around my waist. It was like he had effectively leashed my body and there was nowhere for me to go under this kind of restraint.
“Now, are you going to struggle? Are you going to cry? Or are you going to show me what kind of a good little whore you can be?”
“I… don’t…”
“You still have a choice in this Alison.”
My breathing came out in uncertain gasps, but my words were filled with a kind of stubborn resilience. “I … want to show you…”
“Show me what?”
I swallowed hard. The penetrating glare of his eyes and the mocking laughter from across the room coming from Tamara, seemed to strengthen my resolve. I licked my red lips and boldly stared back at him. I was angry at his smug wife and angry at the game they were forcing me to play. My words seem to come from somewhere beyond myself, because I couldn’t quite believe I was hearing myself say them.
“I’m going to show you what a real whore can do. You say you want a filthy little slut to be the plaything for you and your wife. But in the end you just want to get off, don’t you? You want a girl who knows how to be dirty for you, and not just sip champagne and chaperone your deviant fantasies.”
Tamara’s laughter stopped, but Conrad’s eyes flashed with renewed desire.
“You’re a feisty one. I like that. So why doesn’t my little slut get down to business… and put her mouth to work for her money.”
His put the palm of his hand against my pelvis and ran it deliberately hard up my body, between my breasts in a straight line, and then up against my throat, pausing while I smiled back at him. I felt like I was inviting his challenge, even as they coiled around my neck with a vague kind of menace. His hand slid up to lightly squeeze my cheeks, before I felt his hand atop my head where he pressed down with a consistent force, causing me to instinctively move lower and lower until I was on my knees in front of him.
I was breathing hard now, aware that I was in a sideways position so that Tamara could watch me take care of her husband. I felt myself getting wet in response to seeing that hint of envy in her eyes as she watched me unbutton her husband’s pants and pull them down, along with his boxers. I knew he was hard and his cock sprang free immediately. It was much larger than my boyfriend’s, and gloriously thick with a large knob head that was glistening with pre-cum.
Emboldened by his reaction, I took a moment to smile sweetly at Tamara before engulfing his shaft with my mouth. I had never been watched before, and feeling her eyes on me as I worked her husband’s cock in and out of my mouth turned me on in a way I hadn’t imagined before. I was pleasuring him, and performing for her. And I intended to excel at both. I ran my tongue along the underside of his shaft, swirling around it as my head bobbed up and down. He made no sounds for all my efforts. I was sucking him in just the way that usually had Seth moaning out loud. Crouched down but still balanced on my stilettos I had my hands on either side of his hips to steady myself as I worked his cock. It was glistening wet, large and pulsing in my mouth as I tried to take as much of it in as I could without gagging. With one eye I glanced at his wife who was smiling smugly and continuing to sip champagne as though she was watching a show at the theatre. My eyes lifted to look up at his face for approval as I quickened my pace, sliding his thick cock in and out of my mouth, up to the mushroom bulb and then back down again.
“Fuck, but you do look beautiful down there,” Conrad said as my eyes met his. “How does my cock taste to my dirty little slut. I know you’re sucking me hard for all that money. Do you think you can make me cum?”
I moaned my response, not wanting to let up. I could feel him pulsing in my mouth. He had to be getting closer. But the longer I went on, the more I realized he had complete control over his own pleasure.
“I think for $15,000, I need to get my money’s worth, don’t you?”
“Yessss,” I gurgled
I felt him seize my ponytail and steady my movements.
“Now I’m going to show you how I like it,” he said in a matter of fact way.
He wrapped the length of my long blonde ponytail like a rope around his wrist, and pressed forward, hard until I could feel the bulbous head of his cock against the back of my throat. I tried to resist the urge to gag as he held my head still and pushed on further.
“Come on, take it all in… that’s a good girl. Relax your throat. The best kind of whores can swallow every inch of me. And you want to be an expert don’t you?”
I could feel my eyes watering as I tried to relax my gag reflex, feeling his cock start pushing past the back of my throat. I was helplessly at his mercy and submitting to his demands without question. I kept my eyes on his as he started moving in and out of my mouth first slowly, training his gaze on me as I became used to the depth he was achieving and then maintaining. I could feel my pussy getting wet as he continued to take total control, holding my head by my ponytail while he started to fuck my mouth in and out with steady rhythm.
“That’s it,” he urged. “That’s how a good little whore sucks cock.”
He had both hands on my head, steadying me to his will, driving his cock in and out, past my wet lips while I alternately gasped and fought against the urge to gag as he shoved his cock deeper down my throat; violating my mouth. I could feel the wetness of my saliva and the pre-cum that leaked from the head of his cock every time it hit the back of my throat start dripping from corners of my mouth as he rhythmically fucked my face, driving his hips forward purposefully, knowing I was helpless to resist him.
Finally he pulled my hair back and withdrew from my mouth while I gasped for breath. Breathing hard, I sank to my knees, trying to wipe my mouth as I rested forward on my hands, coughing and sputtering. He stood there looking down at me trying desperately to compose myself.
“I knew she wouldn’t succeed,” Tamara mused finally and I looked over at her with vile contempt as she crossed one long leg over the other and cocked an eyebrow at me. “Looks like you’re not as good of a whore as you might think you are.”
“Her skills are credible,” Conrad noted arrogantly. He walked over to the table where Tamara sat, his erect cock bobbing in front of him, seemingly unaffected by anything that had happened. He took a sip of her champagne before returning to where I was still resting on my hands and knees.
“What to do now to make her earn her keep,” he mused aloud.
I looked at Tamara’s smug face, and a surge of heat flamed through me that seemed to overtake any sense of who I was or what I was capable of.
I crawled towards Conrad who seemed surprised to see me coming back to the challenge unabated and undefeated. Then I worked myself between his legs and lifted my face upwards until my lips found the soft sack of his balls. I licked his balls, massaging them with my tongue before sucking each one inside my mouth gently, moving them back and forth until I was rewarded with a long groan finally elicited from his throat. Encouraged, I spit into my hand to lubricate it, and reached up to start stroking the shaft of his cock in rhythm to the motion of the way I sucked his balls. Conrad spread his legs slightly, giving me more space as he pressed further against my tongue.
I could feel my pussy wet and dripping, and I unabashedly let one hand slip between my legs to tease my clit, feeling my wet folds swelling in response to how absolutely dirty I began to feel about the whole situation. I imagined what Seth might have thought if he could have seen me on my hands and knees in this beautifully expensive hotel, getting paid thousands of dollars fuck a complete stranger. I felt dirty and dark and twisted, and my mind seemed to come alive at the change of image I had undergone. The good girl Alison was somewhere outside that hotel room. The woman on her hands and knees was depraved and raw and primal in her urges, turned on by every violation and still hungry for more.
I leaned forward, licking his balls in long strokes before my tongue slipped over the soft skin of his perineum, which I flicked back and forth with the length of my tongue. I could feel his muscles clench with obvious pleasure. Then, slowly I worked my way forward, sucking and licking until my tongue found the tight puckered star of his asshole. I felt his whole body sigh as I encircled it with my tongue, licking it and reveling in tasting every part of him. I knew he had not been expecting this from me, and from the way he pushed against my probing tongue, I knew I had found his weakness. I didn’t alter the rhythmic stroking of his cock, but let my tongue run in long slides from his balls to his asshole, before probing the little hole that seemed to clench around my tongue. He moaned his pleasure and I couldn’t help but pause and smile wryly.
“You like that don’t you?” I murmured. “I’ll bet your wife doesn’t lick your asshole like I am right now. I’ll bet you need a dirty little whore like me to tongue fuck your ass and make you come. Cause I know she thinks she’s too good for it. But I’ll do it. And now I know you’ll come for me.”
I dove back in, thrusting my tongue up inside his asshole, while he audibly moaned. Perhaps it was in shock at my sudden lewd comments, or perhaps it was from the way my tongue nestled against his muscular ring before pushing past it to tongue fuck his ass without reservation and with utter abandon. He moved in rhythm to my tongue, undulating against it, while I quickened the pace of stroking his long thick shaft. The more resistance I felt, the more I sought to penetrate him, shoving my tongue up as far as it would go and then sliding it back and forth until I could feel his cock jerking in my hand. Quicker still I went, working my tongue in deeply until finally I could feel the wonderful pulsations in my hand and I felt a burst of creamy cum splash my hand and drip deliciously down his shaft. I groaned, almost feeling like I could have come myself from the elated finale to all my efforts to satisfy him. Still on my knees, I brought my tongue around in long strokes, licking at the river of cum dripping down from his balls, tasting it in my mouth while I lapped up the rest from his cock. He tasted warm and salty and for some inexplicable reason, I wanted every last drop from the fruition of my oral labours.
I looked up at him with a smile, my eyes alight with the realization of my success. His face was smeared with obvious satisfaction as he took my chin in his hand, and let his thumb slide into my mouth as I teased him with my open grin. I sucked his finger greedily, letting him know that his whore was not quite finished, and that there was much more to come.
“You are a fantastically dirty little slut,” he said with amazement. “I didn’t know you had it in you. You loved licking my ass didn’t you.”
“I love earning the money you promised me.”
He laughed, realizing he had entirely misjudged me. Indeed, I seemed an entirely different person from the girl I had been earlier that day. This didn’t feel like the Alison I knew. This felt primal and raw, like I was tapping into a part of myself that I hadn’t even imagined existed within me.
I looked to Tamara, who sat poker faced and silent. Obviously she had misjudged me too, and perhaps that was my greatest satisfaction of the evening.
“You’ll get the $15,000,” Conrad said, “and a generous tip on top of that.”
With one hand he reached behind me, and with the end of the belt he had strapped on my waist earlier, he seized me and yanked me to my feet like a rag doll. He drew me closer to him. So close that we were eye to eye and for a moment I thought he might kiss me. I could feel his warm breath on my cheeks, and the predatory way he looked at me immediately had me back at his mercy.
“I think you say you want the money,” he murmured, his eyes locked with mine. “But I think what you want most is for me to fuck you right now… hard and long… until you beg for me to stop. But I won’t. I’ll just fuck you harder. I think that’s the reward you crave most right now.”
I felt immobilized standing in front of him, with the bite of the leather belt digging sharply into my skin. I felt light headed with the moment, with the feeling of being helpless to this man that would easily have his way with me. And there was something in his words that held truth. I wanted it. And I wanted it more than the money.
He must have sensed the truth that had betrayed any resolve I had to claim that I was only there for my payment. His hand slipped between my thighs and I could feel the wetness of my pussy gushing around his fingers almost immediately.
“Look how wet you are… my little slut. Is this what you like? Is this what you were hoping for when you came her tonight?”
I tried to remain silent, but the way he worked my clit elicited an unrestrained moan from deep within my throat. Encouraged, he slid his long fingers up into my pussy, deep and probing, fucking me with them in and out while I struggled to not slump again him from the pleasure of his teasing. The muscles in my thighs quivered as he rubbed against my g-spot with obvious expertise.
“Now how shall I let you come…” he mused.
He withdrew his fingers and brought them up to my face. Without a thought, my mouth opened and he fed me his fingers so that I could lick them clean of all my hot juices. I felt like he had untapped a wholly lusty and uninhibited side of me that felt like an awakening down deep in my core. He drew his fingers out of my mouth and smeared my lips with the remainder of my pussy juices before he crushed his mouth to mine, tasting me in a hotly open and aggressive kiss that had me gasping for breath.
Then with one hand he reached around to yank my long ponytail so hard that my head was thrown back. I moaned again as his mouth slid down my neck to taste and bite the soft flesh before sucking the tender skin of the hollow of my throat.
“Please fuck me,” I gasped in a barely audible whisper.
“What’s that you said?” he asked, although clearly he had heard what I’d spoken.
“Fuck me,” I begged. “You know what I want.”
“I think I like to hear you say it my slut,” he said, pulling my hair taut, as though enjoying prolonging every second of this torment. “How hard shall I fuck you?”
“How hard do you want to fuck me”, I threw back, throwing a look in Tamara’s direction. She was watching us with obvious fascination. I couldn’t tell if she was pleased or angered.
He pulled the loop of the belt tighter making me cry out slightly from the sting it delivered to the soft skin of my belly.
“I could fuck you hard and long, all night. You already know something of my stamina, and rest assured, you will be begging me for mercy long before I would have the desire to stop fucking you. Are you prepared for this? Because for a $15,000 whore like you, I intend to use you for as long as I wish.”
I didn’t have a chance to respond but could only gasp as he clenched his jaw with resolve before slapping my ass hard. I felt the sharp sting like a lick of fire before he roughly turned me around and drew me up hard against him, so that we were both facing Tamara. I couldn’t breathe or move, feeling my fear and uncertainty growing yet again. I had no idea what to expect, and it had me in a heady state of arousal and anxiety.
From our position, I fixed my gaze on his wife, as she watched us with a combination of fascination and revulsion. How would it feel to be her, I wondered momentarily… to watch my husband fuck a much younger, nubile girl while I remained only a distant observer. Perhaps this was her kink, or perhaps this was also her agony.
I felt his cock starting to grow hard again between my legs, seeming to throb there with a life of its own while we stood immobile for Tamara’s inspection.
“Well, my darling,” she said in a tight voice, “I think you should fuck her.” Her mouth curled into a slow twisted grin.
At his wife’s request, Conrad bent me roughly at the waist pushing me down so that I was bracing myself against the edge of the bed. I felt his hands grip my ass roughly squeezing the cheeks so hard I knew he would leave red marks in their wake. I felt another hard slap and I winced at the flash of pain.
“Now what shall I fuck first?” he mused. “This wet pussy or this dirty little ass.”
I drew in my breath. I had never had anal sex before. It was still the holy grail that my boyfriend had always wanted to try. We had tried before, but it had hurt too much. And Conrad was far larger than my boyfriend. I struggled to find my voice.
“No anal”, I choked out. “That wasn’t part of the agreement!”
“Agreement?” he laughed, pausing to work two fingers into my pussy still slick with juices. “Are we still on this agreement? I thought we were past that by now. You’re here to be my dirty little whore. I think we can definitely agree on that. And your reward is $15,000, and for that you must first reward me…”
I contemplated struggling to get up but he had his hand firmly entwined in the noose of the belt that bound me by the waist and left me entirely restrained and forced to submit to whatever deviant desires he wanted to inflict upon me. I glanced at Tamara helplessly but I could see she was enjoying my fear.
Before I could say another word, I felt him slam his cock into my pussy right up to the balls, splitting me wide with a flaming heat that made me cry out as I lurched forward on my hands. He was so much bigger than Seth and I felt my pussy stretch and contract around his thick shaft, accommodating his sudden invasion. From there I was forced to steady myself on my hands as he drew himself almost entirely out of me, only to ram his cock back deeply inside, slamming hard against my cervix and causing me to moan with a kind of pleasured pain I had never experienced before.
“Does that hurt little slut?” Conrad hissed, without sympathy. “Are you the type to enjoy a bit of pain?”
I whimpered feeling him again thrusting viciously inside of me, until I felt light headed from his efforts to subdue and use me as his paid fuck doll. And the more I considered this unexpected reality of the situation, the more I felt the heat of this raw and degrading moment arouse and excite a part of me I still could not grasp or understand.
Determined, I rose up on my hands, curving my spine so that my ass was up high against his groin. I could feel his cock throbbing inside me as I moved against him, grinding against him and no longer able to contain the moans of pleasure at feeling him fill me up so completely.
“You love being my little slut, don’t you,” he mused, clearly enjoying my sudden changes in temperament.
“Yesss,” I moaned, finally feeling broken by my own raw desires.
From there, he started to pound my pussy, harder and harder, with a ferocity I had never experienced before. The pain and pleasure was searing and intoxicating. My pussy contracted in delicious spasms around his invading shaft as he rocked me forward. The only way I could maintain any balance was to rely on the intense clawing grip of his hands on my slender hips. He fucked me wildly, like an unrestrained animal. I could hear the audible slaps of his hips against my ass, and the rhythmic sounds of his thrusts and groans creating a dirty interplay with my every lustful sob.
I looked to Tamara, trying to focus through the heady and intoxicating state of our carnality. She was sitting back in her chair, her legs uncrossed. Her black dress was open wide at the long slid and I saw her watching us with fixation as her hand rubbed against her exposed clit, perversely enjoying the show we were providing. I could hear her soft moans and noticed her eyes become glassy and unfocused as she reveled in watching her husband fucking me with renewed ferocity.
Again, another hard slap to my ass, and I cried out from the intense lick of pain that sent me reeling forward. His hands clawed into my ass cheeks, spreading them apart as I felt him spit lewdly against my asshole. I clenched up, knowing his intentions immediately. I was helpless to stop him, even though I knew the darker side of me didn’t want him to stop at all.
Conrad pulled out abruptly and suddenly I felt his fingers sliding into my raw, freshly fucked pussy. He slid them in and out, until they were dripping wet and then smeared my tight little asshole with my juices. My body shuddered as I felt a finger start pushing against the muscular little ring that instinctively sought to keep him out. I let out a long sigh as I forced myself to relax around his probing digit, pushing back against him while he slid his finger in up to the knuckle.
“Nice and tight,” he mused. “Just the way I knew you would be. Tell me Alison, have you ever been fucked in the ass before?”
“Noooo,” I whimpered, trying to think of anything other than what he was doing.
“Ah,” he sighed as he started to slowly finger fuck me. “Then you’re in for a treat.”
I felt him slide his cock back into my pussy, thrusting several times, until he was covered in my juices once again. And then, finally, I felt the hard knob of his cock press against my virgin asshole. I held my breath as he pushed against it, uncertain as to what to do.
“Come on Alison,” he murmured under his breath. “Relax and enjoy this the way I know you will”.
He reached an arm around until his fingers were against my clit, teasing it expertly until all I was aroused and excited again. I moaned as he circled my clit, rolling it between his fingers, until I could feel the gush of juices begin again between my thighs. Once he had me distracted in my state of pleasure, he pushed his cock against my asshole once again, this time more forcefully. I gasped as he worked past the resistant little ring until the entire knob of his cock was inside me. I was breathing hard, as he continued to play with my clit as he slowly worked the entire length of his shaft deeply inside my ass. It was a heady combination of pleasure and pain, and I clenched my toes as I sought to accommodate the full length and girth of his cock. He paused for a moment, listening to my heavy breathing and moans, until finally they began to subside. I had been opened wide and the sensations began to change to a kind of tight white heat that suddenly had every muscle in my body relaxing and ultimately submitting to him once again.
“How does that feel Alison?” he whispered hotly into my ear.
“It feels good,” I groaned. “Oh god, it feels so good.”
“Now are you ready to really let me fuck your ass? Are you ready for more pleasure, my dirty little slut?”
“Yes”, I sobbed. “Please fuck me. I want you to fuck me hard.”
I was so turned on and horny for him to continue that I could feel the wetness from my pussy glazing my inner thighs. I replaced his fingers with my own against my clit, while he hand reached again to rake the cheeks of my ass as he began to thrust in and out of me, slowly building to a fast, sharp rhythm that had me moaning loudly. I continued to rub my clit, thrusting back against him at every turn, deepening the penetration that seemed to split my ass wide open in an overwhelming kind of intense pleasure that I had never experienced before.
“Fuck me harder,” I urged him, as I slid two fingers into my dripping pussy and rolled my clit with my thumb. I felt so full, so used, and so beautifully violated all at the same time. He was like an animal inside me, pumping his cock in and out of my ass with primal energy. I felt him grab my long ponytail, pulling it back as he continued to fuck me, making me moan louder.
“Oh yesss,” I could hear Tamara cry. “Fuck that little slut.”
I could see the blurry vision of her in the chaise, legs splayed wide, frantically rubbing her own clit as she watched her husband fucking my ass with his raging cock. The sight of her, head throw back, red lips open wide as she neared her orgasm, combined with the intense thrusting into my tight little hole, sent me into waves of ecstasy. I groaned loudly, my primal sounds mingling with hers, as we both seemed to come within moments of each other. My whole body shuddered in a long blinding white orgasm that rocked me to the core. I could feel my asshole contracting in spasms around his cock and this seemed to set him off because after several intense sharp thrusts, Conrad let out a long groan and slammed his cock in deep. I could feel the wild pulsations as he filled my ass with his hot cum.
Finally after a long chorus or moans and the sighs of the aftermath of our climaxes, he slowly withdrew. I could feel the remains of his cum dripping from my asshole, as I struggled to catch my breath. He let me fall against the white Frette sheets on the bed. I slid against them, deliciously conflicted in the feelings of having just been a paid fuck doll. I felt dirty and carnal and an entirely different Alison than the one that had arrived at his room earlier that night.
Not knowing what came next, I was surprised when he crossed the room to where Tamara sat in her heady afterglow. He took a sip of champagne before leaning in to kiss her passionately, as though he had just been fucking her and not me. I lay there dumbfounded, filled with his cum, both holes rubbed raw, jaw aching. They exchanged loving words in German and Tamara stroked his cheek as though to congratulate him on a brilliant performance.
Finally, Conrad turned to me and smiled.
“Thank you Alison for being my little whore this evening. But I’m afraid it’s time for you to go. I’ve enjoyed using you tonight, and I notice the pleasure has not been all mine”.
I blushed at his words, not having wanted him to know I had enjoyed it at all. The truth was, he and his wife were a sick and twisted pair. They were the true deviants, not me. I thought of my boyfriend Seth, and the aftermath of what I had just done started to sink in. The reality of it all overwhelmed me. I had truly been a dirty whore. A dirty paid whore. I was no longer the girl I had imagined myself to be.
Ashamed, I quickly put on my clothes while they watched. I couldn’t decide if I was humiliated by my decisions that night or intrigued by all the other possibilities I had not yet considered.
I stood there uncertainly with my legs shaking, while Conrad counted out the money I had been promised. In the end, he gave me $17,000 in a small clear bag that I could barely stuff into my purse. All the while I could feel his cum still dripping from my asshole, making me feel even more debased than I would have otherwise.
“Well earned.” He said with a nod. “You are indeed a natural slut. You had me surprised.”
“I’m… not a slut.” I said finally, feeling used and degraded by his smug attitude. “This was a one time thing. I needed the money for school and for living expenses and…”
“Don’t hide behind your weak excuses Alison,” he interrupted sharply. “You’re a whore. Accept it.”
An unexpected rage flamed through my face. “And you and your wife are a vile, egomaniacal couple. I don’t know the reasoning behind your sadistic little kinks here, but before you judge someone else, I suggest you look at your own deviant little world first.”
I grabbed my bag, biting my tongue before I hurled all the other insults and accusations that I had been keeping in check all night. The return to who I was, and to my own complacent universe filled me with a kind of trepidation. The truth was, this entire dark night had just been a moment in time. Tomorrow morning, I would wake up and pretend it never happened. I would use the money wisely, and wipe this memory from my conscience forever. I was not the kind of girl they thought I was. I was not a whore.
My heels clacked loudly on the floor as I walked quickly and purposefully towards the elevator, my spine pulled straight back in defiance to all their ugly insinuations. I pushed frantically at the elevator buttons, desperate to get out of that space.
“Oh Alison?” I heard Conrad call.
I paused and turned back to see him standing in the doorway, very much the way he had been when the dark fantasy gates to room 2412 had first opened to me. He smiled at me with a twisted kind of amusement and predatory satisfaction.
“Can I see you again?”
Carnal instinct ensured that I knew the answer to his question before it ever left my lips.
“Absolutely.”
The elevator doors opened, ready to take me down.
*** The End ***
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