“I have never…had a one night stand.”
I lifted my glass and took a drink. Dan and Serena did likewise, smiling as they drank from their large mugs while Erin sat back and watched with a smug expression.
“Okay,” Dan said, wiping his mouth as he set his beer back down on the table. “My turn.” We all turned our attention towards him as he stroked his chin as if trying to think of something to say. “Alright,” he said after a few seconds of contemplation. “I have never…cheated on someone.” I glanced across the table at Serena, who flashed a shameful expression as she took a drink. I followed suit, raising my glass to my lips with a smirk. “Hey,” Dan chided, casting me a scowl as he thumped his fist down onto the table. “You have to take bigger drinks than that.” “Gimme a break,” I answered. “I’m drinking rum and cokes here.” As I was the only one opting for something a little stronger than beer, the effects of our little drinking game were beginning to firmly take hold. Since we had first arrived earlier in the evening, the bar had grown quite crowded with the usually Friday night clientele, raising the ambient volume to an almost uncomfortable level. After a couple casual drinks, Serena had suggested a drinking game to liven things up. The game we were currently playing was once of my favourites, since I always enjoyed peeking into the private sex lives of my female friends. Although the questions had started out innocent enough, the more we drank the more risqué they became. “I have never…” I began thoughtfully as I studied the expectant faces of my companions. “…taken it up the ass.” Erin remained motionless as our eyes all turned on Serena. Giving a simple shrug and smile, she calmly lifted her glass and took a deep drink. “Well, someone’s been a bad girl,” Dan muttered with a smile as he sat back with astonishment as Serena placed her glass back onto the hard, wooden table. Dan wasn’t the only surprised one at the table. Serena had been consistently drinking with every statement made. I had always known my friend to have a relatively liberal view on sexuality, but this drinking game was casting her in a whole new light. Her roommate Erin, who was seated beside her, couldn’t have been more different. She seemed to blush at the mere mention of sex, and was growing increasingly uncomfortable at the direction our little game was taking. “I have never…” Serena began, fixing her eyes on Dan as she spoke. “Slept with a friend’s girlfriend.” Dan took a drink as he shook his head, disappointed at the obvious ploy to single him out. His sexual exploits were well known, making him an easy target in a game such as ours. After Erin took a turn, it was back to Dan, who was eager to even the score. “I have never…” he said with a cocky smirk. “…had a guy cum on my face.” Serena narrowed her eyes in an attempt at forming an ominous visage, but her expression soon softened into a playful smile as she raised he glass to her lips. “Wow,” I exclaimed, as Serena downed the rest of her beer. Dan and I exchanged subtle looks while Erin eyed her friend with a look that could only be construed as disgust. “Ooooh,” Erin shrieked suddenly as a new song came on. “I love this song! Let’s go dance.” “Sure,” Serena agreed, pushing her chair out before looking back at us. “Are you guys going to come?” “I will,” Dan piped in promptly as he finished the rest of his beer. I remained in my seat. “Damon?” Erin asked. “You coming?” I shook my head. “You guys go ahead,” I said with a brush of my hand. “I don’t dance.” Dan and Erin turned to walk away, but Serena hesitated slightly. “Actually…” she said, as Erin turned to acknowledge her. “On second thought, I think I’ll stay here and keep Damon company.” As the pair headed to the dance floor, Serena watched them suspiciously as she sat back down across the table from me. “Does Dan like Erin?” she asked, spinning her empty beer glass on the table. “Is it that obvious?” I returned with a smile. “Yeah, kind of.” I just shrugged as Serena tried to get the attention of waitress wandering by. After ordering a couple more drinks, I decided to press her more concerning the issue of her sordid, sexual history. “So what other naughty little secrets do you have?” I asked, studying her facial expression as her mouth curled into a warm smile. “Wouldn’t you like to know,” she said, hiding her playful expression by taking a drink from her glass. “Ummm, yeah actually. I would.” Serena laughed, though she seemed to be dodging the question. “Well,” she said softly, cocking her head to the side. “What would you like to know?” “Are you going to answer truthfully?” “Depends on the question.” “No,no,no,no,” I objected, shaking my finger. “You have to promise that you’ll answer truthfully.” “Okay, I’ll you what,” Serena muttered, leaning in towards me. “I’ll answer one question for every question I get to ask you?” I pondered her proposal for a moment, before answering. “Deal.” “Alright,” she said with a nod of her head. “You go first.” “How many guys have fucked you in the ass?” “Wow,” she exclaimed with a laugh. “You don’t waste any time, do you?” I just smiled and awaited her response. She looked at me as she shifted in her seat, looking uncomfortable for the first time that night. Serena then held up her hand displaying five fingers. “That’s not too...” I began, before she lifted her other hand, flashing out four more fingers. My smile grew wider as she began to blush, quickly taking another nervous drink of her beer. “And how many of those were repeat performers?” I asked, crossing my arms as I grew more intrigued by my friend’s enticing answer. “Uh uh,” Serena, scolded with a wave of her finger. “My turn.” “Right. Sorry. I forgot.” “Have...you...ever...had a threesome?” “Nope,” I stated flatly. “My turn.” Serena looked disappointed at my answer. “Have you?” “Maybe...,” she answered elusively as I furrowed my brow in mock anger. “Okay, okay. Yes. I have.” “With two guys?” “Yeah.” “Wow,” I exclaimed, picking up my drink and sitting back in my seat. “I’m impressed. I had no idea you were...” “Such a slut?” she snapped, finishing my sentence as she raised her eyebrows and waited for my reply. “Well, that’s not...what I was going to say...but...” I stammered, as she stared into my eyes with a scrutinizing gaze. “It’s okay,” she said, pushing out her bottom lip into a pouting expression. “I am...kind of a slut sometimes.” “Well, aren’t we all?” I said, trying to lighten the mood as I raised my glass in salute. “Yeah,” she agreed. “Although when you screw a bunch of girls, you’re called a stud or a lady’s man. When a woman does it, she’s called a slut or a whore. Not fair really.” “Well, there is a good reason for that so-called double standard,” I replied with a smile, as Serena crossed her arms and stared with interest at what I had to say. “And just what reason is that?” she asked, her voice dripping with scepticism. I took a long, slow drink before setting the glass down and answering. “Because...girls can get laid whenever they want.” “They can not,” she stated bluntly, frowning at my suggestion. “Oh yes, they can,” I insisted. “If you wanted to get laid right now...you could. Women hold all the power when it comes to sex. You could walk up to any guy in here and say ‘want to fuck?’ and you could get laid.” “Oh whatever,” she scoffed with a dismissive wave of her hand. “Guys can get laid whenever they want too!” “Oh no they can’t.” “Yes they can!” “Serena,” I said bluntly, raising my eyebrows as I kept my gaze fixed. “Trust me. If I could be getting laid right now...I would be.” “Oh yeah?” she said with light hearted laugh. “Is my company that bad?” The two of us shared a laugh, followed by a short period of silence before she spoke again. “So are you trying to tell me...” she began, leaning in close as her voice grew softer. “That if a girl came up to you right now and asked you to go home with her...you would say yes?” “Absolutely!” I replied emphatically with thump of my fist into the wooden table. Serena bit her lip, and rolled her eyes as if something was on her mind. She then fixed her eyes back on mine as she spoke. “Okay then,” she said, sliding her glass across the rough wooden surface. “Do you want to fuck?” I was caught off guard by her questions and just stared vacantly in surprise before studying her face for any sign that would tell me that she was joking. “Are you fucking with me?” I asked, my eyes narrowing with suspicion. “No...” she said, sipping from her glass. “But if you take me home right now...I will be soon.” I remained unconvinced, but my suspicion gradually melted away under the intensifying heat of Serena’s sexy stare. “What about Dan and Erin?’ I began, stammering as she continued to watch me with growing amusement. “They’ll be fine. Let’s go.” Two minutes later we were in a cab on route to my apartment. As we rode together in the back seat, I found myself stealing casual glances of Serena as she looked out the window, humming quietly to herself. Although we had been friends for years, we had never even come close to hooking up before. Serena had always been “one of the guys,” preferring the company of male friends to females. She was the kind of girl that you say anything to. Dirty jokes. Rude comments. She just laughed and dished it out as good as she took it. She was attractive, though few would consider her “hot.” At 5’8 she had a thicker, curvy frame with soft, rubenesque features. Her hips and thighs were relatively thick, and although they were far from what most people would consider “fat”, I always got the impression that she possessed a fair amount of self consciousness regarding them. On the other hand, her breasts, which could also be described as thick and curvy, were usually prominently displayed through a tight fitting top or plunging neckline to display her ample cleavage. Her dark brown hair was thick and lustrous, hanging straight down to the level of her mid-back, or down the front of her shoulders depending on how she was wearing it on any given day. Her most definitive features however, were her eyes. Large and doe-like in appearance, Serena’s dark brown orbs seemed to dominate her soft-featured face which also possessed a pair of enticing, full lips that generally portrayed an inviting, friendly smile. As the cab neared my apartment, I found my heart rate begin to quicken. In a mix of anticipation and nervous apprehension, I began to fidget with the coins in my pocket as I played out a dozen different scenarios of how the night`s events may unfold. Usually when Serena and I were together, there was never a lull in the conversation. Whether engaged in witty banter or having a serious conversation, it seemed that we always had something to talk about. At that moment however, I had absolutely no idea what to say. When we reached my apartment building, I paid the cab driver and we headed inside, the awkward silence extending to include the long walk up to the third floor. My mind became a tangle of random thoughts and worries as we gradually approached our destination. Should I kiss her? Would that be too intimate? Would she get offended if I didn’t kiss her? As the questions continued to swirl through my mind, I silently scolded myself for making such a big deal of things. I then decided to relax and let events run their course. “Want something to drink?” I offered, entering my bachelor suite apartment and tossing my keys on the counter. “No thanks,” Serena answered, walking right into the room and heading straight for the bed. She casually removed her shoes and set them by the bed as I strolled over to the stereo to put on some music. When I turned back to her, she was leaning back comfortably on my bed looking around my diminutive apartment. “You need some pictures in here or something,” she suggested casually, as she glanced around at my empty walls. “Yeah,” I agreed, joining her on the bed. “I wasn’t planning on staying here this long.” Serena turned to acknowledge me, smiling as she watched me sitting nervously, unsure of how to proceed. “Geez,” she blurted out in exaggerated exasperation after a few more awkward moments. “You’re going to make me do all the work huh?” Before I could respond, she stood up and moved to stand over me, gazing down with a look of carnal intent. At first I thought she was going to kiss me, but instead Serena gave me a forceful shove, pushing me back onto the bed. I blurted out a surprised laugh as she dropped to her knees and immediately reached out to undo my pants. “What’s the matter?” she teased, noticing my startled expression. Have you run out of dirty questions to ask me?” “Uhhh...Yeah,” I stammered as I lifted my hips to allow her to pull my pants down my legs. “I guess I have.” “Aww,” Serena hummed, pouting her lips into a disappointed expression as she tossed my jeans aside. “And you didn’t even ask me about my favourite thing.” “Favourite thing?” I asked, raising an eyebrow with interest. “What’s that?” She flashed me a smile as she stroked a hand lightly over the growing bulge in my boxers “Sucking dick.” As the words left her smiling lips, Serena tightened her fingers around the smooth material and yanked my underwear down over my hips. As my dick slipped free, she immediately grabbed it up and gave it a few long strokes as it expanded to maximal hardness in her hand. In the years we had been friends, I had begun to deduce that Serena held a particular penchant for fellatio and I had always wondered what it would be like to have my cock in between those soft, pouty lips. For the moment however, I would have to be satisfied with the firm touch of her hand as she tightened her fingers around my shaft, making my swollen head bulge with every squeeze. “Have you ever thought about having me suck your dick?” she asked, as if reading my mind while she gazed upon my hardening cock with a look of transfixed admiration. “Actually...yeah, I have,” I admitted, waiting patiently as my fleshy pole throbbed in the forceful embrace of her hand. My response elicited a smile from Serena’s beaming face as her tightening fingers produced a small drop of precum from the tip of my dick. Seeing the small bead of fluid, she leaned down lapped up the tiny drop with a long, smooth lick of her warm, wet tongue. “So...” she continued, not bothering to avert her gaze from her slowly pumping fist. “When you think about me sucking you...Do you picture me on my knees like this?” “Sometimes,” I answered truthfully. “Mmmm,” she purred, placing her mouth between my legs and enveloping my balls with her soft, welcoming lips. “I love being on my knees.” Serena’s talking was turning me on as much, if not more than her lips and tongue, which began working their way up the underside of my sensitive shaft. “What else do you like?” I asked, prompting her to continue as her soft, wet tongue glided easily up my turgid hilt of my cock. “I like...” she began before pausing to suck my swollen head into her mouth and letting it pop free. “...to suck a dick after it’s been in my pussy.” My mouth fell open in an ecstatic sigh as Serena’s pouty lips slipped down the length of my shaft and she took my dick fully into her mouth for the very first time. Her head rotated slightly from side to side as she worked her mouth up and down my cock. Her fingers were wrapped around the base, slowly stroking upwards to meet her descending lips which were fast covering the length of my pole with a saliva-soaked, glistening sheen. “And I love...” she added emphatically as she let my wet cock slip from her talented mouth. “...cum in mouth.” That particular bit of information brought a renewed smile to my face as Serena went back to working my balls over with her unrelenting, wet tongue as her hand continued stroking my pulsing shaft. I slipped my shirt off, leaving me completely naked as my friend knelt before me, still fully clothed. For the next few minutes, all conversation ceased as she became preoccupied with treating my aching cock to one of the most gratifying blowjobs I have ever received. “Alright,” Serena said finally, lifting her head from shimmering cock with a satisfied smile. “I think I need to get fucked now.” Tearing off her shirt, she climbed onto the bed, lying on her back as she unfastened the buttons on her form fitting jeans. Eager to resume things, I assisted by working her pants down her legs with frantic intent as she unhooked her bra and pushed it aside. Her underwear soon followed, leaving Serena completely naked under me as I climbed into position. She licked her hand and rubbed it over her waiting pussy, lubricating her enticing pink entrance she smiled up at me. I could feel my dick throb with every beat of my heart as I held it firmly in my hand easing forward to pierce her dewy lips. My head slipped easily inside and I gave a couple short, gentle thrusts before driving the length of my shaft up to the base in her dripping wet slit. Serena flashed a grin of approval and urged me onwards by pulling my hips down with her reaching hands. I was amazed by the wetness of her pussy as I immediately began sliding in and out with relative ease. Lowering my body to hers, I grasped one of her cumbersome breasts in my hand and wrapped my lips around the nipple, sucking as I subjected her pussy to a series of deep, hard grinding motions. With my shaft firmly buried in her moaning body, I around to cautiously prod her ass with my eager fingers. Serena let a subtle moan slip out as my fingertip found her tight little knot and began massaging her asshole with constant, enduring pressure. Finding our current position somewhat awkward for anal play, I lifted her legs up and placed them on my shoulders, aligning the back of her thighs against my chest as I butted my hips against her ass and sent my cock thrusting deep inside her. Placing my hand back at her little anal opening, I tested the tightness of her tiny ring with wriggling probes of my busy fingers. “So you’ve had nine different cocks in this ass?” I asked, once again renewing our bout of sexy repartee as I spread her trickling pussy juices over her taut little hole. “Uh huh,” she affirmed, pushing her dark brown hair out of her lust-filled eyes. “Do you want to be number ten?” “Maybe...” I replied, smiling down at her with teasing smirk as I pushed a fingertip past her grasping muscular ring. With my finger working its way into her hot little asshole, I fucked her pussy with short, hard thrusts as she stared up at me with an intense, sexy stare. The savage flash in her eyes appeared to be begging for more and I reciprocated by grabbing her ankles and slamming my hips hard into her juicy hole as my balls slapped lewdly against her tightly clenched ass. She could tell by the look in my eyes that I was heading for climax and she smiled in eager anticipation. “When you cum,” she said, her voice broken into panting gasps under the force of my driving thrusts. “I want it in my mouth.” A few more deep strokes and I could feel the elated, tingling sensation racing through my body as I struggled to hold back the approaching storm. When I knew that I could no longer hold back, I tore my dripping wet cock from Serena’s insatiable hole and scrambled up her body towards her waiting face. Planting one foot on the bed, I straddled her face and guided my throbbing rod into her open mouth just as the first creamy spurts began to shoot forth. Serena clamped her lips down and moaned as I filled her mouth, using my gripping fist to coax every last drop out onto her waiting tongue. As she swallowed down every drop, she kept sucking, torturing my overly sensitive head with tickling swirls of her tongue until I was forced to pull away and fall back onto the bed. I was about to retreat into a state of relaxation, when I saw Serena crawling towards me, her big brown eyes flashing with a look of frenzied desire. “What do you think you’re doing?” she scolded. “We’re not done yet.” “For now we are,” I countered with a smile, gesturing down to my dick, now lying lifeless and flaccid against my thigh. We decided to take a short break and I made a quick trip to the bathroom before grabbing a drink of water from the kitchen. When I returned to the bed, I found Serena laying flat on her back with both hands hard at work between her legs. Noticing me standing there, she smiled as her cheeks grew rosy with mild embarrassment. “Oh, don’t stop on my account,” I said with grin, as I took a sip of water. “I’m enjoying the show.” “Oh really?” she shot back as she clamped her legs tightly together. “Well, I bet you might like it better...” As she spoke, Serena rolled over onto her hands and knees, arching her back seductively. “...like this?” I nodded as she smiled back at me, her face pressed flat against the bed. Her new position emphasized her hourglass-like figure by displaying a thick, round ass framing her glistening wet pussy and asshole. The ample curves of her backside and hips gave way to a relatively slender waist that seemed comparatively sleek as her back arched as it dipped down into the bed. I stepped closer, eyeing the lewd spectacle with amorous captivation. “Is that how you like it?” I asked, feeling my cock pulse into the palm of my hand as I held my growing shaft. “Yes,” she replied, maintaining her lurid pose as I set the glass down and climbed onto the bed. “You like getting fucked from behind?” “Uh huh.” “Is this how you like it...,” I continued, kneeling behind Serena as I reached down and tested the pliability of her luscious ass with a firm but gentle squeeze. “...when you get fucked in the ass?” “Sometimes,” she replied with giggle as I slipped my hand between her legs, feeling her moisture by stroking my fingers down her sweltering, wet slit. I became entranced by the sight before me as I slipped two fingers inside her. Her ample cheeks dipped down to form a deep cleft of smooth dark skin, centered by her tiny pink knot. With every touch of my hand, her alluring little asshole seemed to clench as if beckoning me closer. With my fingers thrust inside her, I used my other hand to peel one of her voluptuous cheeks aside and assailed her puckering hole with an enthusiastic stab of my tongue. Serena sighed with pleasure as my tongue ran laps around her tightly closed ring. With my fingers wet from her pussy, I lubricated my cock before rising up and sliding back into the welcoming embrace of her hot little hole. Once deeply positioned inside Serena’s body, I could feel my dick expand to its full girth once again, urged on by the warm, moist sensation. Gripping her fleshy hips in my hands, I held her firmly and gave her a couple hard, quick thrusts. The sound of our bodies colliding created a loud, sharp smacking sound as each stroke sent reverberating ripples through the ample flesh of her ass. Without pausing, I continued my relentless barrage as each violent thrust provoked a lustful moan from Serena’s gasping mouth. “Stick...your...finger...,” she panted as her body lurched with each forceful stroke of my hips. “...in...my...ass.” I let a dollop of spit fall between her cheeks and I spread the sticky saliva over her puckered hole with firm, rubbing movements of my thumb. With each pass, I pressed a little harder until I felt her muscular ring open up and I slipped into her smooth little tunnel. Serena let out a sigh of blissful release as I twisted my thumb deeper into her ass. With my digit now tightly sheathed in her tiny orifice, I resumed my tumultuous thrusting, driving into her sopping wet cunt with unrestrained fervour. I wiggled my thumb inside her as she engulfed every inch of my dick in her fleshy, wet slot. Over and over I speared her with enthusiastic strokes until I was forced to stop briefly in order to catch my breath. I could feel every beat of her heart as her asshole pulsed around my thumb. As I slipped it out, her tiny hole tightened back up into a perfect little pink knot. We both knew what I was going to do next. As I pulled my dripping wet cock from her thoroughly fucked hole, Serena reached back to rub two fingers over her anus before splitting them apart to provide an ample target for my stabbing pole. I placed my spongy head between her two fingers and pushed. Usually I would proceed in a much slower manner, but in my current state of arousal I found myself unable to restrain myself. Taking advantage of the wet juices covering my cock, I splayed my friend’s asshole open with a forceful thrust and surged inside. “Fuuuucccckkkkk, yessssss!” Serena howled as her ass clamped down around my dick. Feeling her hole tightening around my shaft sent my head reeling as her welcoming ass swallowed up every inch of my sinking cock. I could tell that Serena was accustomed to anal sex by the way she was able to relax and admit my welcomed intrusion. With my length buried inside her, I tightened the muscles in my pubic region, causing my dick to pulse inside her asshole. Wiggling my hips, I did my best to stuff every bit of my throbbing cock into her hungry tunnel, pulling back on her shoulders as he moaned with delight. “Is this how you like it?” I asked, grinding my hips into her supple cheeks. “Yes,” she panted. “I love it. I love it deep in my fucking asshole.” As I began to withdraw, Serena’s clenching hole seemed to be sucking me back in, resisting every inch as I pulled away, gripping my shaft like a vice. “I bet you wish you had another cock in your mouth right now don’t you?” I asked, gritting my teeth as I slipped back in. “Oh fuck yes!” she groaned in response. “I want that so fucking bad. I love getting fucked by two guys at once.” Stuffing my dick back between her cheeks, she pushed back against me in desperation as her insatiable asshole repeatedly swallowed up my plunging length. I increased to the point where I was sliding in and out with the same vigour as if it was her pussy I was fucking. “Oh fuck!!!!!,” she squealed suddenly, pushing back violently as my shaft sank deep into her grasping ring. Her body tensed and shuddered as she screamed her way through a tempestuous climax as her asshole convulsed around my dick. The strength of her muscular contraction almost forced my cock from her spasming anus as I held on and waited for her orgasm to subside. A few more strokes later and I was ready to feed Serena her second helping of cum that night. With frantic desperation, I pulled the tip of my dick from her freshly fucked ass and reached out to grab Serena by the hair. Yanking her head back, I stumbled forward and shoved my cock forward as my fist pumped with unrestrained fury. Her mouth quickly opened and her tongue extended in a lurid display as the thick, white fluid shot forth from my swollen head. The furious pumping of my fist increased to a blinding speed and scattered the creamy load across her open lips in a shower of sticky, white raindrops. Gradually, I decreased my stroking as the last of the cum oozed out onto her outstretched tongue before she licked her lips with a satisfied smile. “Why didn’t we do this years ago?” I asked, lying back in relaxation as Serena began to gather up her clothing. “Well, you never asked,” she answered, pulling her underwear back on. “So...what does this mean?” “What does what mean?” “This. Is this a one-time thing or...” Serena paused for a moment in contemplation before answering. “No,” she replied casually. “I think I’d like to do this again. Why? Is that a problem?” “Not at all,” I said with a satisfied smile. “After all...what’s wrong with a good fuck between friends?” Serena looked at me and raised her eyebrows. “A great fuck between friends,” she corrected. “A great fuck.” The End
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