I had always felt comfortable when around other guys. Secure in my sexuality, I knew I was only into women. Confident with my body and size, I had never been embarrassed in the locker room or when changing around guys. I kept myself in good shape: decent six-pack abs, toned arms … and a 7″ cock with just the right amount of girth. I kept my pubes shaved close to make it look even bigger.
So it almost goes without saying that moving into the guy’s dorm, at the start of my freshman year of college, was an easy transition.
My roommate Adam and I hit it off right away. He was attractive, outgoing, and girl-crazy; thus, we had a lot in common right off the bat. The dorm rooms were small and privacy was non-existent, so out of necessity we got to know each other pretty quickly. In fact, sometimes when one of us was with a girl in our room, the other would stay and just fake sleep. We were somehow able to pull this off with the help of the dorm room’s bunk beds. Adam was on the bottom bunk and I had the top. There were plenty of nights during which I faked sleep while listening to him fuck some drunk co-ed on the bunk below me, and vice versa. It was definitely an open secret that the one not getting laid was jerking off to the action; something about which neither of us – though we might have smiled slightly – ever spoke.
We’d even developed a little bit of a routine on the nights when neither had gotten lucky. Returning to our dorm in the evening, drunk, horny, and without girls, we’d have a stroke session together. We’d just chill, lounge around naked in the room, watch porn, and jerk ourselves off. We never mentioned it when we were sober, nor even while drunk; yet still we found ourselves jerking off together at least once a week. The unspoken cue was when one of us started surfing the net for porn. The other would then sit down next to him, and we’d both watch the action, talking about the girls, what we liked, and what we wanted to do. Eventually our cocks would get hard and we’d jerk ourselves to sleep. Things went on like this for four years with not even a hint of more happening. We parted ways after graduation: I left for grad school in Boston, and Adam left to do the same in Chicago.
About six months after the start of grad school I found some time off, so I flew out to Chicago to chill with Adam. He’d mentioned that he was doing well with the girls out there, and so I was looking forward to seeing what kind of damage I could do in a new city. After I dropped my bag off at his new apartment, we immediately went out to hit the bars. We drank hard and settled in to have a great time.
As the night went on, I found myself on a barstool off to one end of the bar, enjoying a flirty conversation with a very sexy woman named Jane. At thirty years old, she was about eight years older than Adam and me and still as sexy as ever. She had all of the requisite curves and good looks, yet she also had a level of confidence and self-awareness that I hadn’t seen in the college-aged girls I was used to picking up. Adam sat a few people down the bar from us, chatting it up with a younger girl named Lauren. She looked smoking hot, was still in college, and was enamored with Adam. So far things were looking perfect for my first night in Chicago.
Unfortunately, Lauren seemed a little too into Adam. He found that he had somehow flirted his way past the ‘late night bar fuck’ category and into the ‘potential boyfriend’ category; so when it came time to go back to his apartment she bailed at the last minute, deciding to go home instead, acting like a good girl and not sleeping with him on the first night. She sauntered off into her cab, and Jane and I … and a dejected Adam got into another.
Too drunk to bother trying to hide his disappointment, he muttered, “I can’t fucking believe that just happened,” as we drove away.
Jane laughingly said, “I thought you had it.” She shook her head, smiling at her new friend’s misery. Then she said it … “I guess I’ll just have to work overtime tonight.” Her words just hung there in the air.
Had she really just said what I thought she said? I thought to myself. Was it a joke or … had she just offered us a … threesome?
The cab got us to Adam’s apartment without much fanfare, during which neither Adam nor I attempted to clarify or probe into what Jane had said … though clearly we both had heard her. As the three of us rode up in the elevator I felt uncharacteristically nervous. This situation just felt different, and I had a sneaking feeling that Adam and I would both be getting laid tonight, after all.
Once we were inside his apartment, Adam proceeded to the kitchen to make us all some vodka tonics while I chose some music and put it on. Jane followed me into the living room, sat down on the couch, and took off her heels. Adam returned with the drinks and we all clinked our glasses together. One round of drinks turned into three … and now we were all good and drunk again, yet a strange sort of awkwardness hung in the air. Jane had not mentioned anything further so I was beginning to think she had been joking about ‘working overtime’.
Of course she had been … she must have been….
Adam excused himself to use the bathroom, leaving Jane and me alone together. The bathroom was at the other end of the apartment, far enough away so that we had a little bit of privacy. I quickly made my move on Jane and soon we were making out on the couch. I figured Adam would see us as he returned from the bathroom and might just go off into his room so I could fuck Jane on his couch. He had been gone long enough, so at first it seemed like he had been thinking along the same lines … until I heard him put his glass down on the table. I had been too busy kissing Jane to even notice that he’d returned. So there we were: Jane and me on the couch, still sitting but intertwined in an embrace, and Adam who leaned a little unsteadily against the wall about five feet away.
Through a vodka fog, I watched Jane twist easily in my embrace and wave him over, at which point he seemed to just float toward us. She reached for his hand and guided him down, pulling him close so she could passionately kiss him. She wrapped her left hand around his arm, while her right still rubbed my leg. Tilting her head, she pulled away from him, saying sweetly, “Bedroom?” This, she knew, was a question that didn’t need an answer.
All three of us got up from the couch and moved to his room. Adam walked over to the far side of the bed and then looked over at me. I nodded. As if on cue, all three of us began to undress. Jane was beautiful, and somehow even more confident, naked, than she had been during our flirtation at the bar. We were putty in her hands, and she knew it.
The next thing I knew, the three of us were laying on the bed together and things had taken on a playful tone. This was, after all, not some hardcore, double-penetration porn scenario. This was three drunk people having a very fun time. Adam sat with his back leaning up against the headboard and watched Jane crawl toward him. She knelt in-between his legs and, gently grasping his already hard cock in her right hand, immediately began to suck it. Adam was in heaven! She seemed to know exactly what she was doing. I knelt next to her and slid my right hand between her legs, gently rubbing her clit and fingering her. Each time I pressed on her clit she moaned, the sound muffled somewhat by Adam’s cock.
Without taking her mouth off of him, she reached over to me and gently guided me further up the bed. Now Adam lay flat on his back, and I knelt next to him. Our cocks were only about a foot apart and Jane expertly alternated between us, using her left hand to jerk Adam off while she sucked me. Then she moved her head down and sucked him while using her right hand to squeeze and stroke my balls.
I really wanted to taste her, so I gently but firmly peeled her off of Adam’s cock. I rolled her onto her back, lay down between her legs and started to go to town, licking her clit and fingering her, my efforts succeeding in making her extremely wet and vocal. I looked up to see Adam standing next to the bed, feeding her his cock while playing with her tits. The sight was exquisite, so erotic. I tongue-fucked her until her thighs ran slick with her juices and my saliva, and she began to close them around my head. I felt one hand reach down between her thighs and grab a handful of my hair for leverage, to grind her pussy deeper onto my face. Her juices ran down my nose and spread across my cheeks, dribbling down my chin … as she began quiver. She’d stopped sucking Adam, because her moans came out loader and clearer, then suddenly let out a scream and arched her back. Instantly, she pushed me away from her pulsing and too-sensitive clit. I crawled up to her and kissed her passionately, letting her taste the result of all of that hard work.
For recovery time, all Jane needed was a pause lasting the span of a couple of deep breaths. Within seconds she was ready to resume the fun. She bounced up off the bed with enthusiasm and purpose, guiding Adam and then me into position, laying side by side on our backs with our legs hanging off the bed. She knelt on the floor and began to eagerly suck both of our cocks again, this time deep-throating us with tons of drool coating our cocks, moving her mouth from one to the other and using both hands to jerk us off. She had us in total euphoria, moaning in brainless ecstasy.
Suddenly she stopped and climbed back onto the bed. Glistening with sweat, saliva, and cum, she lay on her back and motioned for Adam to climb on top of her. As soon as he was in place above her, she raised her legs up and placed her ankles on his shoulders, then used her left hand to guide him into her, while her right hand firmly grasped his ass cheek to press him deeper. Her pussy swallowed him instantly, and soon he was furiously pumping away, fucking her as hard as he could. She was taking it like a champion, and I watched him pump in and out of her until it drove me to the edge. I needed to somehow get in on the action, so I stood next to the bed by Jane’s head and placed my cock near her sweaty, bobbing face. My cock dripped a steady ooze of pre-cum from the tip and Jane opened her lips, her tongue snaking out to gobble it up. Adam seemed close to cumming; a sheen of sweat was now visible all over his body. I stood mesmerized by the sight, wondering if I too was going to get a chance to fuck her. I was close to cumming … I wasn’t going to last much longer.
Jane reached her right hand around me and planted it on my ass, pulling me closer to her and deeper into her hot wet mouth, bobbing up and down from Adam’s thrusts. She then reached up with her left hand and wrapped it around Adam’s neck to pull his face down toward hers. She was pulling him down closer and closer to my cock! I suddenly became apprehensive, but the urge to let it happen became overwhelming. She had his face all the way down to hers when suddenly she freed my cock from her mouth, and firmly grabbed hold of it. She began to deeply kiss Adam, holding my dick just an inch or two away from their mouths. All of a sudden I desperately wanted to have a ‘bi’ experience. My heart began to race as waves of nervous heat cascaded through me: I didn’t want to read this situation wrong and ruin everything. And I definitely didn’t want to make the first move. I prayed that neither of them would make eye-contact with me, looking to me for direction. Seconds seemed to last forever. Their kiss went on for what seemed like an eternity. Jane held tightly to my cock, forcing me to be within inches of their deep kiss.
When she finally pulled away from Adam just enough to create some breathing room, her left hand guided the back of his head while her right held my shaft in a death grip. His head moved toward me … and I moved toward him. She leaned in so that her lips, Adam’s lips, and my cock all converged at the very same moment. They played and flicked with each other’s tongues, with my cock in the middle. I could hardly believe it when Adam’s tongue actually touched my dick … and I hoped he wouldn’t look up, still scared to let on that I was enjoying this … or that I even wanted it.
Then it happened. Jane gradually pulled her head away, and guided my cock in between Adam’s parted lips. There was no pretending that this was incidental contact, and I felt my cock slide in deeper and then out, stroking inside his accepting mouth as his lips closed around my shaft. He had stopped fucking Jane, and just rested inside her while he focused on his new adventure. Jane looked up at me with a huge smile of satisfaction and enjoyment, and began to whisper words of encouragement to both of us.
“This is so fucking hot,” she murmured softly. “This is so sexy.”
Very quickly it was more than I could take. The nervousness, excitement and pleasure caught up with me and I was going to cum in about two seconds. I had no idea what to do: should I just cum in Adam’s mouth, or should I say something? Awkwardly I stuttered, “Uh … I … I’m gonna cum!”
Upon hearing me Adam hesitated for a second too long, so his mouth was still wrapped around my cock when my first spurt of cum blasted out. But he pulled away fast enough after that so the next blast flew between him and Jane. She quickly pulled the head of my cock into her mouth and began to suck the remaining spurts out of me. My knees went weak from the intensity of my orgasm. I looked down anxiously but couldn’t tell if Adam had swallowed or not, nor if he was pissed off … yet his face remained just inches from my cock which was still jerking from the aftershocks, buried deep down Jane’s throat. He was there of his own free will now, no longer guided or held there by Jane. She had swallowed most of my cum, but let some dribble all over her lips, and then leaned in to kiss Adam again. I could see my sticky cum mixing in with their sloppy kiss.
Instantly, Adam began to pump ferociously into Jane again. He fucked her as hard as he could and I could tell he was ready to cum. Suddenly I had an urge to touch his cock; I had never touched a dick other than my own before, but now the urge was overwhelming and this was my chance. As he ferociously pumped into her I reached behind him, between his legs, and began to massage his balls. I played and tugged at them for only about ten seconds or so before he moaned and began to shake, and then suddenly announced his own impending orgasm. He pulled out of Jane and before he’d even had a chance to grab his own dick I reached out and grabbed him, pumping his cock as he screamed his orgasm and shot load after load all over Jane. I felt his cock throb in my hand. Hot cum dripped off of my fingers; it felt fantastic! Exhausted and spent, the three of us collapsed onto the bed and lay there for a little while … in silence.
It seemed as though Adam and I were still too scared to make eye contact, so I felt a little relieved when he sprang up from the bed and said he was going to go and make us each another drink.
As he left the room I grabbed a towel off of the back of his door and gave it to Jane, who smiled mischievously and thanked me; somehow this just lightened up the whole mood. I felt at ease again, sitting there naked, talking with her and listening to her light laughter that seemed to instantly disarm any inhibition.
“That was crazy!” Trying to express how I felt, this was all that came out of my mouth.
“Crazy hot!” she replied.
“I have never touched a guy like that,” I confessed. “I’m pretty sure that was Adam’s first as well.” I suddenly started to wonder if it really was his first.
“Did you like it?”
I smiled and just gave her a simple, “Yes.”
Adam entered the room, still naked, holding our three stiff drinks. I could sense his nervousness. We all lay around for a while, talking about nothing, drinking … recovering. It was nice to feel so comfortable and free. The conversation eventually touched on the fun we had all just had, and both Adam and I admitted to loving every second of it. We even told Jane about how we used to jerk off together while watching porn in our dorm room. She was amazed we’d never taken things any further.
Light caresses eventually became heavy petting, and soon the three of us were intertwined and going at it again. Only this time there was a sense that everything was out on the table … and this time I was not hesitant, at all, to touch or to be touched. Once, as Adam lay on his back with his legs spread, I seized the opportunity to suck my first cock. I quickly positioned myself between his legs, wrapped my hand around his shaft, and guided the head of his cock into my mouth. I’m not certain I was any good at it, but I definitely enjoyed having him in my mouth. His moans indicated he was enjoying it as well. I reached underneath so I could gently caress his balls while my mouth worked over the head of his cock. Jane made her way down to me, and soon we were taking turns: she deep throated him while I sucked and licked his balls, then she licked her way down to me and I headed up and started sucking his cock again.
He seemed to be having way too much fun so I playfully announced, “My turn!” and traded spots with him. Now it was my turn to just lay back, in heaven, and be on the receiving end of all of the lavish attention. It was amazing! I closed my eyes and savored the difference between Adam’s and Jane’s alternating sucking: her experienced and enthusiastic laving and suckling, followed by the taboo excitement of Adam’s eager mouth sucking me off.
Eventually Jane climbed on top and straddled me. She grabbed my saliva-soaked cock in her right hand and held it straight up, guiding it into her pussy. Slowly she lowered herself down onto the full length. There is nothing quite as welcoming as the feeling of the inside of a receptive woman. Jane’s pussy was extremely wet, and scorching hot. Her juices instantly coated my shaft, and it was clear that she was in no mood to play around. She moved as if in a sex-fueled trance. Needing desperately to cum, she bounced up and down on me, with her eyes closed and a very sexy look of concentration on her face. She reached back to pull Adam closer, grabbing the back of his head and kissing him deeply. He began to lightly pinch and tug at her nipples. Her moans grew louder, and she stopped bouncing up and down on me, instead grinding back and forth. I felt my raging cock swirl around inside of her as she ground her clit along my pubic bone. She seemed able to withhold her orgasm, at the point of almost exploding, prolonging her enjoyment. Adam suddenly pulled his body up alongside mine, and then farther up so his cock was in line with my face. With his left hand, he guided his erection toward my mouth; I opened eagerly and he slid himself right in.
It was almost impossible to keep from cumming immediately: there I lay, with Jane grinding away on top of me, my hands firmly planted on her ass cheeks forcing our bodies together, while Adam fed me his cock. Occasionally, he pulled himself out of my mouth only to put his balls where his cock used to be, and have me suck on them. Jane pressed two of her fingers to her clit and very quickly began to crescendo in enjoyment. I felt the spasms began to roll through her body as her cum dripped copiously down onto my thighs. She screamed, panted, and convulsed in the throes of what was probably the most intense orgasm I had ever seen.
As her climax subsided she climbed off of me, her pussy too sensitive to be touched. Soon she re-focused, and turned back to Adam and me with a renewed sense of purpose. Adam was still using my mouth to alternate sucking his cock and balls and I could tell he too was desperate for release. His erection had seemed to grow and harden even more within just the last minute. I tasted the first drops of his pre-cum as Jane walked up behind him and started to run her hands all over his body. Slowly she slowly lowered herself onto her knees, kissing her way down his back and eventually licking along his ass cheeks and tonguing his ass crack. Her ministrations forced him to bend toward me slightly. Soon she was rimming his ass and had Adam moaning like an internet porn star. She dribbled spit into his rear entrance and tongue-fucked deeper and deeper into his puckered hole. His moans turned to deep groans, and I had to stop sucking him for a few seconds just so I could enjoy the sight as she worked over his asshole. I watched her slide one finger up and deep into Adam’s ass, at which point he let out some moans of pleasure mixed with sighs of pain, his body taut and his cock rock hard, breathing deeply and bent in half. I adjusted my position to have better access to his jutting cock. When she slid a second finger in, Adam let out even louder gutteral moans, and I took this as my cue to start sucking again. I took his thick hard cock as deep down my throat as I could, listening as his breathing became erratic, then felt his cock swell and the first spurt of cum erupt into my mouth. I concentrated on sucking the head while jerking his saliva-slick shaft with my hand. He twitched and moaned and even screamed in ecstasy, as wave after wave of cum shot into my mouth. Finally, still shaking but unable to handle being sucked anymore, he pulled his cock out of my mouth.
I had a mouth full of cum and no idea what to do…. Suddenly, I reached over and pulled Jane toward my face, planting a sloppy, cum-filled kiss on her. She loved it, and we aggressively made out, coating ourselves with his cum. We both turned to look at Adam, who had flopped on the bed, a look of exhaustion on his face; his intense prostate orgasm had clearly taken its toll.
At this point I was more than ready to take my turn. I hopped off of the bed with more energy than the both of them combined. Jane stood up a little unsteadily, slid a pillow over toward us, and then guided Adam to lie down with his chest on the bed, bent over on his stomach and both feet resting on the floor. In his present state of exhaustion I doubted he could have put up much resistance, though she held him there while she reached over to the nightstand and grabbed the bottle of lube. She poured some on her fingers and then rubbed it into Adam’s ass, adding more and more until she had him drenched in it and her fingers easily slid in and out of him. Thin strands of excess cum leaked from the tip of his cock. With her left hand she reached over to me, pulled me toward them, and massaged liberal amounts of lube all over my cock. Next she guided the tip of it right up to Adam’s waiting asshole.
“Slowly,” she whispered. “Don’t get too excited.” She held my cock just below the head and pressed the tip into Adam’s pucker, very slowly guiding and pushing me in. He moaned weakly. Jane gave him words of encouragement. After some initial resistance, the entire head of my cock was now seated inside of him. She held me there for a minute while she continued to whisper sexy encouragement in Adam’s ear.
Now his ass seemed inviting and yearning to be filled, and I wanted to push harder but Jane was still controlling the pace and the depth. She had me slowly push my aching, rock-hard cock almost all the way into him, and then agonizingly slowly pull almost all of the way out. After a few minutes, she poured on more lube and allowed me to go just slightly faster.
She put her lips directly to my ear, her hot breath invading my brain. “You like fucking that ass?” She whispered. “Did you like sucking his cock tonight?” Her questions brought me to the brink. “Fuck his ass for me. I love how hot this looks! I love seeing your cock inside him.”
Soon her whispers had me over the edge and I could feel my own orgasm start to build. I picked up the pace and within seconds I was shooting the first stream of cum deep into Adam’s ass. My cock throbbed and pulsed as it spit stream after stream of hot cum deep up inside of my friend. When I was sure my balls had completely drained, I slowly pulled myself out of Adam. If he hadn’t been exhausted before this, he sure as hell was now. In fact, all three of us were.
We slipped unsteadily into bed, still nude; only this time we all got under the covers and spooned. Jane was nuzzled comfortably between Adam and me. A few mentions were made of how amazing and how hot everything had been, and Jane repeated how amazing it had been for her and how much she loved being with ‘guys who play together’.
As we all drifted toward sleep, Jane gently brought her sweet lips against my ear. “First thing in the morning, your ass is next,” she whispered, as the three of us quickly fell into a deep sleep.