Jim had passed out at my apartment with my roommate and I, but there was never any sexual tension on my part. After we all graduated, I stayed in touch with Jim. He was relocating to Boston, were I was living and working for the past two years after college. I had a girl friend, but she had a separate place, so I told Jim he could stay with me while he looked for a place of his own.
My girlfriend instantly got along with Jim, and found him very attractive. We spent his first weekend doing the usual site seeing. Afterward, we all decided to go out for drinks. My girlfriend retired early, and after we dropper her off, we decided to continue our bar hopping. By the end of the night Jim and I were both pretty drunk. We returned to the house, and talked some more. I am a very horny drunk, and after so discussion about relationships, and our sex lives, I started to get pretty turned on. I was wishing my girlfriend was over, when Jim interrupted my thoughts. He started to tell me that he had a huge crush on me since our undergraduate days at school together. I remained quiet as he told me about his fixation. He was very apologetic and bashful about it. I wasn’t offended, but fairly confused and surprised. My head was already swimming with alcohol.
He leaned in close to me, our eyes locked. I was semi aware of his proximity; but more concerned with sitting up steady. He kissed me rather suddenly. I was pretty much unmoved. “Is this okay?” he asked me. I muttered something about being drunk. He leaned in and kissed me again. This time more passionately. I had my eyes closed, and it wasn’t until his tongue massaged mine passionately and gently, that I started to notice my cock stirring. It was as intoxicating as the alcohol. I was turned on by the unfamiliarity of his stubble on my face, and the taboo of kissing another man. Yet at the same time, it was comforting, his hands on my neck and face, knowing him for years as a friend, he felt familiar and close. I just sat with my eyes closed, as we continued to kiss. I pulled my shirt over my head, and undid my belt almost automatically. The way that my girlfriend and I had sex regularly started in a similar fashion. Jim followed my lead, and began to undress. I was still drunk and spinning, but I recall us relocating to my bedroom. Once on the bed together, I felt his dick against my thigh. It was strange, and bizarre. I had never seen him naked before, let alone had his erection in full attention rubbing against my leg. I hadn’t ever had another man’s erection pressed against me.
We continued to make out, but he sensed my dislocation. He pulled away from me, and placed his hands on my bare shoulders. “Are you sure you are okay with all of this buddy?” I sort of sobered up somewhat, and realized what had just occurred. I looked at him, and then down at my own crotch. I was at full mast, my cock almost painfully throbbing. He and I were totally naked, his hands were on my flesh, and he mesmerized me, as much as he confused me. I didn’t understand his attraction to me. “I think so,” I replied. I was so horny and wanted to get off, I didn’t care. He asked me if I wanted to sleep with him. “You mean, fuck you?” I asked plainly. He laughed and said, yes, or he could fuck me. “I don’t think I am up to try that one out tonight.” Jim nodded, and said, “Well okay, you can top me tonight buddy.” I fell back onto the mattress while Jim left the room for a moment. I stared at my ceiling fan; it was spinning in my head, and despite the fact that it was not turned on. Jim returned with a bottle of lubricant from his suitcase. “We are gonna need this if I am going to let you fuck me.” I sort of laughed at the notion for a moment. But Jim was already squeezing the bottle, and positioning himself on the bed. He rolled onto his chest, and massaged the lube against his ass. I stroked my cock nervously watching him prepare to have me fuck him. I saw his round tight ass, glossed with the lube, and was instantly even harder. “Just don’t try and rip me in half pal, that’s all I ask. I’m pretty versatile, but give me some time to adjust to you.” I nodded silently, as I kneeled on either side of his back. He smelled amazing. It was like a mix of Polo cologne and vodka. He tasted the same when he was kissing me.
I ran my erection along his ass cheeks, and felt a pulse of excitement run from the tip of my cock head, straight down the base and dissolve like electricity into the rest of me. My nipples were tightening rapidly. His ass was glistening with lubricant. I pressed my cock forward and slide it easily between his cheeks. I groaned quietly, the warmth in his crevice grew as I let my cock glide between the globes of his ass. I was sitting on the backs of my calves, as I massaged his ass cheeks. Kneading his flesh in my palms, I pressed his cheeks together, and pumped my erection between the two warm mounds of flesh. “God, this feels amazing.” I whispered, my cock squishing between the lube of his backside. He squirmed gently as I drove my cock forward. He whispered softly to me, “Go ahead and fuck me, but go easy, okay?”
I repositioned my thrust, awkwardly and carefully. I pointed my dick south, and slide downward into his ass. “Is this okay?” I asked him. “You’re fine,” he answered distantly. I felt the tip of my cock reach his hole. It pressed up against him firmly. His fleshy ass cheeks had all but engulfed most of my shaft. The lubricant was cold, but tingled against my dick. I started to press against his hole, and I felt myself enter slowly. I didn’t rush against him, frightened of hurting him. Jim arched his back slightly, and he pressed his backside upward, allowing my cock to enter him at a better angle. “Oh fuck yeah,” he sighed. I spread my hips wider, and let my crotch bare forward until my ball sack was pressed snugly against his greased up cheeks. The moist sound of skin sliding against skin filled my burning ears. The sides of my face were flushed and I suddenly became aware that I was breathing heavily.
I didn’t imagine that the entry would be so uncomplicated. My girlfriend and I had tried anal sex in the past, but she was never able to allow me to fully enter her. She was too afraid it would hurt, and we abandoned the notion. Jim was different. He felt more substantial. I was almost straddling Jim’s ass with my knees, and needed to steady myself from falling forward onto his back. I placed my hands against his shoulders, leaving smears of lubricant against his warm skin. “Am I hurting you Jim?” I asked nervously. “No, man, no…you feel really fucking good,” he gasped - resting his face against his crossed forearms. I began to massage my lubricated hands into his shoulders. Jim closed his eyes, and let me explore his back. While I rubbed my open palms firmly against his lower back, I began withdrawing my erection. His ass was wrapped around my shaft like a glove, and it wasn’t until I started to withdraw, that I realized the intensity of the sensation. It was pure pleasure. Jim’s insides were caressing my entire cock.
“Oh god, this is fucking amazing,” I muttered in near disbelief. My cock slid back almost completely out of his hole, and while I was withdrawing, my ball sack peeled itself from against his ass cheeks. “You like the way that feels?” He asked, exhaling heavily. Jim rotated his upper body slightly to the left and reached his arms around his sides. His eyes were closed, and he stroked my outer thighs blindly. I placed my hands over his, grabbed his wrists, and used them as an anchor while I slid my entire lower torso forward again. I felt the skin of his hole wrap around my cock tightly as I drove inward again.
“Oh fuck,” he moaned. He clenched his hands into fists, turned his head forward again and his back muscles rippled. I squeezed his wrists softly as I rode down on him. He was grunting from behind clenched teeth, his chin holding his head up against the mattress. “Yeah man,” I moaned as I pumped gently in and out of his ass. I was beside myself. Jim’s toes were curling, and he pulled his wrists from out of my grasp. He clawed for the pillow, and stuffed it under his face, his arms wrapping it tightly. I felt electricity shooting to my toes. Jim was crying out “Oh god, don’t stop, please,” his grunts muffled in the pillow he was clenching tightly out of pleasure. The moans he made were ringing in my head. I was in ecstasy. I continued to ride him, pushing and thrusting, my balls grinding his ass, my cock squishing deeper and deeper into his hot incredible hole. I ran my fingers through his hair, the moisture of his sweat matting it down easily. He was so attractive to me suddenly. I was staring at his shoulder muscles, his arms. Everything about him became erotic in my eyes. I started to let go and just pump and ride his ass.
“Oh god, I’m almost there, I’m gonna cum!” he moaned from behind the fabric of the pillow. I was half aware of his announcement, my erection still probing in and out of his ass. My sweat was dripping onto his back. I wasn’t aware that I had quickened my pace; I was ramming my crotch against his shiny bubbles ass cheeks. My sack drew closer to my body, and I was gasping for air. My thighs began to burn as I pumped in and out. Jim threw his head back and ran his hands along the mattress clawing at the fitted sheet. He let out a sort of hiccupped grunt, and began to whine. His whimpers were timed with the pulses of his orgasm. I continued to ride him, my hands caressing his neck, and sides. We were both slicked with sweat and lube. My erection was on fire, and I thought my cock had almost doubled in size. I was brimming to explode. I didn’t even feel the swell of my orgasm initially. It just happened suddenly, unannounced. I was withdrawing my thrust, when I suddenly jerked my back involuntarily. It hit me in a huge warm wave, over my entire body. As I reentered, the cum began to squirt out of my erection in gushes. I squeezed my eyes shut, hearing my own moans muffled out by the ringing in my head.
When I opened my eyes again, I was gasping for air, collapsed on Jim’s back. Sweat was burning my eyes. He slowly turned over, matching my heaving chest with his own heavy breathing. I immediately reached for his swollen, beat red cock. I don’t know why exactly, I believe I wanted to make certain he had experienced the same sort of release he had just granted me. He feebly pushed my hands away, gasping out to me, “Oh god don’t, please it’s too sensitive. I came so hard.” I ignored his plea, and pumped at his erection. He choked on his own breath, crying out as I milked a few more liquidly streams from his cock, his whole body shaking.
Once I had squeezed his erection dry, I let his cock fall limply on its side. He let his muscles relax slowly, and I watched as the last bits of his orgasm faded. We both just laid next to one another staring at the ceiling fan catching out breath. I broke the silence by apologizing for not lasting very long. Jim turned his head to face me, and replied that it was incredible, and that he was still afraid it wasn’t true. I threw my right arm around his chest, and it fell limply across him. He grunted, surprised by my arm striking his chest. There was no longer any awkwardness. I felt so right next to him. He maneuvered his right arm underneath my head, and rested his hand on my shoulder. “I love you buddy, I was hoping you would like this,” he said.
Sundays had quickly become Carl’s favorite day of the week. Each Sunday morning, as the sun would come pouring through the windows on the east side of his tenth floor apartment, Carl would wake up to find Stan, fast asleep and rolled up in the folds of his thick down comforter. Stan was one of Carl’s students at the university where Carl instructed English courses. The two had met roughly
Patrick was a bartender at a club not far from my work. I had seen him around the neighborhood in the past. He was amazing looking. One evening, after work I stopped in his bar, and was pleased to see him behind the counter. There were only two other men inside, off to the back, talking softly. He motioned me over, and I ordered. He was quick to start conversation, and we hit it off right
Jim is a good friend of mine from college. I had never considered fooling around with him even though I knew he was gay. I had always thought he was attractive; he was brown haired, from Irish descent, green eyed, and pale in complexion. He and I would go to the bars together, since there wasn’t much a gay scene at our University; he was content to drink at the straight bars with myself and
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