Senior year I had the biggest crush on Elise. We’d been friends for years. The only problem was her boyfriend, Cyrus. He was taller than me, bigger than me, and cooler than me. But I had one advantage…Elise and I had been friends for years. I’d spent weeks telling her that Cyrus was controlling (which he was), and that she was better off without him. I hid my jealousy well, and she was starting to take heed as New Years’ approached. We had planned a New Years’ party at a hotel with all of our friends. I used my fake ID to buy us all alcohol. I was shocked when Elise called me the afternoon of New Years’ Eve to tell me she’d broken up with Cyrus. I got ready for that party with excitement and hopes for sexual adventures. But Cyrus came to the party.
While everyone had fun, he moped. I felt guilty, knowing that I had a great deal to do with why Elise had dumped him. Even though he didn’t smoke, I took him outside with me for cigarettes all night, and told him it would turn out alright, and that he would probably find someone better. It made me feel less guilty about the fact that at midnight I planned to swoop in and make out with the girl who had been his until ten hours earlier.
The hotel suite had a main room and a bedroom. I was in the main room with a bunch of the people watching the TV as the countdown to midnight started. I looked around for Elise, and realized she was with everyone else in the bedroom. Everyone started counting down, “Ten! Nine!” I got up and started hurrying toward the door. “Eight! Seven! Six!” As I got to the doorway, Cyrus emerged through it and stood in my way. He opened his arms, and I thought I could give him a quick hug and then get to Elise in time. “Five! Four!” I opened my arms to give him a hug, but as we came together, I suddenly became aware that he was trying to kiss me. “Three! Two! One!” I pulled away in shock. “Dude, I’m not that drunk.” was all I could manage to say. By the time I got into the other room, the moment had passed. Frustrated, I went outside for a cigarette.
I stepped out into the cold, winter night and went around the corner of the building into a snowy strip between the building and a line of tall shrubs. I lit my cigarette, confident that the night wasn’t over yet and that my chance with Elise would come. The I heard the door squeak open, and Cyrus stepped around the corner. I instinctively handed him a cigarette and got my lighter out for him to use. He lit the cigarette and said, “It’s getting cold.” I agreed. He said something about how he still couldn’t believe Elise had dumped him, and added, “But I think you’re right. I think it probably is for the best.”
The conversation paused as we both took a long drag from our cigarettes. We exhaled in unison, and through the smoke I saw the glint of his eyes staring at me. As the smoke cleared, I realized that we were staring into each other’s eyes. I wanted to break the gaze. I wanted to look away, but I couldn’t. Deep in the widening black of his eyes, a yearning stared back at me. I saw one half of his lower lip twitch almost sideways, and I edged toward him slightly by discreetly shifting my weight to my other foot. He moved closer to me and it seemed that I was being drawn toward him by some force beyond my will. Soon he was so close that I couldn’t focus on his eyes, but I could feel his breath on my face. His soft and warm lips touched mine, and we both froze. An electric current went through my body, but I was too scared to move.
I couldn’t take my lips off of his, and I couldn’t move them either. We took one last move toward each other, and as our thighs came together, the front of my khakis rubbed against the front of his. Only then did I realize that my pants could barely contain my rock hard erection. But my bulge could feel his, and I knew that he was just as hard as I was. We starting kissing each other, over and over, each one wetter than the one before. His warm mouth and full lips engulfed me, and his breath passed my cheeks. One of his hands reached around to my lower back and held me close as he opened his mouth and I opened mine. Our tongues danced as we gently grinded against each other in slow rhythm, our bulging pants warm with friction and the rush of blood to our genitals. The grinding and kissing increased in intensity. He dropped his cigarette and reached his hand between us, toward my pants. He rubbed my dick through the front of my pants. I was seized by initiative and dropped to my knees. His bulging crotch was directly in front of my face. I kissed the warm bulge and felt it throb. I reached for his zipper as he started to run his fingers through my hair. I could feel his manhood pushing from the inside as my nimble fingers pinched his zipper and started pulling it down. In fits and starts his zipper crunched downwards until it was wide open. I reached my hand toward the narrow opening, and my mouth watered as my fingertips worked their way in and just barely caught the soft sensation of his damp, throbbing boxers. Around the corner, the door squeaked open, and I could hear Elise’s voice saying, “They must have gone out here.” My heart jumped and my entire body went flush, as I jumped to my feet and we each stepped back from each other. Then she and Sarah peeked around the corner. “Hey, everybody is really tired. We’re all getting ready for bed.” “We were just smoking a cigarette,” Cyrus said with remarkable coolness. “We’re just finishing,” I added, but my voice broke a little. We both started toward the door. We walked back to the hotel room without making any eye contact, and I rushed straight to the bathroom. My skin was shaking and my face felt warmer than it had ever been. I breathed heavily. I was thrilled by what had just happened, and I couldn’t believe we hadn’t been caught. They hadn’t noticed that two half cigarettes smoldered on the snow unsmoked, or that Cyrus’ zipper was down, or that my knees were both wet, or the wet spot on the front of my pants where my precum had soaked through. I sighed deeply and stared into the mirror. “What’s happening to me?” I thought.
I pulled myself together and emerged from the hotel bathroom. I decided to put what happened outside into a box that wouldn’t have to touch the rest of my life. Ihad been a weird incident and nothing more, a momentary insanity and it was time to get on with the New Years’ plan of hooking up with Elise. I was going to try to get a sleeping spot next to her, but when I went to the bedroom, she was already nestled in the bed between Sarah and Alaina. They all said goodnight to me as they curled up in their covers. I went into the other room, where a few people were getting comfy on the fold-out couch, grabbed a blanket and a pillow, and found a spot on the floor next to Jake. I took off my shirt, but left my pants on, and I wrapped up and adjusted the pillow. Then someone laid down on the other side of me. It was Cyrus. He fluffed his pillow, then rolled facing away from me. I rolled to my left, away from him, and wrapped up in my blanket. Jake was already sleeping in front of me. Slowly the room went silent, and the deep breathing of sleep filled the air. I was just starting to drift off when I noticed the sound of someone rolling behind me. A moment of stillness passed, and then I felt Cyrus’ large hand on the right side of my butt. He slowly gripped it. I was instantly rock hard and my heart swelled. I was used to being dominant in my sex life with girls, but I didn’t want him to stop so nudged my butt toward him a little. He kept grabbing it firmly, adjusting the position of his hand a little each time to explore it’s shape.
Then he slowly moved his hand up and over my hip, giving my hip bone a little squeeze on the way to the front of my pants. The sound of the blankets rubbing was suspicious, so I cleared my throat a little and at the same time slid back a little into him, sending my hand behind me. As he started to slowly and quietly rub my aching bulge, I felt his penis through his boxers. Only then did I realize he wasn’t wearing pants. His dick was also noticeably bigger than mine. My self-consciousness about this was completely taken over by how hot this was making me. He delicately unbuttoned my pants and slid the zipper down unbearably slowly, one tooth at a time. I was so afraid of making any noise that I didn’t even breathe. I just listened, and looked at Jake to see if he was moving at all.
I cleared my throat again as Cyrus and I worked together to slide my pants down, as I rocked my weight to my knees to lift my hip off of the floor. It was too risky to try to take my pants all the way off, so I knew they’d have to stay around my knees. I was only going to pull my pants down, but Cyrus grabbed my boxers at the hip and tugged them down off of my butt, and I eased my erect penis out of them so that it wouldn’t slap against my stomach when the elastic band on my boxers released it. Before I was even settled, Cyrus put his body against mine. I felt the front of his thighs on the back of mine, his toned stomach on my back, and his pecs against my shoulder-blades. I felt his dick pressing into my left butt cheek. And his hand grabbed my stomach and pressed me into him. I inhaled deeply, then opened my eyes to see Jake in front of me and realized how undeniable our situation would be if we were caught.
I tried to be completely silent and remain absolutely still. His big right hand slid down my stomach and his fingers wrapped around my dick. He started moving his hand up and down my shaft, grazing the bottom edge of my head each time. It felt familiar, not like a girl who just sort of plays with it, but like he knew exactly what to do. It felt so good that it almost tickled, and each time the sensation overwhelmed me, my hips reflexively pulled backward, accidentally thrusting my butt into his crotch. I could feel a wet spot on my cheek where the tip of his dick leaked on me. I could hear his breaking breath quietly in my ear. My stomach started to feel warm as I realized he was a minute or two away from making me cum, when suddenly his hand withdrew from my penis, and edged backward away from me. It was quiet and I wondered what was happening. I heard saliva behind me, and then suddenly his wet fingers were touching my butthole. I freaked out inside. None of this had been planned, and this had gotten dangerous enough. I would have let him jerk me off, and I would have reciprocated, but I was straight and there were a dozen people in the room and this had gone far enough.
I edged away a little, but Jake was asleep right in front of me. Cyrus wet his fingers again and lubed me again. I cleared my throat a little to let him know that I was willing to make noise to stop this. But he must have known that I would never do anything to get us caught, and he coughed slightly louder than I had. It was like he was saying, ‘You’re going to let do this, or I will get you caught.’ We were playing chicken and I knew I would lose. My heart was racing and my face was flush and warm. He placed the tip of his penis directly against my hole. I started to move my arm back to push him away, when I heard a noise. Dan was getting up from his spot on the fold-out couch. I put my arm down and closed my eyes and froze. I couldn’t breathe. I heard Dan put his feet on the floor, stand up, and slowly and drunkenly begin making his way around the edge of the couch. He would have to walk right past our feet to get to the bathroom.
When the risk of getting caught was at its greatest, Cyrus pressed the tip of his penis against my hole with increasing pressure. I couldn’t make any noise or move or do anything. He put his hand on my hip to add pressure, and he started to spread my hole open. Trapped and terrified, my hole seemed to just get wider and wider and wider. It started to hurt a little. Dan walked past our feet and stammered across the room. I thought Cyrus’ penis was going to break me and I bit my lower lip in pain. Just as Dan closed the bathroom door, the head of Cyrus’ dick passed my hole and the rest of it seemed to go in more easily, and I couldn’t stop myself from making a deep guttural sound. He froze and I though he was all the way into me. Suddenly everything was quiet again. Nobody in the room was awake. I heard Dan start peeing. Cyrus’ arm wrapped around me and his big hand pressed against my chest. He slowly edged closer to me and to my amazement his penis kept going deeper and deeper. It actually felt amazing in a way I never thought possible. I felt his abs press against my back and his thighs against mine, and his pubes brushed the top of my butt as he penetrated as far as he could go. His head hit something inside of my that caused intense pleasure, and my hole felt amazing as it spread around the slightly wider base of his dick. Even his pubes tickling the upper part of my crack felt good. He kissed my shoulder, then my neck, and whispered into my ear as quietly as he could, “You good?” “I turned my head to look at him and responded with the only think I could think to say, “Oh, my God.” He kissed the side of my mouth gently, then the toilet flushed.
We both lied back down and remained totally still. Just as Dan passed by our feet and turned away from us toward the couch, I pressed back on Cyrus’s dick and grinded up and then down almost imperceptibly. It felt so good and I leaked a huge amount of precum, almost as though the tip of his penis had pressed it out of me. As Dan got settled, I found that I could pretty quietly arch my back and press my butt to slide down Cyrus’s dick slightly and then back onto it, so that he was actually going in and out of me with each slide about one inch. I could tell he was loving it, because he gripped my side and I could hear him exhaling tensely each time I slid back onto him. After a minute, Dan started snoring.
Cyrus Grabbed me again at the chest and thrust himself deep into me. He kissed my neck gently as he removed himself and then thrust again. Each thrust ended deep inside at a point of incredible pleasure, and he started to speed up quietly. I kept arching my back with each thrust to let him open me as widely as he could. At one point there was a slight slapping sound, so we had to go a little slower. We found a rhythm again, and he slid in and out of me. He leaned in and whispered, “What’s happening?” I turned my head and barely more than mouthed, “You’re fucking me.” He thrust deep and I almost couldn’t stop myself from screaming in pleasure. He slid his hand down to my penis and started rubbing it. It was heavily lubricated by the strings of precum that poured out with each thrust. It felt too good. I suddenly noticed how sweaty we both were and how much we were sliding on each other. We found an amazing rhythm where we could slide in and out pretty quickly but in near total silence. He started having trouble keeping the rhythm and I knew that he was losing control. He was breathing heavily in my ear, and I could tell that I was also getting ready to cum. The feeling started in my legs and stomach, increasing in intensity and guided by the sensations in my asshole, getting nearer and nearer to my penis.
His breathing stopped, he thrust over and over in ways that made no sense as he jerked me fast but shallow. Then he exhaled deeply as he pushed himself deeper into me than he had been before and held himself there. I felt his penis leap inside me, then it did it again, and again. At that moment I pushed back into him as hard as I could and grabbed his leg as my own dick jumped and sprayed cum everywhere, over and over. I could feel that his cum was filling me up as his pulsating dick hit the top of my hole again and again. Then we both relaxed in unison. My penis started to go limp, and his did too. He pulled himself out of me and rolled over. As I pulled my pants back up, I could see that I had shot cum onto the back of Jake’s boxers. It was soaking into a oval-shaped spot on his butt, but he was still sleeping. Cyrus started snoring within a couple of minutes, as his cum leaked out of me into the inside of my pants. I didn’t spend much time pondering the meaning of what had just happened. I had cum too hard and it was too late. Before long, I fell asleep too.
