First Time on New Years

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.