My Hot First Time

My name is Skyler, and I had always been straight, and even did fairly well with the ladies. The first time I ever had sex with another guy, I was 20 years old. I played the drums in a band, and at one of the shows I met a guy named Caleb. He was a senior in high school. He said he really liked our music, and I have to be honest, he was the first guy I was ever attracted to. I got butterflies talking to him in a way I never really did with girls.

Of course I kind of shunned him because of this. I was terrified that my bandmates, or my friends, or even my girlfriend would notice that I wasn’t just talking to Caleb…I was flirting with him. He was medium height, very fit, with brown hair, deep brown eyes and amazing full lips that I couldn’t take my eyes off of. I tried to get away from him as fast as I could, but not before he mentioned that he had taken a lot of pictures of us while we were playing. He gave me his number and said that the band should go to his place and party sometime. I thought about him for days afterward. I admit that I found myself picturing him while I masturbated. I imagined his mouth pressed against mine, clutching him near me, going down on him.

Finally I got up the courage to call him. I really wanted to see him again, and my girlfriend was at work all day. More importantly, I had thought of an excuse I could give everyone for going over to his house…to get the pictures he had taken of the band. I was thrilled when he told me to come over, and gave me directions. I took a shower, and carefully picked out my clothes. I didn’t know that anything would happen, but I knew that deep down I wanted it to. I got in my car and pulled out of my driveway smiling, hoping that before I came home, I would be intimate with Caleb in some way.

When I got to his house, he looked as gorgeous as I remembered. His voice had this way of quivering occasionally that made me so hot. We went into his bedroom and he saved the pictures from his computer onto a flash drive. In the process he showed me some pictures he had of friends of his…incredibly cute girls from his school. We seemed in agreement about which ones were the best looking. Afterward we went down to his basement, which his mother had turned into a guest room. There was a large bed and a couch, and another back room that led off from that.

For two hours we chatted down there. Sometimes standing, other times he would recline on the bed while I sat on the couch. We talked about music, girls, getting in fights. The whole time I regretted wearing blue jeans that were slightly too tight, because hiding my erection was difficult. A couple of times I noticed small wet spots on my pants where the pre-cum had soaked through.

I found myself cold-sweating, and somewhat disappointed that it looked like nothing was going to happen. Then he began to talk about what great parties we could have at his house, since is mother was a nurse who often worked nights. There really was nothing breakable in the basement. He got up and gestured toward the door that led to the back room. “Come check this out,” he said, “this is the best make-out room.” I discretely tucked my boner up under the waist of my pants, pinning it to my stomach, and followed him into the back room. It was a small room with blue walls containing nothing but a dresser and a twin bed. “I bring chicks back here a lot,” he went on, “the bed is really comfy.”

I leaped into the air, pivoting to come down on the bed on my back, and sank right into the incredibly comfortable mattress. “You’re right! This is a wicked comfy bed!” The he said “Check this out.” And he sat down on the bed next to me, and lifted himself up and down a couple of times. “It doesn’t make any noise either.” I was so turned on. I knew this was the moment. My hands were cold and clammy, and my heart was racing out of control. Without thinking, I reached my hand over and placed in top of his thigh. He suddenly stopped, and looked right at me. His deep brown eyes pierced into my soul, and all of the blood in the world rushed into my face. I almost thought I would catch on fire. I wasn’t sure if he was about to punch me or throw me out of his house or what. A breaking “Caleb” was all I was able to get out.

He extended one arm over me to support himself, and leaned in and kissed me. My heart exploded, and my stomach flipped…but it kept on flipping like it was falling down an endless crevasse. I couldn’t breathe. His lips just sat there on mine as if neither one of us wanted it to stop, but neither one of us knew what to do next. I moved my hands up toward his shoulders, and he spun himself around bringing his feet up onto the bed until he was partially on top of me. All this movement broke the kiss, and when he got into position there was a pause as though he wasn’t sure how or whether to start it again.

I leaned my head up to him and kissed him. His mouth felt beautiful as we both began to kiss each other with more confidence. His soft full lips brushed against mine and hung there on the edge for a second before redoubling again in pressure and force. Our mouths began to open and our tongues began to touch a little.

I moved my hands down to the back of his hips and held him to me, wanting to feel the curve of his ass, but unsure how to convince myself to do it. Our mouths opened wide, and for several minutes our tongues danced in unison against each other, his warm breath occasionally sliding past my cheek. I began to realize that my boner was pressing against him, and a tinge of shame swept through me until I realized that I could feel him pressing and pulsating into my thigh. I reached down and clutched at his perfectly curved butt cheeks with my hands, and he placed his hand on my chest. I thought he was going to stop this before it went any further, but when I broke the kiss he reached down and began to pull up on my shirt. I let him lift it over my head and went for his shirt as well.

As we came back together, I could feel his warm smooth body pressing against mine. He wasn’t massively built, but the form of his muscles was so hot. I felt a desire I had never felt before. I noticed that as we were kissing, we were thrusting our hips into each other slightly, and it felt so good I wanted to scream. I began to almost quiver all over, and an unknown force seemed to take over me. I wasn’t in control of myself. Raw urges seemed to fill me from some mysterious source and I began to caress his back and his shoulders, I grabbed at his ass, I placed my palm on the side of his head to hold him in place while I tried to tongue his mouth as deeply as I could.

We were breathing heavily. I found myself reaching down toward his crotch, letting the top of my hand brazenly caress his stomach and brush through his treasure-trail until I reached the button in his pants. He lifted his hips up to give my hand room to maneuver, and held his breath as I unbuttoned and then unzipped his pants. Together we slid them down until they were gone. For a fleeting second, I noticed that his bulging boxers had their own wet stain where he had soaked though.

He reached down to undo my pants, and they slid off. But then as he began kissing me again, he moved off of me to one side and began sliding his hand down my stomach. I got nervous and excited and I almost felt uncontrollably ticklish as he slid his hand into my boxers, found my throbbing dick, and drew it out. As he began to caress it and move his hand around on it, I moaned without meaning to. I lost all control. Before long, I began kissing his neck…biting him, sucking a little. I moved down toward his bulge, kissing his chest, and then his stomach.

I pulled his penis through his boxers, and it was more beautiful than I had imagined. I paused for a moment, breathing gently on his pulsing cock as I held it in my hand, then I put my mouth around the top of it and slid it into my mouth. I was surprised by how hot it felt against the inside of my mouth, and how natural it felt to have him inside my face. His moans practically made me cum in my boxers, and I began to slide up and down on him even faster. He began to hump my face, and my heart raced with increasing speed as I felt the tip of his glistening rock-hard dick sliding back and forth on my lips.

His moans became more intense, and then with heavy draw-out breath laced with total pleasure, he said my name. “Skyler.” I went down on him and took him into my mouth as deep as he would go…all 6.5 inches. I felt him hit the back of my throat, but discovered that this felt good. I pounded my head down on him as his stomach tensed and his hands clutched at the sheets. He began to writhe and moan, his mouth hanging open and repeating my name over and over…slowly at first but with increasing intensity and pitch.

Finally he was repeating my name at a pitch that was almost un-masculine and his voice began to break as though he was losing control. “Skyler, Skyler! Skyler! Skyler! Skyler!” Then he paused and every muscle in his body went tense. His hips arched up off the bed, thrusting his penis deep into my face. It exploded into my mouth, and a load of hot cum seemed to fill it completely. It exploded again, sending a large portion directly down my throat. The next explosion came with such force that I choked a little and some leaked out of my mouth onto his stomach.

My reflexes told me to take my mouth off of him, but an unknown force made me engage my mouth completely around him and suck all the harder, begging for more. His dick exploded into my face several more times, and I swallowed every bit. When he stopped, I pulled back, noticed some had stuck to my chin, and as he looked down at me grinning with pleasure but a bit sheepish that he had just enjoyed head from a guy so much, I used my finger to put that bit into my mouth as well. He laughed.

“What now?” he asked. “Roll over.” As he rolled over and came up to the doggy position, I slid his boxers off, and slid mine down as well. I licked his tight, winking hole several times, and then moved to put my already dripping penis into it. It took some maneuvering, but I slowly pressed my dick into that spot until it swallowed my head. I pushed in deep and he moaned as a rested my chest against his back. There was a long pause. “Caleb?” “You feel really warm,” he answered. “You do,too.” I began to fuck him.

He was so tight that I felt like I must be hurting him, but he began to push back into me. After a few minutes of this, he said, “Hold on.” and pulled himself away. I popped out of his hot ass, and he rolled onto his back and lifted his legs up. I slid into him again, and both of us moaned. I thrusted into him repeatedly, kissing his mouth, staring into his eyes, totally disbelieving that this was happening. I suddenly noticed how sweaty we had both become, as I slid with increasing speed in his tight little hole.

Then, without any warning he looked up at me, deep into my eyes. It felt like my penis was struggling to hold itself in, like it had never been so hard. I felt that feeling in my stomach, and my ass began to tighten. “I think I’m going to cum,” I said. “Skyler?” “Yes.” “I love you.” I was so shocked and yet so turned on by what he just said that I found myself answering, “I love you, too…Oh my God, I love you too.”

Then he said my name, “Skyler.” And I said his, “Caleb.” “Skyler.” “Caleb.” “Skyler!” and I tried to say his name again, but my stomach turned over, and all I could get out was “Ca-“ before I slid all the way into him and my cock pounded load after load of cum into him. He moaned with surprise at the force of every blast, and kissed my wide open mouth as I collapsed into his arms.