My name is Skyler, and until I was 20, I had always been completely straight. I was even confident and successful with the ladies. I had several girlfriends, some of them serious, and many friends with benefits. I didn’t notice the signs at the time, but looking back, maybe it was significant that I always preferred sexual activity in the dark, and that I loved going down on girls, getting head, and that doggy style was my favorite position. It’s not like I was attracted to guys. Sexually I was just always looking for something different. I didn’t think that girls weren’t doing it for me, but I knew I was always looking for something new. I thought I was just adventurous. Sometimes when getting a blowjob, I would cum by fantasizing that it was a guy doing it, but I didn’t think much of that. I thought my many unsuccessful attempts to get a girl to try anal sex came from a totally heterosexual place. I had never found another guy attractive in real life. So what happened with Caleb took me totally by surprise.
I played the drums in a three-piece rock band. One day in August, we played a small show in a pavilion next to a river. My long-term girlfriend couldn’t make it until later. We lived together and she’d seen enough gigs to last her a decade. After the band set up our equipment, we had an hour before we would play. My bandmates suggested going swimming, and I shot the idea down. None of us had swim clothes or towels, and I didn’t want to be wet for the rest of the day. Then I saw them; Two thin young ladies in bikinis were walking toward the river with a young, shirtless guy. The whole band stopped for second to watch them pass.
The girls were very pretty, but I couldn’t stop staring at the guy. He was average height and build, brown hair and eyes. His face was gorgeous. His tanned body reflected the sun, and the shadows showed the gentle curve of his shoulders and biceps, his barely discernable six-pack, his belly-button crowning a perfect treasure trail leading down toward black swimming trunks that both hid and highlighted a delicious bulge each time he stepped. As they passed, I noticed the perfect arc of his butt. Without any time for comprehension, electricity passed through me. I had never been as attracted to any female in my life as I was to this random boy on his way to the river. I found myself saying, “Nevermind, let’s go swimming.”
“Dude, you literally just said you didn’t want to go swimming.” Responded the guitarist. I felt flush and called out. I thought quickly and answered, “Yeah, but now that we’re just sitting here, it is pretty hot today. And now there’s cute girls there. Matt, maybe you’ll hit it off with one of them.” I gestured toward the keyboard player, who was the only one of us who was single. Now they shot the idea down, and a little embarrassed by my sudden enthusiasm, I quickly let it go. We hung around and waited for show time. Talking and joking, my eyes frequently returning to the spot where the trio had cut through the hedges to the river, but I couldn’t see them down the bank, and they didn’t come back up.
Two hours later, we were mid-set and jamming hard. I looked up at the small dancing crowd and saw the two girls in bikinis dancing in the front. I scanned the crowd, but I didn’t see him. I played the rest of that show self-consciously, like I was hoping he could hear it and I was trying to impress him. It was the silliest thing. It made no sense. We all agreed afterward that it was the best gig we’d played in months. They never knew why.
After the show it was getting dark; late twilight. I was loading the drums from the pavilion to a spot under a tree where I could pull up my car. This took several trips. I brought some cymbal stands over to the pile of drums, set them down, and heard a voice above say, “You guys were really good. My friends really liked you.” I looked up, and there he was, sitting in the tree on a large branch just above my drums. I thanked him. “I’m Caleb.” He said. I was almost disappointed that he had something so definite as a name. I told him my name, and we made some small talk for a few minutes. He sat in the tree, and I stood there looking up at him feeling totally uncomfortable with my crazy avalanche of emotions and a sense of urgency I that couldn’t identify.
I was restrained in the conversation. I couldn’t talk to him naturally. I got butterflies with him in a way I never did with girls. My mouth was dry and my posture awkward. I couldn’t stop myself from laughing a little at everything he said, and my eyes went everywhere and back again. Exasperated, I kept thinking, ‘What the hell is happening to me?’ at my sudden inability to have a normal conversation with another guy. 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. His deep brown eyes glistened from the stage lights, and I kept staring at his amazing, full lips. A part of me was absolutely panicked, and 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. He said his Mother was a nurse who often worked nights, and that he often had parties with a lot of hot chicks at his house. I took the number and put it in my pocket. Then I left to get another load of drums. When I came back, he was gone. I felt relieved, disappointed, and suddenly empty. I caught my breath.
I thought about him for days afterward. At first I tried not to, but I gradually grew to like it. It was like a secret door opened into a little world inside me that made no sense, and that I could never tell a soul about. I didn’t know what it meant or what I might want from it, but I liked this new secret. There was a foreign and exhilarating newness about it that made me want to live in that electric excitement. I found myself thinking of him while I masturbated; how he looked with no shirt on, his perfectly defined treasure trail, his big dark shimmering eyes, how his voice had this way of quivering just a little when he talked. I imagined how soft his luscious lips must be, how it would feel to have his mouth pressed against mine, clutching his body close. My girlfriend and I had sex one night, lights off. I tried to pretend that her lips were Caleb’s. I kissed her the way I imagined I would kiss him. When I went down on her I thought about going down on Caleb. As I used my mouth on her clitoris, I tried to imagine that it was his heavy breathing I was hearing, and that the shapes moving in front of me were his hips and stomach writhing in pleasure. I tried to shut out her feminine moaning and ran my hand up the very center of her stomach and torso to place my palm on her chest without encountering her breasts. While I was behind her, doing her doggy style, I started quietly mouthing his name, ‘Caleb….Caleb…Caleb…’ It made me so hard. I thrust slowly as deep as I could and pressed my palm onto her lower back, then grabbed her hips. I was thrusting differently than usual. Not faster or more forcefully, but more fully. I kept mouthing his name as silently as I could, getting unbelievably turned on just from the sensation of my tongue pressing the roof of my mouth and my lips coming together at the end. “Caleb….Caleb…” It felt exciting and wrong, and so hot. I came like I hadn’t in a long time. She agreed that it was the hottest sex we’d had in months. She never knew why.
After a week, I finally worked up the courage to call him. My girlfriend was at work all day, and 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. He answered and his voice sent a jolt through me. I told him it was me and asked if he had time to meet up to get the pictures 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 washed myself and got dressed almost as part of a fantasy. Not thinking anything would happen, but pretending I was preparing myself for him. I wore a green t-shirt, my favorite boxers, and a pair of jeans that were just a little tight. I got in my car and pulled out of my driveway smiling, hoping that before I came home, I would be different.
I parked the car in front of his house, walked up the steps to the door and rang the doorbell. My heart raced in the endless anticipation. I was on auto-pilot. When he opened the door, I was struck by how gorgeous he was now that I could see him in the light up close. He was wearing a white t-shirt and jeans. He smiled and said he was glad I found the place. As he invited me in, he told me to take off my shoes at the door, and his voice did the little quiver. I slid my shoes off as he walked away, saying, “The pictures are on the computer in my room.” He led me through the house into his bedroom. We talked a little as 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. He told me their names, and pointed out the ones he’d made out with. We seemed in agreement about which girls were the best looking. Then he asked me if I wanted to see the party space, and I said I did. He brought me down a flight of stairs near the kitchen to the basement, which his mother had turned into a guest room. There was a king-sized bed and a couch, and door to another back room that led off from that one. There were small windows near the ceiling.
For two hours we chatted down there. At first standing, and then he reclined on the bed while I sat on the couch. We talked about music, girls, getting in fights, our hobbies. We laughed, paused between subjects, and sometimes he got quite animated. I just sat there, feeling a little like throwing up but enjoying that sensation somehow. I kept trying not to stare at him, and looked around a lot and commented on the surroundings when I felt like I had spent too much time watching his mouth move and trying to figure out what kind of kisser he was. The whole time I regretted wearing blue jeans that were slightly too tight, because hiding my erection was very difficult. A couple of times I noticed small wet spots on my pants where the pre-cum had soaked through. I tried to compensate with outward confidence, but I felt so awkward. He told me he was on his school dance team, and said that was a great way to befriend hot girls. When he talked about girls I felt two things at once. One was relief; like I wasn’t in danger of being anything I didn’t want to be. The other I couldn’t identify; it was a sort of discomfort and almost anger. It was jealousy!
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, reminding me that his mother was a nurse who often worked nights. The party could go as late as we wanted and be as loud as we wanted. He pointed out that there was nothing breakable in the basement. He got up from the bed, walked toward the doorway to the other room, and gestured me to follow him. “Come check this out,” he said, “this is the best make-out room.” I moved slowly to get up, waiting until he was turned away to rise and discretely tuck my boner up under the waistband of my boxers and pants, pinning it to my stomach before laying my shirt over the incriminating area and following him into the back room. It was a small space with blue walls containing nothing but a dresser and a small twin-size bed. “I bring chicks back here a lot,” he went on, “the door has a lock, and the bed is really comfy.”
With an air of fun, I leaped into the air just a little, 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!” Then he said, “Check this out.” And he sat down on the bed right next to me, his body almost touching my hip, and bounced himself up and down a couple of times. “It doesn’t make any noise, either.” I was so turned on. My hands were cold and clammy, but my mouth was dry. I was quivering nervously, and my heart was racing out of control. The my hairs all stood up like I was in the crosshairs of some electric convergence, and for an instant I didn’t care what happened next. Without thinking, I reached my hand over and placed it on top of his leg halfway up his thigh. He stopped and looked right at me. It was suddenly totally quiet. His eyes pierced into my soul, and all of the blood in the world rushed to my face. I almost thought I would catch fire. I wasn’t sure if he was about to punch me in the face or throw me out of his house or what. With all the cowardice of a deer in the headlights of an oncoming Mack truck, I stared directly back into his eyes. I couldn’t think of any excuse, or any reasonable explanation. A breaking, “Caleb.” was all I was able to get out.
He extended one arm over me to support himself, leaning in and craning his head down, and placed his big, plush lips onto mine. Everything stopped. I couldn’t breathe. My heart exploded, and my stomach flipped; but it kept on flipping like it was falling down an endless crevasse. 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. His lower lip twitched a little, and tugged slightly against mine. My mouth was flooding with saliva. I reached my hands up toward his shoulders, and he smoothly pivoted his legs around to bring his feet up onto the bed until he was partially on top of me. I loved his weight on me. All of 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 swallowed hard. Then I leaned my head up to him and kissed him. Then I kissed him again. He was kissing me back. His mouth felt warm and moist as we began to kiss each other with a little more confidence. The kisses started to blend together into uninterrupted encounters. 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 slightly, our lips clasping at each other, sucking just a tiny bit. Then our tongues touched for half a second before our lips took over again.
I moved my hands from his shoulders down his sides to the back of his hips and held him to me. I wanted to feel the curve of his ass, but didn’t know how to convince myself to do it. It all felt so tenuous, and I didn’t want to break it. My hands just rested in the hollow of the small of his back. Our mouths opened wide, and for several minutes our tongues slid against each other, his warm breath occasionally sliding past my cheek. There was no sound except the for the smacking and lapping of two mouths dancing, the gentle rub of fabric as we moved, and the soft broken breeze of breaths that were excited but self-consciously controlled. We started undulating slightly and grinding just a little. I began to realize that my boner was pressing against him, and a tinge of embarrassment swept through me until I realized that I could feel him pressing firmly into my thigh. I moved my hand down and placed it on his perfectly curved butt. I felt it rise slightly and tighten as he broke the kiss and placed his hand on my chest. I thought he was going to stop this before it went any farther, but he reached down and began to pull up on my shirt. I squirmed around to let him left it over my head and went for his shirt as well. Both fell on top of each other on the floor with a flump.
As we came back together, I could feel his smooth body pressing mine into the bed with intoxicating warmth. As we started kissing, we were both gyrating slowly to feel each other’s skin. My hands moved gently around on his back and shoulders. He was of average build, but the form of his muscles was so hot. I noticed that as we were kissing, we were thrusting our hips into each other; slightly at first, but increasingly in a shared rhythm that created a pleasurable friction. It felt so good that I wanted to scream. I felt a desire I had never known before. It felt like that first sip of water that makes you aware how thirsty you’ve been, and triggers an uncontrollable urge to chug the whole glass. I began to almost quiver all over, and an unknown force seemed to taken over me. I wasn’t in control of myself. Raw urges filled me from some mysterious source and everything became a blur. I wasn’t making decisions anymore. I know that I was sliding my hands around on his smooth back and shoulders. I grabbed his ass firmly. I placed my palm on the side of his face to hold him in place while I tried to tongue his mouth as deeply as I could. My enthusiasm fueled his.
Now we were breathing heavily and kissing with a passionate energy that had filled its vessel and had nowhere else to go. It began to build enormous pressure. We were kissing and dry humping, and I knew he was liking it as much as I was. All of my inhibitions fell away. 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 top button in his pants. He lifted his hips up off of me to give my hand room to maneuver, and held his breath as I unbuttoned and unzipped his pants. Together we slid them down until they were gone. For a fleeting second in all of the movement, the afternoon sun coming in through the small window revealed that his bulging boxers had their own wet stain where he had soaked through.
He reached down to undo my pants, and my stomach tightened and spasmed uncontrollably to the sensation of his fingers fumbling with my zipper. He pulled my pants 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 ticklish as he slid his hand onto my boxers, gently hovering over my hard dick. My stomach spasmed as his hand brushed the boxers, which brushed my penis. I had never felt so sensitive before. He reached his hand into my boxers, his fingers found my throbbing dick, and gently drew it out. As he began to caress it and softly move his hand around on it, without meaning to my voice chirped a tiny momentary moan. He held me in his soft hand, slowly moving up and down. Not like he was playing with it, but like he knew exactly how to make me feel good. I lost all control. Before long, I was thrusting my hips over and over to meet his hand. I began kissing his neck, biting him, sucking a little. I realized I’d got on top of him and was just humping him. I kissed his lips, the side of his mouth, his chin, his jaw, his neck. Then I made a decision, and I slowed down. I gently and slowly kissed his neck, letting my lips sit for a moment, then where his neck met his shoulder, then the crook of his collar bone, then I lifted my weight up and bent my knees to bring my face down to kiss his collar bone, then his upper chest, then his solar plexis, then where his ribs separate. I scooted down a little to kiss his stomach, his slight six pack casting soft shadows like sand dunes. I kissed just above his belly button, then next to his treasure trail, then slightly lower, and slightly lower. His breathing shivered and his stomach shimmied down the bed as I went lower. Then I pressed my lips into a smooth spot just above the waistband of his boxers slightly to the side of his treasure trail. I ran my tongue on the spot, and felt his bulge leap a little, delicately brushing his boxers against the left side of my jaw bone. I moved down and kissed the bulge, and it twitched inside his boxers in reply.
I reached down and pulled his penis through the opening of his boxers, and it was more beautiful than I had imagined. He was frozen, and almost vibrating in front of me. I paused for a moment, staring at his pulsing cock and breathing gently on it as I held it in my hands. I could smell his scent. I kissed the front of it gently, stared at it again. I licked it a little, and then looked again to see that where I had licked was wet. He had stopped breathing entirely, and I looked directly into his eyes. They were huge, and he had an expression like he was going slowly up the first rise of a roller coaster. I think I smiled a little and then looked down at his penis. I slowly put my lips around the top of it and he inhaled deeply. As I moved my mouth down onto it, he moaned and arched his hips to press it farther into my mouth. I was surprised by how hot it felt against the inside of my mouth, and how natural it was to have him inside my face.
His moans practically made me cum in my boxers, and I began to move my mouth up and down on him. At first I controlled it. I would go down, then up, the tip of his penis popping a little as it passed my lips, then I would reengage and go down again. I started using my tongue on him while he was in me. Soon he started to take a little control. 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 effortlessly back and forth on my lips. It tasted sweet.
He started reaching down and touching my head, running his fingers through my short hair, trying to watch me work on him before losing control and falling back onto the pillow in extasy. His moans became more intense, and then with a heavy drawn-out breath laced with total pleasure, he said my name, “Skyler.” His voice quivered a little. I went down 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. I thought I would gag, but discovered that this felt good. I pounded my head down on him as his stomach tensed and his hips thrust upward. His hands clutched at me, then firmly gripped the sheets. He began to writhe and moan. It was a deep and repetitive, “Ugh….ugh….ugh…” that kept getting slightly louder and slightly higher in pitch. Sometimes there would be an extra long pause as seemed to tense, and then, “Ugh…..ugh…” His mouth was hanging open and his big lips seemed to reach for some invisible fruit. He kept moaning with increasing intensity and pitch.
Finally he was moaning was crying out in a pitch that was almost un-masculine and his voice began to break as though he was losing control. “Ugh! Ugh! Ugh! UGH! UGH! SKYLER!!” Then his hips arched up off the bed and stayed there. Every muscle in his body went tense. I felt his penis seem to pulse between my lips, then it leapt and exploded into my mouth, and a load of warm cum seemed to fill it completely. I didn’t know what to do, and I froze, taking the salty semen and holding it in my mouth. He exploded again, sending a large portion directly down my throat. The next explosion came with such force that I nearly 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 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 dripped onto my chin. His big eyes beamed at me and he was grinning with pleasure but a slight sheepishness that he had just enjoyed a blowjob from a guy so much, I used my finger to put that bit into my mouth as well. He laughed. His glistening penis was starting to go soft.
“That was amazing.” He said with a slight raspiness. “What now?” I asked. He looked deep into me and gave me a strange, knowing look. He rolled over and came up on all fours in front of me on the bed. My mind raced. I was so turned on. I couldn’t believe this was happening. ‘Holy shit’ was my only thought. I slid his boxers off, and gaped at his smooth perfect ass that gave way to the curving lines of his back, with a hollow for his spine widening until it became the rise of his shoulders. He turned his head to look back at me and gave me look that seemed to say, ‘I dare you.’ I slid my boxers off, my hard penis wet with precum and waving erect in the air. I kissed where his lower back gives way to the top of his butt crack, and he arched his hips and spread his legs just a little. I kissed his smooth round cheek and then licked his tight winking hole several times. Then I moved to position myself directly behind him. I pressed my already dripping penis between his cheeks and onto his hole. It took some maneuvering, and some massaging with my penis, but I slowly pressed my dick into that spot until it started to swallow the head. It was barely in and it already felt amazing. I kept applying pressure until all at once, the whole head popped into him, and he let out a little moan. “You okay?” I asked, thinking it must have hurt. “Oh, yeah.” He breathed. I pushed in deep and he moaned as I rested bent to rest against his back. There was a long pause. “Caleb?” “You feel really warm.” He answered. “You do, too.” I slowly 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. I loved the feeling of his butt brushing against my hips. I pressed my palm into the small of his back, then grabbed his hips. He pushed back into me hard, then started to rotate his hips upward when I was going in, then downward when I was coming out. It felt so good. He was so tight. I could feel everything. It was like his ass had my the dick and I never wanted it to let go. I noticed that I had started moaning, and that I was gently repeating his name, “Caleb….Caleb…Caleb…” I knew I was going to cum soon and I knew I sounded like it. Then he abruptly 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. We smiled at each other as I repositioned myself and then I slid into him again, and both of us moaned. To my surprise his dick was hard again, and it wiggled against his stomach with each thrust. I pressed in and out repeatedly, kissing his mouth, holding his face with my hands, 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, and had expanded almost until it was being stretched to the point of discomfort. I felt that feeling in my stomach, and my stomach began to tighten. “I think I’m going to cum,” I said. My mouth hung open. He stared at me with gigantic eyes and a face blank in its overwhelmedness, “I want you to.” He said. And he lifted his head up to kiss my wide open mouth. I was too close to cumming to kiss him back. 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-UGHH!“ before I slid all the way into him and my cock jumped and 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 sweaty arms.
