Story Details

First Time

Quartercupofawesome on Gay Stories

First Time

“Have you ever kissed someone?”
He leaned closer.
I closed my eyes and leaned forward slightly, as if to give permission, the anticipation was making my hands sweat.

6 Weeks Earlier

Christian, a normal everyday 13 year old, well, mostly normal.
Jack, average 15 year old athlete.
We met in summer baseball, I was right field, which is baseball code for “you suck”. I spent a lot of time watching Jack, he was the pitcher. We didn’t talk much then. But he was the only one on the team who was nice to me. Everyone else just ignored me. Day after day I would stand in the sweltering heat watching the infield make plays, trying to be ready in case I got a chance to actually touch a ball. But mostly I’d watch Jack, he was amazing, consistently whipping the ball into the strike zone. And after practice when we were waiting to get a ride home all the guys would rough house and make jokes at the others expense. Jack wouldn’t talk much but when he did it was worth it. He would joke and laugh with everyone else. He was really funny. And, every once in a while he would see me looking at him and give me this crooked have grin that made my face hot.

The sun was high in the sky when I arrived at practice that day. Jack strolled toward me, taking his cap off and running his fingers through his sweaty brown hair, he called to me.
“Hey, Chris! Do you wanna come over after the game tomorrow to play games? I already invited Steven and Dustin.”
“Sure, I’ll ask my mom and let you know “
“Ok, great” and with that he jogged back over to the pitchers mound. As he did so his shorts fell down a little, just enough to see his underwear. They were black with a grey waistband. My heart started beating very fast, and hands started to sweat. ‘Stupid New Mexico heat’, I thought. I walked over to the dugout, leaning over to drop my bag a discreetly adjusted my hardened member, tucking it into my waistband. Worst part of puberty, boners happen for no reason.

The next day I rode with Jack and Dustin to his house. This wasn’t the first time I had gone over. His parents were quite nice, his dad reminded me of my uncles back in Ohio. We were all sweaty and gross after our game so we took turns in the shower. Dustin went first while Jack and I played a round of table tennis in the basement. Then, when Dustin shouted down that he was done, Jack went, I went back upstairs to watch tv with Dustin while I waited. Dustin was nice but it felt like he didn’t like me much, I guess he was just polite to me cause Jack invited me over. Soon Jack walked out of the bathroom.
“Kay Chris all yours”
“Ok” I got up and started down the hallway before realizing I was in the way of Jack heading to his room.
“Oh sorry” I tried to flatten myself against the wall. Now I got a really good look at the state Jack had exited the bathroom. Baggy shorts, no shirt, towel drying his hair with one hand. My eyes drifted down his chest to the band of his underwear peaking out from his shorts.
“It’s alright” He slid past me. Grazing my pelvis slightly with his hip and butt. I started to feel movement and turned quickly to the bathroom.
My thoughts lingered on the image of his chest, dewy and smooth with defined muscles and subtle curves. I sprang to life beneath my shorts. As I began to undress I saw my full erection. Pointing to the ceiling with a slight curve upward. My pubic hair barely visible with hues of red and blonde. I sighed and started the shower. And my mind flashed with the image of Jack standing in the hallway half dressed. My member twitched. As I stepped into the shower I remembered the feeling of his hip against my groin. As I started to wash my body I couldn’t shake my boner. I thought nothing of what caused it. I had always found guys attractive. Girls too. But as I was kinda dorky and shy I hadn’t had much attention with either sex. Without realizing it I was stroking my stiff cock. And as suddenly as I started, I was done, with a muffled grunt and several spasms, my seed fell to my feet and was washed away. With that I could think much clearer. I finished my shower and wondered if Jack would ever be interested in me.

Dustin let out a loud snore from down the hall. He already went to bed while Jack and I took turns playing Super Smash Bros, trying to unlock a new character. We had been having idle chat until now. Normal stuff, until our conversation turned to girls.
“I dated a few girls but nothing serious.” Jack said in between rounds “You?”
“Just a girlfriend in 5th grade but nothing past holding hands. And um.”
“Don’t tell anyone, but I dated a guy I knew before moving here.”
“Oh I didn’t know you were gay” Jack said indifferently. At this point he had put the controller down.
“I like both, I guess that means I’m bi”
“Have you ever kissed someone?”
He leaned closer.
I closed my eyes and leaned forward slightly, as if to give permission, the anticipation was making my hands sweat.
I waited for what felt like forever until I felt his hot breath on my lips. Filled with desire I lunged forward, eyes still closed, and in my heated passion hit him square in the forehead.
“Ow . .” Jack sat with a hand on his head. I curled into a ball partly because of the pain and partly because of the embarrassment. “Sorry” I mumbled almost in tears. Silence. ‘Oh God he hates me! Uhg why am I so stupid!’ I look up to see that half smile of his beaming across his face. Letting go of my head, tears in the corners of my eyes I just look at him, slightly bewildered.
“You’re cute”, and with that he grabs the back of my head and presses his mouth against mine. Heat flushes my cheeks. Dizziness overtakes me. He softly opens my lips and breathes, his tongue glides along my bottom lip as my own comes to meet his. I sway with lust and grab his hand that is resting at his hips. My mind races and swirls as our tongues dance back and forth. And slowly it ends. Jack pulls away as I stay frozen in place. One hand gripping the floor, the other squeezing his hand. He pulls me in for one last peck and the brushes his hand down my back. With that I lose all composure and collapse into his chest. Minutes go by, my mind is still racing with the passion I just received, my first kiss, when the stillness is broken by the sound of Jack’s voice.
“I’m not going to fight it anymore.” I turn up to look in his eyes. “I want you” My face turns red. “But . . . “
“Can we keep this between us?”
Yeah that makes sense, being gay is still taboo and this is a small town, people talk.
I nod. And before I know it Jack has scooped me up once again in a passionate kiss, swirling and hot. This time I become more animated. Caressing his thigh and wrapping my arm around his back pulling him closer. He returns my touch with his own. I love the gentle way his fingers dance along my skin. Soon I’m laying down, with him on top of me, I feel his weight pressing into my hips as he kisses me deeply. I run my fingers up his back and into his thick hair.
We kissed and grinded into the early morning. Finally I left to sleep on the sleeping bag on the floor. We slept til noon that day. Getting up and going straight out to play xbox. We talked and joked just as friends. Pretending last night never happened. But anytime we were alone, we couldn’t contain our lust. Once we even made out in the bathroom at the ball park.

Soon summer ended and our sleepovers became more and more rare. When school started we almost never saw each other. And soon I heard from my friend who went to the high school that he was dating a girl from his math class. I figured our time was over and I would just have to be okay with that. I made friends in a couple classes, I joined drama club, I hung around in art club with, Whitney, my neighbor and friend that was in the high school. I even kissed Isaac at a school dance. But we just decided to stay friends. Jack and I would txt every once in awhile. He said I should come over and play games, but I was nervous about seeing him again and always made up an excuse. Until one night in late fall, I went to the local fair in the center of town. I was walking around with Whitney and Carlos, a friend of Whitney’s, when I saw Jack at the basketball court. I stood and watched for a long time, before I realized Whitney and Carlos walked off without me. As I began to look around for them I heard a voice.
I turned and saw Jack standing a few feet away.
“Hey” I just looked at him. His eyes were a greenish grey shade that matched his shirt. He furrowed his brow.
“Do you wanna go for a walk, catch up?”
“Sure” I wanted to be mad at him for making me so sad. But I’m too empathetic, and understanding, it sucks.
“So you still dating, um”
“Lindsey? No, um, we broke up after,”
“After?” Jack looked around to see if anyone was in earshot.
“We had sex in her truck”
My heart sunk. Of course he would sleep with her. As much as we had fun he is the straightest guy I know. And he is just a guy, we think with our dicks.
“Christian?” He looked at me, leaning slightly so he could meet my eye level.
“Hm? What? Oh sorry man, I can’t believe you guys would break up. Are you okay?”
“Christian” He stopped now to face me. And I realized we had walked behind a building on the edge of the park. Jack looked into my eyes. He frowned.
“I’m sorry “
I began to babble, “No, you don’t have to be sorry, I mean we weren’t dating or anything we were just messing around, your not into guys so I understand, besides you still invited me over it was me who . . . “
Jack kissed me. He pulled me into his arms holding me tight, and gently caressed my lips with his own. I instantly swooned. Grabbing his belt and pushing my hips against his I turned a gentle embrace into an aggressive grind. He answered back by grabbing my hair and shoving his tongue down my throat. We fought back and forth like this for several minutes before my head cleared enough for me to pull away.
“Christian, I’m sorry, can I be with you again? Only you.”
“Why, tell me why you want to be with me? I thought you . . . You don’t like guys . . . “ I pulled farther away and leaned against the brick building. Crossing my arms and directing my gaze to the ground.
“True,” He reaches towards me and lifts me face to meet his “but I love you”
My face flushes and my eyes start to water. I collapse into a ball and start to cry. Jack kneels down and wraps his arms around me. “What’s wrong? Are you still mad at me?”
I shake my head and with tears pouring down my beat red face I look into his eyes.
“I love you too” with that he kisses me again, with a new heated passion. I melt in the wall and let my emotions overtake me. After several minutes, Jack lifts his head and looks at me.
“Do you wanna have a sleep-over tonight?” He stares at me with a lusty smile. I swallow nervously at what he has in mind.

At his house we played xbox, I brought this game I thought was funny while we took turns playing it. We played and talked for a few hours until we were sure his parents were asleep. We got up and went to his room. Jack walked in switching on the computer as he passed.
“I wanna show you this game plus it gives us an out in case we hear someone coming”
My sexually charged mind hung on the last word. All I could think of was the bulge growing in my pants. It pressed against the thick denim of my jeans and started to hurt. Jack turned around as if he could hear what I was thinking. A nervous smile stretched across his lips. He sat down at the computer to boot up the game, our back up plan. And then he turned off the lights. Meanwhile I was stretching out on the bed and without thinking had started to adjust my bulge.
“Are you uncomfortable?” Jack turned away from the computer.
My face flushes. “Yeah um, I can go to the bathroom real quick. Take care of it.”
“Let me see” Jack sat in the chair a couple feet from the bed. “We can do it together if you’re nervous”.
I nod and move to my zipper. Jack does the same, sliding down his jeans slightly and pulling down the waistband of his boxers, they’re navy blue today. His already erect cock flings out of his pants. It’s long and thick and curves slightly to his right. Without realizing I already took my cock out and began stroking. Jack follows my lead and his eyes watch my dick bounce slightly with the motion of my hand. My eyes dance from his cock to his eyes but Jack’s gaze never leaves my hard erection. His intense stare just makes me hornier. My masterbation becomes more intense. Now we’re moaning a chorus of mms and ahs until finally we both cum. I let my cum fall onto my stomach and boxers. When I look over Jack had done the same. I licked my lips. I’ve tasted mine before and it doesn’t taste bad. But the thought of his cum drove me mad with desire. I kneeled down and crawled to the chair until my eyes were level with his post-ejaculated cock. I reach up to touch it. I look at him with yearning and he nods. I touch just the tip of his dick right where a little cum still remains. His dick twitches. I take one finger and scoop up some cum off his stomach, and put it in my mouth. Salty, but pretty good, I slowly slide my finger out of my mouth, I hear Jack moan and look at him. He is biting his lip and watching me. This drives me nuts, I grab his cock and like the cum off his stomach and boxers while he moans with pleasure, I feel his cock pulsing with new life in my hand. Lastly I put my mouth very close to the tip of his dick and pause. I have never done this before. With a deep breath of courage I wrap my mouth around his member. He moans, I lick him up and down and he responds to every motion. I wrap my lips around him and engulf him completely, shoving him as deep as I can into the back of my throat.
“Ah, cumming, mmm” With my mouth still around him he shoots his load. The volume of it was more than I could handle and I let go, a stream falls onto my shirt and some from my mouth dribbles onto my chin. With renewed energy Jack straddles me and kisses me deeply, swirling his cum around in my mouth. His still dripping cock rubs against mine. This sends me into a frenzy of passion. I run my hand under his shirt and circle his nipple with my index finger. His whole body tenses with pleasure and I realize he must be very sensitive. I rake down his chest and land at the edge of his jeans, sitting just slightly below his hips so I can feel the mounds of his cheeks begin. He stops for a moment, my hand on his ass, swallows the cum he scooped from my mouth and leans in to whisper right in my ear.
“Can I fuck you?”
Just the words sent me into a spiral of ecstasy, diving deep into my subconscious and finally emerging feeling like I almost drowned.
“Yes.” I finally manage to mumble. And with that Jack is striping off my shirt and kissing me from mouth to cock. He doesn’t put it in his mouth but he licks the tip, a little bit of cum still there from earlier. He reaches under his bed and pulls out a bottle of lotion.
“Will this work for lube?”
I nod unable to speak without stuttering.
He strips off my pants down to my ankles and places himself between my legs. Jack gets a few squirts of lotion and rubs it between his fingers. He run his slippery digits from my balls to my hole and begins to circle my entrance. I moan at his touch. He leans down to kiss me, his tongue swirling my mouth. Soon he has one finger in then two. I can’t hold back and I moan deeply, muffled by his mouth still pressed against mine. Soon he pulls away to get a better look at what he’s doing. He fet more lotion, slathering it on his stiff erection. He slips his fingers in and out to ensure my hole is ready. He removes his fingers and eagerly places his cock at entrance. He begins to push and just his tip slides in. Both of us stifle a moan. He pauses to regain his composure. I’m breathing heavy, my heart pounding so hard I feel like it could pop right out of my chest. My asshole feels stretched like nothing I’ve ever felt. It’s both painful and pleasurable. Jack begins pushing again and I let out a sharp cry. He stops and all I can muster to say is “slowly”. He pulls out a little and then slides in a little further. He does this several times until his cock is about halfway. At this point his thrusting becomes longer and faster. I can barely keep from screaming in pleasure. I stifle my moans by biting my bottom lip. It doesn’t take long before we are both at our peak.
“Im cumming.” And at the he make one last thrust into me and fills me up. The feeling of his cum inside me is too much and I can barely stutter out “cumming” before it shoots out of my hardened member and straight onto my face and chest. This doesn’t seem to bother Jack because he just collapses on top of me. My whole body relaxes and my mind catches up with everything that just happened. I start to cry quietly. Jack looks up, cum still splattered on my face and frowns.
“Are you okay? Did I hurt you?”
“I’m fine” I say as my crying subsides. “I’ve just, that was”
“I love you” Jack says as he kisses me deeply.

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