My sophomore year of high school I became good friends with a boy named Mark. Mark was a year older than me but, but we were both playing on the school basketball team together and so spent a lot of time together.
I didn't think of myself as gay at the time but certainly knew that I was very attracted Mark. I had admired his body in the showers many times; I thought his pale fair skin contrasting with the jet black hair of his modest bush was breathtaking. I caught myself many times waiting in the showers for him just to make sure I got a chance to see him naked. This was in the mid-80s, and his physical resemblance to the young Tom Cruise was striking. I'm pretty sure Mark was straight, but I've never asked.
Our class schedules rearranged after the Christmas break, basketball was still going on and both Mark and I ended up with the last period of the day free. With practice not typically starting until four, this left us both with from 2:30 to 4 free. Mark lived far enough away so it didn't make sense for him to go home every afternoon and then try to get back in time for practice - so we started hanging out at my house, which was very close to the school.
One afternoon Mark was laying on my bed as were talking, I was doing a bit of homework at my desk. Mark was talking in some frustration about his lack of success in getting together with a girl he had a crush on. I don't know to this day what possessed me but I jumped in the bed next to him and giggling said "give it to me big boy". He laughed a bit but then pulled me close and we both got quiet and still. He decided to show me, I think in the spirit of educating his less experienced buddy, what he'd tried with his reluctant girlfriend.
He slid a hand up the back of my shirt and said "just like this I was trying to get her bra undone" and he rubbed me gently between my shoulder blades. "If I had gotten her bra off I would've rubbed her nipples like this", he said as played with my nipples. "Did you know a man's can enjoy having his nipples played with?" I didn't but now did. My cock was rock hard, but I was scared he'd notice. I always felt insecure about my body after having compared it to my teammates in the showers. I had the smallest cock on the team probably only 5 inches hard; and a very small tangle of blond pubes at the base.
After a few more moments of teasing he rolled me onto my back and spread my legs. "This what I would have done next", I remember him saying. It was wintertime so we were fully clothed - he got in between my legs lay down on top of me and stunned me by growling "grab my ass". I did but in my inexperience all I did was hold on. I never thought to rub or caress his ass. To be fair I was stunned at sexual fantasy coming true... But I hung on to his ass as he ground his crotch against mine. He paused after just a few thrusts. He asked me to talk dirty to him but my mind went bank, and I was scared to start talking about how hot I thought he was. I took advantage of the pause to get myself on top and return the favor by grinding my hard cock into his crotch.
We Experimented with several different positions and commented on our favorite ones... All under the naïve guise and commentary "of this is what we would be doing if we were with girls". I was so naïve I wasn't sure he was truly sexually enjoying the activity... A few times I was sure I felt his hard cock pressing right up against me...only as an adult did I look back and with great embarrassment realize there was no other reason for him to be grinding on the way he was. At the time I was still terrified I couldn't believe that another boy could find me sexually attractive.
I finally couldn't take it anymore and determined to find out whether not his cock was actually hard. I wanted to stick my hand down his underwear but wasn't sure how he would react. So I took a half step, I just took my finger and slid it underneath the edge of his elastic waistband. I thought if he doesn't object I can slide my hand in a bit farther... Before I got very far I ran into the head of his massive cock. His erection was so big it literally came out of his underwear - I rubbed my finger against the head of his cock and he moaned "I'm cumming" so I stopped. He didn't cum. I made a move to touch him again but he stopped me. Eventually he let me slip my hand into his underwear and I caressed balls, ran my hand through his pubic hair, and took his stiff hard length in my hand.
Every time I started to stroke him though he would make me stop quickly. I humped the day lights out of him in between sliding my hand down his underwear and exploring his crotch. Eventually he allowed me to unzip his pants, and pull his cock out altogether. What a sight! I can still see the taut head of his cock, how swollen stiff he was with excitement, how big he was compared to when he was limp in the showers. even better up close the peach fuzz of a treasure trail was just visible, thrilling me that this "older man" would let me touch him.
I knelt down in front of him, His pants now down around his ankles. "Don't suck me, he said - but you can jerk me if you want. But I am going to pretend you're a girl" At that point I would've gone along with any scenario as long as it led to me touching his cock! I unzipped myself and took my small 5 inch stiff cock out - I caught him staring but to this day don't know if he was sexually excited to see me hard or not. I wrapped my hand around his hard cock and just pounded away - no subtlety at all, just pounded as hard as I could. In less than 30 seconds the purple head of his cock swelled, he moaned my name and began shooting ropes. I stood up and wrapped my arm around his shoulder and stroked myself off. I didn't shoot quite as far as he did.
We only hooked up one other time after that. When I think of my high school years that surely is one of my favorite memories - both of us with our pants around our ankles, cocks in each others hands - no longer shy about our stages of development but instead enjoying each others bodies. still a favorite memory to jerk off to!