The first of many to come...
He wasn't my first, or my last, but he was probably my favorite. Like many young guys exploring my awakening sexuality, I had a few 'jack off buddies'. The times we spent exploring our bodies (and each others') helped me to grow and created many fond memories that I still use occasionally to get off.
Pierce was my favorite. A good buddy who lived close by, we spent many afternoons together. Pierce was an only child whose parents worked, leaving us plenty of time to be alone. I don't remember how it all started, but we spent many afternoons in his basement bedroom looking at his porn stash. It wasn't long before we were masturbating together, and eventually each other.
He was a big kid, 6'3' or so with blonde hair and fair skin. What impressed me most about him physically was his cock. Bigger than mine, Pierce's member was a good 8' and nice and thick. Circumcised and surrounded by a modest amount of golden blonde hair, I thought it was magnificent.
Our times together always followed a familiar and comforting course. We'd spend a few minutes looking at a magazine or a low-quality video. Then we'd remove our pants and underwear (His boxers my briefs), and stroke ourselves until we were fully erect. Then he would lie back and I would take his big hard cock in my hand and stroke him gently. With my other hand I would gently cup and rub his nice sized balls with just the right amount of hair. I would occasionally take breaks to squeeze his shaft, and smear a drop of pre-cum under the head of his penis. Finally, I would stroke him in earnest, and he would begin to thrust his hips. It wouldn't be much longer and his face would flush, and his breathing would quicken. Then with a soft grunt he would cum three or four spurts of thick white semen on his belly and pubic bush.
After cleaning up with some tissues, he would turn his attention to me. Lying next to me with his softening cock rubbing against my bare leg, he would gently and expertly stroke me. I would relax or maybe stroke my balls a bit while he worked. Between the porn and the sexual contact, I would be very aroused and ready to come in only a few minutes. Pierce would sense my impending orgasm and pause briefly to allow me to position some tissues on my belly (my habit at the time). He would then increase his pressure on my dick and stroke me faster. In a few seconds I would unleash my own orgasm.
What I always enjoyed about these sessions, and our friendship as a whole, was how relaxed everything was. He wouldn't say much, we didn't feel guilty, or worry when we got our cum on each other. After our orgasms, we would dress and talk or play video games. It just always felt normal and natural to masturbate each other.
I haven't seen Pierce in a few years and we're separated by over a thousand miles. However, I sometimes fantasize about reconnecting with him for one more comfortable session together.