Back in the early 70's, I went to an all boys boarding school in Connecticut. Masturbation was something you did as often as privacy would allow, and of course there were times when I'd hear a roommate late at night pounding away, when he thought I was asleep, or times when you'd walk in on a roommate, or get busted mid-nut. Basically, by years end, you had seen every other boy naked, either in the dorm showers, or the gym showers, as after school sports were required of every boy, but I never participated in a boy/boy masturbation sessionsÂ¦ until my junior year.
I was at soccer practice, and I pulled my groin. The coach sent me to the training room, and the trainer, a senior named Kevin with a broken ankle, told me to get into the whirlpool. I stripped down got into the whirlpool, and enjoyed the warm water swirling around me. The current caused me to sprout a boner, and when the trainer came back in and told me to get on the massage table, I hesitated. He looked at me, and matter of frankly said, if you have wood don't worry about it, it happens a lot. Just wrap yourself in a towel and get on the table. He turned his back, and I quickly covered up, and lay on the table chest down. He began to massage my thigh just above the knee, and moved upward, he pushed the towel up as he went up, eventually ending at my butt cheek. He told me to roll over, and did the same to the front of my thigh, until he reached my crotch, he massaged the groin muscle, occasionally brushing against my nut sack. My erection was covered by the towel, but its outline was very evident. He focused on the groin muscle, and each time the back of his hand brushed my nuts, my erection would twitch beneath the towel. Kevin pulled the towel off me, exposing my dick. He moved his oiled hand around it, and said guess I need to massage this muscle, it looks very tight. The strokes were masterful, much better than I had ever down before, as he alternated hands, rubbed my nuts, and played my nipples. I closed my eyes and just enjoyed it. Each time I was close, he seemed to know exactly when to back off, releasing my cock, and fingering my nuts and rubbing my chest and stomach, then returning when I returned to the plateau. He continued to tease, rub, and stroke me, until I finally lost it, and shot strong spurts onto my chest and stomach. He rubbed my cum into my chest, as I regained my composure and breath, then took the towel and wiped me up.
That night my roommate Paul asked me who the trainer was, and when I said Kevin, he asked me if he jerked me off. I didn't say anything, but Paul smiled at me, and said he's the best isn't he? That led to us talking about how Kevin had done him too, and later that night Paul and I jerked off in the room at the same time for the first time.
The next day I eagerly awaited soccer practice, with a hard on most of the day. At practice the coach ordered me to the trainer, and we had a second session, even better than the first. I asked Kevin if he jerked off all the boys that he treated, and he smiled and said, only the ones with hard ons, that let me. I asked him how many got hard, and he said most, and I asked him how many he jerked off, and again he said most. Kevin never asked me to do him, which was fine with me, because honestly I wasn't interested in him, just his magic fingers. Sadly, my groin healed, and I only had 5 sessions with him, but his handjobs are still the best I ever got.