Not sure this belongs here, since someone else did it to me, but this thread brought back a memory I’d forgotten for years:
The summer before college, I became good friends with a super cute, tall guy through some mutual friends. We were all hanging out on the last weekend before leaving for school, playing a game at a dinner table, just talking and having a few drinks, very chill. He was seated on a long bench at the table, and I was standing right behind him, leaning on a post. We were all taking so he knew it was me right behind him. At some point, he leaned his head back to rest on me. This was totally unexpected, as we’d never had that kind of intimacy before. I didn’t know at first if he realized it, but he was leaning his head right on my dick, and it was summer so I just wearing basketball shorts. I didn’t move, just letting him rest his head on my dick for a while, but then he started rocking his head side to side, very gently. That’s when I realized he probably knew exactly what his head was resting on. My dick started to chub a little, but I controlled myself from getting too hard. He just sat back, casually rocking his head over my plump dick. This lasted for a long while, probably 10 minutes or so. Nothing came of it and we all left town after that. I didn’t see him again till the following summer, but which time he’d gained like 30 pounds of muscle. I wanted him so bad but we never mentioned it.