Coach, assume you mean the first sexual intercourse. It was with my first true love in her dorm room, at a time when our relationship was on the rocks. It was her first time as well. It was clumsy on my part and over too soon. What would have helped is coaching from an older woman (sister, mother) on relationships. Wasn't until marriage that a woman finally taught me how she wanted to be treated.
Gnome
It was with a Korean prostitute, and I was too nervous to get it up. The poor girl tried all night and couldn't get a rise out of me. Sometime late the next morning I managed a climax without an erection.
My buddies all assumed I was some kind of stud for staying with her so long. For the next year I enjoyed a rather checkered reputation.