I'll give a rundown of all the milestones:

First handjob from someone else, given by my first girlfriend when I was 13.

First blowjob from someone else (yes, I'm a self-sucker), given by a gay guy friend of mine when I was 16, in the darkroom at my high school. I stayed the night at his house the next weekend and ended up 69ing, so that was the first of a few times I sucked a cock. He offered his ass virginity too me, and I would have taken it had I known it would be the only chance I'd get for anal, from man or woman (still to this day, dammit). I think at the time it just seemed impossible for this dick (fat) to go into that hole (tiny), without tearing something. I'd obviously not seen much porn.

First vaginal intercourse a couple weeks after I turned 18. My first girlfriend wanted to do it, but I was too dense to get a clue (apparently it wasn't a clear enough message when she came up to me in the hall at school and put a condom in my hand), so I would never be able to claim having gotten laid at 13. So it goes. This was with a girl a buddy of mine had introduced me to, who we had previously tried to let us DP her. She ended up just wanting to fuck me, and because this guy was supposed to be my best friend at the time, and he was trying to hook up in a more serious relationship with her, I didn't feel right fucking her right then and there with him stuck watching, or at least hearing from very close proximity in the other room of her very small apartment. I waited a couple weeks until it sank in that she wanted me and not him, and he gave up. Even so, it really screwed up our friendship for a long time.

I guess the number one lesson for him was, if you are trying to get into a long term relationship with a girl, don't bring your friend over to DP her, especially if this friend has a nicer body and a much bigger dick as well as a less obnoxious personality. For me, it would be that even if your friend tells you he doesn't mind if you fuck the girl he was trying to get with, that doesn't mean that he actually doesn't mind, or will not in fact end up holding a jealous, bitter grudge for 8 years.

Apart from a finger or two, my ass is still virgin, and I aim to keep it that way, assuming nobody slips me rufies.