With female:
17, senior year of high school, crazy chick I was dating as a rebound after a long relationship, bought some condoms at 7-Eleven walking to her house, snuck in through a window, she finished before I could (legit because she spent my hour long walk to get there masturbating and talking to me on the phone), had to finish myself off in her legroom, back out the window, her Dad and a shotgun appear, shots fired, running faster than I ever haver, walked home, sorted and slept. Nothing too interesting.
With male:
19, just left the Army, got wicked drunk at a party, was asked out by a few guys for no reason I can imagine, go on a date to see inception with the better looking one, went to his place, made out, played Mario Party, fought yelling at him for being stupid repeatedly, went to his room, made out, things went up to sex, had condom, no lube, going in dry was... no... wasn't pleasant... had no ride so I spent an awkward night there... he still texts me, I still ignore him because he's fucking stupid. Life lesson, if you expect homosexual sex, have lubrication available.