My brother lost his virginity to a total skank at 16.
How's that embarrassing? Well, they were so drunk he didn't realize that: a) I had only gone to bed 5 minutes before b) I hadn't shut the door, so I had to hear everything. Praise Bob for premature ejaculators! c) After a minute, it started feeling really good, tighter than before... and then he realized he had slipped out and was porking the space between couch cushions.
I suppose the time my sister made me show a friend of hers a porn tape also counts. All was fine, if a bit creepy(showing my 15 year old sister pr0n, not knowing she was a regular swiper of my stash already)...
The inevitable money shot "came", the guy whipped it out and blew a load all over the girl's back... and my sister said "GOD, I HATE IT WHEN GUYS DO THAT TO ME!"