Oh jeez...

We were both virgins, and I had heard for as long as I could remember that "it always hurts the first time for the girl." So my dumbass 16-year old self decided "The sooner we get through the pain, the sooner we can enjoy it!" So I thought it was a great idea to thrust as deep as possible on the first go.

So yeah. Losing my virginity involved half a second of sex and 15 minutes of consoling my poor, sobbing girlfriend.

Karma was a bitch with that one though, as the second time we tried (after like 30 minutes of foreplay), I couldn't get it up - still worried I would hurt her again and remembering how much I had done so before. She ended up laughing at me, saying "After all that build-up, you can't even get it up? What a loser." Which, you can imagine, did very little for my ego or my impotence problem. Turns out she wasn't a very nice person, in the end. Still feel bad about the first time, but considering the crap I went through with her later, I chalk it up to a rough learning experience now. High school relationships, amirite?