Taking someone's virginity isn't easy. Trust me, I know from experience. For reasons unbeknownst to me, I seem to be some kind of magnet for guys who've never been fucked before. These guys aren't necessarily inexperienced in the sexual arena. They've just never met the right person. Or some of them are just beginning to explore their versatile side. And others are just coming to terms with their sexuality and desires all too late in their life.
The first time I've received such a request was during my freshman year in college. A new friend and I had began fooling around innocently. After a few sessions of tonsil hockey and mutual blow-jays, he asked me if I'd be his "first". I believe his exact words were, "I don't want to fuck it up with someone who matters." How very flattering!
Our attempt ended disastrously, to the point that I didn't even get my dick in halfway before he cried out in pain. We didn't ever try again and stopped hooking up shortly after. I've learned from this experience and others, and now I've mastered a technique for preparing a guy for the big moment (more on that later). In fact, this question came to mind after successfully popping a hot college jock's cherry this past Wednesday. His invitation–"You have the perfect dick for it"–was a lot more complimentary…
But enough about me! Now it's your turn to share some stories, whether they be disastrous or totally hot. So tell us, and tell us all the juicy details–have you ever popped someone's cherry?
Photo credit: Corbin Fisher
For photos of Elijah getting his cherry popped, follow the JUMP: