The worst I'm willing to divulge? I was young (17) and foolish with my first girlfriend. She was very shy and a bit prudish, but for the few months we had been dating I had opened her up from never having kissed a boy to much more. But still no sex, which I was becoming less fine with as time went on. For summer vacation I convinced my parents to let her come along, and stay with me in our own room. This was it, I thought, it's finally going to happen. First night we come back from dinner, where we had a few glasses of wine, and things were getting pretty heavy. She finally says "I think I'm ready", and I immediately jump up and run to the bathroom to get ready. Everything's set and I'm fully in 'go mode', got her clothes off as fast as my shaky teenage boy hands could, and what do I find? Blood, blood everywhere. Apparently her period had come a day early. I distinctly remember every part of what came next, whether I'd like to or not. My hormone soaked brain went into overdrive. "Hey, it's no so bad, we can just clean up and keep going." She turned to me and said "Oh fuck, I'm so sorry, I can't handle the blood." Always the strategist, I tried to think of the ways to not stay a virgin for the rest of my high school career. "Well, what if we ... if I, well I have some lube here, if I ... used the other hole instead?" As quickly as the words left my lips I realized what I had done. I had asked this girl, on her first time ever, for anal. She just gave me this blank stare, as if I had killed her dog. I ended up sleeping in my parents room that night, and even though we ended up having sex later there was no end to the shit I received for that.