Worst: First time with my then-boyfriend, we were in a very dark room. I went down on him and he seemed to enjoy when I was using a fair bit of suction on him, so I kept doing it. Approximately 20 minutes-ish later, as he was almost about to orgasm, I started tasting blood. Like, it was coating my mouth bloody-blood.
I panicked and told him I tasted blood. He turned the bedside lamp on and saw that my entire lower-face and his shaft was covered in blood. He started freaking out, lost his erection within seconds but we then realised it was not his genitals but my lips that was bleeding; I am a lip biter and had injured my lips. The suction seemed to have caused bleeding, which mixed with all the other fluids, seemed like a heck of a lot of blood. – AdorkableGeekster
Best: With a former classmate, nearly ten years after graduating and it was rushed, rough, and awesome.
Worst: Found out that he lived with his mom so we had sex while parked along a deserted road. Well, attempted to but his truck was rather small for both of us so he opened the passenger door and long story short.. I fell out head first.. – nativehoneybaby