Senior year of high school, and I'm on a mutual-yet-strained break with my girlfriend of two and a half years. I'd only just realized that maybe other people on the planet could find me attractive (the acne was clearing up, you see...), and wanted to try my hand at flirting. This cute Korean gal from my theater class reciprocates my advances, making me feel like a king. We flirt for a few weeks, but one day we decide to "hang out" on a Sunday evening, and so I brought her to my home near campus. I had to have her back to her dorm by seven or eight p.m., so we tried to cut right to the chase. Problem: Dad is wandering the house, and wants me to take care of some chores. We wind up not getting an opportunity until right before I have to take her back. She pulls me into the bathroom, bends over the sink, and pulls down her pants. This signals my first encounter in my young life with a woman who opted not to shave. I was not disgusted or repulsed, but definitely surprised. Problem #2: Even with both of us angling and what have you, I was having immense problems getting past the hair barrier. A minute or two of fumbling around, and I think I've finally made some headway and drive it home. This was bad, because what would have been a steady push became an aggressive thrust due to the momentum required. Next thing I know, I'm unceremoniously balls deep, with her pressed up against the sink. If there was any confusion on my part as to whether she was a virgin up until that point, it was immediately dispelled by her howl of pain. After that, it's all a blur of me pulling out, pulling my pants up, and helping her--hunched over, whimpering--to my car. We manage to drop her off at the dorm moments later, she shuffles inside, and I bolt. Returning home, I go upstairs, and realize I still have a bloody condom on in my boxers. Mortified, I whip off all my clothes and hop into a very hot bath, because the shock of having just HURT somebody so grievously with my dick was mortifying. Halfway through the scrubbing, the poor girl calls me and cries over the phone, wondering why it hurt so much, and what the fuck is with all the blood. I repeatedly say I'm sorry, and that I'll make it up to her the next day at class, then hang up the phone. We don't speak for a week, because I can hardly look her in the face. She comes up to me the week after and says that everything is okay, and she wants to try again. At this juncture I had gone back to my girlfriend and begged her to mutually cancel the break, and that I would never leave, because I was now convinced my dick was an instrument of evil adultery. This being the case, I declined the sex, and we never spoke again. I feel like an absolute bastard about the situation to the this day. : /

TL;DR: Went on break with girlfriend, hooked up with petite Korean girl, and one-hit KO'd her vagina. Blood and regret ensue.