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A few friends and I started a Fight Club in high school. It was the time the movie came out and we really went for it hard. It started with fighting each other then got to be as much as a dozen people. We wanted to expand and do hardcore anti-establishment/nihilistic shit but it ended up only being the original four of us going that route. Mostly elaborate vandalism, fucking with people, graffiti, theft etc.
I had a surge of confidence and started hooking up with girls like crazy. I would do not-so-nice things to them, basically degrade them, as a calling card and to prove I didn't give a fuck.
One girl was a virgin and sort of a goody-good type.One night we were going to have sex for her first time and I went straight for anal. She didn't know what to do but keep quiet. I then went to her pussy, I was rock hard thinking about ass-to-pussy being her first time. I ended up cumming in her ass and left my dick in there until I got soft, then I pissed in her ass (harder than it sounds).
I never said anything and she just ran to the bathroom. I eventually left and she avoided me afterwards. I of course told everyone I pissfucked her ass and was pretty cruel about it, to this day I can't explain my actions and mentality back then.
I am now in finances with a wife and two kids and that's all behind me. But I saw this girl just three months ago and she was married and pregnant. It was awkward as fuck and her husband left the line we were in to grab something and she simply told me she never wants to see me again and that I was a piece of shit. All I did was nod and say "I know".
I have dozens of fucked up stories from that period of my life. I'm basically numb to it but the things we did are unexplainable. Oddly enough, of the other three friends, one is a doctor, one is an engineer with his own lucrative firm, and the other is a high school teacher. We still see each other whenever we are all back home, which isn't often.