I regret everything about my first time. Wall of text ahead.
I was 19 and epic wasted. I went to my room to pass out. Much to my surprise there was a woman in my bed. I had never seen this woman before. Hell, I couldn't clearly make her out and to this day I have know real idea of what she looked like, just what her shape was like. I was fucking hammered so I take off my clothes down to my undies and get into bed with this woman. For whatever reason we were face to face on our sides. Then she said something about not wanting anything to happen and I probably said something stupid. All the sudden she kissed me and things escalated pretty quickly from that point. I had no idea what I was doing at all. I had only kissed a girl for the first time a few months before this. That's all, I had never even been on a date.
I remember trying to stop her before she slid down on my dick (she was on top). I muttered something about condoms and she said something about not being able to get pregnant so it was ok and that I didn't have to worry.
So fast forward five hours (from what I am told) to me not being able to cum and her asking if I had blown my load. No I said, so she proceeded to blow me until orgasm, which she swallowed. It was so voluminous that I thought maybe I had also peed in her mouth. Turns out it was just a really built up load. She then gets dressed, writes me a thank-you note with her number and leaves.
It was then that I notice that there are other people in the room. 3-4 other people were in there the whole time. One of them I later found out was her boyfriend. They weren't in there maliciously or to set me up. I lived in a frat house and they were in my room shooting the shit when I wondered in and began having sex with this random woman that I found in my bed. My bed was somewhat sheltered from their view but they were only about five feet away so they heard everything and were both witness and hostage to me losing my virginity. Because I was still drunk and had to piss the mother of all pisses I was not terribly embarrassed.
That mother of all pisses I mentioned above was prophetic in one respect. It turns out almost right after the sexy times were over I had the urge to piss a lot. It started to get painful (later after I woke up) and my dick started oozing clear non-piss, non-semen liquid. So the next day I head on over to the university clinic. Keep in mind I am full on freaking out at this point. I had ruined my dick (or my life, AIDS anyone) by carelessly fucking a random woman who quite literally just appeared before me in my bed. Fortunately for me it turned out to be Non-gonococcal urethritis. The clinic doctor was not very nice and told me to let my dickhead get more air (covered in foreskin, probably tmi but you made it this far so what the hell) and to make sure that my girlfriend was bathing regularly. In essence make sure you are both clean before fucking. I showered and yes, cleaned my dick, every day before and since this event.
So why was this mystery woman in my bed? Why did she fuck me? Had she noticed me earlier that evening and plotted to sex me up? Was she somehow planted by my friends who were trying to help me get laid? Nope. She had caught her boyfriend having sex with another woman earlier that night and I was opportunistic revenge sex. She hadn't planned on fucking some dude in front of her boyfriend, I just showed up at the right time. She was only in my room because he was and she went to sleep in my bed because she was tired. That's it.
It was all very very weird, humiliating, exhilarating, scary, and ultimately sad. At the time I couldn't get a normal woman to remotely show interest in me let alone have sex with me. One had to magically appear and fuck me, not because I was me, but because I was a human of the opposite sex in the right place at the right time.
Tl:DR - lost my virginity while drunk to a complete stranger in front of others (including her boyfriend) and got a dick infection. Yay.