Here's mine (spoiler it involves hookers, in Asia)
This happened in Phnom Penh, Cambodia during an 8 month backpacking trip I did when I was 20.
So this was 6 month in the trip, I had a lot miles behind me and I started looking more and more into the nightlife scene since I went through Thailand. Needless to say, I was often out at night and South East Asia is a 'very fun place' to party, and Phnom Penh is one HELL OF A PLACE if you have the guts for it.
Cambodia is like Thailand 20 years ago under acid, it's dirty, rough, exciting.. I loved that place.
So I just arrived by bus there, didn't meet anyone yet so I just took a cheap 5$ hostel room near the Mekong river. And then my sketchiest experienced happened...
I went out. First to one of the girlie bar/pool place to start up the night. The thing is when you are alone in SE Asia, girlie bar are a good option (at least I like it), you never feel alone, girls are easy to talk to even if you don't take one home. You play pool with them, you have fun, have a few drinks, they will of course flirt with you but if you're nice it's just fun and game.
I mean most of the time I spent in Asia in those bars, I usually just had to be nice, pay a few drinks (quite a lot actually) to go home without paying any 'official fees' for a girl. But then again, you have to be open to it, I'm guessing some of you might be repulse a bit.
Any way, I did a few pool game, chatted a few girls and other backpacking guys who were around then decided to move place and head for one of the night club in the center. Heart of Darkness if I recall. Nice place, lots of people, lots of girls (mix of working girls, locals and backpackers). Had a lot of fun. But then shit started to hit the fan.
I was with that girl, Khmer Girl, amazing, told me she was free (yeah right) . Was nice an all but then she told me her bf was there with his friends and if they saw us they would go crazy. Remember, this is Cambodia, shit happened every night, it's not the most safe place in the world, even less in the red district of the capital. I was drunk, she proposed to follow her to her place, I said yes.
We took a moto taxi of some sort and we headed for the suburbs. It was more or less 4am. Arrived at 'her place' , let me tell you.. it was CREEPY. Dirty place. 5 or 6 girls sleeping on the floor, I don;t know for the rest of the house. But I was a drunk and horny 20 years old so I said 'what the hell' and went for it. After all I had seen and done many things during 6 month in Asia, how could this be worse... It was.
My girl went to the toilet and started throwing up. She then passed out on the floor next to the other girls after telling to 'join her' . Well I did join 'them'. I wanted to sleep to be honest, I had no idea where I was or how I could go back to my hostel. But you know what happened when you're spooning a girl after a night out. So I fucked this other chick next to my passed out girl. The one I fucked, I didn;t even say HI to her. No words, nothing. Fucked up. Worst thing was It was without condom (yeah I know).
Then a few hours went by and around 7am, 3 small Cambodian dude wake me up. And trust me, the reality of the situation hit me like Tyson right hook in the face. I was alone, in the outskirts of Phnom Penh, Cambodia, I just fucked a hooker without anything on the floor with 5 other girls around me, and now I had 3 sketchy dude asking me some money in an 'not so nice' manner. They were pretty aggressive about it. Thankfully I had nothing valuable on me. I gave them the 20$ I had, pushed one of them on the side and just walked as confident as I could outside of this shit hole hoping they wouldn't try something more. Then I ran... Man I ran like I never ran in my life. Found a moto taxi, and went back to my hostel... sketchhhyyyyyyyy ......
But then I went out the next night again..
Here is Phnom Penh for the context.