Worst sex I've ever had unfortunately happened during one of my very few one night stands. I was at an upscale bar a few years ago near downtown with some buddies of mine. I walked by these two Hispanic women and one of them pulled me over and asked how a white boy acquired an ass like that. I told them "squats" and then did the booty clap(this is a lie). I hung out with the two of them the rest of the night - Juanita and Arcie. Arcie was way hotter than Juanita, but Juanita was the more aggressive one so I paid more attention to her. The three of us left the club together, and I followed them back to their place. We stopped off at a gas station on the way to their place, and Juanita stuck her head out the window and asked if I had what "they needed"(meaning condoms). I was like, sure do, as I had been wearing a condom all night just in case some random all-out fucking broke out in the middle of the bar.
We ended up back at their place and I don't know how I managed to not realize this was a threesome waiting to happen, but I just thought it was Juanita who was down with it. Arcie went to bed and Juanita and I proceded to go at it there on Arcie's living room floor. I'm pretty sure that her living room substituted as a kiln for cooking clay because I was drenched in sweat by about 5 minutes into it. Juanita was probably in her mid 30s with 25,000 children, and her vagina verified this for me. I have honestly never had my penis in anything this loose before. I couldn't even really tell you for sure whether or not I penetrated her. So it was basically me doing a lot of thrusting and sweating on her and not much orgasming. It probably lasted about 10 minutes before I collapsed from heat exhaustion and then went home.
Then I got pulled over on the way home at 5am and was almost taken to jail because I had a warrant out for my arrest for a JAY WALKING ticket that I never paid. But fortunately it was close enough to the end of the cop's shift that he didn't want to deal with the paperwork, and he let me go.