I took two women home from the bar one night and I guess they were fighting because they kept biting each other’s clits.

Or maybe it was establishing dominance but either way it was just kind of awkward.

I had a partner for eight years. We met when we were both 31. She was my first monogamous relationship theretofore because I decided to give monogamy a try. She was utterly, screamingly boring in bed. There was nothing else notably wrong with the relationship, except for her unwillingness to communicate on anything beyond household, workaday topics. No oral (give or receive), no anal, not into foreplay, and she would just lay there. But no conflicts either. There was the advantage of she was always willing and ready to go without any foreplay or lube. She got off and claimed she was absolutely sexually satisfied. Sex wasn’t even fun in the context of Free Use, which is a kink I enjoy. I tried to engage her in all kinds of Gottman Method relationship work, but she bluntly and explicitly refused.

At one point early in our relationship, she moved and clamped her vagina in a way that was quite enjoyable. “Honey, that was great! Please do that more.” And for the rest of our relationship, any such complement was a sure-fire way to make sure it would never happen again. After eight years of nearly daily, invariably terrible sex, I stopped approaching her sex for three weeks. She never said a thing. On day 22, I broke up with her, and she was absolutely gobsmacked, claimed that I was throwing away eight years of great history. She hadn’t even noticed that there had been no sex for three weeks.

Worst was the first, I had no clue what I was doing and I’m pretty sure she couldn’t have enjoyed it. Despite being in similar friend groups, we both pretended it never happened and never spoke of it again. Now decades later we ran into each other. To make it worse, she recognized me but had to introduce herself to me. All that cringe came flooding back

I met a girl on tinder and we talked for a while. We lived kinda far away, so we were just texting a bit. She only had very cryptic pictures, and she only sent me weird pictures. So i assumed she is not very pretty, self conscious, or overweight. I had some time off and she asked me if she wanted to come over. So the fastest way to get over there was by car and then hipping on a car train thingy and drive the rest again. But i agreed, seems fun and i didn’t have anything better to do. On the way she was texting me if i would really show up, and i said yes. She asked if i knew that dhe wasn’t thin. And i said i kinda assumed so. She then sent me the first almost normal picture where you could see that she was in fact overweight. When i arrived there, she was very very overweight. We talked for a bit and it was kinda miserable. She’s the kind of person who hardly lets you finish a sentence, because she wants to tell something. At some point it was too late for my train, so i started to make out with her, and i literally thought: at least she’s not talking anymore. We had sex later and it was not great at all, there was just too much of her and she was out of breath before we even made it to the bedroom. I was so glad when it was done, and she then told me that she thinks she snores and i need to wake her up when she does. She snored like i have never heard before, and i didn’t want to wake her up. I had to stay there until 9am and it was miserable. She asked me if i wanted to stay for lunch, and i was just waiting for the clock to jump to 9am so i could bolt, i only slept for like half an hour and had like 3 hours to drive home.

I’m old and unlucky enough to have had many bad sexual experiences, for better or for worse. Unfortunately, by modern standards, I’ve definitely had some questionable experiences where I was taken advantage of (i.e. intoxicated, emotionally vulnerable, etc) and which would likely fall into the non-consensual category these days, so I’ll leave those out, since they were the worst by far.

I’ve had plenty of bad experiences that were totally on me, so for the sake of my own ego, I’m going to disqualify those.

The worse consensual experience I can recall at the moment was awkward and a bit weird. The guy was persistent and braggadocios while pursuing me. He was nice looking and we got along fine online and in phone calls, so when the conversation came up about meeting up for nothing serious, I was okay with that.

We hung out awhile before getting intimate and he was nice enough, nothing seemed off. It’s almost a stretch to call what we did together “sex”, though. He wasn’t able to get an erection. Not a problem honestly, there are still plenty of ways for two guys to have fun. We basically just snuggled together in bed.

At a certain point, though, he just started saying weird or off the wall stuff. I do not know if he had taken some drugs or if he was experiencing a mental health episode. It was like he was hallucinating that he could see the night sky even though we were indoors in his room with the curtains pulled, since he kept talking about how pretty the moon was and things of that nature. And he would ask me the same questions over and over so I know for sure something wasn’t quite right.

Was about to go down on a girl when the smell of her snatch stopped me. Her kitty straight up smelled like a dirty litter box. 🤢