A few years ago I moved to a new city but hadn’t had any luck dating. One day I matched a girl on some online dating site who immediately started sexting aggressively. Usually I’m the more intimate type, but I thought that I hadn’t had sex in a while so I went for it.

She took the lead and started giving me head, which wasn’t so bad honestly. But I just couldn’t get into it. When she rode me I didn’t get fully limp, but I wasn’t really hard either. At some point she apparently came (or just got bored of my dead fish impression) and I pretty quickly packed my things and left.

That day I learned I really need some type of emotional connection with a person before having sex works for me.

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.

I’m bisexual man, but I lean mostly towards women as my preference. Occasionally, I feel the pull to fool around with some guys, but nothing ever too serious.

I had just gotten out of a 5+ year relationship with a girl that I really liked, but the relationship was extremely unfulfilling sexually. She was a dead fish in bed and I had become bored with run-of-the-mill sex and I wanted to experiment a bit while I was single. I downloaded Tinder, set my preferences to any, and started swiping.

I was honestly just really horny and looking for anybody, male or female, who wanted a quick one night stand and I happened to swipe on a dude’s profile who had such a sexy butt pic as their profile picture that I was convinced it was a girl and didn’t bother to check. We talked a bit and he clarified that he was actually a guy, but that didn’t deter me. I agreed to meet him at a motel he was staying at for work and we could fool around a bit.

To keep a really long story short, I met the guy and he did not look as advertised in the photos. He was much uglier, and did not have a cute ladyboy body. Looked like a stereotypical redneck, complete with mullet and trucker cap. I was disappointed, but I didn’t want to be rude so I stayed. He offered me a drink, which I declined, and then he asked me to take off my clothes so we could start (he was already pantless when I walked in the motel room).

I then had the roughest, most uncomfortable blowjob in my entire life. He was really into giving head and deepthroating. I have climaxed once before during a blowjob so I know what a good one feels like and this guy was not very good at giving them. There was a lot of slobber and gagging involved which kind of took me out of the experience. Had to ask him to be more gentle and use less teeth a few times during the act. Eventually, mercifully, I came in his mouth and I went into the bathroom to wash up and I swear I could not get all the slobber and goop off of my junk. I went home after declining more sex with him, took a 45 minute shower, and tried to scrub my cock clean again. Took like a whole day for it to feel less gross.

He texted me the next day asking if I could “feed him another load” and I blocked him. Absolutely the worst sexual experience of my entire life that I didn’t want to repeat. Really put into perspective all the dead fish sex I had been having with my ex girlfriend and I realized that it wasn’t so bad after all.

Ya ever hear about a sandpaper handjob?

Picture one given by a lady who was almost certainly trained by a Korean masseuse.

Not the ones in LA that are playing up the aesthetic to upcharge you, the legit dudes in Korea who put you down naked on a table and leave you feeling like you’ve been done over with a zester.

I escaped having ma dick completely ripped right off the hilt only through saying I was about to cum and wanted to fuck her first.

I left, picked a sandwich up because I knew I wasn’t in the headspace to cook, sat down on my bed, and just considered my life choices with an ice pack over my jeans.

Let’s see, there was the one I just started anti-depressants and they had unexpected side effects preventing me from getting hard. It was a rather poor sexual experience.

There was the other, which is way more fun, where I befriended a women I was working with. She was lesbian and had a kid. Her last sexual experience with a man was when she was raped. Anyway, she invites me over and after a couple drinks we settle in to watch a movie and start fooling around. I go down on her for a while and then she has me move towards normal sex. Literally ten seconds after I enter her, she excuses herself and goes to the bathroom to throw up. She thought she was going to be okay with it, but had more of a reaction than she expected.

Eventually, she comes back out and apologizes. I didn’t mind though, we ended up just cuddling watching the movie until we fell asleep. 10/10, would sleep with a lesbian again.

We stayed friends for a while, I introduced her to one of my other friends and she dated them for a while. We hooked up a second time a few years later.

There was another one that didn’t understand her kinks or communication yet. She would say things to try and get me jealous. She would also constantly say no or stop during sex and then get mad or frustrated when I would stop. It ended up just being a little awkward, but we were young and dumb. Too young to understand discussing what she wanted before starting sex and agreeing on a safe word.

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 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.

An attempted handjob by a woman from a country where circumcision is rare, so she went for the death grip.

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’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.

I had sex with a friend who later came out as a lesbian. It was uninspired. We’re still friends but that was a single time and never again.