Ask Lemmy

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.

Anal

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.

Gonna preface this by saying this is not my worst, or really even a bad experience. We were in a 69 with her on top. I was getting into it and wrapped my arms around her waist, squeezing her down on me. This was just the right amount of pressure to squeak a little fart out of her, which made me giggle while still firmly planting my face in the fun zone. The sensation of me giggling made her tense up, ripping a fat one right in my face. I pulled my face away so I could laugh harder, but that made me gasp through my mouth, and I cough while yelling "OH GOD IT'S IN MY MOUTH!" We are both dying from laughing so hard, but a moment later she suddenly says "LET ME UP" in a really panicked tone and runs to the bathroom. I sat up so I could ask if she was OK, and felt a drip from my beard. I said "wow babe you left me a little treat, you were really wet!" She screams through the door "OH MY GOD DON'T LICK THAT!" She had laughed so hard that she peed on my face.

I was platonic friends with a gal for several months and one day at a brunch she asked me why I never made a move on her

I told her I thought she wasn't interested to be polite, even though the truth was that I wasn't very interested. I didn't feel a strong potential for a romantic relationship, but I didn't want her to feel bad

Something personality wise didn't feel right in a relationship, but felt right to hang out with.

She told me she was interested.

I decided that I couldn't tell the future and invited her back to my place after.

We kissed for the first time, but it kind of confirmed that I wasn't super into her, and I thought I felt that she wasn't into me.

I asked her if she enjoyed the kiss, and she said "yes, of course, did you?"

So I said yes because I didn't want her to feel embarrassed.

Things progressed, and I kept checking in, and she kept telling me that she was into it, and I thought maybe sometimes attraction doesn't click right away, but we're good friends and she seemed so into it so maybe it'll be better later if our relationship progresses.

We had maybe the most awkward sex I've ever had, neither of us really dug the other's preferred positions and it was just strange in a way I've never experienced.

From my side I felt magnetically repulsed by her. That's as close a description as I can imagine.

So afterward, she said "You know I kind of didn't want to sleep with you".

I was immediately confused and horrified. I asked her why she brought it up in the first place and repeatedly told me she was into it the maybe dozen times I asked her to confirm during the deed.

She said she thought I had wanted to get together with her for a while so she went along with it even though the sex made her very uncomfortable and she didn't enjoy it. By this point I was in utter disbelief, since I had just been assuming the awkwardness was one-sided since she kept telling me she was into it, having a great time, wanted to try _____.

I confessed that I had thought the same thing, and it was a bit of a relief for both of us at the end.

We didn't have a huge laugh over it, but we didn't hate each other afterward and still hung out.

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.

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'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.

My landlady had issues. Having sex with her was frustrating because she wanted annoyingly specific things and provided very little feedback. She was also very controlling despite trying to avoid being in control. I think the fact I was renting out a room in her house made her act that way. We tried it about four times, but I only climaxed once.

I was dating this girl, was going well. We fooled around, had a lovely time. She just seemed cooler than me in many ways, had cool hobbies, hung out with cool people, I was kinda feeling like I scored.

Then one day 3 weeks later I did. For some reason she didn’t want to on her bed, so instead we attempted the act on the living room couch, she had roommates. Her shirt came off exposing her back and it just didn’t look right, I can’t explain it, was like her ribs were sunken in like a corset and her backbone was curved in this scoliosis kinda way. I was confused and my member went a bit limp. I think she could tell, but we went ahead anyway. Then the couch cushions just kept sinking and getting in the way. Me with a half limp dick and these awkward positions, neither of us really feeling it and yet we still continued on. The whole thing just felt pathetic.

We hung out a few times after, but it always felt like the ending of 1984, where the couple have all of that vibrant life sucked out of them. The relationship was over shortly thereafter.

A decade later, I haven’t seen her since. We’re still friends on Facebook.

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