My first threeway.

Holy shit, never, ever try and play with a bi/lesbian couple if you're a straight guy lol.

This was ages ago. Back in the eighties still, if only barely.

I met a girl. We became friends. She got flirty, and I returned it. Now, she was honest pretty early on, once we both realized there was some sexual energy there. She told me she was with someone, and that the someone was also a girl.

I figured that was it. End of story, right?

Nope, the girl is bi, though her partner wasn't exactly into non monogamy. But we were first, and was cool with it not going anywhere.

So, we hang out. Turns out her partner is pretty damn cool. Butch as hell, but not prone to the machismo you sometimes run into. Which, the partner ended up being trans, but back then that wasn't a thing in anyone's awareness. At the time, she was a butch lesbian.

Anyway, ignoring that, we all get along well, so I become their beard. When they needed a guy to "date" to keep their family off their backs, or whatever, I would step in. Went to prom with the partner even.

Turns out, we all got along well enough that the partner was willing to open things up and see if a guy in the bedroom could satisfy the bi girl, without bothering the partner. And, I was the one they both trusted. So, it happened.

I guess the easiest way to cover it is to say that there's only so many things you can do when one person out of the three simply can not handle contact with a penis, and is also not willing to have anyone go down on them. It meant there was always someone left out. I mean, we tried. But it amounted to taking turns, and the partner couldn't really handle watching.

We ended up trying what I've seen called a Roman chair, and that kinda worked okay, but it was so damn awkward with me and the partner kind of looking at each other as the bi girl was between us. Like, if we'd been able to touch each other, maybe the awkward would have been gone, but we tried kissing and it was a hard no for the partner, and not fun for me. Any kind of gentle shoulder touching was out too.

We could hug each other with clothes on, even give pecks on the cheek when we'd say goodbye after hanging out, but with the clothes off, neither of us was down for much in the way of contact. I would have been fine with casual touch, maybe some hugging, or even a high five lol. But I didn't want to grope him (fuck it, the dude transitioned, and trying to not call him him is annoying, even though this was ages ago), no matter how nice his tits and ass were. It just felt wrong to grope my buddy. And I had zero interest in his vag, which was still more interest than he had in it.

So me and him were just each in a hole (him via strap on) kind of wanting the whole thing to be over lol. The girl had some fun, but after I had to admit there was no way in hell I could come, she started feeling awkward too lol. Like, there I am in her ass, doing my best to stay hard so she can have this experience, and her partner is just going through the motions for the same reason, and once she realized that, she felt weird as hell.

Tbh, I've never liked threesomes. We tried a couple of other times, and it was better than that one, if only by virtue of knowing what was absolutely not worth trying. But even with other people over the years, they all end up disappointing unless it's two people taking care of one, without trying to mix things up.

But holy shit, that first one was just horrible lol. I've seen guys talk about the fantasy of being with that kind of couple, and I can't help but laugh. The chances of a lesbian being all chill with a guy in the situation are pretty damn low. And there's no such thing as good sex when one out of three people would rather it not be happening the way it is.

Which, gods damn, my buddy there tried so hard to do what he thought was right by his girlfriend. Later on, he tried to be open for some contact with me, even tried going down on me. Neither of us could handle that lol. I couldn't stay hard, and he couldn't do more than take in just the tip for a second. It was kinda hilarious after the fact. We still joke about it.

He couldn't handle either of us going down on him. We didn't have a word for it then, but the dysphoria was just too powerful. It wasn't about me being a guy, it was him being so out of connection with his genitals because they were the wrong genitals that any contact was just pure distress. Even hands were too much.

We only tried a few times as a threesome before calling it a failed experiment. Then a couple of times with just me and the girl, with him having done some preliminaries and then just watching. That was almost as awkward for me because it felt like him being left out was wrong, and it didn't work well for either of them.

But none of the other fails were as bad as the first lol. I'd call it a clusterfuck if any of the fucking had been worthy of the 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 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.

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.

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.

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.

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 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.

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. 🤢

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 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

95% I rarely relax

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.

Anal

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.