Worst sex you've ever had

[Gnome72141]

Worst sex I ever had was with my abusive ex-wife.

First, we used condoms, which caused great pain for me and I could never feel anything at all. It was literally zero feeling.

Second, she would come after two thrusts every time, then she would push me off and told me to get out of her, so I never came, ever.

Third, she would have me eat her out every night, which I actually enjoyed, but she refused to do anything for me because she said oral sex was gross(?????).

But it was made up for when I met my current wife.

[rudolfm]

Hard to say what was worst.
The dead fish who just expected to lie on her back and let my do everything.
The lady I started eating out, then needed the toilet and afterwards tasted like old piss.
The lady I started eating out, had a hairy ass with lumps of shit clinging on to those hairs.
The lady who farted while I rimmed her.
Those who gave me a STD as a reminder.

And even then, I never had one vomit during a blowjob or shit during anal sex. Life can always get worse. Sorry, but you asked for this.

[mysweetie61]

I've only had long term relationships my entire life be it 6 months to 5 years. Back when I was in my late 20's I had my only relationship where I picked up this gorgeous woman working in a boutique woman's clothing store. I walked past the store and noticed her as she also noticed me. I was in line at the mall coffee shop when she got in line behind me. We chatted and I asked if she wanted to get together after she was done. She agreed, I gave her my address and she showed up 3 hours later.
We chatted and had a drink then ended up in bed. She was as gorgeous as they came, early 20's, nice fit body, silky long hair, B sized breasts with long nipples and Chinese French. I could get hard with her so I was only able to get a soft dick inside her pussy. She never came but I cum inside he. It was ever so embarrassing to have given her a soft dick.
It ended up being my only one night stand.

[Openyoureyez89]

After a night out I regretfully went home with a friends sister. One of those think with your dick now, think with your head later moments. She wasn’t even attractive. Not ugly but stick thin and no tits and a very plain face. Back at her place we got into it. The making out was fine but she went to go down on me and inserted my cock into her mouth and sort of sucked on it like a pacifier. I thought she’d work up to other techniques but didn’t. Just kept sucking it like she was sucking her thumb. Then I laid her on the bed and stuck it in missionary and fucked her a while and she was so unresponsive and made no sound. It was awkward so I asked her to get on top but she said no just keep going. I eventually came and we fell asleep. The next morning as I was leaving she said how she wanted this for so long and was looking forward to seeing where it goes. I had to let her down that it was a one time thing. She cried. Her brother and I drifted apart basically because I was avoiding her. So that’s probably the worst sex I’ve had.

But I can’t claim to be perfect. There was a night I was able to land a gorgeous girl at a bar when I was in my early 20s. I’d only had sex with a previous girlfriend and didn’t really have any skills at it. This girl was so out of my league I couldn’t believe we were going to fuck. Well she straddled me and slid my cock in and between my hands on her ass, her tits in my face and her pussy enveloping my cock it was all too much and after maybe twenty seconds I had to push her off of me as I came. And it all happened so fast I couldn’t maneuver myself so I just sat there jerking cum onto my stomach. She wasn’t comforting at all about it like a girl typically would be. She was disappointed and basically asked me to leave. Humiliating.

[winston optic beer]

I only once had sex that I didn't enjoy.

It happened with my first girlfriend as we were breaking up. I'd found someone else who was much better in bed. After avoiding sex for years, she seduced me by laying me down on the floor and getting on top to fuck. The only words she said were "there's nothing she can do for you that I can't." Sadly, I knew that just wasn't true. Her belated attempts to win me back seemed pathetic. Too little, too late. I couldn't hide disguise my disgust. It was the last time.

[explorer98]

But I think this one wins out!

This happened 20-odd years ago and was the result of a lot of online exchange between me and another guy who was proudly 'training' his submissive.

We'd had a lot of correspondence and clearly had a lot in common. He was obviously far more experienced (in R/L) than me and to a far more extreme extent in that not only was he sharing her, he was actively involved in group activities and if I say they weren't walking their dogs, you'll perhaps get the memo?

An occasion emerged when we'd have the opportunity to meet. Sounds strange perhaps but C & K lived in very North Wales (by the Electric Mountain) and I live in very central England (very close to the last big power station to recently close).

By UK standards, it's a bit of a trek!

As things happened, I was working in Wales and could take a different route back which meant we could meet.

C was all over it and well up for it but it wasn't all plain sailing (or driving!). Traffic was bad, I was delayed, nearly binned the car at one point and by the time I finally arrived, I really wasn't in the mood for much.

More unfortunately than that, when I met K, I really didn't fancy her either. I don't consider myself a snob particularly but her place was more than a bit squalid (which also dampened things considerably) but for her part, she'd been kept (literally) hanging around for quite a while and it was pretty sure she'd lost what interest she had too.

Nonetheless, C was still very keen to get things cooking, insisting that she address me as Sir ..... (which I find really cringey!) and took great delight in stripping her naked for me.

Next fail: K had very obviously spent a lot of time in shoes far too tight or small and one thing that really kills the thrill for me is damaged/deformed feet!! Oh well, man up....

So she's naked between us and C is doing all kinds of rude things to her. I will say K had very nice tits but when I picked on up by her nipple, she really didn't like that and made that abundantly clear. Another downer!!

"Do you want a condom?" I was asked. Now things were really starting to feel contrived. As if it wasn't bad enough already, I knew there was very little chance of me making use of such a thing and politely declined, pointing out that my cock was already buried in K's mouth while C fucked her from behind.

What really fucked things up big time was his bloody black Labrador, constantly fussing around the whole thing and very clearly desperate to get involved!!

I can't remember clearly past that point other than the dog didn't get a go and neither did I! I really wasn't interested at all by then and I think things just gently crumbled as politely as we could manage and I left.

What I did find ridiculously ironic was that many years later, LinkedIn suggested K as someone I might like to connect with!! Considering we'd never exchanged any correspondence or communication and LinkedIn only (theoretically) 'knows' my personal and professional emails (neither of which I'd used for 'private' purposes), I thought that really showed the extent to which social media secretly mines its way into your life and those around you, no matter how tenous the connection!!

[Leviticus59]

When my wife and I were swinging we had some close lifestyle friends who were another married couple. They were so much fun the four of us were pretty much exclusive for several years. We found out much later that they were swinging for all the wrong reasons. Apparently the wife had gradually shut down sexually and husband was staring a dead bedroom right in the face. I don't know whether he had a special insight into her psyche or just took a shot in the dark, but somehow he talked her into trying swinging. She got to liking it and it broke their bedroom wide open.

But it always made him slightly jealous watching her get fucked by other men (me mostly). She and I clicked well and were great in bed together, quite a bit better, I later found out, than she was with her own husband. After several years of that he couldn't stand it any longer and told her to dial her responsiveness back a little.

She did, and over a several month period she went from being one of the best fucks I ever had to absolutely the worst. Last couple of times I fucked her she laid there completely dead fish, totally unresponsive, dead quiet, with her head turned to the side so I couldn't even see her face, much less kiss her. That last time finally disgusted me so much I was tempted to roll her over, grudge fuck her in the ass, then get up and wipe my dick on the curtains and leave.

Instead, I went to the husband and said, listen, buddy, I just can't do her anymore. She's turned into the worst fuck I ever had. Terribly sorry, but we're just going to have to move on. That made the husband absolutely furious, because he knew that if we left the friendship his sex life with her would promptly die, which it did.

Man, what a flame out. A completely dead fish swinger chick and a hopping mad husband. The worst of the worst.

[explorer98]

Originally Posted by Leviticus59

When my wife and I were swinging we had some close lifestyle friends who were another married couple. They were so much fun the four of us were pretty much exclusive for several years. We found out much later that they were swinging for all the wrong reasons. Apparently the wife had gradually shut down sexually and husband was staring a dead bedroom right in the face. I don't know whether he had a special insight into her psyche or just took a shot in the dark, but somehow he talked her into trying swinging. She got to liking it and it broke their bedroom wide open.

But it always made him slightly jealous watching her get fucked by other men (me mostly). She and I clicked well and were great in bed together, quite a bit better, I later found out, than she was with her own husband. After several years of that he couldn't stand it any longer and told her to dial her responsiveness back a little.

She did, and over a several month period she went from being one of the best fucks I ever had to absolutely the worst. Last couple of times I fucked her she laid there completely dead fish, totally unresponsive, dead quiet, with her head turned to the side so I couldn't even see her face, much less kiss her. That last time finally disgusted me so much I was tempted to roll her over, grudge fuck her in the ass, then get up and wipe my dick on the curtains and leave.

Instead, I went to the husband and said, listen, buddy, I just can't do her anymore. She's turned into the worst fuck I ever had. Terribly sorry, but we're just going to have to move on. That made the husband absolutely furious, because he knew that if we left the friendship his sex life with her would promptly die, which it did.

Man, what a flame out. A completely dead fish swinger chick and a hopping mad husband. The worst of the worst.

As the saying goes; "Be careful what you wish for..."!! Maybe nobody told him that??!!

[Xico]

As a favour to a friend I agreed to go on a double date with him, his his much older fuck buddy and her best mate.
The blind date was Michelle, about 15 years older than me, definitely not my type, and completely nuts with a wacky sense of humour. Anyways to cut a long story short I ended up back at Michelles and thought why not.
Body wise she was actually OK but she just wouldnt shut the fuck up, talking all the time I was fucking her. Telling me how good I was, i was so big, that felt really good, oh yes baby, keep giving it to me whilst at same time lying there like a dead fish. It was so off putting that my dick went soft and slid out of her.
She then proceeded to try and resurrect it with a blow job. At least that kept her quiet!!!

[Gnome72141]

Originally Posted by Xico

The blind date was Michelle, about 15 years older than me, definitely not my type, and completely nuts with a wacky sense of humour. Anyways to cut a long story short I ended up back at Michelles and thought why not.
Body wise she was actually OK but she just wouldnt shut the fuck up, talking all the time I was fucking her. Telling me how good I was, i was so big, that felt really good, oh yes baby, keep giving it to me whilst at same time lying there like a dead fish.

She sounds like a DREAM to me, actually, except the dead fish thing (but my wife does that often, but it doesn't bother me because I can feel her cum 12+ times every time we do it).