In my single-in-my-50s years, I discovered that a week of flirting online with a woman in her 40s/50s was generally enough to get her into my bed.

One lady was incredibly enthusiastic online, very flirty, lots of sex talk, can’t wait for Friday. She said she lived with her mother, sister and daughter, and sister could be abusive, so we agreed I’d drive to hers, pick her up, drive back to mine. I did this, although driving into and out of London was a pain.

Once back at mine we sat on the sofa and started drinking wine. Then she said her phone was ringing, went out of the room, came back five minutes later “it’s all kicked off at home, I have to go”. I was convinced there hadn’t been a phone call and she had cold feet. (Yes, she’s entitled to, but I prefer not to be lied to.) Ever the gentleman, I said I’d drive her home, no hard feelings. (See what I did there?)

So the worst sex was no sex, although I might have escaped easily from a woman with too many issues to be tangled up with.

But the best thing was as we drove away from my house, before we got to the end of the street, my car had a puncture. So she had to get a taxi, which she whined about a bit, as she “worked freelance” and had very little money. But I didn’t offer to pay for it. Bye then.

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.

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.

Younger years
 

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.

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.

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.

There's been a few...
 

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!!

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??!!

Too much happy talk!!!!
 

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!!!

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).

yes
 

Every girl as a young man, who had sex thinking they were doing me a favor...in their efforts to bag a man for marriage/paycheck.

It was soooo insulting to me......so i fucked them hard and dumped them... don't need patronizing sex....

Yeah, I've had some 'bad sex' over the years. But what I've learned is...we all learn what we are 'supposed to do' basically by doing it. Thing is, different people like different things, and that first time we're all in the dark about what our new partner will like and what they might hate. I remember the first time I had sex with the woman who would later become my first wife, when we first kissed I went in for a slow and steamy kiss and she went for an absolutely aggressive 'stick her tongue down my throat' approach. Turns out I was only the second person she had ever been with and the first guy kissed just like that. Turned out she liked the way I kissed better, but she didn't know that until I kissed her; and from then on, that's how she kissed too.

I just have to think...lots of these 'bad sex' stories probably have something like that as the underlying reason.

I once had sex with a woman who in the middle of a long snog bit my tongue. I recoiled and it must have been obvious I didn’t like it. She did it again later.

This was the only negative to an otherwise great experience. She was a stunningly beautiful woman of Persian extraction.

Worst I ever had was with my best friend growing up. She and I had been friends since junior school, by the time we were late teens we’d had the occasional drunken kiss and famously she jerked me off one New Year’s Eve (I say famously because she did it in a room full of people we thought were all asleep but one friend was awake and watching…)


Anyway, by the time we were mid twenties and working we still maintained our friendship and one drunken summer’s afternoon we ended up at my place , making out and generally being naughty. As with previous occasions I was playing with her tits and she was jerking me off. I stopped her and told her I wanted something else.

I stripper her down, found a condom and slipped inside her. Unfortunately, the build up of the previous 20 mins being jerked off meant I came as soon as I was inside her. I tried to disguise it, but almost immediately went soft. All I could do was apologise and offer to help her out another way, which she declined and we ended up just sleeping.

We never did anything else together like that, so if she remembers it at all she will have the abiding memory that I’m rubbish in bed (I’m fairly certain I’m not)

[QUOTE=SixPointFive;
I stripper her down, found a condom and slipped inside her. Unfortunately, the build up of the previous 20 mins being jerked off meant I came as soon as I was inside her. I tried to disguise it, but almost immediately went soft. All I could do was apologise and offer to help her out another way, which she declined and we ended up just sleeping.

We never did anything else together like that, so if she remembers it at all she will have the abiding memory that I’m rubbish in bed (I’m fairly certain I’m not)[/QUOTE]

I had a similar situation however I had always dreamed of initiating a sexual encounter with her as teens but never dared because we were such close “friends” for many years she was still a virgin, pastors daughter, family friend etc.

Like you when it finally happened we had been teasing and playing around for so long that night and we finally stepped over that invisible line and took it up a level.
Looking me in the eye she told me she wanted me to be her first….THEN, I blew my load in about 3 minutes…, in my head I was thinking you can’t be serious this is all I ever wanted and 3 minutes was all I lasted…!

We immediately returned to “friend status” and she said it was nice we shared that moment together… bla bla bla.. I was humiliated. Emphasis being on “a MOMENT!”

Decades later we actually met and one thing leads to another and we finally got to really enjoy some crazy fun exciting exhausting sex together.

When I mentioned the first time taking her verginity was so embarrassingly bad she remarked “that it was always the benchmark sex she was never able to find again with a partner and always wished we had taken it further than friends back then…” WHAT?!
I spent decades wishing for a do-over.

So when that opportunity came back around we did it multiple times a day for 7 years… haha 😛

I assume, for most men the worst sex they ever had was the last time they managed to convince their wife to have sex.

Ooof, that is a very heavy and loaded statement, but I understand what you are saying 100%. Thankfully, my wife is the opposite and she still wants sex twice a day after 20+ years, but I know people in the situation you described (as well as the reverse).

Well these days thats the story of my life. Three years back, somehow my wife got the idea that I dont deserve her and have done nothing for her. Although I have provided her with all the luxuries of life. Anyway so three years back she decided to punish me by denying me sex and not even a kiss was allowed. Even on birthdays and anniversaries all I get is a sisterly side hug. Our last sex session prior to this was the worst experiance of my life. Neither of us had any desire to do it and she just laid down like a log. In less than two minutes it was all over.
What made is really worst was the fact that she still is the most beautiful and desirable woman I have ever seen and her sexual performance can put the best pornstar to shame. And all I got was a pathetic and pitiful session

Not for me. We don't do it very often, maybe 4 or 5 times a year these days, but it's still always fantastic

Truer words have seldom been spoken!
 

Well said, rudolfm. If I had the courage, I'd have that tattooed on my person!

In 33 years of marriage, my wife has "rocked my world" only once. The other sporadic occasions resembled something akin to necrophaelic coitus. Whilst other husbands might tend to bask in the afterglow of sex in the loving arms of their wives, I've wandered off to a toilet to weep post-coitus more times than I care to admit.

Was it worth it?
 

I’ll take a different way, you can tell me if off topic. I had posted this under a different thread years ago.

I had broken up with my long term girlfriend, right before we were going to get engaged. I was fresh out of college, 22. It was tough going, but after months, I needed to get laid bad.

I had a two bedroom apartment and held a party with friends one Friday night. There was a girl I really liked, we had been dating for a month, but we had only gone as far as kissing. I was hoping maybe this could be the night.

Then, she told me she couldn’t make my party. A bunch of other friends, male and female attended. The girl I was interested in, one of her friends attended who I didn’t know, but she was very friendly toward me.

Anyway, two of my other female friends had too much to drink so I had them stay over and had them use the other bedroom. The new girl who had been friendly to me decided to stay also. I told her she could stay in my room, and I’d sleep on the couch. How proper of me, LOL. She kept saying “you can stay in your room too”. I was a bit dense, but it finally clicked.

It wasn’t too long before she had her hand on my cock and I was fingering her pussy. She asked me to fuck her, and I didn’t need to be asked twice. Thoughts of the girl I liked were out of my mind. This girl was very vocal, screaming “FUCK ME” over and over. Thinking back, did she just like saying it, or was I not fucking her good enough?

Fast forward to morning. My other two female friends were in the kitchen getting breakfast. I acted like nothing happened. They both looked at me and told me I was a pig for fucking the other girl (I had hoped no one heard), what about them girl I liked? I was a man wh*r*, and that the girl I fucked didn’t care about me.

The girl I fucked? I was just a “notch on her lipstick case” so to speak.

The girl I liked? She found out real quick what happened and wanted nothing to do with me.

So, that one fuck cost me a girlfriend, two other friends never viewed me the same way, and I didn’t get a relationship with the girl I fucked. To be honest I don’t know how my fuck measured up against the other guys she had.

That few minutes ended up being the worst sex for what it cost me.

Bank teller
 

Worked on this girl for 2 years and finally sealed the deal. She was a teller at my bank. Beautiful face and body with clothes on; mahogany hair, part Cherokee Indian, and a gorgeous shape dressed, but pancake boobs, a p-ssy that smiled a little stanky and felt like you just stuck your c-ck in a mayonnaise jar. And to top it off, she just lay there with no emotion or game. One and done was enough for me.

It smiled? 😁😆😅

I would say that I need to Preview my posts a little more closely. LMAO :):D

Bankteller
 

Myself had 2 Banktellers. I must say both were exactly like u said, top dressed but deadfish sex :(

Was she shaved?

I got far too drunk at a party and was flirting with a girl I knew for years who was also drunk. She was a rather large girl, so much fun, I loved her company but I had never really considered sleeping with her before, but you know what happens when you and “Willy” get to drinkin’.

Well we end up kissing on a couch together at the end of the night she starts to get Willy out to play and is sucking me off. She suggests going to her room so off we go losing clothes along the way we get to the bedroom and I have a raging hard on she lays down and I climb on top and get a whiff of her Stanky sn*tch and ol’ Willy falls like a wounded soldier and shrivels up like a frightened worm. Game over.

The next morning she says that didn’t end the way I’ve always anticipated it would.., what happened to you last night. ( turns out she had always dreamed someday we would hook up even for one night)

I felt terrible and had to lie and say I was way too drunk and feeling guilty that I was taking advantage of her… rather than your pussy stinks like a goat girl !

No, not as I recall; I try to forget that event as much as possible. This was back in the early 80's when almost nobody, including dancers, shaved. She was very clean; it's just that her pussy was stinky, and she lay there like a dead fish.

If you're eating, don't read further.
I was eating a girls pussy, she was hairy. Her ass was also hairy. Then I saw lumps of shit sticking onto some of here ass hairs. End of story/sex.

Always sniff before eating:D

I was on a forced blind date with a buddy. His gf cousin was in town and he needed to entertain her so he pretty much bribed me into going out with them.

This girl was super boring and plain, think Rachel Dratch. We went to dinner and then out for drinks. My buddy and his girl were all over each other. I started feeding my “date” shots. Clearly she was just going along to be friendly.

At this point I decide I’m going to push the envelope and ask her if she’d like to go outside and fuck. Thought she’d get pissed and leave, to my surprise she says ok. So out we go to my buddy’s truck. She tries kissing me then starts giving me head. So far ok, then I tell her to take off her panties, and does and gets on all fours in the back seat, I slip in her hear her moan so I pick up the pace. Then she starts to spasm on her way to vomiting all over my buddy’s van. Way too many Southern comfort shots for her.

Not a good outcome.

The worst -
 

The dead fish thing...

Back when I was in my teens, I saw a sexy brunette at the local swimming pool. She was about 5' 7" and great looking in her dark blue bikini. Nice boobs, great ass, sexy smile, the whole package.

I struck up a conversation and before long we were dating. I move pretty quickly, so by the third date I had her nude and was doing my usual foreplay. It never fails, except for this time.

She didn't respond to anything that I was doing. I asked her if she wanted me to stop several times. She said "no" so I kept going.

Finally, after I thought that my tounge was going to fall off, I decided to just fuck her. Ted Bundy would have loved this chick. She just played dead...I mean like dead!

Something told me to wear a condom with her; I'm very glad that I did. After that night, I just didn't contact her anymore.

About a week later, I heard that one of my friends was fucking her. I was completely fine with that.

About six months later, I heard that she had herpes. About a year later, I heard that anyone could fuck her, if they gave her free drugs.

I will never forget the dead fish thing. Lol

That was the only time that has ever happened to me.

One of a few
 

Unfortunately I have had more than one but this one still gives me chills to this day. Wasn’t so much the sex but the anxiety afterwards.
Won’t mention age but I was working at a fast food restaurant and my manager was a slightly older bleached blonde married woman.
One night we were working the clean up shift and she surprised me with some beer she had stashed in the cooler. After a couple of hours of cleaning and drinking she started making advances and we ended up in her car in a nearby parking lot.
As things progressed and she was riding me she kept warning me not to cum inside her. As I felt myself getting close to the moment I warned her but she was too into the moment and kissed me deeply as I couldn’t hold back and unloaded into her.
When she finally realized what had happened she freaked out because she wasn’t on birth control.
Never knew how her and her husband dealt with it but for the next month it was Hell and she blamed me to an extent.
Fortunately she didn’t come up pregnant and I moved on shortly after.