Thought Catalog

32 Men Describe The Worst Sex They’ve Ever Had

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Illustration by Daniella Urdinlaiz
Found on AskReddit.

1. Right as she came, she says to me, ‘I’m really not enjoying having sex with you anymore.

“Ex-girlfriend (not ex at the time) was over, at we started going at it. As young, horny teenagers do. Anyways, she was sitting on my face, and right as she came, she says to me, ‘I’m really not enjoying having sex with you anymore.

Ouch. To both my self-confidence and my chance of getting off that night.”

slacktherin


2. To describe it as a hairy butthole would be an understatement. It’s like she used Rogaine to wash her butt or something.

“Took a girl home from the club. Everything was going great, we’re slobbering all over each other and the clothes begin to come off. I get up to walk over to my table and get a rubber. As I turn around she’s already getting on all fours. The moment she begins to arch her back those butt cheeks open up to reveal an Amazonian forest of bush. Now I’m perfectly fine with a little bush, but this girl had thick coarse hair running across her taint all the way to the coccyx. To describe this picture as a hairy butthole would be an understatement. It’s like she used Rogaine to wash her butt or something. I was immediately turned off and made the excuse that I was out of condoms.”

no_pip


3. She talked me into taking the condom off, then as we finished she casually said, ‘oh yeah, you should probably get tested.’

“Probably the girl in college that talked me into taking the condom off, then as we finished casually says, ‘oh yeah, you should probably get tested.’

Turns out she had just found out her boyfriend was cheating on her and I was apparently how she’d get back at him.”

petethepianist


4. A girl told me she had cancer halfway through and then wanted me to finish.

“A girl told me she had cancer halfway through and then wanted me to finish. That was bad.”

FixBayonetsLads


5. I had a great view of her pimply butt and a big ol’ hanging hemorrhoid staring at me.

“Was having a hard time staying hard, so I turned this girl around so I could go at it from behind. Now I had a great view of her pimply butt and a big ol’ hanging hemorrhoid staring at me. Definitely couldn’t keep it up with that thing watching me.”

japdot


6. When I fingered her, about a tablespoon’s worth of cottage cheesy discharge came out of her.

“Not full-on sex, but when I was 19 my girlfriend at the time didn’t tell me she had a serious yeast infection. When I fingered her, about a tablespoon’s worth of cottage cheesy discharge came out of her. I almost threw up. I’ve also gotten gonorrhea and chlamydia, but the sex itself was fine in those cases.”

Anonymous


7. I just stuck my tongue in the hole and she was like, ‘that’s not how you do it.’

“When I lost my virginity. I was so nervous my dick went soft like 30 seconds in, and I tried to hide it by going down on her. I unfortunately was not aware of how oral sex worked yet either, so I just stuck my tongue in the hole and she was like, ‘that’s not how you do it.’…

Good times.”

NecroCorey


8. She lets out the gnarliest, wettest fart I’ve ever heard, and blows shit and cum all over my hands, legs, and worst of all, my clean comforter.

“I’m living in Biloxi, Mississippi in the Air Force in the early 2000’s.

My girlfriend at the time, super cute, athletic, red-haired Irish girl with a great ass from years of playing soccer. This girl loved anal, first person I ever met that would ask for it, and be totally sober. We’re fucking on my bed doggystyle, she reaches between her legs, pulls my dick out of her pussy, and slams into me, balls deep into her ass. All is going well, after a couple minutes I can’t take it anymore and blow everything into her butt. She turns around and says she has to fart and doesn’t know what to do. I can see the look on her face, she’s panicking and all I can think of, is that I just washed my comforter. I cup my hands behind her butt as she lets out the gnarliest, wettest fart I’ve ever heard, and blows shit and cum all over my hands, legs, and worst of all, my clean comforter. I loved that comforter. :(“

House_Junkie


9. She chose Spongebob over me.

“Went to her place she put Spongebob on in the back ground, and wanted me to do her on the couch I couldn’t stay hard because of Spongebob’s laugh and when I asked to turn it off she said ‘It stays on or you leave.’ I left. No, I was not feeling her Mr. Krabs.”

Carameldelighting


10. Booze, Taco Bell, pubes like razor wire, daddy issues, backseat of a Ford Tempo in the middle of a cornfield at 2AM.

“Booze, Taco Bell, pubes like razor wire, daddy issues, backseat of a Ford Tempo in the middle of a cornfield at 2AM. My all-time low.”

kylew1985


11. She started sobbing and went into a gut-wrenching twenty-minute tale about how her stepfather would tie her up and molest her.

“During my first one-night stand, I made a throwaway joke about handcuffs. This, naturally, led to her breaking into convulsing sobs and going into a gut-wrenching twenty-minute tale about how her stepfather would tie her up and molest her.

Ended up reading her favorite children’s books to her until she peacefully fell asleep. I had a Red Bull earlier (was young, dumb and nervous and didn’t want to get ‘too tired’) so I then just played Angry Birds next to her until 4 a.m.

And that’s the story of my first one-night stand.”

YourDailyDevil


12. Preacher’s daughter kept telling me ‘Hurt me, pagan boy’ over and over again.

“Preacher’s daughter kept telling me ‘Hurt me, pagan boy’ over and over again while she laid there and refused to do anything.”

DecimateTheDeceiver


13. She farts directly in my eye.

“There was a girl I’d see occasionally when we were both single. Hot. Blonde. Runner physique. She was amazing. We’d have a fling, go our separate ways, date a person, sleep around, and always find each other again, and show off our newly discovered sexual interests.

One such startling discovery (for her) was doggy style. Something she had always opposed. We’re in the middle of getting down to it when she up off me, pulls down her tiny purple booty shorts, and faces away from me on all fours.

It’s immaculate. Every part of her. I’m eager, too eager. So I decided to take my time…get up behind her, breathe in her ear, kiss my way down each and every vertebrae, down to that perfectly chiseled ass…And as I kiss my way down further…she farts directly in my eye.

She cries, I try and tell her it’s OK. She scurries away faster, still on all fours, still farting, and leaves. Never saw her again.

Got a horrible case of pinkeye, missed two days of work, and still haven’t heard from her.

So that was kind of bad.”

TheGentlemenBeast


14. About 45 minutes in, she dismounts and goes to the bathroom to take a dump.

“Was having marathon sex with an ex. About 45 minutes in, she dismounts without a word, walks out of the room, goes in to the bathroom right next to her room, and takes a dump. Thin walls. Hard to come back from that.”

Skel_Estus


15. Went to finger the girl and found a condom inside her vagina.

“Went to finger the girl and found a condom inside her vagina. I had been with her all day. No idea where it came from…”

TheTangeMan


16. My safe word was ‘triceratops.’

“Tried being tied up and gagged for my girlfriend. She gives me a safe word, ‘triceratops.’ We started off with some whipping and then some hitting and then I just had to say the safe word. The problem is that I am Russian, and even though I speak perfect English, my dinosaur’s stage was in Russia and triceratops wasn’t a word I knew. So she thinks that I am saying it wrong on purpose as part of the roleplay, so that she would hit me harder, and is beating the shit out of me. I should probably add that she was a pro kickboxer. So, fun wasn’t had. But I told my coworkers about it and whenever triceratops is brought up in any context, one of them bursts out laughing.”

alumunum


17. Here I am, still inside an unconscious girl who just admitted she loved me after 3 dates.

“Girl I dated when I first moved to NYC. We dated a while and then things got hot and heavy. We started having sex. About midway through she orgasms and starts crying. Being concerned, I stopped and asked if she was OK. She goes onto a sob story about how she’s only been with 1 guy and that our sex was so intense that she just loves me so much. Then she passes out from crying so much. So here I am, still inside an unconscious girl who just admitted she loved me after 3 dates (stone cold sober mind you at least I hope she was). Killed my sex drive right then and there. I woke her up and drove her home. I didn’t talk to her afterwards.”

Dfiggsmeister


18. She shit on my dick.

“She shit on my dick. I had to squeeze the head to get the shit out of my urethra.”

HorseSteroids


19. She took off her pants and the smell smacked me like a tuna to the face.

“A woman I was into went on a few dates. After one of them we headed back to her place to get it on. She took off her pants and the smell smacked me like a tuna to the face.

I tried to play through it. It was so bad that 2 minutes in I faked a sprained ankle when switching positions by stepping on a throw pillow. I even purposely fell naked into a pile of LEGOs to sell it.

I sold it so well that Shawn Michaels would have been proud. She bandaged my ankle up and assisted my out to my car. Found out later she got rid of all her throw pillows from her room.

We have some friends in common, and every time we run into each other she turns red and apologizes profusely.”

DevlinInMrsJonez


20. 69’ed with a girl and her ass hair poked me in the eye.

“69’ed with a girl and her ass hair poked me in the eye. Haven’t 69’ed since.”

TrowAway4Daze


21. Got drunk, stabbed wife in butt with dick, she cried and bled.

“Wife and I were on vacation at a nice, all-inclusive resort in Jamaica. It was a couples-only resort so it was very peaceful and we were very able to keep a light, sexy mood throughout our stay. We were younger, hadn’t had kids yet, so naturally there was a decent amount of sex happening. On this particular night, my wife had dressed in a very sexy outfit and we ended up getting pretty smashed. After dinner and lots of drinks we hurriedly made our way back to our room to begin our sexcapades.

We were going at it pretty good. We were also very drunk. I was thrusting very hard, slipped out, and stabbed her rather forcefully in her poop chute.

I felt like I broke my dick. She screamed rather loudly and started crying. I was in pain and she ran to the bathroom. When I made it into the bathroom I noticed there was a lot of blood. She was crying, sitting on the toilet, with a bloody butthole. Needless to say, we didn’t finish.

Tldr: got drunk, stabbed wife in butt with dick, she cried and bled.”

MyStinkyDog


22. The first ten minutes she was like a dolphin sunbathing.

“I have one that made me cringe and hate doggy style for months.

I had this super religious coworker that was engaged for years and then her boyfriend dumped her. She’d had sex only once or twice before because she said she wanted to wait until marriage with the guy she was with (poor bastard, no wonder he dumped her).

Anyway a couple of days after they broke up, she literally came up to me and said ‘honestly I’ve been thinking about us doing it…so it’s up to you…’—she was wasted as fuck that night but she wasn’t drunk beyond that point where you think, this is just wrong.

So yeah she came back home with me and the sex was just fucking awful. 1) first ten minutes she was like a dolphin sunbathing. Just lying still making the most strange noises. Like if someone wanted whistle through a glory hole. It was weird. 2) Constant intense eye contact. Eyes wide open but motionless, constantly looking at me. If I would look away she would say ‘look at me, look at me!!’ So I looked. 3) this was by far the worst part. She completely ruined doggy style for me, for some fucking reason her asshole was so fucking hairy. It was like a one-eyed gremlin (that’s what I called her at work for months after that night) staring right into my soul. I just couldn’t fathom that someone that pretty and neat would just have such a fucking disgusting looking brown eye bush.

Immediately lost my erection. I went to the bathroom, got back and she was just lying in my bed. I sat down and she said ‘so what’s your favorite color?’

At this point I was just devastated. I was silent for like 2 minutes and looked at her and said ‘this was a mistake.’

Took a shot of tequila and went to bed.

Honestly gruesome stuff.”

L4MAT


23. I screamed, ‘did you just piss on my dick?,’ waking up my entire family.

“Was 15 and snuck my girlfriend over, sex was going good until we both found out that she was a squirter and I screamed, ‘did you just piss on my dick?’ Waking up my entire family who still make jokes about it now 12 years later.”

PhilyMick67


24. I basically fucked the queen of dead fish.

“I basically fucked the queen of dead fish. She was hot but so intimately inept and lifeless that I just couldn’t finish. I faked it and went home to jack off. It was the sexual equivalent of having a shit meal at a posh restaurant and stopping at McDonald’s on the way home.”

inappropriate_jerk


25. I felt like a starfish rapist.

“Girl did not move an inch, I felt like a starfish rapist.”

MustardReddit


26. She proceeded to grab my dick and jerk it into a circle like she was stirring a goddamn cauldron or something.

“Sophomore year of high school, I had this girl in my bed and we were watching a movie. We were both virgins at the time but I had some previous sexual experiences with other girls, but sadly she had not had any experience at all. But boy did she try…she proceeded to grab my dick and jerk it into a circle like she was stirring a goddamn cauldron or something. My friends still make fun of the ‘circle job’ to this day.”

TommyboyD


27. She totally reeked of crab.

“Went on vacation in Maryland about 4 years ago. My wife is one of these people that is rail thin but eats like a 300lb man. Since we were in Maryland she decided to go to a buffet that serves crab and absolutely stuff herself. Later than night she was in the mood and climbs on top of me when suddenly it him me, she totally reeked of crab. I hate seafood. I spent the next 15 minutes trying not to throw up on her.”

MyAnimalsBite


28. Girl moaned like a cow.

“Girl moaned like a cow. Seriously, halfway through just this loud bellowing OOOOOoooooOOoOOOOO. I…couldn’t keep at it.”

ilazul


29. She told me she was at the risk of having a stroke while I was fucking her.

“Girl I was seeing didn’t seem very into it to the degree that I asked what was wrong.

She said that her doctor had told her not to have sex until they’d run more tests. She was having some weird symptoms and they were afraid that she was at risk of having a stroke.

She said this while I was literally inside her.”

kangareagle


30. There was a lot of screaming and blood.

“I had a young lady chomp down on my pecker. I thought for sure that I was going to die. There was a lot of screaming and blood. Then she just casually asked if I was done.”

madhader11b


31. I simultaneously came as she vomited ramen noodles.

“I simultaneously came as she vomited ramen noodles. My dick was still in her mouth and she ruined my sheets. We dated for two years after that.”

MTSHITZIPPER


32. A pungent vagina smell easily triggers vomiting.

“I went down on a girl while being so drunk everything was spinning. Turns out a pungent vagina smell easily triggers vomiting. It got everywhere.”

bushdid119 TC mark


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