23 Men Reveal The Absolute WORST Sexual Experience Of Their Lives

Illustration by Daniella Urdinlaiz / lookcatalog
Illustration by Daniella Urdinlaiz / lookcatalog
Found on AskReddit.

1. Her false eye popped out and I felt it on my balls.

“Met girl at rave. Went to cemetery. Getting beej, she deep throated, her false eye I was unaware of came out.

Felt it on my balls.



2. There was a swamp-green streak in her panties that smelled like a fish’s asshole.

“Was back in high school. Things were getting hot and heavy until I tried taking her pants off. There was a swamp-green streak in her panties that smelled like a fish’s asshole. We didn’t even get to the sex part and I still consider it the worst sex I’ve ever had. It still haunts me to this day.”


3. My balls got tickled by her fart.

“With my now ex-wife. Standard sexy-time up to a point (kissing, boob play, a little oral), then I go to put it in. She farts. I felt it tickle my balls.

It tickled my balls, man. You can’t keep going after that. I’m a nurse and not much grosses me out but…My balls got tickled by her fart.”


4. I lay there….unspent and sad.

“Does masturbation count? I’m going to tell it anyways.

I was having a dry period of about a month. I woke up after a really vivid wet dream and tried to rub it out.

I proceeded to slip in and out of consciousness for a good ten minutes, rubbing it until it is hard, falling half asleep for a minute, waking up again, rubbing it again. After those ten minutes, I just gave up. I lay there….unspent and sad.”


5. I was gagging the entire time.

“Was quite drunk and in a miserable period in my life where I’d fuck just about anything. Hooked up with a neighbor’s friend. She had dreads. I was gagging the entire time. Barely managed to finish. Showered for what felt like an eternity after.”


6. She shit right in my hand.

“I pulled out to give myself a break, we were in the doggy position. I started fingering her and she started to orgasm. She shit right in my hand. :(”


7. I threw up on her snatch.

“I went down on a girl and it smelled exactly like an Arby’s cheddar melt. I threw up on her snatch, and that wasn’t a deal breaker for her. It just made her want it more. She knew I liked it a little rough, from previous conversations, and so she straight up launched herself, puke beef cootchie and all, right onto my face and starts grinding. I was so caught off be-fucking-wildered that I froze, internally screaming ‘this is a bad dream. This has got to be a bad fucking dream.’ Meanwhile in grind town, the aroma of Arby’s and half-digested oatmeal smeared my face as I finally screamed in horror and ran out.

You try getting that out of your beard.”


8. She insisted on watching What’s Eating Gilbert Grape? while blowing me.

“Ended up losing my virginity to my first girlfriend while watching What’s Eating Gilbert Grape? I asked her if we could maybe turn it off, at which point she removed my penis from her mouth and said, ’But it’s my favorite movie?’”


9. It was like my penis rolled a sticky tear.

“I had a pretty sad jerk off the other night.

I guess my heart wasn’t into it or something but the run up to the orgasm started fine but then it just became a chore. I kept thinking about other stuff. My arm was getting tired. I farted mid-way through and the smell was a distraction.

I start to cum and it immediately got soft and just like seeped out. No energy behind it at all. No happiness or excitement. It was like my penis rolled a sticky tear.

Then my dick was like a sad old drunk slumping into a puddle of his own sick. I just sat there all heavy with shame for a few seconds as this gif looping on my monitor that, with the haze of arousal fizzled, was just awkward and weird. All titties being mashed and slapped around like they owed someone money.

Then I got a sandwich and played Minecraft.”


10. I found out in the most painful way that I was in fact too big for her once her teeth shredded my dick and filled her mouth with blood.

“Was dating a girl a few years back and after a month of intense make out sessions and heavy petting we decided it was time to take things to the next level. It started off well enough when she pulled out my junk and exclaimed I was the biggest she’d seen, and she was proud of her ability to deep throat and was insistent she could take me on. So without any warm up at all she tries to shove my entire dry dick down her throat and I found out in the most painful way that I was in fact too big for her once her teeth shredded my dick and filled her mouth with blood. We didn’t get to the sex part due to my crying :(”


11. I accidentally told a girl I loved her and proceeded to have awkward coitus.

“I was once having sex with a girl I’d been dating for a few weeks. I thought she said ‘I love you’ so I was like ‘Oh I love you too’ but she actually just said something completely different. She stopped dead and questioned what I’d said, but I just said never mind and carried on. TL;DR I accidentally told a girl I loved her and proceeded to have awkward coitus.”


12. She kindly informs me I wasn’t in and was rubbing between her ass cheeks and sheets the whole time.

“First time I ever did it. I was thrusting hard and doing well, so I thought. Then she kindly informs me I wasn’t in and was rubbing between her ass cheeks and sheets the whole time. I almost came from that.”


13. I banged a hoarder in the closet of her smelly apartment. Afterwards she fished an old condom out of her pussy.

“So, I’m at a bar and I start working on a girl. She’s pretty hot. We dance, we drink, we talk. She makes it pretty clear she wants to go back to my place. At one point, she was even joking how it’s been forever since she’s been laid.

I’m only in town visiting a friend and crashing on his couch so I insist on going to her place. Initially she resists the idea but I elaborate on the couch thing, plus he lives super far away, he doesn’t have a car so I don’t know how she would get home, etc., etc. Eventually she caves.

She lives walking distance away in a pretty nice apartment building. We go up the elevator and when we get to her front door she warns me that she shares a 1 bedroom apartment with a roommate and that, ‘It’s a little bit messy.’

She opens the door; we go in and I’m slapped across the face with the stench of weeks-old garbage and a pile of dishes festering in the sink. I have no idea how someone could live with that smell emanating from their kitchen but perhaps even worse is the whole place looks like an episode of hoarders. Junk is everywhere. It covers every conceivable surface, and is several feet thick in some places with piles of laundry and random items littered across the floor.

At this point, a better man would have called it. Thanked her for the lovely evening and taken a very lonely but far more sanitary cab ride back home. But it’s been a while for me and she’s probably the hottest chick I’ve ever landed. So instead her and I waded through the piles of garbage to make our way to her ‘bedroom.’

She leads me to a windowless room that I can only describe as a closet. Its barely large enough for a single mattress, which is placed directly on the floor. We are surrounded on all sides by piles of junk and clothes but I’m relieved to be away from the chaos and stink that is her kitchen.

We go in and I close the door behind us and we are plunged into blackness. There are no lights in the room. She fumbles around and says ‘Just a second!’ while she rummages through her purse, takes out her cellphone, activates the flashlight app, and MacGyver’s the worlds saddest desk lamp by propping it up on a pile of dirty clothes.

We get down to business. At this point I’m so thoroughly disgusted with myself that I’m having trouble getting ready for action. Fortunately (or perhaps unfortunately), she sucks dick like a champ and we get things underway. I put on a condom and we’re off to the races. At this point all I want to do is blow my load and make my escape from this smelly dungeon.

Then she stops me: ‘Wait a second… I think the condom broke.’ My heart immediately seizes up and sinks to the pit of my stomach as I consider the possibility of being connected to this hot mess and her garbage dungeon for 18 years.

I withdraw and she sticks her finger into her pussy, fishes out a broken condom, and flings it at the wall. As she’s rummaging through her trash heap looking for another condom I look down and I notice something. I’m still wearing a condom… And its totally intact.

tl;dr I banged a hoarder in the closet of her smelly apartment. Afterwards she fished an old condom out of her pussy.”


14. I projectile-vomited from the realization I had been banging a 15-year-old for a month.

“This one is sad and I’m disgusted with myself for a reason that will become clear. I was 21 and had been dating this girl who was 18. I met her mother and they were even talking about how they were planning her 19th birthday party and how she couldn’t believe how fast her little girl was growing up and her mom even said her daughter scored big time landing a handsome 21-year-old man yadda yadda. It was weird and felt like I was missing an inside joke. Fast forward a month and lots of pretty good sex.

We had left party at a beach house to fuck in my car. She gets sick and vomits at one point, super drunk, but thankfully she managed to vomit outside the car. We keep going at it, or trying to; I was drunk myself and drunk me and erections don’t work so well, windows had fogged up and the car was rocking.

There’s a sharp knock at the window that I ignored, kept fucking. Then there’s another knock and its insistent. I get angry at this point and yell ‘leave me alone, we are fucking!’ I thought it was a friend looking for us. Nope. I was met by a blinding light being shown and an obvious cop tone telling us to exit the vehicle.

Two cops were outside and asked if we were at the party because they had a noise complaint. Yup. I’m freaking out because she’s clearly wasted and she was only 18. I was 21 so I just knew I would be hit with a charge for supplying alcohol to an underage person. The dreaded question comes up. ‘How old are you?’ I responded with ‘I’m 21 sir, but I haven’t supplied any alcohol to anyone but myself.’ Cop smirks but looks at my GF and asks her her age.

She looks around shyly, albeit drunkenly, and says ‘Fifteen.’ It took me a moment to clock it but the cops looking at me wide-eyed confirmed what I thought must have been a misheard statement. The moment the statement was confirmed was met by a ‘What the fucking fuck!?!’ scream of disbelief and projectile vomit from the realization I had been banging a 15-year-old for a month. She did not look like she was that young.

I immediately went on a rant about how I met her mom and how the fuck that was even possible. Apparently my reaction was so genuine that the cops believed it. They even had the girl call her mom and her mother confirmed that they had lied to me. All I received that night was being pulled aside by cops and a lecture about checking girls’ IDs.”


15. The smell—like wet garbage in the hot sun—hit me.

“Back when I was in law school, there was a girl, M. M was a wholesome gal from Wisconsin: blonde hair, blue eyes, a slight gap in her front teeth. A real girl-next-door type (in the traditional, non-porno sense). She grew up on a dairy farm.

M was what we called ‘law school hot’—late 20s (and just starting to show it), slightly pudgy, finally trying harder to dress professionally than to dress sexy, generally attractive, but didn’t really stand out in a crowd. Her biggest asset—literally—was her awesome rack. To quote Fight Club, they hung enormous, the way you’d think of God’s as big. Her daddy would have been lucky to have a milk cow endowed like her.

It was the end of our first semester, which for new 1Ls is a huge deal. (The stress during the initial year in law school is tremendous; if you’ve ever seen the movie Paper Chase, it’s 100% accurate.) The tradition at my law school was for everyone to saunter over to the bar a block away after their last exam and hang out. M and I had a friendly relationship up until that point, so when I saw her walk through the door, I waved her over and she joined our group of about ten or so.

At some point—prompted in part, I’m sure, by large quantities of booze—we of course started talking about sex, and because one of the guys with us was gay, the topic of anal sex came up. After a bit, M admitted that she had never tried anal. I was drunk and feeling saucy, so I said, ‘We should rectify that.’ ‘Rectum-ify,’ she giggled back, and at that moment, I decided to put all of my drunken intellect towards coming in her back door before the night was out.

After a few hours our group was dwindling, but some of us were determined to continue celebrating for a while longer and M was looking like she was ready to head out. She needed to eat, she said, and was running out of cash, too. We still had about 3/4 of a pizza left, and I was trying to convince her to stay, so I offered to buy her next drink if she’d stick around.

When I came back with her drink—something with tequila, I believe—she turned to me and said, ‘I shouldn’t be eating this, I’m lactose-intolerant. I hope you’re happy, because I’m doing this for you.’

After that round, more people headed out, and M couldn’t be persuaded to stay. But I wasn’t ready to give up, so I offered to walk her home, since our apartments were next to each other, and only a few blocks away. When we got to her place, she invited me in. We went through the standard fooling around routine, ending up naked and horizontal in her bed.

Emboldened by earlier conversation, M’s apparent enthusiasm, and a large dose of alcohol, I eventually suggested that we try anal, and M agreed. After some shuffling, we ended up with her on top so that she could control the depth and speed, and for a few minutes, I was happily watching M’s magnificent mammaries jiggle around while she gingerly bounced on my rod.

After a few minutes, her expression switched from drunken sex stupor to pain and fear. Assuming I had hurt her somehow, I began to push her off of me, but she told me to wait. Sudden pressure and heat on my tool tipped me off to her digestive distress, and I could feel something trickling down my balls. I started to get up again, but she said, ‘No, please. Stay inside. Just for a minute.’ I protested, but she was panicked, and begged me to help her to the bathroom before I pulled out.

We flailed around for a moment, and awkwardly switched to doggy style. We tried to shuffle to the bathroom, but drunkenness, the physical difficulty of the act, and the sheer ridiculousness of it all meant we didn’t make much progress. In a moment of inebriated genius, I hoisted her up by the hips and suggested she walk on her hands.

It turns out that wheelbarrowing a crying drunk girl across her apartment with your dick stuck in her ass isn’t particularly sexy, and a combination of internal pressure and my rapidly deflating member caused what is probably best referred to as an uncorking.

I watched in slow-mo horror as a fountain of diarrhea blasted out of her butthole, point-blank into my crotch. Spattering my torso. And my arms. And my face. And I dropped her. She hit the ground, hard, sobbing. The smell—like wet garbage in the hot sun—hit me. I was painted from waist down with her special brand of brownie batter.

I was in shock. I just stood there, dumbfounded, staring at this poor girl, suffering the world’s worst case of mudbutt, crying on the floor of her shitty apartment, shit oozing out of her ass, shit dripping off of me.

But as horrible as the sight and the smell were, the worst was the sound. That sound will haunt me for the rest of my life. No language on Earth can approximate the cacophony of her crapping everywhere. It was a combination of the most over-the-top whoopee cushion, someone snapping gum through their teeth, and the glug of a water cooler. That sound blared above all, the way classical music plays during the hero’s against-all-odds rush into death in war movies. The sobbing was a distant drone, almost outside my notice, but the burbling of her bowels was deafening, in perfect sonorous clarity.

I must have stood there for maybe 10 seconds, but it felt like an hour. In a daze I pulled my pants on, then ran out the door. I mean ran. I sprinted. I left my shirt, my shoes, my socks, my boxers. All of it was abandoned in my mad dash to get home. People on the street saw me, but I didn’t care. I ran the 100 yards to my apartment door, past everyone, and I threw myself in the shower, and I cried.”


16. She yelps like a pup and I spent the next 15 minutes cradling her as she whimpers, calling me an idiot.

“Was having sex with my girlfriend at the time she’s this cute little thing but really strong (she actually joined the Army later) anyway she’s on top, I grab her and pull her to me and flip her onto her back and now I’m on top. She fucking loves it. She decides she wants to put her hands in my hair, small problem her one arm is in between my hand holding me up (This was spontaneous hiking in the woods and on top of a picnic blanket sex and not soft bed sex) and her body. She decides to quickly pull her hand out just as I was thrusting. She knocks out my support and I start to fall so I lift my other hand and throw it to center the balance. Her seeing my fall turns to her side so we don’t whack skulls. Now this girl weighs 110 soaking wet, I’m 250lbs. My center balancing position threw my hand down at Mach 1 with 250lbs behind it directly onto her breast. She yelps like a pup and I spent the next 15 minutes cradling her as she whimpers, calling me an idiot.”


17. I lasted like 4 pumps max.

“tl;dr Couldn’t get it up and repeatedly embarrassed myself night after night for two weeks.

So I met this girl overseas. She was also American and was working in the same area I was. Short, great curves, cute face, overall way hot. Started talking to her on Facebook, and found out she was an awesome conversationalist and that we had a lot of personality traits in common. Unfortunately, things didn’t escalate quickly enough before I ended up going home for a few months.

While I was home, we kept talking of Facebook and really really hit it off. Flirting became sex references became overt ‘I want to have sex with you.’ This went on for like two months. We were Skyping and messaging all day long. We even discussed that we would be making out and banging as soon as I got back.

Finally got back and saw her again, and we immediately went back to my room and got down to it. 0-100mph in the space of about 10 mins, and we hadn’t even had a sip of alcohol.

I really liked this girl. A lot. Too much. So much that my nerves overruled my basic biological functions and I went soft as a bar rag as soon as she was above me about to put it in. Try as we might, there was no getting me stiff again. I’d never had trouble keeping it up (while sober) before and was highly surprised and disappointed with myself. I’d also never had this strong of an affection for someone before ever having sex with them.

Freshly inspired by some illuminating time with a therapist back home, I decided that honesty with her and with myself was the best policy here and just explained that I was nervous as shit and didn’t think I could be performing tonight. She hid her disappointment very well. We cuddled up and went to bed.

I woke up in the middle of the night, hard as a diamond, and decided to try again. Minimum amount of foreplay and I lasted like 4 pumps max. She actually thanked me for waking her up to try again!

I could get plenty hard enough when we tried from there on out, but as soon as the shuttle approached for reentry, all the heat shielding melted away, the structure collapsed, and the crew went down in burning flames. My nerves persisted with no sign of relenting with her over the next few days.

This saint blew me every day and I disappointed this woman who wanted my cock so bad every day for like two weeks. She stuck around enthusiastic and persistent (which blows my mind because she could have left and pulled any slab of hot meat she wanted) for two weeks. Expecting her to give up and leave made me even more nervous, but she never did.

Finally, in a night of just the right amount of tipsy, I pulled it off! Had drunk, short, sloppy sex, but I was mildly reassured that I at least was capable.
Over the next few days, I gradually got over my nerves enough to at least keep hard enough to penetrate. When I was finally batting 100 instead of zero, we basically opened the floodgates and fucked at least daily for months. Sex got better and better and she stuck around.

She moved in with me last summer and I can’t imagine a cooler girlfriend.”


18. We get 4, maybe 5 thrusts in before the girl’s friend barges into the room and starts screaming bloody murder.

“Coincidentally my first go at sex…. Party at a good friends’ house, talk to a girl all night and end up in one of my friend’s bedroom, my friends were siblings, this is important because my friend had gotten in trouble earlier in the week with her mother resulting in her door knob being removed so she couldn’t lock the door. Things are getting hot and heavy, clothes are off, dick is slid in, and we get 4, maybe 5 thrusts in before the girl’s friend barges into the room and starts screaming bloody murder, for no reason beyond being a drunk high school girl encountering an awkward interaction, whole room rushes in as the girl sits, petrified, on top of my softening dick.”


19. Girl blew me. Somehow she made it boring.

“Girl blew me.

Somehow she made it boring.

Also dry like desert.

Painful, could not convince her to do something else.

Her begging me to cum had opposite effect it should have. Normally wind blows I cum, but not this day.

Finally take matters into my own hands (A, normally wouldn’t want to, B, she stopped me every time before she developed lockjaw an hour in) finish myself in her mouth.

Collapse from exhaustion and sadness.

She tells me she loves me.

This was our first sexual encounter of any kind.

Bizzaro world of future with her as my wife getting blow jobs I somehow don’t want every night flashes before my eyes.

I bolt.

She proclaims as I fade out of sight, ‘that was the best I’ve ever given.’

Her roommates were in living room, though I didn’t see them, I’m sure they  shook their heads.



20. The whole time I was thinking, ‘I’m gonna fucking die.’

“She was drunk, I was drunker, it was like trying to stab someone with a piece of soft rope, so I had some…enhancement pills, not a great combo being drunk, horny and all worked up so I basically ended up at near heart attack levels of strain on my heart, I mean I did it and she seemed happy enough, but the whole time I was thinking ‘I’m gonna fucking die, I’m gonna die fucking someone in doggy and pin her down with my body when I do.’

Ironically I bet that made me last longer. Also when I woke up I was still erect.”


21. And that, ladies and gents, is how I began the year of 2016 by contracting syphilis.

“She was 5 foot nothing, perky breasts, and a shapely backside. Cute as a button.

She laid next to me on her single mattress in the dingy apartment room she was forced to rent in order to dance in the local strip joint of my home town. Both of us fairly hung over, though no less frisky for it.

As we lay there dozing in and out of sleep, and mumbling conversation her intentions for my company became clearer the more often her ass made its way to grinding against my groin.

Bedraggled state of affairs I was in, I tried to ignore her silent request for attention. Whether a result of anxiety at being in bed with a real live exotic dancer, the effects of my diet consisting solely of beer and cigarettes for 3 days solid, or a combination of both, junior was not up to the task.

However my companion was determined. Given her increased advances I refused to allow myself to miss the opportunity of bedding a stripper. Reaching a free hand into my boxers, I began to tug one out.

After a brief minute of awakening my member, I felt sufficiently hard enough to see through the task at hand. Rolling over into a spooning position I guided my cock to her awaiting opening, and did my damndest to enter her.

Unfortunately it became obvious that my wedding tackle wasn’t sufficiently warmed up, as I began pushing rope after acquainting myself with the first couple inches of her vulva.

Propping my would-be lover onto her knees, I assumed my position behind her and tried to go to work once more. I attended her vagina with one free hand while stimulating my rod with the other.

It only occurred to me after the first few strokes how long my willy had gone without attention. Before I could rethink my strategy-or convince junior to take any other form besides that of an over cooked pasta noodle-I felt an all too familiar sensation rushing through my vas.

I tried to clamp my trouser snake in a death grip as a last-ditch effort to stop the inevitable, but to no avail. Bat and balls pulsed in unison, erupting a fountain of jism far more enthusiastic than I would have expected given the setting. It was all over.

Kneeling there, unbelieving, I looked brokenly to the web of cum enveloping my hand and the considerable dollop on the sheets. My attempted consort still positioned patiently, eyes closed, anticipating more than the idle digit I had planted in her baby chute.

I did the best to compose myself, wiped the spunk off on a nearby scrap of fabric, and managed to splutter the words ‘I need a cigarette.’

And that, ladies and gents, is how I began the year of 2016 by contracting syphilis.”


22. I found a long yellow dead piece of grass up my dickhole.

“Was young and was having sex in the grass in the backyard, I felt a giant spider skittle across my chest and bucked the bitch off of me. Turned over and got up, later in the house I felt a weird pressure on my dick, went to the bathroom and found a long yellow dead piece of grass up my dickhole. Hurt the whole way out.

If you’re going to have sex outside kids, put down a blanket.”


23. The story of Vampire Girl.

“Oh boy. Let me tell you the story of Vampire Girl.

Many years ago, I had just gotten out of my first relationship. That first relationship included all the other firsts – kiss, grope, sex, etc. Upon its ending, I was a total wreck. A pitiful mass of ridiculously maudlin sentiments. My friends kept telling me I needed to rebound. Get under someone to get over someone. You know the drill.

So a perfectly lovely girl invites me out, then we head to her place. I was not into it. I was and remain pretty much unable to differentiate the act of sex from romantic feelings, and I was still in love with my ex. So things weren’t really working down there.

This lovely girl takes it in stride, and decides that some kink will help turn the cooked noodle back into hard, raw spaghetti. Cue something that I, the veteran of one fairly vanilla sexual partner, was not prepared to hear.

Her: ‘Do you want me to get out my whip?’

Me: ‘Uh…’

Her: ‘We can taste each other’s blood.’

Me: ‘…can we just go to sleep, please?’

She kept stroking my face all night.

Listen, S, I don’t know if you’re reading this, but current me would have been willing to work a bit with the whip. Still no blood play. Sorry for being awkward as all hell about it back then.”

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