23 Men Reveal The Absolute WORST Sexual Experience Of Their Lives

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

Met girl at rave. Go to graveyard. Get 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 reeked like a fish’s asshole.

Was back in high school. Things were get hot and heavy until I tried taking her gasps 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 sexuality 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 gross me out but…My balls got tickled by her fart.

4. I lay there….unspent and sad.

Does masturbation count? Im 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 scratch it out.

I proceeded to slip in and out of consciousness for a good ten minutes, scratching it until it is hard, falling half asleep for a minute, waking up again, scratching it again. After those ten minutes, I merely 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 period. Scarcely 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 breach, we were in the doggy posture. I started thumbing her and she started to orgasm. She shit right in my hand. 🙁

7. I hurled up on her snatch.

I went down on a girl and it reeked precisely like an Arby’s cheddar melt. I threw up on her snatch, and that wasn’t a bargain 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 hollering this is a bad dreaming. This has got to be a bad fucking dreaming. Meanwhile in grind township, the odor of Arby’s and half-digested oatmeal smeared my face as I finally called in horror and ran out.

You try getting that out of your beard.

8. She insisted on watching while blowing me.

Ended up losing my virginity to my first girlfriend while watching I asked her if we could perhaps 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 limb was getting tired. I farted mid-way through and the smell was a distraction.

I start to cum and it immediately get soft and just like oozed 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 merely 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 person money.

Then I got a sandwich and played Minecraft.

10. I found out in the most painful style 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 “shes trying 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 portion due to my screaming 🙁

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

I was once having sexuality with a girl I’d been dating for a few weeks. I supposed 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 ;D R 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 scratching between her ass cheeks and sheets the whole time.

First time I ever did it. I was thrusting hard and doing well, so I guessed. Then she kindly informs me I wasn’t in and was scratching 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, Im at a bar and I start working on a girl. Shes fairly 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 its been forever since she’s been laid.

Im merely 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 doesnt have a car so I dont know how she would get home, etc ., etc. Eventually she caves.

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

She opens the door; we go in and Im slapped across the face with the stench of weeks-old garbage and a heap of dishes festering in the sink. I have no notion 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 encompasses every conceivable surface, and is several feet thick in some places with heaps of laundry and random items littered across the floor.

At this point, a better human would have called it. Thanked her for the lovely evening and taken a very lonely but far more sanitary taxi ride back home. But its been a while for me and shes probably the hottest chick Ive ever landed. So instead her and I waded through the heaps of garbage to induce our way to her bedroom.

She results me to a windowless room that I can only describe as a closet. Its scarcely large enough for a single mattress, which is placed directly on the floor. We are surrounded on all sides by pilings of junk and clothes but Im alleviated 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 lightings in the room. She fumbles around and says Just a second! while she rummages through her handbag, takes out her cellphone, activates the flashlight app, and MacGyver’s the worlds saddest desk lamp by propping it up on a heap of dirty clothes.

We get down to business. At this phase Im so thoroughly disgusted with myself that Im be very difficult getting ready for action. Fortunately( or perhaps regrettably ), she sucks dick like a champ and we get things underway. I put on a condom and were off to the races. At this point all I want to do is blow my load and build my escape from this smelly dungeon.

Then she stops me: Wait a second I believe the condom transgressed. My heart immediately confiscates 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 thumb into her pussy, fishes out a broken condom, and flings it at the wall. As shes rummaging through her trash heap looking for another condom I look down and I notice something. Im still wearing a condom And its wholly intact.

tl ;d r 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 daughter who was 18. I fulfilled her mom and they were even talking about how they were planning her 19 th 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 auto. She gets sick and pukings at one point, super drunk, but thankfully she managed to vomiting outside the car. We keep going at it, or trying to; I was drunk myself and drunk me and erections dont work so well, windows had fogged up and the car was rocking.

There’s a sharp knock at the window that I dismissed, 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 policeman tone telling us to exit the vehicle.

Two policemen 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 Im 21 sir, but I haven’t furnished any alcohol to anyone but myself. Cop smirks but looks at my GF and asks her her age.

She seems 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 supposed must have been a misheard statement. The moment the statement was confirmed was met by a What the fucking fuck !?! scream of incredulity and projectile vomiting 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 gratified her mommy and how the fuck that was even possible. Apparently my reaction was so genuine that the cops believed it. They even had the girl bellow her mom and her mom confirmed that they had lied to me. All I received that night was being pulled aside by cops and a lecture about checking daughters IDs.

15. The smelllike wet garbage in the hot sunhit me.

Back when I was in statute 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 statute school hotlate 20 s( and just starting to show it ), slightly pudgy, finally trying harder to dress professionally than to garment sexy, generally attractive, but didn’t really stand out in a mob. Her biggest assetliterallywas her awesome rack. To quote, they hung enormous, the route 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 was a great deal.( The stress during the course of its initial year in statute 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 phase, so when I considered her walk through the door, I waved her over and she joined our group of about ten or so.

At some pointprompted in part, I’m sure, by large quantities of boozewe of course started talking about sex, and because one of the guys with us was gay, the issue of anal sex came up. After a bit, M are recognizing that she had never tried anal. I was drunk and impression 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 entrance 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 remain, so I offered to buy her next drinking if she’d stick around.

When I came back with her drinksomething with tequila, I believeshe turned to me and said, I shouldn’t be feeing 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, objective up naked and horizontal in her bed.

Emboldened by earlier dialogue, M’s apparent enthusiasm, and a large dosage of alcohol, I eventually suggested that we try anal, and M agreed. After some shuffling, we aimed up with her on top so that she could control the depth and velocity, and for a few minutes, I was blithely 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 ache and dread. Presuming 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 tip-off 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 implored 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 purposes of the act, and the sheer ridiculousness of it all mean we didn’t construct much progress. In a moment of inebriated genius, I hoisted her up by the hips and indicated she walking on her hands.

It turns out that wheelbarrowing a weeping drunk daughter across her apartment with your dick stuck in her ass isn’t especially 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 detonation 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 smelllike wet garbage in the hot sunhit me. I was painted from waist down with her special brand of brownie batter.

I was in shock. I only stood there, dumbfounded, staring at this poor daughter, suffering the world’s worst case of mudbutt, weeping 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 voice. 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, person snapping gum through their teeth, and the glug of a water cooler. That audio 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 remote drone, nearly outside my notification, 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 entail 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 find me, but I didn’t care. I operated the 100 yards to my apartment door, past everyone, and I hurled myself in the rain, and I cried.

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

Was having sex with my girlfriend at the time shes this cute little thing but really strong( she actually joined the Army later) anyway shes 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 set her hands in my hair, small problem her one limb 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 sexuality) and her body. She decides to quickly pull her hand out just as I was thrusting. She knocks out my subsistence and I start to fall so I lift my other hand and throw it to center the balance. Her find my fall turns to her side so we dont whack skulls. Now this daughter weighs 110 soaking wet, I’m 250 lbs. My center balancing posture threw my hand down at Mach 1 with 250 lbs behind it immediately 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 ;d r Couldn’t get it up and repeatedly embarrassed myself night after night for two weeks.

So I met this daughter overseas. She was also American and was working in the same region 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 aimed up going home for a few months.

While I was home, we kept talking of Facebook and genuinely hit it off. Flirting became sexuality 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 find 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 plenty. Too much. So much that my nerves overruled my basic biological functions and I ran soft as a bar cloth as soon as she was above me about to set it in. Try as we might, there was no get me stiff again. I’d never had difficulty maintaining 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 period with a therapist back home, I decided that honesty with her and with myself was the best policy here and just has pointed out that I was nervous as shit and didn’t think I could be performing tonight. She concealed her letdown 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 even worse every day for like 2 week. 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 constructed me even more nervous, but she never did.

Finally, in a night of merely the right amount of tipsy, I pulled it off! Had drunk, short, sloppy sexuality, but I was mildly reassured that I at least was capable.
Over the next few days, I gradually get over my nerves enough to at the least maintain hard enough to penetrate. When I was ultimately batting 100 instead of zero, we basically opened the floodgates and fucked at the least daily for months. Sex get 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 thrustings in before the girl’s friend barges into the room and starts hollering bloody murder.

Coincidentally my first go at sex…. Party at a good friends’ home, 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 get in trouble earlier in the week with her mom 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 thrustings in before the girl’s friend barges into the room and starts screaming bloody assassination, for no reason beyond being a drunk high school girl encountering an awkward interaction, whole room hurry-ups 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 persuade her to do something else.

Her praying me to cum had opposite impact it should have. Normally wind jolts I cum, but not this day.

Finally take matters into my own hands( A , usually 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 spouse getting blow chores I somehow don’t want every night flashings 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 hour I was believe, Im 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 objective 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 believing Im gonna fucking die, I’m gonna die fucking person in doggy and pin her down with my body when I do.

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

21. And that, dames 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 dialogue her purposes for my company became clearer the more often her ass stimulated its way to grinding against my groin.

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

However my companion was decided. 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 stance I guided my cock to her awaiting opening, and did my damndest to enter her.

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

Propping my would-be lover onto her knees, I assumed my stance 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 persuade 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 define. 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, foreseeing 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 cloth, and managed to splutter the words I need a cigarette.

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

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

Was young and was having sexuality 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 get up, afterward in the house I felt a weird pressure on my dick, went to the bathroom and procured a long yellow dead piece of grass up my dickhole. Hurt the whole way out.

If youre 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, sexuality, etc. Upon its aiming, I was a total wreck. A pitiful mass of ridiculously maudlin sentiments. My friends maintained telling me I needed to rebound. Get under somebody to get over someone. You know the drill.

So a perfectly lovely daughter 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 sexuality from romantic impressions, 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 reasonably vanilla sexual partner, was not prepared to hear.

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

Me: Uh

Her: We can savour each other’s blood.

Me: can we just go to sleep, please?

She maintained stroking my face all night.

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

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