30 Stories Of The Worst Sexual Encounters People Have Actually Had.

People meet up for one night stands all the time, and there's a select few that end up being memorable...but for the wrong reasons.

Below are stories of the worst sexual encounters people have ever had to deal with. Check them out!

30. Wouldn't do it again.

I met a guy that had never been with a man before. He was super enthusiastic and keen to try it out. However, enthusiasm, in this chase, meant it was like getting a blowjob from a chainsaw. It didn't help that it was dark. It's hard to complain when you're on a back country road in a six foot four man's car.


29. Yikes...

The one time my ex lasted longer than ten minutes. He was so proud of himself that he lasted for thirty minutes and calling himself a sex god that I didn't get a chance to even tell him that I didn't finish once.


28. A 90 degree penis.

I was with a woman who hadn't had sex in 3 years and only used a curved dildo and she tried to have sex like that. My dick is not a boomerang.


27. Improvising!

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... (Continued)

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

Good times.


26. Stiff as a board.

He had a huge penis. He did not move at all or even make noise. If i wanted to do myself with a 9 inch dildo I could have stayed at home. He got off, I did not.


25. Wise advice.

Definitely losing my virginity with breakup sex.

Don't lose your virginity with breakup sex.


24. That is just cold.

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.


23. A roller coaster of a story.

I picked a girl up at a pub after she told me I looked gay. I told her I'm not and I'd... (Continued)

I'd prove it to her. She mentions a couple times that I look like the American Idol singer Scotty McCreary. I had no idea who that was and didn't care. Her place wasn't far from the pub so we set off walking. She kept stopping me mid-stride to attack my face with hers. It was sloppy and not at all attractive.

When we get to her place she tells me to put on some music while she goes to freshen up. I open up her iTunes and call out to her asking if she has any RHCP. She shrieks and says they're her favourite band. I find them and she only has 5 songs by them, 3 of which are Scar Tissue. I create a playlist and put it on repeat. She comes in and we get right to it.

I don't have a condom with me so she insists that I do her in the ass. I oblige and after a few minutes, she reaches under her bed and pulls out a cowboy hat. She puts it on me, and then says: "Sing to me, Scotty." I didn't know what to do, so I just kept doing her. Kept the hat on, but didn't sing. Finished up, went to the toilet and cleaned my penis. Walked back to her bedroom to hear Scar Tissue playing again for the millionth time and gathered my things and left. Never saw her again.


22. Rough details.

Booze, taco bell, pubes like razor wire, backseat of a ford tempo in the middle of a cornfield at 2AM. My all time low.


21. Half a lifetime ruined.

My good friend, who I have been in love with for half of my life or so. The stars finally aligned - we were both single, both feeling it, and after a late night out, it was clear it was on.

We head to his room, and he turns into a crappy porn star. "Oh you like that you, don't you? Take it yeah. Yeah." and smashing like he was trying to bounce me off the bed. I was horrified. Like, dude, I know you. Your mother and I send you... (Continued)

I send you selfies when I visit her shop. I've been to your grandma's. That is how people talk in porn, not in real life. My crush was over before he was.


20. Bittersweet.

I took a guy home when we were both completely plastered.

He was on the smaller side but that didn't bother me... however when we came to actually trying to have sex it just wouldn't go in or stay in. We tried every position but just had no luck at all. I kept getting the giggles because it was just so absurd.

I then decided to give him head instead and when he finally came his sperm was so bitter that I audibly gagged and retched.


19. "I'm great, right?"

He was like flopping around on me. I was like wtf is happening?' And then he kept repeating 'I'm really good when I'm on top aren't I?" Not going to lie I just laid there thinking hurry up and get done. I'm usually a mover but I just didn't know what to do. Just patted him on the back.

Walked out after and never spoke to him again.


18. A not-cool plot twist.

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... (Continued)

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


17. An unfortunate story.

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 mid-way 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 one 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 three dates. Killed my sex drive right then and there. I woke her up and drove her home. I didn't talk to her afterwards.


16. A mystery to all...

In college, I briefly dated an exchange student. She was really cute and affectionate. She always had these giant emotes of excitement about regular things. Hanging on my arm as I'd show her stuff around town. She'd draw hearts on my arms when she got bored of studying. Often she packed me snacks or neat bento lunch. She was really sweet.

In the sack she just laid there and squeaked. In doggy style, she'd just plop and squeaked into the mattress. When I asked her what she liked and she'd blush and not even look at me. I'm already conducting a full exploratory mission into her and she wouldn't communicate what she did or did not like. It was awful.


15. A total mess.

Threesome with 2 women.

I was 20, 6ft and about 145lbs. They were mid 20s, similar height, and double my weight.

I was so drunk I couldn't get it up, so I tried... (Continued)

I tried fingerblasting them both at the same time (pretty sure I cut one with a fingernail), gave up and passed out on the floor.


14. Not all it cracked up to be.

Dude had literally no rhythm.

He was hot. Just my one of my types. Tall, handsome, olive skin, that nice big Italian type.

He'd like... vibrate. It was so bad. Even when I tried to take control and get on top he'd try to regain control and still do this weird erratic jerking around movement that was so off putting.


13. Not all it cracked up to be...

A girl who was a friend of a friend's girlfriend. She was hands down the most attractive sexual partner I've had.

The sex was the worst. She did very loud, very fake, very exaggerated moaning that didn't even sync up with my thrusting. She also said she loved giving head and turned out to be really bad at it (teeth). Also, she thought her being on top meant just sitting on top of me with my dick in her and then me doing all the work.


12. Prescribed sex is no good.

Being prescribed sex by the reproductive endocrinologist after an IUI procedure. I was sore and uncomfortable from fertility drugs and my husband was feeling pressured into it. No one has fun when it's required and you're failing to get pregnant each time.


11. Right in the crazy.

During my first one night stand I went home with a girl who was passing through town, she was cute. She started full on making out with me at this bar like no one else was there. I was 21 at the time and thought it was awesome(I now realize it was not). We ended up going back to her hotel and hooking up everywhere in the room. Should have been hot, but she made no noise. It was like fucking a doll. Then when we were on the bed shit bit me so hard it broke the skin and scratched my back really bad. I stupidly stayed there that night and all night all I could think was maybe I just sucked that much in the sack that she had to bite and scratch me. She then extended her stay in town and creeped on me for three days. Worst idea ever.


10. Almost fascinating.

About 15 years or so ago.. this chick from the internet.. flew up to meet up with me from Maryland. I can't imagine that she could even drink from a straw because her blowjob technique lacked any sort of visible resemblance to a living person. I literally went soft.


9. Not the wall!

Super hot guy was a casual friend, we tried to hook up one might when we were both drunk. Turns out we are both on the submissive side of things, but that's not a deal breaker, so we kept trying. Then he went to flip us over all forcefully, and smacked me face first into the bookshelf above the bed. We still kept trying.

Then, he pulled out and came on the wall. Was my friend's room, so I feel bad about that part.


8. The fart that ruined it all.

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 and faces away from me on all fours.

I'm eager, too eager. So I decided to take my time..get up behind her, breath 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 its okay. 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 havent heard from her.

So that was kind of bad.


7. A smorgasbord of bad experiences.

Slept with a guy and while we were doing it I angled my head up to try and kiss him. He came to an absolute dead stop and asked "What are you doing?" in the most horrified voice. Mood effectively flatlined. "Uh....kiss you?" He looked at me in the most condescending way I could ever hope to be seen and said "That's for before sex." Uh, okay. Then he complained that I had killed his boner, so I got up and got dressed and left.

Runner up: the guy who licked my face and asked "Isn't this sexy? Isn't this so hot? Isn't this just so amazing?" the entire time. Sexy things are way less sexy the more you ask someone if they're sexy.

Also runner up: the guy who thought that if he lay on top of me while in me and shook himself really fast, he'd be a human vibrator. Spoiler: He was not.


6. Not worth.

I had a bad break up and attempted the old "Get over that someone by getting under someone else" method of coping.

The very next day I set up a booty call with a girl at work that I knew was attracted to me. She was super hot but was kind of a jerk and very obnoxious. She was a terrible lay and I faked an orgasm just to get it over with. My lack of attraction to her - despite her good looks, was a big reason.


5. That sounds...terrifying.

Well, had an ex who basically didn't move, didn't make any noise, and didn't make any facial expressions during sex. It was extremely off-putting.


4. A truly heartwarming story.

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 her favorite children's books 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.


3. Roommate to the rescue!

Went out to the bar and ran into a group of friends, one guy they were hanging out with I thought was sort of cute but didn't think much else. One thing led to another and I'm in my bed and naked with this guy next to me. I think he was trying to sound seductive and sexy then says, "Would you like another drink?" as a way of asking if I want to go for Round 2.

I decline by claiming I'm sore and am trying to hint that I want him out of my house so I can get ready for work. I get up to get dressed, and my gay roommate walks into my bedroom still fucked up from the night before. He crawls into my bed and starts spooning the guy while he is still naked. He left rather quickly after that, haven't seen or spoken to him since.


2. Spongebob or go home!

Went to her place she put Spongebob on in the background, 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 stay on or you leave". So I left.


1. Awful foreplay.

We were both virgins. The sex itself wasn't great, but the worst part was the foreplay. I hand my hand down her panties and was rubbing her clit. I guess she assumed since that felt good for her, it would feel good for me for her to rub my piss hole with her thumb. It. Did. Not.



"It wasn't me!"

There's not much you can do when the righteous fist of the law comes down on you. Call it a mix-up, or call it a mistake, if someone's pegged you at the scene of a crime there's not much you can do but trust the justice system to prove you innocent. However, that's a gamble, and just because you've been given a "not guilty" doesn't mean the effects won't follow you for the rest of your life.

Reddit user, u/danbrownskin, wanted to hear about the times when it wasn't you, seriously, it was someone else, when they asked:

Redditors who were once considered suspect of a crime they did not commit, what's it like being held under suspicion and how did it affect your life?

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