1. Three words: three-inch dick.
“Three words: three-inch dick. He was grossly overweight and refused to take off his pants. It didn’t even remotely make it inside me.”
2. He fingered me so hard that I had to go to the hospital.
“A dude I hooked up with fingered me so hard (and not in a good, fun way) that he shifted my IUD and I had to go to the hospital a few days later because it almost punctured my uterus. So, yeah.”
3. He insisted on putting on a robe and wizard hat.
“We tried a bit of roleplay. He insisted on putting on a robe and wizard hat. Things didn’t go too well after that.”
4. Each time he thrust, his stomach kept blocking him from fully entering me.
“Fucked a guy who was a bit on the chubby side. Problem was his stomach was getting in the way of his penis getting inside me and each time he thrust, his stomach kept blocking him from fully entering me.”
5. Went to give him a BJ and it was the length and girth of a Chapstick.
“Went to give him a BJ and it was the length and girth of a Chapstick. It was just really unexpected.”
6. Now I know what dick cheese tastes like.
“I was going down on this uncut guy. His foreskin hadn’t really retracted, so I sort of used my mouth to push it down and get to work. But once it was pushed back, I felt something bumpy on my tongue, and his dick tasted awful. So I pulled off, and his dick head was covered in white crud.
And now I know what dick cheese tastes like. Because apparently a 27-year-old man doesn’t know how to wash himself.”
7. Dude finished and immediately started talking about clowns while laying on top of me.
“Dude finished and immediately started talking about clowns while laying on top of me.”
8. A baseball-sized cyst on my tailbone burst and there was blood and pus EVERYWHERE.
“My first time.
I bled everywhere because a baseball-sized cyst on my tailbone burst and there was blood and pus EVERYWHERE.
Luckily he understood and quietly did the laundry and changed the sheets after getting me a change of clothes and gauze while I literally packed my ass.
Yes, I am marrying him.”
9. His sperm was so bitter that I audibly gagged and retched.
“I took a guy home when we were both completely shitfaced.
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.”
10. Mid-coitus he started chanting, ‘Just screwin’ in my socks!! Screwin’ in my socks.’
“Guy left his socks on (which disturbs me). Mid-coitus he started chanting, ‘Just screwin’ in my socks!! Screwin’ in my socks.’ Over and over. Then promptly finished. He asked if I did, too. I told him if you have to ask the answer is probably ‘no.’”
11. He accidentally smacked me face-first into the bookshelf above the bed.
“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.”
12. He was like flopping around on me.
“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 haha.
Walked out after and never spoke to him again.”
13. If I wanted to fuck myself with a 9-inch dildo I could have stayed at home.
“He had a huge dick. He did not move at all or even make noise. If I wanted to fuck myself with a 9-inch dildo I could have stayed at home. He got off, I did not.”
14. We head to his room, and he turns into a shitty porn star.
“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 shitty porn star. ‘Oh you like that you slut, don’t you? Take it yeahh. Yeah. Yeah you whore’ 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 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.”
15. I have to go into the bathroom and try to fish this rogue condom out of my bloody mess of a vagina.
“This just happened recently! I hadn’t had bad sex until then!
Met the guy on Tinder and we have a bunch in common so I agree to smoke with him at his apartment one evening. We’re really hitting it off, no awkward silences, constant conversation, all that good stuff.
When we went to have sex, he waited about 30-45 seconds before completely pulling my pants down and shirt off. Then he takes not one but two fingers and just starts jabbing them up there over and over again, no preheating of the oven, nothing. Like I guess this is what he considered foreplay. He pulls them out and leaves a bloody handprint on my thigh and I’m just like ‘dude you made me bleed…’ And he just apologizes and moves on. He finished pretty quick too so he goes to get a new condom so we can keep going. It’s taking too long and I’m not enjoying any of it so I just kind of lay there hoping it’ll be over soon and then he looks like he’s starting to get tired so I use that as my out and tell him if he’s tired we can stop so we do. He pulls out and the condom’s gone… I have to go into the bathroom and try to fish this rogue condom out of my bloody mess of a vagina. My friends all say I should’ve left after the bad fingering and I probably should’ve…
I do still like hanging out with this guy though since we have so much in common and he’s super chill, so I simply told him that I’m going to have to teach him some stuff because if we’re ever going to have sex again what he did that night is not going to fly ever again.”
16. What feels like a cupful of semen just pours in me.
“Started out fairly fine. Me (petite) and a slightly taller than me but really skinny guy. He and I had been making out, we’d been in various states of undress, he’d touched my body, done some mouth work over my hips and thighs, etc. It wasn’t amazing but it was nice.
Turns out he’d taken his underwear off while his face was at my hips. He suddenly held my legs and, without a word pinned them back, with my knees to around my armpits and my ankles at my ears. I’m just reacting to this with surprise when I see his body revealed.
His dick looks the length of a wooden school ruler. Or something to measure sea-depth with. And he just swiftly pushes it all into me with only slight pause every two inches or whatever to snug each bit down.
It didn’t hurt as such but it was a kind of, holy shit, feel your body adjusting to being filled with no gaps in one slow push. Just as I started to mentally have a grounding, he withdraws about a third of it and then is all back in again. He did this about three times and then moaned really loudly when all the way in, and what feels like a cupful of semen just pours in me.
Then he relaxed, looked happy and sex was all over. Luckily, I was on the pill but, shit, that went from 50 – 1,000 in twelve seconds.”
17. Pressed his tongue against my clit and then shook his head like a dog.
“Pressed his tongue against my clit and then shook his head like a dog. I don’t know what he was going for but it was a bizarre experience and I kinda just sucked it up and pretended that was okay until he was done.”
18. He passed out while eating me out.
“He passed out while eating me out, like with his entire face heavy and unmoving between my legs for about a minute before I realized it wasn’t a ‘technique,’ and that he was actually asleep. I shook his head to wake him up. he gave me a scrunched up and sour ‘why’d you wake me up?’ face and then DENIED falling asleep in my crotch.”
19. Felt like I was sliding down a dry slip and slide.
“A month ago. Guy couldn’t find my clit and then couldn’t get me wet at all. He tells me ‘Don’t make me do all the work.’ So I start riding his dick. Only it is very painful, because he didn’t put lube on the condom and I’m not wet at all. He goes ‘Do you need an instruction manual?’ This is coming from a 46-year-old that doesn’t know how to eat pussy. It was really bad. Felt like I was sliding down a dry slip and slide. In true fuck boy fashion, he told me my pussy was built weird and he couldn’t last long because I was too tight.”
20. It was like the opposite of giving birth. I wanted to sleep with him but it wouldn’t fit.
“He had the hugest cock I had ever seen. I was so in love with him. But it was like the opposite of giving birth. I wanted to sleep with him but it wouldn’t fit. It was so upsetting. (I was well into adulthood. Sexually experienced. This cock was not to be fucked with.)”
21. His hand slipped and he straight up punched me in the vag.
“Hooked up with a guy back in college. To set the mood he vigorously fingered me to the point his hand slipped and he straight up punched me in the vag. He then rolled over and practically demanded that I blow him.
After a minute of the intentionally worst blowjob I’ve given, he climbed on me and proceeded to make this weird grunting sound to non-rhythmic thrusts. After 30 to 45 seconds looked at me and said, ‘Am I good?’ I didn’t know what to say so I just replied with ‘What?’ But this boy was about 200 pounds crushing my little body so it came out as more of a wheeze which he took in the affirmative.
He then said that he thought he heard his roommates in the bathroom next door so he rolled off of me and barked to get my clothes on. I think he came in less than two minutes but was just too embarrassed to admit it. So I put my pants on and left, never to speak to him again.”
22. He fell asleep, woke up, came on my car seat, then puked all over the inside of my car door.
“Hooked up with a guy I worked with one night at a party. We were making out and decided to take things into my car. Halfway through it went from okay to ‘is this motherfucker asleep?!’ I patted him on the back and was like ‘Dude, are you asleep?’ And he kind of came back mumbled no, proceeded to jam his dick into my inner thigh, despite me telling him it was my leg, then he came in my seat. Moved back over to the passenger side and fucking puked all over the inside of my car door.”
23. I kicked him out and ordered pizza.
“20th birthday this guy drove 2 hours to go down on me for 30 minutes then we had awkward sex where I had to fake it (the one and only time in my life). It was so bad I told him to just go home and I was too tired for anything else. I kicked him out and ordered pizza.”
24. I lost my virginity and almost died!
“So I lost my virginity and almost died! I was in my mid-twenties (I’m a woman) and when I did I was drunk and with a guy I’d only gone out with a few times. I never got around to telling him. I thought it would be fine he didn’t need to know. That is until he stops us because there is a pool of blood. On his comforter. Looked like half a liter of blood. I scramble off the bed to go clean myself off in the bathroom, but I somehow left bloody footprints on the white carpet. Over the next few days it starts to hurt to pee. I just assumed this was normal, but after a few more days of excruciating pain I go to the doctor. Doctor says I have a UTI and gives me meds. Those meds end up not working and leads to a kidney infection and a super-high fever which lands me in the ER. The ER doctors said I almost went into septic shock. So that is the story of how I had sex and almost died!”
25. I had sex with a guy who got off after 5 minutes and left with the used condom in his pocket.
“Worst sex as an adult: Invited a guy over I’d briefly been seeing earlier in the year. He was my type physically but he lacked game. He asked to use my shower before we f*cked because lord knows where he’d been and I obliged. Anyway, we get to business—I go down on him, he doesn’t return the favor (though he had in the past). He ‘gloves up’ and gets inside me, not long into the act I contract my pelvic muscles to enhance both of our pleasure, he grimaces ‘What do you do like a million kegels a day?’ I ask if I’m hurting HIM he says no, and within 2 minutes he grimaces again, shutters, and dismounts—he came and I was barely beginning to enjoy myself. The sex lasted about 5 minutes, he drove 45 to see me.
He takes off the condom, sets it on my bed, I get him a towel to clean himself up, grab the rubber so it doesn’t leak on my bed and as I’m about to throw it in the trash—he asks for it back. I then watch him attempt to tie it in a knot…to take with him. Never saw him again.
TL;DR: I had sex with a guy who got off after 5 minutes and left with the used condom in his pocket.”
26. His dick was so small, it felt like a tampon.
“In 9th grade, I was in love with this popular guy who barely noticed me. Then toward the end of the year, I got boobs and cut my hair and just got generally better looking. We ended up sleeping together on 4th of July that summer. First, the condom was so big on his dick that it kept slipping off. Second, he got on top of me and just started humping my (closed) legs, his dick just flopping around all over my crotch area, not inside. I had to tell him to wait so I could open my legs so he could actually penetrate me. Third, his dick was so small (to give him credit, we were 15 years old so it’s not like I expected him to be huge) that it literally felt like nothing…like a tampon. Fourth, I got my period all over his dick and the white sheets. So that’s great.”
27. He suddenly starts HUMMING AGAINST MY CLIT.
“During sex with a guy who I had known for a while and thought was relatively normal up until that point, he suddenly decides to go down on me and was all like ‘oh man do I have a treat for you’ and suddenly starts HUMMING AGAINST MY CLIT. Like not even sucking or nibbling…with his lips kind of next to it, HUMMING. All the while being like—yeah, you like that, baby?? And I am so pulled out of the moment by the ridiculousness of what he is doing that suddenly I am holding a pillow up to my face to try and stop myself from laughing because he was SO into it and I couldn’t think of anything worse. I couldn’t bring myself to get him to stop because it was so horrifically awkward I didn’t even know how to start. The entire time I was thinking to myself ‘who the hell told you this felt good?’…he was so enthusiastic about it being the best thing I’d ever felt and I was so unimpressed with how unbelievably bad it was that at that precise moment I vowed never to see him again. This guy later offered me free music festival tickets and was planning a fun weekend trip out of it but each time I thought about going I just realized I couldn’t face the humming clit moment ever again.”
28. I was quite surprised when he took off his pants and saw his family jewels were missing several carats.
“Dated this amazing guy who treated me like a princess. He was built like a hockey player so I was quite surprised when he took off his pants and saw his family jewels were missing several carats. In the middle of sex he stopped and said, ‘Whoops, it fell out.’ I didn’t even notice. It wouldn’t have been nearly as bad if he tried to make sex a two-person experience but it was quite obvious that was the one thing he was totally selfish about.”
29. Went about five agonizing minutes of him awkwardly humping me with his limp biscuit before I told him to just stop.
“My first time. He put the condom on and tried to do his thing…all while still being soft. Went about five agonizing minutes of him awkwardly humping me with his limp biscuit before I told him to just stop, and then walked home.”
30. I was dry the entire time.
“A comic with a tickle fet. Ironic. Or not. Anyways not my cup of tea, but I told him everyone has something weird so don’t worry about it. I was very clear that I was not interested in being tickled sexually and hate tickling in general, but this did not stop him. He fully licked both of my armpits with no warning. Could not keep a pace, kept going soft, ended up being somewhat painful for me because he didn’t know how to use his hands and I was dry the entire time. He kept saying he was gonna get hard again to ‘finish me off’ but I was just sitting there like no plz I hate this and no amount of rounds will get me there. Afterwards we were joking around and he apparently had no idea they make porn for everything and pulls up a video of a chick getting tickled and acts like it’s the hottest thing he’s ever seen, which is probably was, but also seems to think I’m enjoying it heartily myself. ‘Do you SEE this?!!!’ I am completely baffled as to how he thinks I enjoyed that tbh don’t be ashamed of yourselves kids. Don’t force your unshared fetishes on your partners, kids.”
31. One painful thrust and motherfucker is done.
“A couple of years ago I started seeing this guy. Super cute, kind of on the shorter side, very athletic and fit. Things start getting hot one night, we’re making out and gettin’ all touchy when all of a sudden his pants just disappear. I swear to God I don’t know how he got them off that fast. He grabs the waistband of my pants, rips them off and slams his rather large dick balls deep into my not-so-ready crumpet hole. I’m shocked, scared and slightly in pain. THEN without even moving he cums immediately! That was it. One painful thrust and motherfucker is done. I got up without a word. Put my pants on and left while he lit up a cigarette. Worst sex ever.”
32. I started sucking on his dick when the stench hit me like molten lava.
“I was giving head to my boyfriend and he was laying in his bed. I started sucking on his dick when the stench hit me like molten lava. I told him it smells like shit but he could not smell it and was really into it. After a few mins…I said no way and finally he got up…turns out his Chihuahua shit in his bed and when he laid down shit was in his ass! He jumped up and had dog shit dingleberries hanging from his asshole pubes and I was forever revolted and scarred for life.”