35 People Reveal The Most Excruciatingly Awkward Sex Experience They’ve Ever Had

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

1. Literally less than an inch.

“One word. Micropenis. Literally less than an inch. I thought I was on Punk’d.”

2. Two, three inches maximum.

“Met a guy who said he hadn’t had sex in 7 years, we got along pretty well so I told him I’d give him a pity fuck. He gets it out and it’s like 2, 3 inches maximum. I ask him if he’s ready, thinking maybe he’s nervous and a grower, not a shower. Turns out he’s hard, shit. He puts a condom on, and it was legit baggy. Let’s just say, the fingering filled me up more than the actual sex. I feel bad about it still, but he was happy, that was my intention so that’s what mattered. Also, doing that with me gave him the confidence to ask another girl out, who seems to be happy with him. I guess I took one for the team.”

3. He had the worst breath I’ve ever smelled and horrible body odor.

“He had talked himself up so much (that should have been my first clue), and then come time to actually have sexy times he had the worst breath I’ve ever smelled, he had horrible body odor (even though he’d just taken a shower), he kissed like he was an oxygen mask (whole mouth over almost my nose and mouth and he kept licking me), then he couldn’t get it up to fuck me, and when he finally managed to get it up, he apparently started thinking about his ex-girlfriend and started sobbing. Never again.”

4. From crappy sex to suicide watch in ten seconds.

“I went back to a guy’s house who was a friend of a friend. We were both drunk, stuff starts happened and we are alternating oral, general foreplay stuff. Suddenly he gets up, runs to the bathroom, I assume he is going to be sick but a moment later I hear sobbing.

I walk in and he is bent double in the middle of the room crying his eyes out, I ask him what’s up and he goes:

‘I’m fat, I’m ugly, nobody likes me.’

Went from crappy sex to suicide watch in ten seconds.”

5. The couch ate my balls.

“Was having sex with my ex on the couch. I was seated and she was straddling me facing me. Thing is our couch was a hide-a-bed and I’d slid down so that my ass was pretty close to the edge. As she kept rocking back and forth, the cushion under my ass kept shifting, too. Before long the positions lined up just the wrong way and my balls slid off the front of the cushion and when we rocked forward again they got caught between the front of the cushion and the front wall of the hide-a-bed. Difficult to explain in words if you haven’t really seen old hide-a-bed couches. It hurt, but not so bad that I didn’t try to recover and keep going. But with every stroke they just got grabbed and squeezed again. Just couldn’t keep going. Shifting required explanation, explanation provoked laughing from both of us and sexy times were momentarily postponed while our sense of humor and my balls recovered.”

6. A blow-up doll would have shown more emotion and made more sound.

“One-night stand, I met her having a drink after taking photos of a concert she was at. Talking was fun, she looked good and making out was OK but once we got to her room everything went downhill fast, she was a total starfish and just didn’t do anything anymore once we got naked. I mean she did actually nothing, no blowjob, didn’t want me to go down on her or anything but penis in vagina and once that happened…Let’s just say a blow-up doll would have shown more emotion and made more sound.
And to add insult to injury she had a single bed so it wasn’t comfortable sleeping either. I got out of there before breakfast.”

7. He basically used my face like I was the dead frog in the video of the monkey.

“He basically used my face like I was the dead frog in the video of the monkey. The only reason I continued having sex with him was to see just how bad it could get. He announced seconds after he came that he was leaving the country indefinitely the following week and he needed to go pack. I was obviously gutted.”

8. She texted me…from her phone…to accuse me of stealing her phone.

“This weird German girl I brought home who kept trying to bite my nose and then texted me the next day accusing me of stealing her phone. FROM HER FUCKING PHONE!”

9. I fucked a girl into a heart attack.

“I was dating let’s say Felicity in high school. She was on the color guard. Amazing breasts beautiful blonde hair and two years older than me. She was a huge health nut, ate a copious amount of salt for no explicit reason. She came from a huge family and I had homebody parents. Neither of us had cars so finding a spot to do the deed was really hard. Finally the stars aligned one night. Her whole family was out and I went to her house. So we’re in the basement we’re making out. This is amazing. So I’m hittin’ it from the back right? And she starts making this shrill gasping noise. HUGH! HUGH! HUGH! Now at this point I knew moans and screams meant I wasn’t hurting her. But this was a new noise. I thought through all the porn I had watched over my fap-addled life and nothing matched this noise. I had stopped and she still was making it. HUGH! HUGH! HUGH! I flipped her over and she can’t breathe. She’s going into a seizure. So I try to call an ambulance. My phone is dead I reach for hers it’s on the charger. She has a passcode and it’s not her birthday and I didn’t think about the emergency button. I go to find their home phone and they don’t have one. They’re one of those new everyone-has-a-cell-phone families. So I sprint next door in my boxers and unbuttoned shirt at 1 in the morning banging on their door trying to explain that I needed an ambulance and don’t call her parents.

Finally, it comes. She has a weak heart. Even getting aroused could send her into cardiac arrest. So she hadn’t even seen a dick up to that point and won’t look at men online. She ate a ton of salt so her blood would be thicker or something. Her parents found out and I wasn’t allowed to see her again. She’s fine now. I haven’t heard from her in years.

tl;dr; It’s a good story man, just read it. But I fucked a girl into a heart attack.”

10. Three-pump chump.

“Worst is this guy I met at a bar my last night living in New York. When we started getting down and dirty he went down on me for about ten seconds and just did these weird kind of licks all over between my legs, pretty much totally avoiding where he needed to actually be. Once he came up from that he gave me about three pumps, came, and flopped down next to me breathing like we’d just had some all-night fuckfest. Get ready for this. First he rolled over and asked me how many times I came. It was hard not to laugh and harder to not tell him I didn’t even get aroused. Then he told me I was the second person he’d ever had sex with. THEN he told me was very excited about where our relationship was going to go. Broke his heart when I pointed to all the packed boxes surrounding us and told him I was moving across the country in the morning.”

11. The stinkiest stank I’ve ever smelled.

“Girl had a shallow vagina, and sex was awful so I decide to at least go down on her. We had just eaten sushi and I guess the liquor in my belly wasn’t settling right. I get down to do my business, and it is hands down the stinkiest stank I’ve ever smelled. I hold my breath and dive in (the gentleman’s move). It smells so bad, and the sushi/whisky combo was so unsettling, I threw up in my mouth, quietly spit it onto the floor under her bed, and kept on going…”

12. Thirty seconds and the whole thing was over.

“I hooked up with a girl at a friend’s wedding. I was going slow and kind of working it in when she says ‘just go in as far as you can.’ So I press my pelvis against hers, she trembles, holds me there a second, and then lets out a tiny gasp and then goes noticeably limp. She then says ‘What, you can’t cum?’ ‘…What?’ ‘Did you not get off?’ ‘…Well, we just started and—’ As she is kicking me off of her, ‘Well, I guess I just know what I like. You can take care yourself now, right?’

I have never been with anyone so selfish. It’s how I imagined most girls in my high school felt. 30 seconds and the whole thing was over. The most disappointing part was; she was soooooo hot.”

13. A heck of a lot of blood.

“First time with my then-boyfriend, we were in a very dark room. I went down on him and he seemed to enjoy when I was using a fair bit of suction on him, so I kept doing it. Approximately 20 minutes-ish later, as he was almost about to orgasm, I started tasting blood. Like, it was coating my mouth bloody-blood. I panicked and told him I tasted blood. He turned the bedside lamp on and saw that my entire lower-face and his shaft was covered in blood. He started freaking out, lost his erection within seconds but we then realized it was not his genitals but my lips that was bleeding; I am a lip biter and had injured my lips. The suction seemed to have caused bleeding, which mixed with all the other fluids, seemed like a heck of a lot of blood.”

14. I fell out of his truck head-first.

“Found out that he lived with his mom so we had sex while parked along a deserted road. Well, attempted to but his truck was rather small for both of us so he opened the passenger door and long story short…I fell out head-first…”

15. Never lose your virginity to a witch on the beach.

“My worst was losing my virginity on the beach. I was 16 and met this girl in an AOL chatroom. I picked her up in my AMC Eagle and, I hate to sound judgmental, she didn’t exactly look the way she had described (kind of like if you thought you were getting a VW Bug and got a VW Bus instead). But I was 16 and wanted to get rid of my virginity like it was a boil on my ass, so off we went.

Anyhoo, sex on a beach sounds like a good idea until you actually try it. Sand gets into places where sand does not belong, you can catch more than one type of crab, and even if it’s dark out you still run the risk of getting caught which makes you paranoid. All of those things were racing through my young virgin mind as I was gyrating terribly for about 30 seconds on top of this poor girl. I farted when I came all over her. It was awful.

We went to the same high school, but completely different social circles. After we banged, I felt so ashamed of the whole situation I vowed to avoid her at all costs. Not the most mature decision, but hey, I was a dumb 16-year-old. Add to that, she had mentioned that she was really into Wicca and when I stopped talking to her she got mad and sent me an IM that she had put a curse on me. My life has been in a downward spiral ever since. Never lose your virginity to a witch on the beach.”

16. A tiny-dicked 25-year-old virgin.

“Guy was 25, admitted he was a virgin casually while nearly being undressed. Didn’t judge him. Didn’t judge him at all. Then he proceeded to get undressed. He had the tiniest dick. Started to feel really, really bad for this guy honestly. But we still shared the bed, tried to make his first time worth it. Wasn’t good for me at all, he went down on there between my legs at one point like a fatty on a free buffet, but you know, it was his first time, we managed. Then the next morning he ran out, told me I was cheaper than a whore cause he fucked me for free. Pretty rich coming from a tiny-dicked 25-year-old virgin.”

17. Her vagina and ass together are making the most putrid smell I have probably ever smelt before.

“Alright, so one day a few years back I’m on a dating website and I meet a girl who I’ll call Stephanie. Stephanie was a little overweight but still a very cute girl. We texted for a few days just getting to know each other. One night on a Wednesday she texts me saying we should meet up to make out. I say hell yeah and proceed to take a shower. It’s about 10PM and I know that two 21-year-olds aren’t going to meet up to just make out. I take my shower and we agree to park our cars on the side of a movie theater a few towns over (where she is from). She gets out of her car and she is wearing leggings and a shirt that shows basically everything but her nipples (it was awesome). I drove a Ford Explorer at the time with the third row seating. I turn off my car and we get into the back seat to start making out. Within about a minute I’m going for boob. Stephanie said something along the lines of ‘I thought we were just going to kiss.’ I told her that was fine but just thought it was code words since we were 21 and I had brought condoms just in case. She decided she wanted to blow me, hell yeah. She starts doing the deed basically bent over my back seat while I’m in a corner being taken on an amazing journey to pleasure town. This is when this tragic love story takes the fall. I peel down Stephanie’s leggings and start to finger her. After about a minute I smell what smells like legit feces. I thought she may have just farted so I keep going till I realize that her vagina and ass together are making the most putrid smell I have probably ever smelt before. I casually try and hit the window lower button on the back door but then I realize I turned off my car and my keys are sitting in the front seat. Right as I’m about to call things off she takes off her pants and gets on top of me while reaching in my center console for the condoms. Being the man I am I decided I was going to hit this. She proceeded to put a condom on me and rode me for 45 minutes straight before my body gave me a pity orgasm. We parted ways. I get back to my apartment and tell my roommate (and best friend) to come out to my car with me. I make him smell what just happened and he proceeded to dry heave while I explained what I had just done.”

18. His sweat dripped into my mouth and eyes.

“My college boyfriend and I had been dating for about two weeks. He was a virgin and I knew that. I had only had one other sexual partner and admittedly was not good at sex either, very self-conscious. Because he was a virgin I was less self-conscious. He was very very nervous and also very sweaty. I ended up having to stop him because his sweat dripped into my mouth and eyes. We’re married now and are both MUCH better. He’s still sweaty, but I love him.”

19. My nuts were bleeding.

“I got a blow job in the middle of the road in the middle of town in the middle of the night. I was absolute sure every car I heard on side streets was a cop coming to arrest me. I exploded so hard in her mouth it gave me a headache that lasted the entire next day. I almost went to the doctor.
Worst: I was home visiting when a girl I knew from high school hit me up on Facebook. We spent almost a week hanging out when we go snowshoeing. We start getting frisky out in the middle of nowhere and its frickin’ cold. My pants are at my ankles and she’s blowing me. I’m having a difficult time keeping it up my nuts are so cold. I lay her on her back and go to pound town. I faked finishing my nuts were so cold I couldn’t feel them anymore. I pull up my pants and we get back to hiking. The longer we hike the more my nuts are hurting. I stop to pee and I go take a look at my nuts while I’m peeing. They are bleeding. I rub them raw but couldn’t feel them rubbing against the solid snow during sex. Fast forward 9 months she introduces me at her wedding to her new husband as the guy who took her virginity.”

20. She started biting pretty much everywhere on my body.

“So I met this girl on Tinder, she looked like a freak (crazy hair colors, piercings all over, tattoos, and was a ‘model’ (let some dude take sexy pics of her). I invited her over to my place to Netflix and chill or whatever. So, things start getting hot and heavy, and we start touching each other and ripping each other’s clothes off. Once I got my shirt off, I knew I wasn’t having fun anymore. This chick, this motherfucker, bites my nipple so fucking hard that it starts bleeding. I was like alright, it doesn’t hurt that bad now and my dick is in her mouth (hopefully she doesn’t bite down again). Thank god she didn’t, but the next 25 mins consisted of sex, me screaming ‘ow’ due to her biting pretty much everywhere else on my body, and her calling me a pussy BC ‘I didn’t like it rough.’ The kicker, she was cheating on her boyfriend that I had no idea existed and got an STD from her even though we used a condom.”

21. He literally screamed when he orgasmed.

“Worst: the guy who literally screamed when he orgasmed. No joke AAAAAHHHHHHHOOOOOOOO!!!!! At top volume while I laid there trying not to look horrified. Then offered me wah wah. Hmm? Wah wah… umm water? Are you offering me water? I noped out of there quickly.”

22. My ex tore off my clit hood.

“Oh shit, my worst has to be when my ex tore off my clit hood. It was pretty heated, he was finger-blasting hard and fast until he went to put his fingers in but missed the hole and his sharp nails caught my hood and tore it off. It was legit dangling off, bleeding. I was screaming in agony. It turned purple and then black. I was 15 at the time and had to show my mum that it was dangling off. She found it both disgusting and hysterical.”

23. Her dad walked in with a shotgun.

“We were spooning in her basement watching a movie while her parents were up half a staircase in the living room. She was a nympho and one thing led to another and we started going at it. I heard footsteps and I threw a blanket over us and opened my phone pretending to be on Twitter as her dad walks in carrying a fucking 12-gauge shotgun all casual. Turns out he was sitting in the living room cleaning his guns that day, and he was walking through the basement to put his now clean shotgun into back into his safe in the garage. He stopped and asked ‘how are you kids doing in here, everything alright?’ I could barely choke out a ‘Yes sir, just watching a movie,’ I was damn near sweating a hole into the couch. He put his shotgun away and went back to finish cleaning the others. I didn’t stay to see what else he had in his collection, told her I forgot to finish my math homework, left, and that was the last I’ve seen of her.

TL;DR I was smackin’ stomachs with this girl when her dad walked in with a shotgun to help me finish my math homework.”

24. I barely felt his dick in my ass.

“Was having sex with some fellow I met earlier in the week in my camping trailer with an impressively small dick. He was fucking me doggy style when I felt some pressure around my ass—and the tiniest pop. ‘Did you just slip into my ass?’ I asked. Yep. He was that small, I barely felt his dick in my ass. He also came within 2 minutes. So there’s that.”

25. I don’t think she wiped her ass last time she took a shit.

“There are a couple of pretty bad ones, but this one takes the cake. I was horny and not really picky to get laid. Met a girl on Craigslist who was looking to play as well. She was a little heavier but not huge. She did not take care of herself well at all. Low grooming, and the smell—I don’t think she wiped her ass last time she took a shit. My boner died on the vine, and although I did take a quick dip, I just couldn’t go on. I told her I felt sick and asked her to leave. Blocked her number.”

26. A mushroom in a moss patch.

“I took off his disappointing tighty-whities to reveal what appeared to be a mushroom in a moss patch. at some point he said ‘mount me’… which killed any enthusiasm I had left. he laid in the masonry position and I did my best but not being able to even feel him was confusing and embarrassing. he laid there for a good 15 minutes, motionless and expressionless till I faked an orgasm, lied and said I was too sensitive to continue and then got dressed. he said he’d give me a ride back home then he fell asleep on the couch. I walked the 5 miles home.”

27. Her ass hair poked me in the eyeball.

“69ed with a girl who had a hairy asshole. She moved and a hair poked me in the eyeball. Never slept with her again.”

28. The floor and tiles were covered in blood.

“In college a girl I was with got a vaginal wall tear that made her bleed so bad, the floor and tiles were covered in blood and she passed out. I ended up carrying her down to a cab (we were a few blocks away from the hospital and it was the middle of the night) and an officer at the hospital kept pressing me if I abused her. It was so scary.”

29. The smell was so horrible I had to stop and ask her to take a shower.

“I had been flirting heavily with this one really attractive, petite woman and we kept missing our opportunity to get together. So when we did, we basically flew back to my house. I get her naked and she’s just beautiful but I got a head blow and a gut check at the same time when I went down on her. First, when I curled my hands around her butt to lift her up to me a little bit, my fingers curled into what could only be described as a thatch of steel wool ass hairs (she was completely shaven up front). And yet I sallied forth, skipped the cunnilingus, and plunged in, the smell was so horrible I had to stop and ask her to take a shower. She got pissed and left and we never spoke again.”

30. Girl smelled like a Sea World exhibit.

“Girl smelled like a Sea World exhibit. Fake finished and ran to the shower. Turned out she had a tampon up there she forgot about.”

31. His dick was covered with white crusty gunk.

“I went to give him a blowjob. He was uncut, so I pulled his foreskin back with my hand as I pushed my mouth down. The head of his dick felt a little rough and tasted gross. Pulled back to look, it was covered with white crusty gunk.”

32. She smelled like she threw up and took a shit on herself.

“I’m drunk, and coming back from the bar horny with no luck, hit up Tinder and match instantly with a chick. She’s down to meet at my place, I barely remember the night, woke up the next day next to a girl three times my size and she smells so bad. Like she threw up and took a shit on herself. I get her out of my place. And then she becomes my stalker for the next couple of months till I move. Deleted Tinder after that.”

33. Her pussy stank like a gangrenous limb.

“Pussy stank so bad it hit my brain right when the pants came off. Boner killed, no sex happened and I scrambled for an excuse to get the fuck out. Total fight or flight response, like smelling a gangrenous limb. Took about a week to get sexually excited about anything after that trauma.”

34. A fountain of blood.

“First time sex with a new girl, going down on her. Everything’s great, until she unexpectedly climaxes and slam her thighs together. Now, I easily get nose bleeds, and this started a real gusher, and she was very shocked and apologetic. Next day, we try again. This time, I’m prepared, so I have my arms poised to hold her legs. However, this time, as she comes, she bucks and, once again, mashes my nose, this time causing almost a fountain of blood. I’m used to nosebleeds, so I don’t mind much, except for the interruption, but she started crying. Luckily, I soon found out that she was a bit crazy, and it ended within a week.”

35. The smell of rancid garbage smacked me in the face.

“My first time, I was in my basement after school with my sister upstairs doing homework. I’m obviously and very noticeably nervous. Girl asks if I’ve ever had sex before, and as a high school freshman who wanted to seem cool, the answer was obviously yes. We get undressed, I move to go down on her, being a gentleman and all. I get about 8 inches away before the smell of rancid garbage smacks me in the face. I end up just kissing down her stomach and going right back where I came from. Anyway, we do the deed, which lasts all of 20 seconds before I’m flaccid and disgusted with myself. Long- term, she stopped coming into school after that, and I had a panic attack thinking I got her pregnant. I ran into her a few months later and asked her why she hasn’t been at school. Turns out she had had a bad reaction to her antidepressants and they had made her make some “bad decisions” that she really regretted.”
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