Awkward Sex: 35 People Confess Their Most Cringeworthy Moment In The Sack

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

1. I went into jail with one sock and a condom still on.

“Went to our spot that we have sex in kind of up the mountains in her car. Having sex we see a bunch of officers hauling ass up the mountains in their cruisers. We worry about getting caught naked in her car which is 50 feet away from the road. They eventually find us and run our id’s because a car was lit on fire in the area. Turns out I have a warrant for not paying a ticket when when I was 17 i just turned 18. So they hand cuffed me and took me in to jail for 3 days. I went into jail with one sock and a condom still on.”


2. I accidentally jizzed on the cat when I pulled out of the lady.

“I accidentally jizzed on the cat when I pulled out of the lady. Oops!”


3. Dog walked in, stood, stared, threw up on the floor and promptly left.

“Dog walked in, stood, stared, threw up on the floor and promptly left.”


4. I was in hospital all night with a ‘broken’ dick.

“Girl goes up, Girl comes down. Girl goes up, Girl comes down. But misses. I was in hospital all night with a ‘broken’ dick.”


5. When I removed my mouth from her boob, blood poured out of my mouth onto her chest.

“Was trying to give a girl a hickey on her boob during foreplay. I sucked pretty hard but when I removed my mouth from her boob, blood poured out of my mouth onto her chest.

‘So that’s what AIDS tastes like.’ Just tried to make light of the situation so we could continue.”


6. My first boyfriend gave me a hickey on my nose.

“My first boyfriend gave me a hickey on my nose. I had to tell my mom I bumped into a drawer that had been pulled out that I didn’t see. Then I had to convince her than no it wasn’t broken and she really didn’t need to take me to the ER.”


7. It flew like a goddamned seagull into her nose.

“Worst sex I ever had: We were pressed for time, the room was too hot, she had a rash she couldn’t stop itching, and I had a horrible leg cramp. We were stubborn and horny, so we kept going. In an awkward missionary off-the-bed kind of way, I eventually reached an orgasm, pulling out quickly when I did (she was on the pill, but I was always paranoid).

Wouldn’t you know it, it all came out in one. fucking. glob.

And it flew like a goddamned seagull.

Right up, past her stomach, past her chest.

Into her nose.

All of it.”


8. I met the family of a one-night stand and realized I fucked her little sister as well.

“Meeting the family of a one-night stand and realizing you fucked her little sister as well.”


9. There were some unanticipated ‘muscle relaxing’ effects of the drug.

“I had taken some muscle relaxants and anti-inflammatories for an injury and then headed to a bar to relax (not the smartest combo).

That happened to be the night that I picked up a chick who was way out of my league and brought her back to my place (not exactly a regular occurrence for me). Things started getting naked and sweaty and then the unanticipated ‘muscle relaxing’ effect of the drugs reared its ugly head I had to use that most dreaded of lines for a horny twenty five year old guy;

‘I swear, this has never happened before.’ :-(”


10. The mum walks in while her daughter is on top of me, tits in the breeze.

“First story:

Had an ex GF who was 18 at the time and living with parents. We had a morning shag, thinking her parents had left like they told us they would the night before. Nope. The mum walks in while her daughter is on top of me, tits in the breeze. Her mum fucking puts down two cups of tea and tells us breakfast is in ten minutes, as if nothing was happening.

I think it was some passive aggressive way of telling me not to fuck her daughter in her house.

Second story:

Same girl, about two months later. I’m in my room with her on top, totally uncovered and MY mother walks in this time, trying to offer us biscuits. My mother is the sort who never fucking knocks, not even on the door to the the loo. Always argued with her to knock. Well this night she got an eyeful of my ex’s back passage, as the way my bed was positioned meant that opening that door gave about as clear a view as possible of her ass and my dick inside her. Mother learned to knock on doors the hard way. Literally no words were ever said about it. It’s treated as though it never happened.”


11. I puked vegetable lasagna and salad all over his lap.

“My boyfriend unexpectedly shoved my head down on his dick to encourage some deep throat action. I wasn’t prepared and he hit my gag reflex. I puked vegetable lasagna and salad all over his lap.”


12. My brother walked in on me giving a guy a blowjob with my top off.

“My brother walked in on me giving a guy a blowjob with my top off. He apologized and stepped outside. I offered to carry on with the guy in my room but I think he was scared of my brother and went home instead. My brother said he felt bad for cock blocking the guy.”


13. She yelled out, ‘It’s been so long since I’ve fucked my boyfriend’ and started crying.

“My first time was super-duper awkward. It actually started out pretty good, then she yelled out something along the lines of ‘it’s been so long since I’ve fucked my boyfriend,’ then she started crying. Pretty terrible.”


14. He couldn’t stay hard because he was so nervous.

“It was my first time, and it was also my boyfriend’s first time. We did it in a themed motel room with a statue of Poseidon looming over the bed. He couldn’t stay hard because he was so nervous, and eventually broke down crying.

That was 10 years ago when we were teenagers. We’re getting married next year.”


15. I almost fucked my girlfriend into a wheelchair.

“12 years ago, my then girlfriend went on a trip to the east and west coast of the US for 3 weeks. I stayed in Amsterdam to pay off my student loans. When she came back, we had some catching up to do.

I recently got a Kama Sutra book as a joke gift, and we thought it would be fun to try some of the poses. Put the mattress on the floor, and got at it. After a few impossible poses, we tried one where she would lean on her elbows and neck, and throw her pelvis up vertically, and I would stand cross legged, and trust down. This one actually worked. After a minute she lost balance, fell over, and her neck made a really loud snap noise. We both looked at each other surprised and had a nervous chuckle. We stopped with the Kama Sutra poses and decided to go back to our favorites.

After a few minutes her legs started to tingle, and we stopped, she laid down, and said she wasn’t feeling her legs anymore. I froze up, and thought she was joking, she wasn’t. I poked her in places to see where she could still feel. Waist down no feeling at all. She could not stand up either. I was like shit shit shit, and started to panic.

We had to call an ambulance, but her mother, who slept downstairs did not know we where having sex (conservative Buddhist), so we made up a story that she fell down while going to the bathroom. Ambulance called, and I woke up her mother. She was kind of confused about it all, but genuinely did not suspect anything, being a bit naive because of the cultural difference.

Ambulance arrive. They come up, and immediately understand what happens, they chuckle, but are very polite. She is completely naked under a blanket, and isn’t allowed to move, so putting on clothes wasn’t an option. They put a neck brace on her, and transferred her to a stretcher wrapped in the blanked. She was laying in the attic of an old style Amsterdam canal house. The stairs are really steep and narrow. So they could not carry her down on the stretcher. They call the fire department.

The fire department arrives. They all come up to the attic, all 7 of em, in full gear, standing around us, chuckling, but again they are very helpful and polite. They make a plan to use the ladder on the truck and move it towards the attic window, put the stretcher on a small lift, and slowly take her down to street level.

They go down stairs, and I go with them to fill in some paperwork. Then the head fireman says to me that a tree was in the way of getting the ladder tot the roof window, and they would probably need to cut it. It’s a 150 year old tree, and is part of the city heritage. I begged them not to, and they found a way to get around it thank god.

They get her down, and she’s put into the ambulance, her mother sat with her in the back, I sit shotgun with the driver. The driver asked me what happened, but I keep to the story of her falling down going to the bathroom.

We arrive at the hospital. They put her under the X-ray machine, and while we wait for the photo’s to develop, the doctor asks us about what happened. He was looking at me, and then her, he was suggesting to her that she does not have to be afraid to tell him, and was probably suggesting that there was some sort of domestic violence going on. She shook her head, and looked at her mother. Then used a very old fashioned definition of having intercourse so her mother would not understand, and the doctor started laughing and instantly said: ‘Ok, ok I get it, it’s alright. I’ll get the X-ray photos.’

He came back and told us he did not see anything on the x-ray photos, and that it could have been a swollen muscle oppressing a few nerves in her back. She said she really needed to pee. and the doctor said she would be able to stand up and walk by now. Carefully he helped her sit up, and then she made a few small steps. I was never as revealed about something in my life. She went to the toilet, and slowly walked back. Doc said all she needed was some rest, and sent us home. It was 5am in the morning when we finally arrived back at her home, and got some sleep.

The next morning she was feeling rather well, and the tingling in her legs was as good as gone. Since we still didn’t have sex in 3 weeks, and had all this adrenaline and endorphins going through our bodies because of the night before, we did not find ourselves sleeping at all that night. Best sex I ever had.

tldr; Almost fucked my girlfriend into a wheelchair.


16. My hand was still very very wet when I shook his hand.

“Where I used to live had a neighbor who was always coming round to chat, and wouldn’t leave no matter how many cues you gave him that you were otherwise occupied. My girlfriend had come over for a long weekend and we were making the most of it. We are both mid-orgasm when there’s a knock on the door. The lights are on, my car is in the driveway, he knows I’m home. Keeps knocking as I pull out, get dressed quickly and go downstairs. Open the door, end up having to have a five minute talk with this guy, mostly about the new job I was going to. At the end of the convo he shakes my hand. The sex I had just finished had included a lot of manual masturbation, and my gf at the time used to get very very wet and it was 100% still all over my fingers and palm when I shook his hand.”


17. My stepdad phoned me to tell me that everyone in the living room had heard me.

“20 and living at home, my bedroom was above the living room and i was having sex with my then girlfriend on my incredibly squeaky/busted metal double bed.

About 10 minutes after my stepdad phoned me to tell me that everyone in the living room had heard me and my Mum had called him to ask him to call me to tell me to keep the noise down.

He did congratulate me but said my Mum was incredibly embarrassed.

I wanted to die.”


18. She told me to ‘play dead.’

“You know when you get so lucky you can’t enjoy it because you’re always looking over your shoulder waiting for Karma to kick your ass? Well I was flirting with a California upper 9. She was gorgeous and had no business in little league with me, but to my amazement we hit it off. After a few dates I rented a hotel and she agreed to come over and share it. This is when I became nervous. They say the hairs on the back of your neck stand on end just before you get struck by lightening. That’s how I felt. But things went great. The sex was great, she looked great, and I preformed sub par which was great since I was expecting worse. However, the next morning I thought I’d try my luck again. Things were moving along quite nicely until she stopped, looked me in my eyes, and said, ‘Play dead.’ ‘What?,’ I asked. She told me do not move. Do not speak. Just pretend you’re not alive. Now on the one hand, I know this isn’t normal, rational behavior. On the other, I’m horny and even if I make love to Katy Perry she’ll still be the hottest girl I get with so I agree. This time sex was terrible. The more into it she gets the more dirty I feel. I came, but it felt more like a defense mechanism than anything else. I thought she’d break my heart, but it was me that never called her back.”


19. The one who looked like a rat gave me a handjob.

“Went out with a friend who struck up a conversation with two girls. Became clear neither were interested in my friend so he went home. I got on with both girls and the prospect of a threesome became somewhat real. Someone said we should go back to mine. On the way, the one I was attracted to said ‘if we’re going to have a threesome you should put your arm around both of us,’ which I did but I felt like a moron.

When we got home, the one I liked immediately went to sleep and the other one who looked like a rat gave me a handjob but I was disappointed and drunk so it took me 20 minutes to come. Some come went on her top and she got pretty angry. At some point I did that whiny begging for a blowjob that teenagers do and the other girl mumbled ‘shut up.’

Absolute fucking disaster.”


20. I once gave sideways oral to a girl.

“I once gave sideways oral to a girl.

There’s not really much story behind that. Basically, she had a twin size bed, which made for very difficult re-positioning mobility. So rather than get up and move my whole body down to the foot of the bed, I decided to try to just move my upper half down. The result was my face reaching her vagina in such a way that my lips were parallel with her lips.

Needless to say, I got about ten seconds in before I was like ‘Wtf am I doing’ and gave up.”


21. Someone from my girlfriend’s family watched me fuck her in the ass, at worst, for 5 minutes.

“TL:DR; Someone from my girlfriend’s family watched me fuck her in the ass, at worst, for 5 minutes.

Back in my teenage years when I was fucking my girlfriend (who at the time was 14 years old) in the ass. She was on her knees, legs spread, ass wide open towards the door and I was playing with her asshole sliding my dick in and out as she jerked off with a vibrator I had bought her.

I glance at the wall in front of us and see a faint light shining on it that isn’t coming from the room. I don’t think much of it since you see car headlights shine into the room quite often through the window and I was too busy playing with her asshole to think more of it.

I play with her asshole for about 5 minutes more before she cums and I finish myself off into her ass…I pull out, watch her push the cum out and I wipe her asshole with a warm wet towel. I lean in to kiss her and happen to glance at the wall again and see the light still there. Not a good sign. I turn around and see someone’s shadow under the door walk away.

I panic. I say nothing to my girlfriend who is still face-down-ass-up on the bed. I don’t know how long someone was watching us and I don’t know who it was. Her mum, dad and her little sister were all at home…but usually you hear it very well if anyone walks upstairs where her room is.

I’ve never felt more awkward, ashamed, and creeped out at the same time.”


22. All of a sudden we see a spotlight coming around the corner and we both panic.

“I was at a party with my girlfriend at the time (16 years old, the both of us), and we were both ridiculously horny teenagers. The party was at a friend’s house, almost like family to me, very comfortable in their home. So my gf and I tried to find a room to ourselves, with no luck. We drink a little bit more UV Blue (lol) and we really want to get alone. We decide to walk half a block away to the middle school at 11:30 PM and find that the playground is empty and dark. Big surprise! We make our way over to the tunnel slide and both make our way in. Why the slide? I don’t know. We both get each other going if you know what I mean. I start to take her pants off and throw them to the bottom of the slide, and I’m sliding off my pants and putting on my rain coat, when all of a sudden we see a spotlight coming around the corner and we both panic. We climb a little higher into the slide and try to hide, but the spotlight comes closer and closer and shines right inside the slide.

‘What are you kids doing tonight?!’ says the cop. We’re both in a panic and frozen. I slide to the bottom, grab her pants off the ground, toss them into her, and tell the officer she’ll need a moment. As I’m standing there with my dick going limp fully wrapped trying not to make the situation any worse.

He actually laughs about the whole thing, but says we’re out after curfew, and he’ll have to call our parents. After a little bit of talking he agrees to take us back to my friend’s house and release us to my friend’s parents, while explaining the whole situation to them.

I’m expecting them to be furious with me, but as soon as the cop leaves they look at me, laugh furiously about the situation, and her dad says, ‘Good thing he didn’t smell my pot.’”


23. Out of nowhere she starts crying uncontrollably while still sucking my dick.

“Alright so I was 19 at the time and went to a birthday party at this girl’s house. The girl who was hosting the party had been interested in me in the past but nothing had happened as I was not too interested myself. 6 hours later and 1 bottle of vodka down the party is quieting down and most people are leaving. Now I am just talking to her and a friend of ours in this room and the friend just randomly goes ‘I’m going to leave you guys to it.’ I was really drunk at this point so I was confused when he said this and did not understand what he meant until the girl came over to me and started making out with me. Then the remaining people at the party come into the room 5 minutes later and all wave good bye saying they are leaving, so it is just me and the girl left making out. She goes and gets a condom but me being so fucking drunk can’t get it up. She gets down and starts sucking my dick and after about 5-10 minutes its finally ready to plough the tunnels. But then out of nowhere she starts crying uncontrollably while still sucking my dick. I had no idea what the hell was going on. She takes my dick out of her mouth and goes ‘Guys only ever want me for sex’ and just continues crying and goes over on the couch. At this point I am just standing there with my dick out wondering what the fuck is going on while trying to tell her to keep quiet as her dad is in the house. After about 30 minutes of me calming her down and her going to sleep I get a lift home and try and forget that moment ever happened.”


24. The husband jizzed and some of it landed on my back.

“When I was 19 I lost my virginity to an older, married woman. While we were having sex, both her husband and the guy that owned the condominium we were at barged into the bedroom completely naked and started jerking off over top me while screaming in my face to ‘give it to her; give it to the bitch good!’ I totally wasn’t expecting this interruption, and it was fucked up and weird. Part of me wanted to just get up and split but the other part of me was like, ‘Fuck this, I’m 19 and tired of pretending along when buddies start talking about pussy, and lying about boobs feeling like bags of sand and shit,’ So I just basically closed my eyes and powered through it. It’s wasn’t sexy at all anymore; it was just a task of tuning out the naked dudes masturbating over top me and yelling at me and mechanically completing a task I’d been given. I’m pretty sure at some point the husband jizzed and some of it landed on my back and shoulder but I wasn’t even mentally there in the room anymore by that point. Afterwards I showered and when I came out of the bathroom two of my buddies were on the bed spit roasting her and the two men were hollering again. My buddies encouraged me to join in again, pointing out she still had two free hands. I declined and they did the Eiffel Tower high-five and I just walked out of the room. I went downstairs and grabbed a beer out of the dude that owned the condo’s fridge and sat on the sofa and just thought, ‘What the fuck, man; that went from zero-to-sixty real fast… That’s not at all how I ever thought my first time was gonna go.’”


25. My ex-GF shit the bed after anal sex, her parents knocked on the door, I looked her dad in the eye and said I had explosive diarrhea.

“-Background- When I was 17 the ex gf and I were on a skiing trip with her family. We left the slope and went back to the lodge to get a little sexy time going. Well she was in a very kinky mood and wanted me to try giving her anal, so being adventurous I figured why not let’s give it a go.

Neither of us knew what to expect, we both started really getting into it and she started to orgasm. Almost immediately we hear her parents trying to open the door. They can’t because it’s locked from the inside – but we were both scared and in the ex’s dazed state she moves forward and ends up pooping all over the bed sheets.

She runs to the bathroom and locks the door leaving me there with soiled, bloody sheets…. Her dad… was a big guy his nickname was ‘tree stump.’ Well, tree stump is banging on the door yelling for us to open it.

Only one thing comes to mind: I sit (with my boxers on) in the poop sheets and get my butt nice and dirty then run over to the door and open it.

He is fucking furious..


Tree stump: why is the door locked, where is (girl’s name), what the fuck were you doing with her you little shit?

Me: I wasn’t feeling good so we came back here so I could lay down.

Her mother: oh my god there’s poo all over the sheets!!!

Tree stump: What the fuck ??

Me: (keeping a straight face) I was laying down and starting to feel better when all of a sudden I had explosive diarrhea. silence

They both just look at me…

(in my head I’m thinking, omg.. If I don’t keep a straight face, I am going to be murdered…)

Her mom: are you feeling better now?

Me: I’m super embarrassed :(.

Her mom: oh honey, don’t be it’s ok.

Tree stump: why is (girl’s name) in the bathroom?

Me: she ran into the bathroom and threw up after it all happened.. I was just trying to figure out how to clean when you guys knocked on the door.

Most awkward sex/conversation I’ve ever had…. Sadly not the most awkward situation I’ve ever been in.

TL;DR: my ex gf shit the bed after anal sex, her parents knocking on the door, I looked her dad in the eye and said I had explosive diarrhea.”


26. The girl had an orgasm, lost control of herself, and urinated all over me and my bed.

“During some particularly ‘active’ sex, the girl had an orgasm, lost control of herself, and urinated all over me and my bed. She couldn’t think or talk straight for a few minutes.

No, this did not deter me in the slightest. Finished my business after that.

We’re still going out.”


27. I looked in the mirror…looked like I’d taken a shotgun blast to the face.

“Fooling around with a girl who was a virgin…one thing led to another and we’re at oral sex…she’s then sitting on my face and really getting off…very wet…then suddenly realize the metallic taste in my mouth…

Virgin girl had her period whilst riding my face.

She freaked out a bit, told me to get in the shower but ‘Don’t look in the mirror!’ … of course I looked in the mirror… looked like I’d taken a shotgun blast to the face.

tl;dr Period blood, all over my face.”


28. My parents both walk into the kitchen to surprise-visit me. Screams ensued.

“Most awkward for me was with my then new, and very frisky, ex-girlfriend. At the time my parents weren’t one to knock a lot when they came round.

So here we are, GF and I, making lunch in the kitchen when we start getting a little touchy feely. Things progress and we’re stark fucking naked going at it like it’s the end of the world in the kitchen up against the fridge.

Anyway mid-thrust my parents both walk into the kitchen to surprise-visit me. Screams ensued. We darted to the room to cover ourselves. We come out of the room and exchange introductions as family to partner goes for a first time greeting.

Most awkward afternoon of my life.”


29. I’m dripping wet, vomiting semen and farting, while my poor boyfriend is watching from the shower.

“Age 17. Boyfriend had been begging me to give him a BJ and swallow. We were in the shower and I went down on him, he came, I swallowed, felt sick immediately, jumped out of the shower and vomited into the toilet (which was in the same room as the shower). What makes it worse is the force from my vomit made me fart as well. So I’m dripping wet, vomiting semen and farting, while my poor boyfriend is watching from the shower. There were no words.”


30. I landed on my back and fractured a rib.

“My girlfriend my sophomore year in college and I were messing around on my bed. I tried to do some champ move of lifting her legs straight up and pulling her pants off in one move. She wasn’t that flexible, so as her pants flew off her legs came down hard into my chest knocking me backwards off my bed. I landed on my back on a dumbbell I had on the floor and fractured a rib.”


31. I tea-bagged a pit bull.

“I was in bed with this girl, having a great time. The bedroom door nudges open and I’m thinking ‘WTF is that?’ So I’m looking around, no sign of her kids, but then there’s this THUD and her fucking PIT BULL jumps up on the bed.

She giggles and says he gets worried when she moans, he thinks she’s in pain and comes to protect her.

My balls are swinging in the wind and there is a fucking PIT BULL behind me!

I figure the dog will just lie down, or go away (please go away) so we get back to it – and then I feel the one sensation that is guaranteed to put your testicles in your armpits. The dog’s wet nose sniffs my nutsack. I nearly screamed.

‘What’s wrong?’ she says.

‘Your dog is sniffing my balls,’ I reply in a shocked whisper. She starts laughing so hard that we are bouncing around a bit and the dog starts getting excited and jumping around the bed, barking.

Now when my wife suggests doggy-style I have a panic attack.

TL:DR: I tea-bagged a pit bull.”


32. I peed all over my boyfriend’s face.

“I was pretty sexually inexperienced when I started dating my boyfriend at age twenty. It took him FOREVER to convince me to let him go down on me. Serious reservations were had, but finally I let him under the conditions that we leave the lights off and he stay under the blanket. He agreed pretty readily, I guess since he’d been trying to convince me for so long.

Anyway, I don’t really know what happened. I was enjoying it — really enjoying it. Far beyond any self-gratification I’d ever given myself. When he stopped before I climaxed, I was pretty pissed. He lifted his head up and pulled back the blanket and said, ‘I’m going to stop now.’

Asshole. After all that wheedling to get me to go through with it? ‘Why?’

He was already getting out of the bed. ‘You just peed.’



33. It was like I pulled a plug out of a pressurized whoopie cushion.

“My girlfriend and I were going at it. It was probably the third time for both of us, and I feel the condom come off inside of her. (Goddamn lube on the inside. That and she’s tighter than my wallet.) I pull out, and go to retrieve the condom, which was hanging out of her. It was like I pulled a plug out of a pressurized whoopie cushion. The queef that came forth from that eldritch axe wound sounded like she had cleaned out a motherfucking Mexican buffet and then ate an entire wicker swing set. (And I know she didn’t fart because it was doggy and I had a full view of the plumbing. I saw her labia flap.)

I laughed until I cried.

We’re getting married in September.”


34. I sneezed suddenly all into her vagina.

“Was going down on a lady when suddenly I had to sneeze. It was one of those no warning deals. I sneezed suddenly all into her vagina. Then, to make matters worse, it scared her so she slammed her legs shut. So there I am with the snot and her juices slithering around the small space that I was destined to suffocate in.

All the while she was screaming out of surprise then pleasure.

We spent the rest of the night laughing and crying.”


35. Her dad proceeded to RE-LICK his thumb and continue to rub ‘the crusties’ away.

“In the early 2000s I lived in Chicago w/ a fling of a girlfriend that just happened to have a thing for facials… So, one night I finished her off, she went to the bathroom to ‘clean up’ and then came to bed. The next morning we wake up and get surprised that her Father made breakfast. As I sat down, because she offered to bring me a plate, she went up, stood next to her Father, and started shoveling the food. Her Father, w/out pausing, glanced at her, licked his thumb and said, ‘Hun… You have something on your face.’ He then proceeded to wipe his thumb on something on her face. Two and two didn’t click at this point and being a Daddy’s girl she didn’t flinch away. He proceeded to RE-LICK his thumb and continue to rub ‘the crusties’ away. Her jaw dropped, she went silent, and then ran off down the hall to the bathroom.

I couldn’t stop laughing. I seriously almost pissed myself.”

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