These people have openly shared their most awkward one night stand experience with us, and it is the funniest thing you’ll read all day.
1. Her parent were it.
Went on a date, had a fun time, had sex in a public park in the city, went back to her’s, had sex again, asked where the bathroom was, went to the bathroom, accidentally went into the wrong room, found her parents sex toy stash in the corner of the room, went home, got up in the morning, told a mate at work what happened, he told another guy at work, turns out it was his sister I had sex with and his parents stuff I had caught, he wasn’t happy, he approached me and threatened me, I told my boss what he did, he got fired, went home from work, found a box at my doorstep, took it inside and opened it, there’s a letter (cool), open the letter, it says “we’re watching you” in capital letters, looked inside the box, found a pink dildo with my name carved into the side, won’t be dating on Tinder for a bit.
2. Had no clue of what happened but the breakfast…
Went out boozing big style, my friends said I was barely standing by 11pm so they told me to get a taxi home (taxi rank was directly outside the club).
Woke up next morning in a strange bed with shitloads of dollies and stuffed animals on a shelf…uh….ok.
Managed to put my trousers and jumper back on when a woman around a decade older than me came into the room carrying a fried egg sandwich, she smiled at me and said “you need to eat this then leave. Quietly”, then about-faced and left the room.
I quickly scoff the sarnie in a vague attempt the quieten the monstrous hangover that was starting to build as the last of the booze wore off, went into the hallway and she was standing at the front door holding my coat smiling slightly. I try to ask her what happened last night but she simply shocks her head and motioned to the door.
As I get outside I realize this is a really really posh estate.
I’ve not got a damn clue what happened but it left me really weirded out for a long time….
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3. His getting off made the whole house vibrate.
Took home this huuuuge muscly guy, super alpha. He was picking me up and kinda throwing me around the place, and I was thinking, well why not! It’s fun to feel a bit submissive sometimes. So it was fun if a bit cheesy-try-hard.
But THEN… He starts purring. Actually purring like a large cat. It started while he was working up to cumming and when he came it was like a really loud steam engine. I couldn’t cum because it made me laugh SO much.
My flatmate heard it from her room underneath mine as well. I feel like it must have made the whole house vibrate…
4. Hooked up with a married dickhead
Hooked up with a guy, he hadn’t been “finished” for more than two seconds when he practically yelled, “I’m married with 3 kids.”
5. Karma got to me.
20 years old, hanging with this girl I knew through friends in her dorm room. I knew she was into me and she was cute but I wasn’t really into her. Obviously, my 20-year-old horny self-decides ahh fuck it why not have a good time. We are in the middle of clothes being ripped off and parts being touched when I realize how bad of an idea this is. I’m typically a good guy and don’t want her to get the wrong idea. But of course, I’m 20 and can’t just say “hey, lets take this slow, or sorry I’m just not really feeling it.” So… I tell her I have to run to the bathroom real quick. While in the bathroom I send a text to my roommate telling him I need him to call me in 15 minutes and tell me there is an emergency back at the apartment. I get back, some light petting and smooches and then like clockwork, roommate calls. I pick up the phone, and proceed to try my best shot at an Oscar, “What do you mean our apartment got broken into?” “Well, what the fuck did they take?” “Everything?” “Shit, check my desk, is my laptop gone?” “Fuck, alright call the cops, I’ll be home soon.” I turn back to the young lady and apologize that the night has to be cut short, but I promise I’ll text her when I get home(Why do we always say shit like that….) I get home and thank my buddy for helping me out of a jam and all seems good. Until a week later when our other roommate leaves the door unlocked and we are robbed and the only thing stolen is my fucking laptop…Karma…
6. She stripped me naked and threw me out. WTF!
This wasn’t awkward or hilarious more depressing. After going to a girls place we’re in the middle of playing pelvic peknuckle and suddenly she has her climax. Before I could bask in my achievement she shoves me off her and starts throwing my clothes at me. Apparently, once she had finished she wanted me gone…so that was a really shitty moment. So now I really don’t do one night stands. That moment kinda soured the entire idea of those encounters.
7. The weirdest one night stand
I once was with a girl that wanted me to piss inside her butt.
I noped the fuck out of that.
8. I wanted to send her out of her own house.
I was about 23.. after my first divorce I kind of just stuck to hanging out in bars.. didn’t want to be around the house for a while blah blah…
Well one night, I meet this girl and things are progressing.. we end up leaving the bar.
Well, I wake up the next morning, still drunk. And I can feel someone laying on my arm (quite cloudy at this point) and without really moving a whole lot, or opening my eyes I say “Hey um.. don’t make this awkward or anything, but I think you should just go”
You know, fresh out of a failed relationship, I wasn’t looking for anything and tripped over a one night stand.
She replies, “you stupid son of a bitch this is my house!”
I opened my eyes, I know I’m in trouble so I just say the first thing that pops into my head, “I though I said don’t make this awkward?”
Needless to say, I waited outside for my cab that toasty July Arizona morning.
9. One night stand with my professor
When I was in college (I was like 20/21) there was this guy named Josh who I used to run into all the time on campus since we were sort of in the same-ish circle of people. He would always open doors for me and say hi but I never really paid too much attention to him other than thinking he was sort of older but kinda cute in a John Cusack kind of way. I worked at the local coffee shop and I started to notice that he was showing up a lot when I was working and ended up starting to go to outings in my friend circle. I figured he was just an older student or whatever. I found out he had been asking people I knew about me and one day he messaged me on Myspace asking me if I’d like to come over and watch movies. So, I got all dressed up cute and went over to his house and we watched The Princess Bride and drank beers. After the movie was over we started making out and ended up going to his room but the lights were out and it was super dark. He had the tiniest penis I’ve ever encountered and was the first dude to ever go down on me so naturally I was all around freaked out. We had really terrible, clumsy, dick falling out constantly sex. After it was over and I’m laying there in my underwear he turns the light on and THERE’S ALL THIS BABY STUFF IN HIS ROOM. I’m like “wtf dude?” and it turns out that he was actually a dad of a one-year-older in the middle of a divorce living with his parents AND was a professor at my school! He failed to mention anything to me. I was so embarrassed I told him I was tired and went home and never talked to him again.
Thankfully I ended up transferring to an East Coast school a few weeks later and didn’t have to run into him again. Thankfully that taught me a valuable lesson to be more investigative.
10. My new year eve was ruined by this 5secs guy.
About 4am on new years day I decided to hook up with a guy who I met over tinder. he’d been sending me messages and really talking up his prowess. you know the whole “yeah baby I’m gonna fuck you for hours ;)”. plus his dick pics looked promising. on the way to his place I decided to buy an ice cream sandwich. I only took one bite and left of it in my car. keep in mind this is NYE in Australia so it was about 25 degrees outside and even warmer in my car.
so I get to his place, start pashing for about 30 secs before he whips his dick out. it feels amazing! he thrusts once, twice and then suddenly screams ‘OH NO!! OH NO!!’ and comes. I ask if he wants to try again. he says yes and then starts violently jackhammering himself for about a minute. to this day I’ve never seen anyone treat a dick so roughly. I almost felt sorry for it. I just sat there silently watching with poker face. after the minute passed he says ‘no it’s not going to happen. you can go.’ he starts pushing me out the door before I even have time to put my dress on. so I leave and walk back to my car wondering what the fuck just happened. the whole thing was so quick that by the time I got back to my car my ice cream sandwich as still frozen. so I spent New Years morning watching the sunrise and eating my ice cream sandwich and that is my most awkward one night stand ever.
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11. Had the best night, but we couldn’t communicate
Slept with a girl from Russia in Orlando Florida that did not speak English that night after drinking the language barrier was erotic and somewhat understandable but that morning it was confusing and just awkward. (She slept in my bed until noon with no polite way of saying I have to go you need to leave)
12. This last one is really long but worth the read!
Back when I was in law 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 “law school hot” — late 20s (and just starting to show it), slightly pudgy, finally trying harder to dress professionally than to dress sexy, generally attractive, but didn’t really stand out in a crowd. Her biggest asset — literally — was her awesome rack. To quote Fight Club, they hung enormous, the way 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 is a huge deal. (The stress during the initial year in law 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 point, so when I saw her walk through the door, I waved her over and she joined our group of about ten or so.
At some point — prompted in part, I’m sure, by large quantities of booze — we, of course, started talking about sex, and because one of the guys with us was gay, the topic of anal sex came up. After a bit, M admitted that she had never tried anal. I was drunk and-and feeling 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 door 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 stay, so I offered to buy her next drink if she’d stick around.
When I came back with her drink — something with tequila, I believe — she turned to me and said, “I shouldn’t be eating 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, ending up naked and horizontal in her bed.
Emboldened by earlier conversation, M’s apparent enthusiasm, and a large dose of alcohol, I eventually suggested that we try anal, and M agreed. After some shuffling, we ended up with her on top so that she could control the depth and speed, and for a few minutes, I was happily 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 pain and fear. Assuming 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 tipped 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 begged 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 act, and the sheer ridiculousness of it all meant we didn’t make much progress. In a moment of inebriated genius, I hoisted her up by the hips and suggested she walk on her hands.
It turns out that wheelbarrowing a crying drunk girl across her apartment with your dick stuck in her ass isn’t particularly 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 blasted 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 smell — like wet garbage in the hot sun — hit me. I was painted from the waist down with her special brand of brownie batter. I was in shock. I just stood there, dumbfounded, staring at this poor girl, suffering the world’s worst case of mudbutt, crying 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 sound. 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, someone snapping gum through their teeth, and the glug of a water cooler. That sound 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 distant drone, almost outside my notice, 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 mean 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 saw me, but I didn’t care. I ran the 100 yards to my apartment door, past everyone, and I threw myself in the shower, and I cried.