19 Of The Most Cringeworthy One Night Stand Stories You’ll Ever Read

SteveHolt9 years ago

One night stands can be great. You get all the reward with none of the relationship risk. Usually, you just have to dish out one of your old t-shirts that probably hasn’t been washed in weeks afterwards and both of you can go on your merry way, never to speak again. It’s a win-win for everyone involved.

It isn’t always that perfect, though. Sometimes you have to deal with the crazies and some pretty awkward memories. A thread on the internet forum Reddit asked people from across the world to share their most hilarious and awkward one night stand experiences. A few of the answers are hysterical, while others are downright despicable.

I was in a bar, having a beer and this girl starts talking to me. She seems OK, but the bar is dark. Hard to tell. She asks me if I want to go out to her truck and smoke a joint. I say “yes.”
When we wander out of the bar, the bright lights outside illuminate her face in a disturbing way. I ignore what I am seeing. She says, “so where is your car?”
I say, “I thought we were going to your truck?” She says, “No, we are going to your car.”
OK. I can deal with this.
We get to my car, and she says “Where is the joint?” I say, “I thought you had a joint.” She says, “No. Take me home.”
OK. I can deal with this.
So, I start driving her home. As I am driving, she starts rambling, “you can fuck me. you can screw me. you can do anything you want to me.”
OK. Maybe I can deal with this.
As we approach her apartment she says “I sure hope my boyfriend isn’t home.”
Oh, fuck. Can I deal with this?
She points to a convenience store and says “Pull in there. And go buy me a 12 pack of beer.” I say, “I’m not buying you a 12 pack.” So, she gets out of the car to buy beer.
I definitely cannot deal with this, slam the car into reverse, and race off into the night.
I didn’t go back to that bar for a year.
Creepy girl.

Red flag number one was her driving a truck.

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 Gwyneth Paltrow’s head a pink dildo with my name carved into the side, won’t be dating on Tinder for a bit.

I suggest changing your name, number, and moving to the other side of the country.

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…

Sometimes when you’re pounding pussy, you start to purr. Nothing odd about that.

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.”

Think the guilt set it a little too late.

I once was with a girl that wanted me to piss inside her butt.
I noped the fuck out of that.

Peeing in her butt is definitely a TFM.

What was going to be a one night stand ending up being me comforting the guy while he cried about missing his ex. Awkwardly held him in my chest while he told me about how his high school sweetheart left him. Yes that sucks, but it wasn’t exactly the right moment for a heart to heart.

That’s just depressing.

Well one night, I meet this girl and things are progress.. 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.

That response by you was a power move.

Blew a guy after a big breakfast date. He was pretty big; I gagged and eventually threw up all over his cock.
I’m mortified, but he takes it like a champ. He grabbed a towl, cleaned himself off and kissed me, wanting more sex.

I’m noping the fuck outta there.

I was out at the bar and I was on my period. So, I had no intentions of hooking up with anyone. But, I met a cute guy, who wouldn’t take no for an answer, even though I told him straight up that he didn’t want to do this, that I was bleeding. But, he insisted, so we went back to his house. We had sex, then he gets up and goes to the bathroom, and when he comes back he’s angry because of the blood on him. So, he starts yelling at me because he thought that I was only using my period as an excuse. So, he kicks me out of his place, cursing me out the entire way out. So then, I’m sitting in my car, and of course I left my $50 bra in his bedroom. Fuck that, that’s $50! I knock on his door, he doesn’t answer, and I leave. Over the next 2 months everytime I see this guy at the bar I’m like hey, I want my bra back. I even resorted to sending my friends over to tell him that I wanted my bra back.
Finally, one night I walk into the bar and the bartender says “I’ve got something for you” and hands me my nice $50 bra.

That’s a lot of effort. Shoulda just freed the nipple.

One time a guy asked me mid-sex if I was on birth control. I said I was. He said “so there’s 1% chance I can get you pregnant.” I fucking ignored him and a few minutes later says “I can’t wait for you to have my babies.” I told him to stop saying that. He says “you better be staying over tonight. You’re my future wife.” I noped the fuck out of there and ignored all 20 of his messages and calls since then.

Usually it’s the girls who wrap their legs around you like a Anaconda and scream “have my babies!”

Met a guy at a bar, ended up back at my place drunkenly blowing him. I asked if he had a condom, he tried to argue that since I put his dick in my mouth I should let him fuck me unprotected too. His cock fell from my mouth with an audible “pop” noise and I just kind of sat there with a confused look on my face. Who argues while getting their cock sucked?

Guy kinda has a point, though.

I matched with this girl from tinder and we hit it off really well. The conversation quickly turned to sex, and she said she really wanted to have sex with me since I was bragging about how good I was (which is most likely a lie). Anyway, right before she comes over, she warns me. “I’m a squirter.” My reaction was like, “this is awesome, I’ve never banged a squirter.” I told her I was into it and she was relieved. Fast forward to her getting there. She walks in, I immediately take her to the bedroom. We start having sex, using the last condom I had. Well it broke, and she looked at me and asked me if I was clean, to which I responded “I think so.” She said, good enough for me. This is important because having sex without a condom obviously feels way better, and it makes me nut way faster. So, we start banging doggy style and I pull out to give myself a break. To keep her entertained I start fingering her from behind. With my palm facing up. Idk if you guys have ever banged a squirter, but their orgasms are intense, and water starts gushing everywhere and it puts a tight squeeze on their insides. Well she starts squirting while I’m fingering her and everything gets real tight. I take one moment to look up at her head. Then it happens. I feel something in my palm. I look down to what appears to be either a wet pouch of chew or a small piece of shit. Well she didn’t chew. She shit, right into my palm. My palm was in a cradle position, so it was just sitting there. My initial thought was… “What is that” And once I realized, I threw it into my blanket and wrapped it up. I immediatly stopped what i was doing and laid next to her. I told her I was done, and we’d have to do it again some other time. We walked out to our car, said goodbye, and that was it. She must have known. Walked inside, and threw my blanket in the dumpster.
And that, ladies and gentleman, is how I had monkey sex.

She could have given you a fantastic Cleveland steamer.

I hooked up with this girl one night while I was tripping on mushrooms, it was quite sentimental until she started bawling her eyes out for ‘no reason.’
I find out the next day from her friend that she cheated on her boyfriend.

I hate when girls cry.

Hooked up with my sisters unattractive friend while EXTREMELY drunk last Halloween. She was 29, and I was 19. At one point I say “I want to put it in your ass” (don’t judge) and she says “only if you can make me cum.” I pause and say “Ehh, I’m not THAT into this!” She was not happy. I then had to spend all last night around her and her new boyfriend for my sis’s birthday. Not great.

“Ehh, I’m not that into this.” TFM.

Thought a guy said ‘piss on me’… so I urinated all over his chest and bed linen…. Turns out he said ‘kiss me’… Not my classiest moment

You’re an animal.

Last night. He didn’t tell me he was a virgin until the pants were already off, and apparently I was literally only the second girl he’d ever kissed. Not bad though, except for him incessantly asking how he was doing and cracking self-deprecating jokes. Oh, plus for the first time ever I experienced a condom getting “lost” inside. Nothing like having to root around near your cervix while simultaneously reassuring a random dude that it’s fine, his dick isn’t weird, yes you’re having a good time, etc.

Ahh, the ol’ “lost condom” trick when you didn’t use one in the first place.

Almost immediately after hooking up in the backseat of my car, she reaches into her purse, pulls out a pin with a couple of tiny feet on them, and says:
“Isn’t this cute? This is what a baby’s feet looks like when they’re aborted. There’s two things in this world I despise: divorce and abortion.”
Why I continued seeing her for another two months is beyond me.

100% chance she’s carrying your baby.

I brought home a guy, Mick was his name.
I was drunk.
I’d not had sex for awhile, so we’d normal sex, bit of fun, I said will we have anal sex……
He freaked out, got up and dressed, ran out the door and left his shoes in my house.

Mick is not a supporter of #ButtStuff2016

When I was 20 I worked with this girl who had a thing for me. She had only worked with me for about a week until we hooked up. The morning after I woke up in her bed the next morning. Got dressed and noticed she was staying in bed. I asked her if she was coming in to work, she said no. She was going to quit after the first day but wanted to sleep with me before she did. She said thanks and to tell our boss she quit.

Now that’s how you go out with a bang.

To read more hilarious stories like these, click here.

[via Reddit]