Love & Sex

16 Hilarious Hookup Stories From People We Met In Bars

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The funniest anecdotes from Hooksexup's popular Talking to Strangers column.

Colleen, 30, New York, NY

Has anyone ever offended you in the bedroom?
One time I was hooking up with this guy, and I'd been hooking up with him for a while, but he was never… I don't know, we just always had the same exact routine. And then one day he decided to do three things at one time, basically, out of nowhere. But as he went to do it, he went, "Trifecta!" He sounded like Napoleon Dynamite. I couldn't believe it. I was like, "What the hell was that?" It was such a turnoff, and I was like, "Stop touching me." He finally did something cool, and he fuckin' said "Trifecta!" before it.

Anthony, 29, Berkeley, CA

What's the craziest date you've been on?
One time, I met this guy online, and we had planned to meet up. So, he came over to my house, and I have a cat. And all of a sudden he got really stuffed up, and it turned out he was really allergic, and his eyes were watering and his tongue was itching. So I gave him an antihistamine, and we're talking, and all of a sudden, he spits something into his mouth — and it was his front tooth. His tooth just fell out, while he's was having this allergic attack. I don't know if it was related. It was the first time I'd ever met the guy. I felt so bad. It was so awkward.

Did he go to the hospital?
No, but we kind of just parted ways and never called each other again. You know, when teeth start falling out…

…that's your deal-breaker.

Austin, 23, Portland, OR

Do you have any crazy hookup stories?
One time, I was at a party at my friend D.'s house. I met this hot girl, and we had this crazy, instant chemistry, so we went to D.'s room to have sex. So we're doing it, and halfway through, it started to feel really good — like, too good. It didn't occur to me right away, but the condom came off. So I stopped, and when I pulled out, the condom had just disappeared. Vanished. We tore the place apart looking, but — nothing. We were in my friend's bedroom, so I didn't want to just leave it there for him to come across later.

What did you do?
Okay, so, my friend D. happened to have this pair of forceps that he got at The Salvation Army.

Because that's the best place to get semi-used gynecological equipment…
In Portland, anyway. So, D. used to go out with the girl I was having sex with, who was still a good friend of his. So she asked D. to look around inside her for the condom, using the forceps.

Why weren't you recruited for the job, instead of D.?
I'd never used forceps before, and I didn't want to, you know, do any damage. D. used to be an EMT.

So he had basic training in emergency condom removal?
More than I did!

What happened next?
I went down in the courtyard of the house to chill out. After a few minutes, D. came out on the balcony and waved the forceps, which were holding the condom. He yelled out, "I found it!"

In other words, a latter-day version of the balcony scene from Romeo & Juliet.
Pretty much.

Scott, 26, Seattle, WA

How did you meet your girlfriend?
We met at a Christmas party at a BDSM club owned by my aunt. 

Your aunt? You've got to be making that up.
I'm not that imaginative. My aunt really does have a BDSM club. Some people get an adrenaline rush from the pain in BDSM scenes, but it's not even a sexual thing, necessarily. The whole thing is very misunderstood. I was flogged once, at my aunt's club. It wasn't sexual at all, but I almost went into shock. I kept calling out "Judas Priest!" and "Mother Teresa!" I didn't want to curse in front of my family.

Jerome, 27, New York, NY

What's the boldest thing you've done to get a woman's attention?
I spilled a cherry Slurpee on a girl's white sneakersI did it on purpose. We were in the South Berry station on Staten Island, right outside the station. When I came in, she was looking and our eyes connected. So I said hello first, and when I said hello, I spilled the slushie and it got on her laces. I'm always playing around. I had some money on me, and I already knew that I was going to give her eighty dollars for her sneakers.

That's an expensive way to pick up ladies, isn't it?
I knew that if I did the whole thing right, and she didn't have a man, she'd give me her number. So, she starts flippin'. I'm like, "Where's your man at? I can't go hooking you up with more sneakers because I don't have any money on me!" and she's like, "I don't have a man! Don't be asking me all these personal questions! You just spilled on my Ups!" I was like, "Well, look, here's eighty dollars right here. Boom!" and she snatched it from me real quick. I start kickin' it to her, we started talking about clubs that we had been to, and I was like, "Yo, look, I'm a cool cat. If you ain't doing nothing, let's link up and go shopping on Saturday, and let's go hit the club." I actually didn't tell her that I did it on purpose until the night that I called her. She was like, "You know what? Your approach was kind of like you did it on purpose, because I saw your hand when you poured it, and I was so mad. I didn't know if you were some dude who had lost his mind for a split second or what." I think it lasted with her for about eight months.

J.J., 26, Portland, OR

Did you go out with any of the strippers you worked with?
No, unfortunately. But I did hook up with a really cute pedi-cab driver I met through the restaurant. See, we would tip the pedi-cab drivers who brought tourists to the place. So, this one girl driver came by all the time when I was working at the door, and sometimes we talked for a while. She kept saying she'd be glad to give me a free ride home from work, any time. I had no clue that she was flirting with me — probably as a result of being in a relationship for so long, I'm sort of clueless when it comes to picking up on cues. 

If that's the case, how did you ever manage to hook up with Pedi-Cab Girl?
One night, I was getting off work when she came by. She totally took charge — she said, "Want to come home with me?" I thought, why not? So, we went back to "her place," which turned out to be the garage of the pedi-cab company. We had a bunch of drinks, and talked, and then we had sex. In the morning, I woke up naked on this mattress on the floor of a pedi-cab garage. At first, I had no idea where I was. It was pretty surreal. Then the pedi-cab drivers started to come in to start their daily shift. Nobody seemed to notice, or care, that there was a naked guy on a mattress in the corner.

Sean, 32, San Francisco, CA

What's the weirdest sex thing your innocent eyes have seen?
It was more like a vocal thing. It was somebody who was intensely into dirty talking. She was really demanding a lot of complicated hypothetical scenarios from me. It wasn't even sex. It was like a complicated masturbation scenario, plus some oral sex, but also telling a story.

What was the story? Give me the dirt.
So the girl was pleasuring herself. It was all masturbation, and my job was to tell an elaborate story, talk really dirty, but also basically, um, have my dick on her face. That was the whole thing. That was what I was supposed to do. 

Did you add scenic details? Did you create a doctor's office or an island?
No, it was basically just right there. Like you and me in the bed having sex, and this is how great it would be if we were actually having sex, but we weren't having sex. It was weird. And the response was that her voice got lower and lower. The more turned on she got, the lower her voice got. To the point where she was saying "Yes" in a way that just made me think "No!" And I was definitely getting freaked out, but I thought I couldn't stop talking, so was just like a weird stream of consciousness thing. I felt like I was being mentally held hostage.

Could she have been a man?
I'm pretty sure that wasn't the case.

But you were thinking it.
You never know in San Francisco.

Abbi, 23, Paris, France

Do you have any crazy hook-up stories?
I have one from Portugal. I went out with my little brother and his friends, and I met this Australian guy, and I was really drunk and gave him my number. He texted me the next day and we got absolutely shitfaced. He was very good-looking, but he was brain-dead. At four in the morning, he was like, "Do you want to come back to my house?" and I said "No, you can come back to my house." But my bedroom was literally across the hall from my parents' bedroom. So we did the deed, and it was horrible. Both of us were too drunk to remember how to have sex. Neither of us knew what we were doing and we were absolutely hammered, and at one point he turns to me and says, "I love fake tits. I'm so glad you have them because I love them."

Oh, wow.
I didn't know whether to be extremely offended or extremely complimented. But I told him, "Seriously, you have to leave." So it's six in the morning and I put this guy in a taxi and I think, "I never want to see you again." And he says, "We should go out for drinks tomorrow," and I said, "No! I just remembered, I actually have to go home tomorrow morning. I have a flight really early."

But you didn't.
To cut a long story short, the next night I went to a bar with my dad's fiance, and we were getting absolutely shitfaced. Eventually we were waiting at a taxi run. I look down the taxi run, and who the fuck is sitting there? He's kind of looking up at me, and I'm looking back going, "Oh fuck!" trying to hide behind my dad's fiance. I told her, "That's the guy from last night!" And she's so fucking Irish, she turned to him and asked if he wanted to share a taxi. I was like, "Get in the fucking taxi and shut up!" and he looked at me and said, "Oh my God, babe, I thought you were going home!" and I said, "I am going home! Goodbye!" I was trying to close the door and he was trying to get in the taxi, and I shut the door on his arm. The last thing I saw was him holding his probably broken arm as we were driving away.

Chris, 41, Los Angeles, CA

What's the craziest thing you've done to get action?
Once I dressed up like a walrus. She was into it.

Isn't that called "furry sex" or something?
No, it was more cerebral: she liked the Beatles and I am the walrus.

Did you keep it on during the sex?
Yes, I kept it on.

Did you fall asleep in it?
No. It was very hot.

Patrick, 45, Brooklyn, NY

When's the last time you got laid? 
Oh, Jesus Christ. You guys aren't fucking around. Two nights ago? Honestly, it wasn't all that great. It wasn't all that connected, we were doing it just for the sake of doing it. You know, better than jerking off. 

Please grade your orgasm. Like, a B? 
No, it was like a D. 

What's the difference between fucking a younger girl and an older woman? 
There's not really a difference at all. All that matters to me is an emotional connection. And in the absence of that, it's just like, well… let's just do it anyway. 

The D-grade orgasm — was she younger or older? 
They were younger. 

They? You had a threesome and it was a D?
[laughs] Yeah. They were wasted. 

When did threesomes get boring? 
Wait, no, hold on a second. That's not what I'm saying. This particular one was no good.

Audra, 35, Montreal, QC

Have you ever offended anyone in a similar way? 
I've definitely said the wrong name. I think that's the worst that I've done. 

How did you recover from that?
Um… I married that guy, mostly to reassure him. But it didn't go very well, as a marriage. I don't recommend that approach.

Scott, 36, Los Angeles, CA

What do you do for a living?
I'm a personal trainer and yoga instructor.

What's your craziest sexual experience? 
I had sex with a British woman in a taxicab in India. Doesn't get more yogic than that.

Nice. How did that come about? 
Well, it was in Goa — the Cabo of India. We were going to go make out at the beach after a club, but I guess we couldn't really wait.

Did the cab driver get mad? 
I do remember him adjusting his mirror a little bit to get a better look.

And did you like that? 
I was not concerned with the driver at that moment.

Michael, "105," San Francisco, CA

What did you do on the railroad?
I was a dining-car steward. Oakland to Chicago, for four years.

Did you have sex on the train?
Absolutely. As often as I could. Whenever I saw a young lady in the dining car, and she kind of glanced at me, and I kind of glanced at her, we'd step back into the Pullmans. And I had a room back there, because I was an important person, you see. So I could entertain after hours.

So what would you say to a lady on a dining car to get her to accompany you to your lair?
"How are you, my dear? You look lovely this morning. Did you sleep well?" I only dealt with first-class, only the Pullman passengers. Those are the cars with the sleeping rooms — little hotels on wheels. If you were in coach, you'd be back with the hoi polloi, babies throwing up and all that. I never trucked with them. So if a young lady comes into the Pullman, you seat her — "How are you my dear?" Yadda, yadda, yadda. And then when she comes in for dinner, you say, "I'd like to buy you a glass of wine. Come back after we close." They wouldn't always say yes, but more often than not, they did.

Did you ever get caught?

Amazing. Were the other employees doing it as well?
Well, there's only one steward on a train. I didn't like competition. I left those other guys on the ground.

Bilal, 29, Los Angeles, CA

Do you have any good hook-up stories?
Yes, I do. This one time I hooked up with a girl I used to work with, and we were at her apartment, and we were both stone-drunk — like Mickey Rourke in Sin City stone-drunk, and we're fucking, and I let loose the biggest fart — 'cause, you know, she's on top of me, and she's riding me so she's pushing down on my stomach. It sounded like Wynton Marsalis just walked into the room, let loose a note on his trumpet, and then walked out. But the thing is, she was so drunk that she either played it off perfectly or she didn't even notice.

You know this is being published, right?
I don't give a shit! I've told that story to my mother.

Daniel, 24, Brooklyn, NY

What about hookups? Any crazy stories there?
Definitely. This one girl was a hostess at the restaurant I worked at and we exchanged numbers and hung out later that night. I told her I had to go back to my place and feed my fish — which, weirdly, wasn't a line — and we started making out and went to a party on the other end of town. We were outside smoking cigarettes with a bunch of her friends and then she kind of just fell over and knocked her dome on the sidewalk and had a seizure. I was like, "Shit, how am I going to get home?"

That was your first thought? Was she okay?
Well, the ambulance wouldn't let me on, because I'd had a few drinks. I visited her in the hospital the next day though. We hooked up a few times after that, but she started doing things that were really weird. Then I found out from one of her ex-boyfriends that she'd been stalking him and that he actually had a restraining order against her. So, I canceled that. She's actually started sending me nudie pictures of herself recently, even though we haven't talked in a year and a half.

What are the pictures like?
Oh, they're incredible. They're videos with all kinds of angles and stuff. I don't know how she does it one-handed.

Kerri, 34, Los Angeles, CA

What was the hottest hookup you've ever had?
Mick Jagger.

Really? What was it like?

Interviews by Rachel Barth, Lina Canney, Alyssa Carroll, Daniela Cervetti, Amanda Cotylo, Elyssa Goodman, Marguerite Kennedy, Libby Rumelt, Laurenne Sala, Sarah Trowbridge, Jana Van Geest, and Alia Volz.

Can't get enough Talking to Strangers? Peruse the full archive here.

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