6 Hilarious Stories Of Having Sex On Halloween That Might Make You Rethink Your Costume

by Alexia LaFata
Isaiah & Taylor Photography/Stocksy

Halloween is a time for dressing up in a crazy costume, watching scary movies, and eating copious amounts of candy. If you're an adult, it's also a time to go to a party, hook up with someone, and leave red and blue streaks of makeup from your Pennywise clown costume all over your hookup buddy's mouth, neck, and bed. If your costume has ever low-key cockblocked you like this, don't worry, you're not the only with an embarrassing sex story from Halloween.

There's no better night than Halloween to boldly approach someone for a hookup. Wearing a costume, whether it's sexy, funny, or plain old scary, allows you to channel someone else entirely for a night, which means you get to leave all the inhibitions you'd have as "yourself" at the door. But what will definitely begin as a hot and heavy rendezvous with an equally bold and daring partygoer might turn into a messy, awkward, and ultimately hilarious sexual encounter. Costumes might be fun, and they will certainly lower your inhibitions, but they are also hard to get off, they stain, and they have moving parts that can get stuck in very unattractive places.

Here, seven people share their funniest Halloween sex stories.

This girl successfully seduced a man while wearing a diaper.

I went as Tommy Pickles to a college party a few years ago (freshman year, so I was both bold and scandalous) and I went all out in a blue crop top and a white adult diaper. Yes, I went to a football house party with CVS-brand Depends on, with some sheer, skin-toned tights I borrowed from a much tinier dancer down the hall. I was out and about doing my thing, when I saw a cute, shy guy from my year walk past me. I immediately jumped at him and made my bold, fearless, and way-too-intoxicated move. (He was wearing all black and dressed as a robber — wool black hat, some black face paint, and black gloves in all.)
I was able to smooth talk my way into us making out by the keg and eventually taking him back to my room. It is a tad fuzzy on the rest of the night, but some key highlights include him sexually trying to remove my pants, only to remember that I was in fact wearing an adult diaper and me struggling to take off the tights that I had borrowed from a girl half my size. (we've all been there... right?) Next memory involves him having sex with me and looking horrified at me, not understanding why there were black smudges on my face, forgetting he was wearing black face paint, and then, me looking for paper towels, only to end up using the adult diaper that was previously on my body as a facial napkin. Seriously, we've all been here, right?
Well, long story short, I have successfully propositioned someone while wearing an adult diaper and have used it to wipe my face while having sex.

— Anonymous, 24

This girl had no clue what her hookup looked like.

About five years ago, I went to a cool hipster bar on Ossington in Toronto. I was introduced to the owner, and we had mad chemistry. We made out, and I went back to his place with him before sneaking back to mine in the middle of the night. The whole time this happened, he had his face completely painted. To this day, I don't know what he looks like.

— Jen, 32

This guy got his face makeup everywhere — and his friends ruined everything.

I decided to be a clown for Halloween one year (which immediately was my first mistake; who ever wants to hook up with a clown?). I maybe overdid it, because I went full face paint and everything, with a white face, big red lips, and big eyes. Naturally, I was scaring most people away, except for one girl, who seemed almost too excited about my costume. We were dancing and getting up close and personal, and we all know how disgusting college basements can get. I kind of let the fact that I was wearing face paint slip my mind, and the girl didn't notice in the dark basement (at least, I hope not).
We started to hook up, left the party to go to her place through the basement door, and as soon as we walked under one of the streetlights, you could see the mess I'd left all over her face. It was such a strange mix of colors, and naturally, they were mostly around her mouth, neck, and face. Because I was pretty embarrassed and didn't wanna spoil the mood, I decided to not bring it up.
We were walking back to her house, and of course, we ran into a bunch of my guy friends, and they had a FIELD DAY. Poor girl ran home, and I went home that night a sad clown.... only to find that my personal door was locked because somebody decided to have their own little get-together in my bed. I was banging on the door, trying to get someone's attention, but no one was responding, and I didn't hear any noise. I went around to my first-floor window and found it wide open. I climbed in, only to find my bed completely disheveled and part of a girl's deer costume and her denim jean jacket.
As if I wasn't grossed out enough by what probably went on in my bed, I turned the lights on to find drops of blood all over my sheets. One of my neighbors told me the next day that he witnessed a guy and a girl drunkenly climb (and fall) out of my window and run off. To this day, I still have no idea who this infamous Bambi was.
So long story short, I failed to close because I covered a girl's face in makeup, then had to buy new sheets because some couple decided to cover my bed in blood (and God knows what else).

— Dan, 22

This girl was too lazy to clean up the mess she left.

The first time I ever bootycalled anyone was on Halloween freshman year. I was dressed up as Yik Yak, but I had made a large part of my costume by putting whiteout on duct tape. So I was hooking up with this guy with the lights off, and once we finished and turned the lights on, there were white flakes literally all over his bed and all over both of us. I didn't want to clean it up, so I told him I had work in the morning and left.

— Suzie, 21

This girl's Little Mermaid costume went full Psycho.

Sophomore year of college, my roommates and I dressed up as Disney princesses. I was Ariel. Being a natural brunette, I used aerosol hair paint to achieve the fire-engine, Little-Mermaid red. That night, I went home with a dude and woke up to find red paint EVERYWHERE — on his sheets, his walls, all over our hands and bodies. It took almost an hour of scrubbing to get it all off, and my shower looked like a Psycho murder scene.
We dated for five months after that.

— Kate, 24

This guy's costume literally choked his boyfriend.

Last year's Halloween, I was a vampire, which was my first time being a vampire. I bought this cool incisor teeth mold to put on my two teeth. I spent the majority of the night putting on the fangs and then keeping them maintained throughout the Halloween party. I continued to drink, got drunk, then started hooking up with my boyfriend. I didn't take off my fangs because, like, why not.
While we were kissing mid-sex, one of my fangs got dislodged from my teeth and plopped into his mouth. I was over him, and the way it fell, it got into his throat. We had to stop because he had to cough out my vampire tooth.
We did end up laughing it off, but so much for trying to be a sexy, kinky vampire...

— Sal, 23

The takeaway? If you're trying to get some this Halloween, maybe keep your costume simple.

Check out the entire Gen Why series and other videos on Facebook and the Bustle app across Apple TV, Roku, and Amazon Fire TV.