adventures in sex

14 Weird, Costumed Halloween Hookup Stories

Photo: Blake Wright

For children, Halloween is a day to eat candy and run around in a cape. For adults, Halloween is a night to drink to excess and express their sexuality while wearing an unflattering wig. The hookups that occur on Halloween are, inevitably, the strangest of the year. Last year, the Cut collected walk-of-shame stories from our most sluttily costumed friends. This year, we focus on the costumed hookup itself — through 14 thoroughly sexless costumes that still got the wearers laid. Welcome to the weird world of fucking while dressed as a serial killer, a beloved children’s character, or a pregnant celebrity.

1. Crazy Britney’s Baby-Bump Seduction

Photo: Blake Wright

It was 2006, just before Britney went full-on umbrella craze-balls. I needed a cheap and easy Halloween costume, so I threw on a strapless swimsuit cover-up, horrible Uggs, and aviator sunglasses. Under the dress I wore one of those Spanx tube-dress undergarments over a throw pillow. It made for a pretty realistic-looking bump. True story: Buying a six-pack on the way to the house party, I was asked by a woman in the checkout line when I was due. (Go, Idaho!) But once I stretched the Spanx over the pillow, there wasn’t much left to cover my crotch.

If I’d known I was going to see an old hookup at the party — dressed as a pirate and looking hot — I might have gone as “Oops! … I Did It Again” Britney. He rubbed my belly. We got shitty drunk and conspired about where to fuck. “Get your pregnant ass upstairs,” he whispered, and though the upstairs was off-limits, there we went.

I pulled up my dress, climbed on top of him, and shoved the baby bump off to the side. I tried to kiss him over the bump, but it was too cumbersome, so instead we just fucked with our costumes intact. Then, a knock at the door. I shushed my pirate, hoping the interloper would leave, but nope. The door swung open. It was the host and hostess. I will remember that moment for the rest of my life: Two friends standing over me, laughing in horror, while I, pregnant Britney Spears, humped a hot pirate on the floor with the goddamn lights on. They still tease me about it.

2. Depends on Your Definition of Sexy
I was dressed as Jeffrey Dahmer, which nobody should find sexy. I hope I took my fake mustache off before I kissed my hookup. I remember wanting to make a cannibalism joke when I ate her out. I hope I didn’t.

Photo: Blake Wright

3. “It’s-a-meee, Mario!”
I went as the Twitter Bird. Blue wig, blue dress covered in feathers, Twitter T around my neck, bird beak on my nose. I was monster-mashing to “I Want Candy” when a guy dressed as Super Mario pointed to a door and said, “I’m going to go in there. Meet me in five minutes.” When I walked into the room I shouted, “It’s-a-meee, Mario!” because I’m erotic like that. We hooked up there. Feathers. Everywhere. Like an avian crime scene. When we were done, I zipped my J.Crew dress back up and took a cab home, so proud of myself for successfully repurposing a bridesmaid dress.

4. A Is for Awww
I met a boyfriend on Halloween last year. I was dressed as a librarian: cardigan, round glasses, long skirt, dowdy wig. I carried a dictionary around all night. He hit on me by asking me to look up the word adorable.

5. The Most Wonderful Thing About Tiggers
My sophomore year of college, back when I was a chain-smoking vegetarian and weighed 100 pounds, I bought a children’s Tigger costume at Walmart. I think it was supposed to be subversive, drinking and smoking while dressed as a children’s character. The kind of thing that feels transgressive when you’re 19. My boobs looked pretty big in that children’s-size top, though, and I won my ex back that night. He was dressed as a dinosaur, and somewhere in that blur of pot smoke he said he was still in love with me. I don’t remember how I got out of the tiny Tigger costume, but I don’t think I wore it during sex. We stayed together another year, and then he broke my heart and kind of ruined college for me.

Photo: Blake Wright

6. Crackle Peed Her Leggings
I was Pop of Snap, Crackle, and Pop. My hookup was Fred Flintstone. Fred’s roommate kept saying, “Hop on Pop, tap Snap, tackle Crackle,” but we didn’t all find hookups that night. Crackle peed her leggings on her way back to the dorm.

7. Ironic Sexiness Results in Ironic Blow Job
My best-ever Halloween costume was a joke about slutty Halloween costumes: “slutty Julian Schnabel.” At the mall near my college I saw slutty men’s pajamas in the window at Forever 21. I bought them. Then I bought slutty yellow-tinted sunglasses and nail-polished the frames black. Then I threw a hot vintage Armani blazer and Rachel Comey heels over the whole thing, and took my ass to a party feeling clever as fuck. Then I gave a studious blow job to a guy who turned out to be gay. Hey, it happens.

8. Tongue Twister
I bought a game of Twister, glued the dots to a white painter’s suit, and wore the spinner as a hat. After a couple of trays of Jell-O shots, asking girls to spin the Twister board on top of your head is a surprisingly effective method for getting attention. The hookup consisted of me going down on a girl, me being too drunk to get it up, her waking the house up anyway. I honestly didn’t do that much, she was just loud.

Photo: Blake Wright

9. The Mummy’s Shocking Discovery
I had just landed in Australia and had no costume, but some people I met in the hostel elevator insisted I go out. These things happen in hostels when you’re 22. They took me to the bathroom, wrapped me in toilet paper, and called me a mummy. As soon as we got to the club, they abandoned me. Toilet paper rapidly disintegrating off my body, I was finishing my drink and preparing to leave when a guy comes over and starts flirting. Within the hour, I’m on my way to his apartment, ripping the remaining toilet paper off as we walk.

It was a good hookup! Except he did the shocker without any warning. I was, like, actually shocked. But it also felt nice? I mean, he totally should have asked, but I guess he got lucky because I actually enjoyed it, once I got over the initial … shock.

10. Goths Get the Last Laugh
I was in the offensive-costume phase of my life when, at age 19, I decided to make fun of goths: pale powder, black lipstick and eyeliner, and Band-Aids slapped over squiggly red lines drawn all over my arms and wrists — gallows humor about cutting. In this ghastly attire, I attended a frat party full of sexy cats and naughty angels. The only boy willing to speak to me was a pledge sidelined from the festivities because his arm was in one of those right-angle arm casts. Weakest member of the herd. My costume had gone method: I was the pallid outcast of my own derision.

Starved for attention, I drank as many beers as he could pump with one hand, then followed him home and smeared my disgusting makeup all over him in a tiny twin bed, his arm propped at a right angle the whole time. When I retired to the bathroom for a black-lipstick-tinged puke, I caught sight of myself in the mirror. I had truly become a self-destructive goth train-wreck. Beware Halloween, make-believe is dangerous.

11. It’s Raining Bros
It was my first Halloween in New York. My friends were dressed like slutty Village People — sexy cop, construction worker in stiletto Timberlands — and there I was, dressed as a rainstorm. I’d painted raindrops on my face and wore a blue dress, blue tights, and blue rain boots. I carried an umbrella that, when opened, had streamers and cutout clouds. I looked like an art teacher. I met a “nerd,” as in a bro dressed as a nerd, and because I like nerds I was attracted to him. Six shots later, I went home with him. The face paint ran and I was a sweaty mess, but on my walk home the next morning, it rained. My outfit was perfect.

Photo: Blake Wright

12. I Vant to Suck Your Rave Candy
Sometimes the real scare happens after Halloween. Dressed as the Hamburglar, I once made out with a vampire who later turned out to be a serious raver. JNCO jeans. Wallet chain. I spent several years running into him, always wearing giant candy necklaces and other nonsense. So this is my Halloween hookup PSA: Be careful whom you take home in costume, because you might get a surprise when you see them out of it.

13. I Was a Frumpy FUPA Mess
I was Rosie the Riveter in a dowdy denim jumpsuit that somehow managed to be both mom-jeans-colored and Euro-trash ugly. Lots of elastic scrunchies and unnecessary zippers. With a bandana and too much cheap red lipstick, I was a frumpy FUPA mess. But I went to a party, danced my face off, and went home with a hunk who made his own loft walls out of what must have been plywood-colored tissue paper. The walk of shame was trying to find the right door. I couldn’t tell which was the front door, bathroom door, his roommate’s door —  all DIY loft doors look the same! Afterward I tried to date him, but he turned out to be anti-Semitic. WTF.

14. The Lobster Left With the Dog
It was my first post-college Halloween. A girl I had a crush on all through college, lived in the city I’d moved to and I was eager to impress. Her favorite holiday was Halloween. She invited me to a house party and mentioned a friend was going as a chef and needed something to cook. Since a two-person costume with bland outfits is still an improvement over a single bland outfit, I decided to dress as a lobster. I already had a red onesie, with feet and a butt flap, so I dashed to a hardware store for pipe cleaners and foam board. I fashioned two claws, antennae, and eyes from a ping-pong ball.

My crush was dressed as Bo Obama, a topical costume for 2009, adorable floppy paws and that rainbow lei. Somehow I landed a kiss on her and we completely abandoned our friends. Back at the party, someone flatly told them, “The lobster left with the dog.”

The next morning, the feet of my onesie were completely worn through. I had a single twisted antennae and one ripped claw. I overstayed my welcome at her apartment. I made pancakes in that onesie. I resisted leaving as long as I could, then finally walked two miles home in the rain.

Five years later, we are still together. We live together, too.

14 Weird, Costumed Halloween Hookup Stories