The Keyhole Challenge

When two people having sex switch from one position to the next, without withdrawling the penis from any orifice.

She never really know what the true definition of victory until she had successfully completed the Keyhole Challenge

by Mae Rose January 30, 2017

Fat Cumshot Challenge

Type the words “Fat Cumshot” using ugly your Cumshot.

You: “Hey man have you done the fat Cumshot challenge?”

Friend: “No, what the hell is that?”

by PottassiumPotato May 18, 2021

Turd Bucket Challenge

When you fill a bucket with turds and pour it over your head

"I nominated my dad for the Turd Bucket Challenge"
"Oh shit, did he actually do it?"
"Yeah, I helped him out in his sleep"

by Tinkle Stinky June 4, 2025

Golden challenge

When sending a golden stream through your partners gap as they piss while sitting.

We both have to piss now, you sit and go, I'll shoot the gap for the golden challenge.

by Dicki007 May 18, 2015

seven year challenge

The challenge of hooking up with someone in every class year you will encounter in college, aka a senior when you are a freshman through a freshman when you are a senior

I hooked up with a sophomore last night, I'm one closer to completing the seven year challenge.

by bjork bjork April 15, 2013

Challenger

The worst type of boyfriend..like ever. He basically tries to catch online daters

"Bro this guy called Challenger added me on discord"
"Decline it! He's gonna play with your heart"

by choielias March 19, 2023

Challenge Pissing

NOT TO BE CONFUSED WITH THE BIG BILL HELL'S CHALLENGE PISSING.

A game where one or more people have to go to the bathroom to take a piss, and come back to their room in record time.

"Time me on this Challenge Pissing contest. See if I can beat that old hag Maury."

by Geestorn May 14, 2023