Cumchute challenge

When a person who is skydiving has to ejaculate to completion before they can open their parachute.

“Dude should I do the cumchute challenge when I go skydiving today?”

by lil swervy June 28, 2019

Three Hole Challenge

The act of achieving sexual penetration of all three orifices of a woman within a 24 hours period, often for charity.

Hey Dave you gonna sponsor me for this year's Three Hole Challenge? All funds raised will be going to a good cause.

by Polidicks March 22, 2023

The President's Window Challenge

A male masturbating and ejaculating out of a window, preferably a second floor window.

"Me and Hunter was doin the president's window challenge when we realized that there was someone below the window".

by Mr. President's Gay May 8, 2016

Cheese Hold Challenge

The Cheese Hold Challenge is a challenge where someone puts cheese in their butt and then someone takes it and holds it.

Jhon " Want to do the cheese hold Challenge"
Bob"First have to put the cheese in someone's butt then hold it nasty.

by Crackersak June 15, 2018

Jack in the box challenge

When you jack in the box of your jack in the box food

Yo bro I did the Jack in the box challenge my GF was so surprised
No way bro Ima try it out now

by MeatBallar October 25, 2022

Billy and Vadim challenge

Kill a 2 12 racks of white claws between two people in less than an hour

Damn ain’t no move tonight guess I’ll do the Billy and Vadim challenge

by dooley and dooley September 20, 2020

DDR Suicide Challenge

Double Dutch Rudder Suicide Challenge - The Double Dutch Rudder Challenge is when you find 3 homeless bums, get one of them to slit his/her wrists and try to get the other two bums off via Dutch Rudder before he/she passes out.

"Lets find some homeless bums and make them do the DDR Suicide Challenge"

by Yardape22 May 9, 2012