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

get naked at school challenge

An internet challenge encouraging high school students to get naked at school for social media clout

Did you hear about the guy who did the get naked at school challenge last week?

Yeah he was crashing out over social media clout

by anonymous April 19, 2024

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

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

Five Week Challenge

When a male tries to go five consecutive weeks without masturbating. Sexual activity with others is permitted during the challenge—only self performed actions are forbidden.

Ever since I started the Five Week Challenge, I spit game all the time. I can't help it—I'm so horny!

by theschrine August 9, 2012

Beer Bottle Challenge

Take a beer bottle of your choice, any size, extra large encouraged, and shove it up your keester and try to yank that puppy out.

Little Johnny tried to impress the crew with the good ol beer bottle challenge by pounding a mickeys in his bhole. Couldn't pull her out, ended up in the ER.

by Tung "Punch" Bungwhole March 22, 2023

Handcuff Dookie Challenge

A challenge where one handcuffs themselves to the bed and swallows the key, they then have to stay there until they dookie it out and unlock themselves

It took me 33 hours to complete the Handcuff Dookie Challenge

by ItAintObeeezy May 26, 2025