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

20 Minute Challenge

Shitting, jerking-off, showering, shaving, and getting dressed, all within 20 minutes.

Guy 1: Hey, we gotta leave in 20 minutes.
Guy 2: Alright, I guess it's time for the 20 Minute Challenge

by MCGymNastY September 4, 2016

Video Game Challenged

When a person is so incompetent in video games and should not even play the game at all.

He was so video game challenged that if he were not to play at all, his team would win. videogames gaming challenged videogaming gamer games

by SigmaOmega3 August 17, 2016

rough it challenge

a game played at camps, most commonly by males, where you go into the cabins and masturbate until you come on someone as they sleep. the objective is to not get caught.

Cale succeeded at the rough it challenge.

by Bhart4 December 17, 2016

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

human mail challenge

A challenge where someone mails themself to a friends house or random house and have food and water with them.

I wish I could do the human mail challenge.

by boaz274 March 18, 2017

Secret Cheerio Challenge

When you put a cheerio in random places, around him, around school, around the town, or even on a person without that person noticing.
If you do this, take a picture and post it on instagram or twitter with #secretcheeriochallenge

I decided to do the secret cheerio challenge! I put a cheerio on my friends head without her noticing #secretcheeriochallenge

by TOTofficial April 20, 2017