cookie cum challenge

A group of males squat around a cookie and jack-off, releasing their ejaculate onto said cookie. The man who finishes last must consume the cookie.

Did you see John totally lose the cookie cum challenge? He ate the cookie in one bite.

by stonedgaytheist September 28, 2017

The Last Name Challenge

Going to a porn site and typing your last name in the search bar, results may vary.

Zack: I did the last name challenge yesterday, thank god I found nothing!

by JustAnotherSickFuckOnUrbanDic June 26, 2021

Andrew Parkinson Challenge

A challenge in which you curl your finger into a hook and slam down the side of your finger against the edge of a hard surface. Who ever winces or drops out first loses.

Sol- Man, did you hear that Brendan broke his finger playing the Andrew Parkinson Challenge?
John- Yeah, he definitely won

by Parkingticket April 25, 2023

November Challenge

The November Challenge is when a guy goes without jacking himself off for the entire month of November. Usually this challenge fails or the guy is lucky and gets some ass.

Damn! Colin totally lost the November Challenge!

by EdieC November 22, 2006

NyQuil Challenge

Drink 10floz(1 bottle) of Vicks NyQuil or 2 bottles for nightmare difficulty, and then quickly try to masterbate before you fall asleep. If you succeed you win!

I got about 20seconds into the NyQuil challenge on nightmare mode before losing, but I was already tired when I started.

by startrestart March 5, 2010

Chadillac Muskalade

Chad Muska's Escalade

We saw the Chadillac Muskalade pull into the park and all got boners.

by Johnny Fitswell January 17, 2018

monroe challenge

A sacred event utilizing the monroe transfer technique in which two indiviudals stick tubes up their asses and try to overcome their adversaries shit pressure to push their shit up their opponents ass. Usually results in broken hearts and messy floors.

Dude 1: You're a bitch.
Dude 2: Screw that... lets monroe challenge!

by Nick "Sink it, Drink it" Fertig August 4, 2006