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

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

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

7 Day Challenge

Anal sex by girlfriend for a consecutive 7 days with no vaginal intercourse

ME: Yo bud, your girlfriend is hot. Has she completed the 7 day challenge?

FRIEND: The 7 day challenge? What's that?

ME: Anal every day for 7 days with no vaginal penetration.

FRIEND: Nah bro, she's as plain as vanilla ice cream.

by Phil6590 June 6, 2017

Seok Running Challenge

In public, Sprint as fast as you can with only your lower body. Your arms are pointed straight down and they cannot move.

Do the Seok Running Challenge in Walmart!

by ShunF November 12, 2017

jimmy john's challenge

When you order Jimmy John's and try to masturbate before they deliver your sandwich to the door.

I lost the Jimmy John's challenge again yesterday. Twice in a row I answered the door with a boner.

by Save yourself for dessert February 22, 2018