Chestering

Chestering (noun): A playful activity where Person A first uses a dildo to gently widen his urethra. Once the urethra is stretched enough, Person B then inserts their own penis into that urethra, fitting one penis inside the other until climax.

Chestering is very popular in prison.

by cashboxmoneybags August 29, 2025

Chester Cuckhold

When a woman ties her boyfriend to a chair and has sex with another man. However, her boyfriend is faced away staring at sheep photos whilst listening to his girlfriend cheating and still gets erect.

Lewis: ‘How’s it going with your girlfriend?’

Aaron: ‘Not great she did the Chester Cuckhold to me last night’

by Meaty Martin 17C October 26, 2025

DC (Don Chester)

Gay, drag queen, republican, ghetto but ah redneck = DC

Girl you are so DC (Don Chester)!

Bout to pop off a DC (Don Chester) in this 8!+€#

by DC,Don Chester,DC(Don Chester) November 1, 2025

chester

pedophile with a small dick

Where is Jamie and the kids? Beware of Chester!

by konjac November 23, 2021

Chester Drawers

It's chest of drawers but the southern way to say it.

"You have some nice chester drawers in your bedroom."

by Soup17 January 31, 2025

Chester

A loser, someone who you have no respect for, an overall clown

“Yo you wanna go to Brent’s house tonight?”
“Nah man he’s a total Chester”

by Matt50baller February 5, 2025

Chester's Revenge

The act of fingering a girl after eating a whole bag of flaming hot cheetos.

I gave my girl a Chester's revenge last night.

by Bosstedeg6 February 11, 2025