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

chester pennington

Another name for a weed or dab pen for nu metal fans

"ughh im so stressed, hand me the chester pennington."

by y2kzgy May 12, 2025

Chester Pennington

Another nickname for the famed Dap Pen/ THC Vape. The Penjamin, Penelope, the Jimmy Pendrix etc.

Bro: Hey Bro lemme tap that Chester Pennington .
Me: Say less man… here, pre-heated for ya. Better not cough up a lung from that blinker mane.
Bro: Damn dude, that Toad Venom Hit… (Greens out)

by Østëň May 29, 2025

Chester

A little Chinese boy, struggling with his studies, often finds himself drifting off during lessons. His report card paints a clear picture, with failing marks across most subjects, a quiet testament to his challenges in the classroom. Despite his efforts, the exhaustion from his struggles often leads him to sleep in class, impacting his learning further. As well as this hes a bum

'Chester is asleep again'

by chester103 July 31, 2025

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