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.
by cashboxmoneybags August 29, 2025
Get the Chesteringmug. by FilthyFozzie October 4, 2022
Get the Flamin' Chestermug. by Achluophobia April 4, 2020
Get the chestermug. Will blacked out last night, at 2am after stumbling across the street to the gas station he came back and crushed an entire bag of Cheetos, then chestered himself to sleep.
by Hang Eleven December 20, 2020
Get the Chestermug. The best person ever, never leave them, treat them like a queen, do anything they want, give them anything they ask!!!
Caitlin Chester :can I have a new phone?
Person :why?
Caitlin Chester :because my name is Caitlin Chester!
Person :why?
Caitlin Chester :because my name is Caitlin Chester!
by Teehee you don’t know me February 12, 2021
Get the Caitlin Chestermug. 
