Definitions by cashboxmoneybags

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.

Chestering by cashboxmoneybags August 29, 2025