Definitions by Skippy Chesterson

Sailor Pussy

A derogatory term used to describe a cisgender hetero chubby gen-x or boomers goatee facial hair. Typically accompanied by mirrored wrap around sunglasses and a monster truck. The term originates from men doing each other certain favors while at sea.

Bill thought he was the epitome of masculinity, but his prominent sailor pussy says otherwise.

Sailor Pussy by Skippy Chesterson June 22, 2026