When a TV show or movie forces a demographic into a role that fits like a square peg into a round hole, often to appeal to a woke audience.
Yo man makin' shaneequa a crochet-lovin' bookworm ain't. Dat girl booty way too juicy to be sittin' crib friday nights knittin sheeit. Square-pegging is all they doin.
by McCollege December 2, 2023

When a particular straight male who happens to swing gay gets it in the ass by an extra large strap on
by Paulie s friend February 14, 2021

when you want to “peg” some one and you need money at the same time so you peg ya for a tenner. However you could use more money like twenty or a fiver , that’s a bit cheap, or even if you’re feeling it £50
by kennedino February 7, 2019

When a guy rizzes a girl up, but everyone knows he is secretly trying to get her to strap a bad dragon and jackhammer is brown town fun button, he is known as peg bait.
by Melchiah March 26, 2025

For guys who want to date Trans Women, but don't want the stigma, or haven't come to terms with it yet.
by Keeberz January 4, 2022

oh my god when my girl was pegging me all i could imagine was how she felt when i was rawdogging her from behind
by weirdo62628584949282845 November 15, 2024

Between two persons with male genitalia. One wears a strap-on backwards and fucks the recieving participant's ass by having said participant doing a head stand with hips and knees bent 90° in a sitting position. The participant with strap on, stands up and sits down on the chair structure formed by the recieving participant, inserting the strap on into the recieving participants asshole.
by Tuguit August 16, 2020
