The Pioneer

A sexual position similar to the rear admiral. A man enters a woman from behind, with the woman wrapping her legs around the back of the man. The man then positions the woman onto a rolling, wooden cart and proceeds to roll her around the room, a la a covered wagon. This can get extra kinky if the man dons an old cowboy hat and calls the woman a dirty ox.

"Jasper, remember when you pulled The Pioneer on me? That really took me back to the Oregon Trail days!"

The Pioneer by Dr. Starfish November 12, 2006

The Pink Pioneer

When a women gets a dildo and sticks it far up a virgin mans ripe anus,which is uncharted ir unmarked territory,therefor a very risky operation

I gave my father the pink pioneer and now we've mapped his moon.

The Pink Pioneer by Nebraskaboi2299 June 8, 2018

Pioneering THE Enterprise 

Pioneering- involving new ideas or methods
Enterprise- a project or undertaking, typically one that is difficult or requires effort

Pioneering THE Enterprise- finding new ways to accomplish Gen Z’s greatest aspirations

Wow! Jacob and Rune are really pioneering the enterprise!

Pioneering THE Enterprise by PioneeringTHEEnterprise April 8, 2022

Grindset

The grindset is a contemporary ideology of self-exploitation disguised as strength, deeply tied to the aesthetics of the “sigma male” and to new digital forms of patriarchy. It promotes the idea that human worth depends on productivity, economic success, absolute emotional control, and the ability to work endlessly, turning vulnerability, rest, community, and tenderness into signs of weakness. Beneath its rhetoric of discipline and power often lies a profound inability to relate healthily to pain, fragility, and human interdependence.

“That’s the grindset, brother. While weak men sleep and complain, sigma males stay disciplined, work in silence, suppress emotions, and build power while everyone else wastes time chasing comfort.”

Grindset by Omega-Male May 22, 2026

jerb 

well known from south park
rednecks get angrry that future folk took there jobs so they yell
They took ouare jerbs!

Them future folk took ouare jerbs!

jerb by Jimberley Kim April 7, 2005

Cheeks 

An Irish phrase meaning shit, derived from ass
(Not to be confused with the literal description of one's buttocks)

"Did you hear the song Aylek$ dropped?"
"Hardly. Her music is absolute cheeks."

"My boyfriend say LaFlame is cheeks."
"Tell your boyfriend I said it's his mixtape that's cheeks."

Cheeks by thecartisan April 26, 2020

sans sheriff 

Lawless use of fonts or typography, with no regard to aesthetics or legibility

I'm putting this CV straight in the bin. Written totally sans sheriff.

sans sheriff by Jamarley July 3, 2019