Dick Boss

A pimp (or pimptress) who pimps dudes.

Life sucked before I met LaToya... She's the greatest dick boss ever to hit the streets.

Dick Boss by Th3Dol3 June 5, 2009

Ross, the Boss, Big Dick Mandingo 

An infamous card breaking participant that plays like a boss and is well endowed.

Josh Allen refractor for my guy Ross, the Boss, Big Dick Mandingo.

Ross, the Boss, Big Dick Mandingo by Soy17 April 24, 2023

dickboss 

A supervisor, boss or otherwise co-worker that is generally disliked because of their exercising authority.

Dude, the senior software developer actually made us do some work. What a dickboss.

dickboss by themachomanrandysavage June 28, 2010