What is Hole Brother?
1.
A title endowed to two male friends who have both fucked the same woman. The one who penetrates first gains seniority and thenceforth becomes the elder hole brother; however, there is no limit to the number of junior or senior hole brothers a man can have with a particular woman.
"You fucked Grace last night? Dude, I hit that shit back in '05! I guess we're hole brothers now."
"Our hole cousin, Adam, suggests adding hole cousins, or hole brothers by association."
See