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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."
by FakeTitties November 19, 2007
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Two or more guys that have had sex with the same girl
After you do her, we'll be hole brothers.
by Suna no Stevo June 15, 2007
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