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1.
When multiple males encounter a fat chick (If a fat chick is unavailable please see: Dirty Farmer) and are able to coerce her into receiving the Bukkake Resevoir in her fat rolled belly button thus giving her the "Dirty Sailor". For added enjoyment follow up the "Dirty Sailor" with the sensational "Drop Anchor" and "Barncicle Cleaner".
Ryan and the Mikes found it suprisingly easy to engage Rikki Lake in a session of "Dirty Sailor" love.

That whale is so filthy she can't get enough of me and my buddies "Dirty Sailor".
by Mike - Mike - Ryan January 03, 2006
 
2.
When a horny guy punches a girl in the nose so it starts to bleed and then cums up it.
David: Hey baby can i break your nose so i can cum up it aka Dirty Sailor?
Alexa: Hell ya baby, lets hope it bleeds alot.
by love to dirty sail January 09, 2010