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1.
Someone who likes to motorboat a woman's tits.
John: Claire's mom just made me grab her hooters.
Jeremy: Well snap out of it! What, a hot older women made you feel her cans? Stop crying like a little girl.
John: I wasn't crying like a little girl.
Jeremy: Why don't you try getting jacked off under the table in front of the whole damn family and have some real problems, jackass. Hey, what were they like anyway? They looked pretty good, are they real? Are they built for speed or comfort? What'd you do with them? Motorboat? You play the motorboat?
makes sputtering motorboat noise
You motorboatin son of a bitch! You old sailor you! Where is she? She still in the house?
by Sandbaggin' son of a bitch January 18, 2009
 
2.
A term given to someone who does something deserving of a title greater than "the man."
Dan: so i just found myself a new girlfriend today Jonsey. Matt Jones: I knew you would you Old Sailor!
by UNHDan August 12, 2008