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1.
After an extremely drunk one-night stand, when the girl is passed out drunk, you piss and outline around her body before sneaking out of the house.
I'm really glad I drank all that beer last night, It took a lot of piss to give that fat girl the ol' midnight sailor.
by OKCsavage May 30, 2009
 
2.
A notorius bedwetter, someone who can't hold their mud. Diaper wearing adult
"Can you believe Crane drank 12 beers and turned into a midnight sailor"
by Kaptain Poon Punisher December 12, 2007