"The Shady MilkMan": Is the man that is taking care of your Wife (or Girlfriend) while you are overseas. While he is taking care of her she is taking care of him with all of the money that you have earned from the ( Enter any Military Service here, except the Coast Guard). The shady Milk Man has often been referred to as a "Smooth Operator", " Jody", "Slick Willy", "Bad Motor Scooter", "Sancho", and "Tyrone".
Preach: So did you hear about my wife Brittani?

Money: Yeah I hear she got knocked up by "The Shady Milkman" while you were gone!
by The Preacher 478 February 02, 2010

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