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1.
taking more time or advantage than you're really due because you can get away with it. Short for "milking it for all it's worth."
Sara's at home taking care of her sick boyfriend. Hasn't he had that cold for two weeks? Yeah, he's milking it.

Isn't Bill back from that job yet? Still gone, he must be milking it.

Is Johnnie still crying--she hardly hit him? Oh, he's milking it.
by Scott ATL March 13, 2013
 
2.
The act of filling a bong with such an excessive amount of smoke, so it appears to be filled with milk.
Oh shit, he's milking it again!
by iMilkedCLarence December 10, 2010