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First put into practice by a German exchange student. Meaning "to squeeze the breasts of a wealthy girl". More aggressive than fondling.
Did you milk the cash cow?
Yeah, she loved it! You should try milking a cash cow.
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Abusing the generous welfare state in Canada or the United States of America for your own personal gain.
If you have a business outside north America and you still live on welfare here in north America, you have a morality problem. Stop milking the cash cow.
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In his song, the reference is for a woman to let him ejaculate on a girls face while he masterbates. If she holds her head steady he'll milk himself.
ludacris hold the head steady I'm going to milk the cow
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From the song 'Yeah!' by usher, 'lil jon, and ludacris. In this part ludacris is talking about getting a hand job.
The 'head' being the head of his dick, and 'milk' being the cum out of his 'cow' (his dick.) He wants the girl to give him a handjob and make him cum.
Ludacris' part in 'Yeah!' :
My outfit's ridiculous, in the club lookin' so conspicuous.
And Rowl! These women all on the prowl, ***If ya hold da head steady, imma milk da cow!****
Forget about the game, I'm a spit the truth, I won't stop till I get 'em in they birthday suits.
So gimmie the rhythm and it'll be off with their clothes, then bend over to the front and touch your toes.
I left the Jag and I took the Rolls, if they aint cutting then I put em on foot patrol.
How you like me now, when my pinky's valued over three hundred thousand,
Lets drank you the one to please, Ludacris fill cups like double D's.
Me and Ursh once more and we leave 'em dead, we want a lady in the street but a freak in the bed to say ..
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Using an idea for a product that is now old, boring, and predictable.
That Marvel franchise is milking a sick cow at this point.
When one gives a guy a handjob
"Clio milked his cow after prom in Texas"
everything is where is it supposed to be, the task has been completed
The milk is in the cow and coming your way.