Originally used to describe a man of independent wealth who could pursue whichever interests he so chose while the average man was busy working. The term was used by pimps to describe the lifestyle they had embraced.
Momma - "Boy, how you get all this money? I know you ain't workin for it."
Son - "Momma, you know I'm a man of leisure."
Momma - "Is that what they're callin it these days. You just a pimp and a mack. You ain't foolin no one, boy!"
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A prostitute. A euphemism (light way, better way of saying) a prostitute.
As I was in Vegas I spent some time with a woman of leisure over cash.
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Pretty much the same as a man of leisure except she has a vagina instead of a penis.
Being born into a wealthy New England family Kate Hepburn was the kind of woman of leisure who, these days, might be found on wealthymen.
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A snooty way for a woman to say she's unemployed
Anne: Hey Elisa, what did you say your job was?
Elisa: Oh I'm a lady of leisure! I just do whatever and see where life takes me.
Anne: So you're basically being pretentious about being unemployed?
Elisa: Am not! I was using it ironically!
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Jumping in mid-air over (usually) a body of water and striking a leisurely pose as if, say, laying on the beach reading a book.
John's leisure dive of him in a full tux with a martini glass over the pool was epic.
A man who makes his living off of prostitutes. A pimp, mack, or easy rider.
Cyrus styles hissself a gentleman of leisure but he nothin' but a low-down, raggedy-ass pimp, if you axe me.
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A career spent not having to work that is usually the result of inheriting money from your parents.
My buddy Bob is a leisure activist. He hasn't ever had a job and he lives off of his annual dividend check from his parent's company. I think he just got back from 6 months in Thailand.
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