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Does it strictly refer to taking someone's virginity, or does it express sexual intercourse in general?

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2 Answers 2

Nobody "picks" anybody's cherry. Cherries are "popped" and cherry in this case refers to hymen.

To "pop one's cherry" in a non-sexual way is to do a thing for the first time.

Cherry-picking is something else altogether.

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Which means you engage in cherry picking if you choose only the rules you like in a set of rules when you are supposed to use all the rules... –  mplungjan Mar 4 '11 at 13:54
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Cherry picking is also used in sports for someone who puts forth almost no defensive effort, relying on teammates to perform the defense and make a favorable play (like stealing the ball) but instead positioning themselves for the easy offensive play. It's typically combated by rules like "off-sides." –  corsiKa Mar 4 '11 at 17:52
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It's not just the hymen. Popping one's cherry can also refer to anal intercourse. –  TRiG Aug 5 '11 at 0:31

From the New Oxford American Dictionary:

cherry (noun) 4. [in sing.] [vulgar, slang] the hymen, as representing a woman's virginity.

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protected by tchrist Jan 12 '13 at 3:52

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