Does it strictly refer to taking someone's virginity, or does it express sexual intercourse in general?
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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.
From the New Oxford American Dictionary:
protected by tchrist Jan 12 '13 at 3:52
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