Cherries and sex.

My boyfriend and I were pitting cherries for some glaze and I wondered…

How did cherries become associated with hymens and the breaking of?

The OED doesn’t pinpoint it, but the earliest cite of this use is from a dictionary that says “cherry” is slang for “young girl.”

The gap between the first two cites might indicate the change of meaning.

As for the origin of the original definition, it may come from an English proverb quoted in the OED:

The connection between this and “cherry”=“young girl” seems a strong possibility.