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I found it through the comments below:

What a shame. Dollars to your aunt's cherry the next thing to go will be the Beach Races - I'd put money on it.

And also here in the comments.

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-1 for not doing your homework :) –  Kris May 6 '13 at 6:05
    
@kris - I think that's a bit unfair. Unless one is a native English speaker, it might be tough to recognize the parallel between "dollars to donuts" and "dollars to your aunt's cherry." –  James McLeod May 6 '13 at 22:18
    
@JamesMcLeod I did not apply my background knowledge either -- looking around in various ways led me to the cited reference, which I found adequate. Homework is a prerequisite on ELU. –  Kris May 7 '13 at 4:42
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1 Answer

This is not a particularly classy expression.

Expressions beginning with "Dollars to..." (dollars to donuts, etc) are expressing that something is likely in terms of an implicit bet (if I'm wrong, I'll give up something more valuable to you, like a dollar, but if I'm right, you only need to give me something of less value, like a donut) (this particular example has lost some of its meaning with the inflation of the last eighty years).

Cherry is, in this context, a metaphor for female virginity. The tacit assumption is that "your aunt" is no longer a virgin, so her cherry is worthless.

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Sounds entirely plausible. However. How do you draw the interpretation? How do you arrive at the 'tacit assumption'? There is more of a hypothesis than an answer here, right? –  Kris May 7 '13 at 4:45
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