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Well Today Sucks!

I was gonna let it drop, but you guys keep on going.
So I asked my 85 year old father, just be sure I was right. He said it means to give someone hidden money, usually to do something for you that they might not otherwise do. Once again If any of you spoke Yiddish in your home then try telling me what it means. Saying that some movie made it sound like something else means nothing....

I don't doubt he was right in the past but word meaning, especially slang, changes over time. The Urban dictionary says to have sex, but so do these

This reference shows that the meaning seems to have evolved over time and gives some examples closer to your meaning.
BESSIE: You’re sure he’ll come tonight—the insurance man?

MORTY: Why not? I shtupped him a ten-dollar bill. Everything's hot delicatessen.

That shows your meaning so in context, at least in the past you were correct but I'd be careful using the term today. Dad was correct, at least a long time ago.

It was interesting to do a little research anyway.
 
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