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Throwing money into the deal makes it shady and creepy (which it already a little is). Strip poker between two people is weird. Just play poker for money and then have sex later.
I'm not sure why strip poker with someone you don't know is creepier to me than just going home with someone you don't know... but it is.
I'm also not sure what the "question" part of this is. It sounds like you want to do it, then do it. The advice of strangers on the internet should be meaningless.
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