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A "Thailand surprise" is when your female date, prostitute, etc. reveals her genitalia, which, to your surprise, are male genitals.
The climactic scene in "The Crying Game" is a textbook example of a "Thailand Surprise."
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When you are a U.S. citizen, travelling abroad and you are caught by the local authorities with a prostitute of the same sex who has not reached the age of consent by U.S. law.
"Senator Hoffman found out first hand what a Bangkok Bugaboo is; the Massachusetts senator is facing 20 years in prison after being caught having sex with an 11-year-old boy in the Phillipines."
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