He did, in 1961 while visiting Santiago, Chile, while he was an Assistant District Attorney of Suffolk County (Boston), Massachusetts (not clear if this was on the taxpayers’ dime):

“While Kennedy was in Santiago he made arrangements to ‘rent’ a brothel for an entire night. Kennedy allegedly invited one of the Embassy chauffeurs to participate in the night’s activities.”

Afterthought:  I wonder if he had any waitress sandwiches while he was there.

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