Back in my professional theatre days, I was cast in a couple roles that had me cross dressing as a comedic character (one was for David Mamet's "Revenge of the Space Pandas" where I played the main character's mother, the other called "Dick Whittington and his Cat" where I played one of two hustling salesperson sisters).
Come to think of it, high school choir had me and two others in "geisha" drag for a rendition of "Three Little Maids From School" (which in retrospect was probably pretty damn racist), and that was for free.
But in those days I was built like an ostrich, and that's far from the case now (also, my feet are awful, so no way could I do heels now). So I've already done so, but me doing so now would probably not be ideal and likely extremely uncomfortable/physically painful.