To try for a serious answer to a question asked perhaps tongue-in-cheek, I'd like to think that by 3 or 4 hundred years from now society would have evolved to a point where non-coercive sexual behavior would be nobodies business except the parties involved, however these things ebb and flow. Clearly Kirk's time, given his behavior and the "uniforms" of female personnel, is on of a more libertine nature. By the 24th century, who knows. Given that the Federation consists of multiple societies, some are perhaps on the "upswing", others on the "down".
The very existence of a place like Risa, a planet devoted to what might be called "Tourism prostitution" implies, not a more liberal attitude toward sex, but rather a more conservative one as such places only thrive as safety valves for suppressed urges.
Just don't get caught with a naked Bolian.