I am fully in agreement with you. Japan is far more advanced than the U.S. in this area. there are many boys who dress as girls in cosplay and street wear also, done without shame and often praised at how feminine they look. You can find many examples on the internet where these pretty boys are with their girlfriends who are probably the ones who dress them and do their make-up.
There was a TV show a few years back that would dress the boyfriends as girls and the contestants had to choose who were real girls and who were cross-dressed, it was wildly popular. To see how feminine the boys acted after being dressed was really eye opening.