Hope adults are okay. Here's Hibiki Amawa in his guy and lady form trying to be a teacher at an all girls school. From I My Me! Strawberry Eggs. I had forgotten about this one last time I posted my favorite cross dressers. It's a pretty funny show.
Poland. The World's best Fashion designer. Or so.
There's a couple anime scenes where he dresses as a girl like the Halloween scene. And what appears to be a Gakuen Hetalia scene (don't know what episode it is though) .