Most Helpful Girl
I'd break up with him but I'd support him at the same time. I believe it's your right to do those things but I am strictly attracted to masculine men who behave like men. If I wanted to date someone who wore girls clothes and makeup I'd date a female - but I'm not attracted to women, let alone men who dress like them.
I wouldn't shame him though, I'd encourage him to pursue what he wants but I'd be honest in saying that this is the end of our romantic relationship.
Most Helpful Guy
You know, I grew up with only sisters and every Halloween, I would dress up as a girl. My sisters absolutely loved the opportunity to dress up a life-sized doll and apply makeup, especially since using makeup was not allowed at their age. I don't know what adults women would think, but I'm hoping that they'd have at least half as much fun dressing up their partners!