I'm wondering if there are any anime fans out there who recall having watched anime that explore either crossdressing or transgender or gender role issues in a related way.
FtM is sort of touched on in Ouran because the main character girl is mistaken for a boy and the target of male female affections when she joins the Host Club. Women with masculine qualities are also present in Rose of Versailles and Oniisame E which were very good.
There's a comedical approach to MtF in Minami-ke where the girls of the family pressure the youngest's classmate to dress as a boy and he gets in the habit of doing it pretty much every time he visits.
The issue is sooorta approached in comedical fashion in things like Ranma and Naruto, but involving magical powers and males retaining a male mindset while in female form, which differs from TG.
Recently what made this come to mind and make a post about it is I started a new series called Hourou Musuko. It has eleven episodes and is probably the most serious and indepth approach I've seen taken so far. Not only does a guy dress as a girl but I think it's clear he sorta enjoys feeling like one too. There's also a tall girl who wears a male uniform in the class.