Just so you know, the title of this is "Okama Witch etc..." this is not at all about trans. Okama are thing in Japan where a man just dresses up as a woman without going through any kind of operation.
Like someone said before character like Haruhi's father, Bon Clay from OP and LaDiva from GBF. I believe that it has more to do with "having a woman's heart and being in touch with it" than being a woman.