Wouldn't that be cool? Ideally, a candidate who could understand those on both sides of the gender aisle?
Allegedly though, the closest we have come in recent memory has been FBI Director J. Edgar Hoover's closet full of dresses. These days, as we approach elections, LGBT organizations may continually have to fight tooth and nail for our freedoms. Let alone think about a trans president.
On another subject:
In my constant search around the world wide web, yesterday I did find another wonderful interview with Jennifer Finney Boylan from the New York Times called: "You've gone to a lot of trouble to be a woman-don't be a stupid one." Plenty of wonderful quotes for you to take a look at!