I am comfortable around those who cross-dress, who are transgender, or who break gender barriers in any way possible. This video is very sweet on the subject.
The video below is of a Japanese TV show in which older teenage boys get a makeover that changes them into older teenage girls. Apparently there's quite a few clips of this sloshing around YouTube.
I found this one quite touching when the madeover boy was kissed by another boy on screen. It would make an interesting subject for an essay on how transgender people are related to by same-biological-sex people.