Yeah I get where you're coming from.
Like, I'm a bisexual male.
But I have preference for femininity.
That's to say in BOTH sexes I very much prefer a 'pretty' look.
HOWEVER. While I fancy extremely feminine girls exclusively, and likewise fancy rather androgynous - looking guys, when it comes to the males I NEVER go for a degree of androgyny where you literally couldn't tell at first glance what sex that person was. I like boys who look refined enough to 'almost be' a girl, while still being UNAMBIGUOUSLY AND IDENTIFIABLY male.
.. As for the friend you mention, sorry but I reckon he's just a chaser with a peculiar fetish. He gets off to the idea of a 'chick with a dick '. Let me tell you, no genuine trans woman wants to be thought of that way, nor is generally comfortable using her natal genitals. Him going after trans women in EXPLICIT preference to just, well women in general, to me says he may be a repressed gay because he wants a cock up his arse while pretending that's somehow still 'straight' intercourse. Like would he still wanna be with a trans woman who had undergone SRS and was in every respect female -?
.. I kinda doubt that from your description.