It's also because this trans stuff is yet another example of Chris pretending to be something, complete with costumes he can dress up in. Chris likes playing dress-up, all the way back to his Pokemon trainer days, and through the Classic Era where he didn't hesitate to play pretend.
Remember when Chris was a Juggalo? ...for like a week? He put more effort into the face makeup than the actual music, but it was a group that Chris, for some reason, identified with, yet was too dumb to know exactly what it was all about.
Chris going trans, the first thing he did was trowel on makeup, looking absolutely hideous, but it's playing pretend, and he gets to dress up and paint his face!
This trans stuff is no different. He gets to put on clothes like the girls he stalks and creeps on. It gets him in touch with his "lesbian soul", his one very strong fetish since forever, and it gives him victim points and other complicated nonsense he can give word salads too.
Remember though, in 2007, none of what Chris said about "the homos" was troll driven, that was 100% his thoughts. I have to wonder if these days, when Chris says he's "bi", that's just not some retarded double talk for "I'm a girl, I'm bisexual because I like other girls".