Clyde Cash pretty much called it that Chris was going to have sexual identity issues before the tomgirl saga even began.
It's not so much Chris hating men as it is Chris hating the fact he is male. Fed on a lifestyle of indulgence, spoiling, and media stereotypes, he thought he was perfect and women should be throwing themselves at him (and I bet a small part of him still thinks this). The main reason he went down this tomgirl/tranny path is more out of his desire to actually get a new fuckmommy, and he was convinced literally every single straight girl for miles around was already taken by a boyfriend, and thus he's been angling the lesbian angle purely to get some carpetmuncher china instead.
In truth, him going full tranny is a result of overexposure to modern counterculture. He probably would have just been happy being a crossdresser if this occured a few decades previously (though at the same time things would be worse because autism wasn't even a blip on the radar a few decades back, either)