I've got two things to say, here.
One, I was absolutely convinced this guy was a troll, at first. Like Big Titted Shop Teacher, I was sure this was someone being so deliberately over the top to try to rub people's faces in stupidity.
When he agreed to get his face butchered, I accepted that he wasn't a troll. Or, at least, wasn't only a troll.
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Two: Some trans people have a face that lets them pass. Not many, but some. With makeup, Dylan was... not great, but not the worst.
The surgery made it worse.
The surgery almost always makes it worse.
Better to look a bit mannish than to look like a plastic surgery abomination.
First of all, these people aren't trying to "look like women". They're trying to look like caricatures of women. It's always the same things - the permanently-surprised eyebrows, the glasscutter schnoz, the freakish chin. If you did those things to a regular woman, she would probably look horrific, too. That look isn't natural.
Second, like I said... Better to look mannish than to look wrong. With enough makeup Dylan looked somewhere between "okay-ish" and "not great." After the surgery, they look downright bad and weird. The surgery only highlights the things the surgery can't change, like the mouth being too large, the jaw being too wide, etc. There are things plastic surgeons can't fix, and when they try, it tends to lead to horrific disaster, like collapsed sinuses and stuff.
