I'm more academically disagreeing with you, because he's not being cast as trying to be a woman but being an object of shame for taking a female ornament, not playing the correctly manly man. This is definitely interwoven with transphobia, but I don;t think the reader is supposed to read him as playing woman, but being foolish or whoreish like a woman. It's wrong either way, but I split hairs over brainworms.