Jouji had an extremely bad first experience with magic and reacted poorly. He's clearly, from his outlook, attempting to run it back, but you're pressing so hard on him he's not allowed to.
Honestly, from experience with case studies, the more you press on someone the more they desire to act out, if anything you're making his own neruoses about this even worse.
I don't like him but honestly you need to give him more breathing room, because you're creating your own worst nightmare.
Jouji, if anything is trying to be a model student and little brother here. Anything you're imagining you're doing in terms of horriibleness is in your own imagination.
Maybe its a reaction to the pressure you're putting him under. People often develop escapism in different ways to outside stress. Maybe by crossdressing he stops thinking of himself as Jouji for a while.
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