I love femboy wearing 学ラン. I want to see him get erect in his 学ラン.
However, it seems like he just crossdress for the prize or being famous, not his hobby or doing what he loves. Also, I feel like he has a dislike to his father because his father is a femboy model and not protect the mom, it seems like he also follows social gender.
I have a feeling that he will stop crossdressing right after he graduate or when he get caught (but it seems like he already got caught, but still crossdress, so I don't know, maybe it may helps him better grade like he mentioned it in early chapters)