I can't relate to this manga at all. She's hardly grown up, I don't think I would see her as a romance candidate... so I'll be dropping this.
EDIT: Hardly grown up is a nicer way of saying she is a loli / kiddish.
Is cross dressing allowed in Japan's schools? And also a guy cross dressing as a cute girl in an all-boys school definitely feels like would end up leading many boys astray in many ways.