I get a kick out of characters who blur gender lines, and if you want a protagonist who’s a femboy crossdresser, a few titles really stand out for me. One that I gush about to friends is 'Himegoto' — the main guy, Hime Arikawa, is literally forced into dressing like a girl by a school council that blackmails him. The series is slapstick and absurd, but Hime’s delicate, overtly feminine presentation and the way the show mines comedy from his predicament makes him an unforgettable example of the trope.
Another show I always recommend when this topic comes up is 'Otome wa Boku ni Koishiteru' (commonly called 'Otoboku'). The lead, Mizuho, is a boy who enrolls at an all-girls academy disguised as a girl; the show leans into romantic comedy and school-life beats, and Mizuho’s gentle, soft-spoken nature plus the drama of keeping his identity secret creates lots of memorable moments. It’s sweet, sometimes painfully awkward, and it presents crossdressing as both necessity and character-defining.
For a different flavor, check out 'Princess Princess' — it features three boys chosen to dress up as the school’s “princesses” to lift morale. The series treats the premise with warmth and camaraderie rather than just gags, so you feel for the protagonists as they navigate embarrassment, friendship, and the weird politics of their school. I love how each show offers a unique tone: absurdist, romantic, or slice-of-life, and they all make femboy crossdressers compelling in their own ways.