This is one hell of a great anime series. Yes, Senpai wa Otokonoko / Senpai is a Crossdresser touches some taboo subjects (especially if you think about the Japanese society) with ease and elegance. Senpai wa Otokonoko is an amazing show that includes such issues as cross-dressing, teenage homosexual and heterosexual love, insecurities, broken family ties, irresponsible parenting, compliance or incompliance with societal norms, and if you are not triggered by any of these issues you don't even feel there is a strong discussion going on while you watch it - you just see a series about friendship and tolerance. It may be the best written showsince Hoshiai no Sora / Stars Align. I fully recommend it.