In Senpai wa Otokonoko, first-year student Saki Aoi is hardly the only girl at school captivated by the beauty of Makoto Hanaoka, a senior on the school board. Even so, she works up the nerve to confess, despite worrying that Hanaoka might be uncomfortable receiving a confession from another girl. The answer she gets is unexpected for a completely different reason: Makoto is actually a cross-dressing boy. Fully expecting Aoi to be horrified by the revelation, he is stunned to find that she has no issue with it at all.
Makoto still rejects Aoi's request to go out with her, citing his identity and the fact that he has never fallen in love before. Aoi refuses to back down and insists that she will become his first love. As her determination keeps pulling him closer, their mutual friend Ryuuji Taiga becomes entangled in the situation as well, turning an awkward confession into a complicated love triangle. Beneath its romantic comedy surface, the series follows Makoto's struggle with self-acceptance and the question that lingers behind every new step forward: whether he can truly love someone else before learning to love himself first.