This article examines two manga, Stop!! Hibari-Kun! and No Bra, which prefigure the increasingly popular anime and manga genre of otokonoko from a queer studies perspective. Otokonoko, also known as otoko no musume, is a genre of manga in which persons assigned male at birth (AMAB) wear women’s clothing and are perceived as attractive women. The term otokonoko (男の娘) is pronounced identically to the term男の子, meaning boy-child; however, due to a pun in the kanji which replaces "child" (子) with "daughter"/"girl" (娘), it translates to “boy-girl”, “boy-daughter”, or sometimes“boy-princess”. It is often translated into English as “cross-dresser”. The genre emerged in the early 2000s and has since become a popular point of reference and conversation both within and outside of anime and manga communities. Both the genre, and its titular characters have become iconic within both Japanese and Western online culture. As with most genres, the otokonoko genre is trope heavy, so I decided to look at works that prefigure the genre to better understand the appeal without the weight of the traditions of the genre weighing too heavily on the content. Both Stop!! Hibari-Kun! and No Bra follow the story of a boy who becomes increasingly attracted to a gender ambiguous character assigned male at birth, but who appears female to most. Both manga are centrally about this conflict between the love interests’ perceived maleness and the protagonists perceived heterosexuality. The article analyses the appeal of each work to both male and trans feminine readers, because what would later become the otokonoko genre is popular with both male and trans feminine readers. It also argues that these manga offer something unique from Western depictions of transgender lives, based on the popularity of manga and anime among Western trans feminine readers.