This chapter discusses the difficulties involved in explaining the sociocultural paths followed by the “transgender” categories fa’afafine and tomboys in Samoa and proposes another gendered category: girls or women who are said to be born as girls but who come to be viewed as behaving like men at about the same stage in life as when boys become fa’afafine. The chapter first considers Western discourses about fa’afafine and goes on to discuss the role played by mothers in “bringing up boys to be girls.” It then examines the tomboy child’s family relations and a child’s coming of age as a tomboy, along with gender dynamics in Samoan society within the context of social relations. It also explores how fa’afafine and tomboys become trapped in a world of sexuality under the sign of male domination. The chapter concludes by explaining how male dominance in all sexual matters gives rise to a particular asymmetry between fa’afafine and tomboys and how this results in gender inequality.