As awareness of issues faced by transgender individuals increases, many young people have been exposed to a dominant narrative about gender identity. Often these narratives are based on binary constructions about both sexual orientation and gender identity. The lack of diverse, representative cultural narratives has implications for identity development and sexual health. Transgender men who have sex with cisgender men in particular represent an understudied and overlooked population who likely experience unique developmental tasks related to the intersection of socially stigmatised sexual orientation and gender identities. This study explores sexual orientation and gender identity development among a sample of young adult transgender men who have sex with men. In-depth interviews using a modified life history method were conducted with 18 young men. Interview transcripts were coded using open, narrative and focused coding methods. Participants discussed milestones in the development of their sexuality and gender identity that map onto existing models, but also described ways in which these processes overlap and intersect in distinct ways. Findings highlight the need for human development models of sexual orientation and gender identity that integrate multiple identity processes. Implications for future research and practice to increase support for young adult transgender men are discussed.