Transmasculinity is a nonnormative gender category that resists gender polarization and fixation on identities. Transmen, as female-to-male transgender people, exist across all demographics and cultural boundaries. They are identified as female at birth because of their anatomy, but they express themselves closer to traditional masculine gender roles as they grow. Their gender expressions defy cultural sexism, hence creating ambivalence in the structure of conventional gender binaries. Some undergo surgeries and hormonal therapies to look more masculine and enter the arena of gender confirmation. The existence of transmen like transwomen can dismantle the idea that there is a correct way to dress, speak, feel, and behave to appear normal in the gender spectrum. Transmen are relatively invisible in India, and so their untold tales as compared to the Western world. Their voice and presence are appropriated by the hegemony present in alternate-gender communities. The present study is an informed analysis of multiple challenges faced by female-to-male transgender people in India. It offers a unique insight into their experiences, ranging from encountering social stereotypes and stigma to family pressure, the process of sexual transitioning, and the threat and gender violence they face in the cisgender social infrastructure. The chapter focuses on the narratives about transmen of India, whose affairs are a mere addendum to the experiences of other transgender people through the reading of A. Revathi’s (2016) A Life in Trans Activism and Nandini Krishnan’s Invisible Men: Inside India’s Transmasculine Network (2018). Besides that, interview clippings, short poems, and articles will also be used to unravel the diverse experiences of the transmen community, which will defy erasure, misappropriation, and the “historical a priori.” The stories of transmen will help in reshaping the discourse around masculinity and interrogate the notion of masculinity and gender conformity.