From the Indian Supreme Court ruling on Transgender Rights in 2014 to the passing of the transgender Persons (Protection of Rights) Act 2019, the last decade has been crucial for the transgender community in India. However, a closer look at the lives of transgender/gender-non-conforming individuals continues to portray an image of violence, violation of human rights, discrimination, and marginalization. This study describes the lived experiences of two Indian transgender, non-confirming individuals who sought gender-affirmative procedures. The study specifically focused on genderqueer or non-binary individuals who fell beyond the neat categories of “man” and “woman.” The nature of the study was exploratory and semi-structured interviews were employed to collect in-depth data, analyzed through the interpretative phenomenological analysis (IPA) framework. Key findings showed limited family acceptance, binarized gender ideas, monogendering, threats to safety, and medical barriers to characterize the gender journeys of the interviewees. Both participants considered their gender-affirming surgeries as imperative to their well-being. The participants considered parental support, accepting peers, and responsive, queer-friendly medical practitioners to be positive influences. The study indicates that sensitizing health practitioners, working with parents, and creating affirmative spaces, especially in schools and workplaces, can significantly improve mental as well as physical health outcomes for transgender, non-confirming individuals. Implications for social work are discussed.