In the Philippines, transgender women have been identified as ‘bakla’ and recently as ‘transpinays’. This chapter examines the cultural situations and experiences of the transpinay within the conflated identities called ‘bakla’ in the school and social context of the Philippines, based on the concept of transphobia and the minority stress model. This lexical and conceptual conflation has, perhaps, contributed to their misconstrued visibility and marginalization in Philippine society, beginning during their formal education and trailing them throughout their lifetimes. Using some of the narratives from the author’s 2006 and 2012 case study theses, the author explored the life experiences of 15 transpinays, focusing on how they learned about their gender identities, how school affected these identities and how they thrive in a society that moralizes and pathologizes gender freedom. Recommendations and implications for the government and schools in the Philippines to support transgender students are discussed.