While the international scientific community recognizes the importance of Comprehensive Sexuality Education (CSE) as an integrated approach to sexuality education, the Italian context is characterized by a complex interplay of cultural and political factors that hinder its widespread and structured implementation. Drawing on a theoretical framework that combines CSE and transfeminist pedagogy, this article explores the perspectives of twelve secondary school teachers actively engaged in promoting access to sexuality education. The study highlights how school contexts are shaped by structural tensions, showing that the implementation of sexuality education is constrained by an institutional climate perceived as hostile. At the same time, strategies of resistance and negotiation emerge, contributing to the preservation of educational spaces oriented toward care, critical reflexivity, and the recognition of differences. The study offers a situated account of teachers’ experiences and contributes to a still limited but increasingly urgent debate on sexuality education within the Italian school system.