Situated in Hong Kong's considerably limited discourse on sexuality, this paper aims to examine how introducing the topic of masturbation into our college's gender-and sexuality-related course created pedagogical conundrums (in the words of Kathleen Quinlivan). We discuss how attempts to confront these conundrums enabled us to begin the journey of understanding and breakthe silence about having sexual desire discussed in the classroom and written assignments. Drawing on our earlier classroom discussion of sexual topics, which resulted in moments of silence, and the written assignments of 10 students on the topic of masturbation, this paper borrows Quinlivan's discussion of the possibilities in 'uncomfortable analytic reflexivity' to explore how education can be a highly contested space carved out by students to express, both 'silently' and 'openly', their perceptions of masturbation. Classrooms can be flipped to discover the cracks that allow the journey towards breaking the silence to begin and to provide space for students to discuss sexual desires and pleasures that were previously deemed negative and unspeakable in their previous classroom experience. Remembering and reflecting on such silence can allow it to be reconceptualised as illuminating and meaningful.