When sexuality educators bother to think about gay anal sex, it is usually to consider, 'What can we -- or should we -- teach about it?' Rarely is the question asked, 'What might gay anal sex teach sexuality education?' Inspired by Kathleen Quinlivan's suggestion that we work together to 'create new possibilities for what else sexuality and relationships education could become', this paper explores the educative potential of the anally penetrated male. By engaging with the work of the Indigenous philosopher of education Carl Mika, while attending to a scene of gay anal sex in Witi Ihimaera's novel "The Uncle's Story" (2000), it seeks to expose notions of wellbeing -- commonly conceptualised within sexuality and relationships education in Aotearoa New Zealand as "hauora" -- to the destabilising metaphysical entities of darkness and nothingness, thereby opening sexuality education up to what Mika calls the '(il)logic of mystery'.