Taking a view of identity as discoursal participation in figured worlds, this chapter draws upon data collected during a longitudinal, small-scale research project exploring the relationship between creative writing and boys’ identities as they make the transition from primary to secondary school. Creative writing from six of the boys is analysed using discourse analysis and the ways in which the creative text can create hybrid discourses which disrupt hegemonic masculinity Connell 2005 are identified. This radical potential for boys to enact different identities through creative writing is seen as being related to the pedagogy adopted by the teacher. Accordingly, an argument is made: against a backdrop of a neoconservative curriculum and neoliberalism’s state controlled de-control, it is only through pedagogies which involve weaker framing and choice that boys can realise other ways of being.