Boys' relationships at school produce and regulate masculinities with male peer group cultures often, although not always, providing oppressive contexts that seek to establish narrow boundaries around what is considered acceptable 'boy' behavior. This paper explores how different groups of primary school boys' position reading within their masculine identify and the influence of immediate and broader contextual environments on such positioning. To examine such contexts, this paper draws on qualitative research that represents the reading experiences of primary school boys from seven schools located in a range of socio-economic communities in South East Queensland. The boys' narratives are located within broader ecological environments making visible differences between groups of boys and building on research into literacy in situ, how it is acquired, and mediated, within particular social and cultural contexts. The work of Bronfenbrenner (1979) informs how the paper understands the complex and multiplicity of environmental influences on both reading experiences and notions of masculinities from an ecological approach. That is, rather than isolating literacy experiences from other daily practice, an ecological approach facilitates understanding of how attitudes towards reading are embedded in boys' social life, thought, and in learning. To present the intricacies involved in reading interactions, the narratives offered by the boys within the domain of their experience at school (microsystem) are embedded within their perceptions of parental views about reading (mesosystem), the socioeconomic location of the school (exosystem), and their interpretations of reading as valued knowledge in wider societal spaces, such as workplace trajectories (macrosystem). With the utility of this ecological approach in mind, the paper presents findings indicating that the underperformance of some boys in reading is influenced by particular attitudes and actions that boys internalise through their everyday social interactions that contribute enabling and constraining influences on reading attitudes, reading frequency and subsequently performance. The paper then considers the problematics of particular notions of masculinities on attitudes towards reading and the possibilities of initiatives that challenge culturally and socially constructed understandings of masculinity through pedagogical reforms rather than reinforcing simplistic notions of masculinity through a boy-friendly environment.