Boys have long been positioned as marginalised participants in the education system, where categorical notions of boys as failing and girls as achieving persist. These ideas have played out strongly in western societies in the areas of literacy and reading, with a convergence of boys and literacy 'crises'. While it has been documented that some boys underperform in reading ability when compared to some girls, essentialist notions of gender fail to consider the way achievement is not simply based on sex. Drawing on Bourdieu's concept of habitus, specifically a literate habitus (Carrington & Luke, 1997), this article analyses two websites created to promote reading for middle-school boys. It considers how these sites contribute to and perpetuate constructions of hegemonic masculinities. Focusing on the websites as promoting 'boy-friendly' literacy interventions, the text-based analysis considers the ways particular constructions of masculinity are represented and why this may be problematic in terms of our work with middle-school boys.