This article focuses on the little known phenomenon of heterosexual men’s participation in gay¹ sport clubs. It explores the relationship between straight men joining gay teams in a context of changing masculinities. Through 12 interviews with a diverse range of self-identified straight men living in the UK, the research demonstrates how traditional definitions of masculinity are possibly shifting, as are their attitudes towards sexuality, as a result of their involvement with gay sport organisations. Their experiences and stories reveal how their participation in gay sport settings may contribute to diminished cultural homophobia, in line with other recent studies. Initial stereotypes and perceptions of gay athletes were dismantled, resulting in clear attitudinal shifts toward homosexuality. The men interviewed had no one single conceptualisation of masculinity, and instead showed a more pluralised and inclusive version of masculinity. While their participation in gay clubs can largely be seen as a positive and transgressive act, their involvement still has some limitations.