This study explored how gender expressions were portrayed in the narratives of gay men who view themselves as non-masculine. An adapted life story interview was conducted with seven participants between the ages of 20 and 47 years. Life stories were analysed using content analysis. The study found that non-masculinity was defined in different ways and that social context, including threat, impacted on gender expression. Non-masculinity was strongly associated with male homosexuality. Homophobic verbal and physical abuse was portrayed alongside negative appraisals of non-masculinity. This may be indicative of internalised anti-effeminacy values. Marginalisation in gay communities was also portrayed, including romantic rejection. Intersections of gender-expression and ethnicity or age were important in evaluations of sexual attractiveness. Conversely, masculinity was often eroticised or regarded as aspirational. Positive qualities associated with non-masculinity included expressiveness, humour and flexibility in working with power demonstrations of others. These reinforce the assertion that effeminate and androgynous men bypass facets of gender-role conflict.