This paper explores how Australian gay men experience gender and sexuality in relation to heteronormative gender norms, specifically masculinity. A sample of 32 gay men 22–72 years of age participated in an online interview, using a videoconferencing software, on masculinity and homosexuality. Thematic analyses revealed that gay men experience gender and sexuality-related strain across all levels of their socioecological environment through social regulation, homophobic discrimination/harassment, and anti-effeminacy prejudice. The gay men expressed feelings of self-loathing, shame, internalized homonegativity, and isolation as a result. In examining interactions at each level of the socioecological environment, future research and practice may gain understanding in the social phenomena and how to ameliorate such strain.