For adolescent boys living with HIV, an emerging identity as a person living with HIV intersects with the construction of a masculine identity, conceptualised as situated positioning in relation to hegemonic masculinity. The research focus was to identify constructions of young masculinity at the intersection with identity as an HIV positive person, considering the reciprocal influence of masculine identity and emerging HIV positive identities. The concept of hegemonic masculinity was combined with Dialogical Self Theory in conceptualising masculine identity construction as active positioning. Visual methods (autophotography, biographical drawings and reflective interviews) were combined with semi-structured interviews and focus groups within an interpretive paradigm. Participants were all adolescent boys enlisted from an HIV support group, forming a purposive sample (N=7). Mixed data analysis methods highlighted the active dialoguing of situated masculine identity positions against hegemonic masculinities. Analysis revealed the complex processes of positioning a viable masculine identity in challenging contexts of health, spatial contexts, material conditions and hegemonic imperatives. The findings were potentially relevant for practice and policy promoting of gender equality and gender-equitable masculinities, such as participatory research and gender- based interventions.