Physical education's role in the production of boys' gender identities has become a critical topic among educational researchers, yet most inquiries rely on methodologies where adult men reflect on their experiences as young boys (e.g., Drummond, 2003). Almost no studies have specifically examined adolescent boys' gender socialization as it occurs, despite our realization of the ultra-masculine nature of most physical education contexts. Purpose: Therefore, the purpose of this study was twofold, first, to understand boys' gender identities and the role that physical education plays in their development, and, second, to explore methodological techniques when researching sensitive topics with adolescent boys. Methods: Guided by poststructural feminism (Lather, 1991: Oliver, in press: Azzarito, 2006), we worked with five middle school boys (2 in grade seven & 3 in grade eight; 4 White & 1 Asian American) from two suburban schools in the Midwestern US. We collected data during one-hour sessions, twice a week for thirteen-weeks using student-centered methodological approaches including observations, conversations, journals, drawings, writing activities, and games. We audio-recorded all sessions and transcribed them. In addition, we recorded fieldnotes and collected all student work (e.g., journals, drawings, etc.). We conducted thematic analysis using constant comparison and analytic induction, and sought trustworthiness through a researcher journal, triangulation, and peer debriefer. Analysis/Results: In working with these boys, we identified two overarching themes. First, we found that discourses of masculinity, both in physical education and beyond, inundate boys from many sources (visual, spoken, written) and play a significant role in shaping how they understand themselves and their place in social life. Boys feel their identities under constant threat in ultra-masculine contexts like school physical education, especially boys whose embodiment contradicts dominant ideologies of masculinity. Second, we found that any efforts to understand how various contexts influence adolescent boys' gender identities must employ identity-safe methodologies because of the central, emotional, and risky connections between masculinity and identity. Safe spaces methodologies include: recruitment practices, geographic spaces, transitions, modes of inquiry, and group dynamics. Conclusions: This work has direct implications for practitioners and researchers. Practitioners must understand how their practices (both intentional and unintentional) either reproduce or resist dominant masculinity discourses in adolescent boys, given its central place in their lives and processes of identity development. Researchers working with adolescent boys must understand boy how important interpreting, conforming and resisting dominant discourses of masculinity is for boys and employ safe, in-depth inquiries. Keyword(s): gender issues, research