While the disproportionate impact of HIV on young black men who have sex with men (MSM) is well documented, the reasons for this disparity remain less clear. Through in-depth interviews, we explored the role of familial, religious, and community influence on the experiences of young black MSM and identified strategies that these young men use to negotiate and manage their sexual minority status. Between February and April 2008, 16 interviews were conducted among HIV-infected and HIV-uninfected young (19- to 24-year-old) black MSM in the Jackson, Mississippi, area. Results suggest that overall, homosexuality remains highly stigmatized by the men's families, religious community, and the African American community. To manage this stigma, many of the participants engaged in a process of “role flexing,” in which individuals modified their behavior in order to adapt to a particular situation. The data also provided evidence of internalized homophobia among a number of the participants. The impact of stigma on risk behavior should be more fully explored, and future intervention efforts need to explicitly address and challenge stigma, both among young men themselves and the communities in which they reside. Attention should also be paid to the role masculinity may play as a driver of the HIV epidemic among young black MSM and how this knowledge can be used to inform prevention efforts.