This qualitative investigation explored the experiences and contexts of stigma and discrimination among HIV-positive and high-risk kothi-identified men who have sex with men (MSM) in Chennai, India, and ramifications for HIV prevention. MSM were recruited through community agencies (n = 10) and public sex environments (n = 8), along with three key informants. In-depth, semistructured interviews were conducted, audiotaped, and transcribed. Narrative thematic analysis and a constant comparative method were used to identify themes. Findings revealed multiple intersecting social and institutional contexts and experiences of stigmatization, discrimination, and violence across police, community, family, and health care systems, as well as illuminating consequences for MSM. Multisystemic structural violence places kothis at extreme vulnerability for HIV infection and AIDS. Public mass media antidiscrimination campaigns, education and training of health care providers and police, funding of indigenous MSM community organizations, and decriminalization of consensual sex between same-sex adults may help to combat stigma, discrimination, and violence against MSM, which is fundamental to effective HIV prevention.