Masculinities and male privilege may be experienced differently by individuals depending on their intersecting identities, including identities related to gender, race, and sexuality. Trans masculine individuals in the United States may be important informants about the experience of male privilege because their unique psychosocial experiences and gender identity development in a patriarchal society allow observation, insight, and critical reflection not available to cisgender people. Using a standpoint theoretical framework, we explored the lived experiences of male privilege as described by trans masculine individuals (N = 227, M = 26.97, SD = 6.90) who responded to an open-ended prompt on a larger online survey. Using thematic analysis, the research team identified five themes that summarized participants’ perceptions: (a) I feel safer; (b) I am assumed to be competent; (c) I am free of traditional female gender role expectations; (d) I am “one of the boys”; and (e) I don’t experience male privilege. Participants’ attributed their experiences to others’ perceptions of their masculine appearance, gender expression, and gender role performance. These experiences involved psychosocial costs as well as benefits, most notably changes in relationships with women and important communities of support. Some participants noted that their other marginalized identities such as race and sexuality attenuated their experiences of male privilege. Together these findings illustrate the social construction of masculinities and male privilege in everyday interactions while further disentangling these concepts from essentialist assumptions of a biologically based gender binary.