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Research has just begun to study associations between sexual fluidity and health among cisgender individuals; only 1 cross-sectional study examined these links among transgender individuals. The goals of the current study were to prospectively examine fluidity in sexual attractions and fluidity in sexual orientation identity, and associations with health-related outcomes. Participants were a community-based sample of 45 transgender men, ages 16–51 years, who had recently begun testosterone, and 95 cisgender individuals (53 women, 42 men), ages 18–55 years, who completed surveys either in-person or via mail. Analyses tested for group differences in sexual fluidity, sociodemographic predictors of sexual fluidity among transgender men, and associations between sexual fluidity and health across the 3 groups. As hypothesized, transgender men reported more fluidity in sexual attractions and sexual orientation identity than did cisgender individuals. Contrary to our hypotheses, testosterone use was not significantly associated with sexual fluidity, although less education was. As hypothesized, fluidity in sexual orientation identity was associated with more adverse mental health outcomes among transgender men (depression and anxiety) and cisgender women (anxiety and stress), as well as decreased vitality among transgender men and cisgender women, and decreased social functioning among cisgender women. In contrast, fluidity in sexual attractions was only associated with less depression among cisgender women, but was not significantly associated with any other health-related outcomes. This study increases knowledge about sexual fluidity among transgender men and implications for health and can inform clinical work with this population.