Transgender identities are becoming increasingly common in the United States, and existing research provides ample evidence that risky sexual behaviors, substance use, and suicidality are prevalent experiences among transgender persons. Yet, prior research provides little insight into understanding the specific mechanisms that may promote deviant outcomes among transgender persons. Drawing from an aspect of general strain theory, the goal of this study is to examine the extent to which transwomen and transmen vary in risky sexual behaviors, substance use, and suicidality, and to explore the degree to which discrimination - as a source of strain - plays a role within this process. An analysis of data from transgender individuals from the Virginia Transgender Health Initiative Study (THIS) demonstrates that transwomen and transmen significantly diverge in self-reported risky sexual behaviors, substance use, and suicidality. Greater discrimination based on transgender identity relates to significantly increased odds of suicidality and elevated levels of substance use, but does not relate to risky sexual behavior. Overall, effects of discrimination on each outcome are similar for both transwomen and transmen.