Evidence suggests that transgender female youth (TFY), much like their adult transgender female peers, are at high risk for HIV. Yet little attention has been given to important developmental experiences of TFY that may impact HIV risk for this youth population. The overall purpose of this study was to explore HIV risk in TFY. A reoccurring theme from the qualitative data was the importance of parents. To better understand the impact of parents on HIV risk among TFY, in-depth individual interview data from 21 TFY in Los Angeles and Chicago were analyzed, suggesting a potential link between HIV-related risk behavior and parental support. Youth with parental support in this sample reported regular condom use, while those without such support reported inconsistent condom use. Implications for the unique research and interventions needs of TFY related to parental support and sexual risk behaviors are discussed.