STIs are affecting youth at an alarming rate. The majority of these diagnoses are found in females. Poor decision making has been examined as a mechanism underlying STI risk behavior, but research has been limited. The present study examined the association between discounting and STI risk behavior, including drug use, in youth (N = 155), ages 14-21 years. Further the study included a psychometric examination of the Sexual Discounting Task (SDT) with regard to STI risk behavior. The SDT should be considered a clinically meaningful assessment of STI risk behavior in youth. Sexual discounting had robust associations with STI risk and differences were found across gender. Further, differences in gender, sexual discounting, and STI risk were found across drug users. In addition, STI risk differences were by gender and across drug users. The results highlight discounting as a critical and fairly unrecognized variable for understanding STI engagement, especially in females and drug users, which may benefit current STI intervention and prevention strategies.