The present study examined indirect over-time relations between parenting and adolescent sexuality through global self-esteem. Three waves of online questionnaire data were collected among a community sample of 1,116 Dutch adolescents (M = 13.9 years at baseline). Participants rated the quality of their relationship with parents, their global self-esteem, and their experience with various sexual behaviors. Sexually experienced adolescents (n = 168) evaluated their sexual experiences using six emotions. Path model results showed that a higher-quality relationship with parents at T1 predicted higher levels of self-esteem at T2, which in turn predicted less experience with sexual behaviors and more positive sexual emotions at T3. The indirect over-time path from relationship quality through self-esteem to adolescents’ sexual emotions was significant; the indirect path to adolescents’ experience with sexual behaviors was not significant at the .05 level. No significant age or gender differences were found in the path models. The findings indicate that self-esteem plays an important role in adolescent sexuality and that parents can contribute to positive sexual experiences of adolescents indirectly—through the enhancement of self-esteem—by fostering a high-quality relationship with their children. Implications for theory, future research, and strategies to promote healthy and positive youth sexuality are discussed.