This study aimed to examine the pathways from child sexual abuse to sexual assault victimization and perpetration in adolescence and early adulthood, considering risky sexual behavior and lowered sexual self-esteem as mediator variables. In a two-wave longitudinal study with 2251 college students in Germany, male and female participants provided reports of sexual aggression victimization and perpetration since age 14 (T1) and again a year later (T2), covering the last 12 months. In addition, child sexual abuse (CSA; before the age of 14), risky sexual behavior, and sexual self-esteem were assessed at T1, and risky sexual behavior and sexual-self-esteem were assessed again at T2. Experience of CSA was significantly associated with greater likelihood of sexual aggression victimization and perpetration, lower sexual self-esteem, and more risky sexual behavior in both gender groups at T1 and was directly related to victimization at T2 among male participants. In both gender groups, CSA indirectly contributed to a higher probability of sexual victimization at T2 via its impact on victimization T1. In males, the indirect path from CSA to T2 perpetration via T1 perpetration was also significant. Through its negative impact on sexual self-esteem, CSA indirectly increased the probability of sexual victimization among women and the probability of sexual aggression perpetration among men. Risky sexual behavior mediated the pathway from CSA to sexual victimization at T2 for men and women and the pathway from CSA to sexual aggression perpetration for women. The findings contribute to the understanding of gendered effects of CSA on revictimization and the victim-to-perpetrator cycle.