One main source of sexual socialization lies within family interactions. Especially sexuality-specific parenting may determine adolescents’ sexual development—adolescents’ sexual behavior and sexual risk behavior, sexualized media consumption and permissive sexual attitudes—to a significant extent, but different ideas exist about how this works. In this longitudinal study, we examined two hypotheses on how sexuality-specific parenting—parenting aimed specifically at children’s sexual attitudes and behaviors—relates to adolescents’ sexual development. A first buffer hypothesis states that parents’ instructive media discussions with their children—called instructive mediation—buffers the effect of sexualized media consumption on adolescents’ sexual attitudes and behavior and, vice versa, the effect of adolescents’ sexual attitudes and behavior on sexualized media consumption. A second brake hypothesis states that parents, by communicating love-and-respect oriented sexual norms, slow down adolescents’ development toward increased sexualized media use, permissive sexual attitudes, and sexual behavior and sexual risk behavior. Using four-wave longitudinal data from 514 Dutch adolescents aged 13–16 years (49.8% female), we found evidence to support a brake effect. More frequent parental communication of love-and-respect oriented sexual norms was associated with less permissive sexual attitudes and, for boys, with less advanced sexual behavior and a less rapid increase in sexual risk behavior. Parents’ instructive mediation regarding adolescents’ sexualized media consumption was associated with less permissive sexual attitudes at baseline, but only for girls. No systematic evidence emerged for a buffer effect of parents’ instructive mediation. In conclusion, although our data seem to suggest that parent–child communication about sex is oftentimes “after the fact”, we also find that more directive parental communication that conveys love-and-respect oriented sexual norms brake adolescents’ move toward sexual maturity.