In contrast to victimization, prior research on the antecedents and outcomes of bullying perpetration has provided little conclusive knowledge. Some adolescent bullies may be well adjusted and popular among peers, while other bullies are rejected and lack self-control. There is also great variation in the outcomes, with a number of studies (but not all) showing increased risk for externalizing and internalizing problems. We used a developmental framework and data from 2,230 participants of the Dutch Tracking Adolescents' Individual Lives Survey (TRAILS) to examine bullying perpetration across adolescence, to test the links with various antecedents in preadolescence, and to elucidate the outcomes in early adulthood. Latent growth models indicated significant variance in initial bullying perpetration levels and an overall decrease between pre- and late adolescence. Individual, family, and peer factors were associated with initial levels and partially associated with bullying development over time. Bullying perpetration was linked to later maladjustment and substance use, although only in girls. Finally, bullying perpetration appears to function as an intermediate variable between preadolescent individual, family, and peer risk and substance use more than 10 years later. These results have important implications for understanding the gender-specific nature of bullying perpetration and its outcomes and for demonstrating that bullying carries early risk into adulthood.