Cycling has always been popular in China, especially during the years when the government encouraged green travel. Many people participate in rides to ease traffic congestion and increase transfer convenience. Due to the disorganized and tidal nature of cycling, cyclists create many conflicts with other groups. Adolescents are vulnerable road users with a strong curiosity and risk-taking mindset. Identifying the factors influencing adolescents’ aggressive riding behavior can assist in developing strategies to prevent this behavior. An online questionnaire was used to collect data on bicycling among students in a middle school in Guangzhou, China. The theory of planned behavior (TPB) and prototype willingness model (PWM) have been applied to study travel behavior and adolescent risk behavior. To investigate the impact of psychological variables on adolescent aggressive behavior, we used TPB, PWM, TPB + PWM, and an integrated model. Behavioral intentions are greatly influenced by attitudes, subjective norms, and perceived behavioral control. Both descriptive and moral norms played a role in behavioral willingness. The integrated model explained 18.3% more behavioral variance than the TPB model. The social reactive pathway explained more variance in behavior than the rational path.