The "sexual trajectory" is an age-graded set of various new sexual experiences, defined by three key dimensions: sequence, duration, and timing. A comprehensive description of sexual trajectories creates the possibility to investigate potential risks of certain trajectory types. The present study attempted to answer three questions: (1) Is it possible to identify a typology in (the early stages of) sexual trajectories? (2) Is sexual trajectory type related to demographic characteristics, such as sex, ethnic background, and educational level? (3) What are the associations between sexual trajectory type and recent sexual risk behavior? A representative Dutch sample of 1,263 males and 1,353 females (M = 20.46 years; range, 12-25) who had engaged in sexual intercourse completed a questionnaire about sexual (health) behavior. About three quarters of participants followed a progressive sexual trajectory from less intimate (e.g., kissing) to more intimate behavior (e.g., sexual intercourse). Immigrant groups and less educated youth were more likely to follow a nonlinear trajectory. A progressive trajectory was associated with a higher likelihood of consistent contraceptive use with the most recent partner and, for girls, with a lower likelihood of having unprotected anal intercourse with the last partner. It was hypothesized that the nonlinear trajectory could be ascribed to a lack of opportunities or skills to plan and steer early sexual experiences and that these limitations were fairly stable over time. Sexual education should aim at providing adolescents with sufficient (self) knowledge and skills to construct their sexual trajectories according to their own wishes or needs.