Positive psychosexual development in adolescence is crucial to sexual health. Evidence suggests that adolescent’s psychosexual development is influenced by the sexual self-concept, relational skills, attitudes toward sexual pleasure, and sexual practices. To date, however, understanding of normative dispositions and experiences that positively shape adolescents’ psychosexual development remains limited. The goal of the study was to provide a descriptive analysis of adolescents’ perceptions of their sexual self, relational skills, and attitudes towards sexual pleasure as well as their sexual practices while considering age and gender differences. A Canadian sample of 1584 adolescents (49.7% girls, 49.4% boys and 0.9% gender diverse) aged 14 to 18 years old (M = 15.53, SD = 0.93) completed a self-reported questionnaire evaluating various aspects of sexuality and sexual practices. Results indicated that most youth are sexually active through autoerotic or partnered sexual practices, and that positive perceptions towards the sexual self, relational capacities and pleasure increase with age. Moreover, compared to girls, boys presented a more positive sexual self-concept, less positive perceptions of their relational skills and they were more likely to report autoerotic sexual practices. Cluster analysis supported classifying adolescents into the following profiles: positive, mildly positive, mildly negative and negative perception of the sexual self and sexuality. These profiles varied according to sexual practices, gender and age. This study provides further insight into general patterns and heterogeneity of adolescents’ sexuality that are relevant for adapting sexuality education and sexual health intervention.