<p>This study utilized a positive deviance approach to explore both parental and adolescent factors that influence protective sexual behaviors (PSBs)—specifically sexual abstinence and safer sex practices—among secondary school students in Osun State, Nigeria. A cross-sectional survey of 1,283 adolescents aged 14 to 19 was conducted in eight secondary schools using multistage random sampling. Protective sexual behaviors were classified using Cort and Tu’s risk continuum model. Multinomial logistic regression was applied to analyze the data, guided by an adapted integrative theoretical framework. Two models were developed: the first examined parenting-related factors, including sexual and reproductive health (SRH) communication, parental support, and monitoring; the second model assessed adolescent-level variables, including sexual attitudes, peer norms, SRH knowledge, and religiosity. Sociodemographic characteristics were adjusted for in both models. Study findings revealed that adolescents reporting higher levels of parental monitoring and support demonstrated a greater likelihood of practicing abstinence or engaging in safer sex. At the individual level, adolescents with higher religious commitment and better SRH knowledge were more likely to adopt safer sexual behaviors. In contrast, permissive sexual attitudes and exposure to risky peer norms significantly increased sexual risk. A contextually salient finding of the current study was that female adolescents were disproportionately represented in the highest-risk category featuring inconsistent condom use and lack of sexual fidelity. This study highlights that a combination of open and supportive parenting, and informed choices shapes protective sexual behaviors among adolescents. Viewing adolescent sexuality through a strengths-based and context-aware lens can improve public health strategies.</p>