This chapter explores the complex, overlapping motivations behind teenage boys’ engagement in sexting, emphasising that these motivations are not singular but intersectional. These behaviours exist on a continuum from socially accepted adolescent expression to deviant acts, depending on context, consent, and community norms. Traditional educational approaches fail to address adolescent sexting, especially when driven by sensation-seeking and impulsivity. Simply condemning sexting reinforces control over sexual agency and ignores the nuanced, consensual experiences of teens. Approaches to education that conflate experimental and aggravated sexting, distort adolescent realities. An inclusive, critical RSE curricula that embrace diverse sexual discourses and promote ethical, informed decision-making through digital sexual literacy aligns with a call for sex education that reflects young people’s lived experiences.