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1. Introduction The evolution of the commercial internet was accompanied by a rapid expansion of the online adult industry. While explicit content involving adults was legally regulated, a gray area emerged in the early 2000s involving websites dedicated to "teen models." These sites, often operating legally by avoiding nudity, featured minors—sometimes as young as 13—in swimsuits, lingerie, or provocative poses. This paper explores the "teen modeling" niche as a case study in technological determinism and regulatory failure. It argues that the industry was designed specifically to push the boundaries of child protection laws, contributing to the normalization of the sexualization of minors online.