eWhoring is the term used by offenders to refer to a type of online fraud in which cybersexual encounters are simulated for financial gain. Perpetrators use social engineering techniques to impersonate young women in online communities, e.g., chat or social networking sites. They engage potential customers in conversation with the aim of selling misleading sexual material – mostly photographs and interactive video shows – illicitly compiled from third-party sites. eWhoring is a popular topic in underground communities, with forums acting as a gateway into offending. Users not only share knowledge and tutorials, but also trade in goods and services, such as packs of images and videos. In this paper, we present a processing pipeline to quantitatively analyse various aspects of eWhoring. Our pipeline integrates multiple tools to crawl, annotate, and classify material in a semi-automatic way. It builds in precautions to safeguard against significant ethical issues, such as avoiding the researchers’ exposure to pornographic material, and legal concerns, which were justified as some of the images were classified as child exploitation material. We use it to perform a longitudinal measurement of eWhoring activities in 10 specialised underground forums from 2008 to 2019. Our study focuses on three of the main eWhoring components: (i) the acquisition and provenance of images; (ii) the financial profits and monetisation techniques; and (iii) a social network analysis of the offenders, including their relationships, interests, and pathways before and after engaging in this fraudulent activity. We provide recommendations, including potential intervention approaches.