<p>Feminist-inspired theorizing is abundant in the literature on sex work, but most other scholarship in this field is empirical and based on single-case studies. This article presents a different kind of theory based on systematic comparison of distinct types of sex work. Drawing on the empirical literature, I argue that sector-specific structural and interactional characteristics can be linked to corresponding patterns in participants’ routine experiences and meanings. Some of the principal meanings revolve around the degree to which a particular sector is favorable to rebranding by the actors involved in it. This is known as norm “neutralization” and “deviance disavowal” in the sociology of deviance. The analysis concludes that the social organization of certain sectors is significantly more favorable to partial normalization than is the case for other sectors. Theorizing the role of key variables in four sex work sectors, I offer an explanation for divergent sectoral capacities and outcomes related to destigmatization.</p>