This article analyzes how individuals use affect as a resource to negotiate judgments of appropriateness in situations where they or others feel sexualized. It draws from two years of participant observation at a sensual figure drawing session in an erotic arts club—where bodily exposure was heightened and social norms regarding sexualization were ambiguous—as well as in-depth interviews with the club’s artists, models, and owners. It argues that somatic security and somatic insecurity, individuals’ comfort or unease with how they perceive others to interact with their bodies through talk and bodily comportment, mediate sexualized interactions. Extending sociological studies of sexualization in interaction, it reveals that these affective states, which arise out of situational dynamics, form a foundation of comfort/unease toward others and assurance/shame with oneself. Individuals use these affective experiences to judge and justify future interactions as appropriate or inappropriate and develop relationships with others.