Sexual self-disclosure (SSD) is when a person shares information about their sexuality with another person. Technology-mediated communication is pervasive in modern society, yet researchers have not distinguished between SSDs that occur in-person versus in technology-mediated contexts. Using the Interpersonal Exchange Model of Sexual Satisfaction, researchers previously found that SSD predicts sexual rewards, costs, and satisfaction. In this study, we (1) compared cisgender/transgender men’s and women’s frequency (how much) and breadth (how many topics) of SSD via typed technology and in-person (H1, H2), and (2) examined the extent to which the frequency and breadth of SSD in each context predicted perceived sexual rewards, comparison of sexual rewards, and in turn sexual satisfaction while controlling for relationship satisfaction (H3, H4, H5, H6). Undergraduate students (N = 450) completed an online survey that assessed SSD in each context, perceived sexual rewards and costs, comparison of own and partner’s sexual rewards and costs, and sexual and relationship satisfaction. Participants reported more frequent and greater breadth of SSD in-person than via technology. We also found that women disclosed more sexual topics than men in-person but not through typed technology. Using path analyses, a greater frequency of SSD in-person predicted greater perceived sexual rewards and comparison sexual rewards, and in turn, greater sexual satisfaction. The frequency of SSD via typed technology and the SSD breadth in either context did not predict exchanges or sexual satisfaction.