Women who engage in transactional sex are not only at increased risk of HIV and intimate partner violence, but also face social risks including gossip and ostracism. These social and physical risks may be dependent on both what a woman expects and needs from her partner and how her community perceives the relationship. Gender theory suggests that some of these social risks may hinge on whether or not a woman's relationship threatens dominant masculinity. We conducted a qualitative study in Swaziland from September 2013 to October 2014 to explore transactional sex and respectable femininity through the lens of hegemonic gender theory. Using cultural consensus modeling, we identified cultural models of transactional sex and conducted 16 in-depth interviews with model key informants and 3 focus group discussions, for a total of 41 participants. We identified 4 main models of transactional relationships: One typified by marriage and high social respectability, a second in which women aspire towards marriage, a third particular to University students, and a fourth "sugar daddy" model. Women in all models expected and received significant financial support from their male partners. However, women in less respectable relationships risked social censure and stigma if they were discovered, in part because aspects of their relationship threatened hegemonic masculinity. Conversely, women who received male support in respectable relationships had to carefully select HIV risk reduction strategies that did not threaten their relationship and associated social status. Research and programming efforts typically focus only on the less socially respectable forms of transactional sex. This risks reinforcing stigma for women in relationships that are already considered socially unacceptable while ignoring the unique HIV risks faced by women in more respectable relationships.