Empirical research exploring the physical health of female sex workers and their risk of contracting and spreading sexually transmitted infections has been over-researched. There have also been numerous studies conducted on sex workers highlighting physical violence, rape and stigmatisation. There is, however, little empirical evidence exploring the personal lives of female sex workers especially with regards to their husbands and the impact that their wives choice in career may have on the constructions of their masculinity. Accordingly, this research aimed to qualitatively explore and understand, via a comparative in-depth case study with two married couples, how the masculinity of a man, who is married to a high-income female sex worker, may be constructed, as compared to a man who is married to a woman who is not involved in the sex industry. It was found, after conducting semi-structured, one-on-one interviews with each of the married couples, that the males constructed their masculinity in relation to their wives occupation, their income in comparison to that of their wives, their wives sexuality, familial and historical notions regarding infidelity, certainty regarding paternity, and issues of romantic jealousy (both sexual and emotional). It was found that, at least for the man from a non-traditional marriage (where his wife was a FSW), by constructing and reconstructing one’s masculinity (when faced with perceived threats regarding one's sense of masculinity), one is able to reclaim the typical patriarchal characteristics. This is done by strongly conforming (and potentially overcompensating by doing so) to traditional masculine and social patriarchal standards and/or by constructing one’s masculinity to align with a more liberal feminist perspective. Therefore one demonstrates a contemporary appreciation of gender equality and non-traditional gender roles for one’s female partner.