In two pre-registered experiments with German samples, we tested the role of endorsement of the Madonna-whore-dichotomy and the relationship context (sex in a committed relationship vs. casual sex) in the devaluation of women’s sexual pleasure. Using the context of dating apps in Study 1, men who reported higher endorsement of the Madonna-whore-dichotomy believed that other men would be less interested in fulfilling a woman’s sexual desires, show her less respect, and be less likely to wear a condom independent of relationship context (i.e., casual hookup dating app vs. a dating app for a serious relationship). In Study 2, men who reported higher endorsement of the Madonna-whore-dichotomy rated their partner as less entitled to sexual pleasure than men lower on Madonna-whore dichotomy endorsement. In addition, women who reported higher endorsement of the Madonna-whore dichotomy devalued their own pleasure by rating their partner as more entitled to sexual pleasure than themselves, compared to those lower on the Madonna-whore dichotomy. Although relationship context and Madonna-whore dichotomy endorsement did not interact, they were both found to negatively predict women’s sexual pleasure. These results provide further support for the potential costs of enacting traditional, patriarchal gender roles for women’s experiences of sexual pleasure and safety.