Sexually explicit media may perpetuate racial and sexual norms among men who have sex with men. While men may be exposed to sexually explicit media in the online settings where they seek sex with other men, no studies to our knowledge have explored the relationship between the racial and sexual content of advertisements appearing in these spaces. In 2011, 217 sexually explicit advertisements on a male sex-seeking website were coded for themes, actor characteristics, and sexual acts depicted using a detailed codebook. Multivariable logistic regression models examined the association between skin colour, theme, sexual acts, and condomless sex acts. Nearly half (45%) featured a ‘thug’ theme (style emphasising Black masculinity/hip-hop culture), 21% featured a college theme, and 44% featured condomless sex. Ads featuring only Black men, ads featuring Black men with men of other skin tones, and ads depicting a thug theme were positively associated with depictions of condomless sex. Online sexually explicit ads featuring Black themes and actors more frequently depicted risky sex than ads with White men alone. Future research should examine whether risky depictions of Black men in online ads influence the sexual norms and cognitions of Black men who have sex with men and their partners.