Technological advances have contributed to the changing structure and organisation of sex work, heralding a dramatic growth in sex workers soliciting and advertising the selling of sex via the Internet. This study was concerned with four distinctive, independent online escort markets—male heterosexual, female heterosexual, gay and lesbian. A discourse analysis was conducted on ten online advertisements from each escort sample, in order to analyse how different online escorts advertise their sexual services in relation to gender, sexuality and social class. The findings reveal core differences between each of the escort samples in relation to gender and power dynamics. Findings highlighted that maleness and masculinity-as-power play a role whether we are looking at men as the buyers or the sellers of escort services. In stark contrast, advertisements presented femaleness and femininity as objectified, submissive and/or vulnerable regardless as to whether we are looking at women as the buyers or the sellers of escort services.