The nature of sex work changes over time for many reasons. In recent decades around the world, there has been movement toward legalization and control of sex economies. Studies of the possible impact of legalization mainly have focused on sexually transmitted infections and violence, with little attention to change in the diversity of sexual services provided. This study examined the practices of sex workers before and after legalization of prostitution. Cross-sectional surveys of comparable samples of female sex workers were conducted in 1991 (N = 200, aged 16–46 years) and 2003 (N = 247, aged 18–57 years) in Queensland, Australia, spanning a period of major change in regulation of the local industry. In 2003, male clients at brothels and private sole operators (N = 161; aged 19–72 years) were also interviewed. Over time, there was a clear increase in the provision of “exotic” sexual services, including bondage and discipline, submission, fantasy, use of sex toys, golden showers, fisting, and lesbian double acts, while “traditional” services mostly remained at similar levels (with substantial decrease in oral sex without a condom). Based on comparisons of self-reports of clients and workers, the demand for anal intercourse, anal play, and urination during sex apparently exceeded supply, especially in licensed brothels. Within this population, legalization of sex work coincided with a substantial increase in diversity of services, but it appears that in the regulated working environments, clients who prefer high risk practices might not dictate what is available to them.