Prostitution remains a controversial issue in the United Kingdom. The period of 2000 to 2009 saw a range of disparate solutions, from legalization to abolition, debated by policy makers and feminists and covered extensively in the news media. The debates raised questions about the public's rights, the treatment of prostitution as a legitimate form of work in the liberal economy, the limits on women's choice to enter sex work, and the extent of violence and harm experienced by sex workers. Definitions of prostitution are enacted via a complex relationship between legal and cultural discourses. The media uses certain tropes that create discursive boundaries in the debates. The first principal research question is, "How are competing discourses of prostitution conveyed in contemporary British news media?" The project provides an empirical analysis of the competing constructions of prostitution in British news media over the last decade, focusing on the depiction of sex workers, clients and the phenomenon of prostitution generally. Previous operationalizations of Habermas' theory of communication suggest that it is an effective approach for revealing distortions in media discourses. The study operationalized the validity claims of Truth, Sincerity and Legitimacy and systematically applied them to a sample of 342 articles from The Daily Mail and The Guardian, theoretically representing both the popular political right- and left-leaning framings of issues. Key findings of this project were that many media discourses are distorted compared to empirical realities, and that they are often expressed in dualisms and dichotomies. Media constructions of prostitution also reflect long-standing cultural themes. Nineteenth-century discourses of prostitutes as "fallen" -- simultaneously doomed victims and immoral seducers -- also appeared in many of the media characterizations of sex workers today. Finally, the dissertation argues that the neo-Victorian novels of Michel Faber and Sarah Waters consider prostitution with particular attention of the persistent historical cultural tropes. A second key finding of the project is that literature provides alternative ways of conceptualizing questions of "choice" and "harm." By including an examination of literature, the dissertation explores alternative, more nuanced perspectives that may allow superior understandings of the phenomenon than many of the "factual" media accounts.