• This chapter argues that the sexy librarian stereotype emerged at the end of the twentieth century from the confluence between sexual liberation, free speech movements and print pornography. It focuses on a series of librarian themed pornographic paperbacks published in the 1970s and 1980s by Greenleaf Classics. These stories, although flimsy plot-wise, tend to be obsessed with the idea of liberating stuffy librarians from the shackles of sexual conservatism, thereby dramatizing some of the social struggles surrounding obscenity cases and the move to deregulate print materials.