This thesis aims to examine how sadomasochism has been altered from the time of its production. Furthermore its aims to display how the dynamics of pleasure and pain in a sexual context can have an effect on general attitudes towards violence against women. To trace sadomasochism and its literary tropes through history, it is evident that the gothic period in England served as a distributing landscape that brought a censored version of the Marquis de Sade’s Justine into public domain. Romantic comedies in the 1950’s have also played a part in distributing Sadeian tropes as well as depicting desired traits of femininity, which are still prevalent today. Lastly, the contemporary cultural landscape suggests an increased demand for violent pornography. This demand functions as a regressive indicator of many conventional sexual practices. By examining sadomasochistic tendencies in popular erotic fiction, it is evident that traits of sadomasochism are common doing both sexual and non-sexual exchanges between men and women. Moreover, the increased aggressive discourse in pornography does not serve a common purpose with its inspirations, rather it affects online Incel communities which thrive on sexual frustration and exclusion. The effect of this discourse paves the way for the increasingly regressive conventions regarding free sexual expansion, biological power and finite freedom.