I will be investigating the merit of participatory culture in online literary roleplaying. While looking at an affinity space within participatory culture, I will be examining the importance of narrative within a roleplay board, the value placed in writing ability and habitual participation, and the gaining of social capital within the affinity space of players through the scope of two forms of participatory culture: expressions and collaborative problem solving. I will also look at the limitations of literary roleplaying before talking about the potential of roleplaying to be used as a tool for students in the classroom. Throughout my investigation, I pool information from online roleplay forum boards as well as Tumblr blogs. Drawing from these examples, I hope to not only show the value and merit of online roleplaying as a form of literature, but also demonstrate its potential as a curriculum guide for educators.