Activism for socio-political movements has been affected by the progression of technology, enhancing the conditions under which advocates can communicate worldwide. Recently, Tumblr has announced accommodating large numbers of young transgender identified individuals. This article will offer an historical analysis of the progression of gay rights throughout the twentieth century, in comparison with the similar trajectory of the transgender movement now being catalysed by technology. Through discussing key arguments in transgender theory such as the pathologisation of Gender Dysphoria in the DSM; the heterogeneity of the transgender community; and rejecting essentialist ideas of gender: we can begin to understand the need for further integration of the rhetoric of gender fluidity into the public space, in which wrong body discourse and the politics of passing can be deconstructed. By dissecting the history of mainstream media representation of gay identities, we can now understand them to be in the final ‘respect’ stage, progressing through ‘non-recognition’, ‘ridicule’, and ‘regulation’ (Clark, 1969). A further comparison with transgender representation will highlight a non-recognition of the full heterogeneity of their community, which exemplifies the need for public discussion. Tumblr has a unique opportunity, as the biggest cyberspace community of young transgender identified individuals, to impact dialogues created around transgender politics. A discourse analysis of Tumblr’s platform evidences a need to optimise its usability for transgender members. The arguments will conclude proposing that Tumblr has the ability to create a space for influential dialogues that could expand past Tumblr and into wider public spaces.