For transgender, transsexual, genderqueer, and gender nonconforming people, emergent media technologies offer new outlets for self-representation, outlets that often last for only a brief moment. This article examines trans culture on the website Tumblr during the period from March 2011, when the authors began researching the platform, to May 2013, when Yahoo! paid creator David Karp over a billion dollars for the site. Through auto-ethnographic dialogue about the loose social networks within Tumblr to which the authors contributed during this phase, the article explores ephemeral aspects of self-representation at the intersection of postmodern art practice, sexual politics, and queer subjectivities. From at least 2011 to 2013, people collectively oriented in opposition to dominant discourses of gender and sexuality used Tumblr to refashion straight cisgender norms and to create everyday art in a hybrid media space.