Arundhati Roy’s The Ministry of Utmost Happiness and Trace Peterson’s “After Before and After” have been studied in several aspects related to transgender issues. The presentation of transgender people, especially the transgender protagonist in The Ministry of Utmost Happiness, has been criticized as a formulaic depiction with little portrayal of their struggles and triumphs. At the same time, the transgender protagonist is viewed positively as an integral force in the novel. The poem “After Before and After” has been praised for its creative portrayal of transgender people. A study of transgender issues in relation to desire and connection helps to show that both texts offer more possibilities of liberation towards the state of “becoming.” This study applies Gilles Deleuze and Félix Guattari’s theory of schizoanalysis to explore transgender people’s lines of flight, rhizomatic movements and transversal connections towards the state of deterritorialization in India and the US.