To avoid the stigma of societal dissaproval, love for somebody of the same sex has often been hidden from the declinatory views of the public; however, it has also been secretively transcribed into a broad spectrum of art. Virginia Woolf embroidered her homosexuality into the grotesque lines of Orlando. At the time, Woolf was engaged in an intense lesbian relationship with author Vita Sackville-West, who served as a model for the work’s main character. Woolf proclaimed her masterpiece “A Biography”, mirroring the duality of her own and Vita’s character, the perpetual beauty of the book’s hero, enduring for centuries, and his subtle gender transition. In the paper, we discuss some of the homosexual motifs in Orlando, which were formed by different influences, including the queer movement, ancient Greek literature and feminism.