Orlando

Virginia Woolf's most unusual creation, Orlando is a fantastical biography as well as a funny, exuberant romp through history that examines the true nature of sexuality.
As a teenage boy, the handsome Orlando serves as a page at the Elizabethan court and becomes the favourite of the elderly queen. After Elizabeth's death, he falls deeply in love with Sasha, an elusive and somewhat feral princess in the entourage of the Russian embassy.
Virginia Woolf's Orlando 'The longest and most charming love letter in literature', playfully constructs the figure of Orlando as the fictional embodiment of Woolf's close friend and lover, Vita Sackville-West. At the midpoint of the novel, Orlando, now an ambassador in Constantinople, awakes to find that he is now a woman.
The book describes the adventures of a poet who changes sex from man to woman and lives for centuries, meeting the key figures of English literary history. Considered a feminist classic, the book has been written about extensively by scholars of women's writing and gender and transgender studies.