Orlando by Virginia Woolf (1928)Read about another entry on the list.
One of the most beautiful love letters ever written. Addressed to Vita Sackville-West, it originally included photographs of her in both feminine and masculine clothes. Vita is Orlando, a dashing young man in Tudor times, who buckles a few swashes at home and abroad before changing sex and living on to the 1920s. As a man, Orlando courts women, as a woman men – so far so conventional – but as a wo/man, s/he is swaggeringly queer. The book is a jeu d’esprit that Woolf clearly wrote when intoxicated with love. While waiting for the trial of The Well of Loneliness, Una Troubridge helped her lover Radclyffe Hall endure the stress by reading Orlando to her.
Orlando is among Jonathan Gibbs's top ten fictitious biographies and Sam Mills's top ten fictional sex changes.