Orlando, Virginia Woolfs fantastical tale of young prince Orlando is a delightful confection of subtle wit and obvious affection for those of us who struggle against the social confines of gender. Initially scandalous for the obvious resemblance between the title character and Vita Sackville-West, Woolfs lesbian lover, the book has shed controversy through the decades, leaving us a lesbian and trans classic that reads as if it could have been written yesterday. After he is granted eternal youth by Queen Elizabeth, young prince Orlando embarks on a journey spanning 400 years, multiple continents, various historical literary styles, and two sexes -- after 10 days of trance-like sleep, Orlando wakes up as a woman. Perhaps most contemporary is Woolfs treatment of gender fluidity as a simple fact of Orlandos life and by extension ours. Whats shocking is not that Orlando is a woman but that society now expects her to settle down and be good. Isnt that always the way? 10 other essential trans titles: 1. Stone Butch Blues by Leslie Feinberg (1993) Feinbergs classic evocation of butch-femme community and working-class trans lives was one of the first of its kind and is still essential after all these years. 2. Last Report on the Miracles at Little No Horse by Louise Erdrich (2001) Father Damien Modeste, a missionary living among the Ojibwe of North Dakota, is revealed to be a woman in this National Book Award finalist. 3. Gender Outlaw by Kate Bornstein (1994) In a book as smart as it is funny, Bornsteins humor makes her challenge to gender defenders go down easy. 4. Christine Jorgensen: A Personal Autobiography by Christine Jorgensen (1967) Jorgensen became the public face of the emergent trans movement when she came out about her transition in the early 1950s. 5. Read My Lips by Riki Anne Wilchins (1997) Wilchins combines political analysis and personal memoir in her call for trans-inclusive feminist and gay movements. 6. Myra Breckinridge by Gore Vidal (1968) Myra can collect an inheritance left by her late husband only if she keeps her gender secret in this wickedly funny camp classic. 7. Trumpet by Jackie Kay (1998) Kays novel about the danger of secrets is based on the true story of Billy Tipton, a transgender musician of the 1940s and 50s. 8. Sublime Mutations by Del LaGrace Volcano (2000) Self-described gender abolitionist Volcano celebrates the profusion of queer bodies in this collection of portraits. 9. The Transgender Studies Reader edited by Susan Stryker and Stephen Whittle (2006) Get a grip on essential theoretical and political debates with these bite-size selections from seminal thinkers ranging from Harry Benjamin to Dean Spade. 10. The Last Time I Wore A Dress by Daphne Scholinski (1997) Scholinskis harrowing memoir is a powerful illustration of the harms that come when we fail to embrace the diversity of human gender Send a letter to the editor about this article.