*Maybe Tomorrow by Jay Little (Pageant Press, 1952)
Gaylord LeClaire ("Gay" for short) grows up in Cotton, a small town in Texas. By the time he's in High School, he realizes he is different from all other boys: he wishes he were a girl and is attracted to boys, particularly Bob Blake, the handsome, friendly, and charming captain of the football team. Fortunately, Gaylord is very attractive (albeit "pretty") and has a big dick, and although he is bullied and teased -- he's nearly raped in the locker room by a group of boys who call him a "Venus with a Penis" -- he is also befriended, rather suddenly, by Bob Blake (and his girlfriend Joy). It turns out that Bob is secretly gay and loves Gaylord, even if he calls him "my beautiful faggot."
Gaylord's parents (unwisely) take him to New Orleans for a weekend, where Gaylord is promptly taken underwing (and into bed) by a handsome and pleasant but unhappy homosexual named Paul. Paul takes Gaylord to a dive gay bay and then to a private party hosted by Gene, a mincing and shrieking queen, attended by an assortment of faggots, including Gus, a butch number who does a balletic striptease and tries to pry (literally) Gaylord from Paul's arms.
Although many gay men may have spoken and acted exactly like the "faggots" Gaylord encounters in the Big Easy, reading these scenes now is disturbing: one realizes this exaggerated, self-loathing behavior is a result of ceaseless ridicule, mental and physical harassment, and debilitating repression, and that the "inversion" of homosexuality is something that is forced upon homosexuals, not something that is innate. A tree grows thwarted and crooked only when it is prevented from growing as it naturally would.
Characters in pre-Stonewall gay novels are usually doomed to death and (self) destruction, but Jay Little gives all the gay characters in this book unusually happy endings: Bob and Gay decide to pack up and move to New Orleans as soon as they graduate from High School -- be careful, boys! --and Paul picks up a nice masculine married man who decides to never leave once he gets to Paul's tastefully decorated bachelor pad (complete with a goatskin on the bed). And Gaylord is an admirable character -- he is kind, honest, and loving. So in many ways, this book, while disturbing in its unnuanced and objectifying portraits of many of its gay characters, is a delightful anomaly in pre-Stonewall queer literature: a feminine boy is an admirable hero. He gets the football player, befriends the dimpled, hunky farmboy (a subplot), and lives happily ever after -- maybe tomorrow.
Jay Little in (above) and out of (below) drag. More photographs, and an interesting and well-researched examination of Jay Little and Maybe -- Tomorrow are featured on Brooks Peters' blog An Open Book.