1. Kay, The Night Watch by Sarah Waters
In the years after the Second World War, Kay walks the streets of London in man's clothing, left hollow by her experiences during the Blitz. With all the men away, Kay had found it easy to fill their shoes, becoming a hero to those such as Viv who needed her help as an ambulance driver, and playing husband to the young, unsure Helen. Kay's sheer disregard for the period's limited view of gender is joyously refreshing, but Waters tempers this exuberance with pain. Kay witnesses some horrific things in the war, and the woman she loves betrays her. At the beginning of the novel, which coincides with the chronological end of the story, she sees herself as little more than a ghost.
2. Cal, Middlesex by Jeffrey Eugenides
Born Calliope to second generation immigrants, Cal enters adolescence as an intelligent girl, curious about her growing feelings for a female friend. As we flash forward to adulthood, Cal is now narrating the story as a fully grown man. The transformation undergone by the character is revealed at a leisurely pace, as Cal first tells us of the struggles and secrets that led his/her family to America, which in turn allowed Cal to come into existence. A fantastic story, told by an unforgettable character.
3. Mr F, Skin Lane by Neil Bartlett
What is most frustrating (and at the same time, moving) about the protagonist of this novel is that he does not come to consciously realise his own desires until midway through the narrative, and it is only in the closing pages that he comes close to fulfilling them. While every stage of his infatuation with the young man named Beauty is written in painstaking detail, it is Mr F's isolation that makes him relatable to the reader. At no point does he identify with other gay men, it is his simple assumption that he is alone. The 1960s setting of the novel cements a concept that would be laughable in a book set in the present.
4. Lestat, The Vampire Chronicles by Anne Rice
The "brat prince" Lestat is perhaps one of the most sexually fluid characters I have ever encountered in fiction. From his early Svengali-like relationship with Louis, to his eventual fascination with Rowan Mayfair, it is not gender that attracts or influences Lestat, but beauty itself. His arrogance, vanity and irrepressibly playful nature make him all the more compelling.
5. Villanelle, The Passion by Jeanette Winterson
Much like The Night Watch's Kay, Villanelle cross-dresses in a time period where such a thing is unheard of. Unlike any other character on this list, however, Villanelle has webbed feet and can walk on water. She is a child of Venice, the city of mazes, and she is as much a contradiction as her birthplace. The portion of the novel dedicated to Villanelle's story, The Queen Of Spades, sees our heroine fall in love with an aristocratic seductress, only to have her heart stolen - quite literally. So ensues a quest to get it back.