First let me say that I’m very happy and honored to be writing a blog post for Gay YA. What I’d like to talk about today is the representation of cross-dressers in YA literature. Though transgender characters are becoming easier to find, cross-dressing characters are not. Why is this? I think it represents our prejudices as a society. I truly believe that cross-dressers are one of the most marginalized and misunderstood segments of the population today. I’m thinking specifically of teen cross-dressers. Gay and transgender kids have support groups, but CD teens have very few if any resources.

Representation of cross-dressers in YA literature is a mixed bag. Some books genuinely deal with the issues in a realistic way, some play to the stereotypes, and some offer a superficial treatment of the subject. I’m going to discuss some of the currently available teen cross-dresser novels.

Happy Families by Tanita S. Davis: Happy Families falls under the category of the “problem novel.” The teens aren’t cross-dressers themselves, but are forced to deal with it in their family. Teenage twins Ysabel and Justin must come to terms with their father’s change in gender identity. I liked the fact that this subject was being dealt with in a YA novel, however I think the treatment was superficial and unrealistic. For example: before his son and daughter know anything about his being transgendered, the father shows up in full drag to his son’s debate and later gives the explanation that his flight was late and he didn’t have time to change. Would a real person do that?

What bothered me the most was that the author took a very simplistic view of the subject matter. Several issues were never addressed: Was the father’s transition heading for surgery or would he be happy with cross-dressing? Was the father interested in having relationships with men or did he want to be with women? Though it’s very positive that someone wrote a novel about a cross-dressing father, Happy Families didn’t begin to address the nitty-gritty issues such a family would face.

Debbie Harry Sings in French by Meagan Brothers: When Johnny’s father dies and his mother retreats into herself, Johnny turns to alcohol to deal with his problems. He’s Gothy, usually wearing black nail polish and mascara. When he discovers Debbie Harry, the lead singer of Blondie, he realizes that he’d like to BE her. He has no gay tendencies, but dressing like the cool, tough pop star quells his angst and makes life bearable for him. He doesn’t quite know how to tell his girlfriend, though. This a quirky and touching story that rings true throughout. It shows what it feels like to be an outsider and how society deals with people who deviate from the norm. Debby Harry Sings in French talks about the aspect of cross-dressing that is seldom discussed—that is cross-dressing for improved self-confidence and enhanced self-esteem.

Freak Show by James St. James: When teenage drag queen Billy Bloom is forced to live with this uncle in the Bible Belt, life falls apart for him. This is an over-the-top campy book about a boy who goes to school in the most outlandish drag queen outfits he can possibly come up with. It’s funny and entertaining, but it’s not meant to be realistic. It feeds into the stereotype that many people think—that cross-dressers are all drag queens.

The Flip Side by Andrew MatthewsThe Flip Side provides a different take on the Shakespearean mistaken identity plot. Robert Hunt is asked to play the female role of Rosalind, opposite his classmate Milena as Orlando. Rob discovers that he likes dressing up as a woman, and, more importantly, he likes who he is as Rosalind: stronger and more confident than he is when he’s just Rob. Thus begins his experimentation with cross-dressing and exploration of his own sexuality. Though it’s admirable that the book deals with these issues, it often reads like a bad sitcom. It’s convenient that Milena is also sexually questioning, that Rob’s best friend reveals that he is gay, and that his classmates are equally interested in gender-bending.

Boy2Girl by Terence Blacker: is about a boy, Sam Lopez, who dresses as a girl as a prank at an English boarding school. Sam gets into the whole thing a little more than he expected to, giving makeup lessons to the girls and eventually wearing a bra. The story is told in short chapters by various viewpoint characters, which is interesting. The author is mainly going for humor here. The ending is a little over the top and everything wraps up too conveniently.

Boy in the Dress by David Williams: is aimed toward middle grade readers. Dennis is a twelve-year-old boy who loves poring over Vogue magazines. Dennis meets up with Lisa who is two years older and also loves fashion. She plays dress up with Dennis and convinces him to come to school as “Denise,” a French exchange student. Funny situations result, and there are poignant moments between Dennis and his dad and brother. The book is a quick read and it is good for bringing awareness of gender issues to a younger age group.

The Sweet In-Between by Sheri Reynolds: This book is one of the few that deals with female-to-male cross-dressing. Kendar (Kenny) Lugo has lived with her father’s girlfriend, Aunt Glo, ever since her father went to prison for drug dealing. She binds her breasts, cuts her hair short and wears boy’s clothing. She hates the fact of being female and rejects the changes her body is going through. Kenny is bullied at school but finds redemption through the kind teacher who runs the school yearbook. A tragedy sends her family spiraling out of control. Sheri Reynolds is a master of character development. The story is engaging and rings true. In the end, the story is uplifting.

Princess Prince by Tomoko Taniguchi: This book is manga, which has a long history of gender-bending. Set in a medievalCevins_Deadly_Sin_72dpi4in fairy tale land with creatures called “angel birds,” twin male princes, Matthew and Lawrence, lived a normal life until their mother’s tragic death, which made their father, the King, believe that an ancient prophecy was put into motion. The king thought the only way for his boys to be spared from this curse was to raise one of them as a princess. When puberty hits, complications arise for the twins. The book has beautiful illustrations and follows fairytale conventions. This novel is an example of forced feminization.

Cevin’s Deadly Sin by Sally Bosco: Okay, this is my book, and that’s why I’ve left it for last. It’s the story of a hetero, teen cross-dresser: his struggles with first love, self-identity and bullying during his senior year in a small, Florida town. In writing this book, I researched the experiences actual cross-dressers encountered during their teen years, and I tried to mirror that in my portrayal of Cevin. I also strongly wanted to make him heterosexual because many of the cross-dressers I met were hetero, contrary to popular belief. The book portrays an otherwise normal teen boy and the struggles he encounters while learning how to turn his outsider status at school into an asset. It was my master’s thesis for an MFA in Writing Popular Fiction.


These are some recent young adult cross-dresser novels. I think they are important because they encourage acceptance of those with non-standard gender roles. I hope you’ll be encouraged to read some of them.

Do you know of any other books to add to this list?


Sally Bosco 0214Sally Bosco has a fascination with gender: the perceptions we have, the attitudes people have toward those who don’t fit into the usual categories, and the feelings we have about our own genders. She loves writing young adult fiction because she strongly relates to teenage angst, the search for self-identity and the feelings of being an outsider. Check out her webpage at