Transgender Home » Transgender Fun & Entertainment » Three Books Featuring Crossdressing

Three Books Featuring Crossdressing

The Editor | Jan 29, 2024

Spread the love

by Elizabeth Parker

In Four To Score, the latest Stephanie Plum mystery by Janet Evanovitch, Stephanie, a bounty hunter, is on the trail of an elusive woman, Maxine, who has a score to settle with her ex-boyfriend. Maxine has taken some embarrassing love letters he wrote and he wants them back badly, for some mysterious reason. She took his car, was arrested, then skipped out on her bond, bringing Stephanie into the picture. Maxine starts leaving cryptic clues in disgusting places for the ex-boyfriend to find, directing him how to get to the next one and eventually, the pictures. Being a dim-witted bodybuilder, he leaves the decoding to Stephanie.

Stephanie has trouble decoding the notes also, so when one of her elderly friends recommends her nephew, she enlists his aid. She discovers that the nephew performs in a drag rock band under the name of Sally Sweet. He is very tall, a la RuPaul, but is quite an ugly woman. He gets a kick out of helping her, and invites himself along on several excursions to track down Maxine. We learn along the way that he is a heterosexual transvestite (hetero to his birth gender that is), and Evanovitch does a good job of making him a sympathetic and engaging character. Sally is accepted quite well into Stephanie’s offbeat band of misfits, and the door is left open for future excursions.

That is all fine, but what really earns this book headline status is the subplot involving another member of the band, Sugar. Sugar is the band’s lead singer, and Sally’s roommate. Sugar is definitely homosexual, and has quite a crush on Sally. Sugar dresses up as a very beautiful woman, and provides us with several very exciting moments. I can’t say more, but you will enjoy this book. The humor is good, the action doesn’t drag, and we get two different transgender characters.

The next book is quite different. It is Dreamhouse, by Alison Habens. It is the story of a modern day Alice in Wonderland and is very much as fantastic as the original. Part of the fun in this book is figuring out just who Alice really is.

The book centers around four housemates; Celia, a prissy girl who desperately longs to get married; Phoebe, a glum lesbian; Cath, a hippie type who holds an Alice In Wonderland party on the night this book covers; and Dodge, a hermit whom the girls almost never see. Celia, Phoebe and Cath don’t get along very well, and things come to a head when they discover they’ve each scheduled a party for the same night. Celia is holding an engagement party for her family and her fiancé’s family, Phoebe is hosting a welcome-back party for her sister, and Cath is having the aforementioned masquerade.

On party night things start to get very weird. Celia leaves her engagement party and visits the Alice In Wonderland party. Dressed in her usual overly feminine attire, and with her long blond hair, she is instantly mistaken for Alice. When she eats some spiked jam tarts, the world turns bizarre. Eventually she makes her way down to Dodge’s room where he offers her refuge. Through his actions, Celia thinks he is in love with her, but it turns out he actually wants to be her. Yes, Dodge is a crossdresser and quite naturally loves how she dresses. She tearfully switches clothes with him and he goes to the masquerade party as Alice. Of course, complications ensue.

This book was a fairly fun read. I generally lose interest when things get weird and unbelievable and this tale almost falls into that category. But the crossdressing spiced it up, and some serious issues are raised and dealt with in an amusing way. So I would recommend the book if you don’t mind the sort of psychedelic writing common in the late ’60s. If you prefer more hard-core stories planted in the real world give it a pass.

Finally I thought I’d point out a Sherlock Holmes short story you might have missed. It is found in the book The Confidential Casebook of Sherlock Holmes, edited by Marvin Kaye. The book is full of slightly offbeat and entertaining takes on Holmes, by contemporary authors. The story of particular interest to us is The Affair of the Counterfeit Countess, by Craig Shaw Gardner. In it Sherlock Holmes masquerades quite convincingly as a baroness, to penetrate the inner circle of a Duke who likes to be surrounded mostly by women, a desire I’m sure many of us share! Holmes does his job with his usual competence, but bites off a little more than he can chew, as well.