Gender Bender ….. by Jaye Valentine and Wave

Jaye and I were talking about cross-dressing men a few weeks ago and decided to join forces on this post since we both love them  – for different reasons. He wants to bed them, :) I just want to read about them.  Here’s Jaye’s love-in about gender bending:


Bulging biceps. Ripped, washboard abs. Meaty pectoral muscles. Popping calf muscles. Deltoids, trapezius muscles, latissimus dorsi. The epitome of maleness. Rawr!

However, that strapping, muscle-bound, primo example of masculinity is highly unlikely to trip my personal trigger.

But this does. The Visual Kei movement in Japan in the 1990s made Jaye very, very happy. :-)

Not as a steady diet, mind you, but on occasion I love nothing more than fawning over a pretty boy wearing makeup and a dress. Why is that, you may wonder?

Beats the hell out of me. Why does anyone prefer one aesthetic to another? I can no more explain why I find certain men who cross-dress to be wildly sexy any sooner than I can explain my preference of the color blue instead of orange. I like it, and that’s that.

Now, that’s not to say that every attractive man wearing a dress will start my pulse to pounding and make me pant like a dog on a hot day. As Wave stated, concerning my request for one particularly tasty entry in her “Friday Guys” post of June 3rd, “You always love the same type of guy. Sleek, young, androgynous looking, but all man.”

Why, yes, in fact I do. :-)

(And yes, I’d love to see that particular Friday Guy wearing makeup and a dress, thanks for asking!)

For clarification, my personal frame of reference is modern Western society regarding gender, with gender defined as “socially constructed roles, behaviour, activities and attributes that a particular society considers appropriate for men and women.” (World Health Organization).

I’m not referring to male-to-female transsexuals, or any other transgendered persons, when I discuss cross-dressers. It’s unconditionally inappropriate to describe transgendered or transsexual persons as engaging in cross-dressing.

Neither am I talking about drag queens, who do indeed practice a variety of cross-dressing. A drag queen—or “female impersonator” to use the old-school term, “gender illusionist” for those of you in Las Vegas—is by definition a male-bodied person who performs while wearing feminine clothing, typically exaggerated in the degree of femininity: big heels, big boobs, big hair, glitzy gowns, and sparkly jewelry . . . although not always. Two gender-bending queens in particular come to mind who don’t fit the classic description—Ongina and Raja Gemini. Not surprisingly, they are two of my favorite queens.

(There are other varieties of cross-dressing, such as transvestic fetishism, which is typically described as a heterosexual man who experiences sexual arousal by wearing specific articles of feminine clothing. Cross-dressing is also a common element of cosplay, a type of performance art in which participants dress up to represent their favorite characters from anime, manga, video games, fantasy movies, and comic books.

While those are all fascinating topics—some merely entertaining, with others representing important social issues warranting contemplative thought and serious discussion—that’s not what I’m here to talk about today. I simply wish to start another glorious summer weekend by sharing with you my shallow but unbridled lust appreciation for hot, androgynous guys who embrace their inner chic and express themselves by wearing makeup and pretty clothes.

Men dressing as women have existed for the bulk of recorded history, some examples of which one can find in the mythologies of various ancient peoples, including the Greeks. However, the practice of cross-dressing in those stories usually involves force, as in the case of Heracles, or an effort to conceal identity, as in the case of Achilles.

Heracles (or Hercules, for you ancient Romans tuning in) served as a slave for one year for his murder of Iphitos, and some texts describe Heracles as forced to do “womanly work” and wear female garb.

The Goddess Thetis, mother of Achilles, dressed her son as a girl and hid him away in the court of Lycomedes to spare him from conscription into the Trojan War.

It’s only been much more recently that men “who have way too much fashion sense for one gender” (to borrow part of a quote Miss Noxeema Jackson in To Wong Foo, Thanks for Everything, Julie Newmar) have come out of their fabulous walk-in closets simply because they love the way going en femme makes them look.

Back in Baltimore, I had a very good friend (whom I’ll call “Mike”) who cross-dresses on a mostly full-time basis except for during the day while he’s at work. When I first met him (this is going back almost twenty years now), I thought he was the most adorable thing I’d ever seen. Blond hair that barely brushed his shoulders, a sweet smile and big, blue eyes, and a lithe little body that wouldn’t have recognized a gym had he tripped into the front door of one. Of all places, we met at a fetish club that was having a “Back to School” night in early September, where Mike strutted into the place wearing his younger sister’s Catholic high-school uniform. White, short-sleeved blouse with a skinny black necktie. A pleated, tartan skirt with the hem falling to mid-thigh. White knee high socks. Black-and-white saddle oxford shoes.


After I collected my jaw off the floor and reeled my tongue back into my mouth, a mutual acquaintance introduced me to Mike. I found out that his manner of dress, while special in theme for that specific occasion, was typical of him for a night out on the town. To make a long story short, we became great friends, and the first time we got together after the “Back to School” party, we had a nice getting-to-know-you dinner at his place. Once we’d loosened up sufficiently after a couple gin-and-tonics, I asked him why he liked dressing in women’s clothes.

He shrugged and said, “Do I need a reason?”

No, he didn’t. He didn’t need a reason, any more than I needed to explain my why I like Coke better than Pepsi.

Delving a little further, after polishing off a few more drinks, he assured me he wasn’t concealing any sort of secret motivation. He had no desire to become a woman, and according to his braggart of a boyfriend, Mike was pretty damn good at being a man. :-) Mike wasn’t attracted to drag queens and had no interest in becoming one. When he dressed en femme, he didn’t over-feminize: natural-looking makeup, no tucking, no padding, not even a little duct-taped décolletage, and he didn’t change the way he wore his hair or attempt to feminize his deep, sexy purr of a voice.

The bottom line, he told me, was that he felt as if he were living inside someone else’s skin when he wore traditionally masculine clothes, and he couldn’t explain why and frankly didn’t care.

I fully admit that there’s a good bit of Mike in all my cross-dressing characters, more so in some than others. He helped me to feel surer inside of my own skin, taught me that I didn’t have to explain or apologize. For those things, I’ll always be grateful to him, and infusing my characters with small glimpses of him allows me to share that with all of you.

I also have Mike to thank for my long-standing obsession with short, flouncy skirts and fishnet stockings, but that’s another story . . . .

~ ~ ~

Along with his partner Reno MacLeod, Jaye Valentine resides on Cape Cod in Massachusetts and writes gay erotica, gay erotic romance, and sometimes just plain porn.


Jaye’s wonderful essay is a great lead-in to my less fun portion of this post. :)

So, would you remove a man from your dinner invitation list if you knew he cross-dresses in private? What about a character in a romance – would you love him less as a hero if he cross-dresses for his man, even if he has muscles up the wazoo? Is a cross-dresser not a manly man in your eyes? I think gender bending men are really cool and they have to be stronger than most gay men because it takes a lot of balls (yes it does) :) and mental strength to tell your partner that you love to wear women’s underwear or outerwear, in bed and out. Imagine the conversation the first time red silk thongs show up under a suit or in the laundry! What about that hot guy in a black cocktail dress at the dinner table? Deciding what to pack  for vacations must be hell. :)

I love the different types of characters in M/M romances because the world is made up of a wonderful array of people, and I keep hoping that the more daring M/M authors will write books with gender bending protagonists for those readers who like to walk on the wild side. We’re reading gay romances in ever-increasing numbers, something that would have been a huge leap just a decade ago, and I think that a cross-dressing hero is just another brick in the M/M wall. During my research I found out that many alpha gay men in RL don’t embrace their cross-dressing brothers because they feel that they promote  a negative stereotype of gays. They may be surprised to learn that gender bending men in the real world include macho football linebackers as well as the fussy clerk in the office; they cross-dress because it makes them feel sexy and it’s as much a part of who they are, like their eye and hair colour.  There’s nothing like silk against bare skin to make someone feel sexy and desirable and when some men wear silk or lacy underwear or other gorgeous feminine apparel it gives them a feeling of  sensuality and sexual power.

I asked Thorny who recently came out as a cross dresser on his blog I’mJustThorny what it is about cross dressing that makes him feel empowered, and here’s what he said:

“So what about cross-dressing makes me feel empowered… Since what I do is more for me and my husband Jazz in the bedroom, the part that I’m most amazed about and can’t get enough of is his reaction. I wear some little lacy or silky something and feel beautiful and sexy because of the way he looks at me, touches me. He’s a talker too, so he tells me all about what he thinks and feels when I dress up and he gets to undress me! Before him, I felt like a freak for even wanting to try something on. Since him, I’ve explored it more and accepted it as something fun for us to play with sometimes. It took a while to get here — mostly because I scared myself into not talking about it — but here is good and I’m happy (and I know he is too!).”

I’m not talking in this post about drag queens since there are many stories about them, and in any event they wear women’s clothing for entertainment purposes and don’t have the motivation that gender benders do. Why are cross-dressers mostly absent as romantic leads in M/M romances? Is it because our authors don’t think that readers would relate to them other than as the best friend and won’t buy the books? We welcome different characterizations in M/M and I love alpha cowboys, cops, special agents and marines, but I also love beta characters and cross-dressers. I love to read about  protagonists who are nuanced, e.g. a cowboy or cop who can be tender as well as strong, and if a few of them wear fem underwear in bed, or welcome their partners at the door in silk stockings with garters because they make them feel real, more power to them. If a cross-dresser has a partner who loves him and recognizes this is a part of who he is, that’s awesome. Many guys like to role play for their man’s pleasure since this is another way to light his fire. :) I think if our authors portray their gender bending protagonists positively, and the characters are well defined and three dimensional, they can be just as manly and appealing as the hot alpha mob boss. On the other hand, nothing turns me off more than when I read a book about a cross-dresser who is treated like so much fodder, and his desire to go en femme is portrayed as a kink that the author adds for “colour”.

I have read quite a few books with protagonists in gender bending roles. Last January I reviewed Taking You Home by Cooper Davis which I absolutely loved and Max is now one of my favourite characters. I have re-read this book countless times because Max’s and Hunter’s story is a great ending to their romance that started in Boys of Summer. I’m not going to give you a list of books with cross-dressing protagonists, but two short stories that I enjoyed recently were Only Words and Any Excuse by Acer Adamson starring tough cop Max and his cross-dressing boyfriend Skyler. I love, love, love these characters and if you read the books you may understand why I can’t forget them, especially Skyler who is no pushover in his silky underwear and skirts. :) I can’t wait for the full-length story about this couple that the author promised to release later this year.

Vive la différence loosely translated means “to celebrate differences”, but M/M writers don’t seem to be doing much celebrating when it comes to cross-dressers. There are different types of gay men in real life so why are we so hesitant to test the waters in M/M? Sure there are a few excellent gender bending stories around like the ones mentioned above, but there isn’t a whole range of excellent books from which to choose, which is a pity because there are gender bending gay men in RL despite the fact that macho, alpha types wish they would go away. News flash – they aren’t going anywhere. :)

Back to my original reason for writing this post. Yes there is a reason other than admiring the guys in Jaye’s portion of  the post. lol. Do you like to read romances with well drawn, three dimensional characters in gay romances who are cross-dressers, or would you prefer not to go there? I’m hoping that this post will give a few more authors the impetus to write great stories about cross-dressing heroes. I know that some readers say they want their men to be men, but cross-dressers are strong men – they just like to play different games. :)

If you don’t want to read about gender bending heroes could you tell us why they turn you off?


Here are a few boyz for Jaye. I hope he shares them with Reno. :) 

androgynous, Cross-dressing, Jaye Valentine, Transgender, Transsexual


  • pilon

    Hi. First time visitor. I have a question. Could you please clarify if your blog is as much about those people who are heterosexual but feel like they belong to the opposite sex themselves to the extent that they feel like crossdressing as about gay crossdressing?(I thought it was, until I read some posts-I have no idea now)I am not even sure sexuality is any part of this, so I would like to hear as many opinions as there could be.

    Are there any heterosexual people here who want to crossdress simply because they feel like it, because you find it tasteful, because you feel more comfortable in it or because you can practically wear anything you consider tasteful (from both sexes)?

    If there are any people like that here, have you ever felt the need to figure what it’s all about, when it started, if it has anything to do with you also feeling like you belong to another gender or none at all? Is there any mislocation/evolution/transformation of ideas on sense of self? For instance the idea that what you are attracted to (men/women and cloths alike) becoming also what you want to be?

    These are the questions I keep asking myself. I am so confused. Please don’t tell me to go and talk to a psychologist. I need someone experienced rather than a shrink who doesn’t know sht about what I’m saying(plus we don’t have shrinks who specialized in this in my country). I can’t imagine watching someone pathetically try to emphatize with me.

    And thanks for reading anyway, and anyhow. (I hope my e-mail address will only be accessible to the blog owners.)

    • Wave

      Hi Pilon

      I emailed you a few minutes ago but in case you didn’t receive my email I’m leaving a response to your comment here.

      First, a clarification. This site reviews romance fiction having 2 men as the main characters. The men in the stories are usually gay.

      Rather than looking for book reviews, though, it sounds like you are looking for factual information about the different ways people can live out the complicated relationship among sex, gender, and culture. There are sites dedicated to these issues that might be more helpful than a site devoted to fiction. I suggest you might want to explore Empty Closets, a safe online space to discuss with others the types of issues you mentioned in your comment:

      Also, for general resources, you might want to look at

      I hope these sites contain useful information for you and I hope you come back here for book reviews because you’re always welcome!

      • pilon

        Thanks a lot for the response. I’m sorry, I should have been more careful as I was skimming through the page. I could have at least had a better look at the huge blog title, lol. Really, thanks a lot for the link.

        • Wave

          You’re very welcome Pilon. Visit any time. :)

  • Sylvia

    Great post, Wave and Jaye. Some of the recommended books I’ve read or are on my to read pile, the rest I put on my to buy list now, thank you very much :)

    • Wave

      Anything we can do to help you spend your money is a good thing Slyvia. :)

  • Mmm… Brian Molko…

    My favorite pretty boy. What a voice!

  • Yeah, I do need to take the time to break the list down into its elements . . . one of my summer projects. :)

    • Wave

      If you ever do break the list down perhaps you could post a link to the M/M cross-dressing books for those other readers who love them. That would be great. :)

Comments are closed.