Cross-Dressing Dudes Getting In Touch With Their Feminine Side

29 Mar

By Elizabeth Shore

Let’s say you’re a guy, perfectly comfortable in your guyhood. You rock a pair of jeans and a t-shirt with the best of them, you love a good bicep and pec workout, and Mr. Johnson definitely pays attention to a beautiful woman. But in addition to your typical male tendencies, you also have a hankering to paint your toenails pink, strap on a pair of 4-inch stilettos and slink around in a pretty dress. What’s a cross-dressing guy to do? How can he learn to walk in heels, properly apply make-up and embrace his feminine self? Fear not – help is available. Introducing Miss Vera.

“We live in a time where gender is an option.” So says Veronica Vera, a.k.a. “Miss Vera,” founder and dean of Miss Vera’s Finishing School For Boys Who Want To Be Girls. Founded 25 years ago in New York City, Miss Vera and her fellow “deans” – each of whom has a particular specialty – are an oasis of help for cross-dressing men. Becoming a student at this modern-day finishing school means a guy can learn how to moderate his voice to achieve a more feminine pitch, properly style his hair and/or wig, strut his stuff no matter how high the heel, and apply make-up to transform and bring out his inner diva.

Miss Vera’s ultimate goal, according to a video on her website, is to “increase the awareness of your options as a human.” In other words, we’re not relegated to living strictly as our biological birth would dictate. Instead, we can be ourselves with whatever gender we identify. “Average Joe” during the day, “fabulous Joanne” after hours. No need to struggle over how to make it happen. Miss Vera’s academy will show you the way.

Aside from achieving the desired physical look, the finishing school also offers courses that bring the closeted cross-dresser to the streets. How to shop, dine, even feel comfortable using the ladies’ room are all in the offering. It’s not just about looking and acting the part. Miss Vera’s teaches her eager students how to “be” a lady.

When musing on being a crossdresser, one straight, cross-dressing guy wrote in a blog post on, “What most of us want more than anything is validation of our femininity.” Miss Vera’s Finishing School seems to understand that well, as their motto is “cherchez la femme,” or “look for the woman.” The goal, as stated on the website, is to “allow your femmeself to open you up to the world, not isolate you from it.”

All this gender acceptance is cool, but what if you’re the spouse or significant other of a cross-dressing guy and are struggling to understand and be supportive? Working with couples is more common than ever before at Miss Vera’s. Being the partner of a cross-dresser herself has helped her develop deeper insights into the psychological and emotional challenges of similarly situated couples. In consultation with them, she’s discussed topics such as role-playing, communication, children, and bisexuality.

It’s interesting to note that the straight guy in the article made sure to point out that his interest in cross-dressing isn’t at all a sex-based need. As he says, “It’s a look, not a fetish. … It also took quite awhile to come to an understanding that dressing to feel sexy didn’t make dressing sexual.”  He’s not bisexual; it’s not a kink thing. The dude just wants to bring out his sexy side by looking and dressing like a gal.

Despite today’s broader proclivity toward identity acceptance, finding out your guy fancies wearing lacy panties can be a couple crusher for many. Certainly within our romance book world, gender benders are primarily women dressing as men, and usually in historicals where a woman is trying to do something available only to the guys. To be sure, a romance with a bad boy alpha male, the leader of a motorcycle gang, for example, would be a hard sell if the reader learns that the dude likes wearing fishnets beneath his jeans.

But perhaps that’s an assumption. What do you think? Does a cross-dressing straight guy a believable hero make? Sound off in the comments. And if you’ve got a good cross-dressing romance to recommend, let us know that, too. Here at Lady Smut, we’re never at cross purposes in talking about romance.

Elizabeth Shore writes both contemporary and historical erotic romance. Her newest book is an erotic historical novella, Desire Rising, from The Wild Rose Press. Other releases include Hot Bayou Nights and The Lady Smut Book of Dark Desires



4 Responses to “Cross-Dressing Dudes Getting In Touch With Their Feminine Side”

  1. Madeline Iva March 29, 2017 at 12:11 pm #

    I think we’ll have a much stronger sense of what underpins cross-dressing in another ten years, now that it’s not seen as deviant behavior like it was, and now that it’s been uncoupled with sexual orientation. I’ve given the side-eye to cross dressing in the past–do you remember, Elizabeth?

    I wrote a review of a historical with a cross-dressing hero — here:

    And also another post:

    Liked by 1 person

    • Elizabeth Shore March 29, 2017 at 12:47 pm #

      I do indeed remember! So funny, while I was writing this post I thought of you. I’d figured you’d have thoughtful things to say. 😉


  2. Kel March 29, 2017 at 7:43 am #

    I think there’s a lot more room in gender roles than people think. Why else would so many people be so interested in historical romance novels, when traditional (historical) upper-class male attire has so many of the intricate details that are limited to women today? Not to mention the use of heels was originally for men’s footwear; women adopted them to appear more masculine. Anyone who thinks that the modern man doesn’t spend just as much time and effort on his appearance as women do has never walked in on a discussion about beard oils in the office. My brother taught me to put on eyeliner properly (ah, goths – no one does eyeliner like you – also, it was the 80s, I plead cultural poisoning), and the very first person to introduce me to the joys of pedicures was a very manly biker I know… another knit an amazing santa-hat cozy for his helmet, and my riding group went nuts for the pattern…

    Granted, they’re not romance-book heros, but I don’t think there’s as much “oh noes! gender role violation!” as people think. Don’t tell me you’ve never shared your face creams with your partners…. I won’t believe it; they’re probably just sneaking them when you’re not looking…

    What’s a little silk or lace after all that? Silk feels wonderful, anyone who wants should be able to wear it. Plus, boys are pretty (too), they should get to wear pretty things when they want to. Humans like that – both on themselves and on each other.


    • Elizabeth Shore March 29, 2017 at 11:29 am #

      I agree completely, Kel. But the question is, are silk-wearing pretty boys able to make the grade in romance novels? So far I just haven’t seen it, at least not much. Those few I come across are more on the fringe. The question is, even with the growing trend toward acceptance of gender differences and being to identify with whatever gender one wants, will a guy wearing silk undies be able to cut it in the romance world as the hero? Time will tell…


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