Cross-Dressing’s Erotic Side

Grayson Perry-sexy

Grayson Perry, in drag

Being a transvestite is a complex cocktail of motivations. It’s different for everyone, but there’s often a strong sexual component to cross-dressing, although trannies sometimes find it hard to admit this. I feel it’s like the elephant in the room. I feel it’s really there, but nobody’s talking about it.

Maybe it’s this erotic dimension which is the hardest part for others to accept.

That’s what artist and cross-dresser, Grayson Perry thinks.

“Vivienne,” over at Bluestocking Blue began blogging to better understand why “she” feels compelled to cross-dress male-to-female. 

Escaping the hard mask of masculinity is part of that push. But she also finds cross-dressing sexually arousing. Why?

After much searching Vivienne found something that clicked with her experience: autogynephilia, from the Greek meaning “someone who loves himself as a woman.” These folks get turned on by the image of themselves as the opposite sex.

Vivienne says,

It fits with why I think high heels are sexy… It fits Helen Boyd’s painful and forthright observations about some crossdressers: eternally selfish, frequently overspending, sexually interested only in themselves (not their wives). It fits with what most customers want who go to that makeover shop… It even fits my phenotype (white, successful, high IQ).

Now mind you, Jack Molay is an autogynephile who explains that “they do fall in love with real women ‘out there’ all the time, and are often very loyal partners and husbands” even if they do have this other thing going on.

Grayson Perry, out of drag

Grayson Perry, out of drag

Most biologists who study the phenomenon believe it has a biological component, Molay adds, perhaps involving prenatal hormones.

But since women’s clothing holds no innate meaning — with skirts, dresses and makeup being the norm for men in some cultures – a symbolic component is also clearly involved.

Jack Molay believes there’s a biological core that’s expressed through cultural symbols.

Vivienne agrees:

My best guess is that I was born with a set of innate tendencies which were shaped by my upbringing and societal norms, and I now express those tendencies by cross-dressing.

Mr. Molay says the most frequently used search-phrase that lands people on his blog is:

Is there a cure for autogynephilia?

He adds,

The short answer to this question is no… I have read most of the literature. I have so far not found one reliable story about (anyone) who has been cured of this.

Meanwhile, plenty of people have tortured themselves trying, whether through electroshock and nausea “therapy” or burning their womanly wardrobes or punishing themselves for erotic thoughts.



Vivienne, herself, seems fearful:

This disturbs me, because the natural history is that cross-dressing becomes more predominant as one gets older (and in some cases, leads to full transition [to a woman])…

I had thought that, if I was able to find just the right frequency of dressing, I would be happy in my “ordinary” life. This model suggests that point won’t be reached; there will never be enough… to the point where it gets in the way of my ability to be a useful and productive husband and father. 

That’s not something I relish in any way, and may explain why some of the people I’ve found on the Web that I have most in common with are people trying to quit crossdressing: these are people who are trying to keep a foothold so that crossdressing doesn’t overwhelm them (but the science suggests we are incurable in every reasonable sense).

On the other hand, Jack Molay suggests cross-dressing may keep autogynephilia from overtaking your life.

Vivienne’s wife gives him hope:

She pointed out that just because there is a model out there, and that I happen to fit it, it doesn’t change who I am; it doesn’t change what I do; it doesn’t change what will happen in the future. She was right, of course, and I am extremely grateful for this insight, which frees me from what had seemed like a gloomy inevitability.

I haven’t studied this a great deal and most of what I know I’ve learned from Vivienne. (I’ve been interested in applying social construct theories to the experience.)

I hope to help bring greater understanding and love to all on this planet.

Thank you Vivienne, for sharing your experience and your struggles. I wish you the best.

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About BroadBlogs

I have a Ph.D. from UCLA in sociology (emphasis: gender, social psych). I currently teach sociology and women's studies at Foothill College in Los Altos Hills, CA. I have also lectured at San Jose State. And I have blogged for Feminispire, Ms. Magazine, The Good Men Project and Daily Kos. Also been picked up by The Alternet.

Posted on March 4, 2015, in feminism, gender, LGBTQ+, men, psychology, sex and sexuality and tagged , , , , , , , . Bookmark the permalink. 22 Comments.

  1. Many thanks, as always, Georgia, for your thoughtful comments about my blog, and for drawing it to the attention of others.

  2. Caroline Dietrich

    Thanks for this great post. I really enjoyed reading Vivienne’s quotes to get a bit more insight on the topic. I personally think transvestites are an interesting topic that is often looked down upon in our culture and rarely talked about. Some might find it odd if they see a muscular man wearing a tight woman’s cocktail dress yet on the contrary if you were to see a feminine woman wearing men’s workout clothing you might not think of it as odd. (You might think that she stole her husbands sweats for the day_ Of course there are those men who when dressed in the female self they almost look better. Take Gigi Gorgeous (formerly known as Gregory) for example. She is a YouTube sensation and is a transitioned transgender. She (who was once a he) believes that she was born into a males body yet is suppose to be a woman. Having plastic surgery such as adams apple removal, chin reduction, breast augmentation and so on. When I looked at her the first time I thought she was a gorgeous woman. She is not a cross dresser rather she has transformed herself into a woman. She wears makeup and wears girls clothing, I’m assuming takes hormones to make her voice change. Overall, I think it is great that we are coming to be more accepting of transgender in our culture.

    • Thanks for your thoughts.

      And it can be confusing because transvestites usually have a strong sense of themselves as straight males. But at some point some can cross over to transgender.

      • I think Gigi is confusing. At first, her YouTube videos identified her as a gay man who enjoyed drag, and was very successful at it.

        Then later, she decided to transition, and has made a very good job of it.

        I find myself wondering: if Gigi was built like a linebacker, with a big bristly chin and big square hands, but had exactly the same tendencies and preferences, would she have transitioned? Or would she have found that, as a gay man who likes to dress up, that was “OK”, but to fully transition (knowing she would never pass) was “not OK”? (By which I mean, not manageable as a lifestyle).

        I realise that I don’t look very passable as a woman (which deters me), but I wonder, if I had the figure and bone structure of Gigi, whether that would change my approach to crossdressing? I think it maybe would.

        And if society were to suddenly approve of public crossdressing, there would be no stopping me (and the same is true, I suspect, for many thousands of closeted people just like me).


  3. As a man with a strong feminine side that also wears some women’s lingerie, jeans, sneakers, uses moisturizers, gets pedicures and facials, I have found the linked article in rolereboot best describes my feelings about crossdressing and how it relates to my life. Please read the article and let us know your thoughts.

    • Thanks so much for sending me this article. I think I’ll have to blog on it.

      Before I get into the cross dressing I think it’s interesting that the male writer was, as a young adult, surrounded by young men who we’re fairly misogynistic — which ties into his later comments on why women are less likely to cross-dress, having greater permission to dress and act like men, because they aren’t seen as humiliating themselves by doing so. And the guys’ misogyny is a way of creating a sense of male superiority: trying to raise yourself up by putting others down (but really creating inferiority in the process — because hateful, misogynist people are hardly superior). I wonder if this sort of thing is particularly common among young men who are entering the threshold of adulthood and are more insecure in their sense of manhood than they are when they get older.

      So in order to do “be men,” guys have to reject half of themselves. Because men naturally have what we call a feminine side.

      The writer, on the other hand, very much wanted to maintain his whole self. So it makes sense to put on the costume of femininity (as constructed by the society) to help get more in touch with it. Actors sometimes say that they couldn’t get into the character until they put on the costume — it help them to get in touch with, and embody, the character traits they are interested to bring out.

      Women’s clothing has no innate meaning as feminine. Men have worn dresses and skirts and makeup and jewelry in a variety of cultures. But women’s clothing has a certain meaning in Western societies that some men use to get in touch with the feminine side of themselves that they don’t want to cut off.

      The fact that something is socially constructed can sound like it’s trivial. But social constructions are extremely powerful. So much so that some men can feel compelled to wear women’s clothing, Whether to get in touch with their feminine side or to get in touch with their sexual side (Which many think of as feminine — seems like most sex diety are associated with women: Venus, Aphrodite, Frejya, Hathor…)

      Interesting that the writer went crazy when he finally let his feminine side out.

      Interesting also how he talks about how society separates these two sides of ourselves so that they seem separate, when in fact the two parts should feel whole, because all of us contain both parts.

      He seems to me to be doing his best to use women’s clothing as a prop to make his feminine side more present and real. Makes perfect sense to me.

      • Thanks for posting this link, Uxorious. The author is very insightful and his article captures many of my own feelings and attitudes exactly. I think I will link to it from my own blog.

  4. I feel sad about those people they feel like they got trap in the wrong body and feel shame to do something to express whatever they want to. But I am encouraging them definitely should do something that would make them feel comfortable and happy even a small thing like cross-dressing. Nothing is wrong of cross-dressing, it might freak somebody out around you, but as long as you happy who cares right? We live in the free society, so use the resources that it’s available to us. I am very luck that I personally never experienced that I feel like born in the wrong body. I think my personality fit into my biological sex.

    • Hi Shuwen, not every crossdresser feels that he is born in the wrong body or desires a sex change. The reasons we do it vary a lot from one person to the next: a “complex cocktail of motivations”, as the quote at the top of the page says. Some men do wish to become women permanently. Some just like to feel like a woman for a short while and then are happy going back to being men the rest of the time. And some don’t care about becoming or feeling like a woman at all.

      Sometimes I wonder, too, if the men who have a desire to become a woman do so because they exhibit traits that are commonly associated with femininity, such as submissiveness (see the article “Women Are Passive?” also on this blog), nurturing, or whatever and they only wish to become women because it is more socially acceptable for a woman to exhibit those traits than for a man to do so. But that’s just a guess on my part. I can hardly understand what is going on inside my own head, so I surely can’t guess at what goes on in another man’s head!

  5. I don’t know a lot about cross-dressing so thank you Georgia and Vivienne for these insights about what it is like and the challenges. I will have to check out Vivienne’s blog.

  6. Whenever I participate in crossdressing discussions, I make a big deal to emphasize that I am different. “That theory doesn’t apply to me!” I cry. “See? I use a masculine alias. I never wear makeup, or shave, or wear breast prostheses, or get an erection whenever I see/wear/touch feminine garments! I have never contemplated sex change! It’s just a comfort thing for me!”

    And yet… sometimes I wonder. There is absolutely more to it than just preferring skirts and dresses to trousers. Wearing a dress scratches some itch deep within me, and I have very specific preferences. I am attracted to (in no particular order) full-length skirts, long sleeves, high necklines, soft fabrics, ruffles… things you would find in Victorian/Edwarian/Prairie styles. In my childhood I was addicted to the TV show “Little House on the Prairie” because those floor-length homespun dresses with pinafores fascinated me even before it occurred to me to wear them.

    Is there a sexual element that I am repressing out of guilt or shame? Or does my attraction to the modest, exaggerated femininity of bygone eras fill some other psychological need? Maybe I am trying to recapture long-forgotten happier times with an older sister (now deceased) who pampered me. Maybe I long to be freed from the expectations of masculine strength, “demoted” to the meek and subservient role of pre-liberation womanhood. Or maybe, despite all my protests, it’s just a run-of-the-mill fetish. After some 40-plus years agonizing over it, I have given up trying to understand it.

    For now, I figure as long as my proclivities don’t harm my job, my social responsibilities, or my relationship with my family, it represents no harm regardless of the underlying causes and motivations.

    • While it is common for cross-dressers to be attracted to the erotic side of women’s clothing, that doesn’t mean it’s true for everyone. And I’m having a hard time figuring out erotic side of the Victorian/Prairie style. One size doesn’t fit all, as they say.

  7. Is there something of this nature that applies to women who crossdress as men? Of course, masculine fashion has been well-adopted into women’s clothing but there are a number of women out there who deliberately appear maculine( not androgynous).

    • Cross-dressers and transgender people both wear the clothing of the opposite sex, but the motives are a bit different.

      Transgender people don’t feel comfortable with the personality that is assigned to their biological sex. Some feel like they are trapped in the wrong body, while others just push against gender norms.

      Cross-dressers are almost always straight men who have a strong sense of themselves as men. Although as Vivienne says, that could change over time. So while they have a strong sense of themselves as men, they may wear the clothing of the opposite sex to help them get in touch with their more feminine side. And they commonly become aroused by wearing the clothing of the opposite sex, too.

      When women wear the clothing of the opposite sex in a way that is pushing gender boundaries, they are doing so because they are transgender, not because they are cross-dressers.

      And when you look at the other motive – cross-dressers getting turned on – you might notice that the sexy clothing of women is a symbol of sexy. I’m not aware of any clothing men wear that is also a symbol of sexiness. There is no male clothing equivalent of miniskirts, spiked heels, plunging neckline and bras.

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