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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.  Read the rest of this entry

Men Wearing Dresses to Feel Whole



All I want to do is to be able to be myself every day.

That’s from “Vivienne,” a man who cross-dresses in part to get in touch with his feminine side and feel whole.

Wearing a dress helps in the same way that actors use costume to get into a part.

But it’s unsatisfactory, he says.  Read the rest of this entry

Cross-Dressing Pleasure and Pain

Miss Rose Beauty Pageant

Miss Rose Beauty Pageant

Musing on the enchantments of the cross-dressing “Miss Rose Beauty Pageant,” artist and transvestite, Grayson Perry opines,

That’s when the fantasies take flight… (but also) I thought: ooh, there’s a lot of pain in this room…They were doing their best to meet their own very emotional needs…

I slightly cringe when people say “Oh, it’s just a bit of fun,” because these guys are risking often their marriages, their careers, their relationship with their children and their neighbors — not to mention their bank balance sometimes, with the size of their wardrobes.

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Women Get All The Good Emotions, Says Cross-Dresser

HAY FESTIVAL 2004.I think it’s quite hard for men today, because there’s an increasingly narrow bandwidth of behaviors which are seen as exclusively masculine. As women have quite rightly encroached on what used to be seen as male territory, all that’s left is the negative things. There’s less scope for a sensitive man to feel at home. What kind of men do we actually want boys to become?

That’s British artist and cross-dresser, Grayson Perry. We met him earlier in a discussion on “Men Who Wear Frocks.” He wears dresses, he says, because they help him get in touch with the feminine side of his humanity, which is blocked by a culture that suppresses male emotion.

imagesHere’s how Perry explains that process of female “encroachment” into (so-called) male territory:

Until the later part of the 19th century, cross-dressing in ordinary life was an overwhelmingly female to male activity. Typically it tended to be a woman just trying to get on in a man’s world. But in the Victorian age, the traffic started to switch direction. Since then transvestism has become an overwhelmingly male to female behavior.

As the Victorians increasingly corralled all the softer emotions, vulnerability, innocence, gentleness, beauty into an exclusively feminine realm, men were cast as stoical, butch, practical providers, and dressed accordingly. Is it any wonder that some men started to want to cross over? For me, what the Victorians wore is the most striking example of how clothes can come to symbolize complex emotions.

So women started out more apt to mimic men in order to grasp greater opportunity and self-expression. Not to mention, gaining the status and privilege of the masculine world.

These days, women commonly express a whole range of so-called masculine traits and activities without being seen as crossing gender boundaries. They’re just doing “people-stuff.”

But men have not taken on feminine traits and activities to the same degree. Not because they can’t, but because they mostly won’t.

Why not?

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Men Who Wear Frocks

Some guys wear dresses. Why? 



“Vivienne” is what one cross-dressing man calls himself when he’s in drag. Vivienne also blogs on her cross-dressing experience over at BluestockingBlue, where she seeks to understand why she does it.

Before delving into Vivienne’s musings, let’s do a little Transvestite 101.

First, you might be surprised to learn that most cross-dressers, a.k.a. transvestites, are straight men.

Straight men?

While biological males who are transgendered or transsexual don’t see themselves as men, transvestites do. They are men who are trying to express something of the feminine within, which is so often submerged. And, cross-dressing often holds a sexual appeal for them.

That appeal helps explain why they’re usually straight. These guys are turned-on by women, and for them, dressing like one can be arousing.

Now back to Vivienne, who wrote a four-part series on a documentary called “Why Men Wear Frocks.” The film was produced by British artist, and tranny,  Grayson Perry. To read more, start with Part 1 on her site.

Read the rest of this entry

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