Thursday, January 19, 2012

What He Says... About Cross-dressing

From Wikipedia: Cross-dressing is the act of wearing clothing and other accoutrement commonly associated with a gender within a particular society that is seen as different than the one usually presented by the dresser. It does not, however, necessarily indicate transgender identity; a person who cross-dresses does not always identify as being of a gender other than their assigned gender.

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Stuart Wakefield:
What I don’t understand is that women cross-dress all the time and no one bats an eyelash, but if a man puts on a skirt all hell breaks loose (unless he’s entertaining the breeders). I never really understood why the Jehovah’s Witnesses (with whom I had a book study with as a kid until I was 14) objected to women wearing trousers, but now the pieces are falling into place... Oh, and I dressed as Wonder Woman once and went to the petrol station for camera film. I didn’t dress up as her in order to go out, but I was the only one still sober at the party and it really needed documenting. ;)

Charles Edward:
Not for me, thanks. I wouldn’t have the balls to be caught dead in a dress. But if that’s what another person gets into, more power to him or her. I admire the bravery.
    If I were placed in an ordinary social situation with a dude in a dress and mascara, I believe I’d be uncomfortable — for few minutes. Then I’d deal with it and stop noticing, and do my best to treat the other person with the same dignity as anyone else. Dealing with it and treating others the way you want to be treated is just what adults do.
    It disgusts me that cross-dressers and transpeople are used as such reliable boogeymen for that segment of our society, especially in politics, that professes to know what’s right for everyone else; but what they’re really all about is encouraging grownups to behave like frightened children.

I’m still defining what this means to me. Sometimes wearing lingerie and makeup is like any other sex toy I’ve got. Sometimes it’s a secret I like knowing no one knows about but me. It’s a sexy feeling when I’m alone and get “that look” from my husband when he sees me dressed up, or even when he realizes there’s something silky or lacy just underneath. It used to be the thing that made me feel like an even bigger freak, and it scared the hell out of me to tell my husband anything about it. Now I know I’m loved with or without it and it’s mine and ours and special. Kinky ;) but special.

Edmond Manning:
Waaaay back in college, some of us men on the same dorm floor dressed up as women. I wore a purple sweater dress and pearls. Even at the tender age of 20, I looked like Dustin Hoffman’s Tootsie, but less attractive. I admire those who feel called to express themselves that way, but I don’t think it’s for me. (Going as Snow White for Halloween last year doesn’t count, right? Those black high heels fucking sucked.)

Damon Suede:
I was a song-n-dancer a zillion years ago and did drag a couple times. I passed even because I was long, lean, and leggy (a size 2! LOL) and my face boyish enough to take the paint well. It didn’t do anything for me sexually or socially, but there is a difference in the way folks perceive you when you visually code yourself as female...a weird combination of arousal, deference, and aggression. There’s a power in the costume. Every time, I remember thinking that I understood WHY women went through all this hellish prep with depilation and makeup and byzantine clothing, because there’s a fetishy pleasure in any transformation. But if I had a choice, I’d rather dress up as a satyr or a toothbrush or a doodlebug: no less artificial, no less complicated, and way less restrictive. Dunno. I think any hierarchical role-play generates friction and friction produces power, but I think I have more of a genderfuck impulse than a a real interest in cross-dressing.

D.H. Starr:
My first boyfriend was a cross-dresser and was moderately attractive as a woman, but at home he dressed like a man. It’s an art form to be able to transform oneself and to take on a persona and look that is, to use Damon’s awesome term, “coding” oneself in a different way. That said, I haven’t delved deep enough into the subculture of cross-dressing to really understand it or to have an opinion about it. But I do love to party with men dressed in drag or who are cross-dressers. They tend to be far more interesting and authentic right from the beginning of conversations...once you get past the persona that is.

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Now its your turn to share. What do you think about cross-dressing?

Drop by on February 2nd, when the guys share their thoughts on... Condoms.
And don't forget, if you have any topics, questions or photos you'd like the guys to tackle, just shoot them my way. We'll make sure you get the credit.


  1. What Damon said is right, there is power in the makeup. When I was in high school a group of friends and I all dressed up as the opposite gender for Halloween. I was shocked to see how beautiful my friends Justin and Angel were as women and told them that perhaps they should consider getting a little "snip-snip"? After we rough-housed for even *suggesting* that they do such a thing, I apologized but did let them know how almost flawlessly beautiful they were. Other girls (biological females) were either intimidated or in awe of them. I was also slightly horrified by my friend Ryan's look. He did *not* make a pretty woman. *shudders*

    I think because of my own journey and truth, I'm fascinated by those who cross-dress on a spiritual, deep seeded level. While they don't identify as transgender, these are people who live their truth completely and unashamedly. I find that not just fascinating but extremely beautiful as well. And now that I've babbled on...

    Great answers guys!

  2. Wonderful view points!
    It has never crossed my mind about cross-dressing. I do believe that most of the movies portray it in a "comedy routine" sort of way but I have seen some of guys who look as beautiful as a woman does when made up. I have been awestruck by them. I envy and admire the confidence to carry themselves.

    Some of the beautiful drags I have seen on television were in Queer as Folk - Emmet's drag when he crashes Michael and David's party for the senator and then Michael for the Pride Parade. Wonderfully done. Plus some of the drag queens in the clubs scenes just blew my mind away!

  3. My philosophy has always been (and I apologize to Wiccans for the rough paraphrase): If it doesn't hurt anybody, do whatever you want!

  4. If you like it, if it makes you feel good or fun, or just to be a different person for a while, go for it! Sometimes wearing something sexy underneath regular clothes gives a person a lift and a confidence. (And since there are fewer sexy/silky things for guys why not go for womens'?) Cross-dressing in whichever way should be just another option. Although I wonder if a little of the fun would be lost, if all clothes really were appropriate for all genders and the gender transformational effect of cross-dressing disappeared. Guys? If it was just "pretty clothes" and not "women's pretty clothes" would it appeal less? Or more?

  5. Well, mine is from a woman's point of view here and as a woman who frequents a gay bar that does a lot of drag shows. While I don't get the whole idea of caking on make up and putting on eyelashes that are an inch long, I can understand the reasoning behind it. I have come to love both the performers and the men themselves. They are some really great people. As for men in general just wearing sexy women's underwear, like Thorny, or even just dressing and looking like a woman, there's nothing wrong with that. I actually look up to and admire those who can and do. But Damon, a toothbrush and a doodlebug, really. Its a damn good thing I wasnt eating when I read that, because I would have choked, lol. Love you sweetie:-)

  6. Now I want to dress up as a man—not just wear jeans and a t-shirt, intentionally pass myself off as a man—and see what happens. I've unintentionally passed as a man (boy, actually) a lot because of a traditionally male job I had and my short hair. I'm intrigued by Damon's comments about the disparity and power imbalance.

    But yeah, being a woman wearing the right thing has gotten me a lot of things in life I know I wouldn't have if I were a man. Just sayin'.

    Personally, I find it kind of hot when men wear women't lingerie. Don't tell my husband, he'll freak.

  7. Kaje, I like your question!

    I *love* me some pretty clothes. Years ago, I attended a HRC's fundraising bash as a guest and my date and I rented tuxedos. I loved wearing a tuxedo...I felt delicious, powerful, silly, special. I loved wearing a cumberbun and bow tie. Golden cuff links.

    The kings in my novel, King Perry, wear a special, sparkling, radiant shirt as they greet the dawn. Pretty clothes! Pretty clothes!

    I do think men who wear womens' clothes play a powerful role in shifting cultural views. I get irritated by gay guys who look at men in drag and think, 'Disgusting.' Hey, those "disgusting" drag queens were the first ones to say NO MORE at Stone Wall. They choose to live on the front-lines of prejudice and name-calling and why? Because it's their *truth.* Because their soul says, "Baby, I'd look good in a strapless." They deserve our admiration. (And possibly a cosmo.)

    I integrate drag queens into my books, at least as a cameo, trying to give them a role of power.


  8. Hi, everybody! :) LC, thanks for the pic beside my answer -- yummy! Very Valentine's ;)

    Kaje, I kind of don't think of the clothes I wear (alone or under something else) as girl clothes because I buy the majority from an online store that makes them FOR MEN. It's sized for me and made to fit my chest, hips, and especially my boy bits. So they're pretty boy clothes to me.

    Of course, I didn't always think this way and that's part of what screwed with my head. Don't want to be a girl, so why the heck am I wearing girl clothes?! I had to separate that, I guess. Or there's probably some psychological something or other going on that I've made peace with even if I don't have the words.

    I agree with Edmond, too. I have a tailored suit that makes me feel like sex on a stick! It's a lovely charcoal gray all fitted to me in every way and I wear it with pastel shirts and ties...and once with pumps. You can see the steam, I'm so hot! :D At least, that's how I feel in it.

  9. I'm not a fan of highly patterned fabrics or anything with a sheen so I doubt I'd ever purchase something "pretty".

    Right now, I prefer an industrial look, choosing G-Star and Police brands. You'll find me in boots, twisted chinos, checked shirts, and denim jackets this season.


  10. I totally agree with Stuart. I am not sure why it is a big deal for men to wear feminine clothes/makeup, but no one thinks twice if women wear more traditionally masculine clothes. Personally, I love a little eyeliner and makeup on a guy (although I don't think my husband would go for it). And I agree with Thorny, I love the thrill when my husband realizes I have something sexy or lacy on under my regular clothes. Why wouldn't a guy like that too?

  11. I like it when people dare to stand out and I love to see cross dressers. It can be sexy, interesting, silly, over the top or very vulnerable. I love and admire it.

  12. Great topic!

    I always thought my hubby was "femmy" until I dressed him up in my lingerie one night. Those frilly things really made his masculinity pop!

    I find it unfortunate that I have way too much boobage to convincingly cross-dress. But I have decided that I will be fitted for a tuxedo the next time I have to attend a formal occasion.

  13. Great answers everyone! I think its awesome when people, men or women, have the courage to wear whatever they feel most comfortable in. Its funny that I only wear dresses if I have to because heels are just torture devices to me...LOL.

  14. I'm with Amanda! On all of it, espcially about people doing what makes them happy and comfortable (NOT what makes others comfortable. I've dealt with *that* with friends over the "breastfeeding in public" issue). I also think heels are torture devices. DH says they're not so much sexy b/c he's always worried about my klutzy self managing to trip over my own toes and break an ankle.

    Oh, and I hate bras, with the passion of a thousand fiery suns. But there comes a point for some of us when they're not really optional anymore.

  15. I say that anyone who feels like dressing up as either male or female by all means do so. My sweetheart does it every halloween and he enjoys it. I have yet to see this but I love him. I just think that people should live their truths.

    I don't know what else to say. I've seen some very great men dress up as a woman and most of them looked amazing. Can't wait to see my sweetheart though because it's something we've talked about.

    ~Blows kisses and sprinkles dust around and disappears~

  16. Thanks for dropping by everyone! I'm loving all your comments. I say, wear whatever makes you feel good and own it.

    @Brahmin - "I have seen some of guys who look as beautiful as a woman does when made up. I have been awestruck by them."

    I am right there with you! Last summer I was in line at a coffee shop, turned around and my jaw dropped. There stood over six feet of beautiful black man in a tank-style leopard print mini dress and stilettos. And she was effing gorgeous! At the time I remember thinking, "So. Not. Fair..." I might have said it out loud. ;-)

    @Edmond & Thorny - I love the sleekness of wearing a well tailored tux too. With long tails. (I thought you might like that picture, Sunshine. *g*)

    1. I used to see a woman travelling in the same bus as I was and I was curious about the foundation that she used to wear as it had excellent coverage - this was during the winters.

      It was couple of months later I found out (when it was summer and the dresses came out) that it was a guy! The bone structure gave her away! After that I might have embarrassed myself staring at the beautifully applied make-up. Oh I can still see those pretty eye-shadow colors... *sigh*

  17. I admire anyone willing to do it, and I love the guys who can really wear it well! There are some awesome guy cosplayers who look great in it! (I was floored by one cutie last year, and he's a regular at the con, so I hope to see him again this year.) =)

  18. Great article idea and I love all the different perspectives!

    However, a couple saying that "no one thinks twice" if a woman dresses as a man? In my experience, not true. The confusion might arise because when a woman dresses in baggy jeans and a loose shirt that does NOT mean "dressing as a man". In fact a lot of stores sell "boyfriend" clothes to women that make it explicitly feminine to wear certain types of loose shirts and pants.

    I'm a woman who has worn mens clothing on and off in public since I was a teenager, and it takes a fair amount of effort and planning to wear real mens clothing in a gender-neutral or masculine fashion.

    Dressing as a man gives you a certain exhilarating freedom (people don't look at you as hard or treat you as such a visual object) BUT it can also expose you to hostile attention. I've had people yell at me randomly in public (like on buses) because they felt "tricked" when I looked just like a man but sounded like a woman when I opened my mouth. And someone threaten to beat me up in the Bahamas for the crime of... looking androgynous while buying groceries. That episode almost literally scared the pants off me.

    I'm pretty sure the group that receives more physical violence than any other group are transgender women, and that's always something to remember. But gender codes get enforced all around, under the radar. I'm neither trans nor a serious cross-dresser but I have a lot of respect for people who are... it's not easy!

    1. Oh, Violetta, how horrid to hear that you have been threatened for that!

  19. A few years ago I was a 300 lbs woman living in Houston, in the summer. It was FUCKING HOT. I spent the first 30+ years of my life avoiding dresses whenever possible, because I hated how uncomfortable they were and all the maintenance and baggage that went with them. But like I said, it was fucking hot, and if I had to walk out the front door one more time in jeans, I was going to die.

    I felt like I was in drag when I first started wearing them. Like I had to create a whole new persona. Like everyone was going to look at me and know... something. I don't know what. It wasn't just pulling on a floaty cotton skirt instead of jeans. It took a while for me to wrap my head around it. Now it's no big, but it was weird for the first couple of months.

    It's awesome to see a guy who looks really beautiful in drag, but I think I have even more respect for the guys who can't pull off traditional beauty but do it anyway.

  20. Wonderful topic, very enlightening to see everyone's opinions and thoughts.

    I find Thorny's comment, "You can see the steam, I'm so hot! :D At least, that's how I feel in it.", to be the measure of what to wear and why.

    I know how titillating it is when I'm wearing sexy underwear (or not wearing any), both for me and my hubby. Whether you decide to cross-dress in public--which takes a lot of guts, IMO--or in private, it's how it makes YOU feel that matters. Wear what makes you feel good.

    Love this blog and column, thanks L.C.!

  21. Hey Stewart, here is how I see it. After we women had been barred from men's clothing--and so many other things--for like forever, we took your trousers for ourselves. I say, you should do the same with skirts. I'm all for it--I want to see some legs.