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.

Grayson Perry longs to fully express his whole self, including his sensitive, sexy, playful, submissive, expressive, and vulnerable sides, which men aren’t really allowed to show.

The yearning is understandable. When Norah Vincent cross-dressed as a man to enter the world of masculine privilege for 18 months, she felt like she was wearing an emotional straight jacket. As she recalled in her book Self-Made Man,

Living as a man taught me a lot about the things I most enjoyed about being a woman in the world, things I consider to be the privileges of womanhood – the emotional freedom, the range of expression…

I don’t miss anything about being “Ned.” The few social advantages I’ve discovered in manhood – the swagger, the self-confidence, entitlement – I’ve learned to incorporate into my life as a woman. Everything else I was happy to discard.

Male characteristics are not demeaned and so women can easily take them on without shame. Men are denied that flexibility. So some men transform into women thru costume and makeup in hopes of touching that other side.

But the brief transformation does not fully satisfy. Perry continues:

When I’m out dressed, it’s good enough, but often I come home thinking… at my core level I’m a little bit unsatisfied with the experience… I think it’s painful that we do invest such a lot of emotion in often rather brief glimpses of…happiness.

Vivienne of Bluestocking Blue

Vivienne of Bluestocking Blue

Cross-dresser, Vivienne can relate. While discussing Grayson Perry on her blog she reflects,

The rational part of my brain asks, as I am dressing: what possible benefit from this activity could there be? It doesn’t solve any problems. It doesn’t change anything. Meanwhile the emotional part of my brain says: because it feels absolutely wonderful, it relaxes me, it alleviates my stresses. And afterwards, instead of just looking back and enjoying it, I usually feel a little bit guilty. I am forced to agree with Perry that, deep down, cross-dressing is a slightly unsatisfying activity…

I think that there is certainly an element of shame and stigma about cross-dressing (hence the guilt). It also upsets my wife and causes stress in our marriage. My feelings about cross-dressing wax and wane…


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

For more on the experience of cross-dressing and its motives, go to BluestockingBlue, and particularly her series on the documentary,  “Why men wear frocks.”

Related Posts on BroadBlogs
Men Who Wear Frocks
Women Get All The Good Emotions, Says Cross-Dresser
How I’m Seen Differently in a Female Body

About BroadBlogs

I have a Ph.D. from UCLA in sociology (emphasis: gender, social psych, women's 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 University. And I have blogged for Ms. Magazine, The Good Men Project and Daily Kos.

Posted on June 6, 2014, in feminism, gender, LGBTQ, men, psychology, sexism and tagged , , , , , , , , . Bookmark the permalink. 42 Comments.

  1. This is very interesting. I look at how some young women behave, and then just imagine a man behaving like that, and it does seem it would be very odd/’gay’. The reverse, not so much. It’s ironic, that while women are portrayed as the ‘responsible ones’, they are also (moreso in the past) portrayed as flitty, ditzy, and sort of childish, gigging, squealing and ‘falling all over the place.’ This is no better seen than on say a hen’s night or a girl’s night out when they’re dressed in revealing outfits and high heels. Alcohol may be involved, but it tends to silliness. I think a lot of cross-dressing acts allow men that same freedom as that sort of behaviour is usually demeaned by the ‘responsible’ patriarchal culture.

    • Always interesting when contradictions are pointed out like women as “responsible” or “flirty” — while men are only allowed the first (and not always that). Women are allowed a wider range of expression ironically because they are gender ranked lower, so don’t have to uphold some standard of womanhood.

      • Actually, I’m not sure women are necessarily allowed a wider range of expression. Like it’s been said that since they are very young girls are discouraged from being angry, raucous or rough. And it got me thinking about the whole idea of women being stereotypically seen as not funny (not sure if you’ve read the famous Christopher Hitchens article). I actually think women in some social situations are also expected to be passive, and be the ones to react, rather than the pro-active causers of things, although things might evening out. Btw I never thought women were any less funny, but that they were sometimes encouraged not to let that side out, especially in the company of men. I’ve always noticed women who tend to fuss less about their appearance tend to have a more ‘easy’ manner and a more natural sense of humour. Perhaps a good topic for another blog post (just a suggestion)?

      • It’s true that women are repressed in some ways too — less angry, aggressive, comedic — but that still leaves them with a much wider range of expression then men are allowed.

        I wonder if the comedic side is repressed in attractive women because it doesn’t go well with being seen as a sex object. That whole side of herself becomes a distraction from “Sexy.”

      • Maybe the man doesn’t want her to upstage him? Personally I find humour in a woman, both one that can appreciate a wide variety of humour and is funny, is an under appreciated trait and one I find very attractive. Many men definitely do appreciate women for their personality alot more than they’re given credit for.

      • That makes sense–the fear of being upstaged–in terms of interpersonal relationships. But even women who make a living out of being comedians can find some pushback. Maybe much less so today than in the past. Tina Fey seems to be pretty accepted, for example.

  2. Aha, my favorite topic returns. I can chime in from my own experience, and from discussions with other folks who fall into the amorphous “trans” part of LGBT.

    I know without a doubt that my masculinity is questioned any time I stray from the established cultural norms, even when my peculiar choice of clothing isn’t known. I love Broadway musicals and sing along with them. I fear confrontation, always backing down in a fight. I loathe physically demanding activities like sports and hunting and fishing. I have a strong nurturing instinct. I walk and stand with an inner peace, holding my limbs at relaxed angles, rather than the exuberant swagger of a confident man Most of my spare time is spent either on social networks — where most of my friends are women, because their husbands won’t have anything to do with it. Or playing virtual reality games like Second Life, where I put in an extraordinary amount of time tinkering with my appearance and doing other imagination-laden stuff. I could just imagine my rancher friends, men and women, hearing that I spent the weekend dressing up a female avatar so she’ll make friends more easily in chat areas. I write and talk at length about my cat and worry over his health and safety.

    So yeah, much of my personality (the part that doesn’t watch “Lethal Weapon” and other ridiculously violent movies, or throw dirty clothes in a pile on the floor, or pick my nose in public, or fail to bathe for days on end because I’m not going out so who would notice anyhow) absolutely screams “effeminate!” One of my friends actually joked about me wearing a dress in response to something I said that apparently wasn’t manly enough. Oh, if she only knew…

    PS – when I saw the topic title I thought it would be about the odd connection I’ve seen between men who enjoy crossdressing and men who enjoy BDSM. It’s surprising how much overlap there is between the two groups.

    • Oh yeah, I can see how you could get that connection now. I’m assuming that guys would be playing the submissive role in that case.

      If men were able to express themselves in the same way that women are, I wonder if you would see yourself as trans at all? Because women can do and awful lot of so-called masculine things and still have a strong identity as female.

    • I love Broadway musicals, but because I’m a music lover. Anyone who thinks it says anything definitely about your sexuality is controlled by simple-minded stereotypes.

  3. So interesting. I never thought what might compel cross-dressers much. I don’t know why it wouldn’t be obvious that it can be complex and sometimes conflicting for those who do cross-dress even with the pleasures. Thank you for shining some light on this.

  4. It’s good for men to have the freedom. But men aren’t women and women aren’t men. You can say conidtion does so much, but men and women aren’t the same. So without culture and conditioning, men and women would be close to the same with how they express and men being equally feminine acting and physically and women equally masculine to their feminine side? I’m sure there’s nature involved too with wome being more feminine and men more masculine in behaviour too.

    Then I have to ask since you bring up how society definine men and women and you seem pretty open minded about this. So you truly wouldn’t care or be bothered if your SO if you have one or future man wanted to dress as a woman and did, in private and in public? I doubt it wouldn’t be weird to you and I’m sure it wouldn’t be attractive either. Forget the feminine acting side, but men in women’s clothes, that’s just hard on the eyes. I know it sounds biased since i’m a straight man, but it seems more straight women see it that way too.

    Maybe conditioning, but then again, the male body just looks silly just because of anatomy. Women’s clothes are made for bodies that have curves (breasts, legs hips), smaller body and bone structure. EVen smaller men are generally broader, well hairier too, and just bigger body structure. So even if a man is shaved, his body doesn’t look right in smaller frilly clothes. It’s like a big hulking gorilla wearing a tiny tutu.

    • Whether or not I would want to be married to a cross-dresser is beside the point here. My point is that men aren’t allowed to express their full selves, and some turn to cross-dressing as a release. From listening to actors I can see how that could be helpful. Some have said that they couldn’t get into their character until they put the costume on. And to the extent that they can pass, they can really experience the feminine side of themselves.

      When you look at our stereotypes about the traits that men and women have, and then compare that to real-life, you will find that women are much more likely to express what are considered masculine traits. Take something like aggression. I know a lot of women who are more aggressive than their male counterparts. I’m more aggressive than my brother, my mom is more aggressive than my dad, my husband’s mom is more aggressive than his dad. Plenty of people have had that experience. Plenty of women are strong leaders, active agents of their lives, interested in science, breadwinners, Etc.

      That’s because men are ranked higher than women and so when women take on masculine roles and traits, no one sees them as demeaning themselves. But when men take on feminine traits, they are more likely to get a lot of pushback. Men who are passive, followers, stay at home dads instead of breadwinners, emotional, and who care about fashion, can take a lot of punishment. And so guys often repress that side of themselves.

      My hope is that the world can change so that men can comfortably express their whole humanity. Then they wouldn’t have to cross-dress to do it. But if some guys still want to, fine, I don’t see that it’s a big deal.

      As to how men look in skirts and dresses, men have worn them in many times and places. There’s the Scottish kilt, Roman warriors wore skirts (armored), Jesus wore a dress. Romeo wore tights. See this:

      http://broadblogs.com/2011/03/11/my-son-likes-girl-things-is-he-gay/

    • ‘The male body just looks silly because of anatomy.’ Silly, or silly in clothes designed for women? Sure clothes are designed for women, but even among women there is a wide variety of body types, so some women with a more masculine build might also look funny in a dress or something. Yes men are generally hairier, but a lot aren’t too. There’s also variation in ethnicity. East Asian men are often less hairy overall than South Asian women in terms of body hair.

  5. Yeah but the armored aspect, and kilts, they still have a masculine look to them, which is why even thought they are “skirts” they don’t look like skirts. The whole suit and armor adds the masculine edge. Women’s clothes or what cross dressers wear are very feminine clothes. Those ones worn by such examples, the clothes were built for a masculine build, the color and design masculine so not feminine looking. Plus the colonial people wore stockings, I mean benjamin franklin, george washington, they had wigs and stockings, but while not overly masculine they still looked like guys. The cross dressers they wear clothes from women and the make up is done to look like a woman, they try to dress and look like a woman which is why it’s seen weird.

    Women can wear more masculine clothes and be more masculine in behaviour howerver these is a limit to that too. Just like men dressign and trying to look feminine seem weird. Women though not to the same level as men, can look weird or funny cross dressing too. A women with her hair done and clothes like a guy, androgenous looking or really dressed and hair like a guy can look “butch”. She’ll get looks too, if she starts looking like a man or boy or masculine as a result too. Actually while men get seen harsher for cross dressing as women.

    When it relating to looks, a man is allowed to “look” like a woman as long as he’s not trying to cross dress, whereas, women unfortunatley can be seen as very unattractive and less feminine and manly if she “looks” like a guy and has a masculine or manly face. Some women sadly can have manly like faces without trying, add that to guy clothes and you get that. Some women have the square jaw line, and broad facial features that guys usually have the differentiate with men and women’s faces.

    • When people aren’t used to seeing something, especially when they associate it with something else–like the opposite sex — it always looks strange.

      Kilts are masculine? My mom and I have both worn skirts that looked exactly like kilts — the design was inspired by them.

      Nothing is inherently masculine/feminine. Did you see the pics I linked to?

    • They’re masculine or feminine because of association. It is the social ‘gender’ that cross-dressers want to embrace more than anything. They still look like guys because you have been identifying them as guys for your entire life.

      Yes, of course. Anyone who wears gender atypical clothing is singled out in this society. Clothing is still not really unisex for the most part. To take an example, swimsuits were more unisex in the 1930s than now.

  6. For example, look at the glam rock guys, they weren’t seen in a bad way even though some looked feminine or like girls. The singers from Hanson, jeesh, talk about girly looking and they werent really trying too. Their faces with the long blonde hair, etc just made them look pretty feminine in appearance.

  7. Erica Dalton

    This outlook on cross dressing helped to me to understand what the benefits of cross dressing are. Norah Vincent’s quote sums it up perfectly. It’s the lack of emotional freedom of being a man that drives these particular males to search for a way to express themselves. It makes sense why these cross dressing men are often straight and in relationships. It now seems to me that it’s really not about sexuality but comfort in ones self and the ability to express their emotions. Unfortunately that’s not how most see it, but it makes sense. One thing I never considered though is the pain that comes along with it. Cross dressing comes off seeming like a fun event that men (and a few women) can cross the barrier of gender roles and have fun with others who enjoy the same freedom. I feel naive though for never have considered the pain it takes to actually feel comfortable enough with their desires to take the steps to start to cross dressing and the pain it feels to have to return to everyday life post event. It’s sad to hear that some men can only achieve the freedom they need by in small portions of their life, and often with consequence.

  8. I’ve always thought it was stupid how a girl could more or less show interests in ‘boy’ hobbies and be accepted, but if a boy shows interests in girl activities, his sexuality is all of a sudden up to public speculation. Sometimes I think the next step in gender equality is the acceptance of men who display stereotypically feminine traits.

    • I think it’s an important one.

      And the most obvious way to get there is to see women as equals. The main reason men aren’t allowed the full spectrum of expression is because they are seen as demeaning themselves by taking on feminine characteristics. If feminine and masculine characteristics were seen as equal, then everyone could express their full selves, and not have to repress vital parts of their humanity.

      • There have been times when I wanted to do something, but my wife would tell me no because I’m a guy. I would respond that she did something or other traditionally male and I said nothing. Her typical response is “It’s different for women”.

      • Sounds about right. Too bad about that.

  9. “Long blonde hair’ is a cue associated with femininity, that’s why we see it as ‘feminine.’ If it were not so, and say women were the ones who wore their hair short and men long, we might even think of short hair as feminine.”

    No because it’s a sign of youth with women and their hair long. I think that’s why men like and are attracted to women with long hair. As when women are young they have the locks to grow hair out well. Notice how women as they are 45 and older, their hair may not be “short” but it’s not long like when they were in their teens up to 30s?

    It’s more so than hair though, nelson just had feminine faces to go with the hair. Look at this pic http://beatcrave.com/wp-content/uploads/2010/07/the-nelson-brothers.jpg

    And look at this rocker who had long blonde hair too and he definitely looks like a dude ha

    • Pretty much no one past puberty has blond hair, So it’s a sign prepubescence, not the sign of someone who is sexually available.

      However, symbolically we have created a completely different idea about what blond hair means.

  10. I agree, i find that when girls show more masculine traits it is more accepted, but when boys act or dress more feminine through the use of makeup, clothes, hair etc. they are automatically thought of as gay. It is very interesting to see how society views masculinity vs. femininity in terms of dressing, and how one’s outer appearance leads to people making assumptions.

  11. norimasa0311

    I think everyone can agree with the opinion that if women act or wear like men in this society, it is normal usually. On the other hand, if men do that, it is really strange or awkward. I think this is chaotic for me. For this situation, I think that men produce this chaos by themselves. According to this article, men are rejected the flexibility of behavior. In this inflexible society, I think if men wear women clothes or pretend to be women, they always feel unsatisfied because a part of brain perceive this is odd unconsciously even though they really want to know what real women are.

  12. I brought up blonde hair because it was brought up, but should’ve said long hair. That’s what I mean, that’s a sign of youth and fertility though, long hair that is brown or red head or dirty blonde, light brownish hair. Long shiny hair is a sign of youth, health, and in essence fertility. That’s why said person can’t compare how we see long hair as femine and that if women had short hair it would be femine and if men had long hair masculine. Because long hair is seen as feminine, because it’s a sign of health and youth, healthy hair.

    Men typically even with a full head of hair can’t grow out their hair like women or it’s for a very short period. I’m bald now, but evem when, I cou;dn’t have long hair. The glam rock or hippy gus are the exception, plus guys are more apt to go bald or receding hairline or to a greater level. Shorter hair naturally is seen as masculine as men are the one’s whose hairline generally is limited unlike women. ‘m seeing more and more guys lose their hair in their mid 20s these days. I did, luckily I have the face and round head with it buzzed that it looks good for me.

    • Well, I don’t know. Do younger women necessarily have naturally longer hair? In the 50s short hair was all the rage: Marilyn Monroe, Elizabeth Taylor, Doris Day…

      And guys with long hair can be pretty hot. Andre Agassi was really hot with long hair, for instance.

  13. Jelissa Blanco

    In my opinion I don’t think it’s okay for men to cross dress and still be with a women. Maybe the norms play a lot into why I think that. But I just think it’s odd and if it was me and my boyfriend or husband would want to cross dress it would make me feel really uncomfortable. It would make me think he was gay or confused. I just don’t think is normal. I feel there are other ways for men to find a release. But like I said I think the way society has set the norms it plays a big role into my way of thinking. As some people do agree with what I’m saying.

  14. I find cross dressing to be something fairly odd in my point of view, therefore I have to understand the why before i can compose an opinion. Now that I have read this article and even looked up some other resources I can say that for some people like the article quotes, “Grayson Perry longs to fully express his whole self, including his sensitive, sexy, playful, submissive, expressive, and vulnerable sides, which men aren’t really allowed to show.”.
    That cross dressing here in Grayson Perry’s situation is a form of expression, a tool to actually express yourself without hiding your most intimate feelings. In other cases it maybe a way just to have fun, while for others cross dressing can be the beginning of becoming a transgender individual. That is the case of Renee Richards, before known as Richard Raskin, a former Doctor and renowned tennis player that after many years of cross dressing about three decades actually, began the transition to becoming a female, and following her now dreams. She went through a lot of pain in the media, and within her own personal life. Being an ex-naval soldier she was a tough cookie, she brought to light many of the big issues that we today have as national topics. With her life being a prime example it is obvious that cross dressing is definitely a bringer of pleasure and pain. No matter the reason for which you do it, it is appearant that cross dressing is a part of human expression no matter how minute they are in the expressed in the population.

    • Yeah, she was similar but also different in that she saw herself as female. Cross-dressers see themselves as men who are unable to express important parts of themselves.

  15. For a while I’ve wanted to feel ‘sexy,’ but I somehow don’t feel that cross-dressing would create that feeling. Perhaps it is a self-image issue, or perhaps it is a social feedback problem, but whatever the cause I find myself only experiencing such things in a reflective system: I have to think that someone else thinks I’m ‘sexy’ in order to feel it about myself. It’s rather crippling.

    I have no problem with cross-dressing, though. It seems a little disconcerting when I observe it in person, but it doesn’t bother me. I figure I wouldn’t bat an eyelash at it if it were commonplace.

    Speaking of which, there is an RPG that I run for a group of my friends called “Shadowrun,” you might find the social fiction of it intriguing. It’s set in the near future when humanity has embraced all forms of gender; the term ‘cross-dressing’ isn’t even in common use any more because people wear whatever they want.

    Shadowrun’s commentary is somewhat cynical though; it seems to say that humanity cannot exist in perfect harmony. We cannot overcome one social issue without encountering (or perhaps creating) another. Regardless, I thought it was interesting and relevant!

    • Sounds interesting. Thanks for the suggestion.

      And sure, not all men will feel sexy wearing women’s clothing. Most men would probably feel ridiculous. And yet that can be one of the motivations among cross-dressers.

  16. I think its good idea to wear cross-dressing once in a while which makes those people feel the other side of gender. At the same time if that particular person is gay or leabian which will they reall feel themselves.It not to bad to experience something like this. Life is full of experiences.

    • Well, typically it’s straight men who cross-dress. Maybe that’s because gay men are already allowed much more expression. Since they are already going against gender norms sexually, they are less likely to feel pressure to repress themselves emotionally in order to constantly show themselves to be so-called real men. And women can pretty much express themselves however they want, Whether they are lesbian or straight. They can be socialized to not show anger — but this is less strong socialization and many women show anger, anyway.

  17. In this society, it is perfectly normal for women to dress in ways appropriate for both male and female in casual settings. A girl can wear jeans and a t-shirt anyway. On the other hand, males are expected to stick with an arbitrary standard of masculinity even when dressing themselves. For example, for a man to wear a skirt is considered abnormal. It’s because of this that I was somehow surprised to think that women cross-dress. What does that actually entail? Even more interesting than the social standards are the emotional effects cross dressing has on these individuals. I think it would be quite an intriguing experience to attempt cross-dressing myself one day. I am curious as to the effects it might have on me. Would I feel liberated to some extent?

  18. It is pretty shocking how it is considered normal and acceptable for women to dress like women but when men try to dress like women they are criticized and judged. Its not very fair for men. They should also be allowed to express their feminim side just like women are “told” to show their masculine side. This can also be portrayed in emotions and personalities. Men should be allowed to have an emotional side just like women are allowed to.

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