The Dark Side of 

Cross Dressing:

Staying Balanced and Keeping 

Yourself Under Control

By Karen Murphy

Reprinted here with permissions granted

What's the Purpose of This Page?

Why?

Well, the party line in the CD community is that cross dressing is healthy and even therapeutic. It is practiced by ultra-sensitive men who are lucky enough to possess "feminine" souls. CDs dress because it gives their inward female psyches an outward manifestation. Under this view, all problems connected with cross dressing stem from social intolerance. Society is bigoted. If the world were more accepting of human differences and distinctions, and less caught up in arbitrary and nonsensical gender roles, cross dressers wouldn't have any problems at all.

I don't buy the party line and that makes me a heretic.

I think that cross dressing has a "dark side." There are a lot of behaviors connected with it that aren't healthy at all. Aside from being fraught with secrecy, guilt and diminished self-esteem, a CD's life can get out of control. Many CDs become obsessed with their self-feminization. Some lose all sense of judgment, balance, and perspective. Some let their cross dressing jeopardize important personal relationships and responsibilities. Some let the desire to dress turn them into social pariahs who reject the straight world entirely and rely solely on other CDs for companionship, direction, and support. Some CDs come to swim in an exclusive cross dressing milieu. That milieu sometimes exhibits a herd mentality which uses peer pressure to challenge its members to press envelopes and engage in activities that aren't altogether wise or salutary.

This "dark side" of cross dressing isn't discussed much among many members of the CD community. If you do a Web search, you'll find tons of pictures of CDs dressing in various forms of finery. You'll also find lots of links to information on where to get oversized heels, find lingerie, or learn clever strategies for disguising a beard. But you won't find much on dealing with guilt, learning coping skills, or controlling compulsive desires and impulses.

That's why I put up this section. Besides seeking to generate comment about cross dressing's "dark side," I want to use it as a sounding board to focus on practical ways of eliminating or, at least, coping with some of its drawbacks. Ideally, cross dressing should be happy, healthy, and enjoyable. Unfortunately, the problems associated with the "dark side" can make the overall experience quite the opposite.

Now, a disclaimer. I don't pretend to be a professional psychiatrist or therapist. But I'm no ignoramus either. I've been dressing in some form or fashion for over thirty years. That experience has left me with some insights. I've personally seen, experienced, or encountered all of the problems referenced in this section. I know of what I speak.

What's the Problem?

Cross dressing is not a neutral act. A lot happens when a CD puts on women's clothes. Most human societies, ascribe a lot of importance to gender differences. Blue is for boys; pink is for girls. Boys wear pants; girls wear dresses. Snips and snails and puppy dog tails; sugar and spice and everything nice. These gender-based distinctions probably made more sense in non-technological societies. They aren't entirely arbitrary though. Usually, men are physically stronger than women. Usually they are more aggressive and better suited physically and emotionally for competitive pursuits. Women, again speaking generally, are more intuitive and emotional. Women are better fitted physically and emotionally for nurturing and rearing children than most men. Of course, these broad statements are reflective of stereotypes. But, like it or not, gender roles based on such stereotyping have developed in practically all human societies. Once such roles are in place, these same societies usually require all of their members to fit into them, and this is so regardless whether the individual members' particular personalities and physical traits actually conform to the stereotypes on which the assigned gender roles are based.

Clothing is the badge of society's gender distinctions. It is a uniform that tells other members what they can expect from the wearer. Thus, when a male puts on a dress, he also puts himself in contra poise to major societal expectations. Doing that is not without its consequences.

Society imposes sanctions if its members flout the gender roles that have been mapped out for them. If a boy isn't mischievous and venturesome, a parent might encourage him to be more so. If he conforms to the conventional ideal, he is rewarded; if he deviates, he might be talked to, ridiculed, or even punished. You probably understand what I'm driving at.

Well, if our male isn't athletic, aggressive, competitive, or generally "manly" enough, these social sanctions are apt to make him feel guilty, isolated, or diminished. If his non-conformity persists, he will have to deal with resultant feelings of inadequacy and isolation for a long time. Effeminate males do not have an easy time in our society.

A person that crossdresses will have to cope with the same social sanctions and the same resultant feelings -- only more so. A male that cross dresses openly rejects a gender uniform that society has ordained for him. Society will treat this as an act of rebellion and respond with a potent arsenal of opprobrium. As a result, the cross dresser will be made to believe himself weird, perverted, or sick. He will have to deal with social ostracism, guilt, and loss of self-esteem. More importantly, because the cross dresser cannot stop what he is doing, he will made to loathe himself for being weak-willed and different. He will feel extremely isolated and, in fact, will actually be, very much alone.

Guilt, loneliness, isolation, self-loathing, diminished esteem, and feelings of powerlessness in the face of compulsive urges and desires are hard things for most adults to deal with. They are even harder for a child. And that's all the average CD is when he first begins to dress and, as a result, is first confronted with some or all of these problems.

Generally, cross dressing starts right around puberty -- just when young boys become sexual. Dealing with the changes that puberty brings, while simultaneously trying to come to terms with the emotional baggage of cross dressing, is awfully hard. It's a lot to ask of a confused eleven or twelve-year old kid.

This brings us to the subject of cross dressing and sex. They are very closely intertwined. This is something the party line doesn't like to talk about much either. This is a shame, because their connection is really too important to just ignore or sweep under a rug simply because it might make wives or girlfriends nervous or because it's bad for cross dressing's general image.

Cross dressing is not only a symbolic rejection of a socially assigned gender role. It is also a highly sexual act. Most CDs get their start by combining elements of pubescent cross dressing with a great deal of private masturbation. Women's clothing gets brought into the mix because women's "unmentionables" remind young boys of the objects of their budding desires -- women. In our society, having too many sexual thoughts about women is a big no-no. Unfortunately, when a young boy is beginning to explore his sexuality through masturbation, he runs squarely against this taboo. The female clothing he uses as a masturbatory adjunct is mysterious, sexual, and highly associative. It reminds and generally symbolizes for the boy the nameless woman he lusts for, and her forbidden, mysterious, and associated sexuality in particular. Masturbation while wearing women's clothing develops into a repeated script. The clothing adds a visual and tactile aspect to the masturbatory experience that make it more intense, pleasurable, and unforgettable. As humans, we tend to seek out and repeat pleasurable experiences. Because our boy's hormones are raging at puberty, his intensely pleasurable masturbatory cross dressing tends to get repeated a lot.

Unfortunately, America isn't Samoa. Masturbation is almost as big a taboo here as wearing the opposite sex's clothes. The social message is that masturbation is "dirty". It's "sinful". It's just plain "wrong." But our precocious young lad, who has programmed himself to get especially excited by masturbating while wearing his mother's or sister's clothing, is now hit with a societal "double whammy": He's "doubly dirty" because what he is doing violates two major social taboos. Besides touching the wrong body parts, he is also wearing the wrong uniform while doing so. The social felony is thus compounded, and, being a felon, our young cross dresser gets a double dose of the guilt and isolation that society reserves for those who violate its taboos.

So, that's the sexuality of cross dressing. Where is its compulsiveness? Well, lots of women will tell you that males have only one thing in mind. While this is probably an exaggeration, I think most males would admit that sexual desires do take up a great deal of space in their private thoughts. Most would also admit that these thoughts, in turn, often influence their daily behavior. It's awfully hard to repress a male's sexuality. Not many men can do it. As a result, if women aren't around, men tend to masturbate. By the same token, even if women are around, men tend to masturbate.

That said, let's revisit our young boy again. Like other men, he's sexual. This means that he masturbates. Being pubescent, he probably masturbates a lot. Our young boy, however, does it in a novel and unique way. He does it while wearing his sister's panties, with a bit of his mom's lipstick, or while garbed in a pair of stolen pantyhose. With lots of dressed masturbation, he has learned that he can heighten his orgasmic pleasure while employing such items.

So, what happens? As the young boy gets older, his masturbation doesn't stop. His dressing doesn't stop either. His periodic quest for the same heightened pleasure continues. Only now the young man discovers that his pleasure intensifies when new feminine items are added to the masturbatory scenario. These create new prods for his imagination and titillating new masturbatory fantasies are thus fashioned. He might try high heels. He might add a wig. He might even experiment with earrings or false fingernails. Because he equates women with sex, he starts turning his masturbatory sessions into more and more realistic episodes of crossdressing. In doing so, he isn't particularly aroused by the ersatz woman he is creating. Rather, he uses her as a triggering device helpful in conjuring up an imaginary and highly arousing fantasy scenario. This, in turn, stimulates his sexual desires and reintensifies his masturbatory pleasure. The most important thing about all this is that, through this process, our young man, quite unknowingly, is slowly turning himself into a full fledged cross dresser. He will soon find that he can't stop his dressing because he can't stop being sexual. And, owing to his long self-programming, he is only fully sexual when he dresses or fantasizes about doing so.

This too has its consequences. The young CD will begin to feel even more worried and concerned about what he is doing. Not only will he be troubled by the perception that what he is doing is wrong, sinful, or perverted. He will also become increasingly alarmed by his inability to stop.

This is what I mean when I say that cross dressing is compulsive. The cross dresser must dress. He can't stop. He will try to repress his urges. He will throw his masturbatory adjuncts away. He will promise himself that he will stop. He may even succeed for a few weeks or months. But despite his best intentions, he'll eventually do it again. When he does, he will hate himself -- for being weak, for giving in, for lacking control. Despite this self-loathing, he will continue to dress -- and masturbate while dressing -- when he has the time and the privacy to do so.

Once this cycle starts, his cross dressing and his sexuality begin to get even more blurred, muddled, and equated. Dressing begins to intrude on everyday thoughts and desires and increasingly begins to monopolize private or semi-private behavior. Our CD will see an otherwise innocuous advertisement for a dress in the newspaper. Doing so will trigger a fantasy episode involving how he might look in it and how it would feel if he wore it. He will become excited and aroused in the process. Our CD will take off from work, or cut school, just to find private time to dress, and fantasize, at home. He will begin to spend money on clothing and items of women's apparel -- to heighten his arousal and spin new fantasy scenarios -- despite the fact that the money spent is really needed, or could be more productively used, for more useful or important things. He will begin to buy women's things for himself by catalog or in embarrassed forays to drug store cosmetic counters. He will hide his purchases and use them only when he is alone and feels himself safe from discovery. Rapt in a self-induced fantasy and oblivious to consequences, he might even go out in public dressed for short nightly drives or walks -- and risk arrest, exposure, or major humiliation and embarrassment in the process. He might even give his dressed persona a secret feminine name and develop a private fantasy "self" that he brings out for periodic private or public forays "en femme".

These episodes are likely to be followed by periods of genuine remorse. The clothing that has been accumulated will be seen as the source of the sin and will be periodically destroyed or "purged." With new resolve, the CD will again promise himself never to dress again. He will fail, and the whole cycle will repeat itself. The failure will be seen as a lack of resolve and the CD will feel guilty about this and diminished. Ultimately he will just give up and resign himself to being what he is.

What he is, is a cross dresser. He will continue to be one for the rest of his life.

The following pages will address ways of dealing with some of the implications of all this:

For more, click these hyperlinks:

Temperament

THE CHILDHOOD AND FAMILY DYNAMICS OF CROSS DRESSERS

The Real Truth About Cross Dressing