October 2006
It's been a long time since I wrote this essay and much has happened in my life since then. I no longer identify as a 'crossdresser'. I identify as solidly Transgender, borderline Transsexual - but most specifically as Genderqueer.
I have 'revised' many of my earlier views on things and frankly, I take some exception with what I wrote back in 1997. I do feel, however, it still has merit as it is how most 'textbook' crossdressers (if there is such a thing) continue to see things.
When I started to deal with my trans issues, this is where I was and it's where many, many others start out as well - some never moving from this place. It is for this reason that I leave this posted - almost as a greating to those just coming to grips with all this - as a way of saying, "You're not alone in all of this. There are people who have been there - and they understand."

Crossdressing and Society

By: Donna Lynn Matthews, October 1997

I am (amongst other things) a M2F crossdresser. This means that while my usual gender presentation is as a man, I wear articles of clothing primarily intended for women: panties, bras, slips, camisoles, dresses, skirts, pants, blouses, skirts, sweaters, pantyhose, pumps and boots. I choose the term crossdresser because transvestite carries too much negative connotation with it. As as transgendered person, my crossdressing it is really more an issue of self expression than something I do for kicks.

The many and varied reasons for this can be reduced down to a prime-motivating factor: It gives me a more complete sense if self; I feel more like me. (Don't get me wrong, there is a definite sensual aspect to crossdressing. I like the way women's clothes feel: a flowing skirt against stockinged legs, a silk blouse… it's very sensual. Let's be real, men's clothing just isn't sensual. Functional? Yes. Comfortable? Usually. Sensual? Hardly! But I digress...)

Men's clothing is pretty boring: pants and a shirt, and for business - a suit. The stereotypical business attire: blue suit, white shirt, red tie and black wing tips, and if it's raining: a tan trench coat. It looks like a bunch of clones walking down the street. Women, on the other hand, have a flexibility in dressing of which, to be honest, I am quite envious. With choices of fabrics, color, style and accessories, women's clothing is just more fun. It allows a freedom of self-expression men just do not have. My crossdressing, to whatever extent it may be, helps fills that void.

There is nothing inherently male or female about any one article of clothing. The design of a piece of clothing may favor one or the other (a bra definitely fits a woman better than a man) but it remains nothing more than a specific configuration of cloth, metal, plastic, etc. As a culture, we have chosen to associate certain types and styles of clothing with either men or women.

There are those who feel that crossdressing is unnatural. Well, it is. In fact, the wearing of any clothing is unnatural. We have no genetic predisposition to wearing clothes. Crossdressing is as unnatural as straight dressing. Clothing and the meanings we placed upon is a fabrication of society.

Men used to wear tunics with tights, knickers, ruffled shirts, wigs, heels... the list goes on and on. Try putting on a tunic length top and leggings today... You get the idea. Interestingly though, items such as sarongs and kilts are alright (in certain settings.) Prince Charles has appeared on TV (how appropriate) sporting his kilt while out with his sons.

Women crossdress all the time. They buy men's jeans, shirts and sneakers... even underwear, and they do it without shame or ridicule. In fact, the female crossdresser is considered fashionable. I have read many articles in fashion magazines about how to liven up ones wardrobe by borrowing clothes from your boyfriend, husband, etc. Women's fashions have even copied men's: tuxedo shirts and jackets, boxer shorts, and sport coats are just a few items that have been feminized. It seems clear that women wearing men's clothing (female crossdressing) is socially acceptable.

Men, on the other hand, do not have this freedom. The wearing clothing associated with women is frowned upon by society. Men wearing women's clothing is not socially acceptable and the male crossdresser opens himself to scorn and ridicule almost beyond belief. We are tagged as freaks and misfits: deviants to be avoided. It is immediately assumed that we are either gay (not to insinuate that any of the above labels apply to either the gay or transgendered community as a whole), which is false more times than not, or that we are just mentally disturbed.

The repression feelings is not a good thing, and women who want to express their masculine side are, in general, encouraged to do so. Society as a whole has no problem with women exploring the stereotypically masculine world. Men, on the other hand, are not supposed to have a feminine side. Any man who show interest in stereotypically feminine interests runs the risk of being pigeonholed as above.

Men who crossdress tend to have strong feminine sides that needs to express themself. Whether crossdressed or not, this feminine side is still there, fighting to be heard; although society would rather that it not exist at all.

Can you say Double Standard? Welcome to the life of a crossdresser.

The simple fact is that the majority of men who crossdress are really no different than any other men. They work, have families and basically live like everyone else except they like women's clothes.

Ah, I can hear it now "That's not like everyone else!" Allow me to ask, "How do you know?" Many crossdressers never venture into public. Some who do are better looking than some real women are! Many wear women's underwear on a regular basis. The fact is, if no one told you, you would probably never know. He could be anyone: a drinking buddy, an employee or even your boss.

Anyone, put under close enough scrutiny, would probably reveal something, which could be construed as not fitting in with the societal norm. Yet, we all go about our business not really thinking twice about the person next to us. We are all different, and at the same time similar. The diversity of Mankind is something as yet unsurpassed in the animal kingdom, and is something to be embraced and celebrated. It is our differences which define us, not our similarities.

Crossdressing allows me a freedom of self expression which the confines of society's definition of 'man' just won't allow. And I like that freedom.

It has taken me a long time become comfortable with who I am. I am a crossdresser. And even with all the baggage that comes along with that statement, I wouldn't want change who I am for anything.


  1. I make the following distinction between the terms crossdresser and transvestite:

  2. Male and female, as used here, refer to anatomical differences. Non biological entities can not be male or female. A piece of cloth, no matter how it is configured, is no more male or female than a telephone.

  3. The terms man/men and woman/women are used to refer individuals with a gender presentation usually recognized as 'a man' or 'a woman' by the cisgendered (non-transgendered) community.

  4. Men's and women's clothing refer to articles of clothing traditionally and/or primarily associated with either men or women respectively. Unisex clothing is considered just that: appropriate for both men and women.

Please Note:

The information here is copyright protected and is the exclusive property of Donna Matthews.

Opinions presented here are entirely my own and do not represent the opinions or policy of any other corporate entity.

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