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Insight to a Crossdresser

For those of you who may be new to the transgender, and crossdressers in particular, this article will hopefully provide some insight about crossdressers.

I am a crossdresser - or at least that is a good way to describe me. Crossdressers are considered part of the broad spectrum of people that we term as being "transgender."

By most accounts, I am a normal person who leads a fairly ordinary life - as do most crossdressers. At the time of this writing, I am in my early forties. I have a loving, supportive wife and with whom I have beautiful children. I live in an upper-middle class neighborhood. I have earned a couple college degrees and some technical certifications for my career. For the most part, my hobbies and interests are little different from many others my age except that I regularly like to dress up in women's clothes and present myself as a woman.

In order to help you understand crossdressers, I'll answer some personal questions here. Sometimes painful for me to provide, these answers are my own and they are honest. These answers may or may not be same as other peoples. Still, I suspect that there will be quite a few similarities between my answers and the answers of other crossdressers.

Have I always crossdressed?
I have been dressing as a female, in varying degrees, since I was very young. I don't remember any exact dates but I do recall that, even as a preschooler, I would often pretend that I was a girl. As a young child, I would dress in some of my mom's clothes and even donned her then-stylish wig or I would secretly borrow clothes from my sisters.

As I got older and the hormones of puberty started to surge, it was easy for me to confuse sexual attraction to women with a desire to emulate them or even be one of them. As I grew into my twenties, it became clearer to me that my desire to emulate women was something distinctly different from my desire to have sex with them. At this period in my life, I did not have the understanding or vocabulary to make much sense of this distinction.

It wasn't until I was in my early thirties when I first got online, did I discover that there were others like me. When I finally got in contact with them, they helped me sort things out. Only with this help did I finally come to better understand what was happening inside of my head. With this better understanding and a bit more maturity, I found the courage to be honest with myself.

It was only after I admitted to myself that I really was a crossdresser and realized that being a crossdresser was OK did I start crossdressing seriously.

Why do I crossdress?
This is simple answer - I have to. Call it a compulsion, but I feel a need to emulate women - their look, their mannerisms, their subtle differences in communication, and their role in society. I enjoy crossdressing and when I don't do it, I miss it. I miss it a lot. If I go for long periods of time without dressing, I feel a certain stress that is something akin to being overworked.

Another reason why I crossdress is that it is fun! I honestly enjoy the primping and the makeup and the shoes and the dresses and the styles... Many women enjoy such things, so it is not unreasonable that I like these things too. A lot of transfolk invent reasons to dress up, such as formal banquets, cotillions, and themed parties, where we can wear our finest beaded gowns, ballroom dresses, and our most elegant formalwear.

No one, including me, is quite sure why some people crossdress while others do not, but several theories exist. These theories suggest something to do with genetic (chromosomal) abnormalities while other suggest differences in child rearing. Recent studies have shown that such physiological factors as genetics and hormonal fluctuations during pregnancy can significantly affect how our brains are "wired" which in turn influences our sense of gender but no one is really sure about all of this. This is a complex issue and I suspect that the reasons why some people crossdress are also complex and do vary somewhat from person-to-person.

Why don't I just stop crossdressing?
This is another simple answer - I can't. Virtually all transgender folk can't just "stop doing it." Some try and may be relatively successful for a period of time, but very few actually give it up completely or forever. When I first became engaged to my wife, I made a decision to "purge" and put any and all thoughts of crossdressing out of my head. It didn't work. Eventually, I had recognize that this is just too important a part of me to ignore or surpress.

I have never chosen to feel this way but I do and I know that I always will. At an earlier point in my life, if you gave me a pill and told me that if I swallowed it I would no longer feel this way, I probably would have gulped it down. But over the years, I have come to find great joy in expressing myself as a women, so if given the chance today, I wouldn't take that pill. I like who I am and a significant part of me is defined by my desire to be feminine.

Since I can't change the way that I feel, I have decided to embrace this part of my personality and make the most of it.

Am I gay?
No, I am not gay - at least not in the classic sense of the word. When I am presenting myself as a woman and you accept me as a female, then you can consider me a lesbian. This is because as a female I am still sexually attracted to other females.

Perhaps it is more accurate to label me bisexual since I have been attracted to a number of very feminine transgender people - regardless of their genitalia. By and large, I am not really attracted to men, although I have had a fantasy or two about being a woman who is having sex with a man. Does this all make me "bisexual?" Perhaps, probably no more so than any other person who has had a kinky thought or two.

Just because I am not typically attracted to me does not mean that I do not appreciate their attention. When I am dressed, I like to be considered attractive and desirable, so I enjoy harmless flirting and the occassional compliment.

Does being a crossdresser mean that I have some sort of mental illness?
This is a matter of opinion. Some people would diagnose me as having "gender dysphoria," which is mental illness included in the “Diagnostic and Statistical Manual of Mental Disorders" published by the American Psychiatric Association. Other medical establishments do not agree that crossdressing or gender differences imply any sort of mental illness. Personally, I have come to the conclusion that there really isn't anything wrong with me - I just happen to be a bit different that a lot of other people. Although I may not be responsible for feeling this way, I am responsible for my own actions. As long as I don't do anything wrong, then why should I feel that there is anything wrong with me?

The transgender phenomenon has been studied long enough to show that, apart from being crossdressers, we are no more or less inclined to suffer from any mental maladies than the population as a whole.

Is there an erotic component to my crossdressing?
The short answer is "yes," but it is not as significant as one might think.

As a teen with my hormones raging, it was easy to confuse sexual attraction to women with my feelings that led me to crossdressing. I don't believe that I have ever really untangled the two issues 100%. My desire to emulate women is mostly focused on emulating attractive women. Although I may respect and admire Madeline Albright and Margaret Thatcher, I would rather emulate Nicole Kidman or Catherine Zeta-Jones. Just by virtue of the fact that I desire to emulate women with whom I am more sexually attracted to implies some sort of erotic connection may exist.

Catherine Zeta-Jones Nicole Kidman  vs.  Margaret Thatcher Madeline Albright

With some people, crossdressing is a big fetish. The primary purpose for them to crossdress is for masterbating. Although I can't cite any studies to support this, it is my belief that these fetishistic people aren't likely to be the same people who go out in public dressed and attempt to pass as a female. I would be lying if I claim that I have not masterbated, but my crossdressing has relatively little to do with that. Since I remain faithful to my wife and she is not a lesbian, I only have sex as a man, so I don't have sex in the role of a woman.

What does my wife think of all of this?
As a general rule, I keep my comments about my wife and family to a minimum, but I will mention a few things.

No little girl thinks to herself "When I grow up, I want to marry a crossdresser!" My wife is not delighted with the idea of me being a crossdresser but she accepts it and finds ways to make the most of it. She once told me that she would not reject any of our children if they came out as being transgender, so she couldn't treat me any different. For as accepting as she is, I must also admit that it has been the source of some arguments that we have had over the years, but no more than other issues we have had in our many years of marriage.

At times, my wife does participate with me when I crossdress. But since our children are still young and we are not overtly advertising that I am transgender, so she often will stay home with the kids so that I can attend various GLBT community functions. Sometimes, if we can arrange for a sitter, she will join me - where she is always warmly welcomed. If fact, she has become close friends with quite a few of my transgender pals. My wife and I share clothes, go shopping together, offer each other advice and generally behave like the good friends that we are.

Her biggest concern is that one day I will end up a post-operative transsexual and she will have lost me as a husband. I don't see that as likely, but it is a reasonable concern for any spouse to have.

Do I ever fear for my safety when crossdressing?
Yes, I have. There have been times when I felt fearful that I would be physically harmed because of my dressing. Fortunately, I have never actually been harmed.

The fear I experience is not unlike what women in general might fear in certain circumstances. For example, it is very late at night and I am leaving a club alone and my car is parked three blocks down the street. I see a group of young guys on my side of the street walking in my direction. I cross to the other side of the street so I don't have to walk through them and risk putting myself in harms way… This scenario is not any different than many women in general. I did have my handbag stolen once, but I suspect that had less to do with me being a crossdresser and more to do with the thief feeling that someone walking out of a bar late at night would be an easy mark. Although I am careful about where I go and what I do when crossdressing, I am thankful not to have ever suffered any real physical harm. This is not so for too many other transgender folk. The website Remembering Our Dead is a sad reminder of that many transpeople who were victims.

Have I ever suffered from any prejudice?
Apart from the rare jerk who makes a rude or insensitive remark in public, I have been fortunate enough to have not suffered overtly any prejudices because of my crossdressing. I say "overtly" because few people actually come out and admit that they have treated you a certain way because you are a crossdresser or they think you are one. I am certain that I may not have received the best service from some restaurants, but nothing that I can prove. Also, I am certain that over the years I did not get certain jobs because I did not "look" a certain way, but again nothing that I can prove.

Although I have been fairly free of prejudices, many others have not been. Each month, there are reports of someone losing their job because they are transgender, someone being severely beaten, or even someone being killed.

Personally, I have a hard time understanding why transgender folk are given such a hard time by some people. If it is acceptable to have a gay school teacher then why not a crossdressing school teacher? Nobody cares what a school teacher likes sexually as long as they don't have sex in the classroom or with students… When a police officer pulls over a crossdresser for a simple traffic violation, why should it be mentioned in the police report what the person is wearing and thus outing the crossdresser? Does beating up a crossdresser in a mall parking lot "cure" the crossdresser of being transgender?

The only conclusion that I can come up with for such abuses against the transgender community is fear. Fear that my gender presentation somehow threatens them. Fear that I may make them less of a person somehow… Fear because of misunderstanding - and being transgender is certain not understood by many.

What does the future hold for me?
I am not sure what the future holds and that is OK.

In my younger years, I found a great deal of comfort to plan things out and to know precisely what goals I was working to achieve. As I grew older and became more confident in myself, I placed less emphasis on the goals and more on the journey. This approach applies to my transgenderism as well.

Not surprisingly, what satisfies me as a crossdresser has evolved over the years. When I was child, I was content with play acting although I was secretly envious of my sisters and cousins. As an adult first coming out as transgender, I was satisfied just with finding people who accepted me and being able to attend the occasional support meeting in a pretty dress. Ten years ago, getting my ears pierced seemed like a big step for me and I couldn't imagine that I would ever have had electrolysis to remove my facial hair. Yet, five years ago, getting rid of my beard was important enough to me to do just that. Last year, I met with a surgeon to inquire about improving my looks. In recent months, I had hair transplants to fill in a receding hairline…

Today, it is important to me that I look convincing when I present as a woman. It is also important to me that I can be "me" in whatever gender I am presenting without feeling that it is all smoke and mirrors - it is a sort of honesty with myself.

It may sound like I am steadily moving towards physically changing my body to be more feminine which a logical conclusion of me having genital surgery. Believe it or not, I don't think that is likely. Yes, the physical changes I have made do make me more feminine, but these are also the same sorts of things people do to make themselves look younger. Aging is a process that makes people look more and more masculine. So it should be of little surprise to hear that the medical procedures used to make a person look more feminine are only subtly different from the procedures used to make someone look younger regardless of their gender. I want to look better - be that looking younger or looking more feminine or both. Perhaps it all stems from vanity, perhaps it is my increasing comfort with myself and my being a transperson...

The changes to my physical looks are not radical, albeit noticeable. Many of my friends are musicians so growing my hair long did not seem unusual at all to many people. In fact, I am regularly asked if I am in a rock band. Getting my ears pierced was also no big deal. My eyebrows are much thinner than when I was young, but not the elegantly arched brows that you would find on many women. Taken together, all of these changes make me look me more androgynous than feminine in my every day life but have a huge effect on how well I present as a woman.

I should make it clear that these physical changes are a bit atypical for crossdressers. The vast majority of crossdressers are satisfied with only wearing women's clothes and assuming their mannerisms. Sure, there are some crossdressers would come to realize that they are really transsexuals but that seems to me to be the exception rather than the rule. Most crossdressers don't do anything much more drastic than getting their ears pierced.

Regardless of the physical changes, at this point in my life, I don't envision myself having genital surgery or even living fulltime as a woman. Admittedly, there are aspects of these visions that I do find attractive. I enjoy it when I am presenting as a woman so there is a certain desire to be able to enjoy myself all the time. But life is never so simple. It is a balancing act. There are realities that each of us needs to face. I have a wife who would object to genital surgery or developing breasts. I have to think of the impact on my kids, my career, my personal relationships with friends and family… Also, there are things about being a male that I like and appreciate and would probably miss if I gave them up. No, living fulltime as a woman remains just a wonderful fantasy of mine.

I realize that there's no absolute way to predict the future. I may find myself feeling different in ten years. That's OK. I will feel the way I will feel and I doubt that I can "make" myself feel a certain way. I don't feel compelled to have my whole life planned out. I don't need to know exactly what I will be doing in ten years. All I feel compelled to do is have a satisfying life as I am living it.

Living a satisfying life is really all that any of us can hope for.

On a final note, I would like to acknowledge and thank my friend and colleague Miqqi Alicia Gilbert who wrote "Cross Dressing 101" which was published in Tapestry Magazine. In her article, Dr. Gilbert answered a series of similar questions about herself which inspired me to write this article about my personal situation.