Why Do I Enjoy Crossdressing?

Before I address this question directly, I feel it is important to begin with a definition of crossdressing.  Wikipedia (which is sufficient for my purposes) defines crossdressing as  "the act of wearing clothing and other accouterments commonly associated with the opposite sex within a particular society."    I see this as relevant because crossdressing is less about the clothing we wear than about how society regards the clothes we are wearing.  While this speaks to a lot of issues commonly discussed regarding crossdressing, I stress societal definition of crossdressing here to emphasis that for whatever reason I may choose to step out of my home in gender-inappropriate attire as defined by our society, it is society and not myself labeling me a crossdresser.

Crossdressing is Not Gender Identity or Sexual Oreintation

Why have I begun with this digression.  Crossdressing is too often tied to unrelated issues of gender identity and sexual orientation.  Transgender women insist they dress as they do because of their gender identity even though everyone admits women are pretty much free to wear whatever they like and many disdain wearing bras and dresses and anything feminine. Society tends to see any man dressed as a woman as someone who is gay, one who is out displaying 'his' feather to attract a mate.  Even though many studies suggest that most crossdresser see themselves as heterosexual and have no interest in men.

I now come to that part of this post in which I draw my over-riding conclusion.   We all have our reasons for crossdressing and while it may or may not be related to our gender identity and our sexual orientation, crossdressing is still something we choose to do.  Now some may suggest I have it all wrong, that if I only knew what it felt like for them, I would know how wrong I was.  And I may well be.  One thing is for certain, we cannot both be right so one of us must be wrong and that could be me.

So why do I crossdress?  Why do I enjoy crossdressing? 

 I enjoy it for the sex.  If I did not crossdress, I would not attract men and I prefer male partners as Veronica over female partners as Glen.  Did I just contradict what I said about gender identity and sexual orientation?  It is important to re-consider my premise.  How I choose to dress is always a matter of my choice.  I do not care how intensely certain you are that you are a girl that does not compel you to slip into a bra.  It is still your choice to dress as a woman.  Secondly, why I choose to crossdress, my desired result, is not how I am judged by society. Whether I dress to attract men or because it feels good or because of a dare, I am still seen as a crossdresser to those who see us out and about.

I often remark in my online communications that I am not a 'crossdresser,' that I am one who crossdresses.  it is a distinction between a label assigned to me that defines me and what I do.  However,  I am becoming increasingly unhappy with the whole concept of crossdressing.  It feels archaic to me.  It is telling me as a member of a free society how I may dress and what is inappropriate, how I may choose to express myself.   It could be said that I hate crossdressing and yet love to dress up in dresses and lingerie.

So lets say that this was a free society, that I was free to step out of my home wearing whatever I choose without be judged, without being seen as a 'crossdresser' or 'a man in a dress.'  In this prefect world,  I would be no different than the 95-98% of Americans who do not crossdress.  My gender identity and my sexual orientation would not be questioned.  In this prefect world it could be said that I am simply someone who has chosen to step out looking her best and not uncommonly one who is open to attracting the sexual interest of others.

Am I Gay or Straight?

In this prefect world,  as I am one who dresses to attract men am I gay?  I think not.  I am not attracted to gay men.  Quite frankly I often find it repulsive when I see two men kissing (even though it is wrong to be that close-minded and even though I am much more accepting of it than many or even most would be).  Gay men are not attracted to me and straight men are often attracted to me.  While occasionally a man I am with might share that he is bisexual, most of them would label  themselves 'straight.'

So am I a woman; am I transgender?   Socially (and sexually) I will always prefer interacting with others as a woman over doing so as a man.  But in the privacy of my home, being 'her' is usually just too much trouble.  I am content to wear guy clothes for comfort  -- not unlike millions of women who upon arriving home will strip off their dress and change into a pair of jeans and never put on makeup when spending the day at home.

Despite everything or anything I may have said in this post, there may be a million and one butterfly effects for why I prefer dressing as a woman to dressing as a man.  But it all comes down to this.   When I am getting ready to go out, if I am looking to have a good time out, if I am looking to meet someone with the ultimate goal of having sex, I dress as a woman.  If I am a woman,  I must be a woman who prefers anal sex with men.  If I am a man, I am a man who prefers those who appreciate my beauty as a woman.  If I am transgender, I am reasonably content to be a man when alone while preferring to be a woman when with others.  If I am a gay male, I am one who disdains the flamboyance gay men so often display and if I am straight woman why do I find almost all of my hookups at gay bars.

So why do I enjoy dressing as a woman?

Like everyone else, when I step out  I like to look my best.  My best demands I be wearing a dress, a wig, breast forms, makeup, high heels, perfume and anything and everything else that might create the prefect package.  More often I am on the prowl and I am looking for straight men  -- not gay, not bisexual, straight. I am looking for men who will find me attractive, men who will feed my ego with compliments and lingering looks and soft embraces.   I am looking for men who want to be with a woman and a man who knows I want to be with a man.  I am not looking for a man who wants to be with another man, but a man who sees me for the woman I am, the woman I will be with him.

While it could be said that I dress as I do to attract and lure and seduce men into my web, I am also dressing for men who have sought me out, seeking something more from me  that other women cannot provide, do not provide.  To these men, in some ways, I am more 'woman' to them than the wives and girlfriends that are alone at home, unaware that their man has chosen to seek out a woman who will fulfill his sexual desires as only a real woman can.  I dress not because I have any illusion  that I am his female, but as one totally willing to be his woman.  I dress (and I enjoy crossdressing) because given a choice between the role and live of a woman and the role and live of a man, let me be the woman every time.  And never more so than when he is using me and abusing me according to his basest desires as a man, leaving me undeniably a bit more of a woman than I was when the night began.