All right, let’s give this a try.
Before I go any further, I am going to be completely upfront and honest and transparent with you. I have NO idea if I am correct with any of the suppositions I am going to ramble on and on about. I have no idea if anything I say here is correct, applicable, and/or relatable to anyone reading this.
So, take everything here with a grain of salt. I am not an authority on anything or anyone other than myself, and I do not presume to speak for the transgender/non-binary community. I fully expect people to disagree with me on all or part of this article or not find this helpful at all. But I am still going to try to answer a question that I don’t think has or needs an answer.
Why do we like crossdressing?
For the purpose of this article, “crossdressing” and “crossdressers” and all associated terms are meant to be generalized words that essentially covers anyone that was assigned male at birth who wears clothing that are typically associated with clothes that people who were assigned female at birth wear.
Why don’t I think we need an answer? Because it doesn’t really matter WHY we like crossdressing. For many of us, wearing clothes and/or presenting as a different gender than the one we were assigned at birth just… feels right. And that’s a wonderful feeling. Clothes, for some of us, can be a physical representation of who we are in our heart, mind, and soul.
Essentially, clothes, regardless of what they are, can and likely reflect our identity. And this is true for any clothing that someone can wear. Someone wearing a certain t-shirt can tell the world who their favorite band is or what sports team they cheer for.
I think that if you are honest with who we are, and embrace who you are, and wear what you want, you probably LIKE what you wear. I mean, yes, after a long day I never want to wear stilettos ever again or it feels wonderful to finally take off my corset, but I still LOVE my high heels and I still love my lingerie. What I wear might be a little uncomfortable after a few hours, but I wear what I wear because it all helps me present in a way that reflects who I am and for that very reason I will always love my corsets and tucking gaffs and everything else.
Why someone crossdresses is something that only they themselves can answer. I get a lot of emails from those who are just starting to dip their pink painted toenails into this wonderful world. These emails are a medley of joy and fear and confusion and questions. It’s funny, but the question that seems to vex the majority of these emailers is them trying to understand WHY they like crossdressing. Not what all of THIS means (though there is that to a lesser extent) but it’s almost as if they want to know WHY they like to wear what they want before they can process anything else.
Why don’t I think we need an answer? Because it doesn’t really matter WHY we like crossdressing.
My response tends to be that there doesn’t NEED to be an answer. People generally don’t over analyze WHY they like the other things in their lives. Why do people like watching golf? Why do people like movies? Why do people like sushi? I mean, sure, they may like watching a professional golfer because they enjoy the “sport” or they like watching actors or they like the taste of sushi, but… WHY? If I were to ask my brother-in-law why he stares at the television for hours every Saturday watching bowling he would probably shrug and say that he just likes bowling. He probably hasn’t ever given it a second thought WHY he likes bowling. He doesn’t care WHY he likes it, he just does. And that’s okay! He would probably think I was insane (and annoying) if I kept pressing for a psychological “reason” he liked watching professionals bowlers
Why do you like crossdressing? You just do. Move on.
Not good enough of a reason? Okay, fair.
Let’s start with the four reasons that is commonly assumed for crossdressing:
1) Crossdressers are gay.
Of course, gender identity and how one presents has nothing inherently to do with sexuality. Wearing a nightgown to bed has nothing to do with WHO I want to go to bed WITH.
2) Crossdressers are fetiishist
A man wearing clothes that he is “not supposed” is very arousing to some. And that’s okay, no judgement. After all, this is true for some of us.
3) Crossdressers are men who were born in the wrong body
A man wanting to wear “girl clothes” is someone who is going to, in the process of, or has transitioned.
4) Men wear girl clothes because they have unresolved trauma, likely relating to their parents, that they have not addressed
This is usually perceived as a boy not getting enough love or attention (or too much love or attention) from a parent or an imbalance of traditional, binary gender representation growing up. Out of all of these “reasons” I feel this is the most far-fetched but that doesn’t mean it’s not applicable to some.
These are assumptions, but that doesn’t mean they are always wrong. For some of us, our journey begins by being drawn to wearing a dress or anything else that is “for girls”. As one’s journey progresses, it’s possible that they may realize something significant about themselves. Perhaps crossdressing was the tip of the iceberg and they now identify as transgender and may have even done procedures or treatments to become the person physically that they are emotionally and mentally. Not every transgender person transitions after all, you know.
People don’t generally over analyze WHY they like the other things in their lives. Why do people like watching golf? Why do people like movies? Why do people like sushi?
SInce these are the four most common “reasons” a person can enjoy crossdressing, it is not a surprise that those who crossdress wonder if they themselves fit into one of these four reasons. This is when panic might set in. A dude lived a couple decades or more crushing on girls, but now that they have accepted themselves as crossdressers, all of a sudden they are thrown into a self-induced tailspin about sexuality. Maybe they DO like other dudes, after all. Of course, there’s nothing wrong with being gay, but oftentimes that panic sets in because a) their life is about to turn upside down as they have made the realization that they have a different sexuality from what they thought they were and b) the fear and worrying about how others will react.
I’ll just throw this out there but crossdressing doesn’t make you gay. Also, you are not crossdressing because you are gay but haven’t realized it. It’s very possible your heterosexuality isn’t as locked in as you think, but wearing panties doesn’t really move the sexuality needle.
Panic also sets in when said crossdresser wonders what all of this means. Does the happiness one feels when they wear lingerie is an indicator that their gender identity is a little more fluid and prone to change than they once believed? Mmmmmmmmaybe, but slow down cowgirl.
I believe that (almost) everyone who identifies as transgender has, at one time, even for a moment, likely identified as a crossdresser. Afterall, this journey and introspection can begin young. We look through our mom’s or sister’s closets and try on anything and everything that might fit. All of the pieces may not have fallen into place yet, but we know this much: Although everyone says we are a boy, WE LOVE GIRL CLOTHES.
Sooooo it IS possible that at one point in a crossdresser’s life they MAY understand that there’s more to wearing girl clothes than they realize. Nothing definitive, but perhaps.
To put it in a different, but overly generalized way: Not every crossdresser is transgender, but almost all transgender people likely identified as a crossdresser at one point.
Again, we need to slow down. Daydreaming about wearing a lace teddy doesn’t mean you should be on estrogen.
As for fetishists who just enjoy crossdressing as a kink, this may be rooted in playing around with gender roles or because a boy wearing girl clothes is a sexy taboo. If crossdressing arouses you (and you know what I mean) but does not factor into your life besides during sexy time, it’s very possible that crossdressing is a kink, and like most kinks, it’s probably not explainable. It’s just how we’re wired. I am afraid I don’t have much to say about crossdressing as a kink but my go-to perspective on anything that is kinky or a fetish, as long as your interests are ethical, harmless, and with someone who is completely consensual, I feel that’s all that really matters.
Well, one more thought. Crossdressing as a kink can be, well, a gateway to beginning a journey when it comes to identity. When you are fooling around with your partner, you may be more spontaneous and adventurous than you are outside of the bedroom. Crossdressers often test the waters, if you will, in the bedroom. Maybe we’ll slip on her panties (please don’t do this) to see how she’ll react. If it goes bad, you can say you were being silly and were caught up in the moment. If your partner likes it, well….. that might be a stepping stone to wearing panties outside of bed.
I would be remiss if I didn’t mention that I believe the conversations about kinks, desires, fantasies, should be had before sexy time begins. Springing a new… thing onto your partner, especially when it’s a risky fantasy, can kill the mood and more importantly it’s unfair to put your partner on the spot like that.
Goodness I am rambling but I think this is going okayish? But let’s circle back in a couple weeks to talk about other possible reasons that we like crossdressing.
Love, Hannah
