Oh, hi. Welcome back. This is the second part of this little series about why crossdressing is fun and enjoyable. Essentially many, many crossdressers wonder why they like to wear what they wear. If you haven’t read the first part, you may want to take a peek at it.
But to recap, in these two articles I am going to use the words “crossdresser” and “crossdressing”as broad, generalized blanket terms which 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. There are a lot of qualifiers in that last sentence.
In the previous article, I mentioned four common reasons why non-crossdresser think that people assigned male at birth crossdress. These reasons often cause a crossdresser to assume that they wear what they wear because of one or more of these reasons. Perhaps, but maybe not. In part two, I want to talk about other reasons that someone who doesn’t “have” to wear a bra, high heels, or stockings may choose to, or at least daydream about.
Before I go further, I want to emphasize that I am not an expert and no one, especially me, should tell you how you should identify or why you are who you are. Perhaps there is something here that you identify with or relate to. Perhaps I am completely off the mark. Your experiences and your perspectives are your own, and you don’t have to fit into any category or find a term that you identify with.
Okay, let’s begin.
Why crossdress? Comfort. The clothes are softer. I choose to wear leggings when I am home because doing household chores or just relaxing is so much more enjoyable than wearing jeans. Even femme jeans are softer than boy jeans. The hill I will die on is that once a man stops being such a coward and actually tries on a pair of leggings or falls asleep in a nightgown, they will never go back to boy clothes full time. Why anyone with a penis and testicles would wear loose, ill-fitting, boxer shorts is beyond me. Panties are not only super cute but the fabric is more comfortable and they keep… ah, things in place. Provided that the panties are the right size and style, of course.
Why crossdress? The FEEL. A satin nightgown feels so much better on skin than itchy sweatpants or pajama pants.
Why crossdress? Girl clothes are CUTE and so much more interesting than boy clothes. I get bored easily and the idea of only wearing SHIRT and PANTS is just as dull as it gets. If I am going out as a boy, SHIRT and PANTS. If Hannah is going out… oh girl. Skirt and cute top? Bodycon dress? Black tights? Beige stockings? Red stilettos? Black, knee-high boots? Shiny Mary Janes?
Of course, there is also what clothes can bring out of us. When I first started dressing around my wife, I felt… well, amazed and happy, but I also felt exposed and vulnerable. When I say “exposed” it wasn’t because I was wearing lingerie (although that can make anyone feel a little exposed), No, I felt exposed because for my entire life up until then wearing lingerie was my most treasured, closely guarded secret. I had protected this side of me with my life. I was completely paranoid about someone discovering my bras in my dresser or seeing my pink panties peeking at them from under my jeans.
Of course, this paranoia kept me from being caught. I wasn’t ashamed at who I was (or still am) but given how misunderstood all of this was (and still is), the idea of having to explain (and to be potentially ostracized from people in my life) who I was and why I am who I am was not of interest to me. Afterall, I didn’t understand why I am who I am, how on earth could I explain something I didn’t myself understand?
When one is feeling exposed, then feeling vulnerable is a pretty natural feeling. I mean, my boy clothes covered up my lingerie. My boy clothes were my armor and again, protected my crossdressing from the world. Without my armour, I was vulnerable to the world…. or in this situation, my wife (who is my world, lol).
This vulnerability led to honesty. I had felt more open with her than I had ever felt before. I talked about my feelings and thoughts (and not just about gender) in a way that I had never done before. I felt safe. I was safe. As time passed, I became more and more accustomed to talking about my feelings and thoughts, regardless of what I was wearing. Those first few weeks of dressing around her were the push I needed to be more open.
Why crossdress? Girl clothes are CUTE and so much more interesting than boy clothes.
Of course, it would be inadequate and not entirely accurate to say that crossdressing made me a better person. It wasn’t lingerie per se. I become a better person and a better partner because I become more comfortable with opening up. That openness benefited both of us. I just came around in a pretty unorthodox way.
Some of us crossdress because we don’t look at gender as a binary (and psst! It’s not). The whole idea that some things are for boys and some things are for girls is ridiculous. We may not look at skirts as girl clothes. They are just clothes and why shouldn’t people wear what they want? I suppose if clothes are for anyone and everyone, no one is *really* crossdressing. If a skirt is just a skirt, and not a “girl’s skirt”, then it is, be definition, a skirt. No gender associated with it.
Finally, this might be the most obvious and likely the most anti-climatic and unsatisfying reason why we crossdress. Because it makes us happy. Why does it make us happy? Oh, now we’re back to the beginning. It’s pointless to wonder why certain things make us happy. They just do. As someone who started wearing girl clothes over forty-five years ago, I still haven’t decided why this part of my identity makes me happy. I love picking out my panties every morning. I love choosing which nightgown I will wake up in and then drink my coffee in. I love trying on dresses in a vain effort to find the perfect outfit for a Saturday. I love deciding between two similar (but different enough) pairs of black patent stilettos for a night out.
Still not helpful? Okay, here’s my last try.
In my opinion there are really two reasons why someone loves crossdressing:
1) Gender identity.
Wearing clothes that are typically associated with a gender that is different from the one they were assigned at birth feels… well, right. People who identify as transgender, non-binary, or in similar ways often feel that there is just something more to their gender than they were raised into thinking. Calling myself male growing up didn’t feel quite right. I didn’t feel it was wrong, but it felt kind of pointless. All the men in my life and all the men I saw in movies and on television were Very Strong and Very Outdoorsy and Very Tough and all that. Men liked SPORTS and BEER and THAT WAS IT. If that was what a man was supposed to be, then there’s no way I could be one. Even at a young age, I saw the futility and pointlessness of gender norms. Why did I HAVE to play baseball after school? Why couldn’t I like gentle things? As I grew older I saw how everything was genderized. Everything and anything was for a boy OR a girl. I stopped caring about what I was SUPPOSED to like and what I was SUPPOSED to wear. As my thinking continued to grow beyond these invented gender norms, I realized I didn’t HAVE to identify as male. I didn’t have to identify as anything if I didn’t want to. Growing up I loved wearing girl clothes and always will. Realizing that I loved dresses, even when I was very young, was the start of me realizing that gender norms are a societal invention. There was no reason I couldn’t wear what I wanted to. “Male” was never right for me. Crossdressing was the beginning of learning who I am. I began to identify as transgender, or in a more specific way, bi-gender. Please note that a trangedner person does not need to transition or live full time to identify as such. You can be transgender without estrogen and without legally changing your name or other steps one can take when it comes to their gender.
2) Crossdressing is fun and fun things don’t need to be examined
So, in summary, you love crossdressing because it’s the start of a deeper, more introspective, and personal evolution of your gender identity OR it doesn’t.
Rereading this little series has struck me at how… well, not helpful this has been. But in a way that’s my point. Although it’s possible that crossdressing is the tip of the iceberg when it comes to gender identity, it doesn’t always mean that there is some deep meaning or reason someone enjoys “girl clothes”. I think we put too much effort into trying to figure all of this out when we first slip into a pair of panties. Generally, as time passes, you’ll likely realize, in an organic way, what, if anything, all of this means. You don’t have to know WHY you like something. Just fasten your garter belt and enjoy the ride.
Love, Hannah
