There are times where I wonder what people think about men crossdressing. I was watching the television series After Life and an exchange between two of the characters piqued my interest. One said something to the effect of “you never see blokes dressing like women for fun anymore” to which the other replied “good because you shouldn’t.”

I agree and disagree. In the past, I’ve seen guys do it as a spectacle. I remember in high school we would have assemblies where the guys would dress like women and then try to complete a ridiculous obstacle course. I never found it entertaining in the least and it’s probably part of the reason why I ditched school during those events. That stuff should go away. There’s nothing funny about a man dressing in women’s clothes. 

However, there are men out there for which crossdressing is derived from an emotional standpoint other than humor. This form of dress should stay around and it’s that which I will speak to. 

Can I get more options?

As you can imagine, I crossdress. I don’t crossdress in public (well, once but that’s a story for another time) but I don’t hide the fact that it is part of who I am. I dress around home for me and my partner. I’m sure there are a number of motivations for a guy to crossdress and I’m also sure there are a wide variety of people who do it, so I should caution you that this is my story alone.

For me, and I’m going to bet most other men (whether they realize it or not), traditional American masculinity, rigidly adhered to, is confining in the least and soul crushing at most. Men are supposed to act and look a certain way and I find both of those things incredibly limiting, toxic, and just generally non representative of what it means to be a fully actualized human being. 

If you look at men who are insecure about their level of masculinity they often overcompensate. It’s no coincidence that men become the majority of our mass shooters, militia nut jobs, gay bashers, racists, misogynists, and incels. While these are the most pernicious forms of our individuality denied, it should be noted that gender policing among guys is still shockingly common. Calling someone gay (as if gay is non-masculine) when they do something that isnt viewed as manly is stlll appallingly common. These things signal that manly is still a category that is heavily scrutinized and controlled. 

Given this climate, I figured I could go one of two ways. I could own a gun, drive a four-wheel drive and double down on my insecurity by hating anything feminine and portraying myself as over the top masculine or I could create my own version of who I wanted to be. So now, I own a gun, drive a four-wheel drive (because some things just don’t change), and flit around in so-called girly things.

So why do I crossdress? 

I have almost always wanted to feel desirable in the clothes I wear but what I find attractive are the clothing styles made for women. There isn’t much for guys to wear in order to feel sexy.

As men our physical sex appeal is mainly derived from our bodies which are supposed to be somewhat bulky. I am tall, I am also thin. In fact, I am probably thinner than most women. Because of that, I’m never going to carry a good deal of rippled muscle and any other bulk would have to be in the form of a beer belly which while obtainable, is not really my style. I have gone 40 years without having a body that others regard as truly manly. 

This bothered me as a kid but now I love being this thin. I’ve never found muscles or a strictly “manly” physique attractive. I’ve always been drawn to the slighter, softer side of anatomy in all types of folks and so in myself as well.

So donning women’s clothes allows me to feel sexy by virtue of what I’m wearing and there is something I find alluring, even empowering, in that. As an added bonus, my thin build pairs well with women’s fashion. At least as well as it can for a guy. Donning a cute skirt to accentuate hips I don’t have, and a crop top and belly button ring to show off the small waist I do have, is an exciting and fulfilling experience. I finally get compliments about my body that I have never received while dressed as a man; and that’s not hyperbole either. So that’s one reason but, it’s also more than that. 

Just one body?

The next reason may throw you for a loop, or you may understand. I’m perfectly happy in a male body and I readily identify as a male. Still, if I could also morph my body and have a female form, male form, or some other form depending on my mood then I would love that. This isn’t a fetish, it’s an actual desire to be able to live this way. 

When I see a woman walking down the street in a cute outfit I will do a double take but it’s not for the reasons most guys do. Rather, I’m jealous that I can’t look that cute in the same outfit and that I wouldn’t be accepted if I did. Both concerns stem directly from the fact that my balls tend to hang out of skimpy shorts. Physiology problems, am I right? 

Joking aside, I’m also aware that dressing as a man in women’s clothes could also put me in danger from closed minded bigots (those guys I mentioned earlier). Having a female form to change into would eliminate those worries. Since I can’t do that, cross dressing is a way for me to overlay a feminine shade on a masculine base color. 

It’s here I feel I should take a step back and clarify a few things. I worry that saying these things sounds privileged in some way because I’m a guy. The claim being that I want to experience different forms of being but not permanently and so without responsibility.

I, for now, claim the exact opposite. Different bodies come with different socio-political realities. If my body morphing powers came to fruition I would simultaneously be bearing the brunt and benefit of each body type I filled. I couldn’t take any form without it’s reality bearing down on me. I have no misgivings that if I were some version of female I would be the subject of men’s toxic behavior. If I had a combination physiology then I would have to fear people who can’t wrap their mind around anything but a gender binary (still mostly men by the way). My claim isn’t that there is no danger, but that wearing some of the things I want as a woman puts me under the radar bigots. Changing forms then would simply be changing realities and not escaping altogether. However, I want to explore this idea more fully in the future.

What do I call myself?

I know I am not transgendered. That’s how I initially started this paragraph then I read some material from trans folk that includes what I do under the trans umbrella. I have no problem with being called trans should people choose. I love my big, beautiful, queer family and that absolutely includes my trans brothers and sisters. I support them wholeheartedly. We have some similarities I’m sure and some differences. We can celebrate them all as facets of our uniqueness. 

Maybe there is a term for how I feel. I think of what I do as gender blending for the most part. I’ve seen the term transfeminine (male at birth, but identifying closely with femininity, yet not desirous of being a woman) and I think that fits closely but not exactly. I am desirous of being a woman, but also a man, and also configurations in between. To be perfectly honest, the name for what I do and how I feel doesn’t matter much to me. I’m just trying to embody what feels like the truest expression of who I am within the bounds of reality. 

I have always thought it would be an easy thing to explain; this way I feel. Now that I try to put it in writing for the first time the words seem too definite. Each sentence that I try to use as a tack to hold down what I am seems to have my feelings squeezing out and around every word. Nothing seems as accurate at the conclusion of my sentences as it did when I began them. Feelings are easy to experience but more difficult to write down. Still, this is a beginning and that’s an important step. 

My future

I don’t know what my future holds on this front. My everyday look is slowly evolving. I’ve picked up bracelet making and I’m trying to blend masculine and feminine styles, I paint my nails when I have the time, and I’ve been tossing around the idea of a choker necklace and eye liner. None of this is overly important other than to say, my goal is to blur gender expressions just enough to soften my masculine edge. I think that’s where my happy medium will be but the whole endeavor is an experiment and I’m enjoying the process. Life is more colorful, fun, and lacy now. 

As far as my advocacy goes, I plan to discuss this issue more often from a variety of standpoints. I also want to talk about useful things for folks that crossdress such as finding the right clothes (once I learn how), shopping tips etc. I want to make this issue more visible because there are more people like me out there and I want us to be seen and heard. 

Ultimately, I want the kind of society in which folks with all types of bodies and styles of dress can be accepted and don’t have to face the repercussions of closed minds. Perhaps then I would be satisfied with just my body, perhaps not. 

I imagine I will expire from old age before I will see the type of society in which I would be comfortable. The best I can do right now is to help expand what being male can be so that someday, someone else can live my dream. I want to help enlarge our circle of compassion so we may be the better for it. Crossdressing helps me wrap my mind around that from a practical and abstract standpoint. It helps me to feel things that I am not traditionally allowed to feel and to be closer to who I want to be. It puts me in touch with something rather intangible that I want to help others find.