My First Time

For decades now I have been crossdressing in private. In the last couple of years my desire to take a little bit of this feminine flair out into the world has been increasing. I was going through my clothes the other night and I noticed how much I liked wearing women’s jeans. Moreover, I realized that certain designs were not that far off from the men’s pants I was already wearing. Suddenly, wearing the perfect pair of women’s jeans seemed like a nice blend of masculine and feminine.

There was a slight catch. Because I acquired most of my women’s clothes surreptitiously from strangers (craigslist, ebay, etc), I didn’t get to try any of it on ahead of time. So while I have a huge collection of clothes (more womens than mens, truth be told), not all the pants fit as well as I would like. Accordingly, I knew that to be comfortable for everyday use I couldn’t shop blindly and hope for a good fit. I would have to go the conventional shopping route.

I had a pair of men’s jeans from American Eagle that fit me well. Based on that and the selection I saw online, I decided to give them a shot. Once there, I quickly settled on a pair of their Artist bootcut low rise jeans in an x-long, cuz “I gots legs for dayz yo!” I was curious to try the Boyfriend jeans in a more straight leg, but that style may be discontinued as I could not find it in the store.

I went for the dark color version of the jeans to help hide the masculine shape of my legs just a little bit more. The jeans were a good fit. The stretchy Artist jean fit snugly through my hips and upper legs and then relaxed around my knee and gently flared at the cuff. I was initially concerned that the flare was too much but once I put on my shoes that concern diminished. The bootcut flare on this style pants may still be a bit on the large side for my liking but I decided to go with it. 

Admittedly, one of my chief concerns was how my butt would look in them. I have a rather flat posterior and so my butt really gets lost in most of the sloppy fitting guys’ jeans – happily, it looks better than it ever has. I’m not creating anything I don’t have, I’m not about to pad anything, but it definitely helps me show off a bit. 

As curves are concerned, the front of the pants does showcase more than what folks with penises are probably used to. It’s not extreme, it’s just that we aren’t accustomed to seeing our form showing through (a trend that I would love to see reversed). The pants have enough compression to keep anything from being a spectacle. This aspect of jean fit does mean that the type of underwear I wear matters much more. I’ll touch on this in my next article but suffice it to say that the tighter you can bundle everything together the better the fit looks.

Now that I had found my pair of pants the only thing left to do was put them on and go outside. During my first wearing I was a little self-conscious but not because of anything I noticed from other people. It was just a reticence based on the fear of what could happen. Truthfully, if people were looking at me, I didn’t notice. I honestly didn’t even feel like I was making a scene. I was just being me. 

That last part is important because I have noticed that I am happier that I now wear these types of pants. They say (i.e. studies have shown) that people who have traits which cross the (artificial) gender divide have higher self-esteem than those who rigidly conform to it. My experience reinforces this finding. Living more authentically for me brings me joy, staying hidden does not.

After multiple outings in these new jeans I love them more each time I go out. There are differences based on what I’m used to with guys pants, that is inevitable. I am noticing more and more how they give me a feminine look, more than I had anticipated. However, I have come to love this as well. 

I have always been shamed for my thin body by other men. It used to bother me that I wouldn’t be perceived as masculine. Now, I thank my lucky stars that I didn’t end up with the compacted muscular frame I wanted as a kid. My tall lanky build lends itself well to my desired style of dress. I enjoy seeing clothes hug my body and accentuate the thin form that I have come to love. It’s all very wonderful to experience.

At this moment, I am wondering how to maintain my blend of clothes come summer (jeans are too hot in warm weather). I’m currently exploring women’s shirts to wear with my guy shorts as well as looking for a few styles of womens shorts to pair with some of my more form fitting shirts. This is an exciting new frontier for me and as few people seem to talk about this type of thing I plan on detailing my experiences here as I go along my cute, little, merry, crossdressing way.

Until next time, join me in obliterating those gender boundaries my beauties.

Footnote:

I have resorted to generic terms of men and women, masculine and feminine, for the sake of clarity. However, make no mistake that if these labels don’t fit you, then trust me when I say that I see you, you sexy gender trail blazing thang you (I really don’t talk like this, lol). I am also aware of the argument that there are not women’s clothes or men’s clothes, but just clothes that anyone can wear. I find validity in this viewpoint. However, for me there is a distinct appeal to wearing something that I know is designed for women. I also enjoy referring to it in that way. I feel sexy wearing “women’s” clothes. Doing so allows me a rejection of masculinity that feels more complete than wearing gender neutral clothes would.

This likely stems from the fact that I am exploring the identity of being genderfluid and with that the recognition that I sometimes feel a little more masculine and sometimes a little more feminine and never fully one or the other. For this reason, I’m starting to hedge on calling what I do crossdressing. Until I come up with a better term then this description will awkwardly suffice.

Article soundtrack: Every Time I Die – Post-boredom. Every Time I Die – Ebolarama. PUP – Totally Fine. Bayside – Strangest Faces.

Male Crossdressers Are Still Here

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.