The Evolution of Gender

Gender is a complex and wonderful thing. Currently we are living in the golden age of gender. Folks now have a greater awareness and social acceptability for more types of gender expressions than has ever happened in the United States. The flexibility is there to explore and become who we are and it is my greatest hope that this trend continues into perpetuity. I am a benefactor of this recent trend. I guess it would also be fair to say that I have also helped establish a social climate in which freedom of gender expression is welcomed and encouraged. So has anyone else who has acted in an accepting and loving way towards queer folk (so thank you).*

There was a time when this wasn’t always the case. Twenty five years ago Matthew Shepard, a young gay college student, was lured into a deadly trap in Laramie, Wyoming. He was tortured and beaten, then left for dead tied to a fence. When he was found his face was solid red, covered in his own blood save for where his tears ran down his cheeks. He would later die from his injuries. Now I don’t know what Matthew’s gender was specifically, but his murder was a signal to queer folks everywhere about how safe we were.

This is the world I emerged into as an adult fresh out of high school. There were people in my home town who actively cheered on the murder of this young person. I remember having to actually push back against their sentiment. To these bigots, he was just “another faggot who got what he deserved.”

During this time, I had firmly accepted that I liked dressing in women’s clothes. It will come as no great mystery then why I chose to keep this part of me to myself. My partner at that time was seemingly hostile to me dressing this way as well. I had once shared this aspect of me with her to have it thrown back at me in a dismissive way a month or so later. It would be another 15 years before I told anyone else what I did behind closed doors.

In the meantime, I began compiling a secret collection of women’s clothes. I went so far as to have a post office box so that any items I ordered would not come to my home address and raise the suspicion of my partner. At the time, I didn’t put a label on the activity of dressing femme. I didn’t think much about what it meant for my gender. I was married and in a monogamous hetero relationship so my sexuality and gender just kind of seemed like moot points. I was pretty sure I was at least bisexual, but I wasn’t at liberty to explore anyhow.

However, moot points don’t stop the tide from rolling onto the beach. So I went on with my clandestine activity of dressing up anytime I had the house to myself. I would almost frantically change through my clothing collection trying on one outfit after another while flitting around the house. It was fun, sexy, and reassuring. That was enough for the moment.

And yet still, it wasn’t truly enough. I wanted to share this with my partner, which I felt I couldn’t, and more to the point I really wanted to dress this way in public. I chalked this up as a partial result of wanting to be able to share this with someone, anyone, and also because I was denying myself a form of expression. I was also young and full of hormones. I wanted to be out and about, looking as sexy as the women my age who were strutting their stuff around college campuses and malls (yeah, I’m that old). Why couldn’t guys dress femme without recrimination? It was a societal aspect that I would often lament.

There was another interesting phenomena that happened around this time. Trans people were beginning to become vocal and as a result visible. They were staking out their identities and this was rankling a lot of bigot’s noses. 

In a shitty rural town a few miles outside of my shitty rural town there was a person who had come out as trans and had transitioned to living as a woman. As you can imagine, virtually no one was willing to accept this person for who they were. I remember a male coworker who was a cousin to this woman would refuse to use her name or feminine pronouns when discussing her. By deadnaming her he was making a point, chiefly, that he was an asshole. It didn’t matter that she was family, all that mattered to him was to display intolerance and homophobia with vehemence. Anyone who has ever spoken to someone like this coworker of mine will readily recognize that for these people insecurity is the hallmark of their masculinity. It is a weakness parading as a strength.

I had never met or seen this young woman, something which remains true to this day, but I had an attraction to her nonetheless. Admittedly at the time, the very idea of her as a transwoman was fetishized a bit in my mind. However, there was something much greater at work. I felt a kinship with her. Somehow we were the same but I couldn’t put my finger on it exactly. I had some hunches though. 

First, I figured that she was more liberal than most of the folks with whom I was surrounded. Keep in mind that the world had yet to be introduced to Caitlyn Jenner so I didn’t know that people could be queer and still support a political ideology that would legislate them out of existence.

The other part of my attraction was that I knew there was a tie between her being trans and me dressing femme. It took me a while to sort through it, but I realized that there was a shared experience between us. She was able to ditch certain gender norms (admittedly in favor of others) and live how she wanted and I was trying to do the same. She had conquered the gender expectations against which I was still struggling.

Meanwhile time prodded along, as it always does, and I left the relationship I had previously mentioned. Soon after, I moved across the country and into a much more progressive area. It was here I immediately realized that I had an opportunity to live openly as a queer person. I embraced it head on and soon after I had my sexuality tacked down as pansexual. I also started mentioning to people that I crossdressed.

The term crossdresser for me was a peculiar fit. This term had previously seemed like a fetish label for folks and not an identity term. As such, I was reluctant to adopt it. As I went on dressing in women’s clothes I realized that this activity went deeper than just a fetish. The term crossdresser felt good, as it was the most accurate one I had to describe myself, but it still fell a little short of full representation. I knew I was missing something but I didn’t know what.

I started doing the mental work concerning whether dressing femme meant that I was really trans. At that time in my life, all I knew about being trans was that those folks wanted to live as the opposite gender into which they were born. 

It is true that there is a part of me that would love being a woman. I revel in the idea of slipping into women’s clothes and filling them out in a way that is more conducive to their design. I would love to have small A or B cup breasts. The idea of having sex as a woman is appealing as well. Not to mention that when I wore a skirt or dress outside as a woman, no one would give it a second thought. I would be turning heads for all the right reasons. As an aside, I fully realize that being a woman comes with its own set of hassles, mainly in the form of men who have toxic behaviors.

The idea of transitioning to a woman is tantalizing, but it would also mean giving up a body I have come to love. I still wanted to enjoy my body and to occasionally revel in my flat chested appearance. I love how my penis creates a bulge beneath women’s clothes and I could never give up that sexy bump. I knew pretty quickly that transitioning wasn’t something that I was interested in mainly because the effects were permanent. If I could pop body parts on and off like a glorious gender bending potato-head doll then that would be amazing. This would be the life experience which would bring me the greatest level of happiness. Short of that impossibility, staying male bodied and adorning myself in femme attire is next in line for my quotient of greatest happiness.

I kept the label of crossdresser for 8 years. I continued dressing in private and I was able to find some partners I could dress for here and there. Still, my urge to dress femme in public had never left. In fact, I felt it all the more. I was denying something intrinsic to who I am. 

This led me to start exploring gender terms and concepts. Originally, before I began reading about identity terms I thought bigender might describe me best. What ended up resonating with me most though was the term genderfluid. Simply, this was because my gender identity and expression do not seem fixed. At times I feel less or more masculine, less or more feminine, sometimes like a man, and oftentimes like a woman.

Later on I read an article and realized that being genderfluid places me in the transgender camp. I had two feelings simultaneously. The first was, “am I trans enough to adopt the label?” I quickly realized this was nonsense. The bigger feeling washed over me in a wave of warmth and acceptance. I felt as if I was home. Every emotion and experience of my life came rushing in to fill the space behind the door I had just opened. It all made so much sense now. My feeling of connection to every trans person I had ever met or read about hinged on more similarity than I had realized. We direct kin in our big beautiful queer family.

This self realization, coupled with my desire to dress femme, pushed me to take it out into the streets. I started mixing women’s clothes with men’s and strutting around town. I just bought my first pair of women’s boots to wear in public and little by little I am actualizing what I had merely dreamt about for two decades.

I feel like in many ways that I have finally arrived. That I am where I am meant to be and have finally figured out the nuances of what makes my sexuality and gender work. However, life is good at surprising us and while I don;t know where it will take me, if I stay true to my path I know it will be to a place of happiness.

The other day I was driving to meet a friend and I had a pair of women’s jeans and a women’s cardigan on and I remember seeing my body as I drove down the street and I looked feminine. I felt my heart swell.

Some may find labels limiting and I completely understand what they mean. For me though, I have used them to derive an identity that was previously out of reach. I am pansexual, I am genderfluid, I am transgendered, and I feel awesome.

* I don’t want to assert that the world is a completely better place. The recent mass shootings, protests against drag queens, and the abysmally low rate at which those who are cisgendered even consider dating a transgendered person are all evidence that we have many prejudices and hatreds that need to be relinquished into the dustbin of history.

Article soundtrack: Ten Foot Pole- can we stop trying to win, White Lung- hysteric, No Trigger- the honshu underground, Mobina Galore- whiskey water, The Used- people are vomit, Bunkface- toxicated, Mixtapes- c.c.s., Adventures- i can’t say

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.