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

Tips For Guys Wearing Women’s Jeans

In a previous writing I discussed my new found interest in blending my wardrobe and wearing some pieces of women’s clothes in public. During my online searches for alternative ways of dressing I found a lot of folks asking if guys can wear women’s clothes. Now who knows what they meant by this. Some were probably interested in venturing out and expanding their self-expression. Others still, were probably trying to make their shame someone else’s problem by policing gender.

For those hoping to branch out and find women’s clothes to wear then yes, you can absolutely put on something cute and flit about town. Since I have some experience in this, I thought I was in a key position to help men out in their quest.

For those who feel the need to police how others may dress; see a therapist.

I must caution that 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.

I’m going to begin talking about pants because I think that is an easy way to introduce a piece of women’s clothing into your wardrobe in a more subtle way than a shirt or a dress would be. Because we often slowly explore things rather than jumping straight in with an entire wardrobe, this seems like a good place to dip in the proverbial painted toe. So let’s start at the top and work our way down by learning a little about women’s pants.

As you will soon find out, I will be referencing the penis and testicles fairly often as that is a chief issue with form and function when crossing clothing styles. So don’t get squeamish on me now.

Where to shop

The only way you are going to know what size works for you is to try some things on. When I started crossdressing I bought things discreetly online. I’m also on a budget so that often means getting things preowned from places like Ebay. The key here is to find sellers who actually do the measuring of their garments. If you buy new from online or even online auction sites, just go to the clothing manufacturer website of the item you are thinking of purchasing and use the size chart to your advantage.

You’ll need to pick up a clothing measuring tape (also used for body measurements) to find out what your actual measurements are. Clothing sizes are wishful thinking at best.

If you are in the store, finding your size is much easier and probably cheaper in the long run. Grab a couple of sizes that you think are approximate and head to a dressing room. 

Waist

In women’s clothes waist size is a series of numbers that has nothing to do with any real world number. I find that I may be anywhere between a size 4 and an 8 depending on which brand and style I have in my hands. It’s infuriating. It would be great if all clothing manufacturers actually used real world measurement as a size. Nothing is true in clothes anymore though and we carry shame about the actual measurements of our waist in part because clothing manufacturers are doing stupid shit like this. 

However, here we are so this means you’ll have to know your actual measurement if ordering online. Do not use the size of your men’s pants because that shit ain’t real either. The men’s jeans I buy list a 28 or 30 waist, but my actual waist measurement is closer to 32 inches.

Stretch fabrics will also measure differently than non stretch fabrics. Within the same brand you may find that a size 6 for instance will fit you in a stretch jean but will require a size 5 in regular jean fabric (or that scenario in reverse).

Some pants, generally non-jean materials, have a size of small, medium, large and so on. The manufacturer’s size chart is a good tool here if you can’t try these pants on in person.

If you’re going to try things on in a store then knowing your measurement isn’t as important as you can just try them on and go from there.

Rise

The rise in a pant is the measurement from the bottom of the crotch to the top of the waist band. There is ultra-low (rare nowadays but popular in the late 90’s), low, mid, high, ultra-high (popular as of this writing and goes by various names).

Low rise works for some guys but others will find it uncomfortable. If you are thin and a low-rise waist doesn’t create a muffin-top kinda scenario for you then you might find this style a good fit. 

An unintentional benefit of these pants is that because they have less distance between the bottom of the crotch and the top of the waistband the zipper is placed lower and takes up a greater area of the front of the pant which makes standing to pee a bit easier. However, the low rise also means it’s a short zipper so it’s still not the easiest feat when it comes time to go fishing for your penis. 

While you’re wearing low-rise pants, bend at the knees and squat to the floor. Where do the pants go? If they start to make you look like a handyman who could use suspenders then go with a pair of pants with a higher rise. You could also look for a low rise style which doesn’t fit snug on your upper thighs which can sometimes contribute to pulling your pants down during such a maneuver. However, I’m not here to yuck your yum, so you do you my dear. 

If the pants stay mostly in place and require very little repositioning when you stand up then this could be a good rise height for you. Even with little movement, I still prefer to wear a belt with low rise pants just to help keep things in place. It keeps the pants snug on my butt, which makes me look better and also gives me a way to accessorize by adding a masculine or feminine flare.

Mid rise is probably where most guys will be comfortable. Pants with this level of rise sit where most people (aside from your 90 year old uncle Harold) wear their pants. A mid rise pant will move around less when bending over as well. I’m guessing that a belt here is still most people’s friend, but you’ll know more about that when you try them on.

High rise pants are a bit of a mystery to me. I don’t have the body type to make these look good. Even if I did, my main concern would be function. Women’s high rise pants often still retain a  small zipper but it is positioned even higher than most other style pants. That means that your deliciously naughty bits sit below the zipper behind a piece of fabric generally bisected with a seam. So if the seam pushes too far up you can end up with a moose knuckle look. Now I am a fan of seeing curves in this type of scenario but it may not be your thing so just keep that in mind.

The other concern is that a higher zipper placement means nothing is lined up to pee whilst standing. You’re going to have to drop trow in order to make that happen. Welcome to a woman’s world.

The other issue with high waisted pants is that they are made for wider hips and a narrower waist. Flaunt it if you got it, but most guys are not built like this so I could see how the fit could miss the mark on multiple fronts.

Leg/Fit Style

Flexibility can be an issue for a number of the styles we are talking about here. Try a pair on, raise your legs, squat down, and just get a sense of how much flexibility you will have. I love how some jeans look but have passed on getting them due to a lack of functionality.

Skinny/Jeggings

Skinny jeans are those which generally hug your legs from start to finish. These also include jeggings which are extremely stretchy jeans that fit like leggings. Be careful with jeggings because a tight fitting ankle is often easy to slide on, but difficult to get back off when dealing with larger feet and ankles. I do not recommend a low rise in this style as crouching will always pull the pants down.

Additionally, while jeggings can be made of extremely stretchable fabric they are often too tight to allow complete free range of motion when raising your legs or bending down. I am extremely thin but even I find these uncomfortable. The flexible fabrics also double to serve the wearer with a mission impossible; positioning your genitalia in any way that could be considered aesthetically pleasing. So while these might be fun around the house (something I still don’t find to be true) they lose utility whilst going about your day.

Bootcut and Flare

These are pants which get larger towards the leg openings. Men’s pants have boot cut options so that style is not a foreign concept for most guys. Flare pants generally have a larger leg opening still and will definitely denote to others that you are wearing women’s pants. It’s a stylistic choice for both of these and some are more subtle than others. Generally these pants fit tighter on the upper leg and relax more as they go down, but each brand is different.

Wide Leg

Similar to boot cut and flare but more relaxed through the thigh and often have a flare at the bottom. Width can vary from slightly wide to extremely wide based on style preference.

Straight

Pretty simple. Just as with guys pants these are a straight shaped leg from start to finish. If you want a feminine look but still retain just a hint of that mysterious and wonderful androgyny then try these as they are also slightly relaxed.

Mom jeans

Yup, here we are. These are jeans that generally have a high waist but a more relaxed fit through the thighs and legs. Some taper toward the leg openings and others are more of a straight leg. It is a broad category and each manufacturer has their own variation on this loosely defined style.

Boyfriend jeans

Like mom jeans, this one is hard to nail down, but these generally hover around a mid-rise waist and have a more relaxed fit somewhere between straight and wide leg. However, like mom jeans, designers are mixing and matching to such an extent that it is hard to tell what you’ll end up with in terms of rise and leg style.

Leg length

Finally something we can talk about that is simple. These run the gamut of petite/short, extra/short, petite, short, regular, long, tall, x-long, and so on and so forth. The best way to find this out is to measure your inseam and use fitting charts online or try them on in the store. Interestingly, leg length is usually accurate so the inseam listed on your guy pants should transfer over to the size chart for women’s. While we are deathly afraid to know our waist size apparently we have no such qualms about the length of our appendages, well . . . most appendages.

Cautions

So here are the extra little things you should know about women’s jeans. 

The tighter the fit through the hips then the less room you will have for your genitalia. I buy pants that fit fairly snug through the hip area. While walking I do not notice anything but I am used to being cradled by brief underwear anyhow. If you wear boxers, yawn . . . sorry I drifted off there for a moment, then this will be a much different transition for you. 

Sitting down is another thing altogether. Things get a bit tight but I honestly enjoy the feeling. It’s a reminder of what I’m wearing and I’m not uncomfortable, rather I’m just getting used to a different fit. I don’t notice it much anymore but I still wouldn’t want to wear them for a 12 hour cross country drive. For most situations they work just fine. Your results will vary and there is no way to know until you give it a go.

I alluded to this but allow me to say outright that your underwear selection matters … a lot. Those boxers I mentioned before are not going to work. In fact, just throw those out all together, you’re not doing anyone any favors. In boxers you are hanging free which means that the seam in women’s pants are pretty much going to position everything to one side or another which isn’t going to look good at all. Something that holds your bits in a pouch is going to be much better as everything will stay a bit more centered. All briefs are not created equal. I have found that the tighter a pair of underwear holds me in place then the better off I am wearing them with my women’s jeans. Still, there is no ideal positioning unless you’re going to tuck entirely. Something is going to favor one side or another. For me I just try to minimize it as much as possible but then embrace whatever I can’t hide.

If you are doing a low-rise jean then some underwear may creep above the waist band. This could be a style that might work for you if your undies are fashionable and less so if your waist band says Fruit of the Loom. Luckily, briefs also come in different rises so if this is a continued problem I’d try a lower cut.

A tighter pants fit also gives a better look at your butt. The drawback here is that the lines your underwear creates can be problematic. Jock-strap underwear may create a dented line where your butt meets your legs as can some briefs. Plus if your goal is to show off your butt (and I have long thought that it should be) then, in my opinion, a thong is the way to go. The pants will be able to cradle each butt cheek without the added resistance of a full panel of fabric from conventional underwear getting in the way. This will allow your posterior to have as much definition as possible.

The other drawback is pants that make your butt look awesome are also just as form fitting in the front which leaves no room or flattering way to position a penis and however many testicles you have. It’s an unfortunate reality, but here we are nonetheless.

Women do benefit here by having seamless underwear. Unfortunately, those will not work well if you have a penis as the lack of seams just allows everything to fall out. 

If you’re going to go the full crossdressing route or are transitioning then there are what they call gaffs to help hold everything in a more concealed position, but I do not have experience with these so I cannot comment further. There is also a company called FIT4U Solutions that claims to have compression underwear without the need for tape or gaff. Again though, I have no experience with these.

The most functionally infuriating thing is pocket space. Women have been rightly complaining about this for years. This is something that you need to check out when you’re trying on pants. Some styles have so little pocket space you’ll wonder why they are even there (some pockets aren’t there). I have a small minimalist wallet the size of a debit card and I can barely fit that into my back pocket. My keys, also minimalist, occupy an entire front pocket. My phone, which is a smaller model (notice a pattern here), sticks out of the other front pocket. Admittedly, I like my phone showing on the front because it is what I’m used to seeing when women wear those pants. Therefore, it makes me feel more feminine. In reality, it’s simply a result of poor design. If I was doing anything with a lot of movement I wouldn’t feel that my phone was safe, but it’s fine for just strutting around.

Color

The last consideration is color. Conventional wisdom says that if you’re looking to conceal some of your masculine lines then dark colors will help accomplish that. I think that’s true but you also have to like how you look in them and so if you find a pair of jeans that you really like and they are in red, white, or whatever then I say just go for it. Wear what makes you feel good luv.

There you have it. I hope I have covered everything you wanted (pun partially intended). Folks with penises can absolutely wear women’s jeans. In fact, my opinion is that these bodies look all the more dreamy in femme fashion. I also vote for letting your bulge show, but given that I really need to work on controlling my drooling in public, I’ll leave that choice up to your preference and comfort level which is all that really matters anyway.

Go out, have fun with it, and let your femme flag flutter like a summer dress in the breeze.