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.

State of the Relationship Address: Call me Jena!

As my partner slid her hands beneath my dress, pushing it up around my waist, I asked “Will you call me Jena?” This is something I had wanted for a long time but for whatever reason the femme side of my gender was rarely on display during my sexual encounters with her. She complied, but I could sense a little unease in her voice as she said my name. So I took over referring to myself in femme ways and relaxing into a roll I so desperately wanted to fill. Doing this for the first time and accepting that part of me was exciting and liberating. Everything inside me had been leading in this direction.

After this experience, I asked my partner how she felt using my femme name (admittedly, something I should have done beforehand). For a little background, my partner is a cis-woman and as straight as they come. By my telling of it, she has never found any part of a woman attractive in any significant way. She is attracted to male-bodied me and yet has been supportive of me wearing whatever female clothing I desire in private or in public.

Still, she said using a femme name for me was not something with which she was comfortable. It did not create any attraction for her. Quite the contrary, I got the impression that it created a kind of repellant visceral response (the opposite of attraction basically).

I want to be clear that I do not fault her for it in any way. While I think there are aspects of attraction that we can control and help shape, there is also a part of desire that cannot be forced. Accepting this duality has been central to my own journey of exploring sexual attraction and even gender identity. I accept and support her boundaries.

Additionally, for about two years we have had an agreement that I could be with other queer folks sexually. For this arrangement I would be non monogamous and she would be monogamous. This was actually her idea initially and one which she mentioned a couple of times before I actually accepted it as a viable possibility. We did this because I wanted to continue exploring my queerdom and retain my visibility as a queer person.  

During that time of being able to “date” (or whatever you want to call it) other folks I had talked to many folks but none who could muster up any interest that went much past the tip of their genitalia. I also found it hard to believe that my partner was one hundred percent okay with this arrangement. Accordingly, I didn’t want to proceed full steam ahead and do irreparable damage to our relationship. As a result, I had only been with one other person who was a dear friend of mine on one occasion.

So when I initially heard that she couldn’t accept calling me Jena I was worried but knew that perhaps I could still explore this aspect of me with others. I felt like I still had a lifeline and an outlet in which to revel in who I was becoming. A week or two later this too came to an end.

My partner told me that while our relationship arrangement made logical sense to her that she couldn’t accept it on an emotional level. Now that she had discovered and spoke her truth, I was happy to focus instead on monogamy. The clarity of monogamy has always felt reassuring and I find simplicity and beauty in the practice.

All of this creates a number of quandaries for me. Is my femme side in any form a problem for her that will eventually surface? For now, I am aware of the possibility, but am accepting that I have heard the truth as best as she currently knows it and am proceeding accordingly. 

The larger issue for me is that now that I am monogamous can I express my femininity in such a way that is still fulfilling for me while not being off putting to my partner? Is it possible to walk this line and leave everyone happy or will tending to her boundaries squelch my identity? Furthermore, is it even reasonable to walk a line at all where gender identity is concerned? Isn’t it more preferable to be who I want and need to be and let the chips fall where they may?

I don’t pretend to have the definitive answers, or any answers, but I do want to talk about what I have discovered while wrestling with these questions.

Realizing My Femme Side

In my past, I had kept my femininity shutoff from the outside world. I was closeted on purpose. Growing up I was surrounded by people who didn’t understand virtually any queer issues nor did they make an attempt. They mainly ridiculed and disparaged those who were different. Twenty some odd years ago, I shared a few pics with the person who was my first spouse. They were of me wearing her undergarments. Later when she was upset about something, she said, “I leave for a week and the first thing you do is dress up in my underwear.” I didn’t know exactly what this meant as it didn’t pertain to the argument at the time but I got the picture. I was expected to knock it the fuck off. 

I had reached out to someone I thought I could trust and I received a scolding that was the death knell to me living openly with her. I didn’t want to experience that again and in small minded (I mean small town) America it was sure to happen each time I tried to publicly become who I needed to be.

So I kept it all under wraps. I dressed in femme ways only when I was alone and my partner was gone. I never mentioned it to her again. Later with other partners I was able to bring this side of me to life but mainly did so only in the bedroom; the most private of spaces.

This year though I have started wearing women’s clothes (pants and shorts) out in public. It is still less than I would like to wear, but it is a process and I am in the middle of it. Still, dressing with femme clothes in public is removing the secrecy around my gender. It is helping to give me some visibility as a queer person.

Likewise, when I was chatting with folks on dating apps I was leaving it up to people to call me by my masculine name or my femme name. Those who chose my femme name lightened my step. It felt foreign to be called Jena but it also resonated with me and made me happy. Having this quality in my life makes me feel more rounded and gives me visibility as a queer person. It’s as if my figurative masculine edges are being sanded down a bit. I like that.

What I’ve Learned . . . Kinda

This revelation is another step in understanding where I have been and in some ways where I am at now. My desire to be femme during intimacy was because I had kept this side of me in relative secrecy. I’m curious to see if having the femme me on display in public will erase the need to be referred to this way occasionally by my partner. If this is the case then I’m not walking any figurative line at all. Problem solved.

Conversely, if I still have the urge to be more femme than my partner can handle then it will be unfair to myself to continue walking someone else’s path. It seems as if this is the more likely outcome. While dressing femme in private led me to also dress in public, the occurrence of the latter has not diminished the occurrence of the former. So it seemingly follows that using my femme name in public is still going to be something I desire during intimate moments as well, though that experiment has yet to be conducted.

It must be admitted though that in a monogamous relationship that one half of the experiment is missing. I can’t use my femme name during intimacy to see how much I need to express that part of me. I just have to wait and see if I think I want it used. If I do, the relationship will end and I’ll have to hope that I was correct and that I didn’t make the wrong choice. It has become a much larger burden under monogamy than it was previously.

I used to feel as if I had a clean slate to explore and write down who I wanted to be. Now the surface of my slate is hemmed in with words to direct my path. I can write down who I am so long as I do not obscure parts of the slate which already contain the writing of others.

Keep in mind, I’m not asking to go back to nonmonogamy. That didn’t work and anyway, I don’t need it. It’s just that now I don’t know how to proceed. However, proceed I must because there is no other option before me.

I have had a difficult time writing this because I do not truly know where I stand. Each line I put down on the page feels shaky and dangerous. How much of what I write here is being constrained by the boundaries of my partner and by my fears? Truthfully, I do not know. Only time will reveal that answer. I have tried to be as kind and yet truthful as possible. I know that being gender fluid is firmly a part of me. I’m unpacking it piece by piece and while it feels good to do so, I’m scared of the consequences that my thoughts on this page could have in my current relationship. Seeing it all typed out here is less than reassuring.

If the romantic aspect of our relationship does not survive then it is no one’s fault. In fact, it will be for the best of all possible reasons. That my gender identity does not line up with her sexual attraction is certainly no one’s fault. It is just one of those unfortunate things which can occur as people grow.

For now, my partner says she is comfortable with me dressing in femme clothes and is good with incorporating these clothes into our intimacy. This gives me hope and currently I could use a little more of that.

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.