Managing Gender Dysphoria

Photo by Rayne's Avante-Garde
Article By E.S. Wynn


Gender dysphoria is a very personal thing. In my own life, it has been a constant companion, insistent and powerful.

Transitioning to your true gender is one way of dealing with gender dysphoria, but it isn't the only way to move through it. Being unable to transition because of costs, commitments, fears or any other reason can leave trans people feeling trapped, which can in turn intensify existing depression, dysphoria and other such maladies which arise from the stress of one's self image (or soul) not being aligned with the gender of their physical body. Whether you transition or not, if you are trans, you have to take care of yourself, and one important part of that self-care is managing your gender dysphoria.

It's also important to remember that no matter what you may feel in your deepest depressions, you're not alone. You're never really alone, and you don't have to struggle alone. If your feelings of dysphoria are so intense that you have thoughts of suicide, it is important that you seek help and talk to someone immediately. There are professionals out there who understand and who see gender dysphoria as a symptom rather than as a disease (or worse, as something to be ignored.) You might also consider ways that you can begin to transition, even if only partially. Even small adjustments can help ease the discomfort. In my own experience, I have found that even just painting my nails or shaving my arms has helped immensely. Consider changing things up within your wardrobe or your personal aesthetic so that they fit more with the gender that you identify with.

For me, the easiest way to manage gender dysphoria has been to experience life as the highest realization of myself possible as often as possible. Makes sense, doesn't it? If your soul doesn't match your body, then change your body to match your soul and you're golden. For many, that means medical transitioning, but that's not the only way to go about it.

I have a rich fantasy life. There's a reason why I have almost seventy books in print and the vast majority of them feature female main characters. There was a point in my life where I lived within my writing, where I lived as a woman 8-10 hours a day and fell asleep at my keyboard dreaming of being someone other than the man I had to be while at work and in public. Through writing, I sought my highest self and lived within it. In art, there are no limits. If you yearn to experience something completely, one of the easiest ways to do so is to do it through art, whether it be painting, prose, poetry, or any other creative medium. Do not limit yourself—refine your technique, explore and expand. Go beyond your gender. When you envision the highest version of yourself, are you male? Are you female? Are you someone or something else entirely? What kind of individual are you? What are the traits of that ideal self that you resonate with most strongly? What kind of clothes do you wear? What kind of work do you do? What time period do you occupy? What planet? What universe? There are no limits and there are no expectations in art. Even making a list of what comes to mind can help immensely.

Videogames can offer another easy way to mitigate the effects of gender dysphoria. Many games these days offer players the ability to create custom characters with different unique physical characteristics, or at least give players the option to choose the sex of their character. Having the option to play as a female has been a powerful way to keep my own gender dysphoria in check in the past, especially with games that have compelling and gripping storylines which draw the player in completely.

Social interactions with real people while embracing your true gender can help immensely as well. One way that I’ve done this is through crossdressing, then going out with friends to places like the Lavender District, where I can dance and listen to good music in an environment that is (mostly) safe for trans individuals to express themselves openly. Another way that I have experienced social interaction while living as a female was through the anonymity of the internet. In my early twenties, (when I was absolutely terrified of crossdressing and the social implications of being outed for it,) I would spend time with a group of friends I met on Starcraft who knew me only by my gaming handle. To them, I was (and had always been) female. Our group was mixed as far as gender goes, three women and four men in all, if I remember correctly. At that time in my life, the hours that I would spend talking about music, writing and pop culture with the friends who knew me as female were an incredible haven from the gender dysphoria, and one of the few that I knew of at the time.

Certain spontaneous indulgences can help here and there as well. Next time you're feeling pressed by dysphoria (or even just frustrated or depressed,) ask yourself what you really want to do right now. At times, when I have done this, the answers have been conflicting. "I want to take a bath. I want a nice cup of tea. I want to dance in the rain." No problem. Fix yourself a cup of tea, run a hot bath, put on some good music, then turn the shower on lightly so that it sprays a soft rain of lukewarm water over you while you relax. Combining elements like this doesn't always work, but creative solutions can often be playful and fun, breaking the heaviness which comes with depression and dysphoria. Don't think that you have to limit yourself. Make time to be alone and to take care of your mental health in the best ways that you can. Make it fun. Make it simple. Make it relaxing. Feeling good is an important component in battling your gender dysphoria and keeping its impact on your life as minimal as possible.


If you have a story about your own experience with gender dysphoria or have some useful tips that you’ve used to manage it in the past that you’d like to share with the readers of this blog, please feel free to contact me through the contact form here: [link] Make sure you have javascript enabled or the form will just display a blank page. If you’d like to share your experiences living as a trans person (or your experiences of living with someone who identifies as trans) drop me a line through the aforementioned contact form. I’d love to hear from you, and I’d love to share your perspective with our readers. Thank you!


- - -

On Dysphoria

Photo by Rayne's Avante-Garde
Article By E.S. Wynn


I've never been a fan of the words "you don't understand what it's like," but there are times when I've wanted to say it. If you've never experienced gender dysphoria, it can be a really difficult concept to wrap your brain around. For most of the population (or so statistics seem to indicate) there is no feeling of dissonance between gender (how we see ourselves inside) and sex (what we were assigned at birth.) You’re either born male or female and the way you feel and see yourself in your mind’s eye is completely in alignment with that. You look in the mirror each day and see a person you recognize as you, as the you that you have always been, and you don’t generally find yourself daydreaming about a better life where your sex completely matches your gender. Gender dysphoria is an interesting thing to live with, and in this article, I’d like to try to help shed some light on the experience for those who are curious about what it is like.

To start, I’d like you to imagine something. Imagine what it would feel like if you woke up one day and everything in your life was the same as it is now except suddenly everyone saw you as if you were a different gender than you have been for your entire life. For example, if you are a heterosexual married man, imagine that you woke up to suddenly find yourself in a world where everyone else saw you as a lesbian female and would expect you to dress the part. Imagine the social pressure if you suddenly had to conform to western feminine beauty standards (plucking, concealer, leg shaving, etc.) but didn't feel like it. You go into work, and your boss expects you to wear a dress and makeup, to wear nail polish and shape your hairy (mannish) eyebrows into something more feminine, but that's never felt right to you. Imagine the dissonance you would feel with the world around you, imagine the constant cloud of little judgments that would follow you wherever you go because you don't fit in, and worse, people see it, even if you do everything you can to embrace the sex stereotypes that have been assigned to you. Now imagine dealing with that for your entire life, hiding and changing in little ways so that people don't judge as often, or as harshly.

That's a basic overview of my experience with dysphoria. For as far back as I can remember, I have felt uncomfortable adhering to the male ideal, resonating more with mothers, caretakers and female role models. In one of my earliest memories, age two or three, I remember arguing with my father and mother about it, asking them if they were absolutely certain I was a boy. To them, as parents in a small town in the 1980's, staring down at a naked toddler, the answer was laughably obvious, but to me, inside, I wasn't so sure. I didn't feel like a little boy, even that early on, and the feeling has continued and stuck with me for my entire life. The times when I have been the most comfortable in my body are the times when I have been able to look past the male and simply be who I am inside. In practical application, this has mostly taken the form of simple relaxing diversions (like playing video, paper or board games as a female character) but it has also manifested (as I have matured and become more secure in my identity) in more overt forms of expression, such as cross-dressing and choosing a more feminine name (or nickname) for myself. It’s actually the main reason I have always published under the moniker E.S. Wynn—it’s innately androgynous. It reflects the decision very early on in my career to avoid being tied down to one gender or another. When I chose it (in my early twenties,) I was still considering a complete transition from male to female, and wanted to minimize the effect such a transition would have on my career, if I was to make it.

I know that, in order to simplify my explanation of the experience of gender dysphoria, I’ve talked a lot about beauty standards and fashion stereotypes, but it is important to realize that this is just a simplification. Gender dysphoria is not short hand for “the urge some men have to wear lipstick and dresses.” Gender dysphoria is the ever present feeling that transgender people have that our inner selves, our soul or personality, or however you want to look at it, does not exactly match our outer selves. Sometimes this can express itself in the urge that some men have to wear lipstick and dresses (female fashions feminize to the outside eye, which can make it easier to feel at home in a male body) but that is not the only way it manifests. It’s a silly idea to think that all women wear dresses, or that a dress is needed to feel feminine. Gender dysphoria is simply a sense of unease and self-awareness centered on one’s own gender, but it can be very powerful, so powerful in fact, that it can lead to suicidal urges in some individuals. Those individuals who consider (or choose) suicide in response to a strong sense of gender dysphoria are not doing so simply because they feel they cannot wear the kind of clothing generally associated with the opposite sex. They do so because they feel a conflict between the person inside and the body outside, and they don’t know how to address it, live with it or fix it.

I hope this article has given you a greater understanding of what it is like to live with gender dysphoria. I’ll be talking more about my own experiences as a trans individual in future articles, (including techniques I’ve developed to help deal with dysphoria) so check back every Wednesday to learn more.

Do you have a story about your own experience with gender dysphoria that you’d be willing to share? Contact me about your idea (or send your experience so that it can be shared with the readers of this blog) through the contact form here: [link] Make sure you have javascript enabled or the form will just display a blank page. If you’d like to share your experiences living as a trans person (or with someone who identifies as trans) drop me a line through the aforementioned contact form. I’d love to hear from you, and I’d love to share your perspective with our readers. Thank you!


- - -

Safe (And Scary) Trans People

Photo by Rayne's Avante-Garde
Article By E.S. Wynn


Even before I came out openly as trans, I found myself having to reassure people that nothing in my life was going to change, that I’ve been living as I am for my entire life and that I have no interest in transitioning to female. I had to soothe their fears and make them feel safe. I had to explain the differences between gender, sex and sexual preference, and every time I said something akin to “I’m transgender, not gay” or “I’m on the transgender spectrum, but I’m not transsexual,” I felt a bit like I was throwing someone else under the bus. I felt like by having to reassure people that even though I have chosen to identify as transgender while not choosing to transition or to pursue men, I have done them (and my greater LGBTQ+ community) a disservice. In identifying as transgender, I become a representative of the minority, in my own little tiny way, even if only just for one or two or ten people. I become a representative, and yet I’m set apart from the big scary unknown world of men who become women simply because I’m different from the people who choose to go further. I’m not a gay-club man in a wig screaming in the streets of Greenwich Village. I’m not modifying my body or demanding that people use different pronouns to refer to me. I’m a safe trans person. I’m tolerable because though I use the big scary “T-word” to identify, I’m not one of the “terrifying and weird” trans people.

That honestly pisses me off, because it shouldn’t matter how far I, or anyone else, wants or plans to go in pursuit of their identity. It shouldn’t be terrifying to interact with a trans person at all, regardless of how distant their lives are from the concept of “normal” established by conservative American ideals. I hate that people fear us, any of us. I hate the sighs of relief when people ask “does this mean you’re gay?” and I have to say “no,” and explain the differences between dysphoria and androphilia. I hate how conditional and fickle people can be when the question of “how transgender are you?” comes up. When someone asks me how far I plan to take “this transgender thing,” I am of two minds. My authentic feeling, my honest internal truth is that I don’t plan to take it any further than I already have. My rebellious side sees the blatant transphobia in the question “how often are you going to dress up?” and I want to grin and say “every day, constantly, even while I sleep” just to force them to face their fears. In reality, when I dress as a woman, I wear some very stereotypically masculine gear (battle jacket, combat boots, often pants, etc.) because the artistic expression of it is what makes me feel good. I don’t need special clothes to feel like a woman. It’s part of who I am. I’ve felt like a woman my entire life no matter where I am and how I’m dressed. When I pull on my full gear, (including wig and padded bra) I do it for the art of it. I do it for the aesthetic, and considering what a pain in the ass it is to pull together the full artistic outfit, I don’t see the point (for me) in doing it full time. It’s not practical. I have books and articles to write.

But you can bet your ass that I’m inclined to pull on full gear for every poetry reading I do of my book “Trans Physical Dynamics,” or for my upcoming book “Red Gender”. I’d do it for gigs too if I happen to find a punk band at some point that is looking for a trans vocalist, and also truly at any point if it can be used as a tool in a specific setting to reach a group of people and lessen the weight of judgment that is heaped on trans people of all types (especially the ones that aren’t “safe” like me.) The fear that is leveled at trans people is disgusting to me. No one should fear us, any of us, in any way, regardless of how we choose to express ourselves as transgender individuals. We’re just people, all of us, and the degree to which we conform to gender stereotypes should not be a measure of our worthiness, our reliability, our empathy, our intelligence or our moral character.


- - -

Coming Out

Photos by Rayne's Avante-Garde
Article By E.S. Wynn


Happy Litha! It seemed appropriate to post this today, in the full sun of the longest day of the year. It’s also PRIDE month, which I think makes it even more appropriate.

It's taken me a lot of time to reach a place where I can openly admit that I am a transgender individual. As someone who has experienced gender dysphoria for my entire life, I fall within the spectrum. It's important for me to acknowledge this myself, and also for me to be open about it because of the limited (and sometimes mistaken) information about transgender people currently available for mainstream consumption. I really respect the bravery of people (including friends and family) who are transgender and who have chosen to transition socially and medically to the gender they identify with inside, but that is not the path for me, nor is it a universal reality for all people who live with gender dysphoria or who identify as trans.

Most of the time, when you see me in person, I won't be adhering to any kind of feminine beauty standards (meaning, I'll look like a guy. It's more practical for me anyway.) My relationship with Alex is healthy and happy, and she's known about my gender dysphoria since before we were even dating. We've talked about it extensively. Heck, she even took the photos and helped me with the makeup. I have no interest in transitioning medically, socially or legally. Pronouns matter very little to me. You can call me Ellie, Earl, brother, sister, dude, whatever. My soul is firmly female, but I've been living in a male body for thirty-three years now and I've gotten used to it. It has its advantages.

For the most part, nothing will change, except that I'm finally being open now about something I've kept hidden from almost everyone for my entire life. Being open about it is a necessary step for me in feeling more comfortable with and accepting myself just as I already am instead of living under an armor of cultivated masculine traits that keep me on edge whenever I'm in public. I plan to write a series of articles on my experiences as a trans person (I actually have several here already) and hope to do interviews of other trans people who are open to sharing their experiences as well. I want to talk about gender dysphoria and help increase awareness, visibility and understanding so that those who are weirded out by trans people (or the transgender label,) because of bad information (or a lack of information) can see that we're not weird or scary at all. We're just people as ordinary and unique as anyone else.


- - -

On Preference

Pink Carbide - By Dannonlee

As humans, we tend to like to put things into boxes. We like definite answers more than spectrums and gray areas. When I was first exposed to the concept of what it means to be “transgender”, it was in the form of flawed information. For me, even through my early 20’s, I thought that transgender literally meant a gay man who liked to wear dresses. I didn’t realize at that time that women could be transgender, or that sexual preference is not linked to gender identity. What I discovered by being brave enough to really wade into queer culture and do the research necessary to understand trans issues (instead of avoiding them out of fear) is that transgender as a term is an umbrella. It is a spectrum, and has nothing to do with preference.

It is a heteronormative idea that women who identify with male gender and men who identify with female gender must be homosexual. This mistaken idea comes from the normalized idea that men always mate with women and women always mate with men. This, of course, erases homosexual, bisexual, pansexual, asexual and all other preference identities. The fact is that some women, whether they were born as women or something else, are sexually attracted to other women. We tend to call these women lesbians (or bi, or pan, if they are not exclusively attracted to women.)

This basic broadening of concept is pretty easy to grasp. Where it gets fuzzier is when we dig deeper into gender and stereotypes. If a woman transitions to male and identifies clearly as male, looks male and changes his legal documents to reflect his male identity, one might say that his label (in regards to sexual preference) is pretty clear. If he’s into women exclusively, he’s heterosexual (even having been born female) and if he’s into men (exclusively) then he’s homosexual.

But what if an individual is born male, identifies firmly inside as female, doesn’t have any interest in transitioning his/her body (transgender without being transsexual) and is exclusively sexually attracted to women? Does that make *him* a lesbian? Is it transphobic for bio-born women who identify as women to tell such a man that he cannot use *their* label? Does it even fit him, really? How would such a person communicate his/her preferences to potential partners? How would two such individuals in a relationship describe their preference or the nature of their relationship?

The thing is, they shouldn’t have to. Yes, labels and boxes are part of our experience as humans in Western Civilization. Yes, we like to categorize and define things that are a part of our experience (especially if those things are just coming into the range of our understanding for the first time.) We like solid ground, but at the same time, it’s also important to mind our own business when it comes to what other people do in the bedroom. It should never be required for anyone to have to explain their sexuality or sexual preferences, but human beings are a curious lot and it will come up. As such, there are certain scientific terms that exist to define specifically what a person’s preference is (instead of using potentially vague terms like gay and straight.)

Androphilic individuals are individuals who like men and male traits. Gynephilic individuals are individuals who like women and female traits. These are easy to remember when you consider that Andro- is a Latin prefix meaning “Man” and Gyne- is a Latin prefix meaning “Female.” Think “Andrew” (Andro) and “Jenny” (Gyne) as a way to remember the difference. The –philia suffix should be easy for sex-obsessed apes such as ourselves. It’s often associated with all kinds of taboo acts of a sexual nature. These terms, of course, (Androphilia and Gynephilia) describe only exclusive preferences. Bisexual (attraction to men and women both) Pansexual (attraction to all, including gender identities outside of the binary) and Asexual (attraction to none) identities do exist, and people of all kinds inhabit these identities. As stated earlier, transgender is not a sexual preference, nor is it associated or linked with a specific one. It is something separate entirely. Transgender as a spectrum includes people who literally transcend the binary (the two categories of gender, male and female) in a wide rainbow of different ways. Transgender identity is about how you see yourself, how you identify, not about what kind of people you find sexually attractive.



- - -

On Badassery

Our ideas of what it means to be “strong” and what it means to be “weak” are too simplistic. One might even argue that they’re misogynistic, if one buys into the idea that women are naturally more emotionally expressive than men are. A “tough” person in idealized form in the west seems to be a person who never cries, who never allows themselves the release of pain necessary to keep from bottling everything up inside until it explodes into psychosis or manifests as a truly spectacular meltdown.

I’ve given this dynamic a lot of thought in my life. I’ve even meditated on it a bit in my article “Why I Need Feminism”. I have always prided myself on my strength, my toughness, my ability to take powerful emotional hits and push through them without falling down, without breaking apart and giving up. I’m proud of how tough every major life event I’ve lived through has made me. When I look back at the person I was five years ago, (or ten, or fifteen,) I can see a marked improvement. I’m proud of the scars that I’ve earned, and I’m proud of how, with every deep wound I’ve been dealt, I’ve gotten a little tougher, a little more resistant.

The first time my heart was broken, I didn’t leave the bed for two weeks (except to eat, etc.) I spent those weeks reading books my ex-girlfriend loved and trying to find the smell of her hair on the pillow. To be fair, my whole life had fallen apart and the breakup was just icing on the proverbial cake, but when I look back at how I handled it, how hurt I was over the ending of a toxic relationship with that horrible, manipulative, misandrist abuser, I almost want to laugh. I look back and think, man, I was weak. I had a lot to learn. I certainly had a lot of maturing to do.

I bounced in and out of a chain of toxic relationships after that, and with each one I got a little tougher. I suffered some major failures and had some dreams crushed, but each one that fell apart made me stronger. I lived through some gnarly situations, dealt with legal threats, death threats, and a crazy ex-girlfriend who stalked me on campus so relentlessly I had to start carrying mace with me. Eventually, I got married, and amidst the maturing that happens when you become a husband (especially a house-husband who has to do literally everything for your partner) I reached a solid place where I felt like I was safe, like the worst of the pain was over. My father used to tell me that the only thing that scared him, the only thing he thought that could break him would be losing me. A year after I married my first wife, I told my father that the only thing that scared me, the only thing that I thought would break me would be losing her.

When she reconnected with an old boyfriend of hers and suddenly demanded a divorce in late 2014, after four and a half years of being in a relationship, it broke me, utterly. My worst fear, my only real fear at that point, had come to pass. When I look back at that moment, I look back with mixed feelings. I was tough enough not to retire to a bed for two weeks, but I was weak enough that I still took her back four times after that, even against the advice of friends and family.

What I look back on with a sense of pride though is how I handled the pain those first few weeks, those weeks when the shock was strongest and the knife in my heart was at its keenest. I took a week to pack everything I owned, arranged transport and decided to move back to my hometown. I had no reason to stay in the city, so I figured I’d start fresh closer to my friends and family. For the first week back in the Gold Country, I hauled brush from dawn until dusk and consumed little more than chicken broth and coffee. I listened to U2’s “Wake Up Dead Man” on repeat and during my nights I spent time researching my options, looking for jobs locally and looking into joining the US Air Force. In one week, I lost 30 pounds and two belt sizes. In two weeks, I went from being able to run a quarter mile without stopping to being able to run a mile and a half without stopping. When faced with adversity, I chose to fight. I took action and got strong. When I look back now, I smile a little, because the foundation I set down during that year, during one of the most hellish years of my entire life, established me where I am today, and left me a great deal stronger than I was before.

So what does it mean to be badass? In my mind, the West has it all wrong. A badass isn’t someone who carries a gun and who holds her tears inside despite a soul that’s so wounded it’s tearing itself apart. A badass isn’t someone who gives up and collapses and cries at the drop of a hat either. In my mind, a badass is someone who feels, who cries openly when the pain is great, who releases anger in creative, non-destructive ways, who sees a problem and chooses to move (or fight) past it. A badass is someone who knows that the pain will pass, who focuses on the future, and on how to make things right again. A badass is someone who might be the victim of others, but who chooses to not remain a victim. A badass is solution-oriented. A badass feels pain, but does not indulge in it. A badass says “yeah, this sucks, but I’m going to fight until it doesn’t suck.”

That’s what being a badass means to me.


- - -

Why I Need Feminism

There was a time, not so long ago, when I thought feminism was useless.

Looking back at the past, I could see the ways that feminism had been a powerful force for positive change in our society, and how it made things more equal for both sexes. In our modern day, however, it mostly seemed like a lot of misandrist whining. Now, there is certainly a toxic side within feminism which trends toward misandry (consider the folks who sent death threats to scientist Matt Taylor during ShirtGate) but that’s not what I’m here to address. No movement is without its shadows. Trust me, I'm no friend of the MRA movement.

But I did think about flying their banner once. I thought about it because I saw a problem. I saw a lot of problems, and I didn't know how to fix them or who was causing them. I think it's a logical (if flawed) step to take to say "Female problems are addressed by feminism, so men need a movement to address the places and ways that we feel oppressed." The problem is, you have to be able to differentiate between genuine oppression and the kind of daily, ordinary sufferings that we all deal with. Most MRAs I've observed voice that they feel oppressed (essentially) because they don't have a  female partner (who complies with oppressive female beauty standards) to have sex with.

I shouldn't have to say this, but that isn't oppression. Being lonely sucks, but it doesn’t mean that you are being oppressed.

So how are men oppressed? Why do we need a movement?

I would argue that we already have a movement: Feminism. Now, four years ago I would have laughed at anyone who'd written that statement. Why? Because feminism is for women, right?

No. Feminism is for men and women, because the issues that it addresses directly underpin the issues that create a need for a movement that addresses the ways in which men are oppressed. As in, solve the issues that feminism exists to tear down and you solve the issues that oppress men.

So back to the question: how are men oppressed?

Let me digress with a personal example:

I grew up surrounded by "strong women." They were in my TV shows, they were in my books. Every woman in my family was "strong." They were warriors who wore pants, who openly wore tattoos and shaved their heads. They were the kind of feminists who marched in the streets and wrote letters to congressmen about the kinds of oppression they faced. They built and founded rape crisis centers and open-carried handguns.

That's awesome, but there's a problem with it. The problem comes with the word "strong."

When a woman shaves her head, she's strong. She's bucking the trend. She's no longer a long-tressed beauty slave fluttering her eyelids at the men of the world. She's standing up and owning herself and saying "fuck that patriarchy noise" in a very aggressive way. When a woman binds her chest and wears a tanktop or fierce piercings or identifies as "butch", she's strong.

But why is she strong? Because she's bucking the established beauty standards of the world around her? Because she's standing up against oppression and censorship?

One could say "absolutely not. That's not the reason."

Why?

Because if you flip it on its head, a woman who is confident in skirts and long tresses and who loves living a housewife life is not considered strong.

Because if you go further, a man who is confident in skirts with long tresses and a househusband life is not considered strong, even though he is bucking the trends and standing up against oppressive beauty standards.

Now, I personally think that anyone who does what they want without bowing to oppression is strong. The problem isn't what I think. It's what pervades the mainstream. Take this example: two people, a man and a woman, could work at the same company and crossdress and only one of them would get sent home or fired on the spot. So let's think about this: Why is it (socially) okay for a woman to cut her hair short and wear pants to work but it is not okay for a man to wear his hair long and wear a skirt to work? Why is it so offensive for a man to wear a skirt and heels that people will actually jeer at him while he walks down the street?

Because of all the issues we have around what it means to be a man and what it means to be a woman. Because we still see masculinity as strong by default, so when a woman "becomes" a man, she is seeking to become stronger, and that’s good. When a man embraces his feminine side, he is seen as weak. In fact, the more he embraces his feminine side, the weaker he becomes, and it's worse because he's doing it to himself. He's not being torn down or emasculated by some other person. He's self-emasculating. He's choosing to be weaker.

Because he's choosing to be a woman, or woman-like, or rather, to embrace an aesthetic that our society assigns to women as a woman-only thing.

There's a lot more to it than that, of course. Men cross-dressing brings up all kinds of issues (homophobia and sexual deviancy among them) rooted in how we view men and women. As someone who has battled dysphoria my whole life, who enjoys cross-dressing and even considered transitioning to female at one point, I can tell you that I've seen all kinds of unaddressed issues that even the most enlightened carry around (myself included.) I've found myself having to explain that just because I'd love to go to work in an outfit so good that I have passing privilege and I'm virtually unrecognizable doesn't mean that I have any sexual interest in men. I’ve had to tell family members and friends that even the simple act of painting my nails doesn’t mean I’m signaling to the world that my back-door is open for a back-alley rendezvous with strange dudes. If anyone tells you that women are no longer seen as sex objects, then ask them why people assume that a man who dresses as a woman must be trying to seduce men. See the issues in that? See the homophobia, the toxic masculinity, the objectification of women all rolled into one there? The assumption that, if you’re dressing up in any particular fashion, there must be a sexual reason for it? A desire to attract the male eye? A desire to be objectified? I both love and hate it when people assume that I am gay or bi. I love it because I’m confident in my sexuality and I know there’s nothing wrong with having any kind of orientation. I love it because it creates visibility for the oppressed, even if I’m not part of that minority. If someone else identifies me as belonging to a particular group, then I give that group a voice, even if it is just a whisper on the wind, a glance in passing. “We are here, and we will not hide ourselves. Get used to seeing us.” Going deeper, we can see that men who embrace their feminine side, or who have a sexual preference that people assign a notion of femininity to (drawing from heteronormative conditioning), are oppressed by society, and they are oppressed because we still see stereotypical expressions of femininity as weak. If you are a man, you must be strong. If you’re not, there’s something “wrong” with you. If that something isn’t immediately visible (i.e. you aren’t gay,) then it must be something deeper and “darker.” That’s the rabbit hole people go down, and it all comes from the notion that “women’s” clothing is worn only to titillate, to attract men for sex.

What we need to teach is that the character and confidence of anyone is what determines their strength, not how they dress, what their gender is or what their sexual preference is. Whatever you wear, rock it. Do it for you. Be you, and be confident in it. That's strength. That's how you fight oppression. That’s how you break apart the societal standards that oppress all of us at once.

That's why I need feminism.

- - -