A Crossdresser’s Journey

15 min readJan 2, 2021


How I have been managing a lifelong crisis

I hope my story will help you understand the journey so many crossdressers are on.

This is generalized from my own experience [I’m 70 now], supplemented by that I have heard from fellow crossdressers over decades.

if it is of any use for others who are struggling in the same way, I will share my crossdresser’s journey from childhood to today. Both male and female children will take this journey, until it isn’t necessary anymore.

The urge to crossdress:

  1. Comes as a whisper- an awareness of clothing as a badge of gender and a lingering gaze at the clothes that should somehow be ours. We are taken aback when given the toys we don’t want as or only choice.

The first time:

  1. A piece of desirable clothing is unattended and we pick it up, just to see. We try to see how wearing it might feel.
  2. We try to make a dress out of a plastic bag or see if we can somehow make our haircut more boyish.
  3. Another person may offer us a chance to play dressup
  4. We may ask directly- can we?

The shutdown:

  1. We are angrily told we may not.
  2. We are called out, shamed, or physically punished when our first foray is discovered.
  3. We see and hear punitive enforcements coming from everywhere, covering how we conform to gender expectations in every little detail of life.

Our response:

  1. Secrecy- we hide.
  2. Depression- we are unable to act in accordance with our natural impulses and no one seems to want us to.
  3. Split personality- we have an outer and inner life
  4. Therapy-rare since it is expensive, but the desire does not go away- it is too fundamental. It can only be managed in the face of duress.
  5. Half measures- online community chat, PRIDE marches, drag humor, political work on gender freedom.
  6. Pain- We are locked in a tragedy- we are joyfully right in our hearts and deeply wrong in the eyes of so many around us.

But we keep trying:

  1. We try with everyone- to see if somehow we can be accepted.We hint around, we ask plainly, we oversimplify.
  2. Sometimes it’s a conditional yes, at arm’s length.The bargain is that we can exist but not be actually acknowledged. There is no hope of warm welcome, ever, it seems.
  3. We come to believe that for most people around us, our wanting to crossdress in a deeply personal way [as opposed to a joke, or trivial experiment, or artistic provocation] feels … too strange, too misguided, too …well,wrong.

The pain is widely shared- it is societal dysfunction preserved against all good sense:

  1. Those around us who support us are burdened as well. The social pressures are costly to their relationships with us and others.
  2. Gender rules are so pervasive and enforced so thoroughly that the urge to crossdress creates a lifelong existential crisis that destabilizes our lives and those around us.

The future? Mixed cultural signals:

  1. Trans celebrities pried open the public awareness that gender appearance and behavior can be fluid and …well, actually not a problem.
  2. There is a very public backlash that condemns transgender individuals. Yet more conservative religious families are coming to feel that maybe God did create their own precious trans child.
  3. Females are increasingly entering professions that embody masculine traits, and the envelope for acceptable behavior among women is expanding rapidly.
  4. Fashion as a barometer of gender rules- women’s clothing is trending towards freedom from previous restrictions, with the understanding that it is bold and practical, but not challenging men’s status.
  5. Teens embraced genderfluidity en masse. Boys are wearing makeup.
  6. Among adults, when the interest in letting men boldly wear dresses is tested, it still fails quickly. It is too great a leap.

Is the urge to crossdress and affliction or a blessing?

  1. Every attempt to disconnect from the power of clothing fails. Why? It is the way we signal to each other almost everything about us.
  2. Clothing is the visible tip of a hot emotional iceberg. That which lies unseen is the wholeness of our personhood. We see it, and we want others to see it. We know ourselves as good- why is it so hard for others?
  3. For most of us, each day is an exercise in trying to minimize the negatives and increase the positives.
  4. If we stay in the dark, clinging to our crossdressing liferaft- we are getting by, but it is a stunted life and we feel it.
  5. If we can find room to gather a big closet full of clothes that express our feelings, we can enjoy the natural pleasure of dressing in the company of our camera or mirror. But cameras and mirrors are substitutes for actual persons smiling at us. They do not deeply satisfy.
  6. Managing our desire to accommodate the feelings of those we hold dear, creates a lopsided relationship.

Is there a light at the end of the tunnel?

  1. We want ‘only’ to be able to live naturally, with a direct line between our desires and our actions.
  2. The valid role of social norms is suppression of behavior is intended to block expression of harmful desires. So the question is really about harmfulness.
  3. The argument for social repression us that our desires are illegitimate since not in line with social norms, customs, and assorted religious doctrines. I have yet to see any statement as to actual harm to anyone from crossdressing, either to themselves or to others.
  4. Our desires are normal and ubiquitous. Parents have to continually instruct their children as to what is allowed or expected with respect to their assigned gender. Crossdressing is the expression of the desire to live in our natural wholeness, expressing all that is found in the multi-dimensional human personality.

It is clear to me that it is the repression of crossdressing that is harmful to everyone. It is useless, ineffective, and unnecessary.

The harm of gender norms is well understood- but they are persistent. Individuals have to save themselves.

My jailbreak:

  1. I really thought about all of this and realized that regardless of the origin or justification, crossdressing itself is harmless to others, and productive for me.
  2. When I ventured out and found that society has evolved to a point where violations of gender norms are tolerated pretty well, as long as I am not threatening anyone’s sense of sexual safety or comfort in their own identity.
  3. I found that gender is a two part event- messaging and receptivity to the message. And being careful for others is not too difficult. I display but do not assert my femininity. I don’t signal flirtation with men or competition with women. I use men’s restrooms. I talk about ordinary things with people in the ordinary way. I am not straining., and there are many layers to messaging that have to be accounted for.
  4. Marriage is a challenge, since the interplay of gender is a 24/7 practice. Gender styling agreement forms the floor on which we dance.

Am I there yet?

  1. No- in that each day is still a discovery. Crossdressing turned out for me to be the tip of a very large iceberg of submerged personal identity- wishes and capacities.
  2. Yes- recognizing that late-life understanding may be too late for some things. I am so thankful I have made so much recovery. I have days where I feel I have finally arrived! I said to myself once, in an exalted state- “I am so happy I can die! “

This is the end of the journey- unification at last, and now, just to live- facing the challenges of each day as a whole person, at last.


Below is a long background discussion, if you are a person who is struggling to understand how all this comes about.


Crossdressing may appear in the life of someone you love as a young child, or around puberty, or ‘out of the blue’ as an adult. It feels instinctual, and therefore like a perfectly natural activity.

Clothing is an integral part of being ourselves in the world, and clothing is functional, purposeful, important messaging. We are taught about clothing from an early age. It is as important as smiling.

We become more focused one day on some aspect of the “other” gender’s clothing. On reddit today, for femboys, it is thigh highs and spinny skirts. For an older generation of men, it may well be VS exotic lingerie. For females, it might be flannel shirts and sturdy fabrics. We recognize the thing we are missing, that we want to have, to wear, and to be accepted in society as eligible for.

We want to feel what the ‘other’ gender is feeling. Of course, that means we want to feel something we already feel, but which we are not permitted to feel. It is set aside for the other gender, and the clothes are a gender privilege.

We find a way to have the experience- we borrow someone’s underwear, we send for a dress or shirt online, or we fashion a skirt from a plastic bag, just to try, desperately- to …know- to enter the mystery.

And we find success- we feel expanded, better, freer, more right and peaceful.

If we are very young, as I was, there is no doubt that our desire is legitimate. It feels inherent, as normal, valid and harmless as liking the color blue.

Soon enough we are told it is wrong.


Most of the time, a bid to crossdress as a matter of ordinary life is rejected.

When I was age 5 and proudly showed my father my discovery that my sister’s underwear was quite wonderful, he reacted with a threat of public humiliation. I wondered, why is this such a problem? But he was obviously serious, and his intent was to extinguish my desire.

All of us have learned this lesson from so many sources, often only in conversation about some unfortunate crossdresser. We see a disgusted look, suffer through a lecture on cultural norms, cringe at abusive shaming, or are traumatized by threats and violence. We feel in the intensity of rejection in every quarter that crossdressing, and by extension, we must not disturb this nest of hornets around us.

We wonder why this is so viciously enforced, but it doesn’t matter- case closed.


It is almost always the case the that there is no path forward to tolerance and acceptance. The practical choice for any crossdresser is to retreat, to ‘go into the closet’ and keep it a secret.

Crossdressing is then like a waking dream, releasing us to feel better, but only in our imaginary world. We feel euphoric, and try to understand why this is such a powerful experience. Perhaps this is the reason it is being suppressed so violently.

I learned that I needed to keep my simple natural desire to myself. The collateral damage was that I could no longer share a good portion of my actual thoughts and feelings with my parents, or anyone else.


Crossdressing occupies varying portions of a person’s identity. For some it is a furtive occasional exploration, for some a kind of a hobby, and for some an explicit rebalancing of emotion and relief of tension, or a stepping stone into a new identity experienced in what feels like a new world.

Only a tiny minority of crossdressers find social settings or long term relationships that embrace their sense of flexible gender.The vast majority of crossdressers suffer extreme interpersonal isolation, perhaps only for this portion of their personhood, but it is a necessary part.

In an effort to feel connected, to feel expression and interaction, crossdressers may resort to erotic fantasy. The need for this workaround vanishes when crossdressing can be part of ordinary life.

A tiny subset of crossdressers find community as drag performers- with ersatz social acceptance in the formality of dramatic presentation and reactions of the audience.


Sometimes a celebrity can take advantage of their status and will claim the right to enjoy flexible gender expression, and each new announcement helps elbow some new room in the social structure. From the beloved figure of David Bowie, who established a permanent beachhead for genderfluidity, to Laverne Cox, who has warmly proved transition as a positive fact.

Thousands of crossdressers find some companionship in online communities, where it is at least possible to have anonymous acceptance among like-minded people,sharing pictures and discussing concerns.

It’s not enough. So many, across all cultures, crossdress alone. Many never know they are part of a very large group.


For nearly all of us, crossdressing remains a desperately solitary pursuit. We desperately wish for acceptance into the company of others, and imagine this utopia with the help of our mirrors and cameras.

Suppressing and hiding cross-gender feelings is just as destructive as inhibition of any other fundamental human process. When you can’t speak about something, you can’t clearly think about it either. This disables healthy development and the communications needed to build trusting relationships.

Shame, ostracism, and violence are the tools used to discourage every violation of gender rules. Conforming to those rules is specifically to combating punishment by isolation.

Those who are welcomed into the company of real people find deep, deep relief- even from a few moments.


Society is structured around the division of labor, power, and privilege by gender, Every aspect of our lives from day 1 is conditioned by our classification at birth as male or female. Even though very young boys and girls share more similarities than differences, daily enforcements are applied by parents and society to separate the genders, to draw boundaries, divide labor and status by gender, and actively extinguish behavior and thoughts that do not conform to the planned adult gender role.

A simple example will show the good and bad results.

Girls, regardless of their natural inclinations, are required to pay closer attention to the things that women are assigned responsibility for- like child or elder care. Society benefits from specialization of emotional labor, sort of. But caring is a necessary part of our humanity, and in this short-sighted assignment and confinement of females we lose the massive benefit of actual skills possessed by females, and give too much responsibility to the male half of society that is all too often emotionally crippled and therefore performs poorly.

Concurrently, as a boy ages, the reasons he is allowed to cry are rapidly reduced. He learns to suppress and disregard any emotion connected to vulnerability, and this has the benefit of simplifying the path to decisive, logical action. But this desensitization to the real vulnerabilities of humanity, and the simultaneous tendency to overweight the accepted dominance emotions like pride and predatory desire has yielded the toxic masculinity that has corroded so much of our society.


Many children suffer from gender norm enforcement- some slightly, some horrendously, yet we continue to yield to a pointless social compact with circular and self-justifying: ”Strict binary gender rules are how we define individual destiny. We use severe punishments for non-compliance. Yes, many may suffer, but punishment ends when they agree to conform. It is that important.“


There are many reasons parents and proxy authority figures give for persisting in slicing up kids’ psyches by anatomical classification- e.g. ‘this system is preparing you for the real world”, and if that isn’t enough of a reason, then religious texts, basic reproductive biology, long historical practice being evidence of enduring value, practical arguments about division of labor, etc.

These arguments would be more convincing if gender norms were progressive and made life actually easier. By evolutionary theory the arc of history should bend towards social norms that expand the capacity of a population to enlist all help from diversity in survival of our species. Our gender norms are still crude and restrictive, so it is no wonder so many of us argue for the freedom to contribute from our individual strengths.


Clothing is modern mankind’s primary signal of gender, class, role, nationality, etc. Dressing is simply the quickest path to try to partake of the world of .. not just the ‘other’ sex, but any different culture, status, or job title.

Wearing the clothes assigned to our sex is one of the first things we are required by others to do in life. Clothing norms are the first norm enforced, and the most heavily enforced. Thereafter we are taught about, earn, and keep our status of ‘man’ or ‘woman’ by maintaining a high level of conformity to the rules for our two respective teams.

We honor a child’s desire to dress up in the trappings of a princess or a soldier, or mom and dad, or any role in society that is specialized and honored. We celebrate the uniforms we designate for sports teams, and for a wide range of technical professionals from police to nurses.

Crossdressing is the expression of a common human urge- to transport oneself into what might be a more fulfilling world. It is dressup, but dressup is tolerated only if doesn’t seek accommodation or change in the lives of observers.


The term ‘crossdressing’ implies crossing over a barrier, and that barrier is the presumed all-important line between being a ‘man’ and a ‘woman’, that determine all the attendant powers, privileges, expectations, and constraints.

Yet, we all can see that males and females have so much in common, contradicting the justification for role differentiation. Tropes such as ‘males are better at math’ end up falling apart on close inspection, Separating out the effects of child-rearing and social pressure and educational practices, I’ve come to see that that the only inherent and uncrossable distinction between being male and female is our reproductive biology.

The rest of our heavily defended gender ‘differences’ that are enshrined as innate norms are just what is taught as if inseparable from primary and secondary sex characters, but at heart it is just performative culture.

We humans are perfectly suited for flexible expression, and most people dream of widening their opportunity for expression.

The ‘line’ that crossdressers ‘cross’ is imaginary.


Thousands of decisions are constrained each day to fulfill our designated role as ‘man’ or ‘woman’, to achieve and maintain our status as one or the other.

There are several important ironies to notice. First, that the cultural edifices of ‘man’ and ‘woman’ are treated as if a natural destiny based on anatomy. From the moment at birth where the first words are ‘It’s a boy [or girl] !’ everyone joins in the story that male or female anatomy is the fundamental, primary, and determinant qualification of future identity. A boy will be a ‘man’ and a girl will become a ‘woman’.

There are years of specific training involved, encouraging or suppressing any personal characteristics that do or don’t match those assigned to and expected of ‘men’ and ‘women’. It is a tortuous process for many children. We need only watch children for a few minutes to see them managing the conflicts that arise between their natural behavior and expression and the rules that society has imposed on them.

Children clearly want to escape this regimen,and object until they are silenced. Girls dream of ways to transcend the roles outlined for them, and boys wish that they could enjoy a moment fully free of jockeying for dominance.

It seems a hopeless quest. The magnitude of interlocking expectations and the daily reinforcements from every corner are daunting. Yet, the whole human being wants expression. Some children cannot be ‘corrected’. Tomboy girls and ‘sensitive’ boys are the persistent reminder of what is suppressed in the character of so many children and lost to society.

Children often feel uneasy with their new job as ‘man to be’ or woman to be’. So many fundamentals of personality are involved and would naturally tend to guide us to be more boyish or more girlish, or to mature into a man or woman. But we are not allowed, if our anatomy does not meet the standard per societal rules.


Children will try to keep what they can of their nature as they mature, and, as it becomes clear that portions of ourselves are being suppressed- it is a tension. Whether you are a woman realizing that your words are discounted in the boardroom or bedroom, or a man who wishes he could be less stoic or brutish, these tensions limit our personalities and thereby our society’s potential to improve our collective circumstances.


It is not difficult to see both the benefits of and resistance to equal status of women and liberating females to be all that they can be. The new focus on toxic masculinity is circling around the issues and will eventually have to call for structural change. It will be very good to populate society with males who are emotionally competent and communicative. All such changes would make our society much more resilient in the face of everything from pandemic recovery to armed invasion.

It is obvious to even a casual observer that if capable females replaced less competent males in important tasks, our society would operate more smoothly! Many men are actually warmer and more effective caregivers that many females. The list goes on.

So much of human suffering is driven by psychic damage inflicted on children via gender norm enforcement.

The ‘patriarchy’ has been identified as a problem, but it’ survives by the complicity of females- even if more or less unwilling. The ancient Greek tragedy called ‘The Women of Troy’ explores the horrific and interacting consequences of the gender expectations that still poison our world, and show both compliance and self-defeating self-interest of women.

I am confident that if women refused to go along — men would cave- in an instant.


It is no surprise that the first thing many of us will do, to revive our experience of that which is lost, is to reach for the dress of that gender. Clothes are important, as they are designed to be an unmistakable signal of status as man or woman, and therefore ownership of rights to behave and feel in those ways. Ironically, that is because it is often not obvious at all if one is male or female, and making this distinction right away is all important, as it then guides what we say and do with each other.

It doesn’t take a rocket scientist to understand that we are stripping children of their full range of humanity, and that the results are not clearly that good! The ridiculous need to establish the rights of females even to vote, the cost of the brutality inflicted on boys as well- what are we waiting for?

Yet, as soon as a boy admits he wants to wear a dress or a girl is too sure of herself, all hell breaks loose.

It is wrong.

Crossdressing doesn’t fix it. It is all too little, a bandaid, a dream. It is a way only to maintain some shred of all that we have lost.

And, you don’t need my story to see this. Please take the steps you can to free yourself and others to recover our natural personal wholeness.




We can all help each other a lot by freely expressing our gender