The Crossdresser and the Transwoman – The Psychology

Please note that this article in no way replaces seeking your own medical advice, and nothing within this article constitutes medical advice or direction, but rather a point of view, general experience and informed opinion 

“Crossdressing and Transgender Identity: Similarities and Differences Through Psychology”

Introduction 

Throughout my work as a medical practitioner, one of the most common subjects during my psychoanalysis sessions with transgender women is how to be sure whether they are transgender or cross-dressers.  In both cases, both are born male, they both wear female clothing and have similar interests in clothing and makeup; both enjoy the experience of being and feeling feminine. It should be observed here that despite the similarities in appearance, transwomen and cross-dressers are very different.  You may have asked yourself or be reading this and saying something like ‘which one of these am I, where do I fit in?’ 

I am a specialist in Gender Care; however, I want to make it clear that this article's main objective is to bring a modicum of clarity to a person's feelings and to highlight any possibility of making any life-changing decisions should be discussed fully.  I want to be clear that there is no judgment here, but rather a journey to understand the intricate differences between crossdressing and living as a transgender woman.  What follows here is that there is no right or wrong, superior/inferior; rather, it's distinctly different, although the uninformed and badly educated often get this damagingly wrong. 

Common Life Experience 

All transwomen have one thing in common, and that’s that at some point in their transition, they have cross-dressed.  I have not yet met any transwoman who has not transitioned through this process at some point.  It typically begins as an ambivalent attempt to express gender, which over time becomes a new normality. 

Many of my patients comment that it occurs at a young age (some as little as 6, 7, or 8 years old) when a mother's wardrobe pricks your attention, or your Grandmother's perfume and aroma are much more appealing than the aftershave that your Grandfather wears.  The women's department in your local store becomes a mecca of interest. 

The roots are juvenile here and small, but experimenting with trying on skirts, heels and makeup starts little by little.  This process bleeds in and out of their lives, but it's always there, even when the compulsion and derision all fail to suppress it or, in time, cause further confusion and distress.  For those who live alone, occasional cross-dressing becomes a feature of their lives and is accepted as a new normality. 

Femineity & Living a Covert Life 

It's been years or even decades since it all started.  The wardrobe and closets have become full of clothing, the thoughts of presenting dressed and wearing makeup flood into your mind more often, and further elements such as lingerie or nail polish are incorporated into the new normality. My patients have also commented that crossdressing often leads to arousal and a release of stress and tension.  More commonly its experienced by them as something shameful, unnatural or sinful and should at all costs be hidden from others.  Many go through countless episodes of purging their clothes and even denouncing and deleting their memberships to crossdressing sites on the internet, only to replace the clothes and makeup and return to that normality they once craved. 

Many have found friends in their lives who appear and share similar compulsions and interest and it relieves the feelings I have described above, but it's always there.  Nevertheless, there is always a sense that crossdressing is similar, but not exactly what you need.  Many feel that looking like a woman is simply not enough for them, becoming one…no, it's not what you're looking for, are you sure, Ok maybe...? Oh, I’m so confused. 

This indecision and doubt I have expressed above, whether cross-dressing is sufficient to make you happy or whether you should not only look like a woman but become one permanently, is extremely complicated.  The one inevitability is that you can say that femininity attracts you and that you relish those moments where you can express your femininity.   

For many, their feelings may become distorted or unclear.  I encourage my patients to regress from this emotional turmoil and stress that they must question themselves and concentrate on their feelings. Take a moment to analyse this passage and focus on ‘how you feel’; notice whether any of what I have said resonates with your feelings and beliefs, or maybe you have a much more distinct and alternative experience. 

The Advantages of Masculinity – Being a Man 

Cross-dressers have an advantage in that they can fully enjoy their male lives; they can effortlessly negotiate society with their current bodies.  They have the superiority of having all the male privileges society gives, and they are confident and adept at communicating with others as men.  The act of dressing in female attire is carried out as a momentary pleasure, it's fulfilling, and the thought, steps and process of transitioning full-time are alien and certainly not attractive. 

We would discover that if this were all taken away from the cross-dresser, ordinarily, it would not have a profound impact on their mental health; it's viewed as a recreational escape by some.  In my world, we talk about Gender Congruence and Incongruence, which is that they agree with their gender and looking like a woman from time to time is more than acceptable, and they are content with their status quo. Where the latter is that they are distinctly unhappy and dysphoric.  However, in moments where they have that feminine appearance, feelings may change because of imagination, but beyond that, impersonation, they return to their male persona.  In conclusion, their gender matches their assigned sex at birth. 

The last few paragraphs give you a taste of the most common traits of the cross-dressing community, but they are very different for transwomen.  I would like to remind anyone reading this so far, and due to the negative impact that media can have, I want to remind you that if you relate to what has been discussed, it does not make you ‘inferior’ or ‘beneath’ transwomen.  Even in my clinic and my own socialisation with the crossdressing and trans communities, I constantly hear this incorrect ‘pigeon holing’ where being a transwoman is perceived as the final goal for all crossdressers…this I feel, is an extremely destructive conclusion and thought process, as in the first instance, being transgender is not a choice and should not be viewed as some sort of divine goal or heaven.  Furthermore, everyone is different, and no ‘one size fits all’ doctrine exists.  If you have concluded that what we have discussed here does not fit or reflect your feelings lets move on to the transwoman. 

Transwomen & How They Differ 

Their whole ethos and situation are much different, including their complexity.  There exist several components that are ubiquitous with trans women, whilst some are more individual.  Probably the most compelling and important difference is that they experience Gender Incongruence, also sometimes called Dysphoria.   

A clinical term which means your gender identity does not match the sex assigned at birth. Although you may well have become accustomed to your male body, the interaction with society as a man and being viewed as one.  Some even enjoy some aspects of their male persona, but overall, existing as a man just isn’t right. 

I have seen cases where the Gender Dysphoria and experience is so intense and burdensome that it can reach extremes where a patient may deny being born as a male, discern anything masculine in them as hostile and feel that their current body is a ‘clinical error’ and should be ‘rectified’.  

As time slips by, many start to examine how they would feel if someone else saw them as a woman, especially if there was no need to return to the masculine self, and if their life experience was female.  In my sessions, I see these questions time and again appearing randomly and are not in fact related to whether you are cross-dressing at the time or not.  All these points lead us to probably the most important part of being a transgender woman, and that is two things: time and frequency. 

Psychiatry uses the DSM-5-TR and ICD-11, one of the criteria for gender dysphoria is assiduously experiencing gender incongruence for a period of at least six months (DSM-5-TR) or several months (ICD-11). 

Psychiatry.org - Gender Dysphoria Diagnosis 

Gender incongruence and transgender health in the ICD 

Although the intensity may vary, the feeling is always present.  It should be noted that this long duration is fundamental to understanding whether the craving to become a woman is a product of fantasy, imagination or an authentic aspect of the patient’s personality.  The reader should be clear that gender identity is not a choice, and you are powerless to alter it.  The patient has already definitely experienced bouts of suppression by acting out the traditional ‘masculine’ behaviours; they don’t work, and they won’t work.  I have patients who stress they have tried to convince themselves and explain it as a ‘phase’ or even as a deviated sexual preference or ‘kink’.   

One of my patients attempted to block out and dismiss from their mind the feelings by becoming an outstanding professional in their chosen field, achieving top-tier results in sports, becoming involved in masculine hobbies, joining the military or adopting the role as a devoted provider for their spouse and children.  

For these patients, none of this was natural as they viewed it as forced and a ‘smoke screen’ with one result – not feeling like a woman.  After trying everything you can think of in your power, it still didn’t work, as the feeling would return repeatedly gnawing away at your psyche.  


When Female Clothing Ceases to be Enough 

During my sessions, I suggest that throughout all this that has gone before you, the summation of all the clothing and makeup is only the tip of an ‘iceberg’; there is much more under the surface.  You will not change or modify your personality, but allow yourself a medium to express it.  I encourage you to reminisce about when you were first attracted to a feminine appearance and the desire to experience it.  I will ask them, “Has it altered over time or been modified?” “Has its appearance transpired into something more”? 

For transwomen, I often see that cross-dressing acts as a substitute for a certain amount of time and for some even decades, but inevitably it escalates to where it becomes never enough.  They inform me that wearing female attire is a feeling of affirmation, but no longer satisfying.  After a period, the process becomes a normality as if this is always how you have presented and that you were born to wear these clothes and makeup.  The need to have and maintain that drab and separate male wardrobe with its switching between male and female must end.  Often, their partners and loved ones inform me that if life circumstances force them to revert, it causes much angst and distress.  For transwomen, a feminine persona and appearance is no longer an option; rather its essential to their mental health and well-being. 

Eventually, and for all at different parts in their journey, the full understanding and viewpoint that clothes do not form identity becomes clear and real.  Your identity does not depend on what you are wearing today – it's fluid. I included myself in this next point that women wearing masculinised clothing (jeans and a t-shirt) is not new, and men wearing (kilts) skirts are still men. 

Stare into a mirror and allow yourself to be who you are without following strict gender conventions or acceptance.  After all, being tough and masculine may feel usual and the thing to do, but I can guarantee something feminine will always break through from time to time; many attempt to conceal this so people don’t notice.  There is a feeling that you wish to express your feminine side whenever and wherever you want, freed from the chains and pressures of being a stereotypical masculine man.   

Many of my patients, with hindsight, say that these people replay these events and then realise you have always been that person inside; sadly, some don’t, and that won’t always end well.  It answers their own unanswered questions.   

Beware Jealousy – The Unlived Life 

One of the pitfalls I see in this process is when transwomen in what used to be a heterosexual male/female relationship dynamic; some feel jealousy toward their wives and even other women before or during the early stages of a transition.  As a transwoman, you are monitoring their dress, talk, sit, carry themselves, express emotions and interaction with others attracts you; you are overwhelmed with a wish you could experience those feelings too. Psychology informs us that whenever the emotion of jealousy is raised its seen as taboo and negative, but for transwomen, it’s something we call a ‘projection’ of an unlived life. 

I have seen and witnessed my next point many times in a variety of different forms, that is, jealousy towards transwomen who have already achieved and completed their transition.  You may even compare their transition timeline with yours and imagine if you were in their place – if you now had a female body and were seen as female and a woman.  Following transwomen may become part of your life; their whole demeanour and appearance are something you yearn for and that you deeply want to achieve. 

Although some may argue that this is a natural reaction, jealousy is a poison, and these thoughts can be harmful.  It is extremely important to realise that these women have all taken calculated risks and invested much time, effort and emotional energy in their own transition.  Probably, they have been on their own journeys and experienced the same or similar confusions, doubts and lack of tangibility as you may be now.  Consider that the difference between them and you is time, patience, and dedication, all of which will eventually reveal what's possible for you; as everyone's transition and experiences are inherently different 

Reflection & Understanding Before Changing Your Life 

Transwomen exhibit one common thing, and that is the eagerness and desire to have a female body. Reactions to the male body are distressing and very common, with many reporting an avoidance of personal care and mirrors.  I am certain you have felt the softer skin, seen the curves, the breasts and long hair and some of these may seem out of reach.   

There are several ways to approach and achieve this; cross-dressers often wear silicone breast forms, real hair wigs and various other prosthetics, all of which are temporary and may be removed. 

For transwomen, the second involves Hormone Replacement Therapy (HRT), IPL (Intense Pulse Light Therapy), or laser hair removal or the permanent option for stubborn growth, electrolysis; finally, gender affirming procedures and corrective surgeries.  The latter all are permanent and change the body rather than creating an illusion; however, in the United Kingdom and my home in Australia, there are long waiting lists for surgeries and other procedures, unless private care is an option for many.  In my experience, that’s what many of my patients are committed to; however, this is just not always medically possible or financially feasible for all. 

Beware that the internet is not always a safe and healthy resource for you, as one of the most common sources of information about transwomen is still adult content sites.  I am certain that for many, it may have been their first exposure and remains deep-seated and influential in their beliefs and ideas.  Nevertheless, the acting and posing may appear intriguing, and curiosity is common and understandable.  This type of content exposes transwomen’s bodies and demonstrates the effects of HRT and different procedures, so offering a window into what's possible. 

I will place a caveat here on the above, as there is also an issue where many transwomen adult content models wish not to have lower affirmation surgeries; these women going forward will have issues with segregation from some single sex services; this is inevitable given the map of the world and its attitudes we are seeing across some services and countries at this time.  It also drags those women who have endured the surgeries, and they are also discounted, even though they are no different to cis-gender women other than the uterus and womb not being present. 

Conclusion & My Free Advice 

My professional advice is that it's crucial whether you decide to transition and live your life as a woman or simply enjoy an unburdened life, enjoying a feminine experience and appearance without changing your life. You first need to be sure you fully understand yourself.  I hope this article has brought you some understanding and clarity to a very complex and deeply personal subject. 

If you need a comprehensive assessment of your circumstances and guidance regarding suitable approaches, I recommend initially consulting a General Practitioner (GP), a counsellor specialising in transgender care, or a relevant medical specialist. 

I will leave you with one last thought and say that everyone is different, and some decisions should only be made when there is certainty and readiness to fully change our lives.   

You didn’t become transgender; you were born that way. Your wish is to be seen as the person you have always been.  The people around you need to be willing to see that also; you haven’t just changed on a whim or overnight.