Reflections of a crossdresser

As promised, here is a follow-up post from the last one, where I started to hint about the direction my recent thoughts have been taken me. Some of these might be too intellectual for your tastes. Some might be too obvious. Some might just be a repetition of past reflections: that’s not so unusual, I often return to the same things. And some are merely about wishes, plans, and expectations, most of which will never become true. A few come from discussions with my wife: often she provides a completely different viewpoint which just triggers good answers to my own questions. Oh yes, she’s often very good at pinpointing the true reasons about how I feel and think, and expose them to me in a way I cannot say she’s wrong. She’s often right. And more often than that, I refuse to accept reality as it is, and pretend otherwise.

There is not “one self”

I believe this is something every crossdresser will deal with very early on, but sometimes it’s hardly obvious, and the implications are tremendous — and very liberating.

Consider a “beginning” crossdresser, who just realizes that he feels great wearing women clothing, and now has to deal with the whole package: it’s morally wrong? Am I insane? Am I homossexual? Am I a freak? Do I need medical treatment? Or do I have a “double personality”? Worse than that: is my personality truly female and I just have been pretending, all these years, that I’m male? So why is my personality not aligned with my body? What’s wrong with me? Who did this to me, and why? Can it be undone?

We all asked these questions to ourselves, over and over again, and one characteristic of all transgendered people is how introspective we are. For some, the answer is obvious: I was never born male in my mind, I just happen to be the unfortunate victim of a terrible birth defect, but it can be corrected. For most the answer is not so obvious. The spectrum between one extreme — a clearly cisgendered person — and the other — a clearly transsexual individual — is huge. Between fetishisms, termporary stress relief, dealing with frustrations and depression, there are so many reasons for feeling like we do that only an expert can try to untangle the whole mess.

What helped to me is to slowly accept a very simple idea, which, however, is very hard to accept as true. There is no intrinsic “self”, blue-printed on our neural network, which is fixed and immutable. This should be obvious for everybody: after all, we don’t think and don’t feel like the person who went through the teens in this body we carry with us. And if we go further back in time, it’s clear that we are not 6-year-olds any more: we think differently, we have accumulated experiences which made us “change our mind” (notice these words carefully), we have adapted to a role in society, we model our thoughts based on education, peer pressure, and social conventions. So clearly we’re not “the same person” as we were 10, 20, 50 years ago. For some, of course, that’s a relief — after all, who wants to be permanently stuck in a hormone-rich brain, full of anxieties and insecurities, like we had during our teens?

Nevertheless, it’s also quite clear that we’re not “a completely different person”. That 6-year-old that started to get used to the idea of an “I” inside the brain (or wherever it’s located) has a strong connection to the insecure and hormone-driven teen, which, in turn, has a connection to whom we are (or think we are) today. This connections is undeniable: after all, we have memories of our “past selves” and know that it was “we” who experienced those memories, in the flesh and blood, in the distant past. So there is this feeling of “something” that gets carried along our whole lives. Spiritualists might call it “soul”, “life-energy”, “anima”, or simply “spirit”, or even, more simply, just “mind”. There is a sense of continuity.

All our options in the past made us crystallize an idea of what our “self” is supposed to be. If we’re successful businesspersons and parents, we imagine ourselves as being that kind of person. We model our own behaviour according to the stereotype we have of how a “businessperson” or a “loving parent” ought to behave. These stereotypes come from role models, books we read, our education, the TV series we watch, the peer pressure we are subject, and so forth — sometimes we copy them because we think that’s how we should behave, sometimes we reject them and create our own image of how those stereotypes — or archetypes! — ought to behave. Whatever the means, the end result is that we project upon ourselves and our behaviour a certain image of how we are supposed to think and act in society, and this, in turn, reinforces our tendencies of thinking and acting in a certain way. For instance, if we have this image we ought to be a loving parent, we think and act in the way we suppose a loving parent ought to think and act. The more we do that, the more familiar with those thought processes we are, and the more “natural” they become. As a result, this reinforces our idea of actually being a loving parent, and the feedback we get from our friends and family — “s/he really is a loving parent!” — will further reinforce that idea. So we equate the “I” with “loving parent”, and adopt the qualities and characteristics of what an archetypical loving parent is expected to possess and exhibit.

But we’re not “just” loving parents. This might be true at home, but we might be ruthless businesspersons at work. So we switch roles when at work. We don’t stop being loving parents at home; but we nevertheless become businesspersons at work. So which one are we? Loving parents or businesspersons? Which of the two is “our real self”?

Each of us gives a different answer to that. Some might say, “I’m actually a loving parent, but, at work, a loving parent has no qualities which are appropriate for work; so I wear the mask of a businessperson instead, because it’s more functional to do so.” And, in fact, a successful businessperson will make a lot of money, bring that home, and enable their family to prosper better — reinforcing the idea that this is what a loving parent should do: provide for their family so that they have a comfortable living. There is no contradiction here.

But we can stretch the analogy further. With our friends, we might be enthusiastic soccer supporters. The qualities we develop as “loving parents” or “businesspersons” have little in common with what a soccer fan needs to have. So we adopt those qualities and characteristics as well. We don’t “stop being ourselves”; we just wear a different mask. And while we’re with the soccer-loving crowd, we might even say, “I’m truly a soccer fan; but at home I wear the mask of a loving parent, which is what society expects me to do; while at work I have to be the perfect businessperson, or I’ll be without a job”. So, according to necessity, location, environment, and crowd, we just wear different masks.

Some might realize this and say, “during all my life, I just wear different masks, depending on the situation”. A loving parent might get angry — for good reasons, when a kid is playing with a razor, with fire, or putting their fingers inside the electric plug — and suddenly displaying a different mask, one which is more appropriate to deal with that situation. But they don’t “stop” being loving parents. In fact, it’s because they’re loving parents that they wish to protect their children, and, as such, sometimes a different “mask” is required.

The question, of course, is what happens if you discard all masks. What is left?

Now most people worry little about that. They consider the exercise intellectually unchallenging; they just assume that, “deep down there”, in whatever area of the brain that science fashionable decides, there is an unchanging self, somewhere, quite hidden from everything, and that’s the “true self” that decides to wear whatever mask is appropriate. Just because we’re not neurologists or psychiatrists and cannot pinpoint the exact spot of where that unchanging self resides, that doesn’t mean it doesn’t exist. When we open the window and look towards the horizon, we don’t see Australia (unless, of course, you happen to be there), but just because we cannot see it, it doesn’t mean that Australia doesn’t exist. Right?

All this gets questioned when we discover that we’re crossdressers. Where does this come from?

Current science is unable to give a precise answer, even though there are hints that the blood barrier that separates the brain from the rest of the body had misbehaved while we were inside our mother’s womb. For some reason, if we’re MtF transgendered people, the hormones that triggered masculinization in the whole body did a bad job with the brain. Depending on how bad the job has been, we might have a “female brain” but a male body. There seems to be some evidence that this is not only possible, but not that rare, even though it’s the subject of a lot of speculation.

Whatever the reason, it seems to be clear that there are conditions that trigger these “crossdressing urges”. This shouldn’t be very surprising. You might spend the first decades of your life without a clue if you’re a loving parent or not. It’s just when you create your family and have your first kid that this situation triggers the need to consider yourself as a loving parent. People like me, who have no kids and never will have them, will never be subject to that condition, so I will spend all my life without ever thinking about myself as a loving parent. I might still think about myself as a (mostly unsuccessful) businessperson instead, since I had to deal with that situation before, and my “self” adapted to that situation.

The point here is that something triggers the crossdressing urge in us. It can be physical, biological, determined by our genes. It can lay dormant for a few years or decades. The “trigger” might just be the first time, by accident, that we wear our mom’s high heel shoe and feel pleased with the idea — or something that just happens much, much later in our life. Every one of us has a different story to tell, but we usually can pinpoint the moment in our life that triggered these urges, and we all recognize the similar sensations, feelings, and thoughts we have, even though the actual trigger might be quite different for each of us.

The point here is that while our society perfectly accepts that our first job will “trigger” the urge to become a businessperson or the first child that is born to us “triggers” the new mask of becoming a loving parent — or even that the first time we watch a soccer game “triggers” the need to become a soccer fan and behave like one — our society is not comfortable with the idea of having a male “triggering” the behaviour of a woman, be it merely by wearing their clothes, adopting a woman’s role, or even becoming a woman physically. This is outside “expected” behaviour and seen as an anomaly — just because the majority of people, in similar situations, never experience that “trigger”. Putting it in perspective: two brothers might play one day with their mom’s high heels, one of them feels the trigger that says, “this is fun, this is comfortable, this gives me pleasure”, while the other is completely indifferent. So it’s not the high heels by themselves that are the “reason” for the crossdressing. This is actually well established — young boys playing with dolls do not automatically become transgendered or homossexual; and, vice-versa, girls playing with cars and soldiers don’t automatically become car mechanics or Marines. While this certainly happens in a few cases, it’s not that clear-cut. It’s certainly true, however, that social conditioning plays a role in defining how we think about ourselves. Sometimes it’s the rejection of that role that will define us. A typical example: in a very open-minded family, girls and boys might be encouraged to play with the same toys and wear the same clothes, and do the same house chores. Some might reject this, much later, and become homophobic or transphobic; others, by unknown reasons, might “trigger” a latent transgenderity (or homossexuality) which will develop later. But the point is that the vast majority will never be affected at all. They simply don’t react to those triggers.

Where I’m leading at is that we might actually attribute the “reason” for our transgenderity to specific things that happened to us in our past, or even to our genetic makeup, but that’s not the real “reason” — it was just a trigger and nothing else. The potential for revealing the transgenderity was always there, even without the trigger; it’s just the trigger that makes us face it. And then several things can happen: rejection, which is quite common; frustration or depression, because we now realize we’re a different person than we thought; or an immense sense of relief that things, after all, are “right” this way. Whatever happens, the lesson we all have to learn is that we don’t have a “self” built-in into our genes, neurons, or whatever dualist philosophy tells us where the “self” is. We just create our own selves based on the interaction we have with others, the environment — and the interaction with our own thoughts. So we create a “female self” (if we’re MtF transgendered), like we “create” the mask of a loving parent, a businessperson, or a soccer fan. The difference is mostly that the latter are often socially and educationally conditioned — established roles that work as archetypes in our society — while mentally switching gender is not universally accepted and there are no established archetypes for that. It’s something we decide to do on our own.

I’m not saying that “it’s all in our imagination”. Fortunately, science shows us that this is not the case. As said, the majority of people, when in the presence of a certain trigger, will not suddenly become transgendered. There has to be something pre-existing in us that will allow the trigger to have any effect in us. As said, the current theories think that it can be the way our transgendered brains are wired before we’re even born; we might get better theories in the future, as research develops. Whatever the real reason is, it’s pointless to fret much about the cause. We can only accept that, under certain conditions, our transgenderity is triggered and reveals itself to us. And, as such, we have just to deal with it, like we deal with everything else that happens in our life (our first job; our first family; our first soccer game), and create our own self-image that turns the crossdressing/transgender experience comfortable to us.

Recognizing that there is “nothing wrong” in “switching masks” — because that’s what we do all day long — and that the “self” is nothing “written in stone”, but something that evolves over time anyway (no matter what we do, we cannot “feel” or “think” like we did in our teens — we can just evoke the memories we had), no matter what we do. Or, rather, it evolves because of things that we do. And that just reinforces the way we think about ourselves and what, exactly, this “self” is.

It takes some time to accept it. For me, I think that deep down I never liked to wear the mask of a male guy — it’s incredibly boring to be male. The mask of a female is much more comforting, exciting, and pleasurable. So I’m much more happier defining my self as being female than male, because I have developed aversion of all that makes me male, while I just find pleasurable things in all that makes me female. Naturally enough, I develop an affinity towards anything female, and reject whatever is male. In a sense, this is not much different from someone who feels an affinity of being a loving parent and utterly reject the idea of being a ruthless, cold, angry parent who has no respect for their family.

Naturally enough, the more I reinforce this idea of finding the “female mask” much more interesting and pleasurable than the “male mask”, I “become” more and more attracted to the female side, and reject the male side more and more. This is only natural. We get better and better with training, and I’m training to become more female, because it’s the kind of training that I find very agreeable and pleasurable — while all my training as a male was mostly boring, uninteresting, and, to a degree, painful and frustrating. Not everybody thinks like that, of course. Some enjoy both masks — both facets of one’s self — to the same degree. That shouldn’t be so surprising — it’s like someone who enjoys as much being a businessperson as a soccer fan, and sees no conflict between both (I know of a famous banker in my country who thinks exactly like that!).

Now I’m sure that many MtF transsexuals will utterly disagree with me, because they’re so sure that they’re female that the idea of wearing a “male mask” is utterly alien and abhorrent to them. But we’re talking about the same thing, really. In their case, the issue is that the trigger happened very early, and with an intensity that I have never felt, to the point of becoming overwhelming. Because our society is so strongly split between the male/female duality, with little or no overlap, it’s not surprising that the urge to become part of the opposite pole in that duality becomes incredibly strong. I have this strange theory that in a world where there was no duality between the gender roles, clothing, etc. there wouldn’t be any crossdressers or perhaps not even transgendered/transexual people. But I digress.

So, the issue here is that “becoming female” — temporarily or permanently — should not be viewed as something so strange. We’re constantly reinventing our own selves; we do that all the time, even though we give little thought to it. We adapt the way we interact with others depending on the situation. Our experience, education, and interaction shapes us and who we are. While at every moment we have this idea that there is an “inner self” — and the rest are just masks we wear on occasion — the truth is that this inner self is changing all the time. Thus, it shouldn’t be so odd that we change from a male to a female self depending on the clothes we wear; we change our “selves” all the time, when we discard the pyjamas and wear business attire, or drop the suit to wear a soccer fan T-shirt. What is this “inner self” except the will to adopt a particular mask depending on the occasion?

Granted, we favour some masks over the others. And this is where our difference lies: for us, wearing a female mask, even though we’re physically born as males, is as natural (or even more natural) than wearing a business person mask, a loving parent mask, a soccer fan mask. Due to social constraints, this particular mask is not viewed as acceptable (while the others are), but that’s just a social convention. But because we’re so well moulded to fit specific social norms and conventions, we even think of ourselves as being a bit “odd” (not to mention how others view us). That should not really bother us much — masks are just masks, we shouldn’t give so much importance to them, and just wear the masks we’re more comfortable with.

Why isn’t crossdressing an addiction?

Now this topic actually popped up in a discussion with my wife, and, by some strange coincidence, I had been reading about this the week before the vacations. The argument is simple (and we’ll see how it’s flawed): assuming that crossdressing is not a mental disease, then the behaviour of a crossdresser follows the same patterns as an addiction. Consider the following points: we dress because it gives us pleasure. We get adrenaline rushes or orgasms from crossdressing. Seeking pleasure in an obsessive way is a typical hallmark of all addictions. The more we crossdress, the more familiar we are with it, but we need more and more crossdressing to continue to sustain the same levels of pleasure (when tied to the adrenaline rush, of course). This makes us adopt more risky behaviour: from hiding everything in the closet, we “come out” to our beloved ones, we start to crossdress for whole hours at a stretch, we start going out, first by night, then we go to LGBT-friendly spots, then we go out by day, then we even start going to “normal” (i.e. non-LGBT-friendly) places. Then we start changing our bodies and finally we go all the way through surgery, discarding our previous lives, and become full-time women. All these steps trigger the adrenaline rush from going a step further, but once the step is taken, it becomes familiar; when it becomes familiar, it’s not so “exciting” as before, and we need to go further and further in our risk exposure.

Addictions are not only about illegal drug consumption. Parashooting, bungee-jumping, gambling, or any kind of radical sport is all about the adrenaline rush, and they can become addictions as well. Sure, adrenaline is a natural substance and not necessarily a harmful one (its effects don’t last long and the body replenishes the spent adrenaline naturally), but the obsession with the adrenaline rush can become addictive. Similarly, for crossdressers who get orgasmic pleasure while dressing, while obviously feeling and enjoying an orgasm is as natural as feeling an adrenaline rush, the constant obsession with orgasmic pleasure can become addictive as well — there are plenty of sex addicts around. And for some it’s a combination of both things — adrenaline plus orgasm — and it can even be intellectually stimulating. What turns something into an addiction is the constant craving, the obsession, the whole focus placed on the object of desire, and the issue that you need more, push harder, go further away from the zone of comfort, to get the same level of stimulation. When this kind of obsession starts to have a negative effect on our lives — when we forget about loved ones, when we overspend to indulge in the obsessive behaviour, when we get seriously depressed due to the constant craving that never gets away — then all these constitute a form of addiction.

This is pretty much what it looks like to an outsider. And, naturally enough, when this gets exposed, what do we do? We deny it. Just like any addict: they will never believe that they have “lost control”, even though all their behaviour shows otherwise. We cannot think of ourselves as “an addict” so we will justify our behaviour with all sorts of excuses. And some will be familiar to you: “I cannot do anything about crossdressing”, “crossdressing cannot be ‘wished away’, it’s something I’ve been born with”, “medical science says that you cannot ‘cure’ crossdressing”, and so forth. Even the attempts to “purge” all clothes and accessories — which we later buy again — is typical of certain addictions: misguided attempts to “do something” about it but which will always fail.

So is my wife right?

Fortunately, we have almost half a century of research in this area which helps us to shed some light on the subject. And the first thing is that we do not become crossdressers because we want to, but because we have been born with the latent potential of revealing ourselves as crossdressers (and for most of us all we need is a trigger). In fact, the mechanism is pretty much the same as the one that conditions our social role. A woman’s brain is genetically modified to act and think in a certain way, but it’s just when it’s exposed to education, society, and introduced to social roles, that a woman starts to act and behave like a woman. Putting it into other words, female babies aren’t born wearing lipstick and heels; they have to learn how to do these things. But on the other hand, even groups of females and males in complete isolation from society will develop different roles among the genders, without being taught to do so. Why? Because the potential for difference is there — for example, due to physical differences, it’s easier for males to hunt and protect the family with the strength of their muscles. While individuals differ — there can certainly be females stronger than some males — in general, the different genetic makeup of males and females will lead to different roles in society.

Thus, it is stupid to say that females are “addicted to female things”. Some may well be — like the famous example of Imelda Marcos and her obsession with shoes — but, in general, and on average, people are not “addicted” to their ways of life. Transgendered people, similarly, due to whatever causes transgenderity, feel a strong attachment to certain roles which they’re more comfortable with, and while this can eventually lead to what seems, from the outside, to be obsessive behaviour, it’s still not an addiction.

Whereas there is no scientific basis for believing that gambling addicts or drug addicts are somehow physically predisposed to become addicts. They might be psychologically predisposed to do so — and the environment they live in, and the education they’ve received (or the rejection of that education and environment — might trigger the addiction. But it’s a completely different phenomenon, at least at the light of what we know today about transgenderity and addiction.

This is also one of the (many) reasons why you may be able to “cure” several types of addictions — because there are psychological factors for the addiction — but you cannot “cure” homosexuality or transgenderity. The best you can do is helping people to accept their condition, and, as such, not suffer due to anxiety, frustration, or depression.

Obviously this is the kind of fine dividing line which is very hard to argue without a profound understanding of the issues and a thorough knowledge of what people think and feel. And the reason for that is that abnormal behaviour — in the sense that it is not exhibited by the majority of people — is hard to understand and accept by that majority. If an external behaviour looks like the compulsory and obsessive behaviour of an addicted, then it surely “must” be addiction (“if it walks like a duck and quacks like a duck, it must be a duck”). But things are not so obvious like they seem to be. And this is a problem that we crossdressers and transgendered individuals have to face.

I’m not so bold as I thought… specially because women are not meant to be so bold

Now this was an interesting experience that revealed a lot about myself, and one which had a surprising result.

Crossdressers fear being recognized as such — becoming the source not only of laughter (from strangers) but even things that may affect their lives. Being seen in women’s clothing by one of our employers might cost us the job; being seen by neighbours might lead to a lot of problems at home, as they start to shun you and even convey the idea that you’re not welcome any longer. These, however, are fears that can slowly be overcome — being more careful, dressing away from home/workplace, picking hours where nobody is around, and so forth. Dealing with laughter and scorn might take some time getting used to, but eventually you’ll get there as well. In my case, the way I learned to deal with that was by shaving most of my body hair away. I started doing this during the winter, when nobody noticed; when I also did it in the summer, of course I was scorned and laughed at by family members and friends. So what? I just smiled back and continued to do so — I didn’t even justify it besides saying “I do it because I like it; if it bothers you, you don’t need to watch 🙂 ” After a few years doing that, most of the people who know me pretty much ignore my lack of body hair. Occasionally they still tease me about it, but they see that I’m utterly unaffected by what they might say (no matter how reasonable it often is!).

So, while on my short vacations, I expected to be pretty much immune to both these things. Nobody from my circle of friends, family, and acquaintances would be around — no need to worry about that. And if I needed to interact with others, and get laughed at, so what? I’m now used to it. So I could enjoy my crossdressing fully.

There was, however, a catch, which I didn’t quite foresee, even though I should have been able to look at the tell-tale signs: I’m afraid of males in the middle of the night, specially in small groups, but even isolated individuals scare me.

It’s reasonable to ask “why?”

Let’s put things in perspective. Except for some “darker” areas, most of Portugal has relatively little crime, compared to, say, São Paulo in Brazil or Los Angeles in the US. This means that there is a certain amount of safety, even in the middle of the night. On the other hand, as a male, I’m 1.78m tall, which is pretty much the average. I’m not too old, and definitely not skinny, and, of course, except during high summer, when I wear T-shirts, the lack of body muscles does not show. What this means is that as a potential target for muggers I’m definitely low-risk; I don’t even look rich, any common robber will see that all my clothes are a decade old. Obviously this never stopped gangs from stopping people in the streets, but let’s be honest here — I’m not the “typical” victim. They’re far better off by picking someone else; they would need to be very desperate to select me as a victim.

Obviously, when I walk around in the middle of the night as a male, I also don’t pick any fights, nor attract attention, or that I’m careless. I remain inconspicuous and fade into the background, but without any kind of fear. I just project this “don’t bother with me, because I don’t bother with you” attitude. Just a regular, normal guy, who is probably too poor to be worth the risk anyway — specially when they see the wreck I drive.

Now all this changes when I’m crossdressed.

I still am 1.78m tall — or taller, in my heels. I’m still not skinny, nor look too old. And, in fact, I even look like a male. So, in theory, I should be “as safe” wearing women’s clothes as when I wear male ones. Right? I’m still the same person, of course.

Well, the devil is in the details, as the saying goes. First, it’s impossible to be inconspicuous, as my wife so well pointed out to me. I cannot avoid attracting attention, even if I do an effort to do so — there is simply no way that a big-framed, tall redhead is able to walk around without turning a few heads. Specially, of course, when it turns out that this redhead is not really a female.

So during my vacations I had to face this new dilemma: I do, in fact, attract attention, but for the completely wrong reasons. Instead of fading into the background, I stand out. Instead of being ignored by passers-by, I get people to come out of bars and their houses and watch me with a defiant look. And the more rowdy and mean-looking they are, the more likely they are to stop in their tracks, turn to me, and, in some cases, step purposefully towards me.

Now women — specially women walking alone in the middle of the night — are obviously used to that kind of unwanted attention, and have learned to cope with that (for example, by not going out alone, but walk in groups, specially groups containing a few males). I’m not used to that. I’m not even used to “fear” people when I’m on the street by myself. This is a novel experience to me — the idea that, as a female, I’m weak, I’m a target, I attract attention which I don’t want, and have to cope with it. Namely, by turning back to the car and walk away. It’s not exactly something which I consider fun. Well, there is this fun aspect of “feeling fear from male strangers with evil intentions, just like a woman”. It means that I’m dealing with a new aspect of “walking like a female” — it means I’m now subject to the same threats as genetic women are. Worse than that: since it’s easy to spot that I’m not female, this can trigger a strong transphobic streak in some types. Not all will simply stop and laugh. Rather, by feeling “cheated”, they might become furious — furious at themselves for “feeling” something towards this redhead in heels, furious with me for “cheating” them, making them believe that I’m a woman when clearly I’m not, and then furious in general against all kinds of freaks who pass as women. This might make them become violent and aggressive, while in different circumstances — e.g. when watching a genetic female walking by — they might just make a joke, whistle, or simply observe with a smile but basically do nothing. Getting a crossdresser instead might switch their mood to a more violent one. I simply have no idea what to expect.

Well, in a sense, I suppose this “comes with the package”: if I wish to look and behave like a girl, I will also have to suffer the consequences of doing so. This also recalls something else that my wife is always saying, and which I also have read elsewhere from fellow crossdresser blogs. As a crossdresser, I exaggerate all positive and pleasurable attributes of women (or at least of looking like one), while at the same time ignoring all negative aspects of being a woman — and thinking that the negative aspects of being a male far outweigh them. It’s these kinds of experiences that put things in perspective. Yes, dressing, walking, feeling like a woman is great, there is no question about it, but there is a bad side to it. Women are weak, they’re easy targets, they’re prey to the more rowdy types, and they’re not so bold about it — they run away first in order to talk later about it, and will only fight when cornered (just like cats!). So perhaps this was good for my bloated ego and excessive self-confidence. After all, I have picked a new female trait which I didn’t even mean to get: now I’m not so bold as I thought I would be.

And of course this will limit my excitement and enjoyment of going out on my own. Just like any other girl, in fact.


Another lesson learned — or, rather, confirmed — is that there is nothing to “fear” from business interactions. On my previous post I talked about how I engaged gas station attendants, bar owners, and even a hotel attendant doubling as security. In all those cases the interaction went smoothly. Obviously I was “read” — even on a dark night with little lighting (and it wasn’t quite the case, all those places were well lit), there is still my voice that will betray me. Even though, as said, I can pretty much sound very different from my usual deep bass, and do that effortlessly. I will still not sound very female-ish — just different.

All transgendered people need voice lessons during transition, because voice is the kind of thing that hormones and surgery will not change. You can “shave” the Adam’s Apple, and even stretch the vocal cords with surgery, but that’s not enough: you will still learn to “speak like a woman”, or as closely possible as you can, using techniques like the ones presented by candiFLA. The important thing here to understand is that no kind of falsetto will ever sound right; it’s good for TV comedies, but not for passing. Instead, one should realize that males actually have a huge advantage in terms of voice over females. What makes the male voice “deep” is mostly resonance from many harmonics; this comes from having the sound of one’s voice resonate in the chest, the tummy, the head, nose, and so forth, all together — but mostly from the chest. We might not grow boobs, but we grow large chests, with plenty of space for all those harmonics to resonate. So turning one’s male voice into a more feminine one is simple (in theory): stop letting your voice resonate in the chest. Just use the head for that. It’s a much, much smaller space, and, as such, there will be far fewer harmonics resonating. Sure, it will sound more metallic; but it will also sound “less male”. It might sound more feminine (like candiFLA does!). Then you can add a lot of tricks — like inflection, and the sing-song pronunciation which all women pick naturally, as well as the choice of words, the more precise pronunciation, and so forth — to improve on that. The result can be quite passable. And there is nothing wrong with a husky voice, which is considered to be very sexy; you don’t need to sound like a 16-year-old Valley Girl with permanent hysterics just to “pass”!

While it’s quite obvious that I’m light-years away from any transgendered girl like candiFLA, the best I can say about my own voice training is that probably most people wouldn’t recognize my voice as being “mine”. Most would be pretty sure it belongs to a guy. A very few might have some doubts.

However, common to all my interactions so far, it seems that people doing business simply don’t care. They just want to make a sale. It helps to be polite, of course, but I never felt any negativity or even reticence — all these people just wanted to make sure I got the best service for my money. I even noticed that they didn’t pay attention to my cleavage 🙂 They looked me in the eyes, smiled, remained polite all the way through, and treated me exactly as any other customer. That was an amazing experience, and one that continues to reinforce my idea that the future of fighting transphobia is simply to shop!

Naturally, this has built up my confidence. Granted, the place where I was most at ease was at the Heaven Club, since it’s a LGBT-friendly spot — I wasn’t expecting anything else, obviously. I might have enjoyed a nice chat, but that was asking too much for a nightclub playing loud music, even though I was the only customer there. But the gas attendants were perfectly professional all the way through, and I’m sure that they don’t have that many crossdressers around.

Or maybe this was just a local experience. As said, the Algarve is used to all kinds of people; they might be more willing to deal with crossdressers and transgendered people over there, since it’s a highly-developed tourist destination, and so long you’re willing to spend money there and not disturbe the peace, they couldn’t care less about how you look or what kind of things you enjoy to wear. There is only one way of testing this out: going out in the Lisbon area and see if my experience is similar!

No outfit looks good on me!

On my return, when packing things back to where they usually are in the closet, I found some ancient pictures of myself, from the earliest crossdressing attempts. I always wondered where I had placed them! These are still analogue pictures, probably from around 1997 or so, some of which (but not all!) had been scanned by a crossdressing friend I used to chat with (since I had no access to a scanner back then). Well, I had lost most of those early scans, so I thought it would be nice to scan them again and put them up on the historical section somewhere…

But I quickly realized none of the pictures were worthy of being published. Why? Well, because these were from my earliest attempts to do full crossdressing with clothes and accessories I had bought at that time, hoping they would suit me. They didn’t, but I had no idea of that at the time. The only two things I kept from those days are a pair of high heel stilettos, which I still use occasionally, and one of the cigarette holders which I had bought at the time (I already owned two or three — as mentioned before, I’ve been a regular holder user since my late teens, even when not being dressed).

But all else was wrong. The makeup was horrible. One of the wigs looked like something out of a horror movie; the other wig, even though it’s made of human hair (I still have it!), didn’t look realistic enough. While those days I stuck mostly to black dresses, they all looked like they came of a B series movie from the 1950s. I actually looked much older in 1997 than I do now!

You might say that I’m just too critical of myself. That’s true — most “serious” crossdressers are. If all you need is the thrill of wearing female clothes because it turns you on, then probably you won’t care about what you’re actually wearing, so long as it’s designed to be worn by a woman. But if you’re like me, you’re after the ultimate female image: the one allowing you to pass.

It’s true that if you’re thin and tall and have the perfect oval face with full lips and large eyes, you can wear anything — and you’re also probably a supermodel 🙂 For the rest of the universe, no matter what your genes say, you will need to figure out what looks good on you and what doesn’t. Well, here is where things start to become complicated. I remember that when I showed my old outfits to my wife for the first time, she just said that they were “too old” for me. And she was right. She then proceeded — for the first and last time — to pick some new clothes for me. Unfortunately, even though she has a reasonably good taste in clothing, her choices didn’t benefit me much. It shouldn’t be very surprising: after all, she’s small and was rather chubby back then (these days, due to her many chronic illnesses, she has lost a lot of weight), and has a completely different skin complexion and hair colour than me. Her choices didn’t “fit” me that well.

So I had to experiment further. The truth is, I cannot “experiment” that much. For the time being, I don’t go crossdressed into department stores; I just browse through their aisles in “male mode”, looking for things that I think that will look good on me. Almost always they don’t. Even a few exceptions, after wearing them once or twice, are simply wrong. Why exactly that happens in so many cases is still a mystery for me — even after reading a lot about the do’s and don’ts of certain styles, colours, and so forth. Some things make me look much older, even though I thought they would look good on women of my age. Some make me look trashy, when I was aiming for something sexy. Some make me look sloppy, even though I was buying casual clothing. And even the few elegant outfit I have… one makes me look 65, the other seems to point a huge blinking arrow with a neon sign saying “Crossdresser!” to me, and, well, the last one is sort of passable, but will never make me “pass” (pun intended).

There are a few lessons I have learned the hard way. While there are exceptions, the more costly the item, the more likely it fits better and looks great on me. This is a problem, since I cannot afford many costly items — right now, I cannot afford any items at all, costly or not! — and so I tend to buy more cheap ones: the idea being that if they’re very cheap, at least I will not worry much about giving them away if I cannot use them. But it’s still a bit frustrating!

Frustrating, yes, but not unsurprising. Since I never cared much about male clothes, I never really worried about buying them. In fact, to the best of my knowledge, I just remember buying a couple of suits and a raincoat on my own — 15 years ago. All the rest have been gifts from family & friends. Yup, I’m not exaggerating. I don’t even buy shorts or socks for me; someone will surely give them to me as presents for Christmas or birthday. I have no “personal style”, nor a “look”, and never had any intention of being “fashionable”. So I hardly understand anything about what brands are popular this year, what colour one is supposed to wear, what styles are appropriate for my shape, what makes me look younger or older. These are all a mystery to me. Or, rather, they’re filed as “unnecessary knowledge” — it’s like car mechanics: I don’t understand how cars work, I just drive them. With clothes, I just get people to offer me whatever they think I might like. And on my side of things, I’m glad that someone has taken away the burden of choice for me, so I’ll wear pretty much whatever I’m given. The only exception was my love for neck scarves, which gave me a British look that I enjoyed, but my wife was absolutely against the scarves, so I had to give them all away. I still keep a handful of ties around, but, since I started to work from home, and hardly ever meet with clients, I don’t wear them. In fact, I enjoy being a “veteran computer geek”. You don’t expect geeks in Italian suits, Spanish shoes and British ties; I can get along with a semi-casual style made out of decade-old shirts, serviceable jeans and a jacket. People in my country are far less stiff and conservative in their choice of clothes, anyway (although I had to learn that “casual” is also a fashion style which has its own rules!).

So when starting to delve into the wonderful world of female clothing, it was an incredible experience. Now suddenly fashion mattered. Now I had to combine colours — something tough to do, when you can only recognize 16 different shades of colour, while genetic women are able to distinguish between thousands (how do you distinguish “salmon” from “pale coral”? Why are “tangerine” and “orange” two completely different shades? Is “peach” pinkish or orange-ish? Is “maroon” a lighter shade of “chocolate”? I know that “crimson red” is not the same as “brick red”, but between them is there really some shade that I’d call “red”? My wife has two raincoats with the same cut, one is apple green, the other is, well, red. She constantly refers to them as “lemon yellow” and “pink”. Uh?)

But also now I discovered that my body has a “shape”, too, and that women’s clothes have different cuts depending on the “shape”. So, no straps for me; I don’t have the shoulders for that. Since I’ve got a large chest, I cannot wear round or square necklines; surprisingly, I’m supposed to wear V-cuts (which I would expect that they would reveal too much, but apparently, if you’re big-breasted, you’re supposed to show off some cleavage; the other styles of necklines are to disguise that you have nothing to show!). I’m not straight-lined, but curvy (with all that padding), so I should avoid straight cuts — but focus on anything that gives me a waistline instead. Which is becoming hard: casual clothing, and even some elegant clothing, these days seem to be designed for the heavily overweight types and/or pregnant women, by putting the waistline just below the breastline, which looks terrible on me. Most tops and sweaters are meant to be worn over a pair of tight jeans, and not inside skirts. But most of them, even if they don’t have a straight cut, do not favour the waistline much (because most thick sweaters are used to disguise overweight women!); so I’m always wearing a belt with them. There are a few exceptions, and as I mentioned once, I had to let someone cut a dress for me so that it looked right (and afterwards it did!). I cannot wear ruffled or laced blouses; they’re meant for women with small breasts. Similarly, long necklaces (of which I have a dozen!) are a no-no if you have “projecting” breasts; I can, at most, wear very short necklaces. Ugh! So much to learn!

Then come accessories, something that males don’t worry about: a guy’s only accessory is the watch and possibly the glasses, and you buy them once and cannot match them with anything else anyway. Women, by contrast, have a lot to match. You don’t wear pearls during the day; you avoid golden things, but, even worse, you avoid mixing golden with silvery/metallic things. Colour matching is out of fashion; gone are the days that you would wear green eye makeup to match a green dress and wear emeralds. But, on the other hand, colour extremes are out of fashion as well: if you’re wearing red, you’re not going to wear a green (not even a blue!) belt with that, nor jewelry of any colour… except probably white or metallic. Then again, there are fashionistas saying that “everything is allowed”. Sure, but not “everything” will look good on me! In fact, nothing seems to work well enough!

Oh, I know I’m exaggerating. A few things actually work out. They don’t make me feel neither too old, neither too young, neither too slutty, neither too casual, neither too casual. They don’t look too good either — just average and uninteresting. But strangely enough, these are the things that seem to work best. Maybe I’m just an average and uninteresting person!

At the end of the day, ironically, no matter what I’m wearing underneath, I tend to be happy that I’m wearing a black overcoat on top of everything! But I can only wear that in the winter. And if it’s too cold and I’m in an elegant mood, I wear a faux fur coat — which is too short, and, because it has a straight cut, makes me look much fatter. Gah!

No wonder that the few extremely good-looking crossdressers I know have either a) a perfect body; or b) an extraordinary amount of clothes in their wardrobes. No small wonder! They have to buy hundreds of outfits to get a few dozens that actually work for them. I would need to do the same… if my wife allowed me, of course, which she doesn’t. But I slowly start accepting that she’s right. What’s the point of wasting so much money on things that will never fit me right, even if they are supposed to be the “right” styles and cuts for my age and body?

I know, you’ll say that I look good on a lot of things on the pictures and videos. Well, yes and no. I really cheat a lot. Except for some, I use the best angles and cut off the bits that don’t look so good. That’s why sometimes I don’t bother to stand up when doing a video; I know that I look reasonably well from the breastline upwards, but not below that. And sometimes not even that. And, of course, sometimes I don’t care and do the video or the picture anyway. But the point is, I brood a lot over those things, and a thing that comes to mind is that if I ever start to go out regularly with some friends, I would be stumped at what to wear after a few sessions — I’ll quickly exhaust the amount of outfits that have a minimal chance of looking acceptable, while they all look like they have hired Stacy London or  Rachel Zoe for advice. Better still, some of them look like they’re managing the fashion school where Stacy and Rachel graduated!

How far can I go with body changes?

I have a few gurrlfriends who have perfect bodies. Sometimes, on the rare occasions I’m able to dress, I come online on the webcam, and they say, “oooh you’re dressed today! Let me get dressed too! It just takes me 20 minutes!” And so it is. Well, sometimes it’s half an hour. They just slip into a dress, get their latest wig into shape, do some minimalistic makeup — mascara and some lipstick — and there they are, a few minutes later, looking at their best, just like any other pretty woman.

My own routine takes, well, the better part of three hours.

I’m not saying I’m not enjoying myself for those three hours; in fact, I do enjoy them very much, in spite of the very skeptical comments of my wife. She says I’m insane for taking so much time; if I lived full-time as a woman, I would never be able to spend so much time in the bathroom every day.

Well, she’s partially right. Three hours is really too much. But as a male, I tend to spend over an hour to get ready in the morning anyway, and the actual showering just takes 3-5 minutes, and I don’t even shave every day.

As a crossdresser it takes far, far longer. First comes the whole routine of getting rid of unwanted hair — on the face and on the body. This takes ages — more precisely, perhaps around 40 minutes or so, if I’m using a razor. For many years I tended to use an epilator on most of the body, but that took me five hours, and I cannot use it on the face anyway (the advantage, of course, is that it keeps the hair from growing for about two weeks, sometimes even a bit more, and you just need some regular maintenance afterwards). The face is shaven with four passes, specially if I hadn’t shaved on the previous day: once downwards (in the direction of growth), once upwards (against the direction of growth), once from the back to the front/chin, and once in the diagonal (yes, I have face hair growing in all possible ways). Just that takes eons. But the rest of the body has a much larger surface than the face, so it also takes quite a while.

Then, while I wait for the face skin to absorb the moisturizer, I put on the lowest layer of clothing — padding. If I’m in the mood of creating some cleavage, this takes far longer than a sane people would think. In fact, after having worn everything I will wear that day, a good half hour might have elapsed.

The next step is the foundation. To hide the beard shadow, I still use the old lipstick trick. A CD friend of mine found out a shop in Lisbon that sells these professional television/movie makeup, which include foundation sticks for covering the beard shadow, but, no matter how good these are, they all share the same issue: they demand that I wait a bit until it dries, before starting on the foundation. I usually have a cigarette while I wait and start brushing the wig into shape, or do some manicure (but don’t actually paint the nails, because they almost invariably will not dry in time, and get ruined — and ruin bits of whatever I’m wearing).

Foundation comes next, eventually with some highlighting before, and then there is more time to wait until that dries. Another cigarette, another go at the wig, or maybe I’ll be choosing the accessories. Over one and a half hours have elapsed since I started.

Then comes the more fun part of applying makeup. Everybody has a different routine, and I cannot say what’s “best”, since I’ve experimented with some variants, and they all seem to work similarly well. I usually start with the lips, because your face will immediately change to something clearly feminine, and that helps to set the mood. Next comes the white highlighting, on the eye corners, on the nose (to make it look slightly thinner), on the cheekbones, and here and there on special eyes. Some corrector to get rid of some spots, and, since these days I’m chronically with fatigue rings, these get some “treatment” as well.

Next comes eyeliner, either in pencil or liquid, depending on the mood. Liquid eyeliner does an awesome job if you have a steady hand; the second best choice, for me, is kohl. This can get tricky as one aims for symmetry, but, of course, that’s hard, and requires lots of tiny corrections until it’s acceptable.

Then, in my case, I apply the blush. Why? I will need to tone it down over the cheekbones, to blend everything together, and if I let the highlights “set” for too long, this will not work well. I used to do a different routine — the blush came at a later stage! — but since I’ve got some compliments from my own wife on the tricks done with the white highlighting on the eyes, I do that first.

After looking all “blushy” 🙂 what I do next is the actual eye makeup. I don’t truly have many special techniques and tricks. “Smokey” eyes are not particularly hard to do, although they tend to look too dramatic on me (but I do them sometimes). I used to do just two colours at most, but since having bought a pack with some 40 colours or so, I rarely use less than four 🙂 It’s more fun that way, and you can experiment to see what blends well and gives some unexpected results. I’m rather fond of yellow highlights. Bronze seems to work admirably well, too; my natural skin colour on the eyes has already a lot of bronze in it (yes, again, due to lack of sleep…). If the rest of my outfit is pink/peach, then I tend to use those shades on the eye makeup as well, and they don’t look too bad. I love the lilac/purple tones, but often I get wild with them 🙂 Blue is a bit “dangerous” — my own eyes are blue/green, and this means that either of these colours will enhance the eye colour so much, that it becomes overwhelming — and boring! — but sometimes I play with blue as well; emerald green seems to be easier to play with, though. And sometimes I just use completely illogical shades, like starting with yellow, go to green, finish with purple, and add a smattering of brown and bronze here and there. Sometimes it works, sometimes it becomes undetectable (which, in a sense, is also a good thing!).

Mascara (first application) comes next, then powder to set the foundation. I know that the modern girls have no patience with powder, and just buy foundation with powder to save time. Well, that’s ok if you’re not using blush and highlights; otherwise, I rather prefer to have some powder on top of everything to tone the colours down and make them much more natural. When that step is finished, I do the second mascara application.

This means that when my makeup is finished, the clock has been ticking for over two hours 🙂

Then comes the wig. These days, as you know, I’m using a lace front wig. While in theory I could just use it like a regular wig, I use a special tape to do the finishing touches — keeping the wig directly glued to the skin, so that the hairline looks absolutely realistic. And, believe me, it does. The pictures don’t do justice to the final look. You can be at kissing distance and not see where the wig is actually held in place. Yes, I’m not exaggerating. These days, when I see people like Jessica Who on YouTube — she is very good at makeup and even better at fashion — I always think of giving her the tip: get rid of those conventional wigs, girl. They simply never look right. It’s nothing to do with their fibre quality, it’s just that they cannot ever be so realistic than a front lace (or full lace!) wig. And for some reason, the front lace wig manufacturers are able to get much more hair fibres in them, specially on places that really make a difference. Don’t ask me why. It’s just the way they’re built, I guess. The disadvantage is that they might be much warmer to use in summer (I still don’t know), and, of course, if you’re a perfectionist, the extra time spent in taping them to the forehead will cost you some precious minutes.

Some perfume, adding the last bits of accessories, and it’s time to do the nails. Now for years I’ve used falsies, which are easy to apply, specially the ones that come with double-sided tape; just a few minutes and you’re ready. I tend to use glue, which takes a bit longer to apply, and is a mess to get rid off, but it’s the only way I can be reasonably safe, knowing they will not come off at an embarrassing moment. But lately, as you know, I prefer to do my own nails. It’s also cheaper that way: a pack of false nails might cost $10-15 and last for 3 or 4 times until they’ve got so much dried glue on them that they have to be thrown away. There are cheaper nail sets made in China, but they don’t look so realistic. By contrast, a tiny vial of nail polish of good quality might cost $4 or $5, but last a few months (since I don’t paint my fingernails so often!). Sure, there is an extra cost for the nail polish remover, but it’s still cheaper. Also, it’s not so aggressive on your nails, specially if you go the route of using glue for the false nails (you will almost always need to file them off afterwards; even though you’re actually getting rid of the dried glue, a bit of the nail itself will naturally come off that way, making them a bit thinner, and looking not so good).

But there are several disadvantages. The first is that you will need to keep your nails impeccable; and secondly, grown them longer, or you’ll spoil the fun. Figuring out how long you can grow before others notice (or before my wife forces me to cut them) is tricky. And, of course, some people have such thin and broken nails that they cannot achieve good results.

The next problem, of course, is how long it takes to paint them!

Unless you’re talented, it means a lot of practice. When I started crossdressing in the late 1990s, I tended to spend, say, the better part of an hour just on the nails. It was a nightmare — I would get nail polish everywhere except on where I wanted it to be! The cuticles are my major problem. Professional manicurists are constantly wiping the excesses off, and they have this special “pen” to do that, quickly and efficiently. It’s a bit expensive, though, so I use cotton swabs and nail polish remover, which is much cheaper, of course, but far harder to get it right, specially on the very fine detail. And ironically, in my teens, I used to paint lead toy soldiers and the like. I’m actually glad I had some patience doing that, who would have known that this skill would be so useful in my adult life!

Nevertheless, it’s still hard to get it right. I’m right-handed, so I can do my left hand in, say, a minute or two; I generally get it right on the first time, too. But doing the same on the left hand takes way longer :-/ I believe that I lose almost half an hour on both hands, and, to be honest, it looks blindingly fast compared to a couple of years ago!

So there you are. Add that all together, and it’s very hard to do the whole routine (and I’m not counting the time for the nail polish to dry!) in less than 2 1/2 hours. If things start to go wrong — and sometimes things go wrong with the padding! — I can spend well three hours on it.

What to do to reduce the time?

Depending on the day, sometimes I split the process in two. My body hair, fortunately, doesn’t grow as quickly as the beard, so I can generally get away by shaving everything but the face in the morning. That will give me half an hour less, later on. On some days, I shave the face before taking a nap and then continue the rest of the routine afterwards; that cuts the time to a bit less than two hours. So it seems that if I could get rid of the body hair permanently, I would save the better part of an hour! Clearly this is at the top of my priorities. Thankfully, these days it’s perfectly acceptable for males to laser out their body hair, face and all, so this would be a huge improvement.

The padding is a problem, though. To skip it, I’ll require extensive surgery and/or hormone therapy. And believe me, I’ve thought of many ways to deal with that. I think that if I could get the perfect waist and hips, I would be able to forfeit the corset and the hip padding, and, that way, save precious time. Since I’m not a beach person, most people would never notice the difference anyway, not even my parents, who are supposed to know me quite well 🙂 I haven’t got a huge bottom, but it’s not too bad, actually; it would just require some “adjustment”. Hips, of course, would require silicone implants; and the waist would need several techniques to make it look right. Well, it’s just all a dream and a fantasy for now, but, among all the surgery I would need, this would be the one that would be most easily disguised — specially during the winter, of course, but I’m pretty sure I wouldn’t attract undue attention during the summer, either, except if I went to the beach or to a swimming pool, which I don’t go to anyway.

But if you start with surgery, where to stop? Hormones, of course, will also redistribute body fat to the “right places” (and will thin out the body hair, as a bonus), but at this stage of my life, knowing about my relatively high blood pressure which needs medication to remain at a perfectly safe and healthy level, hormones are a high risk. Surgery is the only option.

As I’ve mentioned elsewhere, it’s also highly unlikely that I’d get any breast growth with hormones. Hormones are not a magic drug; they can only work with what you’ve got. Almost all women in my family have tiny breasts, and they’ve been born with the right hormones from the start. So it’s unlikely I’d get any substantial breast growth. Again, silicone implants would be the only choice. But that’s tricky: to keep them proportioned — and that means highlighting the curves in the rest of the body — I would need large breast implants. Sure, I know what you’re thinking: every female, genetic or otherwise, wants the largest breasts they can. In my case, however, I don’t really “want” large breasts: I want to visually trick people in thinking I have a “perfect” shape, which means a difference of about 30 cm between the waistline and the hip & breast line. Remember the magic 90-60-90 hourglass figure? Well, if your waistline is way above 60 cm, that’s fine: just compensate the other two numbers, and you’ll still be hourglass-shaped and feminine 🙂 That’s my old trick, which I accomplish with padding: the corset gets the waistline down to 85 or so, meaning I need to be 115 on the hips and 115 on the breastline. That’s why, at least from the front, I look rather curvy, even though I have a large frame.

115 cm of breastline, for my frame, means a big D cup — that’s 1.5 kg of silicone for the two breasts, to give you an idea. Now, as a crossdresser, we can decide on whatever size we wish to be. But it would be utterly impossible to disguise those huge breasts with male clothing. Well. Not quite “utterly impossible”, but almost. I have, on occasion, gone out with all my padding in the winter, with a straight-cut male overcoat on top of a loose sweater, and I can look inconspicuous. But that’s only in the deep winter; and I cannot take the coat off, so it would be impossible to be indoors.

And if I ever went that route, it would be foolish to stop there. Who wants to have a curvy, feminine body but an ugly male-looking face on top of it? So, my nose would have to shrink, and the jawline redone by a surgeon. After that, well, all that would be left for me is to go full-time as a female 🙂

Too huge a step.

What about the wig? That also takes a long time to get it right. Well, the simplest solution would be to let it grow — which my wife doesn’t allow me in any case. I would also have to forfeit the nice red colour which I’m growing fond of, but revert to my natural hair colour, which is sort of a light brown — nothing really special. Having it braided, there are tricks to give it a feminine cut without anyone noticing. In my case, however, I’m loosing hair in a typical male fashion, so it would mean either a treatment for that, hormone therapy, and/or hair implants, which are also very expensive. The result would be to save, say, 10 minutes of the whole routine. Is it worth the trouble? I don’t really think so. In fact, if I went full-time as a woman, I would simply do the same thing that Tyra Banks, Beyoncé, Oprah, Lana Del Rey, etc. all do — just get the best-quality full lace wig I could afford and glue it permanently, which any hairdresser is trained to do professionally. Very simple, and you can completely change your hairstyle every 6 months (as the wig wears out). But it’s also a bit expensive, even though probably not much more expensive than styling the hair regularly.

Doing all that would mean reducing the whole routine to do the makeup (since going full-time also means having no more worries about painting the fingernails every day!). That would be, at most, half an hour — probably less if I’d use permanent eyelash extensions or some similar technique, and had the face skin in such a condition that I could forfeit foundation and just do the eyes and lips. Half an hour sounds just about right. To give you an idea, on the days I shave, I apply six different types of creams on my body, three of them on the face. That’s already part of my daily routine. Adding a bit of makeup and some lipstick, compared to all that, is nothing.

So, ultimately, my wife is wrong. I just take three hours or so because I have the completely wrong body for a woman; and also because lots of the things I do — nail polish, wig, glueing the breastforms and creating cleavage, etc. — are temporary things which I have to do every time I crossdress. If I could get rid of everything that makes my body and face un-female, then I could skip most of the routine, and just focus on the essential things: wearing the right set of clothes and doing some minimalistic makeup. That’s what my gorgeous-looking CD friends do: they already have perfectly androgynous bodies, and all they need is a nice dress, a wig, and a bit of makeup — that’s why they just need 20-30 minutes for their routine, and they will look much better than me even taking so little time. They simply don’t need any improvement. Many of them are of the skinny type, who don’t even need breastforms to enhance their breast line — a super-pushup bra with some padding is all they need, and that takes a minute to wear.

The conclusion is that it’s all in the genes. The more androgynous you are, thanks to your genetics, the shorter the routine you need. The less androgynous you look, the more complex your routine, and it will invariably take longer, to the point where there is nothing much you can do about it, except for extensive surgery which will turn you irreversibly into a woman (or something looking much more like a woman than a man), and that means transition and changing your life.

Jessica Who, in a serious moment (she usually is just hilarious!), addresses transition and explains, very rationally, why she’s not even remotely considering that route:

That certainly made me think. There is a balance to be found. Some of us are eternally searching for that balance, and unhappy because they never seem to reach it. In my case, it looks like my own balance can only be achieved going beyond the comfort zone. But that means crossing a line from where there is no return. And all that for what? Just the ability to wear dresses that fit me perfectly and the ability to go out and pass every time? How important is that in my happiness?

These are hard and difficult questions. And I have no Ultimate Answer like Jessica Who found for herself. Instead, I just have “temporary” answers: I’m attached to my own life, to my wife, parents, friends, and a certain number of decisions made in this life that made me to be what I am. Compared to all that, the wish to pass as a woman seems to be of little importance. Worse than that — compared to losing all that, and starting from scratch, means jumping into the void of uncertainty, and I’m not so bold to do all that. Sure, the experience is interesting in itself, but there is no turning back (not easily, in any case) in case I have any regrets.

Putting into other words: I’m content with my whole life except for one tiny little detail, a gene flaw that made me male. Half the world’s population lives perfectly with that. The alternative — which is a possibility these days, even if it’s complex, painful, and expensive — is having just that tiny little detail as your whole life, forfeiting everything else. It’s a huge price to pay!

That’s why I like to think of myself as a “failed transexual”. A true transexual is just worried about that “tiny little detail” — nothing else matters. Given a choice, they have no doubts that they would throw everything away just to get the body they should have been born with. If that means losing everything else, so be it. It’s not different from an Olympic athlete: changing one’s own life just for the purpose of getting a gold medal. Training every day for that. Abandoning friends and family just in the pursuit of the gold. And labouring long, discarding everything else as unimportant to reach that goal, until they get what they want. True transexuals are like that. Of course they will try to lose as little as they can along the process — trying to get their family’s and friends’ acceptance; trying to keep their job; trying to fit into society in their new gender role — but, if all else fails, ultimately they’re ready for the Big Jump and leave all that behind.

In my case I’m clearly not that bold. I’m not ready to abandon all those things that are part of my life. I spent most of my life living to other people’s expectations, and while I tend to fail each and every time, I’m still seen as doing a huge effort to please everybody. But, in turn, that struggle defines who I am today: someone who does their best to live as everybody else wants me to live. There were a few moments of glory in my past. When I finish my PhD — for which I personally care little — there will be another moment of glory, where a lot of people will be immensely pleased with my achievements (even though I have no big expectations about what happens afterwards, at least I will have done whatever I could). So all along my life there have been these special moments that have reinforced the way others see me, and, in return, have shaped the way I am. Being so used to think and act that way, I’ve grown attached to having all that.

Except for some very minor things — like removing all my body hair — any other step towards womanhood means dropping all that. It means disappointing dozens of people, some of them — like my parents, but they’re not the only ones — having invested a lot of their time, patience, and emotions in me. It also means abandoning the meagre means of surviving on my own; even with a PhD, how many universities out there in the world are willing to hire an ugly transexual? Not to mention a computer systems and network engineer — their employees and customers would be utterly shocked. Of course there are exceptions. A lot of transexuals have survived. Again, it depends on how good their genes are: the more androgynous you are when you start your transition, the more likely you will pass so perfectly that nobody will ever notice. For the rest of us with our flawed genes, there is no hope, and there is no choice. I might get a job as an after-hours janitor at McDonald’s, and while I could certainly survive on that salary, I would be forgotten and abandoned by everyone that knows me, labeled as the ultimate failure, and stricken from their Christmas card lists and their phones’ address book.

Is that the kind of life I wish to live?

Not really.

So, for now, as a “failed transexual” I can just try to enjoy myself as a crossdresser. That’s all there is left for me. Sometimes I think that there is not much more I can do to improve my image, and something unexpected comes along — the new front lace wig has gone a long way to raise my self-esteem and confidence, for instance. I might learn new makeup techniques, or improve my vocal skills, to be able to pass a bit better. I might finally learn what kind of clothes fit me best, and avoid excessive attention, in spite of my frame and height. And I might be able to become faster and better at going through my whole routine, spending less time at it, which, in turn, would mean more time to enjoy myself as a crossdresser (and not miss so many opportunities).

And — who knows? — I might just be able to do a few tiny “improvements”. Unnoticeable while in “male mode” but going a long way to benefit my female image. Some of the simplest which I have implemented did already help a lot, like trimming the eyebrows (nobody has noticed) or growing the nails much longer (they only notice when they’re too long) and keeping little body hair around (few have noticed but I can safely shrug it off) or even painting my toenails (nobody knows except my wife… and my cat). Who knows what else I might be able to come with!

Even in this constrained path I’ve temporarily chosen for myself, there might be still some room to expand, to experiment, to have fun with, and still remain within the comfort zone, and not need to face the Big Jump. And ultimately, having fun with those experiences is a big part of what makes me crossdress.

I just need to be content with that 🙂 Jessica Who already found that; and I shall learn to do the same.