License to Dress

Picture by Joana Adriana, used with permission from the author.
Picture by Joana Adriana, used with permission from the author.

For you, crossdressing is like being passionately in love: no other experience has the same appeal, nothing else matters, your only focus is to present yourself as a woman.— My psychologist

That quote might not be exact, but it’s pretty much what my psychologist said to me on my last session with her. It somehow rings true, and I’m sure that many fellow crossdressers feel the same way, especially when they have just ‘come out’ and start dressing regularly.

In my case, I’ve been dressing for about two decades now… but not with the same intensity or regularity. My psychologist believes that I’ve repressed my urges to crossdress for way too long. There was an immense relief, a decade ago, when my wife accepted my crossdressing — and accepted this new side of me which had hitherto been unknown to her. ‘Acceptance’ is not ‘encouragement’, though; I had to wait a decade until she let me go out in public and meet my friends, some of which have waited years and years until I was finally allowed to have a drink with them or simply to go out and walk around a bit.

Once she lifted her restrictions regarding my going out, a whole new world was suddenly revealed to me.

I had a small taste of that back in 2013, when we had a short vacation in the south of Portugal, and I was allowed to dress every evening and night, and go out — alone by myself, but at least I could interact with many people I crossed on the streets, gas stations, and even in a bar. It was just an appetizer to the feast of pleasure that I’m able to enjoy nowadays with my friends. But at least it made me realize that this is truly what I want — more than that, what I crave.

That piled-up repression, all that craving for so many years (decades!), was finally released. And, according to my psychologist, this simply became overwhelming in terms of the intensity of the desire to dress and be accepted as a woman.

If you are aware of evolutionary explanations of how some parts of the brain work, you know that we have adapted some traits of our brain to new tools and new situations. A classical example is reading. We have evolved to be very good at pattern-matching with incredible detail, because that was a survival trait in the middle of the savannah, where we were supposed to locate prey very easily, but also avoid predators — while women used that ability to track berries and roots even in dense undergrowth. So our eyes are particularly well-suited to capture very precise images and feed them to the brain, already processed with some hints regarding patterns. We are really so good at pattern matching. Cats, for instance, descending from the felines who are at the top of the food pyramid, are short-sighted and are excellent at identifying ‘edges’, but only those which are moving — because that’s what a superpredator needs to figure out where their prey is. Stop moving, and felines need to track you by their sense of smell. If you have cats at home, you can see very easily how this works. If you take one small cat biscuit and drop it on the ground, the cat will never fail to catch it. But once it stops rolling, they’re not so good at figuring out where it is: they will sniff around, relying on their sense of smell to figure out where the biscuit is, and sometimes they look like they are a bit dumb, sniffing around, when the biscuit is just within their reach. We can see it clearly, even if it is a dull colour on top of a dull background. Cats are not so good at seeing that; their brains are not so optimized to deal with static objects. Ours are.

As we abandoned our hunter-gatherer roots and developed civilization, those keen pattern-matching senses embedded in our brain wiring were used for a completely different purpose: reading. When you think of a receipt written in a doctor’s calligraphy, which is barely legible — but we still can make some sense out of it! — you can appreciate how good we actually are with that pattern-matching. It’s no surprise: it’s something we had to evolve to survive, because it allowed us either to find food, or to become food for predators… so we turned a well-honed evolutionary trait into something completely different (we might not need to read in order to survive, but because we developed writing, giving an important use to an evolutionary skill we already had, we didn’t lose that ability — rather, it’s conceivable that as more and more people learn to read and write, future generations might even get better and better at it).

There is an obvious, evolutionary reason for ‘falling in love’ — which actually is an euphemism for describing intense lust and passion — because, obviously, reproduction is at the core of every living creature, and we humans are not different. Due to our ancestry as living beings on planet Earth, it’s not surprising that our strongest feelings and emotions are attached to the act of reproduction. But not all beings develop such feelings and emotions. I have read a few explanations why it is the case with humans (and at least some primates), but I’m not an expert, so read this with a pinch of salt and look it up on Wikipedia.

Most living organisms have a ‘optimal’ moment during the year when they reproduce. This has to do with certain aspects of the seasons. For instance, mammals prefer to deliver their babies when the temperatures are higher and there is less chance of rain; it’s also easier to find food in spring/summer than during the cold winter. Therefore, most organisms developed mechanisms to trigger the urge to reproduce when ‘the time is right’; we all know how dogs and cats have the season when they’re in heat, and get totally obsessed with reproduction, triggered by pheromones that will become active only when the time is right. Of course this also extends to plants and other living beings, not only animals.

Some organisms, however, might be living under very special circumstances where the temperature is right and food is abundant throughout the year. Because of that, they can reproduce at any time, and therefore they have different mechanisms to trigger the reproduction urges. Humans, of course, create their artificial habitats to have reasonably constant temperature and availability of food throughout the year; and obviously, as our civilization develops further and further, this becomes true for the majority of human beings.

As such, we really don’t require a ‘special’ season for reproducing; we can reproduce all the time. However, we cannot think only of reproduction. We also need to gather food to survive. So, as a species, we need to figure out a balance between the urge to reproduce and the urge to gather food: if we spend all the time in lust and passion, we will starve for lack of food; but if we focus all our energies in merely eating and drinking, then we fail to reproduce and our species will go extinct.

I read somewhere that this is one (possible) reason why some species develop intense feelings of lust and passion, while other don’t (they merely respond to pheromones that are released only at certain periods during the year). According to that theory, when a species is in a habitat that has little difference of temperature or rain, and food is plenty and available throughout the year, then it’s more likely that such a species can reproduce all the time, and, as a consequence, a different mechanism is required to get such a species to curb their reproduction urges while they gather food for their survival; but, at the same time, they cannot be merely gathering food and forget about reproduction. In such species, the sexual act is almost always incredibly pleasurable (but so is eating!). Obviously, it’s harder to measure the degree of pleasure shown by animals (but there are a few tricks to do that), but at least, for me, this explanation sounds about right.

Humans, however, are such complex creatures that we can use parts of the brain adapted by evolution for one thing to something completely different — like using pattern-matching developed for hunting/gathering for reading instead — and this also applies to the feelings of lust and passion. Therefore, a workaholic can derive almost erotic pleasure from being totally focused on their work. And a lot of people are fond of the phrase ‘this is as good as sex’ where ‘this’ represents some kind of activity — not related to reproduction whatsoever — which, for them, has the same intensity of feelings and emotions as the sexual activity. And, of course, we are such strange animals that we can even feel nothing in relation to sex (this is what happens with some asexual individuals, for example) and move all the emotions and feelings related to orgasmic pleasure to something entirely different (such as some kinds of fetishism).

To add to the complexity, humans are a gregarious species, and that means that we have also evolved complex skills to allow us to be co-dependent with a group to enhance our chances of survival as a species. And on top of those, of course, we also developed social norms and rules. The whole issue of gender is definitely a social construct, but it’s also anchored in evolutionary biology: we need ‘rules’ (and roles!) to get both sexes to get together and at least stay long enough to raise their children. I’m not going to explore the theories if the human species was originally monogamous or polyamorous, and honestly, I don’t really care much about what we originally were — what matters for me is the present! — but the truth is that a lot of what we do, and think that is the result of being a sophisticated intelligent species, is actually rooted quite a lot in evolutionary biology.

We commonly say that we, as intelligent beings, can ‘overcome’ our nature and go against it (like, for instance, refrain from eating — or using the toilet! — even if our bodies tell us otherwise). That’s true to a certain degree, at least regarding many things that require conscious thought. But there is a lot that is unconscious, and has been inherited from survival strategies of our ancestor species.

Lust and passion are definitely one of those things, and we develop social norms to curb our emotions. But, of course, while we can repress such urges, they will not easily ‘go away’, since they fulfill an important role in our existence — reproduction. However, we also learned to enjoy lust and passion without reproduction, just because those feelings are overwhelmingly more intense than any others. But even other positive emotions are strong enough for us to desire them: everybody, without exception — human or animal — desires pleasurable emotions and want to avoid unpleasurable ones. A healthy organism (and mind) will seek what is pleasurable and understand that pain, discomfort, sadness, fear and so forth are not ‘normal’ situations, but extraordinary ones, which we should avoid: either they are felt because the situation is dangerous for us, or because we are ill, or something similar. They are ‘warning signs’ that something is not right. By contrast, if everything is ‘all right’, then we feel pleasure.

However, our brains can easily get ‘confused’. Because the pleasure/pain areas in the brain are relatively close to each other, they can overlap and cross. A typical example is sadomasochism — a fetish which is way more popular than many people are willing to admit. While I’m definitely not qualified to describe the complex details of the contemporary BDSM culture — which builds upon some fundamental rules and their own social norms — at the simplest level it describes a state where pain being inflicted (physical or mental, as in humiliation) is experienced as pleasure.

So here is what happened in my case. Due to decade-long repression of my urges and desires, now that I’m allowed to dress and go out with friends, that triggered in me the same kind of response that usually is reserved for people fiercely and passionately in love.

You know how that feeling is: you become completely obsessed with the object of your desire. You dream of them, you daydream of them, you cannot count the minutes until you are with them. You might lose your appetite and go through sleepless nights; your concentration at school or at the workplace fades; the feelings become so intense that you can become dizzy, or get headaches, or even nausea. Once you’re with your desired one, you feel pure ecstasy — absolute bliss. Nothing else really matters; even what you two do together is less important than the act of being together. You put your love on a plinth, turn them into a god(dess), and become their most faithful worshipper. Once you are away from them, you feel down, sad, frustrated, even depressed. Nothing else seems to matter, and it’s very hard to get enthusiastic about anything — not even work, not even your favourite hobby or pastime, not even your best friends matter much any longer. They all fade out and blend into the background.

Such an obsession is rarely functional, but we all experiment it, mostly during our teens, but sometimes well into our adult lives. I’ve certainly gone through that for many decades for almost all my past girlfriends (surprisingly, I kept my emotions in check when meeting my wife-to-be; by that time, I was so tired of ‘falling in love’ and get disappointed that I sort of raised some barriers. It worked. I could look at my wife with quite different eyes and feel attracted to her at a completely different level).

What I probably wasn’t expecting to happen was to feel the same thing about crossdressing.

There is an old saying that there a recent convert to a religion is always the most fanatical. We have similar experiences when joining a group, an activity, and so forth, which is new and excites us for the sheer pleasure of novelty. You may also have noticed how young couples, when they get their first babies, become totally obsessed about baby stuff, to the point of nausea to everybody around them. The same also happens to people who adopt their first puppies or kittens. They become incredibly boring, posting videos of their animals all over the social media, and cannot talk about anything else. So, even on more mundane things, we tend to ‘overreact’ with this passion, which can be directed to quite different things beyond a sexual partner.

Now, I’ve been crossdressing for over two decades now. It’s true that there has been an evolution, both in the quality of my crossdressing, but also in the quantity — i.e. the amount of time I’m able to crossdress, and how often I do it per week. So I’m not exactly a ‘newbie’. And for that reason, I was expecting that my mind sort of get used to the thrill of being crossdressed once in a while. Of course, there is always some thrill. I still get turned on when I finally place the wig on my head — even though, these days, I’m always in such a hurry to leave that I cannot revel in that pleasurable sensation for long. But I would have expected that the mere familiarity with crossdressing would make it become more ‘commonplace’, in the sense that I’d not be so obsessive with it any longer.

This is hardly the case. There might be several good reasons for this. Here is one of them: when genetic women go out with their friends, they also dress up. And it’s always a thrill for them to do that, even if they go out every week, or even every night. So why should it be different for us with XY chromosomes? We just react to the same stimula in this case.

My psychologist believes that the recent changes in my wife’s attitude are playing a large role in my reaction. There are some closet crossdressers who will remain closeted forever; that’s the only thing they really wish for, and once they reach that level of satisfaction, they are content. But I’m not one of them. It’s part of my personality to interact with other people — unlike my wife, who hates interacting with others, I love it. It has nothing to do with gender; it also has nothing to do with sex. It’s just that some people are naturally gregarious, others are not. It doesn’t even have much to do with being extroverted or introverted (my wife is an extrovert, but she still hates interacting with people — go figure!). It’s just that some enjoy being in touch with other people; some merely endure it, because we are a gregarious species and require being in contact with others for our survival, but it’s not mandatory that such an experience is pleasurable all the time.

In my case, however, I really love to be with others and interact with them. If I can do it in the flesh, it’s perfect; if not, I resort to online communication, which is a relatively good substitute — but it’s not the same thing, of course (it has advantages and disadvantages).

What apparently was driving me insane — without realising it — was that, as Sandra, I was always incomplete. I could dress up, even go out by myself, but I was not allowed to interact with anyone. This is profoundly against my core personality, and, as a consequence, I was frustrated — even if I didn’t realise it. After a decade of patiently asking my wife to be allowed to go out, that tension and frustration — Sandra is not really Sandra unless she is having some fun with her friends — was just building up more and more, as the desire to interact with others got further and further repressed.

So for years I had been repressing the urge to present myself as a woman. Then for years I repressed the urge to interact with others while presenting myself as a woman. All this was having a profound effect on my mind. Once my wife allowed me to go out and meet my friends, all the repression was released, like a champagne cork being pulled from the bottle. Joy overflowed. But that was not all.

Because I had never before experienced the pleasure of presenting myself as a woman among friends, that sensation was a novelty which was intensely pleasurable. And my poor repressed mind, especially because it was already burdened with a deep depression, suddenly clung to that experience like barnacles to a ship. And it triggered those feelings usually reserved for when we are in love. Therefore, my current ‘obsession’ with crossdressing, which is always present in my mind, even when sleeping, is the mechanism that my brain triggered as a response. It ‘borrowed’ the kind of feelings and emotions that would be appropriate for being in love, because our adaptable brains are so good at funneling mechanisms designed for one thing towards completely different things.

Essentially, I’m in love with the idea of presenting myself as a woman in public. That’s quite a strange kind of love!

But it’s non-functional: instead of worrying about ‘serious things’ — namely, my work, survival, and so forth — I worry about my image as a woman, constantly and all the time, and that is not good. This requires a change of my mindset. But all of you who have been in love know how hard it is. Our friends and family might give us the best possible arguments why we’re being irrational in the object of our desire, but we don’t listen to them. Our passion and lust is way more powerful than rational arguments.

Instead, my psychologist advised a completely different strategy, and one that completely baffled me. Usually, I’m quick in answering (even if I might not get the right answer!). Her suggestion, however, left me speechless for a while.

She reasoned that because the only thing that gives me pleasure is to present myself as a woman, then I should combine that with doing some work. Now, I’m lucky, because most of my work doesn’t need to be done at the office, but rather it can be done anywhere when I sit down with an Internet connection and a laptop — namely, at home. So my psychologist suggested that I simply got dressed, as much as possible, and do my work from home. Of course, she also said that I shouldn’t overdo it at the beginning. I should just slowly build it up, starting with half an hour, increasing slowly over the weeks. And, of course, after the allotted time is over, I could still enjoy being crossdressed, go out, eventually with my wife, or meet my friends, whatever. The whole point of the exercise was to make sure that during the period used for work I’m actually dressed as a woman. That way, she reasons, I would not keep apart ‘work’ from ‘pleasure’; I might slowly stop viewing ‘work’ as something obnoxious (which is unfortunately one of the worse side-effects of depression). Also, it meant that I would change my current strategy — try to do the unpleasant things first (work), finish them, and then enjoy the pleasant things next (crossdressing). She thinks that a better strategy is to start with the pleasant things first: get dressed, which pleases me so much, then sit in front of the computer, and do my work. Like everybody else, I can keep my focus for hours and hours (when I’m not depressed), but every now and then I make a short pause — and I can enjoy my self-image as a woman during those pauses. But even while working, I’m very self-conscious about my presentation as a woman. How could I not be? There is this lovely pair of breasts in front of me all the time; the silky touch of the hair on my bare skin; the smell of perfume; the manicured fingers (with their painted nails) typing away at the keyboard. Of course I cannot shut out all those stimula completely. I can get used to them (I remember the first times I tried to type with long fingernails; what a pain it was!), but they will always be there, reminding me that now I’m presenting as a woman, and this naturally triggers a sense of well-being, of comfort, of pleasure — even when my focus is really on the work itself.

Well, even though I was a bit baffled about her suggestion, I think it does make a lot of sense to me. Fortunately, my wife also agrees with me. Also, because I don’t expect to be able to go out every day, I will be dressing more casually at home — which will also please my wife, as she hates when I overdress. And I’m already planning my strategy to become quicker with my routine: today, I took little over an hour and a half, because I had painted my nails in the morning, with a very soft, transparent, pinkish colour (it’s really unnoticeable). This is something I can use every day when I present myself as a male, and, for casual wear, it looks good enough when I present myself as a female. So I save quite a lot of time there. Obviously I also simplify my makeup a bit: no need for falsies or complex shading/contouring. That doesn’t mean that I’m being sloppy — I still do my full routine, only make it simpler. That’s also important for me: I wish to become more and more proficient and take less and less time with my whole routine. My goal is to look great as my friends do, who only need 20-30 minutes to get ready (I take longer than that as a male!).

I’m not crossdressing every day yet. This is my goal, but I haven’t achieved it yet. I still need to figure out the best routine with my wife. My current plans, during her summer break, is to try to do everything — house chores, shopping, doctor appointments, etc. — in the late morning, then have lunch, have a nap, dress up, work the afternoon, and enjoy the evening dressed — either by myself or with friends. Of course, during weekends, because of all the family appointments, I will not follow the same routine. And I’m sure there will be a lot of exceptions. For instance, by the end of July, my wife is going to take some summer course at her university, and it means driving her back and forth. It will be hard to crossdress during those days, even if I become superfast with my makeup routine 🙂 But, in general, I will try to follow my psychologist’s suggestion.

I think it might work, but I also fear the consequences. So far, I have never considered dressing up every day — even if it’s only done during part of the day, because of the need to go out for shopping and other chores. I have done that only once, during a few days, in the short vacation in 2013.

Somehow, I feel it’s a rather large step to take. I’m sure that if I keep doing it for quite some time, I will insist to go out once in a while with my wife. We usually spend our free time going out to have some coffee together and a chat — even if we don’t need to go shopping. I don’t want to ‘force’ my wife to be stuck at home all day (well, except mornings). It’s boring for her. So I’ll have to persuade to come with me, even if at the beginning, we won’t be doing much except driving around, and eventually picking some ‘safe’ spots (where we are sure that nobody knows either of us) to walk around.

But many supermarkets are open at increasingly later hours. This means that I might also be able to convince her that we should go shopping for food during those times that we go out together. At first she can go shopping on her own, and I’ll just stay in the car in the parking lot. But I expect at some point that I’ll help her out with the shopping inside the supermarket as well — we just need to choose different supermarkets, where nobody knows us. Fortunately there are many!

What I’m saying is that this strategy by my psychologist to get me back into shape, fight depression, and be able to work again, might also backfire. It can have the interesting consequence that I become more and more familiar with my presentation as a woman. Think of it as a ‘Half Real Life Test’ — in the sense that even though it’s not really a Real Life Test, it can easily become something very close to it: a period of time where I’ll be out in public, interacting with other people, doing purely routine things like shopping for food. Or having a coffee at an esplanade — possibly at the furthest corner, to avoid drawing too much attention. But these would slowly become ‘regular’ activities where I’ll be pushing the limits of my public presentation as a woman.

And I might enjoy all of that. A lot.

I’m not sure if my psychologist was aware of these ‘side-effects’ when she made her suggestion. Getting cured quickly of my depression will make me do practically anything, but what will happen afterwards? Let’s look at a ‘best case’ scenario. My psychiatrist, who works in tandem with the psychologist, estimates that I will need another half a year to recover from depression — at least to be able to work again, even if I might need to continue to take medication and proceed with the therapy sessions. Ok. That means half a year of dressing almost every day. After that, I will need at least another year, take it or leave a few months, to finish up my interrupted PhD. During all this time, I will be dressing practically every day, and a year and a half is a very long period — in fact, I will be dressing far more in that year and a half than in my entire life!

After that, I’m supposed to deliver my PhD and get a job as a teacher. Now I wonder… after a year and a half of dressing almost every day… possibly even going out and doing mundane things while dressed, with my wife… will I be able to ‘go back’ to my male self and get my job done, pretending that nothing has happened?

There are always two other possibilities, one that I develop an aversion for crossdressing (it might be simply too much and too often to make it fun any more). That would obviously make things easier afterwards (and I’d stop blogging!). The other is that I learn to integrate my female and male sides better, instead of rejecting the male side; in that case, I would be just like most of my crossdresser friends, who have integrated both male and female aspects of their personalities, and do not wish to abandon either — but they keep both in a healthy balance. In other words, they consider themselves as males for their daily routine, but, like everybody else, they also have their special moment with friends and are fond of going out with them. When they do that, they present themselves as female. But it’s just natural for them; there is no stress in switching from male to female and back again, according to circumstances; they don’t suffer because of that, and their cravings and urges are not so intense. They still enjoy themselves tremendously as women! Obviously, I would love to become just like that — it would be the best of both worlds.

And, of course, I might also simply give up on my boring male side after all that time, and really not feel any enthusiasm in reverting back to it after the depression is cured and I’m supposed to take a new job and start working again.

Now that’s a problem.

I wonder if this is exactly what my psychologist is planning: to allow me to figure out on myself which of the three alternatives will work better for me. If so, she’s definitely clever; I certainly didn’t expect that. To be honest, I was actually expecting that she would slowly discourage me to crossdress, by going through ‘gender desensitisation’ (a process where we evaluate the good and bad sides of each gender, and see that there are not only advantages on one gender, and not only disadvantages on the other one), or similar processes where I could step back and take a look at the reasons for crossdressing, and see if they made any sense.

Instead, my psychologist suggested a completely different approach. A very curious one, and one that I have not encountered in the literature before. The closest thing to it is, indeed, the so-called Real Life Test. It’s certainly adapted for my case, but it definitely smells like it. Obviously, the whole purpose of the Real Life Test is for the transgendered individual to figure out how it feels to be living in the other gender, and experience all the good and bad sides. If I’m able to persuade my wife to go shopping for food with me crossdressed, this will come really close to a ‘real’ Real Life Test — it will mean that I will step out my comfort zone (outside the safety of the Lisbon LGBT quarter, or of places where transgendered people are not easily bothered). People will laugh at me as I wait on supermarket queues; they will point at me, giggle behind my back, and so forth. Will I be able to handle all of that? And what about my wife, how will she take it?

So many questions for which I have no answer…

Still, time will tell. For now, all I can say is that my psychologist told me to dress more, do my work while crossdressed, and my wife agreed with her that it’s a good strategy. So I will do that.

Let’s see what happens.

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