The Heavy Chains of Freedom

Dining @ Frei Contente, Lisbon. Picture by Joana Adriana.
Dining @ Frei Contente, Lisbon. Picture by Joana Adriana.

The recent weeks have changed completely the way I face my crossdressing urges, thanks to my wife’s change of mind. This opened up a lot of new possibilities, but, at the same time, it also opened up a Pandora’s Box of potential nightmares. And, of course, it hasn’t brought ultimate happiness.

Freedom brings happiness

I can’t get no satisfaction
‘Cause I try and I try and I try and I try

— Mick Jagger

Buddhist thought is often seen by Westerners as being very pessimistic, because it shows how, no matter how much we try, we never get enough happiness. Instead, what Buddhists say is that those rare moments where we are truly happy are just a temporary reduction of insatisfaction. Obviously, those moments can take a long time, we’re not talking microseconds here. Sometimes they can stretch for years and years.

Consider the following example: Suppose you love ice cream, and you’re given the opportunity to eat as much as you wish on a shop on the next week, for free. Your anticipation of the moment you enter the ice cream shop already makes you tingle, or even tremble with the desire of future pleasure in eating as much ice cream as possible. Finally, after a week of suffering, dreaming night and day about the wonderful ice cream you’re going to eat, you finally enter the shop, and start from one end of the shop, eating all possible flavours as much as you can. It’s ultimate bliss! Knowing that you have all those choices of flavours, unlimited time to eat as much as you wish, and no need to pay — that combination makes the experience incredibly enjoyable! It’s like paradise on Earth!

But after a relatively short while, you start to get full — it’s unavoidable, since there is a limit on how much your stomach can take. It’s time to make a few decisions. Clearly you cannot eat the whole ice cream on the shop. You have the choice of tasting a little bit of each flavour, or focus just one one or two flavours which you prefer, and eat as much as you can of those. But no matter what the choice is, sooner or later you’ll be too full even to eat little bits. Some flavours might never get tasted. Or you won’t be able to finish the whole ice cream box of your favourite flavour. Even if you force yourself to eat as much as you can, there is a point where it is simply impossible to eat more.

At this point, frustration sets in. You have been given a wonderful opportunity to do what you like most, without restrictions, but sadly your body cannot keep up with the opportunity. Yes, you have eaten far more ice cream than you usually do. But it’s still not enough. A lot more ice cream remains uneaten. And soon you will have to go back home, thinking about so much wasted ice cream that you had to leave behind. Worse, you might even now have some belly aches from the incredible amount of ice cream you’ve eaten. Was it worth it, after all? Sure, we might say, it was great, next time I will know how to choose better, and eat even more. And then you’ll start dreaming about the next opportunity to do the same, day and night, recollecting the wonderful moments you spent eating ice cream, and regretting that you had to stop so soon.

And so on, and so forth.

This naturally is true for everything you do in your life. Like Mick Jagger so profoundly put it, no matter how hard you try, you will never get satisfaction from anything you do. Even if you were able to eat all ice cream in the shop (after training for weeks to stretch your stomach to superhuman sizes, and increasing your weight to 300kg!), you’d be unhappy that there is no more ice cream for you to eat. Indeed, there is really no way to subvert the system: no matter how clever and how hard you try, there is always a limit to how much ‘temporary satisfaction’ you can get.

There is, however, the other side of the coin. Insatisfaction is of course much greater when you’re constrained and limited. Imagine that you love ice cream, but were forbidden to eat it. Obviously that entails much more insatisfaction, because, no matter what you wish, you’ll never be able to eat it; you have no freedom to enjoy ice cream, and all lack of freedom produces insatisfaction. In Buddhist thought, ‘freedom’ and ‘satisfaction’ are almost synonyms: you cannot have one without the other. That’s why Buddhists talk about ‘becoming free’ from the chains of this world — that ultimately means learning the trick on how to be happy in spite of all the lack of satisfaction.

It seems pretty much impossible, but the good news is that it isn’t; it’s actually very simple, it just requires years or decades of practice. All you need to figure out is what ‘binds’ you and creates that insatisfaction. For instance, if you crave ice cream, that’s what causes the insatisfaction. By merely enjoying ice cream, instead of craving for it, you get rid of the associated insatisfaction. In that case, whether you eat ice cream or not is not very relevant for your daily life. If you have the opportunity to taste it, then, yes, it’s an extremely pleasing experience, and one that brings some happiness in your life. But if you have to forfeit ice cream for long stretches of time, it doesn’t bother you. This is the actual concept of ‘freedom’ in Buddhism: not ‘freedom’ in the sense of ‘doing whatever you please’ but rather being free of the cravings, of the constant expectations, of those desires that we cannot seem to be able to ever fulfill, and so forth. Happiness in Buddhism is being free of all that. What remains? Pure enjoyment of pretty much everything that happens to us, without feeling any sort of attachment to those things.

I’m not saying it’s easy. I’m just saying it’s simple. It seems actually pretty reasonable. Achieving it through Buddhist training is, of course, another story — it’s not something you can do with a workshop over the weekend, or even just by meditating a few minutes per day. It requires truly a massive effort — at the level of commitment of an Olympic athlete or a top musician in an orchestra — but we know it’s possible. Human beings are able to do extraordinary feats when they fully commit to something they really wish to do. We look at the examples of Olympic athletes, just to give an example, and wonder how they manage it. The answer is simple (but, again, not easy): they commit all their time and all their lives to improve themselves. If we’re not able to commit ourselves at that level, then we won’t become Olympic athletes. The same applies not only to physical feats, but mental ones. Nobel prize winners might be brighter than most people, but, like athletes, their true secret is the level of commitment they have put on their studies and research. Just because you might be very clever that won’t necessarily mean you’ll get an award for your intelligence; the mind also requires training, and that’s what scientists do all the time. So we know we can train our mind to become better and better at what we do, and we can certainly also train our mind to ‘become free’. In a sense, Buddhist practitioners are Olympic athletes in mind training.

Alas, for us that are not willing to commit to that level, for various reasons, it also means that there will always be some chains that prevent us to be free from all those cravings, urges, desires, and expectations that we constantly have. The best we can hope for is that some external circumstances change, and, through that change, we might achieve a slightly higher degree of freedom.

In a sense, that’s precisely what happened to me, and, to be honest, after so many years of being ‘locked in’ by all constraints, such amount of freedom feels rather strange. But of course it also means more happiness. However, it’s still happiness bounded by insatisfaction. The only thing that I’ve been able to achieve is a longer period of ‘temporary reduction of insatisfaction’. That still feels great, but it also feels different.

Experimenting in the closet

A friend of mine defines non-fetishist crossdressing as the desire to manifest one’s female self-image in a way that shows appreciation of the female gender. On a previous post, someone on the comments saw that as a very machist thing. Somehow, it seems, people who have been unfortunate to be assigned the male gender are not ‘allowed’ to appreciate the female gender to the point of paying tribute to it by crossdressing. Granted, it’s just an opinion, but even so, it gave me some opportunity to think about both views.

People crossdress for all kinds of reasons. The more one looks into the diversity of crossdresser types, the more types there seem to be, and not everybody agrees on what exactly drives them to crossdressing. Definitions, classifications, labels sometimes help to create a ‘consensus’ on what’s it all about, even though every individual will only fit partially into those classifications. I often make the mistake of separating quite clearly the fetishist from the non-fetishist crossdressers, but it’s also clear that non-fetishist crossdressers have fetishes on their own (as I explained on my previous post). So there is obviously a continuum.

However, even in spite of that continuum, we can still find some traits that are more common to a group than to the other. Consider evolutionary biology, for instance. We can still differentiate between species, based on their characteristics, even if we know that ultimately every being is a ‘species’ of their own (even Darwin recognized that, over 150 years ago). Still, we can differentiate between a ‘cat’ and a ‘dog’. Both are mammals, both have a common ancestor (probably some kind of rodent…), both have a lot of similar characteristics. Sometimes they even look alike; a Pequinois, seen from certain angles, might look like a very fluffy cat. And some dogs have ‘cat-like’ personality traits, and some cats have ‘dog-like’ personality traits, but, in general, we can still differentiate between a cat and a dog, and most people (and most animals, too!) will pretty much know the difference.

Obviously the analogy is a bit stretched; human beings aren’t as different from each other as cats are different from dogs (because they’re really different species). So it’s a bit unfair for me to say that fetishists and non-fetishists are as different as cats are different from dogs; obviously that is not the case. What I mean is that there are certain characteristics that we can identify that are more common among non-fetishist crossdressers; and other characteristics which are more common among fetishist crossdressers. There is a huge overlap, but there are also differences.

Among non-fetishist crossdressers, for instance, there is this notion that it’s important to ‘be a woman’ (or, in other words, manifesting externally one’s inner self-image as female) beyond merely ‘having sex as a woman’. Of course ‘having sex’ is also a fundamental part of human nature, and, as such, it’s natural that even non-fetishist crossdressers want to have sex as a woman. But there is far more to ‘being a woman’ than merely to have sex as one. This is a typical difference among the two groups. True fetishist crossdressers see little point in crossdressing unless there is something sexual happening (even if it’s not the sexual act itself, but merely the possibility of sex, or the sexual pleasure derived from wearing women’s clothes). Without that, crossdressing is pointless for them — it serves no practical purpose. Put in other words: what’s the point of dressing up, wasting hours in doing makeup, buying a lot of clothes and accessories that will not be used elsewhere, going out, risking a lot of things, if there is no guarantee of at least some sexual fulfillment at some point? It seems rather a waste of time and money!

Non-fetishist crossdressers have the exact opposite view. There is a vast amount of experiences that only women can have (sex being obviously one of them) and it’s only through crossdressing that those experiences can become (at least partially) available to someone who has been unfortunate enough to have been assigned the male gender at birth. In some cases, of course, male crossdressers are more than happy with their gender, they just wish to expand the range of possible experiences by embracing the female gender as well. Others, by contrast, find little pleasure in the range of male experiences and are just interested in experiencing the female ones, and sometimes that even requires some body modifications. Again, we see here a continuum, where at one end we have gender fluidity, and at the other end, we have transexuality.

Perhaps at the very beginning the first ‘experience’ a crossdresser gets is related to the sense of touch — women’s clothing just feels so completely different. As the crossdresser begins to develop, there are a lot of more new experiences which are outside the scope of the male gender. Makeup, for instance, can bring about drastic transformations. Suddenly you have a way to look completely different, just by painting your face. Except for male actors or TV anchors, and sometimes some politicians who regularly wear makeup, males usually never have that sort of experience. It brings a sense of wonder, but also one that questions one’s identity: after all, that face which I have been labeling as ‘me’ for so long, can suddenly look quite different — is it really still ‘me’?

Compared to other primates, humans exhibit a relatively low sexual dimorphism — a technical term to designate how much each sex differs from the other in the several species. Consider some extremes: chicken are really very different from roosters, while most male cats will look almost exactly like female cats (at least to a human observer!). That means that while individuals vary a lot, the physical difference between males and females is not that great. However, through social conditioning, and probably also due to evolutionary reasons, gender roles have augmented those differences deliberately through artificial means. That includes a lot of attitudes, behaviours, gestures, grooming, and, of course, dress code, all of which consist in what we could loosely call ‘gender expression’. In other words, because the physical difference is not that big — except for primary and secondary sexual attributes — by adopting those ‘artificial’ means of gender expression, males can attempt to ‘pass’ as females and therefore experience a little bit of what genetic females experience.

I know that this paragraph is controversial. In general, just as we can easily differentiate between a dog and a cat, we usually can differentiate between a male and a female. It’s very easy if both are naked, even if they have the same size, haircut, etc. because the sexual attributes are clearly different. On the other hand, if we have two humans of different sexes fully clothed in unisex clothing, and if they have the same height, overall size and proportions, the same haircut, and so forth, it will become increasingly difficult to differentiate between both — that’s why humans are said to exhibit a low sexual dimorphism. Because of that, we artificially ‘enhance’ the difference through social conventions.

Obviously there are differences. A woman’s face will always be different from a male face in certain tell-tale signs, just to give an example. Here is where, again, social conventions help us: makeup is used by women to enhance those differences, but, of course, males can use makeup to achieve similar effects. There are a lot of ratios between the different components of the face (for example, the distance between the nose and the upper lip) which are typically feminine, but, through clever application of makeup, one can give the illusion that one’s face is more feminine than it actually is. Women do that kind of emphasizing all the time (perhaps not even fully conscious of why they do it), so males can do pretty much the same, at least up to a degree — it’s impossible to disguise a huge nose (even though women can have large noses too!). But higher cheekbones, a softer jawline, fuller lips, larger eyes (and longer eyelashes), all of which are typically female traits, can be achieved with makeup. Or, at worst, they can be covered up. Large ears, for example, can be disguised with long, thick hair.

So I’m not saying that there are some ‘magic’ tricks that can make a male automatically pass as female, and of course this depends a lot on one’s overall body type — some types are incredibly difficult to disguise, others are easier. What I’m saying is that some male crossdressers can effectively pass as females — perhaps not all the time, or not in front of everybody, but, in general, they might be able to do a reasonable job in passing. And that happens because those gender differences are mostly artificial, and we’re socially conditioned to take notice of those first. Here is a typical example: in the Western societies, it’s far more likely that someone with long hair is female than male, although nothing prevents males from wearing their hair long; it’s just a convention that females, in general, have much longer hair than males (but historically this is definitely not true for all ages and countries!). The hair attracts a lot of attention, because of its size, and the way it frames the face, so typically a male crossdresser will try to invest in a good wig (or grow their own hair long), since it will help so much in artificially expressing a female gender.

So for the past two decades I have been experimenting with all that. I use not only the mirror, but also pictures and videos, to evaluate the results. Unfortunately, I must have some sort of body dysmorphia, since I almost never see myself as others see me (I’ve written about an exception on my previous article). That was one reason why I turned to webcam chatrooms. There I would be ‘exposed’ to the opinion of others; what would they say about me?

Unlike what my friends claim, almost everybody on those chatrooms immediately recognized me as being male and had no qualms in addressing me as ‘ugly’. The exceptions would mostly be males from Islamic countries who perhaps get easily confused when they see Western females (or males presenting as females).

This was not really a source of frustration for me, but, rather, it gave me energy to study more, to experiment more, and to learn more about those subtle differences which can be masked or enhanced to appear more ‘female’. As time passed, I learned a lot from all those experiences. I haven’t yet learned how to ‘pass’ 100% of the time, but I saw some improvements, which encouraged me to experiment more and more.

Out of the closet

A few years ago, my wife finally changed her mind, and allowed me to go out fully dressed — but only in the middle of the night, long after everybody (namely, the neighbours) were asleep. This allowed me to explore the feeling of being dressed as a female on the street. You know some of the clichés: the sound of the high heels clacking on the pavement, the breeze up your skirts, the hair fluttering in your face, the rustle of the clothes. Again, the sense of touch predominates in these experiences, but there was really not much more to it. Once in a while, of course, I would be seen by someone on the street, and immediately caught their attention. It was, however, very hard to say the reason why they looked at me. When there are so few people on the street at that time, they might just have looked because there was nobody else around. And all this happened from far away in any case.

Things started to change when I was allowed to go out much sooner, during our short holidays in Algarve, last spring. That meant actually walking on the streets and meeting people who were around; they would be in relative proximity, even though I usually avoided the busiest places. Now I was relatively certain that I was drawing attention, but I still was a bit unsure of the kind of attention I was drawing. My few interactions while dressed, at petrol stations, showed me that the people in Algarve had no problems in talking to me, rather the contrary. I shrugged it off because they’re used to all kinds of odd tourists and, as such, are always polite to anyone. I did enjoy being oogled by one petrol station attendant, who was very interested in my cleavage 🙂

Those experiences were exciting. It was still a bit unclear about how people perceived me, because, as said, Algarvians are usually polite towards everybody. Did they read me as female or just as a perverted male, to whom they nevertheless showed some respect? It was really impossible to figure out. So that experience left me a bit undecided, but at least confident that the Algarve is a relatively safe place to walk around crossdressed. In fact, when I visited my friend Cláudia during Carnival, I had exactly the same experience: Algarvians, in general, care little about how people look like, because they’re so used to all sorts of oddities. Of course, being Carnival, nobody would mind.

There was, however, a hint of something else. During that trip, if your remember my other article about it, I had stopped mid-way to use the toilet. I thought that I would need to get a key first (they usually are locked), so I stepped into the shop of the service area to ask for the key. I was expecting a moment of shock as the attendants had to deal with a crossdresser. But that didn’t happen, which actually surprised me. Instead, most people in the shop didn’t look at me as if I were an ‘oddity’. For an instant at least I got the impression that they thought I was just a rather large female, which wouldn’t be unusual, since that motorway is used by all sorts of tourists to drive to the Algarve. In any case, I was in casual clothes, with subtle makeup. Maybe some of those people were fooled in believing I was female; maybe after a second glance they were not, but, being Carnival and all, they simply went along with their politeness and never raised an issue.

Again, I was undecided about how real people — outside the realm of webcam chatrooms — did actually experience my presence.

Since Carnival, my wife definitely completely changed her mind, and now is fine with me going out with friends. That means leaving home much earlier than usual, and interacting with people that will inevitably see me. Of course I try to rush into the car as quickly as possible to avoid being seen by neighbours — but, in truth, I have been seen almost always. So far, I have not heard any comments.

When going to a bar to meet my crossdresser friends, I momentarily lost my bearings, and had to ask for directions (those small streets are often confusing!). I had no problem entering a different bar and asking for the right one, because that particular quarter of Lisbon is favoured by the LGBT community, so it would be all right. In fact, I was pretty much invisible on the streets; few people cared to look twice at me, because they’re so used to all sorts of ‘queer’ people (no offense whatsoever meant) in that area. It feels like a safe place because of that.

Then we had an event where we would walk in a public place, quite outside the LGBT quarter. That would mean meeting people who would not expect any crossdressers walking around in public. These events are usually on Sunday night, after 11 PM or so, and because most people will need to work on Mondays, it means that there are not many people around (except perhaps during the summer holidays). We certainly attracted some attention, but not so much as I expected; we were also very careful.

Last Saturday, however, things were a bit different.

Because it was the Easter weekend, most of the people in our group had to be with their family on Easter Sunday. We decided to shift the date to Saturday instead. Because it’s a ‘long weekend’ (Friday is a Christian holiday), and the schools are closed for the Easter holidays, it was highly likely that there would be far more people on the streets, even at 11 PM.

But there was an unexpected surprise for me. One of the members of our group has no car, and she needed a ride. Unfortunately, she doesn’t live alone, but has to dress up at a friend’s place, and her (genetic female) friend only had time to allow her to dress (and help her with the makeup) until 7 PM. That meant I had to pick her up in broad daylight, have some dinner together, and join the rest of the group at 11 PM.

My wife was not very happy about the whole situation. One thing is to leave home in broad daylight during Carnival; the other thing is to do so on a normal day. I wasn’t expecting to actually be on the street for a long time, though; just enough to enter the car, drive to the appointed place (a parking area in front of a mall), pick my friend up, and go to the restaurant, which is in the LGBT quarter, so everything should be fine there.

There was an unfortunate setback. My friend was nowhere close to being dressed by the appointed time. So I had to wait a full hour, sitting in my car in broad daylight, in the parking area.

Plenty of people were constantly passing by; cars parking and going out again, often next to my spot. It was a busy hour at the mall, with people doing their shopping before dinner, or to stop at the mall to eat there. There are some preparations that need to be done for the traditional Easter family lunch, and Portuguese are often procrastinators, doing things at the last possible minute; as a result, the mall was really very busy. So busy, in fact, that there were even two police cars in the parking area! I parked opposite of them; not that the police has any problem with us, since they have been lectured about transgendered people, but mostly because they would certainly act upon complaints — private places, in theory, have the right to exclude people from their premises. This is technically not considered discrimination, but I guess that a good lawyer could win a case… however, I wasn’t really in the mood to cause any problems.

So there really was no way to avoid being seen. Sure, they could only see me from the torso up, and sitting down inside the car my huge frame and overall height is not so apparent. But still there was really no way to hide. I spent most of the time observing people’s reactions, while keeping in touch with my friend via text messages.

What actually shocked me was how I was absolutely ignored.

People would pass right in front of my car and never look twice — sometimes, not even once. Others would park their car just next to mine, open the door, glance quickly to check that they weren’t bumping into my car, noticing my presence, but that would be all. Sometimes they would walk from a long way until they came near me, having ample opportunity to look at me, but they would not even comment anything among themselves.

I seemed to be completely invisible.

And that was for me a great feeling!

Some of you might think that it would have been best if people would check me out, whistle, say things like ‘oooh what a gorgeous babe’ and so forth. But that’s precisely what I do not wish! For me, ‘passing’ as a woman means mostly being ignored, in the sense that people don’t even notice that I’m not a genetic woman. After all, on the street, we pass across thousands of people every day. We’re not whistling and cat-calling to every woman on the street, not even look twice at them, unless they somehow attract our attention — usually, because they ‘stand out’ in any way.

I wish to be part of the invisible mass of people on the street. The person that doesn’t attract any attention whatsoever. That would mean having much more freedom to enjoy — the freedom to go anywhere, to do whatever I wish, and not being ‘read’ as a crossdresser.

So that moment was rather special for me… my question only was: was this an exception? People didn’t see me fully, since I was sitting inside a car. What about being on the street?

Unleashed

Later on, I would have exactly that opportunity to test it. After picking up my friend, I drove as fast as I could (I’m a very slow driver!) to the restaurant. We had reserved a table for just one hour and a half, and that meant we couldn’t be late, or risk not having dinner at all.

This was at a popular LGBT-friendly restaurant in the old part of Lisbon, full of tiny streets and few parking spots. Because it was a Saturday on a long weekend, I was a bit afraid of not being able to park near the restaurant. By chance, I got a free spot at the very beginning of the street — about 300 m away from the restaurant, and 100 m higher (yes, Lisbon is a very hilly city!) — right at the corner with a major thoroughfare.

My friend needed some minutes to fix her shoes inside the car, so I just stood peacefully outside and had a smoke. And once again I managed to watch and observe how people took notice of me.

And again I felt pretty much invisible. Oh, sure, of course some people glanced at me briefly, but there was not even a sign of recognition that I was a ‘weirdo in a dress’. They just took notice that I existed and that was it — they went along their way. One young girl probably spent a few extra seconds looking at me. I was particularly surprised that even children didn’t make any comments — you know how kids have no inhibitions, and I was expecting at any moment something like a cry of ‘daddy, daddy, why is that man wearing women’s clothes?’ But nothing of the sort happened.

(Actually, some weeks ago, when I was buying some makeup for myself, a very cute 6-year-old at the queue presented me with her brightest smile and said, ‘you can’t buy that, that’s just for girls!’ to which I replied with my best smile and simply asked: ‘why?’ This, of course, got from her a lot of giggling.)

I have to admit that I was a bit baffled, but also very happy. Because I saw many tourists as well, I couldn’t simply shrug it off saying that it was just the typical politeness of the Portuguese. Some tourists might have had no idea that they were entering Lisbon’s LGBT quarter; it’s not as if there is a road sign saying, ‘Warning: LGBT quarter ahead. You might encounter crossdressers.’ Even asking around at a hotel might not have given them that information; most Lisboners do not know that this is a LGBT quarter. In fact, some years ago, not even I — who have lived in Lisbon for 30 years and still work there — had any idea that Lisbon already had a LGBT quarter!

So it’s fair to assume that those tourists had no clue, they saw me, and… just ignored me.

That was actually quite a feat!

The alternative explanation is that I was very lucky and just saw very open-minded people on the streets, who care little who people are and how they dress. That’s certainly a possibility, but it’s also curious. Since when have my fellow Lisboners become so enlightened? There is actually relatively little information about transgenderism available to the public at large. The police and most teachers have been given some training regarding transgender issues, but most people have no idea what it is. At best, they believe it’s some kind of mental disease. At worst, they just think it’s a perversion; not everybody will react violently against it (Portuguese are rather peaceful), they might just ignore it.

In any case, it was a very good feeling.

Of course, once my friend got out of the car, things changed; she was rather provocatively dressed and had the intention of catching attention, so naturally that’s exactly what she got.

Closing the closet

After dinner, we met the rest of the group to have a nice walk around one of the most modern quarters of Lisbon; it was built in 1998 for the world Expo held there. It’s a large area by the river — quite flat, which is awesome for those who walk on heels! — with a mix of leisure, commerce, offices, and residential buildings. This time we walked along the marina, where there are a lot of bars and cafés. Being Saturday evening during a long weekend, it wasn’t empty. Not exactly crowded — there are far more popular leisure quarters in Lisbon — but there were certainly hundreds of people around.

Our group was mixed: half was crossdressing, the other half were just friends. Because we walked together, we didn’t attract so much attention as if we were a large group of just crossdressers. In fact, from a certain distance, it wouldn’t be so obvious who was crossdressing and who was not. Nevertheless, we were obviously ‘read’ by many — but since we were a relatively large group, there was no problem whatsoever. People must have thought that we were quite odd, because of the mixed nature of the group, but that’s ok. We didn’t stop at any of the bars and cafés, since we have no idea which ones might have been LGBT-friendly or not — we just walked around and took some pictures.

At the very end, after two hours of walking, it was time to drive my friend back to her home. She put on her male clothes in my car, but forgot the nail polish remover. Since I was low on petrol, I suggested that we stopped at a petrol station, which sometimes have a small convenience shop where they might sell that.

My friend might have gone out and ask, but at the end of the day, it was up to me to pay for the petrol and ask if they had nail polish remover. Well, I had already interacted with petrol station attendants in the Algarve. This, however, was Lisbon — quite a different environment. Worse than that, the station was not empty — a lot of people were there, and I had to wait on a small queue to pay.

All people at the queue (as well as the attendant) were male.

They barely noticed me.

Again, I felt invisible. Sure, one of them turned around to take a short look at me, lost interest, and focused on remaining on the queue to pay. That was certainly unexpected. It was bright enough for them to notice that I’m not really female. The truth is that they completely ignored who I was or what I was. If they ‘read’ me, they most certainly behaved as if they hadn’t noticed anything.

Obviously the attendant had no doubts about my crossdressing. But he certainly didn’t hesitate a second, was very polite, and definitely did some eye contact. I was a bit baffled. I expected at least a smirk, or a remark. There was absolutely nothing of the kind. He just said that they didn’t sell nail polish remover, accepted my card, and that was it. So I returned to the car, looking at how the other customers paid attention to me — and just got nothing. They simply weren’t paying attention. Sure, there was a glance or two, but exactly what anyone would expect. No comments, no smirking, no chuckling, not even a knowing smile — nothing. I was completely out of their minds in perfect invisibility.

Well, you cannot imagine how much this boosted my self-confidence!

I spent the next few days thinking a lot about all these experiences. Looking back at my trip to the Algarve, it’s true that I have been addressed politely on my trip there. I’m always making up excuses about why this had been the case — it was Carnival; shop attendants are always polite to any customer; Algarvians are especially tolerant with ‘weirdos’; and so forth. But it becomes more tricky to explain the same kind of reaction in the middle of the street in Lisbon, or on a busy petrol station outside the ‘touristic’ areas. I might assume that ‘all petrol station assistants are polite’, and so, even if I was ‘read’, I was a customer, and, therefore, all they cared about was to provide a professional service. But that certainly doesn’t apply to bystanders. Nevertheless, either in broad daylight — like at the parking area of the mall — or during the night, but on relatively well-lit areas, the truth is that when I’m on my own, I seem to be invisible. Or, at least, as invisible as I am in my male mode. Sure, people see me. But they don’t make any comments. And most often they don’t even look twice.

The strange thing is that I would look twice! When I chanced to see a young crossdresser in a group at Lisbon’s biggest mall, I most certainly looked twice at her. But I also noticed that I was the only one doing so. She definitely did not look like a genetic woman; her wig looked too fake, and she wasn’t even very cleanly shaved, and didn’t use any makeup. So of course she was quite easy to ‘read’. Nevertheless, most people simply ignored her.

At this stage, two things might be happening. The first is that truly the Portuguese are becoming more tolerant somehow. As if by magic, since nobody is really teaching them how to react to crossdressers, and they are not that common anyway — not in public places. This would go a long way to explain their reaction. The other possibility is that I don’t stand out as easily as I thought, when dressing as a woman. My wife suggested that this could be due to my German blood: when dressed as a woman, my German ancestry might stand out, and, because Portuguese have the idea that all Northern Europeans are incredibly tall and large, they might shrug me off as merely an ugly, large foreigner, and not really notice that I’m not really a woman. That is certainly a possibility.

Whatever the reason, the result was that I certainly acquired a lot more self-confidence. While I might not yet have found the true cause for that unexpected behaviour, the end result is pretty much the same: when I’m in public by myself, apparently I don’t stand out, or at least not enough to catch undue attention. That’s good to know!

Naturally, I need to experiment more, under different settings and circumstances. I cannot form my opinion yet based on merely a few scattered events. But, in general, I was quite happy with the resuls of those experiences!

To conclude, I would get back to my opening remarks. These few past experiences have improved my self-esteem and my self-confidence. I’m trying very hard to see myself as others really see me, and, as a result, I feel much more confident in my role as a woman. That, in turn, boosts my happiness. Or, to be more precise, slightly extends that period of temporary relief of insatisfaction. I’d say that’s far better than nothing!

Will this also help me to get rid of the depression? Well, so far, it hasn’t been enough. People with some kinds of atypical depression — which is my case — always respond positively with mood improvements while subjected to positive events. Going out crossdressed with my friends is definitely something which I enjoy a lot. So much, indeed, that I spend the whole week thinking about how great it was. I desire more and more of it, but just going out and having fun expressing my preferred gender identity is not enough. There is a lot more work to do.

Incidentally, some of my medication might make me more willing to take risks. Because some of the symptoms of my depression include anxiety, I’m also getting some medication to reduce anxiety — not exactly classical anxiolytics, but more sophisticated drugs which don’t create dependency. That also means that I’m supposed to become far less anxious when going out. In fact, the only moment when I feel a little anxious is when I leave my home and enter the car — mostly because of the neighbours. The truth is that a lot of them have already seen me; it was pretty much unavoidable. None, however, have remarked upon it.

Once I’m in the car, the anxiety evaporates. Then I’m just Sandra enjoying myself, and pretty much everything else is irrelevant. To be honest, this has always been the case, even without medication. The drugs might just make me even more brave, even more willing to experiment different settings and environments. On the other hand, I still keep my wits and I’m unwilling to take unnecessary risks. There is a balance to be found.

There is a whole new world slowly opening in front of me, and I feel the urge to explore it and examine and analyse my feelings. There are still a lot of limitations on what I can do, and what I cannot do. But merely having the idea that those explorations are now possible seem to give me a new sense of freedom, and, as a result, increases my happiness.

But with greater freedom also comes greater responsibility. I’m out of the closet now, in this brave new world which I’m going to explore. Doing so involves risks — much higher risks than sitting at home behind a webcam. So there is no ‘ultimate freedom’ in this case, but a constrained freedom — knowing what to do with that freedom, knowing when to stop, and how to make the most of it (while it lasts!) will be my next steps.

Today I got interviewed for an academic research about the Portuguese transgender communities. At some point the researcher asked me what my future would be — ironically, the same question that my psychologist asked a few hours earlier. I have to honestly say that I don’t know. It’s really too early to say. I can have dreams and far-fetched hopes which are utopic, of course; who hasn’t them? But I will most definitely remain in the realm of what is actually possible. At this current stage, I’m not exactly sure what that will be. I have some ideas, of course: I would like to go out dressed with my wife, go to public places, even if it’s just to the supermarket doing some shopping. I can still imagine revealing myself to my mother-in-law. I might ‘come out’ to some very close friends and a few familiars. And maybe that’s all I’ll do. Or I might start doing some slight changes to my body, beyond laser hair removal. I sincerely don’t know. Most likely, I won’t be doing anything before I get a full diagnosis on my mental condition by the team at the psychiatric hospital where I have my sessions. It’s something I cannot do on my own; I have absolute trust in experienced doctors who have gone through hundreds if not thousands of similar cases, and who are trained and much better prepared to identify who I am and what I am. Before they arrive to a conclusion, it would be very premature for me to take huge steps — baby steps is what is recommended at this stage, and that’s what I’m going to do. For now.

In any case, I really need to think a lot more about it. But that’s easy for me, I have been doing that for years and years, and adjusting my mindset according to my new experiences and introspective self-exploration…

  • Brilliantly written-
    The thoughts of cross dressers are wonderfully explained-
    Yes, we take lot of efforts transform into a beautiful woman, and try to derive a little bit of sexual excitements-
    I got immense pleasure once I came out in lady dress night time and traveled in a bus a total of 260 kilometers.
    In the bus a middle aged gentle man caressed me as I was looking sexy.
    I too enjoyed the mischievous acts he played with me after the lights went off in the bus during the journey.
    Truly bliss ed to have that experience-
    Thank you Sandra for writing such a heart touching article-

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