Going out for the first time with a friend

Patrícia e Sandra

There is a new word I’ve learned last Thursday: when a CD takes you out for the first time en femme, offering her support and experience, and putting you at ease, she becomes your godmother. 🙂

Now I have a godmother too! 🙂 And doesn’t she look gorgeous in the picture on the top?

But I’m getting ahead of myself. Like everything else in my complex life, this event has its own story. It starts some 15 or so years ago — when, for the first time, a CD acquaintance I had met online suggested that we met and went out together en femme.

I’m almost ashamed to say that around that time I couldn’t yet afford to live on my own, so I had to rely on my parents to provide me with shelter and food (don’t get me wrong, I love my parents!). This, in turn, meant a limited capacity for crossdressing. But I still had the vacations on my own — I spent part of them alone, where I could indulge in crossdressing. The problem was that it became hard, if not impossible, to synchronise the days I was on vacation with the days my friend was available for getting dressed as well: so this never happened.

Shortly afterwards, I moved to my own place, where I hoped to be able to crossdress much often. But it was the exact moment in time when I also met my current wife, and, of course, all free time was spent with her — and she moved in with me not long after my new place had been restored and decorated. Even before that happened, she would already sleep over the night with me during weekends. Afraid that she’d find out what those strange black bags were, and why I never opened them, I kept all my femme things stored away — in the trunk of one of my cars, where, among all the junk, they wouldn’t attract much attention. So there was a big dilemma there. My daily routine was to go to work, pick her up, drive her home, spend as much time as I managed before collapsing in exhaustion, and drive back to my own home to sleep until morning. During the weekends we spent almost all waking hours together. Effectively, even though technically I had my own place and freedom, didn’t talk much to the neighbours, and nobody would visit me, in practice I hardly managed to crossdress at home. It happened just once or twice and was never a “full” session. In fact, I continued to dress only during my solitary vacations (because we couldn’t match vacation days together, my wife and I had to take them separately). And by that time I hadn’t much time for vacations anyway — a week per year at most, if at all.

When she moved in with me full-time we went through a very complex time of our lives, during which I literally lost all my money to creeps and scoundrels — and to the incompetent banks which panicked during the crisis of 2001-2003 after 9/11 and the burst of the dot-com bubble. We had even to leave our home and get to live far away for half a year. It was only when we returned that I had to make the decision to reveal myself as a crossdresser. As you who follow me know, this went rather well, but my wife imposed some rules and limitations: I could dress at home occasionally with her consent, but she didn’t want me to leave the safety of our place. After seven long years, she finally consented to revert her decision last January, but, again, with the restriction that I could only leave home after she went to sleep since she gets so anxious about my leaving that she doesn’t want to face it.

Now I go out practically every day I manage to dress. The problem, of course, is that she goes to bed very late — never before 2 or 3 AM. This means that by the time I wait for her to get sound asleep — she reads in bed for a long time, smokes a few cigarettes, and then takes perhaps another half hour to finally get asleep — I’m already very tired, it’s insanely late, and everything has closed. There is always the fun of driving around and walking on my heels on the cobbled streets, totally empty (or almost!) by then. The only people who complain are my long-time online acquaintances and friends, since the time I used to spend with them in loose conversation are now replaced by going out. I’m sorry about that! But it’s hard to do both things…

Well, most crossdressers work full-time in “male mode”, so this means that going-out times are only on Fridays and Saturdays. Which are precisely two of the nights that I never have free: I’m studying on Friday, and I go to my mother-in-law’s place on Saturday. There are, at most, one or two exceptions per year to this rigid schedule, and it’s impossible for me to know them in advance… so I never, ever, plan to crossdress on either of those days. In Portugal, we still have some holidays which fall in the middle of the week (something which might change in the near future) so sometimes there is the slight hope to go out at a time where other crossdressers might have some time as well — but, so far, this hasn’t happened. Also, the time I can go out is only when everybody is driving back home — which means missing fun entertainment like going to dinner parties or some shows since they will all have finished by the time I’m allowed to go out.

Over time I sort of resigned myself to the futility of expecting conditions to change. The studies I’m doing on Friday will only finish in about 3 years or so, and it’s possible that they will be extended; my mother-in-law is not likely to change her weekly dinner date soon, either. And for the remaining weekdays before a holiday, it’s unlikely that my wife gets less anxious about me going out earlier — or to assume that my friends are willing to stay up so long and wait for me.

A few weeks ago I was sort of grumbling and complaining about that to Patrícia Coelho. Patrícia is a very interesting case. First, she’s insanely clever, which is the kind of person I’m comfortable with — I love challenging people, and anyone brighter and more intelligent than me keeps me on my toes and grabs my attention 🙂 But more to the point, she has picked up crossdressing very suddenly not even a year ago and instantly became one of the most valuable members of the Portuguese crossdresser community. After her few shy experiences, her drive to pass with a perfect female figure catapulted her into becoming one of the most fashionable, good-looking CDs I ever saw around here. She goes out at least twice per week, but often 3-4 times; and is currently planning her transition, probably thanks to a very supportive (new) girlfriend who accepts her as Patrícia and might have encouraged her to move on. No, it’s not as easy as it sounds for her, either — she wouldn’t be accepted in her workplace (which is highly sexist), and changing careers at this time is not a very practical choice. But she’s considering the challenge; in her own words, there is little more she can do to enhance her feminine figure without going through hormone therapy and eventually some surgery. And in her desire to achieve perfection, this seems to be the natural course of things to follow.

Let me open a short parenthesis. Someone who never crossdressed in her life and all of a sudden plans transition after a little less than a year might seem surprising to most. But in fact, in the past two years, I have been astonished at the ever-increasing number of acquaintances and friends who are doing exactly that. If it were restricted to my country, Portugal, I could understand — after years of repressive legislation (which ended in 1974), transition was a highly-complex bureaucratic procedure, with lots of pitfalls, which had to end with the transexual person filing a lawsuit against the Portuguese state in order to get the gender change accepted. While this was a mere technicality (the courts would always allow the gender change to take place), it meant years and years of waiting with very hard access to surgery and hormonal therapy, few doctors and psychologists familiar with gender identity problems, and universal ostracism. The new law changed all this and it’s one of the most advanced in the world: nowadays it’s merely a bureaucratic, administrative procedure, which starts with getting assigned to doctors from the National Health Service who will evaluate the transition procedure, recommend therapy, and formally emit a professional opinion to allow the gender change to happen, which is then accepted by the central registries to formally change the name and gender on all legal documents. All the medical aspects of the transition procedure are paid for by Social Security. Gender has been disconnected from genitalia; nobody is forced to go through hormone therapy, surgery, or chemical sterilisation (yuck!) to change gender since same-gender marriage is also legal (the sole limitation right now is that same-gender couples cannot adopt children; but they can adopt them before they get legally married). Even the “Real Life Test” seems to be less strict as before: many are allowed to go through therapy even before starting the Real Life Test (it makes sense: it’s far easier to pass as a woman in the Real Life Test if you already look like one). It sounds “perfect” but of course it isn’t — the bureaucracy takes a lot of time, about 2-3 years until the transition is finished, but it’s a far less painful process, and obviously much cheaper, too. It’s not unexpected to see so many repressed transexuals all suddenly applying for a gender change.

But strangely enough, it’s not only here that there is a rush for “quick transition”. To be honest, I don’t know what “quick” means any longer! In some cases, some crossdressers I follow on YouTube or other social sites, after a year or two, aren’t crossdressers any longer: they have transitioned. Often it’s incredibly quick and unexpected — one day they’re talking about their latest set of clothes, the next day they suddenly decided to transition, and the day after that they’re already posting post-op pictures and videos of themselves.

Of course this is good! I’m envying them, not criticising! It shows a radical change from the experience I had a decade ago, where transexuals would spend years and years in suffering, and perhaps after a decade or two would then finally start their long transition process. Transexuals in the 1980s might only have become legal women by the turn of the century. That was what I was used to seeing. Not any longer! Nowadays, even more-or-the-less casual or occasional crossdressers seem to be able to get hormonal therapy, even if they don’t really want to do the full transition, but just look more feminine when dressing. A lot of couples, where the tolerant and supportive wife actually finds their crossdressing hubby “cute”, are absolutely fine with the changes — so long as they’re made with the overview of a doctor, of course — and this is becoming more common among the crossdressing community. It’s also not unusual for people to ask me online for how long I’ve been taking hormones, and be surprised when I tell them that I’m not on hormones at all. “Why not?” they ask in surprise. These days, the barrier between crossdressing and transsexuality has shrunk and faded. So-called “serious” crossdressers who search for a passable feminine image are “expected” to do some hormonal therapy and minor surgery, even though they wish to keep their day job as males. In Portugal, as said, you have all the options — going through therapy and change your legal gender; ignore therapy but still change your name and gender; or do both things if you wish — and this means that people are getting them.

So, well, this wasn’t a short parenthesis 🙂 But it should be enough to explain all about Patrícia’s decision and show that, nowadays, her situation is not that unique nor abnormal, but actually fitting quite well in the current trend. Patrícia really wants to pass. And if that requires hormonal therapy and minor surgery, so be it. She might have to think about her future career, and this might prevent her to become a full-time woman, but as she goes out passing as a woman for half the days of the week, she still wants to do a bit more than perfect her make-up (which needs little improvement) or her smart taste in clothing.

And she’s definitely got the experience. We crossdressers all know about friends who dress occasionally and have done so for years and years, but there is no progress in their techniques and style. They still pick up the wrong clothes for their figure, dress as someone twenty years older (or twenty years younger!), and either overdo their makeup or apply it completely wrongly. Again, this is not a criticism. As I told Patrícia last Thursday, my first sense of accomplishment came when I realised that I was better at doing my own makeup than my own wife. And while I don’t achieve salon-grade nails, when I pick up good-quality nail polish, I can apply it in five minutes without needing to correct it — a decade ago it took me hours and hours, as I applied it and removed it over and over again, and it never looked good enough. My wife doesn’t paint her own nails, but her sister does, and it’s with some pride that I notice that I can do a much better job than her. It has absolutely nothing to do with “talent” — I’m not artistically inclined, rather the contrary (my wife tells me that, thanks to my male genes, I can only “see” in 16 colours 🙂 ). But I have a lot of experience. My wife might apply makeup two or three times per year and doesn’t do the full routine anyway, because she has no patience for it. But I take less time and do it fully — because I practice every week. For years I avoided painting my own nails, so I just practised on fake nails and glued them on, but, at some point, I just decided to learn doing it on my own nails, until I was happy with the results. 15 years ago I needed to do the eye makeup over and over again until it looked a little better than something just out of a horror movie. Mascara would get stuck all over my face. Now I can apply liquid eyeliner with a firm hand, something which would be impossible just 3 years ago. I have less success with clothes because it took me years to find out what would fit my (enhanced) figure best, and that meant wasting a lot of money on clothes (my wife put an end to it; I’m not allowed to buy any more clothes for the time being). I still have some problems in figuring out what suits me. Coats and jackets, for example, are a nightmare to buy, and that’s why I have so few…

Still, I just do it once a week or so, so of course my progress is not that quick. Patrícia, by contrast, does that every other day. She has far more experience, acquired in just a year, than a genetic woman who might just get dressed for special events, like weddings and special dinners. She looks great with perfect makeup because she managed to experiment a lot. For months people have asked her if she is using her own hair or a wig, because it’s impossible to tell from the pictures (and you can stand just inches away and still have no idea). After all, nobody questions if Beyoncé, Oprah, or Tyra Banks are using wigs or not, right? They will refer to their own hair as “their own hair”… even if, technically speaking, it isn’t. But there is no difference… at all. Anyway, just another example on what you can achieve if you have lots of practice, and I really mean lots.

Going out that often also makes a whole difference to the attitude. Again, I have to refer to the example of genetic women. The average genetic woman who deals with a daily routine where she dressed casually (or business casual), wears flats most of the time, and goes to the hairdresser once per month or so, has a completely different attitude than some girl who dresses up every other day. You might have noticed how oddly these women are when they finally get to dress especially for an event. They don’t know how to walk on heels. They don’t know what kind of clothes flatter them — look at how they pick prom dresses for a cocktail party, for instance 🙂 They might not even know what hairstyle looks best on their face. They have no idea how to match things — not even the colour of their makeup with what they’re wearing. And I’m not even going to pick on women who paint their toes red but their nails brown… just because it takes so long to do their nails (or it’s too expensive to go to the salon) and don’t bother, since, most of the time, they won’t be wearing sandals anyway. Orange nails might look great on casual wear, but it’s horrible with formal dresses — unless they’re wearing an orange dress. It’s those small things that come with a lot of experience, and, to be honest, most genetic women simply don’t have that experience at all. They might do a professional makeover for a very special event — when they get married, if they allow a pro to “do” their outfit, they will obviously look at their best. But ask them to dress elegantly for a different event, on their own, and they’ll be clueless on what to do.

This shouldn’t be interpreted as boasting on my part. Let’s be honest: the pictures and the videos of myself capture me from “best” angles, and I don’t look nowhere as good as I sometimes seem. There is a lot you can do by capturing the camera angle just so to hide imperfections; I often reject a lot of pictures before publishing them. So don’t get deluded. I make a lot of mistakes and still have a lot to learn.

Quite a lot, in fact. I remember, not so long ago, commenting that I could remain on heels for as long as 10 hours or so, and my feet wouldn’t really hurt. Well, perhaps on very high heels, or on shoes that have a too-tight fit. When walking at home, I have a lot of confidence in my walking, and I’m aware I don’t do many mistakes — I look rather feminine when walking, and it takes little effort to properly walk.

But that’s just walking at home. Two weeks ago, after walking for about half an hour, I finally learned that I don’t walk that well on high heels (and I was wearing my most comfortable sandals). It’s not just the “hurting” — it didn’t really hurt, those sandals are great — but I just started losing a bit of my poise. I can guess that at the end of my stretch I wasn’t looking that feminine any longer. On Thursday I walked for an hour and a half, and I was quite conscious, when walking with Patrícia, how little experience I actually have — she managed to keep her feminine image all the time. I’m sure I was failing after 10 or 15 minutes, and, while paying attention to our constant stream of chatting, I had to remind myself that I’m supposed to be walking gracefully as well. It wasn’t easy and very likely looked quite artificial. Why? Because I’m not used to it — not for such a long time, out in the open. But I’m getting ahead of myself…

Maintaining a “perfect image” — which means enhancing one’s best features and downplaying the worst ones, while at the same time wearing something that is fun and fits one’s own image; you can have a perfect image even if you don’t have a perfect figure! — requires experience. A lot of trial and error. Even watching tutorials and looking at magazines is not enough: most of the women in them will not have your body and your figure, so the results of copying them just because they look gorgeous in their outfits just will make you look silly and ridiculous. But once you achieve that “perfect image” for your body type and your tastes it gives you a lot of self-confidence. That’s what Patrícia has: she knows she looks great — considering her figure and her tastes — and so she has confidence in her image. That allows her to project self-confidence, assurance, optimism, safety. What could someone like me wish more in a godmother? 🙂

When she told me that she would be willing to meet me at the oddest hours, just for a walk and a chat, while she’s having some days off — during which she can sleep until late — I was thrilled. Here was the goddess of crossdressing in my little circle of CD acquaintances who were happy to go out with me, just to give me a nice “push and shove” of encouragement. I felt I was not worthy of her kindness; after all, she’s enjoying those few free days, when she could be with her crowd of “professional” crossdressers — T-girls like her who go out every other day and look better in their outfits than any genetic woman I know, barring perhaps my mother-in-law… — but she was kind enough to spend a couple of hours with me on some remote place where everything was closed. That kind of helpfulness and selfishness is rather rare. I’m aware that the CD community is not so much different from others — there are golden hearts and rotten apples, like everywhere else. Obviously, I like to be attached to the few “golden hearts” I know, but I hate to intrude and ask them for some time for me — it seems selfish to do so. Patrícia could have gone anywhere else and had way more fun. Instead, she arranged to meet me near a beach where I live — usually a quiet spot, which I have driven by often, and even parked on the lot, noticing that nobody is ever around. Well, sometimes they have a van selling foodstuff and drinks which is open all night.

Patrícia, despite coming from much farther, arrived earlier than me. There were a few cars on the parking lot, and the food van was open, with a few late customers. The wind was howling furiously; it was not dreadfully cold, but it was certainly annoying. In typical Portuguese fashion, we kissed each other on the face, like good female friends always do in public (female friends and acquaintances never shake hands with each other; that only happens in extremely formal environments, like meeting a Cabinet Minister or something like that). What first astonished me about her was that she looks exactly like she does in the pictures. Unlike me, she doesn’t need any fancy lighting tricks or odd camera angles. That’s rather surprising: if you have met TV or movie celebrities in public, you will often be disappointed at how so much better they look on the screen. There are exceptions, obviously — and Patrícia is certainly one of them.

The second thing I noticed, after we decided where to walk — there is a small marina nearby, with a good sidewalk and plenty of light — is how much at ease she always is. Again, her long practice of going out so often showed me how fantastic it is when you actually know what you’re doing and how you’re doing it. It’s like when you learn to drive a car. You might remember when you finally got your license and started driving around on your own: you will be stiff, doing jerky movements, always focused on remembering everything you were taught during your driving lessons, and all your movements will seem artificial and mechanic. Then, after a few months of driving, you don’t need to think about them any longer — they become fluid, natural, and spontaneous. Well, that’s Patrícia walking around: she looks like she has been walking like a girl all the time since she was born. But that’s just the contrast between someone who has a huge experience going out and walking around like her and someone like me who was — literally! — taking her first steps.

We actually talked a lot about experience vs. intellectual knowledge. We obviously both agree that experience is far, far more important than knowledge. As said before, reading all the books on makeup will not give you an idea of how it actually feels to apply all those techniques on your own face; and the first time you do it on your own, it will seem to be impossible to replicate the smooth movements that actually get all the many pigments on the right spots. Even the best tutorial cannot convey to you the precise idea of how to actually do the makeup. So all this is pretty much worthless — unless you wish to write your own books and tutorials on makeup! — except, of course, as a reminder. If you have no idea about the difference between a concealer and a foundation, the best picture and the most accurate description will not help you at all. By contrast, if you have used both on your face, you’ll know exactly what each is supposed to do. And if you have experience applying them, you will now understand why the tutorials mention one or the other in certain techniques — putting into other words: those tutorials on makeups are reminders of what you’re supposed to do, once you have experience in doing so. Obviously, once you have mastered a few techniques, and experimented with them on your own face, you will find tutorials for new techniques easier to follow. A typical example: if you’re learning about applying eyeliner, the first time it will be impossible to get the pencil doing what you see people doing on the videos. You won’t have a firm hand (unless you’re a professional artist!). You will notice that eyeliners from different brands are harder or easier to apply, once you have bought a few; that kohl, for instance, is usually easier to apply but might give too dark results; while cheap eyeliner pencils might be too “hard” and thus not transfer the pigment easily. But once you’ve mastered pencils, you’re apt to learn how to use liquid eyeliner. It’s much harder to apply, but the experience gathered with using a pencil will help you a lot — even though, in the beginning, it feels like learning a completely new tool.

Patrícia and I didn’t discuss just makeup techniques 🙂 Actually, we didn’t discuss that at all. We talked mostly about her past experiences, and some common (Internet) acquaintances, and her forthcoming decisions regarding a possible transition. While we talked, we were paying attention to our surroundings. In fact, curiously enough, there were quite a lot of people around. Many more than it’s usually at that spot in the middle of the night! I had to admit that I was a little nervous, but Patrícia was confident — she didn’t fear anything, but didn’t try to “provoke” anything at all. There is safety in numbers, and while Patrícia is smaller than me, on heels I’m over 6 feet high, and that will make isolated individuals think twice 🙂 The few “night owls” around, however, didn’t bother us. Some were curious. They listened to our voices and knew we weren’t genetic girls. Most just spared a glance or two, and then just ignored us. So I didn’t have to run away like on my previous going out alone 🙂 — and Patrícia avoided larger groups, just to be on the safe side, although we kept a steady, casual pace, showing that we were clearly not interested in getting approached, but also unwilling to “run away” and spoil our own fun. I can only wonder what those people thought about us. I mean, if we were genetic girls in the daytime, we would just be two friends casually talking and taking a walk and smoking a cigarette or two. The “oddity” was being close to 5 AM and that both of us weren’t genetic girls.

This was also my chance to get some pictures taken by Patrícia, who is an amateur photographer and a perfectionist. Since it was horribly windy, and my own wig is really starting to show its age, I’m sure that I looked horrible — unlike Patrícia with her lovely hair — but she spared me the “worst pictures” and just sent a few that didn’t look half as bad. It’s been ages since I had been photographed by someone else — my wife did take a few pictures of me once, in early 2005, but I looked terrible back then. I commented that I would certainly love to do a photo session during daylight, having someone as talented as Patrícia to do it for me — but not on a windy day!!

Well, all good things have to come to a close. Since the sky was already showing the signs of a very early pre-dawn, I apologised, but it would be better for me to return home. Patrícia kindly obliged; in her neighbourhood, some people wake up really early, and she didn’t want to be seen by her neighbours like that, either. So we parted with some more face kisses as good friends 🙂

It was certainly an admirable day, worth remembering for a long, long time.

Thanks for making it happen, Patrícia! 🙂

[Edit: a few years later, I did the cartoon below, still remembering quite well this day!]

"Threats", a cartoon made by Sandra M. Lopes