Crossdressing Vacations!

Well, against all my previous pessimistic previsions, the crossdressing vacation went ahead. A miracle, for sure, but one that was quite welcome.

There were several moments where everything might have worked out wrong. For instance, as said, we got a voucher from my mother-in-law — but until the day before the trip southwards, I didn’t even know the hotel’s name, or if it would be a place welcome for crossdressers (not all are!). I tried to email them to ask, but the contact form on their website didn’t work. Also, my wife forgot to change the check-in date until the very last moment (she wanted to go the least number of days). Fortunately, it was still on time. We were set to go.

Nevertheless, it was just the day before the voyage that I told her (while she was in an excellent mood) that I wanted to get her to stick to her word, given 14 months ago, and allow me to dress during the vacations. She grumbled, but not really much. She just complained that we had to take another two bags with us (and she did rightfully complain about that, at least!). Ironically, I took the very same two bags that I used, twenty years ago, to “hide” all my crossdressing things… we have few suitcases and bags anyway.

The day we started the voyage was packing day. And here I expected the worst again: after a night’s sleep, my wife had plenty of time to revert her decision. She didn’t, but that didn’t prevent her from grumbling and rambling during the packing, with snarky comments all the way, and the evilest looks she was able to put on as if by sheer pressure of her discontentment she could persuade me to give up all plans. But, in the end, this would be seriously offensive for her own mother, who “sponsored” the stay and also to my own mother, who gave us the money for the voyage. So, in the end, she swallowed down her anger and frustration and reluctantly entered the car.

Algarve — History & Geography

A small parenthesis to give you some background on our destination. If you’re Portuguese or very familiar with the Algarve, you can skip this whole section; it’s boring. If you have no interest in its history or geography, you can also skip it, too 🙂

If you’re still here and reading this in Europe, it’s likely that the two only places you know in Portugal are Lisbon — and the Algarve as a touristic destination, even though half the Europeans will believe that the Algarve is in Spain. As a matter of fact, this region has been part of Portugal for 800 years — 400 years before there was Spain! It’s an ancient region — when the Romans came to invade the Iberian Peninsula, it already had thriving commerce between its city-states. In fact, even when the Greek, a few hundred years before the Romans, started to trade here and think about placing one or two colonies there, the region was already well-developed — and they opted for trade instead. Even more strange than that are some findings that show that the Algarve had an alphabet predating what later was known as the Phoenician alphabet (which inspired the Greek alphabet, which, in turn, inspired the Roman alphabet which we use today). It’s hard to go back 3000 years and figure out how everything started in the Algarve, but it’s pretty clear that at least for those 3000 years, there has been commerce between their city-states and the rest of Europe.

After the Roman conquest followed, and after a period of Christianity under the Byzantine Empire and the Visigoths, in the early eighth century, all these lands became Muslim, and prospered in a thriving civilization, still keeping relative independence, but of mutual assistance — and trade. This is why most cities still bear Arabic names (and why the Portuguese vocabulary includes a lot of Arabic words as well — not only guitar and alcohol but many in fact, to the extent that Arab speakers will understand a lot of Portuguese words, even if they might frown upon the accent). It took the Christians three centuries until they managed to conquer them back, which, as said, happened in the 12th century. Now due to a freak of geography, Algarve is bordered, in the north, by a ridge of mountains that keeps it pretty much isolated from the land beyond — a vast plain, dry and hot, called Alentejo, which goes all the way northwards to the Tagus river, where Lisbon is located, and even a bit beyond. This area always was very sparsely populated — even today. Climatically, the Algarve is more Mediterranean in nature (while the rest of Portugal is mostly Atlantic) — warm and sunny, but with plenty of rain coming from the southwest and getting trapped by the mountain ridge, and thus providing very fertile land on the higher ground. The southwards coast, of course, is where the many beaches are — almost 150km of coastline, interrupted by exquisite rocky formations.

But due to the distance to the capital, Lisbon — Alentejo has just three important cities (even though small ones) in an area as large as Switzerland or the Netherlands, over the centuries, the Algarve became an impoverished region — losing all importance in terms of trade as it happened before the Christian reconquest. It enjoyed a period of wealth and prosperity during the Discoveries — Lagos and Sagres, on the western side of the Algarve, were the first cities from where the Portuguese explorers went to discover the whole world. After a few decades, they lost importance, as Lisbon provided a much larger trading port (and better control of taxes and fees imposed on commerce!). So for most of Portugal’s history, the Algarve was a backwater, too far away from everything, and surviving on its own thanks to fishing and agriculture.

All this changed in the 1960s. The British, who always enjoyed a close relationship with the Portuguese (although often one-sided) since they lent support for the Christian Reconquest in the mid-12th century, now found this remote location, away from everything, with its lovely beaches and warm climate all year round, and no tradition of tourism whatsoever. Perhaps to the surprise of the inhabitants, they started to settle there with their villas for the vacations. In those days, there was literally nothing — fisherman villages, tiny cities which didn’t even have supermarkets, no attractions except for cultural heritage, bad roads which took all day to travel from Lisbon, and just one very old train line which was hardly planned to manage the extra passenger load during the vacations. There wasn’t even more than a few restaurants and absolutely no bars, clubs or discos.

The British soon started building not only villas but even small resorts, with willing town halls eager to get hold of some taxes. One of these resorts even hoisted the Union Jack, which — during the times of the Portuguese dictatorship! — was not seen as a bright move. Still, the relatively mild authorities, the wonderful weather, the unblemished landscape, the cheap prices of everything, and the simple but delicious food captured the attention of the Brits. They soon started to “colonize” most of the Algarve, bringing in their own pubs, their scuba diving schools, and even some lawyers to aid prospective buyers to celebrate building contracts and property sales. The natives saw all that with mild curiosity. Remember, these were the days before rampant hooliganism and violence in Britain, and, as said, the Brits always enjoyed a good reputation throughout Portugal. They have always been very well established in Oporto (owning, at the time, most of the Port Wine brands) and Lisbon, where they have been merchants for 6 or 7 centuries. There are still family names of “Lancastre” and “Burmeister”, corruptions of ancient English names, from families established here centuries ago. But even in our modern times, the British immigrants are among the largest group living in Portugal. They’re closely-knit, very easy-going, mild and peaceful, and quite well tolerated. The Algarve was a novel destination for them, of course, and the idea of establishing tourism there was quite odd (compared to other touristic spots, like Estoril or the Island of Madeira, which have British residents since the mid-1800s and a continuous stream of tourists since then), but they got well along with the locals.

Who, of course, didn’t mind a bit extra cash, in what used to be Portugal’s poorest region. Soon the locals found out that the British loved the simple cuisine, and started building restaurants on their own, which, in turn, compelled the fishing industry, as well as the agricultural produce away from the coast, to increase to sustain the growing demand. In 1965, Faro, Algarve’s capital, got an international airport, since slowly the increased traffic from tourists could certainly support it. Today, even though Faro has little more than 60,000 permanent inhabitants (a tenth of the people living inside Lisbon city; sixty times less than the Greater Lisbon area!), the airport gets over 5.5 million passengers annually (besides the many tourists which prefer to fly to Lisbon and take a bus, a train, or rent a car — and the many who simply drive there coming from elsewhere).

The massive influx of tourism pretty much changed everything, dramatically so. Besides the British, Germans and Dutch are among the main group of tourists in the Algarve, and it became even a major vacation destination for the rest of the Portuguese. To accommodate all those people, whole neighbourhoods were created from scratch — with the many hotels and resorts popping up accordingly — but it was mostly unplanned and chaotic. Greed made the town halls pretty much accept any project, so long as it brought in the much-desired money. By the mid-1980s, which I remember quite well, everything seemed to be falling apart and bursting at the seams. Water and power, designed for a small population with little or no industry, now had to deal with the insane amount of temporary residents during the summer — and hotels and golf courses required everything and much more. The old road system had traffic jams of perhaps 50 km for hours and hours, which, taking into account that the Algarve was about 300 km away from Lisbon, it was very messy — we’re talking about one-lane roads with poor pavements across the hottest and driest plains of the Alentejo, with few villages spread around. The single-track train line was not even electrified and could only handle a small amount of traffic; a trip to the Algarve from Lisbon required taking a boat first (to cross the Tagus) and slow progress and a change of trains, with lots of stops as trains waited on the single-track line for a crossing. By car or by train, a voyage would last perhaps 8 hours — coming finally to busy conglomerates of high-rising towers covering the beach, with brownouts and failing water supply. There was only one main road crossing the Algarve from east to west, and it was permanently congested, from early morning to late night, as locals and tourists struggled to move between towns. And while the first supermarkets started to appear by the mid-1980s, the distribution of food and supplies to them would often be insufficient. Even though most people in the 1980s could afford to stay a whole month in the Algarve it could mean facing a shortage of pretty much everything. And still, people continued to come.

The locals are quite “creative” in the way they handle business, and a lot of tourist traps — from restaurants to fake souvenirs — quickly started to appear pretty much everywhere. Prices rose to crazy levels, compared to the rest of the country, because most people in the Algarve would only need to work for three months, during the summer, and pretty much wait 9 months until the next batch of tourists would come in. That meant squeezing tourists dry as quickly as possible; saving as much money as they could; investing in more restaurants, more rooms, more little shops, and so forth. While this mimicked pretty much what happened all over the world in places which suddenly became tourist attractions, what was more noticeable in the Algarve was the utter lack of planning and the complete chaos of the development.

Still more people came, and enjoyed everything.

Not all locations in the Algarve suffered the same way. By a stroke of luck, my own parents favoured a town in the west of the Algarve, Lagos, which escaped the worst nightmares, since it’s rather windy compared to the central and eastern destinations, and, as such, didn’t manage to attract tourists in search of hot and dry weather. There, for a while at least, some urban planning was possible, development was at a steadier pace, and the infrastructure managed to grow a bit better. Not perfectly so, of course, since much of the infrastructure is shared. For instance, the power system would also have shortages, as the central areas of the Algarve would pull much more power due to higher demand, and leave the less important towns in the dark — and without water, too, since the water pumps need power to operate as well. If the roads towards the centre of the Algarve were already congested, then the people wishing to go further on would even have longer waiting hours. I remember in the late 1970s that there was no bank in Lagos; my parents had to drive to the neighbouring town, Portimão, which is about 20 km away, to get some cash. This would take them all morning.

The flip side to that chaos is that it did, indeed, bring in the much-needed money, and today, the Algarve has the third-largest per capita income in Portugal, next to Lisbon and the Island of Madeira. With that money, some planning could go ahead, and this finally solved pretty much the major issues. Nowadays, the distance from Lisbon to the Algarve was shortened by about 50 km, thanks to a straight highway which goes directly to the centre of the Algarve, and you can do the journey in 2 1/2 hours without breaking any speed limits. New bridges and re-pavement of the old roads means a lot more alternatives to cross the still desert Alentejo; the train service was completely refurbished in the 1990s with higher-speed trains which take pretty much the same time to do the whole trip, and now they cross the Tagus river on a bridge. On the rare occasions that I go to the Algarve on business, I prefer to take the train — it’s much cheaper, far more comfortable, and there are a dozen trains per day. There are no more water or power failures; many new roads and highways were built to connect all cities in the Algarve with good connections. In fact, these days, spending your time in the Algarve means not staying at the same spot. Rather, people usually follow a routine of driving around most of the cities just to find things they like to do — the tourism offices are very well coordinated and you get to know what’s happening all over the Algarve. The airport, which is located in the middle of the Algarve in Faro, is, at most, about an hour’s distance of travel to any location — which also means that driving over to the next city takes little time. Obviously, this is less true during the summer — but still, traffic jams on the highways are unheard of. Parking places are a problem, though!

Decent urban planning tried very hard to revert the effects of the late 1970s and 1980s, and to a certain degree of success. You still get whole neighbourhoods of the ugliest possible buildings, since they are there to stay, but at least now they’re surrounded by gardens, golf clubs, well-paved streets, and good access to all kinds of facilities, from restaurants to convenience stores, to clinics, hospitals and pet grooming shops 🙂 Unlike Spain, where every town is teeming with activity — nightclubs, bars, and all kinds of tourist attractions — the Algarve tends to clump these together in certain spots (except for restaurants, which are everywhere), but since it’s so easy to travel among these places now, it makes little difference. And for the ones desiring a more sedate kind of vacation, slightly further away from the busiest towns, you get golf clubs, luxury villas, and VIP resorts, in the middle of the countryside — but with easy access to everything else. And, of course, there is still the mountain ridge — a completely different landscape which has nothing to do with the sunny beaches, and which is practically unblemished and untouched by rampant tourism. And for the ones who enjoy cultural tourism, most of the cities still have large historical centres, like Tavira, which is a monumental city full of 17th and 18th-century palaces and churches.

Personally, I would flatten whole neighbourhoods and rebuild them from scratch, since they’re an eyesore and a blot in the landscape 🙂 It’s too late for that now. However, there is a completely new town, Vilamoura, which grew out of nothing and was planned as a whole town from scratch in the 1990s. It’s a luxury destination, and, even though it lacks the taste of antiquity from the old towns with their medieval and Muslim street layouts — even today, there is still a lingering taste of the bazaar-like culture so popular in the North African Muslim countries, even though stone-and-mortar shops have replaced tents and makeshift places of commerce — Vilamoura is a pretty good example of how good urban planning can be implemented, provided the money is not an issue and there are no pre-existing ugly buildings to deal with. Others, however, might prefer the simple charm of old fishermen villages and their lack of sophistication; in fact, for over 30 years, that’s where my parents would prefer to spend their vacations.

So this should give you a good picture of what was ahead for me. I will just add something that a CD friend pointed out to me, and which my own wife also noticed. The Algarve, even off-season, is always a very mixed environment. A third of the locals are obviously Portuguese; but the remaining come from all over the place, mostly from Britain, the Netherlands, and Germany. As a 1.78m tall crossdresser with reddish hair, I don’t look so much out of place — half of my genes are German anyway. Locals like foreigners, because foreigners mean commerce. Even though I wasn’t very aware of that before my trip, it soon became apparent that most people doing business care little about who you are or what you do. So long as you’re there to fill their pockets, and you’re not actually disturbing the peace, they will accept you. And they are used, for over a generation at least, to deal with all kinds of freaks — and don’t mind them in the least.

Arrival — Day One

To put things into context, it’s better to start with a map:

Beach at Albufeira
One of the beaches in Albufeira (source: Wikipedia). This is in the summertime, of course 🙂

My “home location” for the vacations was in Albufeira, at a nice, 3-star apartment hotel, the Pateo Village. This was actually rather lucky: for my wife, it meant having a kitchenette, so we could save on food costs by cooking at the apartment. For me, it meant free access to the outside — we were on the ground floor, which opened to a pavement leading to the parking lot. This was a low-cost apartment hotel: the whole staff consisted of one person at the reception desk (they seemed to have three persons doing 24-hour shifts and rotate every day) and a cleaning team (probably outsourced). While the reception was in a good location to spot who would walk the short side-street (closed to car traffic) and go in and out the 3-floor apartment blocks, it didn’t force anyone to actually go through the reception, but just pass in front of it from the outside. Perfect!

Actually, to be honest, on the first day I did explain to the boy at the reception that I liked to wear women’s clothing and that he shouldn’t be startled if he saw someone he didn’t know walking around — I promised to be discreet and not to attract undue attention. His reaction was an indication of what would be ahead: he didn’t mind in the least. Note that this isn’t an LGBT-friendly hotel. I didn’t even get a snarky comment or a joke, not even a surprised look. Rather, he just said, in a very professional way, that it was “absolutely all right”, there would be no problem at all, and that I should be fine doing whatever I pleased. This startled me a bit — clearly, I wasn’t the first crossdresser to use that hotel, or, if I was, they were well aware of crossdressing (probably exchanging comments with colleagues on other hotels or even — who knows? — from information spread by the Tourism Board). Whatever the reason, there was no surprise, no limitations, no comments, nothing. I was quite pleased!

Unfortunately, he didn’t pass the message along to the other employees (even though I asked him to do that), which created a few embarrassing moments. Or perhaps he did. But I’m anticipating the rest of the story.

We had arrived at around 6 PM, and we still needed to buy some food at a supermarket, so, even though I was tired from the voyage — it wasn’t that long, but I get always tired when driving — I just started to dress at 8 PM or so.


It was a Saturday — it’s been quite a long, long time since I last managed to dress on a Saturday! — and, even though we were at the lowest possible season, surely things must be open. The locals, after all, have to enjoy themselves somewhere. In my teens, Albufeira was famous for its nightlife, so I was wondering what I could find. So I grabbed the location for an LGBT-friendly bar from the ‘net and was wondering if I could find it (and if it was open).

Unlike what happens at my place at home, my wife was quite willing to “let me go” much, much earlier — I believe it was not even 1 AM yet. Deprived of her gaming computer (which is a desktop computer!), she was left with some books (and on Sunday she started to watch TV instead), and, to my astonishment, she didn’t raise any complaints about going out “so soon”. I guess that the main reason is really that nobody knows us here, and I told her that I had warned the reception guy. Who, as it turned out, didn’t even watch me walking out of our building and pass in front of the reception.

Then I drove down to the old city centre. Unfortunately, pretty much everything was closed. I drove around – traffic is insanely complex, in those cities with narrow roads and ancient medieval/Muslim grids — but couldn’t find anything open. Even though I parked a bit away from the centre (which is closed to pedestrian traffic only), and walked a bit, there were only suspicious characters around. Now, this came to me as a surprise: even though it was not very late (for a Saturday night!), there were few people around, and all of them looked like ex-cons or Mafia operatives.

All males, too — there were no women around. And they ganged in groups. Scary! Mind you, I only know the Algarve from my summer vacations in the youth, and even though I’ve spent a few nights there not so many years ago (yes, even doing some crossdressing — twice, if I remember correctly, on a neighbouring town which I visited on Day Three), I had a completely different idea of the locals. The Algarve has a good reputation as a relatively peaceful area with little criminality. Mind you, just because someone looks like they have raped and murdered a victim across the corner and is wiping their blood-dirty hands on their jeans, it doesn’t mean that they are criminals 🙂

But that was the strange impression I got — that after midnight, only the rowdy and rough elements of society prowl around, ganging together and looking for mischief. This made me reflect a lot during the next few days, but at that moment, all I thought was that this was not exactly what I had in mind!

So my next step was to drive around the neighbouring beaches and localities. I recollected from memory a few spots — all by the beach — where I was sure there had to be some nightlife. Even though Albufeira is not a huge city, it’s dead centre in the middle of the Algarve and attracts a lot of tourists — they surely have to go somewhere. And, in fact, they did — the clubs, bars, and entertainment spots moved to the adjoining beach, Praia da Oura, completely filling a street renamed by the British residents as “The Strip”. And here I found gazillions of people!

Nightlife in Oura - The Strip
“The Strip” at Oura, by night (source: Wikipedia). Not one of my pictures. But it looked pretty much like this on Saturday night!

So many, in fact, that parking was impossible, and this was pretty much the opposite of what I wanted. Too busy! Too much exposure! I just enjoyed driving very, very slowly and being watched — while I was safely inside the car. But clearly, this was more like it — a relatively public, safe area, with “normal” people, half of them locals and the other half tourists, and people of all ages. I’d certainly not look outrageous out of place there!

However, of course, I had no idea if these places would enjoy crossdressers (on the following day I looked up an LGBT-friendly spot at “The Strip”, but it was so tiny that I never managed to locate it). So I drove on around the neighbourhood — outside “The Strip” there are plenty of places around, which are far more peaceful — and found a potential café with an outside esplanade which looked “safe” enough, drove a bit more until I found a U-turn, and parked nearby. Just my luck: on the parking lot there was a pesky dog who was barking at everyone and calling undue attention. And, worse, the parking lot was in front of a hotel, with people coming in and out all the time! Again, this was too much exposure for me.

So I gave up — I wasn’t feeling too confident by then — and just continued to drive around. It was a very foggy night, but in spite of that, I managed to visit a lot of neighbouring villages, in search of potential locations for another day.

In the end, I drove back to a viewpoint near the hotel; there really was lots of fog, so I walked around, had a cigarette, and went back to the apartment.

My wife was still awake, she made no snarky comments, and was getting ready for going to bed. I still lingered around for a bit and had some time to do a short video, which worked rather well, considering that I just had my laptop with the terrible webcam. But the lighting in the apartment is far better than what we have at home, so the result was not too bad, even considering that the upwards angle isn’t flattering:

Then I proceeded to undress, but I didn’t do it fully — I kept my nails painted (I had them grown very long!) and the breast forms glued on, as well as all my tape tricks for the extra cleavage and so on. My point is that this would give me an extra half-an-hour of sleep and set the stage for a special request to my wife.

Day Two

The special request was simple: I wanted to go out fully dressed in bright sunlight. Since we had gone shopping for food already, the next days would be mostly about sightseeing. My wife, if you recall, suffers from several chronic diseases, including fibromyalgia, meaning that she can’t walk around for long — two hours is pretty much her limit, leaving her absolutely tired and hurting all over. So I thought that just because of those two hours it would be pointless to insist on wearing male clothes; I could crossdress the whole day. We would not even be seen much, and always in different places anyway. This was good, sound logic, but my wife didn’t agree with me. Her argument was quite solid: she’s the kind of person who hates to draw attention. This is the main reason why, although at some point in the past she insisted otherwise, she doesn’t want to go out with me. As she so well pointed out, a redhead over 1.80m tall (on heels) attracts attention; her own words were: “you’re BIG everywhere!” So, no matter what I do, or what I wear, I will still draw attention; and, of course, on a second look, I immediately get “read” as a crossdresser — which will obviously draw even more attention. And that’s what my wife wants to avoid at all costs. Putting it into a different perspective: it’s not because of me as a crossdresser; it’s because of her who wants to go unnoticed and in peace.

Well, I can understand and respect that. So, well, I condescendingly agreed to stick to crossdress by night, and do some sightseeing with her by day. By sheer luck I did pack two male tops, a pair of male jeans, and a pair of male shoes in our luggage — because, in truth, I was not expecting to wear anything male in this trip. But I thought that at least on the long drive southwards and back, to eliminate any potential troubles (e.g. police stopping me), I ought to be in male attire, thus I had some male clothes with me.

Vilamoura - Crowne Plaza and Casino
Vilamoura is a planned city, it looks lovely, even by night! (source: Devaneios de Vida blog)

Anyway, Sunday was St. Paddy’s Day, and I forgot to mention that there i

s a rather largish Irish community living in the Algarve as well. So, even though Monday would be a working day, I was expecting many pubs to be open, full of crazy Irish celebrating their favourite saint, and the many locals who join them in the boozing 🙂

Because of that, I picked for my location Vilamoura. As said, this is a rather fancy town, so I was hoping to get a less rowdy crowd, while still finding open pubs and bars. Vilamoura also has a Casino, which often means that bars are open until 3 AM, for the visitors who want a quick snack after losing all their money and not being able to afford it inside the casino — just like near my place at home.

Vilamoura is not too far away, and the roads were completely empty. When I spotted my first open bar, I parked nearby and took a picture at the parking lot. Time to go out and walk a bit on a chilly night!

I have to say, I walked quite a lot, and almost bumped into two guys in a garden. By then I had to change my mind regarding the kind of people that were around. At first, all I could see was the same kind of rowdy, dangerous-looking types that I had seen in Albufeira, walking in twos and threes and looking mean and tough. Hm. I wasn’t being very lucky, or perhaps I was developing the habit of being afraid of everybody! So, in the end, I just walked in my heeled boots in front of that bar — with lots of people, they all saw me outside 🙂 — but didn’t walk in. I passed a relatively calm restaurant with elderly tourists inside, some of them raising their eyes in my direction, but not really taking notice of a tall redhead walking around.


In fact, close by, I watched a guy peeing on a wall, which is rather unusual in Portugal, much less in a fancy town in the Algarve. Well, clearly people were drinking too much, and that meant they would be more likely to take a fancy to a strange-looking guy in women’s clothes, so perhaps my strategy hadn’t been very clever. Who wants to be around mean-looking drunkards wanting to have some fun? Not me!

So I drove on to a parking lot near the church — I had spotted what seemed to be a disco nearby, and this time, the kind of people who were on the street seemed much more “normal” to me. There were even a few women in small groups. I walked a lot in that neighbourhood but couldn’t exactly figure out where the disco’s entrance was. And I was getting reluctant to be so far away from the relative safety of the car, which was parked in an area without a single person in sight. So, once more, I took fright — again — and just returned. By chance, I saw another group of people walking around, so, clearly, this spot was not so deserted as I thought, but still too far away from everything to make me comfortable about walking alone on the streets.

By then, it was clear that I was facing a dilemma. I didn’t feel enough confidence in the middle of huge crowds of party-going people, where there is safety in numbers — I guess I’m not ready for that yet. Small groups of people seem to be better, but not the kind of groups that seem to have come out of the nearest prison. Curiously, most of those types I saw around were all tall, bulky, well-muscled, and nasty-looking. Maybe these are the only people who feel safe to walk around in the Algarve during the night? Where were the normal-looking youths, the women, the skinny types, the cool, easy-going guys? Apparently, they stay at their homes and hotels and sleep. And, finally, the total absence of anyone around is frightening — especially if you’re aware that only the mobsters seem to walk around, and who knows who is lurking near the next corner? During all these nights, I never saw a policeman on duty…

So I drove back, a bit disappointed, but still happy to be able to drive and walk around. Gas was running low, and I was also short on cigarettes, so I decided to be bold and drive to the next gas station. Now, if you follow my blog, you know I have used gas stations before — many are automated during the night, so there is no need to interact with anyone, and I usually pick the ones without anybody around. But this time it was different: to buy cigarettes I would need to talk to someone. Yay! My first physical interaction with a fellow human being while crossdressed! (well, except for my wife and meeting Patrícia Coelho, of course)

Ironically, the gas station I picked had a problem with their connection and the money network was down, but I had enough cash to be still able to buy cigarettes. Also ironically, the debit card I have is from my mother, who, as said, “sponsored” the trip, so it has a female name on it, which should be interesting to see if it would raise any comment from the attendant. It was actually fun! Of course, I’m sure that I don’t pass. Even though thanks to some amateur vocal training, I can disguise my very low male voice to a degree, it’s far from “passable” — and no, I don’t need to go into a falsetto, which is way more noticeable. It’s just a trick of letting your voice come from your head and nose instead of from your chest; it takes some training, and it will sound metallic, but it will definitely sound different — not quite male and never quite female, but something in-between, like a middle-aged housewife who is on 2 packs a day. Which, well, is not really much different from what I look like 🙂

Even though it was quite clear that the guy at the station immediately knew who (or what) I was, he didn’t make any comments. In fact, he was helpful and chatty, explaining that the money network was down since midnight (it was 2:30 AM by then), and even though I was willing to give it a try twice, it didn’t work. So I just bought the cigarettes. No comments whatsoever, no grinning, just a serious business transaction.

It was really, really a great experience! It just reinforces my idea that people who are doing business don’t care about how their customers look like. They are just friendly and happy you’re willing to spend some money. Maybe this guy had a nice story to relate to his wife when he returned home — or maybe there are so many freaks in the Algarve that he has long since stopped to bother. He didn’t even goggle my awesome cleavage, that’s how professional he was.

Albufeira Marina
Albufeira Marina by day. Notice the crazy architecture. (Source: Wikimedia Commons)

When returning, instead of driving directly to the hotel, I decided to go a few extra kilometres to take a look at the Albufeira Marina. This is a relatively new marina, which features post-modern architecture from a famous Portuguese architect, known for his pop-art inspired buildings, which I personally find deplorable — but, alas, art is art. My point is that marinas tend to have bars open by night, and, at that hour, they might be quiet enough.

It was too quiet.

Access to the marina is a bit weird. The parking lot is some 10 metres above sea level; so you have to take one of the many stairways down to the bar and restaurant area. This is scary. The stairways are very high and quite narrow; while they’re well lighted, they don’t offer good visibility and seem to be rather constrained — you don’t feel safe. Especially when there was nobody around. I still walked down one of them, verified that none of the bars and restaurants was open and that everything was silent, and then quickly returned to my car. The only vehicle in sight was the garbage truck. Definitely, this was another dead end in my plans of finding a safe place to have a drink while crossdressed…

So I drove back and parked on the hotel’s parking lot, and here I had an unexpected surprise. This night, there was a different shift, and a different attendant, who came out to see who had just arrived. Clearly, he hadn’t talked to his colleague. So he came out to meet this unexpected visitor with some curiosity. Well, I nonchalantly gave him a bright smile and wished him a good night (to which he responded in kind) and walked back to our apartment. Whew!

My wife was still up and talkative, so I had no opportunity to take any pictures or do any videos. I just went to bed after undressing.

Day Three


After a good night’s sleep and some reflection, I figured out that I had to re-evaluate my choices when going out. The first thing I suddenly realized is that, even in spite of my born gender, and my relative height and size, the truth is, I was fearing lone strangers by night — while dressed as a woman — because, well, women, in general, fear those strangers as well. And one thing is a woman that might become a target of some rude guys just wanting to have some fun, but not having any real ill intentions beyond some flirting. The other thing is that same guy hitting me instead, suddenly realizing that they’ve picked the wrong kind of woman, and becoming violent and very angry for the delusion. So, well, this told a lot about myself: I’m not as bold as I thought I was, and walking around in complete isolation was something that made me seriously uncomfortable. On the flip side of the coin, I still don’t feel comfortable being around a lot of people. The ideal situation seems to be something in-between. I have proved to myself that I have no issues talking to gas attendants or hotel employees or whoever else, so long as I don’t feel threatened. I have some qualms in entering a straight-only bar who might take issue at having a “strange” customer there, who might make other customers leave; but I have no problem in entering a shoe shop for women and looking for shoes big enough for me, for example. So I gave this some thought, and I decided that the best, for now, was to go to an LGBT-friendly bar.

After a few searches, I decided to go to Lagos, a 45 km ride away. Now I’m quite familiar with Lagos; for over three decades, my parents took me to spend there at least 4 weeks per year with them — in some years, over six weeks. It’s a very quiet town and one that took more time to attract the massive tourism more typical of central and eastern Algarve, since the west is windier and the seawater ice-cold, due to the stronger Atlantic influence (the East is much more influenced by the hot Mediterranean waters). As said, I also occasionally spent some vacations there on my own, and even did some crossdressing there, well over 15 years ago, but never dared to leave the hotel. There is a relatively small nightlife area, most of it quite well-known to me. I know most of the streets and places, at least in the older parts of the town, which would add to my sense of security. And if most of the Algarve is relatively criminal-free, Lagos is even more so. All good reasons to drive over there, even if it meant a longer trip — taking about an hour — and a shorter time to enjoy myself. And, yes, there seemed to be an LGBT-friendly bar there, with a rather sophisticated environment, which perfectly matched my own style and taste of bars — more in the line of a quaint English club by the seaside, instead of a loud nightclub. So I decided to give it a go.

When stepping out around midnight, the same hotel attendant from the last night came out to look at me, but this time, I ignored him. I just let him think whatever he wanted. If he talked to his colleagues, they would tell them about me; I wasn’t worried.

Lagos by Night (author: jotamyg)
Lagos by night. Source: jotamyg

Since on the night before I didn’t manage to refuel (because of the money network issues), this time I had to stop at a gas station. This time I was even more confident. I had to wait, though, the attendant seemed either to be asleep or busy at the toilet. I tapped on glass several times and patiently waited. He eventually came out of his hiding place, smiled at me, probably thinking first that I was a female customer, but then realizing his mistake. Still, he was all professionalism, even though it was quite clear that he was enjoying himself — but did not betray himself at any moment. All went well, very professional. I enjoyed that.

Now from the map location for the bar, I had a pretty good idea where the bar was, so I sort of semi-automatically drove through the usual streets. You know how it is when you know a city well; you remember all the places to turn left and right and don’t even think twice about it. There was a catch, though, something I wasn’t aware of. Apparently, the town hall decided to turn the whole of the old city centre into a pedestrian area, with car access only to residents. A good move, of course, but it meant walking quite a lot. And I then noticed that I was at the wrong spot. Lagos has a large part of the old medieval stone wall still standing, and the streets go through some of the old gates. I was at the wrong gate, just outside of it, where a parking lot had always existed. I just realized that when walking out of that parking lot and consulting a huge map posted there; I should have taken a different road and picked the southwards gate instead. Well, it would be a long walk, but not terribly long, and I might have done that, if, by coincidence, a lone drunkard with the physics of a bodybuilder hadn’t suddenly appeared and taken a huge interest in me. Fear grabbed me, and so I returned to the car, thinking that I might attempt to go to the other gate, which would be much closer to the bar. And that other gate had an even larger parking lot and was closer to the centre, so probably there might be a bit more people around.

Unfortunately, Lagos had grown and improved their city facilities since the last time I was there, three years ago. What used to be a surface-parking parking lot just outside the gate was now turned into a commercial, underground parking lot, with a huge garden planted on top of it. Nice, of course, but the parking lot was closed. Ugh. This meant parking a whole street away from the gate and walking all the way down. And that was an absolutely empty street with bad lighting. Worse than that: there was one rowdy bar with two guys there, who immediately came out to watch me as soon as they heard my heeled boots hitting the cobblestones on the pavement. I still considered my choices: it would be a 5-minute walk on a deserted street with those guys behind me, and who knew what happened next until I found the bar? After all, the bar could be closed; it was a Monday. And it meant walking back all again, all alone, through all these empty streets. Once more, I chickened out and decided to turn around and give up on Lagos.


To make matters worse, on the return trip, I took a wrong turn, and lost my way, drove in circles through completely empty neighbourhoods of tourist villas. All of them completely unknown to me: they are relatively new neighbourhoods, built relatively recently, and without any street signs whatsoever. Gosh, I was getting quite frustrated! And this in a town I was supposed to know quite well! It was quite ironic. Even if I wished, there was absolutely nobody on the streets that I could ask for directions. Lagos is definitely a dead town in mid-winter, outside the season, even though it wasn’t so late yet.

Eventually, I found my way and decided to take the national road to Portimão, which is the next town on the road back. Portimão is the third-largest city in the Algarve, and, even though it’s on the less touristic Western Algarve, I imagined that it had enough of a nightlife — it certainly does during the summer. On an impulse drove on to Praia da Rocha, which is pretty much in the outskirts of Portimão, and which used to be one of the loveliest beaches in the Algarve, until rampant urbanism completely destroyed its exquisite beauty. Still, with those buildings came one strip of bars, discos, and nightclubs, so I thought it was a safe bet.

Unfortunately, it wasn’t. There were very few people around, everything was closed, and I just found a dozen of teens in front of what seemed to be a bar just closed. Bummer! It was getting late, and I still had a long drive back, so I just parked at a round plaza, walked a bit, and took a picture.

It started to rain. There was nobody at the hotel looking me up, and my wife was still awake, but she soon went to sleep, so I had some time to do another video:

Day Four

Final day! A bit frustrated about the last day, I looked for another LGBT-friendly bar in Faro — which is nearer to Albufeira than Lagos, and, Faro being the capital, there was a good chance it was open. Unlike the rest of the Algarve, Faro is not really a tourist city. While it’s very quaint in its own way — a nice province capital — it’s the place where you have all the services, the banks, and commerce. Obviously, there are plenty of hotels, and a few nearby beaches, but even during the summer, the resident population is what supports the city, not necessarily the commerce. While I had just been once or twice in Faro around the nightlife areas — there are two, inside the castle walls, and on the old town centre — not being so keen about nightlife overall, they were not that familiar to me. And even though I have been to Faro several times on business trips, I cannot say it’s a city I’m well acquainted with. Certainly not as much as Lagos for sure. Still, I would say it’s the second city in the Algarve that I’m more familiar with; at least its traffic around the city grid doesn’t hold many surprises to me. So I was a bit more optimistic.

This time, once more, I was watched very closely by the hotel employee assigned to the night shift when leaving the apartment — this time, a woman, who I had not met before. But she didn’t say anything, she just came out to watch me enter my car and drive away (On the next — and last — day I made sure I thanked her for the stay, and I was not sure if she figured out that I was the “woman” she saw the night before or not. Perhaps she had already talked with her colleague. Or perhaps she didn’t. She was definitely quite professional saying good-bye.).


Reaching Faro, I looked for the first available gas station which had the lights turned on, but found out that it was closed 🙁 Oh well, I still had enough gas to do the trip back if there was a need. But at this time, I wasn’t too worried about gas stations any more.

Heaven Club in Faro
Sandra at Heaven Club
Clearly not my best shot, specially from that angle. But it’s hard to take a picture with my old phone’s camera. At least I got a Buddha on the picture as well, which must be auspicious somehow!

It was relatively easy to find the bar — the Heaven Club. I drove around in search of a place to park; unlike the other cities I’ve been to during all these nights (except for Oura), there was a decent amount of people around, looking for the local nightlife, even on a Tuesday. And at least they looked far more “normal” — women would be walking on the street, even by themselves, which was definitely a good sign.

After half an hour, I luckily found a parking spot just across the bar. No need for walking around half-empty streets with lurking criminals! (Not that I saw any, of course). I just stepped out of the car, walked across the narrow street, and entered the place.

The bar was open, but I was the only customer! Well, it’s a tiny place. Not very fancy, except that their idea of “heaven” is not Christian heaven, which definitely would be lacking in LGBT people. Instead, they opted for a design in black and silver with Buddhist statues on the niches on the wall. Definitely an auspicious sign. And, curiously enough, it’s being run by a couple. Well, or at least they looked like a couple: the bar attendant and a gorgeous blonde who just sat at one of the tables, both having fun on Facebook on their laptops. Things definitely changed quite a lot since I used to go out to bars with my friends!

I asked if there were any shows tonight, and they politely explained that they only have shows from Thursday to Saturday. Just my luck! I should have planned my night travels differently, and start with Faro first. But obviously, I was quite welcome to a drink. At least it was clear that here they had absolutely no problems with transgendered people; you can see the pics from their parties, they have all kinds of people coming there. In a sense, they treated me so “normally” that it was a bit confusing. Maybe all LGBT bars are like that — they make you feel comfortable, no matter how you look like. I suspected that the couple was exchanging some messages on Facebook about me (the blonde bombshell was certainly giggling), but, on reflection, it’s hardly probable — this was an LGBT bar with regular shows, thrice per week. They were certainly more than familiar with crossdressers.

The truth is, there was not much to do, except to play around on my own smartphone, have a drink, and smoke a few cigarettes. I’m not a dancing person (ironically I spent years learning ballroom dancing, though) and it would feel weird to be the only person dancing, anyway. This was more a nightclub and not really a bar, so they didn’t offer to make small talk, even though the bar attendant was extremely polite all the time. Some of you, used to British pubs, might have expected bar attendants to at least try to engage in conversation, specially if you’re the only customer. Portuguese are usually polite but reserved to strangers, and keep them in peace.

After an hour or so, I just went to the toilet, retouched my hair, and decided to go back. If I ever get another opportunity to visit Faro crossdressed, I know where to go — this is a most welcome place for the likes of us. And while it’s very small, it seems to pack a crowd during the show days. I certainly hope to be able to visit it one day when there is a show going on. [Note: the Heaven Club seems to have closed its doors…]

On the return back, I hit another gas station — but this time, it was an automatic one, so there was no need to interact with any human. Oh well. I was getting used to having fun doing that 🙂

In the end, I came back relatively early, so I drove around The Strip in Oura again. This night, being the middle of the week, there were much fewer people than on Saturday, and half the establishments were closed. I toyed with the idea of having a drink on one of them, but, on second thoughts, there was a long trip back ahead of me on the next day, and it would be better to get a bit more sleep instead.

I got “seen” by the female hotel attendant again, but, again, she didn’t raise any questions, just watched me go by. And that was all.

Needless to say, these were my best vacations ever 🙂

And of course, I have still a lot to think about. But this post is getting waaaay too long for that. Maybe I’ll share a bit more about what I’ve learned about myself and the whole experience. But that will have to wait until the next post!

Until then, cheers to you all!