Walking around…

As I get used to driving around in the early hours, thanks to my beloved wife who finally got used to the idea that I have this “urge” to go out, I’ve been getting a bit bolder, and also getting a taste of what it feels like to be “seen in public”.

Of course, there is rarely anyone around at 4 or 5 AM. So it’s quite different from being in broad daylight in a public space. Bear with me as I relate my recent experiences, taking into account my current limitations and constraints 🙂

Now I have learned a lesson in humility. I have for long since claimed that the main reason for not going out further was not “being afraid”. While that hold true for a long part of my “closet” phase, the truth is that I wasn’t “afraid” when I went out for the first time, which I believe was around 1999 or so. I was excited and obviously anxious, of course. But back then there was no “fear” of discovery. I had just started dating my current wife and had no idea if it would become a long relationship or not (I had no expectations, to be honest). When I went out, I was on vacation on a hotel on a city away from home, where nobody really knew me. Sure, I could have gotten a few odd looks (which I actually didn’t get), but the truth is, the notion of “being caught” was not at the top of my mind.

Later on, of course, I was prevented from “going out” for many, many years, because my wife didn’t allow it. When I finally got the green light to be able to “go out” again, the current rules is that I may only do so when my wife is asleep — which happens around 3 or 4 AM (I usually need some preparation before going out, too). Her reasoning is that when she’s sound asleep she doesn’t get anxious…

So I was mostly “excited” and not really anxious, but… I wasn’t being very honest about my feelings. As I have discovered on my latest “going out”, I’m actually still a bit “afraid”.

Let me tell you this experience. These days, for some reason, Tuesdays and sometimes Thursdays seem to be the better days for going out — it has to do with my very complex schedule of juggling things that I have to constantly do for my wife. So the last crossdressing session was on a Tuesday. This is the kind of weekday where nothing happens. Even many late-night bars are just open from Thursday to Sunday, at least in my area — it’s a highly touristic area, but strangely it has a relatively low number of open bars in the late hours (people just drive to Lisbon instead). Pretty much everything closes at 4 AM, because it requires a special license to be open beyond that, and to the best of my knowledge, no bar or club is open after 4 AM in my neighbourhood. So, for all purposes, it’s a “safe” time to go out, because nobody will be around — and we fortunately live in a low-crime area (on the other hand, criminals are clever enough to stay in bed if nobody is around to be mugged 🙂 ).

So last Tuesday I went through my usual routine… going out a bit before 4 AM and driving around. I have now my favourite spots for walking in heels — I favour medium-density residential areas, where everybody is asleep, but which are not hopelessly remote: this means if something seriously goes wrong, I might easily hail a taxi or even find a place to call for help.

Since it wasn’t 4 AM yet, I boldly went to a beach bar which might be still open. It wasn’t — I suppose summer hasn’t really started yet! In any case, at that moment I was having some doubts if I would really dare to go to that beach bar or not. It’s not too big, and, since the night was mild, if I wished to smoke, I would have to be on the outside esplanade, which (during the day) commands a lovely view on a small, cozy beach. Now the tricky bit is that this place is well-known, and some of my wife’s old friends (she hardly sees them any more, but she occasionally keeps in touch with them now and then) might be there. It’s true that it would have been an amazing coincidence — specially on a weekday! — but not altogether impossible. So I was apprehensive when I reached the parking lot (it’s been some time since I last remembered their cars, and, anyway, they might have walked to the beach bar).

At the end, there was nothing to worry about: the parking lot was completely empty and the bar had already closed down for the night. So I just enjoyed the sea breeze and the sound of the heels clacking on the pavement — there is a brightly lit underway passage leading to the beach from the parking lot — and took a few (horrible) pictures. Yay! Sandra on the beach! What a novelty! Granted, I wasn’t really on the beach but just on the access stairway to it, and it was pitch dark outside the lit areas, but it was the closest I could get to a beach fully dressed as a woman 🙂

Nobody was around for miles so I felt pretty well about it, which increased my confidence and self-assurance.

Thus, I enjoyed a smoke and went back to the car, checking the time: 4 AM has long since gone, and it would be pointless to locate another bar. So I thought I’d go back to another of my favourite spots for walking around: it’s a large plaza in a residential area, near to the sea but actually without a view, with lots of cafés and restaurants during the day, all obviously closed by now. There is a good reason for using this spot as my “walking around” place: there are three hotels (one in the plaza, two nearby), so, again, if something went seriously wrong, I’d be able to get help from them.

At the beginning all went well. The night was so mild that I managed to leave the overcoat inside the car; I don’t like it so much, since it’s unflattering for my figure. I just grabbed my purse and walked towards an antiquities shop which I fancy: it has a large mirror, on which I can “check” myself and enjoy my reflected image for a while. Usually I just have another smoke and return to the car; there is hardly anyone around, except for the employees at the hotel(s), but they don’t get a clear enough picture of myself to worry me in the least.

Well, all of a sudden — I got company!

I forgot the garbage guys. They do their rounds at unpredictable times, but 4 AM seems to be a good time for them. All of the sudden, I hear the garbage truck speeding up the plaza. And here is where I made my first mistake.

I wasn’t very far away from my parked car. Nevertheless, I would most certainly be “seen”. For some reason, I wished to avoid that. Not that trash guys in my country are violent. In fact, trash guys are an odd job which surprisingly fail to attract any immigrants. They’re not wonderfully paid, and it’s not an easy job, but apparently only the Portuguese apply for that job. In fact, perhaps surprisingly for many of you, the trash guys around here are actually rather polite — when I’m in my “male mode” and meet them doing the rounds in my neighbourhood, I wish them a good night and usually get a smile in return — they’re kind and nice. Don’t ask me why, but they’re generally well respected, people tend to help them doing their rounds (e.g. moving cars away or patiently waiting without complaining when the trash truck is stopped in the middle of the road), and they are, in general, rather good looking in their modern uniforms — rather the opposite of the stereotype that one usually has about trash guys.

Still, for some reason, I didn’t want to be “seen” by them. So, instead of walking back to the car, I hurried towards a dirt road leading out of the plaza and sort of hide there. And lit my cigarette in secrecy and waited.

Then I noticed that this would take longer than I had expected. You see, we are in the process of moving away from the “regular” trash cans, and the City Hall is slowly replacing them all with underground waste containers. These look much nicer, are fixed, and have lots of capacity — and, since they are just a chute to a large underground container, there is hardly any smell at the surface, even in hot summer days (or nights). They’re also less prone to vandalism or deterioration. Sure, they’re costlier (since they require some building work), but the expense is worth the investment, since you don’t need to empty them as often. The disadvantage, of course, is that they take much longer to be emptied. Much longer: instead of a minute or so for the “normal” trash cans, the procedure could take 20 or 30 minutes — I had only seen that once, and didn’t spend enough time around to measure the time.

When I realised that, I rethought my position: I was now on a dirt side road, away from the plaza and the relative safety of light and a clear path. This side road lead to some garages and the backside of the buildings facing the plaza. Now someone just standing there, at this most improbable place, would attract undue attention. One thing is to be checking myself on a mirror in a (closed) shop — after all, entrances to the many residential buildings were nearby, and someone noticing me (like the trash guys!) would just assume I was returning home. The other thing is being on a spot where clearly there are no building entrances. That would point out suspicious behaviour.

Well, I had no choice but to follow the dirt road. Fortunately, I soon figured out that it would lead to the street above the plaza (which opens to one of the other three hotels), so that would be safe enough. In fact, my plan was just to remain in the shrubbery facing the road and wait there, out of sight, until the trash guys finished their job.

Unfortunately, a dog from one of the nearby villas got surprised by an unlikely “visitor” coming up from the dirt road. And you cannot imagine how loud he barked! He was totally harmless (and firmly tied to the spot) but of course he would also attract attention — except for some rumbling noises from the trash truck, the night was utterly silent. If I had a watching dog in my villa who did non-stop barking at such an odd hour, I’d come out to see what was wrong.

So, hmm, I thought… I know this neighbourhood rather well, my wife and myself tend to come here during the day and have some coffee at the esplanades, or to a nearby supermarket. So I knew that I could walk all the way around and come back to the plaza from the other direction, all through well-lit streets. It would be quite a walk, but manageable; I was wearing my sandals, which have a wide heel and are rather comfortable in spite of being 3.5″ high. In any case, this would take me some time, enough — I hoped — to let the trash guys finish their work and allow me to return to my car in safety.

And, well, it would be my longest walk on heels ever. I prepared myself to enjoy it fully!

It was fun for the first part. Someone actually came out of another house, but I didn’t even bother to look back; I didn’t hurry, either, but kept my pace until the next street corner, and then turned left, coming into one main street, which would lead me all the way to the plaza. Well, not in a straight line, but it was the only alternative way I had. So I walked and walked.

This main street was well lit and has villas along one of the sides. I’m not overly fond of villas — not only because of the dogs, but mostly because it’s really hard to explain what you’re doing if you don’t live there. Also, unlike buildings, there is no easy way to hide. In fact, it would look way more suspicious if I tried! So after a while, perhaps some 10 minutes or so, I was not so happy about my decision, but getting back would be worse — so I stuck to the way and continued to proceed along that street.

At some point, a car drove by — which wasn’t so surprising at all, that street is, after all, one main street in the neighbourhood. But then I noticed that the car was actually driving very slowly, which was not so usual. Sure, people can be a bit more careful on residential areas and drive slower, but not that slow. At first I thought it was a taxi, looking for customers. But no — it was some kind of service van, and it was clear that the driver had spotted me and started to drive slower to figure out what I was doing. Uh-oh!

I kept my determination and sang froid and just continued at the same place. I was checking for alternate routes or spots to evade that stopping driver before he stopped completely, since it was clear that this was his intention. Unfortunately, that street doesn’t have any side streets — it’s a long stretch without a single crossroad! I had no choice but to proceed and hope for the best.

And this is where I got my first taste of being a woman at 4:30 AM on the streets, alone, and unprotected — with guys suddenly developing an “interest” in me. Let’s say that I was not very comfortable about it. What would I do if this guy really stopped? Probably the worst that would happen is to get him very angry because he had confused me with a real woman! Some guys — specially those not so confident about gender issues and their own maleness — get really pissed off when they “confuse” crossdressers with real women, and this could get nasty… on a place where nobody was around. Or, worse, if there would be some kind of real mess, the owners of the villas would certainly see what was going on and call the police, which would not be a fun experience for me!

The service van continued at its own slow pace but actually passed me. For a moment I thought I had just been imagining things. But then I understood. At the end of the street, where an intersection leads back to the plaza, there is a night club (unfortunately closed, too; I had checked it on a previous night) and a small gas station across the street, also closed. The guy in the van just drove into its parking lot and stopped there. This didn’t bode well at all for me. It could be a coincidence, but what person drives into a closed gas station in the middle of the night and parks there? Across the street there is just the night club, it would be unlikely that he lived nearby: there are far better parking spots for the residential buildings around the plaza. So this could only really mean one thing, and I wasn’t really happy about that.

Now at this point I actually got lucky. There is a new street which had been opened a year ago, leading to the main street which I was following, and which opened on my side of the sidewalk. I didn’t actually know where it lead, but maybe it would lead me back to the plaza somehow. At least, since it reaches back into the buildings area, there would be better places to hide; so I could wait both for the guy in the van to lose interest and the trash guys to finish their job. How long I would have to wait I had no idea, but this seemed to be the best that I could do at the moment, so I chose this new street and abandoned the guy in the van in his parking lot…

At the end this turned out to be a good choice. The new street leads into two new parking lots, and these, in turn, are connected to the plaza, or almost. So I could walk, unseen by the guy in the van, back to the plaza and to my car. All I had to do was to wait for the trash truck to pass, which actually happened at that time — perfect timing! Full of confidence again, and with a smile in my face, I walked back towards the plaza.

But there was another surprise. Apparently, emptying the underground garbage containers is a two-step process. First, the big trash can empties the biggest amount of trash they can. But then a much smaller service van with two trash guys do the finishing job. I had no idea! So I pretty much walked into their line of sight, while they were busy emptying something at the containers, and turning back would be highly suspicious. Also, I couldn’t see the parking lot of the gas station from where I was: did the guy leave the van? Was he still waiting? Did he drive out of the parking lot, looking for the “woman” that so mysteriously disappeared on a side street? I had no way of knowing, and my own car was not that far away.

I was also getting tired — the after-effect of so much adrenaline and a twenty-plus-minute walk. So, well, this time I had to face the two trash guys. There was no way to avoid being seen. I just went across the cobbled sidewalk — which broadens a lot at the plaza — and calmly, but firmly, walked towards my car.

The two guys noticed me, of course. I got a few wolf whistles and some complimentary comments 🙂 Well, perhaps not that complimentary, but they weren’t actually rude, more like joyful. In fact, I had been a bit stupid about avoiding the trash guys in the first place: after all, they were at work, and they have very strict schedules to keep. It would be far more unlikely to have them “attempt” something — they would have to account for the time spent to their supervisors, and “having fun with a crossdresser” would hardly earn them good marks with their bosses. So they could just have a laugh at my expense; I have no idea if they “read” me, but I think not — I wasn’t close enough for them to look into my face, and all my padding, seen from afar in the middle of the night, is convincing enough. So I ignored them the best I could, but kept my smile, as well as the determination to get back to the car, which I finally reached. Whew! I was safe for the night.

When driving back home, the guy in the van was still in the parking lot of the gas station. I have no idea what he was doing or what he was thinking. It occurred to me that he might just have picked a mobile phone call from his sweetheart and just pulled over on the first parking spot to be able to talk to her — fines for driving and talking on the phone are rather high in my country. This would also explain why he was driving so slowly. So it could have been a coincidence after all — I have no way of knowing.

Well, all this sounds a bit ridiculous when written down 🙂 After all, nothing happened. Most of it was my mind imagining things and foreseeing the worst. But it taught me a few lessons.

First and foremost, that my wife — as always! — is right: with more familiarity with walking around crossdressed, I start getting careless. So the risks become higher. If I had picked a different spot for walking, or didn’t walk at all, nothing would have “happened”.

Secondly, that after all I’m more “afraid” than I thought. Because of my stupid reluctance in being “seen” by the trash guys, I did a lot of unnecessary things, and risked being “seen” (or who knows what else) at a much higher degree. So I was jumping from “difficult situation” to “even more difficult situations” which would become increasingly harder to explain if I got “caught”. Nevertheless, the point is: I’m much more of a coward than I thought! I’m not that easy about walking around crossdressed as I thought I was! In spite of everything, I’m still afraid of getting caught, even if I often proclaimed otherwise!

And thirdly, there was a nice (and unexpected!) lesson of “being a female in public”. Even though “nothing happened” and I was just clearly seen by two trash guys, there was a feeling of “helplessness”, which is what I guess that most real females would feel in similar situations. As a male, I would never have done what I did. Even alone in the street at 4-5 AM, I wouldn’t “hide” from trash guys. When walking down an empty street, a car slowing down wouldn’t really make me afraid — I could imagine they had the intention to rob me, but there wouldn’t be “anything else” besides that. In any case, of course, in my “male mode” I can walk everywhere unmolested in plain daylight, which I cannot do when dressed as a woman. When I become Sandra, I also get some disadvantages, and not only the “advantage” of enjoying the feminine role which I so cherish. The biggest disadvantage is that I’m more prone to being, well, attacked, to put it bluntly.

Of course that this only gets worse because I’m not really a woman. A real woman might have been able to run away, or give some sharp answer, or something like that. In my case, if I came into much closer contact with potential observers initially “mistaking” me for a real woman, but then feeling disappointed and cheated, things might have turned nasty. On the online world, I often get very powerful negative reactions from guys finally figuring out I’m not a real woman, and they feel tricked, cheated, and often are furious.

This definitely made me pause a bit and reflect. It’s good to see the “disadvantages” of being a crossdresser. It’s not merely being anxious about the “next time out”. It’s not just the frustration of not being able to afford some new things (I definitely need a new wig!… and some more variety in dresses). It’s not only the stress of never knowing when I’m allowed to dress again. No, there are a few risks involved which make the experience dangerous and not really fun as it should. On the other hand, going through the “bad side” of crossdressing also makes the experience more rich, more real. Obviously if something did go wrong I might think differently; and the more I expose myself, the more likely “something bad” can happen, even if it’s not exactly life-threatening — but more like “being spotted” in complicated circumstances which might not be easily explained and would result in “revealing” myself publicly as a crossdresser to who knows whom.

Still, I’m looking forward to the 19th or the 21st, when one of my relatively recent T-girl acquaintances showed her availability for going out with me, even at my odd hours. Being together with someone who has a lot of experience in going out might make me more confident in tackling those potential (but not “real”) fears of being spotted. I mean, if we were two T-girls happily walking down the street and a car passed by and slowed down, would we be afraid? No, we would just laugh and joke about it. Short of facing a gang of skinheads (which don’t roam my neigbourhood), being with someone else together would not be that “dangerous”.

Of course I expect to go out again! But I will be more careful next time. Even though I tend to pick spots that I know reasonably well, it’s clear that it’s best to stick to places where there are more avenues of “escape” or hiding myself from view. I know several of those spots. In fact, the above mentioned plaza is not such a bad place at all: my mistake was to avoid those first group of trash guys and go outside the “safe zone”. I should just have returned back to the car; after all, that’s precisely what I did when the second group of trash guys remained at the plaza. The problem here is making mistakes when one has little experience in walking around crossdressed, and those mistakes might lead to unpredictable results.

But I’ve learned something about myself — that I’m not so bold as I thought, and that women (and crossdressed men!) are actually more vulnerable to exposure, specially in the middle of the night where anyone on the streets might be “suspicious”… even myself.

  • Erin

    Oh Sandra, firstly, I'm glad you are ok and that nothing happened to you; secondly, that i hope it doesn't quell your desire to continue to boraden your horizons in terms of getting out into the world in other than 4AM adventures. I read this with anxiety thinking something actually may have been going to happen that would make you decide to hang up your dreams of going out even more, hopefully thats not the case. You must look at it from the positive, you dealt with the situation as a woman would have, by protecting herself (there is nothing about your responses that would deviate from what a gg would do in similar circumstances). I LOVED the part about the mirror (you know full well why). And the part of your 20 minutes in 3.5 inch heels (WOO HOOO GIRL), and the part of you smoking (a given right). Ohhhh the adventures of Sandra are just getting exciting, i sooo adore you girlfriend. Kisses and hope to talk soon all about this.

  • Alda Cecília

    Dear Sandra,
    Thank you for these exciting moments. You made me revive my own past experience(today I won't take anymore the risks I used to). It was a trully happy moment for me to read these words and know about you. Kisses and blessings

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