Crossdressing 101: Part 5 – I Want To Break Free

By Amanda J.

Of course, the title of this particular episode was also the title of a chart topping song by Queen.  Originally talking about a relationship, its significance as an anthem for personal freedom was soon picked up by several groups including the trans community and, indeed, the accompanying video reinforced that with the band members CDing for the performance (although it has to be said that Freddie would have looked far more feminine without the moustache!).

For me, the song title encapsulates the building pressure inside me to break free from the confines of the closet in which I was firmly ensconced.  In part 3, I talked about putting my head above the parapet and gaining the confidence to present this side of me to the online world.  I explained how, shy though I am, I need social contact and how the internet provided me with that.  But whilst I do enjoy my own company, I was increasingly feeling that the four walls of my house, which had hitherto provided me with the security and privacy that I needed to fully uncover this side of my personality, were preventing me from fully spreading my wings.

I mean who cannot fail to be inspired by the regular accounts here of acceptance in the big wide world?  I certainly couldn’t while I was all dressed up with nowhere to go, hidden and protected from the outside world by brick walls and closed curtains on the windows.  And strangely, it was those very same curtains that were instrumental in getting me out of the house.  More on that shortly.

As I write this, I’ve been trying to figure out how going into the outside world en femme became such an obsession.  There are far more good reasons not to do it than there are to do it as far as I can tell.  There are risks of discovery, mishap, personal injury, embarrassment and even of intervention by security if someone takes exception to a person they identify as a man entering a female-only space.  And that’s before you factor in the potential terror you’ll experience once you’re outside the security of your house.  You don’t get any of that standing admiring yourself in front of the mirror.  So it’s a huge call to make.

For a long time, I didn’t experience any serious desire to be out and about.  It was something I felt I’d maybe like to do but there are a lot of other things in life I’d also maybe like to do so nothing unusual there.  But also at that time, I had no sense that ‘Amanda’ was part of me.  Amanda was a name I used online but I never looked in the mirror and saw her; I just saw myself wearing women’s clothes.  And so restricting my activities to the house didn’t seem problematic – if ‘he’ wanted to go out, he went out in male clothes; if ‘he’ wanted to CD, he stayed in and wore female ones.  Simple.

But things started to change when I began to understand that all of this is a part of who I am; I no longer saw CDing as fuelling the fantasy but just as means to making me feel somehow more complete.  Of course, that’s an oversimplification because we all know that there’s a lot more going on than just that, but it is symbolic of the point when I no longer feared leaving the house dressed en femme.  Quite the opposite in fact; I now found myself battling to control a growing desire to fling the door open and step into the world. Rather than it being a case of ‘if he wanted to go out…’, it was now very much a case of ‘she’ wanting to go out.

It’s one thing feeling an increasing urge to take our feminine alter egos into the world previously only inhabited by ‘him’ but another thing completely when we decide to actually give in to those urges.  And that’s where the significance of the curtains became relevant.

As a closeted CDer, the whole of my feminine world was delineated by the walls of my house and, as I’ve already mentioned, the curtains were always closed for privacy and safety.  So in my feminine guise, I was never able to look out into the world occupied by him.  But one day, as I could feel the urges to leave the house getting ever stronger, I went to the front door, opened the curtain covering the small window and looked out.  In an instant female me could connect with the world previously solely occupied by male me and, at that point, I knew that the outside world was a place to experience, not to fear.  And two days later, that door was opened and I stepped through for the first time, but not the last.

I’ve already written several accounts of outings which are available on my ever growing back catalogue of ramblings here so there’s no need to go over old ground.   But I do think it’s worth addressing some of the concerns which we may have before taking that step.

The first concern is that we’ll be seen and recognised by neighbours.  That’s obviously a real risk but you can reduce it by learning what the signs are of them not being in – absence of cars in the drive and that sort of thing (but do bear in mind that whilst the neighbours may be out when you leave the house, they could have returned by the time you get back – don’t ask me how I know!).  But if it’s an unacceptable risk, then find somewhere away from home to dress if possible.  Budget chain hotels are ideal, particularly if they have early check in/late departure options but they’re also a great choice because most rooms have ensuite bath/shower rooms which makes the cleanup a lot easier.  Some hotels also offer day rates giving you the use of the room during the daytime but not overnight.  If that’s not an option, then some CDers get partially dressed and made up at home and then finish the job when they’ve parked the car.  Getting changed in a car is challenging at the best of times and the cleanup is also a lot more difficult in the absence of washing facilities but, for many, it’s the only viable option.

And then, there’s the ‘biggie’ – a passer-by will realise that we’re not genetically female when they see us.  As I said last time in part 4, whilst this is almost inevitable for ‘newbies’ it doesn’t matter.  But we need to draw a distinction between interacting with people and merely being in the same area as them.  Being out and about for the first time, we’re almost certainly just going to keep ourselves to ourselves and avoid any direct contact with other people and the truth is that if we walk through a crowded town centre, all of the other people there have far more pressing things on their mind than closely scrutinising every single person they walk past to decided whether their presentation matches their chromosomes!

But there’s an important point to be made here.  As CDers, we often go for glamorous clothes, high heels, plenty of makeup and hairstyles normally seen on much younger women.  That’s fine in front of the mirror but fraught with problems if you’re out and about.  Firstly, attractively dressed women attract glances both from guys and from other women.  That’s particularly true in this day and age when most women dress casually in jeans & similar when out in the daytime so the ultra-femme look stands out far more than it used to.  Secondly, there’s a reason that most women save their heels for special occasions.  You may be fine walking around the house in them but walk any distance and they soon remind you of their presence.  And not in a good way!

Dress appropriately for your surroundings and few, if any, will notice you.  And even if, in your locality, that means jeans and low heeled or flat shoes, you can still feel feminine though your hair, makeup (in moderation!), jewellery and accessories.

At this point, it’s also worth mentioning that it’s important that you don’t go out empty handed – the exhilaration of stepping outside en femme for the first time will soon turn into blind panic if you close the front door and then realise that your keys are still inside!  As guys, we tend to carry everything round in our pockets but women rely on handbags/ purses so before you go, make sure you pack essentials – house keys, car keys, mobile phone and a payment card are the bare minimum.  It’s also worthwhile packing an emergency kit comprising guy clothes & shoes and makeup wipes to leave in the car in case something unforeseen happens and you need to change back in a hurry.  And while you’re out, make sure that you keep your handbag with you at all times – again, it’s easy to forget something we’re not used to carrying around with us and don’t reach for instinctively as a result.

And before I draw this to a close, let’s talk about the time of day for your outing.  Many CDers venture out for the first time after dark figuring that the lack of light provides them with something akin to an invisibility cloak.   Perhaps, in the subdued light of the street lights and with less people out and about than in the daytime, they’re less likely to be directly recognised by someone they know or recognised as a CDer by people in general but it doesn’t take much thought to figure out that there are far greater risks, risks that women well understand and mitigate as much as they can by avoiding being out alone in deserted areas in dark evenings.  Of course, under all of our feminine finery, we’re guys and well able to look after ourselves if the worst happens but really?  Walking in heels is challenging enough without trying to run in them and even if the assailant has no interest other than stealing handbags, that could mean house keys, car keys, phone and credit cards gone in an instant.  There’s no right or wrong time to go out but it needs prior thought and consideration of the wider issues.  As far as I’m concerned, I may be more exposed to the rest of humanity when out and about during the day but I can be reasonably confident that I’m safe.

My experience outside the house is limited and every other contributor here has far more experience than I have.  But what I can say is taking that step is transformative and once you’ve crossed the threshold into the outside world, there’s no turning back.  You just want more!

As always, here are the five takeaways from this post:

1.  Don’t try to achieve everything in one go.  Even just stepping out of the house for a few minutes is exhilarating the first time you do it.  Each time you go out you can push the envelope a little bit further as your confidence builds.

2.  Take basic precautions.  If you’re worried that the neighbours will see you, try to figure out what their schedules are, what the signs that indicate that they are almost certainly out of the house are and have a quick look around to make sure that the coast is clear before you get too far over the threshold.   Remember to take basic essentials like keys, phone and a payment card with you and it’s also a good idea to have an emergency bag containing guy clothes & shoes and a packet of makeup wipes in case unforeseen circumstances mean that you have to change back in a hurry.

3.  Be sensible with your choice of outfit.  Choose things that will help you blend in with other women out and about and be practical.  The high heels and dress with mid-thigh hemline are fine for a bit of self-adoration in front of the mirror but will attract attention and the reason why most women save their heels for occasional evenings out will soon become apparent.

4.  Be respectful.  When you are out and about, you are seeking acceptance from other females.  Be respectful in the way that you dress and the way that you behave.  Act like a lady and you’ll be treated like one.  And this is nowhere more important than in women only spaces like loos.  If you need to, use them by all means but don’t linger and definitely don’t take selfies while you’re in there!

5.  Go out because you want to, not because you feel you have to.  There’s a fine line between ‘pushing the envelope’ and putting yourself into an uncomfortable situation because others do it or it’s on a ‘bucket list’ and whilst all of us here can offer any amount of reassurance that you’re going to be fine, if the idea of being in the outside world fills you with terror, then don’t go.  You won’t go down in anyone’s estimation if you decide to stay indoors and many CDers are happy with this type of arrangement.  Even so, whilst you may feel that the time is not right now, you may feel differently tomorrow or next month or next year so don’t be disheartened.

That’s enough for today.  Next time, I’m going to look at things from a different, but very necessary, perspective so stay tuned…..