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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…..


12 Responses

  1. Amanda,
    A great post that tells the tale of how all of us got started. You are able to put into words what we think and feel.

    This is great advice for those individuals who are getting the urge to present female to the world.

    When I first started dressing, during Jocelyn 1.0, I never just wanted to stay in the safety of the house. I would put on my first dress and makeup with 3” heels and drive to a neighbouring town and walk the sidewalk in the evening. I did all the things you suggest we shouldn’t do. I lived and learned and now my Jocelyn 2.1 daytime outings are very enjoyable.

    I needed someone like you back then. I’m sure your writing will be a big help to many people who are starting on their female journey.

    Thanks for posting.


  2. Jocelyn, thanks for sharing your thoughts!

    The first outings are truly life-changing and I’m sure that we all have our own stories to tell both in terms of the highs we’ve experienced and the risks we’ve taken! But it’s great that we can share our experiences in a forum like this and, as I’ve said before, it was reading your experiences that encouraged me to take my own steps into the outside world – there’s something quite magical about finally overcoming our fears and being out & about and mingling with the crowds isn’t there?

    Thank you as always for your friendship and support.

  3. Good afternoon Amanda,
    You should think about incapsulating Crossdressing 101 into a book. You are so well written I’m sure it would be hit in our community, If not else where. I ordered a book not that long ago that was highly recommended by a friend when I told her my wife and I were seeing a counselor. She thought both of us would get a lot out of it, it’s called “My husband wears my clothes”. Some of us hear on Kandi’s land may have heard of it. So I’m excited about it’s arrival. Maybe I’ll fill you all in once I’ve read it.
    Back to your post though, us blondes are so easily distracted, another well written part of Crossdressing 101. I’m sure there are already a lot of ladies out there saying thank you Amanda, you’ve been a huge help to our community.


    1. Trish, thank you for the compliments! Sadly, whilst I’m certain that Mrs A would feel thrilled to be married to a best selling author, she may not be quite so thrilled when she discovers where my particular sphere of expertise lies, particularly when she realises that it’s been written from direct experience in the field! Of course, being married to a CDer brings many advantages to a wife but many don’t realise exactly how lucky they are, Mrs A included!

      So fortunately for Kandi, Kandi’s Land will remain the sole destination for those who seek my wisdom (and shake their heads in despair over my delusion!!).

      I’m looking forward to the book review when you’ve finished reading!

  4. Amanda, I had flashbacks to my earlier days of CD life, when I only dressed in the house with no makeup, as I wasn’t going to use my wife’s supply. When I finally got the courage to go to a local support group, I had some simple skills and a donated wig. But that first step out opened my eyes to the possibility of being part of the public rather than secluded and alone. It took a few years before I did it, but now I can’t imagine getting dressed and NOT going out.

    I agree with Trish, a book is a great idea to collect your well-written thoughts and experiences on this subject.

    1. Tina, thank you for sharing your thoughts and experiences. As I said to Jocelyn above, there’s something quite magical about being part of the crowd and I’ve taken big steps in that direction in the past month. I think many of us spend too much time worrying about whether someone will realise what we are when they see us rather than accepting that that will happen but it doesn’t matter, either to us or to the person that realises our secret. In the end, we’re just being ourselves and there’s absolutely nothing wrong with that.

      See my reply to Trish regarding the book idea!!

  5. Question for Amanda
    Would Mrs. A be “thrilled” by the extra income from such a book?
    I love royalties!
    Dress sensibly, dress for the surroundings. Buy and wear clothes and shoes that fit. You don’t want to look like a sausage in a dress. Wear shoes that you can walk in for hours. Walking in public is very different from walking around your house. Different surfaces, cracks, stones, and surface slants are just a few of challenges you might encounter. Maybe have a backup pair in your car. I had several events in the past two months were my heel broke, one was at an airport.


    1. Cali, I think Mrs A would be very thrilled with the income but not so thrilled with the identity of the author! I guess reassurance that the dress, heels, hosiery, makeup and wig are just the uniform of a working author could be an angle to try but I’m not holding my breath for an easy ride!

      And I love your ‘sausage in a dress’ analogy! But joking apart, that’s very good advice and your point about surface slants is often forgotten. A 3″ heel angles the foot at about 40° which already puts a strain on ankles not used to them. Walk down a 5° slope (which is a common slope on wheelchair accessible entrances and walkways) and the ankle is now having to bend by 45° which can be beyond its limit if previous walking in heels has been restricted to level floors in the house. And I’m ashamed to admit that I learned that lesson the hard way!

      1. I once walked down a steeply sloped driveway SIDEWAYS holding the arm of my friend. And she laughed all the way down. The other thing is compounded slopes where the slope is perpendicular to your line of travel. Stilettoes on polished concrete floors covered with wet leaves is a wild adventure.

        1. I’ve discovered the ‘crab’ walk too – it’s just about possible to retain one’s dignity while doing it.

          Of course, the easiest way to negotiate a 5° slope is by walking backwards – the 40° slope of the shoe then becomes a much easier 35°. Sadly, it brings many more problems than it solves in other areas!

  6. Amanda,
    It took a while for me to understand the obsession for stepping out the door , why aren’t we content with the security of closed curtains and our four walls ? It was never going to happen for me , the idea was so crazy why take all those risks ? I would think the majority of us have the need to share with someone , I hoped my wife would come on board but those they were soon dashed . Being a member of an online forum can create peer pressure , if they can do it so can I ! In the early days being read wasn’t the problem in fact it was fun , the problem was the more I went out the less I wanted to step back into male shoes , the goal was obviously total acceptance as a woman .

    We fear the possibilty of a bad experience , it’s important to consider why would an average person in the street want to give you a hard time , if fact it would be interesting if other members could pass on their stories if they have had problems . In almost six years it’s never happened to me , OK you might get misplaced words but every single one I’ve heard have been accidental rather than malicious ( my ex-wife is the only one ) .

    Your suggestions on careful choice of clothes and shoes are correct , I found you have to get to know your circle of contacts (male or female ) before you can gently push the envelope . I usually dress in Tshirts and jeans for my painting group but recently we had a Xmas meal in a restaurant so pushed to boat out with a smart dress and heeled boots , all I got was , ” Oh you look nice !” If I’d attended the first class dressed like that I would have had a totally different reaction .

    1. Teresa, thank you for commenting. I think the point about risk to personal safety is that it’s a lot lower than we imagine but, if something does happen, it can possibly be very bad which is why walking around secluded areas after dark is not a good idea. We can also obsess about passing but, as I asserted last time, it doesn’t matter. Every time I step out of the door, I understand that someone somewhere is going to realise that I’m not what I appear, particularly sales assistants and anyone, if not everyone, I interact with. But I don’t care because I’m not going to allow anyone to get in the way of my happiness, whether an accidental ‘misgendering’ or deliberate ‘outing’.

      I think the whole thing about going out stems from increasing self acceptance. In the early days, the whole thing was about the reflection in the mirror so the idea of being out and about never crossed my mind. But as the inner woman took hold and I realised that it was a facet of my persona that I was both happy & comfortable with, I started to resent the constriction that being housebound imposed on my female identity which contrasted with the freedom male me has. As I’ve said in a previous post, I’m very much a loner and enjoy my own company but still need to feel that I am a part of society, not a recluse and a trip to a local town gives me everything I need in that respect.

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