I’ve Escaped From Prison

By Amanda J.

I can almost hear the cries of “Uh-oh, I always knew it – that Amanda’s a bad ‘un – prison was probably too good for her.  Let’s hope they catch her and lock her up again soon” but let me well and truly quash any rumours before they start.  Apart from a tour round Alcatraz in the mid 1980s, I have never set foot in a prison, let alone been sentenced to do ‘time’ in one.  In fact, I try to live as honest a life as it’s possible to live while dishonestly keeping a certain side of me hidden from those around me.  But there is a connection between this post and prison although you’ll need to bear with me for a few minutes before we get to that connection.

I am a closeted crossdresser.  No one who knows me in the real world knows about this side of me and anyone who discovered my secret, and particularly anyone who saw any of my more recent photos, would be flabbergasted.    But the truth is that you can’t be a closeted CDer in a house full of people.  We rely on hearing that front door click as our last companion leaves to herald the start of our much hoped for ‘me-time’.  Stashes are retrieved, garments set out, cosmetics arranged and we eagerly set to work, transforming ourselves into our gentler and (hopefully) better looking alter egos.    A bang on the door?  Ignore it, it won’t be anyone important.  A ring on the doorbell?  Amazon can leave the package behind the bins like they normally do.  This is our time for ourselves and no one is going to interrupt it.  Our front door has once again protected us from the outside world and when it is finally time to put ‘her’ away for another day, we breathe a sigh of relief that it hasn’t let us down.

Where would we be without that sturdy front door?

But there’s a problem.  Every week on Kandi’s Land, either Kandi or one of the other girls inspires us with yet another tale of interactions with the outside world underlining how accepting much of the world is of our small community.  But with that inspiration comes a little envy – we want to join in but we can’t because we’re stuck in the closet.  And slowly but surely, we start to feel that our sturdy front door isn’t really keeping the outside world out.  It’s keeping us in.

It’s the door to our prison cell.  And like the door to every other prison cell, it prevents us escaping.

But why should that be?  Have we actually done anything wrong that warrants us being locked up in the first place?  Has someone locked us in and thrown away the key?  Are there armies of ‘screws’ outside making sure that we behave ourselves and don’t have any thoughts of breaking out?

Of course, the answer to all of these is a resounding ‘no’.  There’s nothing wrong with trying to live our life in a way that fulfils us and doesn’t harm others.  That door is on the same latch that it always is and can be easily opened from the inside.  And the truth is that we are both prisoner and warden, at the same time lamenting our incarceration and making sure that that’s how things will remain.

If this is how you feel, I have bad news for you.  You have a life sentence without parole.  No one is going to come and give you the news that you have served your sentence and you’re now free.  You won’t even be released from solitary confinement!  Your only chance of freedom is to plan a breakout but unlike ‘The Great Escape’, you won’t need to dig three tunnels, forge papers, steal a motorbike or even learn to speak German.  But you need a plan and, to help you, here’s how I accomplished my ‘great escape’.

Part one of the plan dealt with the front door.  Mine has a small window covered by a curtain.  One day, I did the unthinkable – dressed in all my finery, I moved the curtain just enough to look through the window and, when I did, I got the shock of my life.  The outside world looked just the same as it did on every other day.  I may have been dressed very differently to normal but everything else was the same as ever.  ‘Hmmmm, I wasn’t expecting that’ I thought to myself.

And then I started wondering what would happen if I actually opened the front door.  Would there be a chorus of ‘Crossdresser at number 5, crossdresser at number 5’ from all of the neighbours who, anticipating the spectacle, had all congregated in front of the house with flaming torches to watch the drama unfold?  Only one way to find out so I turned the latch and opened the door just an inch or two.  And again, I got the second shock of the day.  No chorus of baying locals, just silence save for the occasional passing car and tweeting bird.  That was the point I realised that I could actually do this but escapes need proper planning so I closed the door and went to think about part 2 of the plan.

Part two centred on my appearance.  All good prison breaks need a good disguise and, as I wasn’t planning to escape under cover of darkness, I needed one to fool the ‘goons’ who would undoubtedly be patrolling outside.  Something that any woman may choose to leave the house in but at the smarter end of casual.  No point in going to all that trouble only to wear what I’d wear on any other day but, equally, going full femme with my beloved bodycon dress and stilettos may attract attention.  So I plumped for a long pleated skirt, cowl necked sweater, ankle boots with a block heel and dark tights with a long warm coat over the top.  Just right for blending in on a November morning.

But, wait a minute, this was 2020 and covid was playing havoc throughout the world.  Face masks were de rigeur and, I realised, wearing one would actually enhance my disguise.  Or to put it another way, ensure that any neighbour looking out of their window would be even less likely to realise that it was me.  The whole thing was looking more do-able by the hour.  Time for the third and final part of the plan.

Part three, the final part, was the escape itself.  With the house empty, I retrieved my disguise and changed out of my prison clothes (jeans, T-shirt and sweater) and prepared myself for the big event.  I got dressed, did my makeup and, after putting my mask on and a final check in the mirror, moved gingerly towards the front door.  With a final check through the window to make sure that the coast was clear, I opened the door and stepped outside.  After a quick look round to check the neighbours weren’t outside, I started to make my way up the drive.

But then I stopped dead in my tracks.  A passer by appeared from nowhere (probably down the road actually) and looked straight at me.  I’d been rumbled and I hadn’t even got to the end of my drive.  Or had I?  Thanks to my mask, there was little to tell the world that I was not what I appeared to be and I very much doubt that he was in the habit of checking out every person he saw to ascertain whether their chromosomes matched their appearance.  He probably just saw a woman in a mask and carried on walking.  And so did I, free of the confines of my self-imposed prison at last.

And the biggest surprise of all as I walked in my neighbourhood?  It all felt completely normal and just left me wondering what I had been worried about for all that time.  So normal in fact that I’ve repeated the exercise and am now champing at the bit to go further afield.

Some of you will read this and it’ll bring back memories of your first time.  An event now superseded by shopping trips, evenings out and doing all of the other things that make you the awesome person that you are.  And even if it was a long time ago for you, I hope the memories made your smile.

But some of you will read this and realise that your fears are the same as mine were.  I’ve tried to be light hearted in the way I’ve described the episode but it is a huge step to make and one that needs thought, not impulse.  My message to you is that, if you’re sensible about it, you have nothing to fear but fear itself.  You don’t have to go out if you don’t want to and many girls are quite content to stay in the safety of their home.  But if you really want to spread your wings, don’t let your worries hold you back – by taking things steadily, you can conquer your fears and live the life you want to live.

And as Neil Armstrong nearly once said, it was one small step for a man, one giant leap for Amanda!