Strutting out of a Comfort Zone

The life of a crossdresser is all about going out of our comfort zone in an attempt to be happy.

Let’s face it, for many of us “girl clothes” make us happy.  We (and yes, I know I am generalizing and not speaking for all non-cis people) love panties, heels, skirts, dresses, nail polish, eyeliner…The first time we wear anything that isn’t purchased in the boy’s section of a department store is a thrilling, frightening, experience. 

The first time (and possibly the fiftieth time) is a terrifying event.  All of the normal thoughts and fears run through our head.  What if someone sees us?  What if the cashier laughs at us?  When I am shopping for MAN clothes in MAN mode, I never worry about seeing someone I know.  I don’t consider what the cashier might think for even a second.  But buying foundation or a skirt in male mode?  That’s a different story. 

Although I have been shopping in any department I wish to for decades, the same paranoia creeps into my heart and mind. Buying lingerie or makeup or heels is a step (or a strut) outside of our comfort zone.  We are shopping for beautiful clothes with a baffling set of measurements and sizes.  What on earth is my bra size?  34B?  What does that even mean?  What is the size conversion of boy shoes to high heels? Is my foundation color beige or sand? 

At one point this was a new world for us.  At one point we stepped out of our comfort zone to start a wardrobe that we wanted to, filled with beautiful clothes and heels and makeup that felt right, that made us happy.  Once we do this, it will lead to a life of continuously stepping out of our comfort zone.  Buying lingerie leads to wearing it, so there’s a new zone right there.  Lingerie may lead to heels, another zone.  We may go to a new zone with dresses, then makeup, a wig…  zone zone zone. 

As we make these steps what we think of as our comfort zone changes.  These days shopping is pretty routine, going out en femme was once waaaaaay out of my comfort zone at one point but again, it’s pretty normal to me.  


Going out of your comfort zone, for the most part, a good thing.  It expands your world, opens up new adventures, and enriches your life.  I mean, it’s as scary as it can be, but it’s usually worth it.  I can’t think of a time I regretted going out of my comfort zone, regardless of whether it is in regards to this part of my life, or in work, or in my boy life.  Even though I am happy and content, I still think about new adventures that are a step into a new comfort zone.  It could be flying pretty, it could be something else.


When we enter a new comfort zone, it can also be a humbling, almost traumatic experience.  And I don’t use that word lightly.  Although I talk about how the first and almost every time I have gone out en femme has been a positive or at the very least an uneventful outing, I know that it isn’t that way for all of us.  It breaks my heart to hear of a t-girl who worked up the courage for years to go out en femme only to be laughed at on their first time out.  It’s easy to understand why they went home and never went out again.  Wearing makeup for the first time (or the millionth) can also be humbling.  We spend so much time carefully selecting the right shade and watching tutorials and we imagine that we will be transformed into the girl of our dreams…  but the reflection tells us otherwise.  We hope the dress, the wig, the lingerie shows us a reflection of a cute girl, but sometimes the mirror (and our minds) are cruel and we see a man in a dress.  A humbling experience can push us right back into our old comfort zones, never to step outside of them again.


Sometimes.  We know, or soon learn, that this side of us isn’t going away.  The parts of our heart that want this don’t get quieter, they continue to sing.  Soon we are back pushing ourselves out of that comfort zone to try again.  


The humbling experiences don’t go away.  Last night I tried on a new outfit and…  well, I didn’t like how I looked.  But I kind of expected that.  Trying on a top and a mini skirt in male mode looks…  well, I look like a man in a top and a mini skirt.  Once I am shaved (everywhere), and have my pads, my corset, forms, and wig on, the mirror will (hopefully!) show a reflection I am happier with.


We know that when we go out of our comfort zones it will likely lead to a humbling experience.  That’s normal.  The first time you do anything you will probably fail.  Baseball players don’t hit home runs the first time they play baseball, the Beatles wrote a lot of songs before they wrote a good one.  My first time doing makeup was…  a disaster.  But I kept at it and took lessons, bought better products, watched tutorials and I am okay at makeup.  Same with walking in stilettos, wearing false eyelashes, seasoning a corset, and a zillion other things.


Why do we do this?  Why do we go out of our comfort zones when we know we will likely have a humbling experience when we do so?  Simply put, because we don’t have a choice.  Once we acknowledge and accept this part of us we begin the next step of our (ugh) journey of gender identity.  Every new part of this adventure will determine if where we are is where we’ll stay or if there’s another road ahead.  At one point I thought I was going to underdress for the rest of my life.  Then I moved into “real clothes”.  This was a new comfort zone.  Soon I realized that staying home en femme wasn’t where my journey ended.  I started going out en femme, started a social/support group, started modeling (modeling is a generous term here) and so on.  Everything was a new comfort zone.  Everything was a humbling experience.


Despite these humbling (and often crushing) experiences I still look to push boundaries, to test new levels of comfort to see if I want to go in that direction.  I feel I haven’t done anything new for a while.  I wouldn’t say I’m restless, no.  If this is where I stay for the rest of my life I will be happy and content and acknowledge how blessed and fortunate I am.  The pandemic has made me very reflective and has reminded me that life is short and the things I want to do, the things I take for granted, will someday not be an option.  I will someday be too old, or too, well, dead, to do what I want.  Life creeps slowly and cruelly towards our final days, but life can also change quickly.  I could slip on the ice today and crack my ankle and my days of strutting in five inch stilettos could be over.  


So, what do I want?  As I mentioned I want to fly pretty but that is not happening any time soon.  I have not worked up the courage to do that only to wear a stupid mask for the entire flight.  No, when I fly pretty I am going to fly drop-dead gorgeous and everyone can see my makeover.  At one point modeling and photoshoots were out of my comfort zones.  Sometimes they still are, such as if they are in a very public place.  It feels a little… weird to have my picture taken while some people curiously look on.  Sometimes an outfit is outside of my comfort zone.  I don’t want to go out of my comfort zone for the sake of going out of my comfort zone.  I want to do things that I want to do, and if I need to break out of that zone to do, so be it.


Today after this is posted I am going to start getting ready for a photoshoot.  This one is very much outside of anything I have done before and I am terrified and excited beyond belief..  I know this will be the most humbling experience in my life, but I am going to do it anyway.  I am nervous and proud of myself.


Wish me luck! And be gentle if I post photos!

Love, Hannah

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