A Good Day

When I look into a mirror it’s easy to… well, reflect.  And I don’t necessarily mean reflect in a literal sense (because obviously that’s how mirrors work), what I mean is that I’ll start to associate with how I appear with how I feel and how our bodies and our faces were shaped by our experiences.  These experiences could be from over the entirety of our lives, or even after a stressful week.  

When I am en femme I look at EVERYTHING.  How my shoulders look in a dress, whether a skirt is too short it probably isn’t), how my makeup is doing its best to contour my square shaped jaw, among other observations.  But I can be just as critical in male mode, too.  Last week I went in for a haircut after a very long week of very long days.  Like getting a makeover, having your hair cut is going to take place in front of a mirror.  And you can’t help but stare into your reflection.  I looked… tired.  I looked exhausted.  I looked liked how I felt, I was a literal reflection of a very long and stressful week.  I stared into the abyss and the abyss stared back.

As we age the years of our lives take their toll.  Wrinkles and lines and bag under our eyes appear and our bodies are designed to look more careworn, older, and more tired.  Of course global pandemics don’t hep either.  It’s normal and inevitable.  But knowing that doesn’t make it easier to accept.  Part of you realizes that today you look tired, and slowly over time this will continue.  Aging is not reversible.  Not really.  Of course there’s always plastic surgery and Botox and all that, but that can only do so much.  I feel tired a lot but I also work a lot.  I wake up each day and wonder if I will ever feel rested.  Do you know that feeling?

As the stylist got to work, I made a very blunt and perhaps overly cruel assessment.  I look like death.  A LITTLE dramatic but goodness I was feeling the week.  But I was in male mode soooooo the feeling dissipated rather quickly.  I try to be presentable as a boy but let’s face it, it’s pretty easy to do so when the expectations are pretty low.  A clean shirt and a less than disheveled appearance and that’s usually enough.

The flip side to this is literally the flip side to my gender identity.  I am waaaay more critical of myself en femme.  When I am getting my makeup done and when I am getting dressed, not only am I trying to look feminine, I am also trying reduce my masculine features.  Makeup and clothes have to do both for me.  Foundation might be AMAZING but is it going to cover up the blueish hue that a five o’clock shadow brings?  A dress might be cute but will it minimize my frame?  

Although time is stubbornly marching on and doing what time does to me physically (my stressful job isn’t doing me any favors in this regard either), I am feeling more confident and comfortable with how I look en femme.  Yes, I have days where I feel like a man in a dress and I have times where I feel less cute than others, but it’s getting easier to shake it off.  This hasn’t always been the case.  There have been times when I start to get ready and I would take a long look in the mirror and see the dark circles under my eyes, a week’s worth of facial hair, and a very tired man staring back at me.  I wonder how on earth am I going to turn THIS into HER?  One step at a time, baby.

As I continue the process (because it IS a process), HE starts to retreat and SHE starts to appear.  This happens not only on a physical, visible, tangible level, but also on an emotional one as well.  I know you know what I am talking about.  

I spent the entire day en femme last Saturday.  Well over fourteen hours.  It was glorious.  I knew I would be en femme for longer than I usually was and I thought about that as I got ready.  As I shaved my face I wondered if my makeup would be able to fight back against the stubborn and persistent return of facial hair.  It did!  Thank you Dermablend.  I had hoped that the little sleep I had the night before was enough to lessen the inevitable dark circles under my eyes.  It wasn’t!  But there’s a reason concealer was invented.  I wonder if my boots had too high of a heel to spend the day in.  They weren’t. They never are.  

Although my male side can easily shake off how HE looks and it’s not… HIS problem, it IS Hannah’s problem, if you know what I mean.  Hannah’s the one who has to contend with a middle age man’s face and body.  SHE is the one who puts on a cinched corset to create a more traditionally feminine frame.  She’s the one who does color correcting to balance out any hint of facial hair.  It’s like leaving a huge mess for someone else to clean up.  BUT! that someone else is, well, me.  Do you know what I mean?  I bet you do.

As I got ready on Saturday morning, I couldn’t help but think about how I felt the night before as I when I was getting my haircut.  I felt and looked like death (yes, still waaaay overly dramatic) the night before but now I had to attempt to create a beautiful painting on a worn out canvas.  Some men use WD-40 or alcohol to deal with their problems, I use a corset and foundation.  Thankfully between my makeup artist, my outfit, my hair, my breast forms, and my attitude, everything somehow fell into place.  I looked and felt cute and was ready for the day.

I spent most of the day shopping and of course in a mall and in stores there are mirrors everywhere.  I can’t help myself from looking into one whenever I see it.  When I am unsure of how I look, I look into my reflection to, well, decide.  If I think I look cute, the mirror will confirm that.  If I am feeling ugly, I use a mirror to see if I am still ugly.  I am arrogant and insecure, usually at the same time.  Thankfully I am letting my reflection dull my sparkle less and less these days.  I don’t think I am looking BETTER as time passes, but I am feeling less critical and happier with how I look.  Of course, accepting yourself is a BIG part of this.  

How we move through the world (or the mall) is usually a result of how we feel, and often times how we feel is impacted by how we look.  YES! it is shallow but I don’t know about you but when I feel AND look cute, I STRUT.  My head is held high.  This is a wonderful feeling.  But there have been just as many adventures when I don’t feel cute and my head is bowed a little as I go throughout my day.  It happens.  It will continue to happen.  As I was getting my haircut I wondered how I was going to turn THIS into a cute girl the next day, especially when I had a long day planned.  I still felt like I looked like death the next day, but with coffee, lipstick and a razor in hand, I started to come back to life.  Going from one gender presentation to another is often a rebirth and that morning was no different.

I don’t think I looked amazing or anything that day.  I knew I would be doing a lot of shopping and I knew the day was going to be cold and the sidewalks were icy.  I knew from experience that five inch stilettos and slippery sidewalks are not a good combination.  The weather and the planned events for the day shaped my wardrobe.  I wore a cute sweater, a black leather skirt, and black knee-high boots.  It was a cute outfit and thank goodness it looked cute on me.  That’s not always the case.  AND! I felt cute.  Three for three.  The day started with a makeover and I spent the day running errands, getting coffee, shopping (panties, jewelry, sparkly heels, and a few dresses!)  It was lovely.  

It takes a special kind of bulletproofness (I know, not a real word) to live your life or even get through the day without someone impacting you in a negative way.  Adventuring out en femme takes a certain type of balance when it comes to noticing the people around you.  On one hand I am SUPER paranoid about anything I do and anywhere I go.  I need to keep my heavily mascaraed eyes wide open to make sure I don’t see anyone I know.  I am also watching for those who might want to cause trouble.  The pointers, the laughers, the haters.  If I notice anyone paying TOO much attention to me, well, I need to be aware of that.  We need to be constantly on guard.  I do believe paranoia protects us.  On the other hand, I need to go about my day and live my best life without wondering what others think of me.  Sure, someone MIGHT stare at me in a less than friendly manner but MOST of the time I tune them out.  But sometimes it gets to me and I get a little self conscious.  

This was one of those days when I was so comfortable and very much in my own little world that I didn’t think ANYTHING would rain on my one t-girl parade.  This rare feeling is usually a mixture of feeling cute (I know, super shallow) and feeling so content and at peace.  It’s been a stressful year (26 days into 2022 and it’s ALREADY stressful) when it comes to work and it’s been hard to step away from the endless barrage of angry and urgent emails and meetings.  But for one day I was able to tune it all out.  This feeling was… well, it felt like a gift, in a way.  That morning I looked disparagingly into my mirror wondering how I was going to a dilapidated building into Cinderella’s castle.  I wondered how I would be able to strut confidently through the mall when the work week had its toll on me.  But makeup is magical.  The right outfit can do wonders.  I am not going to apologize for being superficial.  You get it.  You can relate.  

Everything I did, everything I wore, everything I bought that day was for ME.  I don’t want that to sound selfish but it’s true.  I don’t spend time wondering what some random dude at the mall might think of my outfit.  I didn’t care what other shoppers might think as I picked out new panties.  No one should care about these things.  And! since I didn’t care what others might think, or were thinking, I certainly didn’t need anyone’s affirmation.  That doesn’t mean I don’t like a kind word or a compliment, though.  A girl at a shop told me she loved my skirt.  Another girl at a different store complimented my makeup.  Even some random guy approached me and said I looked really good.  All these words felt sincere.  I sometimes have a hard time picking up subtleties but Hannah’s sincerity-detector runs high, hot, and hard.  If someone pays her a compliment I immediately scan and analyze it for sarcasm and cruelty.  Maybe I was delusional or wrong or annoyingly optimistic, but everything checked out.

After a long and wonderful day, I returned home and looked in the mirror.  My foundation was still strong but it was a long day and dark circles were beginning to be a little more noticeable under my concealer.  I looked like a girl that just spent the entire day shopping.  Transitioning back to boy mode (because it is a bit of a transition) comes with, at least for me, some regret, sadness, but contentment.  Not because I feel that she is my “true self” but because when I leave Hannah’s world of shopping and avoiding responsibility, it means I am making my way back to a world of meetings and stress.  But I like my boy life so it’s not as bad as it sounds.  

I look at my reflection and I see Hannah remove her wig and something so simple has such a significant impact on… everything.  I have crossed the threshold from one gender presentation to another.  I am in limbo, I am in the land of in-between.  The process I started early, early that morning begins to be undone.  My boots are unzipped, I remove my jewelry.  I slip out of my skirt, I take off my sweater.  I take out my breast forms, my stockings are put back in with my hosiery.  I undo my bra, take off my panties, and finally my gaff.  I am still in full makeup but I peel off my eyelashes and wash everything off.  Even though this can take a bit of time, much of my eyeliner, mascara, eyeshadow, blush, lipstick, lipliner, highlighter concealer and foundation start to disappear with the first wipe of a makeup removing cloth and water.  I clean away the remaining, stubborn traces of mascara.  I put on new panties, and boy clothes.  He has returned. My wife and I catch up on each other’s day while we have a late dinner.    

The next morning I wake in a nightgown, dress in leggings and cozy clothes, have a little coffee and think and reflect on the day before.  It was a good day.  We don’t get enough of them.

Love, Hannah

3 thoughts on “A Good Day

  1. To me dressing is fun and an escape from reality too. Of course, it is a sexual turn on as well. I can certainly understand and identify with what you are talking about. I think that we cross dressers are fortunate that we do it and I think a lot of guys are missing out on the thrill and fun involved in doing it. I think you look pretty good and I envy that you do what you do.


  2. Hannah, You are an, observant, thoughtful, and self aware person. This is a lovely, deeply felt, and meaningful essay. The world, as a big physical place and a big social place, holds a great deal of harshness, but it also holds, or offers, a great deal of enjoyment and even levity. I look at many web page images of trans women, cross dressers, gender fluid persons, et cetera, and the range of emotions that are expressed in the images is interesting. There are the ‘angry’ crossdressers/gender fluid/trans women, there are the ‘happy’, there are the ‘scared’, the ‘non-chalant’, and the ‘self absorbed.’ Everyone deals with, and presents to the world, as best they can. Like you, I try to enjoy the good things and stay away from the bad. Keep on rolling and enjoy the fact that you are a good person in many different ways.


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