Ask Hannah!

I decided I wanted to try wearing makeup and wearing women’s clothing. I am married and so far my wife is very supportive and even did my makeup last weekend! I ordered a few clothes on En Femme ( thanks for advice) and may get a wig soon. My question is how long did it take you to “like” how you look as a woman? I fear it’s going to take forever and I feel so old!!

Hi!  It sounds like you have a wonderful wife.  
Being en femme is a humbling and empowering experience.  I think some of us feel that when we have all the “right” items (wig, clothes, makeup) everything will magically come together and our reflection will show the side of us that we have been yearning to see for countless years.  Our first glance into a mirror can create a number of different feelings.  Sometimes we can be amazed at the beautiful girl in our mirrors, sometimes we are crushed with disappointment.

And sometimes we see the potential.  Not quite how we want to look, not quite how we imagined, but…  it’s a start.

When our reflections are not everything we hoped it would be, then we need to make a decision.  We COULD give up, but let’s face it, that’s not easy or likely.  This is not a side of us that goes away.  But I do get it.  It might seem hopeless, our worst fears are realized because we look exactly what we were afraid of: a man in a dress.  Crossdressing takes time, it takes money, it takes patience.  Don’t like how you look in makeup?  Pay for a makeup lesson.  Try a different foundation.  Watch more tutorials.  Your dress doesn’t fit?  Get your measurements and get an outfit that is in your size, not the size you’d like to be.  Stumble in heels?  Strap on those stilettos and practice, practice, practice.

The first time I was completely en femme, which was about ten years ago, I was enraptured.  I didn’t look like a man in a dress and a wig, I was unrecognizable.  At least that’s how I thought and how I felt.  Of all the things I was thinking in those first moments I think the thing that was the loudest was that I could see something I could work with, if you will.  I was on cloud nine the whole evening.  

I quickly learned that dressing up is a different experience and comes with different feelings every single time.  There are times when I will start dressing and feel blah about how I look but then when I do my makeup my attitude improves and turns things around.  The opposite is also true.  I might have a killer dress but sometimes my makeup just doesn’t come together and kills my excitement for my outfit.  These experiences and fluctuating feelings do not stop.  So many small things impact how we feel about ourselves and when I am en femme I am filled with many small things.  My forms, my pads, my outfit, accessories, makeup, hair, my body shape…  It all needs to come together.  It’s like baking a cake, I suppose.  If you don’t have the right ingredients it’s just not going to work.  

The photo on the left is me feeling cute, but not looking cute. The photo on the right is me looking cute, but not feeling cute

AND!  Sometimes everything can go right but sometimes we just don’t feel it.  We might look cute, but we don’t feel that way.  How we feel will win out (for good and for bad) EVERY SINGLE TIME.  I have dresses that I feel are just kind of… meh but if I am in the right mood it becomes the cutest dress in the world.  Of course the opposite is true, too.

So, to answer your question, I more or less liked how I looked right away, but that doesn’t mean I always like how I look.  I still have plenty of times where I feel I look like a man in a wig.  

Love, Hannah

Have a question for me?  Oh yes you do.  Ask me here!

3 thoughts on “Ask Hannah!

  1. Interesting question and response. Like Hannah, just over a decade has passed since I finally dared allow myself to dress completely “en femme”. After decades of indecision, that moment that I had both feared and longed for finally arrived. Daring to inspect myself in the mirror, I realized I had a lot of work to do on my make up, hair, foundations, etc. I recall recognizing myself in that mirror and liking myself in a way I never had before. At that moment, I knew “I can do this!”.

    Liked by 1 person

  2. Ah yes the dreaded look in the mirror.
    Yes those of us that have stepped out the door know it all to well.
    Many times I’ve looked after putting on the final touch of lipstick and thought omg I will be clocked so easily.
    Then I think well I’m dressed I’m happy and you know what I don’t care what others think.
    If I conduct myself like I belong then most never bother, oh sure they might do a double take or smirk but I am me, this a part of me that I’ve chosen to express because well because I have to.
    So yes we all go through it, checking the makeup and all such things and the more you do it the better you get but sometimes it’s not always perfect but then neither are some cis women

    Liked by 1 person

  3. I have to agree unless I do the entire outfit and the whole ensemble looks good and my makeup is the best I can do I’m not happy


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