Thursday, March 19, 2015

A Cross Dresser's Moment of Self Discovery- Shannon's Story

Everyone has their own story and journey. Here at Glamour Boutique we love hearing from our friends and customers on their own personal ventures as a cross dresser. Some people dress only in their homes, others go out and are very comfortable in doing so, some get to dress very often, and others only a few times a year. Throughout each individual's story there is a moment of self discovery and we love when we get to hear that from our customers. It will always be a work in progress and we hope that hearing other cross dressers stories will help you along the way and will show you that everyone has struggles of their own, whether it is how to walk like a female, doing make-up, or just fitting in. Shannon kindly shares her story below.

-Shannon Freeland's Story-

 Hi all – I’m Shannon, and I’m thrilled to be here on the pages of!  I first started dressing at an office Halloween party years ago (yes, Halloween – we all have those stories, don’t we?). A friend applied the makeup early that morning. We paraded around the lobby, and the looks I received amazed me.  I felt so free and wonderful as my outer self was revealing my inner self – a real moment of personal discovery.

I am unable to apply makeup myself.  Each time I dress, I go to a professional for my makeup.  I hope to take lessons soon, so I won’t be as dependent.  
My makeup artist does a phenomenal job though, and I wouldn't be Shannon without her.  She wants to help me to learn, and I will welcome that assistance. One of my challenges as a cross dresser is buying clothes but I think I have figured out my method. To avoid awkward stares or rude comments by salespeople, I usually show them some photos first, to establish some credibility.  Once they’re aboard, they’re excited to help me and I actually have fun!

Shannon as Ariel for Halloween
My own personal growth and confidence in being Shannon has come from where I can reveal myself in this way.  In the past, it was only during Halloween.  Then it blossomed into going to special events.  Still, there was something lacking – I wanted to “blend in” with the crowd.  For me, this has meant being at restaurants frequented by typical folks, not catering to any particular type.  When I get the smiles, or even no reaction (better than scorn, wouldn't you say?), I feel like I’m fitting in, and that’s the best feeling in the world.

While I always feel like Shannon, I am not Shannon all the time -- maybe once a month or so.  Recently, I went to one restaurant where the waiter has only known me as my male self for years.  He was thrilled to see the transformation – in fact, when he set the plate down, what excitement when he said, “For the lady.”  I loved that!  Here’s a fascinating piece of psychology for you. One day I was walking through a mall as my male self.  As a lady passed me, I thought, “She doesn't realize I’m in disguise!”  I was shocked to hear that inner voice, as I felt, YES, THIS (the male clothes and face) is the costume – Shannon is not.   A total reversal.  The everyday look is the disguise.  How many of you feel that?  Many of you, I would guess.

I found my best makeup artist just over a year ago, and she developed my “essence” as Shannon – she even suggested that my hair be red, which shocked me but I’m so happy I listened!!  When I first saw myself in the mirror, I cried.  I saw my mother’s face in me for the first time of my life.  I did not see my face looking back at me – a brand new person emerged. It changed me.  THEN . . . after taking the makeup off that night, the following day I cried for over an hour.  Deep sobs.

I do not wish to be an “ordinary” person –I want to feel extraordinary. At that moment I felt that the pumpkin had dropped off Cinderella, and all was gone forever.  But this fairy tale has a happy ending, for me and I know, for you.  My makeup artist has stayed with me ever since, and she creates Shannon for me.  I will learn.  Please know that YOU, too, through the marvelous products and advice offered by, you can be the amazing person you’re meant to be too.
Happy dressing!!



We hope you enjoyed Shannon's story and encourage you to share your own experiences or thoughts below. We all have our moment of self discovery. In Shannon's case her real moment was when her make-up artist transformed her into a beautiful woman, and of course when she realized that her male self was her real disguise. When you have these eye opening moments it is like your whole world shifts and you finally feel whole.

 What was your moment of self discovery?

Related Articles: 
Cross Dresser Make-Up Tips
Cross Dresser Shopping Tips


  1. i loved the movies 'kill bill' and at the end 'bill' [david carradine] says something to the effect

    all super heroes have to do something magical to change out of their everyday lives

    except superman...

    superman is always superman and has to suppress people realizing it

    moral there :)

    loved your story shannon

  2. Very interesting. Thanks for sharing that revealing glimpse. Hope you can feel free to be all of you, all the time.anon, no, pvc!

  3. Beautiful story from a beautiful woman. I'm very impressed by your strength and hope that you can put the male disguise away for good at some point. ;-)