As I get older, I am becoming more and more determined that I should be true to myself. That being said, I am still very cautious about who I share my feminine side with. As a result of my personal confidence and acceptance of who I am, I recently told the two young ladies who work for me about myself. I have since received enormous acceptance and support from both of them. It became a necessity for me to tell them, as wearing makeup every day was a little conspicuous and I felt more comfortable with them knowing. I also dress 90% female. For example, ladies jeans, socks and sneakers with a generic polo top. Mostly, only I know the clothes are women’s and the general public really don’t notice.

Once I had told my staff, one of the girls said she that she had noticed the makeup before, but didn’t want to say anything. She has become my biggest supporter since that day. We now share tips about clothes and makeup. I now also have someone that I can confide in and share my struggles of being a cross dressing business owner, in a small town. We are become good friends and I send her snap chat photos and receive encouraging replies. Recently, she cleaned out her closet and gave some of her old clothes to me. Granted, she is much younger with different tastes, but none the less, I was able to find a few things that I enjoy wearing. She gets the biggest kick out of seeing me come to work in a pair of jeans that used to belong to her. One day, she even asked to borrow my lipstick that she knew I kept in my desk drawer. I believe that I have a very special friend in her now. For my birthday this year, I was so surprised and delighted to receive a Victoria’s Secret gift card from her. Just the Best Birthday Gift. Ever!

I am a gym owner and often start my day with a work out along with my associate before the day begins, something we do often. I almost always, always wear a bra under a tank top – my workout shirt. Sometimes the strap will show, and I often just let it show when I am in the right mood. However on many occasions she is gracious enough to discretely tell me and to save me from embarrassment.

All this brings me to the real subject of this article!

We work so hard in trying to be sure we keep our ‘private’ side hidden. When in reality, the thing we want most of all, is for EVERYBODY to know. Telling and showing people, can bring massive amounts of personal joy and satisfaction. Few of us really want to stay hidden in the closet or only dress in the privacy of our own homes. And a common thread that I have read in articles and posts, about having the courage to go out. Once you have found the courage and confidence to do that, there is no turning back. The best thing that can happen for you is to find a local support group and take part in their events. I have been out fully dressed on a number of occasions and find it gets easier every time.

And so, to the final point! We can find ourselves living in a state of dilemma. We fear people finding out our ‘secret’, yet we want to tell the world about the real person that we are, some days. I can tell you from personal experience, that having one or more people that you can confide and share with, who you really are, is the one of the most liberating and energizing things that can happen to you. Make no mistakes, it is quite scary to tell people. For myself, I have found that the risk is out weighed by the worth of the reward.

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Ashleigh

I am, like so many others here, a long time crossdresser. Now, as I approach 60 years old, I realize it's not going away, and I don't want it to. The more I get to know Ashleigh, the more I like her. 😉
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16 Comments
  1. Brienna Dennouix 4 weeks ago

    Thank you for sharing this Ashleigh, it is good to know that there are people out there that understand and are supportive. I just started on this journey of accepting who I am and what I feel inside me so I don’t think I am ready to out myself yet.

    Brienna

    • Author
      Ashleigh 3 weeks ago

      The best advice I can give is, baby steps. Take the time to enjoy each part of your journey. Everybody moves at the their own pace. You’ll know if (and when ) the time is right for you to move forward.
      Thanks for the response!

  2. Shannon Fox 3 weeks ago

    Hi Ashleigh it is good to find support from someone. The first person I came out to was a girl in my work and she fully supported me and this really helped me on my journey. Hugs and kisses.
    Shannon

  3. Jess Jones 3 weeks ago

    I posted to my femme Facebook last night that I told the flight attendant on my flight home from Boston. Her name was Jessica too and I wanted to see if she would let me have one of her name tags (I am trying to collect them). I had to tell her WHY I wanted it and simply showed her a picture on my phone. She exclaimed, “Is that you?!” and I just nodded. My heart was probably pounding more than the night I told my wife. To tell a total stranger, that isn’t a store clerk (something about store clerks doesn’t scare me), was terrifying. I actually spent the entire 2 hour flight practicing asking her for her name tag. Wonder what it will be like the next time I tel someone I don’t know……

    • Author
      Ashleigh 3 weeks ago

      That must have been a fun conversation!

      • Jess Jones 3 weeks ago

        It was, unfortunately, too short. But when I saw her going through pictures on her phone of her posing on the empty airplane I figured, “this girl will be cool if I ask her for her name tag, at least once I show her pictures of me as Jess”. Still no luck though. Too bad.

  4. Kara Kelly 3 weeks ago

    Thank you for this wonderful article. It gives me encouragement.

  5. skippy1965(Cynthia) 3 weeks ago

    Amen Ashleigh. I stealth dress the way you mention at work too-but i work at a major mortgage corporation HQ so unless/until I decide to transition, it will go no farther at work. ! I’m certain SOME at work notice (you can see in my pics how long my hair is and i recently got my ears pierced)but no one at work has said anything. My siblings and adult kids and nephews and nieces know and a couple friends as well. I have gotten out and about much more in the last few years. Thanks for sharing your story and its excellent advice!
    Cyn

  6. Winnie 3 weeks ago

    Very nice article.
    The most favorite words are …” We fear people finding out our ‘secret’, yet we want to tell the world about the real person that we are…”
    It’s totally what’s inside me.

    Hugs with Loves,
    Winnie

  7. Terri 3 weeks ago

    Good advice Asleigh. What is right for one person is not right for another. I just can’t bring myself to tell my grown children. My wife had known a long time and wants no part of my femme side.

  8. Amanda Patrick 3 weeks ago

    Hi Ashleigh,

    You are right Once you have been out It is a little more difficult to stay at home. I have been out a few times and always look forward to the next time which is coming up shortly. As far as People knowing My wife knows and so does one of my Children. No judgement on there part. You are right that we want our private life to stay that way but at the same time we want the world to know who we really are. Some times I feel I want to shout it out to the world.

    Hugs,

    Amanda

  9. Lisa 3 weeks ago

    Hi there Lisa here I am new to this group it is lovely to see the encouraging stories I am getting ready to go onto HRT and I am so excited about it I have been cross dressing secretly for a while. I just got my first pair of pumps yesterday wow can’t believe how comfortable they are miss having them on during the day couldn’t wait to get home to put them on

  10. Janine 3 weeks ago

    I haven’t told anyone where I work but this past summer I went to the Keys and there were quite a few crossdressers there where I was staying.
    I went there for the purpose of dressing enfemme for the whole time I was down there and on the first day I met someone who I confided in about my secret life.
    It turned out that she was down there for the same reasons I was and we became friends and talked for hours on end about our feelings and thoughts on crossdressing.
    You are right about after telling someone about it that it’s accepted by more people then I thought that it would be.
    I live in Florida and my new found friend lives in Atlanta.
    We text and email each other almost every day. We plan on going to Las Vegas for New Years this year.
    I am not sure if I will ever tell my coworkers but maybe someday I will.
    Good luck with your life and business.
    Hugs to you and your friends.
    Janine

  11. Kim Paige 3 weeks ago

    Thanks Ashleigh! Very inspiring!

  12. Stephanie O'Sullivan 2 weeks ago

    Hey Girls, I too have been letting my long hair down, and a couple of my female customers have been very supportive of my femme side, even giving me some of their extra clothes. I wore a very pretty dress one gave me to her Thanksgiving dinner, her husband thought I looked nice!
    I get tremendous Love and support from mostly the women I see weekly at the Farmers Market and it fills my heart with Joy to get that Love and attention.
    Love & Light,,,,
    Stephanie O’.

  13. Tsbella Swallows 2 weeks ago

    Mom caught me at7 in a dress again at 10 and asked me why I told her I feel complete this way Sat with my dad they excepted me that way got me girl clothes my brothers love me as their sister grew up in skirts and dresses after school the neighbor boy seen me and hung out with me till they moved away 5 years later he was my first male kiss and other stuff now my wife knows stepdaughter I told both of them they love it my best friend of20 years now found out last month he seen me dressed in town with my daughter and a couple guys he’s ok with it that is if grabbing my ass when I’m in a skirt which is all the time he always asks if I’m dressed before he comes over ? Maybe I should see if he likes to play my wife is ok with me being bi she is bi curious herself and also if I sleep with a man she is there joining in she tells me to go for my friend I don’t know yet but girl enjoy life we all deserve it

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