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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Brienna Dennouix
4 years 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.


Brianne Rhodes
Brianne Rhodes
4 years ago

Me either but a side of me wants to look bad to just walk out the front door in a miniskirt and high heels feeling very sexy and alive! Of course I don’t habe the courage to do that now but the other night I sent my friend a txt telling her all about it just wanted somebody else to know as well. The next morning when I got up she never mentioned the txt or anything still acts the same toward me so I guess its all good

Shannon Fox
4 years 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.

Jess Jones
4 years 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… Read more »

Jess Jones
4 years ago
Reply to  Emily

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.

Kara Kelly
4 years ago

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

skippy1965 Cynthia
Trusted Member
4 years 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… Read more »

4 years 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,

Terri' class='avatar avatar-64 photo' height='64' width='64' />
4 years 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.

Amanda Patrick
4 years 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… Read more »

4 years 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

Janine' class='avatar avatar-64 photo' height='64' width='64' />
4 years 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… Read more »

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