Many of us have shared a lot about ourselves here and perhaps on other safe sites where we connect with like minded people. Have you ever told anyone who you really  are on the inside?  Someone outside this comfortable setting?  I did that a couple years ago and it was a very liberating, exciting experience.  I have been out dressed with other ladies in a controlled environment, in a venue that was safe and accepting, where I was surrounded by people who had similar stories and backgrounds to mine. However, sharing this deepest part of me with someone totally unrelated to this was a new experience.

I was at a business conference in Arizona.  I was, obviously, dressed in male mode when in public the whole time.  I met a young lady at, of all places, a bar.  Since we were both there for the same conference, we had lots in common so conversation was easy and very basic at first. She was MUCH younger than me so the talks were purely business and eventually more along the lines of how old friends talk.  One evening we were sitting at the bar talking and the conversation became considerably more personal.  She shared a time when she had done something very daring.  She asked if I had anything along those lines to talk about.  I said “yes, but you will think much less of me after I tell you my secret.”  She promised she wouldn’t and after a bit more coercing on her part, I told her that I was a long time cross-dresser and that my name was Ashleigh.  She asked if I had brought clothes with me.  I replied “of course.”  She then asked me if I would dress for her.

Now the scary part.  We went to my room where I went immediately into the bathroom to change.  When I was fully dressed, I came out expecting the worst in regards to her response.  I was amazed when she cried and told me I was beautiful.  She asked about the logistics of dressing to be convincing.  We talked for quite a while, and then it was time for her to go back to her room.  We snapped a quick “selfie”, exchanged contact info, and then she asked me to walk her back dressed as Ashleigh.  How I wish I could have!  Alas, too many business associates know me as a male so that was not possible.  We have kept in contact since then via email and text.  She made sure to tell that she had me listed in her contacts as “Ashleigh Marie.”

The moral of this story (to use an outdated cliche) is:  there are many people outside our sphere of influence who are accepting and understanding.  We often fear that we can never tell a soul for fear of the consequences.  But, that’s a topic for another article.


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I am, like so many others here, a long time crossdresser. Now, as I pass 60 years old, I realize it's not going away, and I don't want it to. The more I get to know Emily, the more I like her. 😉
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7 years ago

Thank you Ashleigh
I struggle with this alot. I have been trying to find away to bring it up to a nieghbor. Iknow that she knows about me but I have never really actually told her. She has seen me outside leaving or coming home. I guess that i am afraid of what she will say. Thank you for some ideas

Sallysim' class='avatar avatar-64 photo' height='64' width='64' />
7 years ago

Lovely story Ashleigh, and so very true. We always fear the worst, yet many of those fears are unfounded, I find the younger generation and women are far more accepting and understanding, many even encourage us as transgenders or crossdressers to be more open and be our true selves.
Thank you for sharing your experiences with us all here , I find it very inspirational.

April (Pacific Princess)
Active Member

Wonderful story Ashleigh. Very brave of you. Not just to share your secret, but to dress too. It is amazing how most of what we fear in life turns out to be nothing really to fear at all. I have been lucky to have nothing but positive experiences so far, and women in general are much more accepting than men.

Thank you again for sharing such an inspiring story!


7 years ago

Good for you Ashleigh. Just a little confidence goes a long way and does pay off on occasion. I too have come out to others and felt a big load off my shoulders in those relationships .

Danny L white
7 years ago

Thank you Ashleigh it’s a wonderful feeling to get out of are comfort zone.

6 years ago

Ashleigh, Thank you for posting this. I’ve also discovered that my assumptions are incorrect when I think someone will react negatively to my sharing this part of myself with them. I’ve not shared with anyone in my “real" world other than my wife. And I stopped short of a full disclosure with her, because she did begin reacting negatively. I understand now that she was reacting out of fear. Regards, that is another story. I travel a couple of times a year on business. When I traveled last May I brought a couple of outfits with and was prepared to… Read more »

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