Like most of us here at CDH I began cross dressing at a very early age, 11 or 12 years old and fell in love with the way I looked and felt when I dressed. I experimented with makeup a lot. One day I would use some foundation, concealer, powder the next day eye shadow, another day lip stick and so on. Seems like no matter where I was I would always find someones makeup and get into it sometimes even taking it.

By 13 I had makeup down pretty good. While other boys went and did what young boys usually do, it seems like I was always staying home playing dress up for reasons I did not know of at the time. Anytime my sisters and mother were gone I went into experiment mode putting on makeup and getting dressed into something of my sisters. I felt deeply obligated to do this and came to a conclusion that I loved the way I felt and looked so much more than how I looked or felt as a boy.

Was I a strange kid? Why was I so infatuated with dressing up as a girl in any my alone time. I used to sit in class at school and look around at other boys in my and wonder if I was the only boy who did what I did. I think I came to a conclusion that I had to be the only one thus separating myself even more from them and other kids. One day at the age of 16 I got up the courage after drinking some of my mothers wine to get dressed up and go outside for a short walk and I remember how every minute was so fearing yet exciting for me it was. That day was the day I knew I wanted to be seen even more and I wanted to continue evolving.

Exceptional Voice

I dressed nearly everyday, trying new ways for makeup, choosing what to wear, doing my hair in different ways, practicing how I walked, how I talked and deciding what look I loved the most. Where I live the age to enter a bar was 19 but when I was around 17 (because I was defiant and never paid too much attention to rules) I got all dressed up one evening while everyone was gone. I had bought my mothers car when she bought a new one thus having my first car. I had found the only gay bar there was at the time and had tried to get up the courage to walk in. Hey at the worst all they could do was not let me in right. Just down the street was a little market and I pulled into the parking lot and parked. I was nervous as hell could have it. I’m sitting there trying to figure out a way I might be able to get in unnoticed when a car pulls up beside me.

There was a guy sitting in the passenger seat but it was the driver that caught my attention. Without a second thought I quickly recognized the driver as being a obvious drag queen. As I sat looking at them she looked back at me then and smiled with a little wave attached. It was definitely striking evidence that we as cross dressers and drag queens will always be able to recognize another. She then waved her finger for me to get out of my car and come over to her in which I did. After a brief introduction and compliments to one another I came right out and told her what I was attempting to do which was go into the bar down the street and she well get in I’ll take you there.

Without hesitation I went back to my car and locked it up and got into their car. We dropped the guy friend she had off at his house and proceeded to the bar. I was so nervous I was shaking. Her and I walked right past the man who was standing at the door to checks, he didn’t even look at us twice. I was in and within a minute felt like I belonged there. She and I became friends fast and after some conversation it was though we had known one another a life time. Over a short period of time we established a true friendship and she became like my best friend as well as a mentor. We began getting dressed together and going to the bar where I was making plenty of friends.

January 2021 Live Session - cdh

I won’t go into some of the under ground activity that came afterwards after I had begun to meet people in the gay scene but I will say I did get involved deeply. I was seventeen almost 18 and had come to be friends with much of the people there. In wrapping this story up it’s safe to say I had found my new home, my life was going in the direction I had wanted it to go in and I loved every minute of it. So it came to be that not too long after I established what I had behind closed doors was then a way of life. But however, today brings me somewhat confusion of who I am.

With cross dressing I can go out in public dressed and be recognized as a guy dressed as a woman or living the life as a woman. But am I a woman? No, am I transgender wanting H.R.T. and re-assignment surgery? No is my answer to that question as well. Or am I just a drag queen that loves to get dressed up and go out to the bars or clubs and be involved in the gay scene? Yes I do like that part of my journey. But is it enough to quench my hunger or thirst for being feminine? I believe the answer to that question remains all the way back to when I was young and dressing in silence behind closed doors. I will soon be 57 years old, I think it’s a little too late to rethink my life so allow me to make my very last big decision and that is to continue just being who I am, being me!

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Jewelry Artisan, cocktail waitress, part time escort. at Emerald Club, Shuckeys Club
Very simple yet at times complicated but I always prevail. I have been out since the young young age of 17, both CD, Drag and sexual orientation. My mother kind of figured out allot of it before I came clean one morning. I love drag, I don't really perform like so many queens do, I guess unless you piss me off I'm pretty silent. Been in only two serious relationships and loved them both with all my heart (this is the area I mentioned in the beginning where it get's complicated). I am a strong supporter of LGBTQ and gay rights. Why can't we all just get through this world together? Life is short so I try to live each day like there will be no tomorrow, because there may not. I am so easy to get along with it's crazy. However, there are some people who bring out the worst in me. When that happens go the other way!

Latest posts by Jackie (see all)

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4 years ago

Thank You Jackie for a wonderful article I am so happy you have found your true self. Something we all must do in life.

Pippi Long
4 years ago

I love your story Jackie ! i think most of us here feel the same way .I know i do ! Im 51 and still coming out little by little . PIppi has become a big part of my life , she defines me and who I am She has been part of my life cents child hood . Im not gay but i love to dress everyday in some way its still confusing sometimes but i still feel so feminine and the need for me to express these feelings are so overwhelming sometimes ! stay strong sweetie hugs, and… Read more »

4 years ago

Love your story. I wasn’t lucky as you but found once I got into the bar my new personality took over( also with a bit of relaxing liquids to take the edge off. I found it amazing you were able to get enough courage to go out at that age and to be able to find a friend to make you at ease in the beginning. if only we all had a mentor type situation like that. I believe it should be easier for todays kids to move forward with there transitions. Most of us toil away are dressing alone… Read more »

4 years ago

I really can identify with your story too Jackie and ty for sharing it with us. At 15 I was wearing my sisters clothes and mothers wigs when home alone and knew immediately this was natural to me. Along the way I frequented the gay bars too and passed off as a drag queen until I realized I needed something more and found an incredible journey since then. Hugs honey

4 years ago

It’s interesting to me that you use the description “drag queen”. Here in Australia that term usually conjures up images of over-the-top, heavily made-up theatrical performers, a la ‘Priscilla, Queen of the Desert’. Until more recent times that was what many people though crossdressers all looked like. After I’d told my wife about me being a crossdresser I tortured myself by imagining what she saw in her mind’s eye. Finally, many months after I’d come out I had a professional makeover and she asked to see the photos. Suddenly I was terrified that she’d see the ‘drag queen’ I imagined… Read more »

Savannah S
4 years ago

Love your story… I have not found the courage to go to bars other than haloween.
My beautiful wife totally support me in my dressing.
Encourages me to be who I am as she says. And I am both sides. Truly male in male self, but truly feel at peace and complete when dressed.
I wish I could he more bold in going out and be in public more. But always the fear of being “found out” by someone I know …

4 years ago

Jackie great story. I can identify with a lot of it especially the make up. And going to the clubs sounds a lot like you at the bar. Jackie I love talking to u here. And you should know you are not alone. Love ❤️ ya.

4 years ago
Reply to  Jackie


Vera jane
4 years ago

Thank you for a ‘straight from the heart’ , honest account of “Jackie Wild”……
Hugs , Vera Jane

Michelle B
4 years ago

I have not been on here (CDH) for a while, but when I do, I read this story of a great gal opening herself up. I am proud to be connected with this site and to be your friend here. You go girl!

skippy1965 Cynthia
Trusted Member
4 years ago

Great story Jackie! I’m still working out exactly who Cyn is and what her path and destination will be but in the meantime I sure am enjoying the journey!
Thanks for sharing your inspiring life!

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