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.

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.

EnFemme

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.

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!

EnFemme

More Articles by Jackie

View all articles by Jackie
The following two tabs change content below.

Jackie

Jewelry Artisan, cocktail waitress, part time escort. at Emerald Club, Shuckeys Club
It's safe to say that my life & lifestyle" were chosen for me before I even knew the plan! My belief has always been that I / we didn't choose our lifestyle but that we were born this way. I guess there are many who don't see it this way and make many attempts to fight or change our fate. I however did listen to it and began to follow directions at a early age. For me as with so many other Cross Dressing, Drag and LGBTQ+ lifestyle began around 8 years old. Well LGBTQ+ followed soon after. My sexuality was confirmed at 15 after having my first encounter. It couldn't have been more apparent. Answers to my own questions I carried with me for some time were answered that day. My coming out debut was like a huge weight lifted from me immediately when I stood before my mother and sister's and confessed everything. All of they're suspicions were brought to life. Getting into all my sister's things, wearing they're clothes, makeup and everything else they owned I admitted to. I had always thought I was so sneaky and left no evidence. But I hadn't been. They knew all along. There was so much evidence. There were so many times and situations throughout a long course of time had added up and grown in such big numbers it had to have been impossible to keep track. For example all my posessions in my bedroom like makeup, nail polishes, hair tools, my clothing, shoe, boots, pictures and posters on my walls, etc. If anyone who had walked into my room didn't or couldn't recognize that "there was something different about Jackie" they would have been stupid and or very nieve. I always came up with an excuse as to why anyone seen what there was to see in every corner nook and cranny of my room. I did eventually begin to wonder how they really thought. I I had been put on front street and drilled with questions practically on a daily basis. I had slowly become too relaxed and stopped trying to keep everything hidden. Beside the fact that everything had become too impossible to hide. So confessing to all of what seemed at the moment to be so long actually only took minutes to admit it all to be true. Thats as short of my story I can put down to you. I have only a few regrets of mistakes I have made overtime but who I am is not one of them. Enjoy, have fun and be yourself and if you can't do that right now then pretend until you can!

Latest posts by Jackie (see all)

Tags:
0 0 votes
Article Rating
39 Comments
Inline Feedbacks
View all comments
April (Pacific Princess)
Ambassador
Active Member

Love to hear about someone living life her own way! Great story Jackie! I wish I had your chutzpah! I’m working my way up to it though. When I’m going through a bit of a down time like I am now, it’s wonderful to read stories such as this.

Take care hon!
April

debbie
Member
debbie
7 years ago
Reply to  Jackie

Hugs xxx

Xeri Renee Alexia
7 years ago

Enjoyed your story, Jackie. Living in a similarly conservative area I am frightened at the idea of admitting to family and friends that I cross-dress, even if I do so only once or twice a week. As a first-year CD, I often find cross-dressing to be extension of who I am. But with people knowing I’ve always been single and making assumptions about my sex life, the idea that I cross-dress would further justify those said assumptions. If there is anyone else who cross-dresses in my neck of the woods, it’s news to me. A part of me would like… Read more »

Lisa norman
Lisa norman
7 years ago

Love your story! After reading some I feel different because we took different paths but got to the same place: being ourselves! My journey has been a little different but I am happy now! I wish I could go out in public and pass but I look more like I am in the tact squad of a police dept but all my parts from nipples to knees all feel feminine and I dress at home. Being married to a very accepting wife makes it fun and being her lover in bed I feel more like a lesbian or bi chic.… Read more »

stacey s
Lady
Member
7 years ago
Reply to  Jackie

Jackie, Loved your story and I know the hunger I started dressing when I was younger just must of the girls here. I, had the curious side to me also and was with male and so it went. The hunger never died for dressing or for being with a male and I surpassed it for many years married and divorced twice and it was not for my dressing . I, dress manly for the evening and have been out several times. After many years in therapy, which I thought I was crazy and even Bi during my dressing I realize… Read more »

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

Very good indeed. It is so liberating and empowering to share our lives with other like minded people. I always struggled to find someone real whom I can enjoy being the woman… My wife is wonderful who supports me but she does not discuss it or shows much interest in it. I really felt how wonderful would it be to have a friend or a mentor to share the passion with, enjoy being one, going out to clubs or shopping or just a casual walk.

Lovely to hear from you and stay blessed and beautiful.

debbie
Member
debbie
7 years ago
Reply to  Mona.

For sure Mona. you should look for a support group or cd organization near you so as to meet others and do things together on weekends. so exciting hon and worth the effort

Joselin Zofcin
Joselin Zofcin
7 years ago

I truly loved this article it is filled with courage and a strong spirit. This article is an inspiration to all of us ladies . Thank-you very much Jackie you are a very special lady and mentor. Hugs and kisses to all you lovely ladies.
Love
Joseline

Leonara
Ambassador
Trusted Member
7 years ago

Jackie, Thank you so much for the article. As you have read the replies, it hit home to a lot of the ladies including myself. My wife found out about Leonara when she walked in unexpectedly. We talked about it but she requested not to dress when she is around. However a few weeks ago we went shopping and she picked out my panties, cami’s, and stockings. We even had manicures together. I think my CD put a new dimension in our 45 year marriage. Thank you for giving me the opportunity to share my story. I am so grateful… Read more »

Grace
Member
Grace
7 years ago

We have talked in the past and I love reading your thoughts and experiences. As to myself I still dress when I can and have had some great times with another CD. I finally had the date of a life time which resulted in my first experience with oral sex with her. It was excileraring, exciting and all what I had hoped for. I was surprised at how good I was at it and simply want more!

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

New poster here. Appreciate Jacki’s story. At 53 , I finally accepted this beutiful part about me. Robin is a happy girl and she’s been with me since i put on my Mom’s hosery as a kid and loved it. I look forward to reading and contributing to our site, as well as meeting new friends. I’ll post a picture next week as I ordered a a few things last week and it will all be delivered next wek – wigs, a dress, shoes as well as matching PJ’s for my wife and I 🙂

Morgan Staar
Morgan Staar
5 years ago

I dress very conservative to stay under the radar..If some one looks they think ‘Oh cute girl’ instead of stopping and staring..Guess I’ve always feared of being seen as a Drag Queen that wants to be noticed..Its just what I was always taught..but I am learning more and more as I talk to like minded girls here

39
0
Would love your thoughts, please comment.x
()
x
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials

Forgot your details?