Drag vs Cross Dressing, Being Me!

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.

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!

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Jewelry Artisan, cocktail waitress, part time escort. at Emerald Club, Shuckeys Club
Hello I’m Jackie. I had a pretty long bio and decided to shorten it up. Most of you here at CDH know me, those of you who are new to CDH I say hello to you and welcome to a family you won’t know elsewhere. I love to talk so should you feel the need just hit me up, I’m here, Jackie (Wild Child).....

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  1. Morgan Staar 3 weeks 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

  2. Robin Twain 2 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 🙂

  3. Grace 2 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!

  4. Leonara 2 years ago

    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 that I found CDH. Thank you ladies.

  5. Josselyn 2 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.

    • Author
      Jackie 2 years ago

      Thank you so much for the compliments sweetie, they are very appreciated from this end,

  6. Mona. 2 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 2 years ago

      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

      • Author
        Jackie 2 years ago

        Debbie you nailed it with what you said to Mona. It is a awesome lifestyle, it really is and rewarding when one looks in the mirror to see the shining gurl looking back. Gives me goosebumps.

  7. Lisa norman 2 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. I recently got a 3rd opinion by accident. My wife’s daughter came to visit as her husband is in military and overseas. We had already met and bonded because I served 3 tours overseas in my past! I didn’t expect her visit (my wife called but phone was on charger). I was in my hottest panties, a matching bra and camisole; a recent pedicure with hot red nails and also lipstick with some make up! I look up and Angie is in living room! I was freaked at first but her mom had already gave her a heads up..i was apologizing as she told me it was cool as she knew and accepting! I went to bedroom for about an hour and I came out and she was in panties and t-shirt. I was uncomfortable. I knew my wife would be home soon and she told me heck lets be comfortable. I did remove lipstick. My wife got home and made a joke and said one house full of chics. Karen got down to t-shirt and panties and we all ate and chatted. I found out her husband loved Angie to send him her used panties so he could get off in. she stayed with us for a week and I came home from FD and then to intimates and was comfortable with her. She asked me the usual why? And for how long? And I told her! her reply was I make her mom happy that’s all that matters . I found out later Angie did ask her mom if I did hormones and my wife asked why? Angie told her I can barely tell where its at…my wife told her daughter some things come In all sizes and she wouldn’t say the size but no hormones!
    Have I experienced my feminine side with a male? Yes! My ex and I had an open marriage I guess or I was a cuck. I dressed some when her b/f came over but only in panties. Want bore you with details but I did the things cucks do.. very happy to be divorced from her but it wasn’t for sexual reasons. The other guy was a friend in knew from the gym who wore panties and we both noticed each other while undressing.. we were both married at the time and went to his house and he showed me how he dressed. Soon we were dressing together but very discretely. We both decided we wanted to experience what our wives experienced and so you can imagine what we did! He got caught dressed by his wife and got read the riot act so end of that.
    Its great as I am new here and reading and learning. The reason I said I must be a lesbian or bi is my wife and I make love as chics. She is a squirter and multiple but I don’t penetrate her with my clit. This has been going on for 5 years and we change some things around but no other people in our bedroom
    thanks! i am glad i found this site

    • Author
      Jackie 2 years ago

      What more can be said other than kuddos for you. Though your story is a familiar one and similar to so many I can’t really identify with it so much. However, it does sound as though your free and welcome to cross dress in your home with wife knowing and that I bet makes you a very lucky person in the eye’s of thousands. Good luck to u on your journey. Jackie:)

      • stacey s 2 years ago

        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 as my therapist said I was gay and now I can agree . Being with another male or CD is my hunger. this hunger has never left and so Life goes on as I am very selective. Thank you for your story.

  8. Xeri Renee Alexia 2 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 to know, another part fears that person might out me. And because I come from a strict and largely Catholic family and community, don’t get me started on telling anyone from my hometown or family. I find your story encouraging and enlightening. Too bad I live in a community that associates enlightenment with Godlessness.

    • Author
      Jackie 2 years ago

      It is sad Xeri that we do live in a society so damn judging, hypocritical and frightening to be who we really are. I say this because although I have told my story here at CDH (because I feel comfortable in doing so) it has still not been a real smooth path for me. I was fortunate to be given the courage from wherever it was from to step out and begin living my life. Then to have the people who walked into my life at such a critical time was as though (to me) a Divine gift. When you do feel as though you can no longer restrain your secret life to merely yourself you may or will be surprised at who will be there for you and support you! I have a couple of good friends who came from strong religious backgrounds and they are gay as well as cross dresser’s and drag queen. One of those friends thought she had lost her family forever but given some time they all stepped back into her life and all is perfect between them now. No one deserves to be outed, that is a special time for each of us and should be only when we are ready to. Unfortunately that would be in the perfect world. I wish you all the best in your endeavor. If you ever want to talk you can feel free to message me or there are really good decent people here at CDH you can always talk to as well. Take care and I look forward to talking to you sometime. Best, Jackie. p.s., I’m glad you liked my story and hope it helps you in any way.

  9. 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!

    • Author
      Jackie 2 years ago

      Thank you April and I hope that maybe something said gives you your own strength. I don’t know, I believe we all can be stepping stones for one another. God knows I have had real supporting people in my life that have guided me when needed. I think that there is so much to be grasped onto here at CDH. This site to me is mindful that there are Divine Entities out there that can and will carry us when we need carried. I love CDH and I am truly grateful for it’s existence and the people here. I am free most of the time to talk so if you ever want to just hit me up. I always love girl talk lol. Best, Jackie:)

      • debbie 2 years ago

        Hugs xxx

  10. *skippy1965(Cynthia) 2 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!

    • Author
      Jackie 2 years ago

      Thank you Cyn I’m glad you liked it. I trust your path / journey will continue being joyful. I would love talking with you sometime so if you ever have the time I’d like that. Besides that,,,, I still have a puzzle to solve and your suppose to have the clues I need to solve the mystery lol. Jackie:)

  11. Michelle B 2 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!

  12. Vera jane 2 years ago

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

    • Author
      Jackie 2 years ago

      Thank you Vera, I don’t see no sense in talking if it;s not true or from the heart!

    • Author
      Jackie 2 years ago

      I’m glad you liked it Vera. As it is said “The Truth Shall Set Us Free” and though it still is somewhat crazy at times I wouldn’t trade back haha. Blessings, Jackie Wild:)

  13. Jenny1323 2 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.

  14. Savannah S 2 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 …

    • Author
      Jackie 2 years ago

      I think we go out into the public not just when we feel ready (god knows I was feeling what I thought was ready right from the beginning it seems). But I think it has to be harder when one of us lives one way openly and another way behind closed doors for all their lives. Friends come to know us as one way and the fear of being found out that you live another way as well would be overwhelming to say the least.

  15. JaneS 2 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 she would but instead she looked through the photos (and there were many), making occasional observations about outfits. Finally, when the slide show finished she looked at me, took my hand and said “You make a beautiful woman.”

    These days we can laugh at my early fears and we play with words often because I am comfortable with who I am and so too is she. We even stayed in the Priscilla Suite at the Palace Hotel in Broken Hill on one of our trips and she enjoyed taking photos of Jane there.

    Thank you for a delightful story Jackie. I’m not a drag queen, just a bit of a ‘dag’.
    (Alert: non-Australian’s might need to research the meaning of ‘dag’ in that context)

    Let’s have more of your work.

    • Author
      Jackie 2 years ago

      Thank you so much for the compliments Jane, much appreciated. To explain to a degree of my own personal description or difference between when I am merely cross dressed or in drag queen fashion is namely my clothing and makeup and other apparel. My makeup when I go drag can take me up to 2 hours or more and I apply it heavy while if I’m just going shopping or somewhere I can do my makeup in like a half hour or less. Your correct in everything you said, I don;t perform but many of my friends do. I participate in doing lip sync sometimes. I am not sure of how else I can explain the difference but I hope I have somewhat. Thank you again for the lovely comments, Jackie.

  16. debbie 2 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

    • Author
      Jackie 2 years ago

      Identical stories practically. Thank you for sharing that Deb. It is funny yet so wonderful how all of us, well, most of share such similarities. It is truly an amazing journey. I personally believe we are a unique part of society.

  17. Misti 2 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 while nobody is around in a frantic way, while we have a few moments to spare. I can never figure out why we have this craving so early in life – its definitely a common denominator – not sure exactly when I started – but it was the 8-10 range.

    • Author
      Jackie 2 years ago

      Thank you Misty. Yes I was young when I started going out into the fresh clean air and leaving. I too at times went with a little liquid courage from my mother’s supply or my sister’s stash lol. And I know I was so fortunate that evening when I met and became friends with Jessica Rae, my first drag mentor. She helped me find the avenues I wanted to find and be a part of for sure.

  18. Pippi Long 2 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 kisses !!

    • Author
      Jackie 2 years ago

      I so do understand the overwhelming feelings. It does sound as though you have made a true connection with Pippi / yourself. Thank you for liking my story and compliments. I always appreciate it when someone actually understands what I said lol. Take care, if you ever want to hit me up to talk or chat I’ll be there.

  19. Pinkie 2 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.

    • Author
      Jackie 2 years ago

      Well I think I still have a long way’s to go but I am still learning about Jackie and it’s an awesome journey. Thank you for the compliment, Jackie.

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