Hi ladies Jackie Wild here. A long time ago, 1977 as a matter of fact, I came out as being both a crossdresser and gay. By 1980 I started doing drag. I was barely 17 when I told my sister that I wore her clothes, shoes, and boots whenever I had the chance. I’d also begun accumulating quite a few things myself.

My bedroom had the extreme look of a teenage girl instead of a 17 year old boy. My mother constantly asked me whose makeup, nail polish, clothes, and high heels I had and who they belonged to. I would always come up with excuses for it all, such as my sister didn’t have enough space in her bedroom for everything, so she was using mine to put her things in, so I left it there, or I found it and was going to give it to my sister…blah blah blah. At the time, I always thought she bought my excuses.

The lies and false excuses were getting too much to keep track of. I used to tell myself to just step up to the plate and tell her the truth. The worst that could happen was she might go off on me and tell me to straighten up or maybe she would disown me and tell me to leave. But deep down inside, I knew none of that was going to happen. I was her baby and her only boy; all of her other kids were girls (five to be exact) so yes; I was the only boy amongst five sisters.

Some of this you already know, however, it’s all pertinent to this article so please bear with me.

Visit Transgender Heaven

I’d picked up some odd jobs here and there, like cleaning houses for two different elderly women, working at a salon sweeping and stocking products for a few hours a week, at a gas station as a part time attendant, and I got a little bit of money that my mother gave me every week for doing things around the house.

School as well, to put it lightly, was a bitch for me. There were those that did like me and didn’t say anything about the way I was or about what I wore. There were those that hated me and called me names like faggot, sissy, bitch and so forth. I learned to ignore them and go about my own business. Yep, I did wear girl’s jeans, platform shoes, sometimes girl’s shirts, my nails were long and cared for, my eyebrows were thin from plucking them, and I even wore light makeup. My hair was long and feathered and obviously more of a girl’s style than that of a boy.

I was kicked out of PE because the boys complained that I made them nervous when they changed in the locker room and I didn’t give it my 100%. That was okay for me because in my view, there was just a little too much testosterone in those boys anyway. Yes the names they mocked me with did fit to a degree. There was only one other boy in school that dressed similar, but he wasn’t as extreme as me. We became friends. After school and weekends, we would dress up together and exchange makeup and clothes ideas.

We hung out quite a bit together at school and on weekends. I had three other close friends who were girls and only a couple that were boys. My best friend was a girl named Angela. She would ask me sometimes if I were gay; I always told her no, but I could feel my face blushing as I said it. In 1977 it wasn’t good to be gay or dress the way I did. Our world wasn’t ready for people like me. I didn’t allow for it to deter me from being who I was. The first time I confirmed, or had strong feelings, that I was gay was when I met a guy in a gay bar parking lot. I knew it was a gay bar. I tried with all my heart to get up the courage to walk through the door, but I would always chicken out at the last moment. I was close to 18, but the law said you had to be 19 to go into any bar. I figured they would ask me for my ID and I didn’t want to be embarrassed to be turned down.

En Femme Style

Just when I was pulling out of the parking lot, a guy came to my window and asked me if I was going in. I lied and told him I had already been in there and was now going home. He asked if I could give him a ride home and I said sure. Cutting the long story short, that same guy became my first boyfriend. I introduced him to my mother and two of my sisters as a friend of a friend of mine. I also introduced him to a couple friends, Angela and another close friend Ricci, who knew from the first second they met him that he was gay. It was then that I knew for certain that I was in fact, gay.

He encouraged me to keep dressing the way I did and helped me to realize that I was destined to be who I became. He taught me to recognize and feel what it’s like to be in love and to be loved unconditionally. With him by my side, I entered, and went through the door of that bar. Of course, I was in full drag attire, wearing lots of makeup. I suppose that, and the fact that he was a regular customer assured and bought my way through the door with ease. Once in, I immediately felt at home. As we sat down at a table, his roommate, who happened to be a drag queen, came over and introduced herself. I stood up and gave her a light handshake. In return, she gave me a hug and said it was great to finally meet me.

That night, I met several other people, and each one was so friendly that I couldn’t help but to feel grateful and excited. I was finally meeting other like-minded people; it was over whelming, but I easily made a decision that night. I knew I’d found where I was accepted and liked by many. It was also the place where I met my first drag mother, who showed the way for me and taught me many things.

If I have offended anyone, I apologize. I have helped many to be where they wanted to be, because I believe that’s what we’re supposed to do–help others be who they really are. I also firmly believe that we don’t wake up one fine morning and say, gee I think I’ll throw on a dress, heels, and makeup to become a crossdresser, drag queen, bi, or gay. Lady Gaga says it best in her top of the charts song, Cuz Baby, “We were born this way.”

I know for myself that it just came natural and I followed my heart. Things happen for a reason, and we all have destiny and fate waiting for us. It’s up to us to follow our hearts and trust in what we decide for our lives. Everyone has a place to be whether it’s a construction worker, a CEO for large corporation, a crossdresser, or a drag queen. We’re all here to be what we were born to be or choose to believe in. For those who have read this long article patiently, I thank you from the bottom of my heart. I do get a little long-winded at times. One of the many things my first drag mother told me was, “Anyone can put on a dress, but it’s how you wear that dress that counts.” Jessica Rae, you’ll always be a part of my heart, RIP.


More Articles by Jackie

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


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)

0 0 votes
Article Rating
Inline Feedbacks
View all comments
Active Member
5 years ago

Thank you so much for your input.. I really needed that today. You inspire me.

Active Member
5 years ago
Reply to  Jackie

hugs back, Mikki

Sandra Stevens
5 years ago

Jackie thank you so much for sharing your story. You brought me to tears as I truly feel it is so close to my life in many ways. I just wish that I were a strong as you were in your younger years. I come from a family of all boys and 1 girl my cousin. I wish I had a sister or was the sister but as you said in the 70’s it wasn’t easy to be myself. I applaud you and I surly draw so much inspiration from you. You are an amazing woman and and I’m so… Read more »

T.J. Byron
5 years ago

LOVED your story…glad you are living a happy, fulfilling life.
At 73 (October) I live every day to the fullest, never knowing if the next day is your last. T.J.

Jean Jeanie
4 years ago

What a fantastic story, thank you for your courage and encouragement:)

Deborah Sullivan
Trusted Member
3 years ago

Just to say how inspired I am too hearing your story Jackie. Our lives were indeed very similiar

Would love your thoughts, please comment.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?