What does being transgender mean to me? It means my gender crosses the usual boundaries of strictly male or female. It does not mean I am confused. I know for sure that I am not 100% male or 100% female inside and that my comfort zone shifts from time to time. I enjoy dressing in female clothes and making myself look feminine. I enjoy the feminine mannerisms that I get to employ when I dress and that, for me in my life, are off limits otherwise; they feel natural to me. I very much feel as though I am expressing a part of myself that is and always has been inside me. This is not just a hobby that is fun for a fleeting moment in time. And I most certainly do not feel guilty about it!

I experience feminine emotions and desires each day. I suppress them in order to function in the culture in which I live. I do not feel comfortable displaying these mannerisms or emotions in “guy mode”; or dressed as men typically do in our society. However, it isn’t just about the clothes. There is a feminine component to my personality and who I am at my deepest core. This is a huge contrast to who I am on the outside most of the time. Most of the time I am as stereotypically male as the next husband, father, endurance athlete, hunter, shooting sports enthusiast, car mechanic, or infantry combat veteran. I am all of these things all of the time. My gender, though, is not so static, therefore, I consider myself to be transgender; gender fluid to be more specific (and to attach a label if you need one or if the situation dictates it).

I do not have any desire to physically transition to womanhood or to live or dress as a woman full-time. I do love my opportunities to be Jess when they present themselves and sometimes I feel a bit boxed in when I cannot dress for a long(er) period of time. So there is some degree of need to this versus it being nothing more than a want, like a hobby might be. And this is all still somewhat new to me, relative to those who knew they were trans from a young age, whether they had a label for it or not.

There was no struggle for me when I was growing up as I never focused on nor was I confused by these feminine feelings. I just shrugged them off as if to say, “Boys don’t do that sort of thing” and off I went down my blindered path. It makes me feel a bit like a fool now, but it wasn’t a problem at any time until recently.

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So how did this all come about? Last summer I became more concerned that my underdressing was just an indication that I was actually gay. I started to research what it could mean and happened upon some articles about crossdressing. I immediately felt drawn and dug a little deeper. In an extreme coincidence, I received a Linkedin connection suggestion at this time. It was from someone I had worked with, in the same office, but did not quite recognize.

Literally, at the same time as I was beginning all this questioning of myself and who I was this person was reintroduced into my life. I messaged her to ask how and when we worked together. Turns out I did not recognize her because when we worked together she was he. I immediately recognized her and the connection was made. She shared her story with me, and I began to open up about mine. We talked about it all, then we talked some more. She suggested I get a makeover to see how it felt, and she recommended a well-known makeup artist in the area who is a great friend to the transgender community and who could do a complete transformation: makeup, clothes, and photography. I considered it, and I decided to do it, booking the appointment for Thursday, September 5th, 2017.

At the risk of sounding a bit sappy, sentimental, or just downright silly, I consider that to be Jess’s birthday. That is the day she saw the light of day and the weight of all the undetected repression was finally lifted. I saw a woman in the mirror, and I felt liberated to walk and move like a woman can and does. I slipped so naturally into Jess it felt freeing and euphoric. I am excited as I learn how good Jess can feel every time I get to slip into her being. Make no mistake though, at times I get tired of being Jess. That is the gender shift, or pendulum swing if you will. That is why I know I do not need to transition.

Being Jess is great and even perfect for some specific times. She just isn’t all of me all the time with no possibility of or room for anyone else. She is the feminine portion of me, which I express fully when I can. Jess does not control my entirety. I am not only her. I am not only him. I am me. And I am fluidly transgender.


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    Jess Jones

    I have only recently discovered that my true destiny is to crossdress, vice simply wearing lingerie for thrills. It has been a wonderful and exciting journey so far, though not without the obvious nervous anticipation and tensions. Making great friends who have either walked the path before me or simply been rocks of support.

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    5 years ago

    I love it, this article that you wrote Jess is really fantastic and I can tell you this is what I been looking for what I am, I am indetify whit Jess. I thought I was bisexual but I am not, this article change for complete my way to think. I am transgender because I am exacly how you describe on this article. I hope my wife can understand what I am and I am going to compart this to my wife. Actually I been seen the title many times but I nver been curious to read it, I am… Read more »

    Peggy Ann Culpepper
    5 years ago

    Thank you Jess for sharing your story with us. I sit here as i peck away, never learned to type. that was for sissies, back in the 50’s when i was growing up. Ha, Ha. It is so amazing that so many of us have the same identical stories to tell yet we are from the entire spectrum of the social and ethnic backgrounds. I am just a poor farm girl (transgendered) that started CDing at the age of 2 or 3. By the age of 5 , i would cry because i could not have the pretty dresses and… Read more »

    5 years ago

    Jess, I just have to say I deeply identify with this article. Thank you, Lilly thanks you. This helps me clarify how I feel about myself by a lot. You offer some really good insights on what exactly being comfortable in your own skin is, and at the same time what being gender fluid might be. I was just perusing articles around the site for some insight but I swear I’m actually shaking a little bit here after reading this, it’s kind of hit me at my core here I was not prepared for that. If I can offer one… Read more »

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