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.

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.

En Femme Style

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    4 years ago

    Jess – you sum everything up very well for me in just one article and I can draw great comparisons.

    The feelings of being happy with who you are yet challenging and questioning your own sexuality from within from time to time, wanting to embrace your feminine side, probably needing some sort of confidante for your own sanity, and in your case, enjoying great solace in finding one despite all the likely odds. I am very happy for you.

    Thank you for sharing.

    Sarah Daniels TG
    Sarah Daniels TG
    4 years ago


    Thank you.

    I cant think of anything more to say. Your words said everything and more. They resonated with me in many ways. Seems the more i read and meet like minded people on CDH the more i see inside myself.
    So I thank you.

    Sarah D

    Steph Di Firenze
    4 years ago

    A thought provoking and insightful article sharing an individual perspective on a common question. It resonates with many members and also provides those who may be embarking on their own journey with earnest advice.


    Stef Smith
    Active Member
    4 years ago

    I too went thru a similar time questioning gender
    I realized i m not gay but gender fluid
    I like the clothes at times and the shoes!
    But i like male mode most
    So i go between the 2 genders iften blending them vs full on transition
    Once i accepted my self as different but normal my underdressing increased and my outer dressing blended male female clothing
    More comfortable than sexual
    Great post!

    Dame Veronica Graunwolf
    Active Member

    Hi Jess….terrific article sweetie! I too play both sides of the street (male/female). Guess it is all part of being a Gemini huh. I present both sides at home and in public as the mood strikes me. I live alone and have no others so doing so causes me no grief. Guess we have the best of both worlds n’est pas?
    Take care and hope to chat with sometime.

    Dame Veronica

    4 years ago

    Jess, I must tell you that I have been struggling with the desire to dress as a woman for more than 70 years. It has never been easy, but I have never let the desire come between me as my male self and my need to be Janine. The same thoughts that you expressed have haunted me as well. Keep sharing your thoughts with others in our group.

    Kathy Jo Ireland
    4 years ago

    Thanks Jess for your story. It hit home for me. The girl in me revealed he self when I was going thru puberty and has come around like Haleys comet ever since , until the last few yrs. I’m getting in touch with her more and am enjoying her unlike I thought I would. It’s more then OK it’s just the truth of who we are . Nothing more nothing less. I love my man self I love being attractive and attracted to women . BUT I’m really liking her now. Glad I rekindled the relationship.

    Barb Encourt
    4 years ago

    I too could have plagiarized and posted your lovely article to the T.
    It’s not a hobby like my old cars and old house etc are hobbies.
    I get to transform two to three times a week although I do wear fem underwear daily beneath my business attire.
    Always the feeling of sheer exhilaration and deja vu as I strut out into the world on my high heels.
    I amaze myself how I immediately act and become fem once dressed.
    I love the relatively new term Gender Fluid.


    Carrie Lynn
    4 years ago

    Hi Jess, It is nice to hear you speak about accepting who you are and loving yourself as-is. I have said this before and will probably say it again, given the opportunity to just be who you are without gender barriers would open up a whole new world to a lot of people who do not quite fit on society’s binary gender scale. The other thing that happens, I have found, is that when you are happy and accepting of yourself those around you see that and they are happy for you. They begin to realize that many of the… Read more »

    Amanda Johns
    4 years ago

    Jess, I’ve just read your article, and with everything you said, you could have been writing about me. How you describe yourself completely resonates with me, and although I am me and don’t really like labels, if I was to use one to describe my identity, I, like you, would say I’m fluidly transgender. Also like you, I have no desire to transition or live as a woman full time, but I know that Amanda is such a significant part of me, and I can never go too long without fully dressing as her. I’ll never forget the day that… Read more »

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