Too Much Baggage to Transition

Over the years I have had so many opportunities to accept my true self and begin a life of being the woman I so much want, but I denied and shamed myself my entire life. I left my family home at 19 years old to begin my adult life. I had no one to care for but myself. I shared a two bedroom apartment with a childhood friend and it was great; he was gone most of the week days, and that allowed me time to explore my feminine feelings by shopping for make up, clothes, shoes, etc. I was so happy; I loved the way I looked. I would go out at night dressed to night clubs to meet other girls like me. I got to experience men flirting with me.

But I really did not understand that this was the time to begin my real life as a young trans woman. I had it all. The looks, a little money, the time, and I was in a city where there were many trans women. The women were not accepted as they are now, but I could have roomed with another girl and begun my life.

Then something happened. I saw a childhood friend at the night club, but he did not recognize me; he was flirting with another young man. I found out he was gay and that the stories about him had traveled throughout the neighborhood. It was sad to watch and hear, and after I heard about his troubles I immediately took all my female clothing, makeup, and shoes, and threw them away in some filthy restaurant dumpster. My first big adult denial and shame.

I went and got a hair cut and began my adult life as a young man. I dated a few woman, and actually really enjoyed my self. I always dated woman that were cute and stylish, and I would wear their clothes when they were out or when they were asleep. I was fortunate to have a male body that was shorter than most men and a slight build. One of the woman that I dated called me her little hunk. Her clothes fit me perfectly. But I ended my relationship with her when she told me she dated a man that liked to wear women’s panties and she thought it was really weird. This knowing the whole time I was wearing hers.

At some point I got an opportunity to move to California, and I got an apartment just outside of San Francisco. Here was my second opportunity. I began to build my feminine life again. I went out in my male attire exploring places I could go where I could feel safe and be with other girls like me. Initially I could only find gay bars….a lot of gay bars. Places for men who like men. They were all so tall and handsome, well dressed. Too bad I was not attracted to them. Now I had to figure out what I wanted; it was all here. I was single making good money, with no baggage in a city that accepted any life style. I found a small night spot for trans people, both men and women, and I dated a few transwomen. I just felt more comfortable with transwomen.

I dated one that I told I wanted to dress and look pretty. She thought it was fun at first and told me not to look too much like a woman as it turned her off. There I was in a city that accepted any one, any life style, but everyone seemed to want a man. Straight women wanted men. Gay men wanted men. Transwomen wanted men. I was a transwoman that wanted a woman. But if I went as a man I had no problem connecting with someone. Apparently there was a shortage of real men. They were in high demand.

I finally found a woman who was a lesbian; she was pretty and she like me dressed as a woman. She was an electrician and she was looking for a wife to take care of her. And this started me questioning myself again. It didn’t work out, even though I seemed to have it all again and yet I let it go. I went into denial; hated and was ashamed of myself.

Soon after that I moved to LA. Found a two bedroom apartment that was available for 10 months and I started again living a man’s life dating women. One woman I dated sensed something was wrong, and asked me why was I afraid to commit. I so much wanted to tell her. She was so nice, but she wanted a man. I was a woman pretending to be a man. Still, it made me sad to let her go, but I could not deny the woman in me. At that time I started to fill the spare bed room with my feminine clothing. It was easy living in LA. Cute clothing everywhere and everything you wanted was available at a small cost. Again, no real baggage, and plenty of money living in Marina Del Rey, in a two bedroom apartment, alone and single, going out to trans bars dressed. I was in heaven.

But I never again found a woman that would accept who I was. I met a lot of trans women from Mexico and the Middle East. With some I dated I had the best time; we would share stories and other things. That was the last opportunity before I started collecting real baggage. It was people – children, a wife, in-laws, family, work friends; all as a pretend man. Oh, what have I done. So many times I had an opportunity to begin my life. And I just threw it away. I took it for granted.

Now I have to be very real. My decisions about finally dealing with my gender will have a direct impact on my children and their grandparents. I have acquired a lot of baggage; and not the throw away kind. I have a very loving wife that knows, but is waiting to see what I am going to do. Three lovely grandchildren that do not have any father in their lives. They will have to be supported. They have enough confusion. And I need to earn some type of a wage. My pension and savings are enough to carry my wife and me, but not for everyone. They did not ask for their life as I did not ask for a male body. But I have had to deal with it my whole life. And in my way have learned how to deal with it. But I have acquired too much baggage to transition right now.


  1. Alex Uker 6 months ago

    Wow, these stories sound so familiar. Many times I believed that I was the only one….

  2. Angela Ramirez 8 months ago

    Stephanie this article and the responses from the other ladies is what I need at the moment. Knowing I’m not alone. Similar circumstances to all you ladies. I’m 53 and have been married for 28 years and have a daughter who recently graduated college. I should be the happiest man alive because I have a great family, house, job. I built a pretty good life. But I’ve had this big secret. I thought I was a crossdresser but with the help of my therapist I’ve come to realize I’m a transgender woman. Why couldn’t I have realized this before. I need to come out to my family. I feel I can’t keep this hidden anymore. I struggle with what makes me happy, to be my authentic self, will hurt my family. How can I do that after so many years. I also struggle thinking I’ll be alone the rest of my life. I keep thinking if I keep my secret I may not be happy but at least I wont be alone. It hurts right now. I dont know what to do.


    • Author
      Stephanie Kennedy 8 months ago

      Hi Angela You are not alone and it is very real. There is a lot at stake..Just take it slow and think it out.There is no time limit. I do not believe right now you have to come out and tell everyone like a lot of the other woman.There is just as much tragedy as there are success stories. I am beginning my transition by finally accepting my self. .That was so hard for me. I just did not understand why I had this intense feelings to accept my situation..Think about it just saying I am a woman in a male body sounds crazy but that is what I am.I Its not a good situation to be in. You can spend time as we all have buying clothes ,make up ect. trying to disguise that body but eventually we have to deal with the truth. The body does not match the brain. I have spent so many years trying to change my brain, we all have in one way or another. I think now as we get older we are just tired of fighting it
      I think we can do this without losing all that we have acquired by taking it slow. I mean over a period of years slow. Change does not come easy for most people. I starting changing when I truly accepted who I am. Keep in touch we will get through this luv Stephanie

  3. Jodi Quade 11 months ago

    I too grew up in the 60s and 70s and couldn’t bring myself to even acknowledge my femme side until I was well into a marriage and career. I love my wife deeply and as of about 7 years ago could no longer keep this growing part of me secret. For her sake i now fear that perhaps I should have kept silent. It hurt her terribly. We are still together. I am not openly femme around her. I doubt very much she’ll leave me but the estrangement that my coming out to her began has only increased. Ironically, when I first told her of my femme side, I honestly thought I was merely a cross dresser with some bisexual tendencies. She feared I was trans and would leave her to transition or at least lead a radically different lifestyle. Perhaps she knew something intuitively that I am only now growing conscious of. We remain the best of friends but have been leading increasingly separate lives since we’ll before I came out to her.

    • Author
      Stephanie Kennedy 10 months ago

      Hi Jodi Thank you for your comment. I am not sure why we all thought this was something that would pass and it would be no big deal and we could go on living somewhat of a normal life like other men..It is a big deal and we involved other people in our lives without telling them first. I feel so bad about it. I know my wife of 38 years wants me to be happy . She knows about the clothes and does not mind as long as i keep it somewhat discreet and not to feminate sorta of androgenous. I no longer can accept that .I no longer want to be a pretend man . i just do not want to pretend any longer. She does not want the man she knows and loves to go away.We both want for each other to be happy.May i will just give it more time

    • Anne Preuss 10 months ago

      Jodi, I can relate to what you say about estrangement. Although my wife knows nothing of my desires about wishing I could transition, there is a growing estrangement between her and me. It’s been a few years in the making but it has grown moreso since we stopped having sex about 8 months ago. I just have no desire for sex with her and quite frankly, I don’t desire sex with any woman. It’s as if I feel a resentment towards her, within me. I can’t bear the thought of hurting her since I am the one who lied to myself about what I felt inside all these years…so I am the one responsible for “where we are as a married couple” today. Yet, I know if we separated/divorced to go on our separate ways, I would find the decision to move forward with transitioning all the easier to make. Others suggest I just come out and tell her, but she is so vanilla/conservative that there would be no iota of acceptance on her part, to allow me to change myself into the person I wish I could be.

      • Jodi Quade 7 months ago

        I can’t read tful, just guilty an retain about how I weigh her needs/desires, my need/ desire and my guilt over the whole thing. Neither of us forsaw this 30 yrs ago. The evolution occurred and now I/we must feel my out with all the relationship and personal focus skills I can muster.

  4. Brea 11 months ago

    Hello Stephanie,
    I appreciate you sharing your life story. I recently came out to my wife about a month ago, after 12 years marriage and two kids. It has been an emotional roller coaster. Just about every week I feel like she is going to call it quits. How long has your wife known? Would you say she is fairly liberal? You say she is seeing what you will do. I’m assuming there may be some sort of ultimatum behind that, correct? what Would you say about the stability of your relationship with your wife? Did your wife go through stages of denial? Sorry for being so intrusive. I’m just extremely stressed and wish I could find the light at the end of the tunnel.

    • Author
      Stephanie Kennedy 10 months ago

      Hi Pfifer Thank you for you responce. My wife has known about my female clothing for about thirty years. When she first found them she was a little frightened .She wanted to know if I was gay. I guess most people think that about us. I. Lied and told her i was just curious about crossdressing. I was member of private club for transexuals and crossdressers i introduced her to the club when she met with other wives and she was satisfied that it was harmless . She does not know that I want more than just wearing female clothing. She is very liberal . She sorta makes fun of it.. Pfifer she does not want the man in her life to go away. She loves and wants the man she met. She comments often about how she is still attracted to my male body. I do not want to take that from her. I am going to begin HRT to help with my dysphoria about my body . Maybe she accept any changes that will happen if I do it in small doses and slowly. I am risking . I do not want to lose her but I can handle the stress of hiding any more. It is a difficult situation at best. I am not unlike most of us stuck in that thought process I want to stay but I have to go. I am not sure. Where it is going to end up just taking it one day at a time but I have to go forward I can no longer try and hide this male body with female clothing The body has to give me a little help. If that sheds any light that would make me happy. It seems every situation is a little diferent. Maybe the easiest solution is just do what other woman have done just come out and say it then do it and hope and pray for the best .With much love and empathy Stephanie

    • Jodi Quade 7 months ago

      As always the story is always too multi-faceted and complex that it cannot be entirely wife is a very liberal person in all ways. No biases against LGBT in any manner. It’s just how she conceived me…and the fear that I will chose a new partner over her. But I am also. I bisexual and year’s of celibacy are driving my lust for male companionship.

  5. Anne Preuss 11 months ago

    Hi Stephanie,
    I write this reply to let you know that you are not alone. At 62 years old, I am married, have two adult children and three very young grandchildren. I’ve wanted to be a female ever since I tried on my mother’s pantyhose and bra at age 11. How I got to where I am differs from your story, yet like you, I denied myself as to my true feelings and identity all these years. Society was much different, much less accepting when you are a child growing up in Milwaukee in the 60’s, 70’s and finding your way as an adult in the 70’s, 80’s, 90’s….hell even now it’s a struggle. So I followed the “societal/cultural rules” as a teenager/young adult. I grew up in a very difficult childhood home so survival in the form of determining a career path and earning money was a priority for me. I “obeyed” society and married at 25 yo. Sadly, I grew up in a childhood home where there was much parental chaos so I never witnessed, never understood what a true loving relationship was. Did this influence me? I think so, because I married a woman that was more of an emotional comfort for me and I did not really love her. Life continued on with career pressures and raising two children…but the feelings never went away. I might mentally push them back into the recesses of my mind but always they came back. I would find myself fantasizing what it would be like, being a woman and having a loving relationship with a man. I never was and am not interested in a male-male relationship. My desires are to be Anne and enjoy the physical and emotional joy and pleasures of a man-woman relationship. But besides that, I want to be part of the emotional/psychological world of that sisterhood that women are a part of. Men do not bond the way that women seem to. I realize that it’s not all seashells and balloons for women of course, but a man’s world emotionally lacks what a woman’s world has. If you and I had to be born as genetic males (thanks nature….you had a 50-50 chance to get it right), how different might be our lives be with the medical advances that exist today and the greater acceptance out there. Unlike you, my wife does not know and I would fear to reveal this to her…but not because I fear her rejection which I know would happen. No, my fear is that my son and his wife would deny me access to our three beautiful grandchildren. I would rather be a nana than a papa to the grandchildren and I struggle with this. We are both in a difficult situation. What we want differs from what their parents want…a traditional grandfather rather than a man who transitions into a woman, nevermind that we would love those grandchildren with all our heart whether we have testicles hanging between our legs or natural breasts brought on with HRT and a sex change with GRS. Understandably, your financial situation makes decisions all the more difficult. But now that we are in our 60’s, do we suffer in silence for the sake of the grandchildren or do we reach for that brass ring and hope for the best with the consequences of transitioning. I wish you the best as you continue on your life’s journey and may we find some form of happiness and contentment, no matter what decisions we each make in the future.


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