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.


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Stephanie Kennedy

I am 65 years old. I am a transgender woman. I am not really happy to finally admit it to my self or others. In the past year I have been on a intense quest to help me figure out WHY I have had and now more so, such intense feelings to act, dress, and one day maybe be accepted as the person I believe I truly am. I understand now that something went wrong My brain think I am female. I know the testosterone that is being pumped into my bloodstream daily keeps my male body intact and keeps it looking male. My mind does not change It wants to see a female image I am not sure now what to do. The procces of changing this body is more than i anticipated both financial and socially. I accept I will never be considered a cis female that is my reality. I think now being a transgendered woman is acceptable to me right now. I was not born with the body my brain accepts. Should I continue to hide my true identity only to get small glimpses and brief images of a male in female clothing which I do not like at all, the clothing I like ,the male body needs some work a lot of work. Should I press forward to slowly transform that body to something more pleasant and feminate. I have spent a life time hiding. and hoping. this feeling would just go away It is so hard to look in the mirror and see the reflection of a male body. Trying to disguise it with clothing and make up does not do it anymore. My wish is for those younger people who are dealing with their gender identity get the help they will need and deal with it .It does not go away it justs gets worse. I know it is up to me. It does not seem very fair that I have to deal with the very basics of my life now. My Gender. A woman that has traveled and lived in a male body for a life time

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Lily-Rose Bodin
Lily-Rose Bodin (@lilyrose)
4 months ago

Hi StephanieIn a lot I can relate to myself. I didn’t get girlfriends, I got girl friends when I was young, I’m 63. To make a long story short. It wasn’t until recently I accepted that I am a mtf transgender lesbian. To me it still sounds wierd, but that’s who I am, and at last I can embrace it with love. I still look to much of a man. How can I convince a leasbian cis woman that I (a man) is lesbian? Sounds difficult to me. But I will now do my best to find a woman like… Read more »

Bri Sudbury
Bri Sudbury (@briannabutterfly)
6 months ago

Hello Ladies and thank you all for your comments and these very touching and similar stories. I have known I was different since I was around 5 years old when I told my mother I should have been a girl. This did not go well she had told me I didn’t know what I was talking about and shuned me and made fun of me then told other family members and they told others and eventually it carried all the way in to my teens and school. I was ridiculed and tormented and bullied until high school. It was then… Read more »

Alex Uker
Alex Uker (@alex1)
1 year ago

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

Angela Ramirez
Angela Ramirez (@angela)
1 year 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… Read more »

Leonara (@leonara)
2 months ago
Reply to  Angela Ramirez

You are not alone maybe we can help each other get through accepting or true selves

Jodi Quade
Jodi Quade (@jodi)
1 year 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… Read more »

Anne Preuss
Active Member
Anne Preuss (@annepreuss)
1 year ago
Reply to  Jodi Quade

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… Read more »

Jodi Quade
Jodi Quade (@jodi)
1 year ago
Reply to  Anne Preuss

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.

Brea (@pfiferzhang)
1 year 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… Read more »

Jodi Quade
Jodi Quade (@jodi)
1 year ago
Reply to  Pfifer Zhang

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.

Anne Preuss
Active Member
Anne Preuss (@annepreuss)
1 year 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… Read more »

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