The Life of an Older Trans Woman

It all started at the age of 5 when I became jealous of girls and the clothing they got to wear.  I didn’t understand why I could not wear a frilly dress and lacy Bobbie socks and black shoes.  As I got older I saw girls and how they dressed and found myself getting  more and more attracted to them, so much so that I thought I was falling in love with every girl I saw.

When I was around twelve years old, my oldest brother who was 10 years older, got married to this drop dead gorgeous woman and they moved in to the house with the family.  After a little bit of time had passed with my brother and his wife living with us, she started leaving her laundry in the bathroom.  One day I was in the bathroom and she had left her bra and panties, pantyhose, dress and her shoes on the floor.  I looked at them and realized my dream could come true.  No one was home, this feeling was coming over me and I had never felt like this ever.  I was so nervous and excited, but this wave of calm came over me as I started to pick up the panties and slid them up my legs.  They fit perfectly and then I pick up the bra; I had never worn a bra before this moment, but I got the bra on and in place.  Yet I was missing something,  so I put in some T paper to fill the cups to the perfect size breast.

I looked in the mirror and couldn’t believe what I saw back was a girl with short hair.  I had not gone through puberty yet, so I still had this thin long oval face and cute little freckles around my cheeks.  I looked down and saw the rest of the clothes on the floor.  I pick up the pantyhose and looked down at my feet and started to put them on, sliding them up my legs.  I picked up the dress, which was a mini dress (this was 1972 so you could imagine what I’m talking about) and put it on.  I looked in the mirror and was so enraptured by my reflection, I knew I had to uncover more of this new feeling.  I put the shoes on and they fit perfect with a 2 inch heel and a little ankle strap.  I knew there and then that I should have been a girl. I would continue to do this as often as I could when nobody was around until my brother and his wife Sharon had moved out to their new apartment.

En Femme Style

I had to stop for awhile, I did have a sister who was 5 years younger than me, but her clothes were to small and babyish for me, you also have to know I have 6 brothers that I had to hide this part of my life from.  This is when I learned to start to bury my feelings and become a boy, or at least try to become what people wanted me to be.  That’s when I started fixing things and building things and I ultimately became very good at it.  I enjoyed doing and enjoy having these skills; they came natural to me, so I was able to bury myself and leave the girl part of hidden, although I didn’t know exactly what to call that part of me.

I never understand why I felt the need I did until I looked back in therapy and self-exploration.  Although I dated girls, somewhere deep down I waited to be them, and at that time I knew it could never be.  I think that is when I buried those feelings and live as the gender I was born into.  I kept dating and eventually fell in love; we dated for a very short period before she asked me to move in, and 9 months later we were married, with a big wedding.  Everything seemed fine.  Don’t get me wrong; the girl inside was still there, it’s just that the feelings I have for my wife were much stronger or at least I thought they were, at the time.  I truly loved her and I wanted her to be apart of the girl I have hidden away all this time.  I finally told her I wanted to crossdress with her and bring it in to our life, but ultimately that was not going to happen.  She said it was a just fetish and you can stop thinking it will ever happen, so it was time to bury those feelings forever.

I could tell you all the stories of fights with my wife and all the times I would tell her that I would stop, and how that was one of many promises broken, but ………  The longest I ever lasted was 2 years; I was seemingly happy, but I knew deep down something was missing.   This happened more times than I could count. Most of you know what I am talking about: when you said “I will stop,” and all that money purged each time you said you would stop.  I should have understood at that time in my life I was not just a crossdresser, buy I just didn’t think at my age I could be anything other a closeted crossdresser.

So at the wonderful age of 59 it was time to understand why I was in a self destructive mood. Shutting down my feelings, addiction and suicidal thoughts were constantly present.  “What is wrong with me” I thought.  I started therapy, but I still was not totally honest with either my therapist or myself.  I was told I was not broken, that it was possible that I was transgender.  My response was “no no no.”  Well, how wrong I was.  I knew I was deep down, I just didn’t have the guts to admit it to myself or to anyone else.  I knew I could lose everything I have in my life as well as my life itself.  I did lose a lot of things, and I could list them but I will not.

I know as I live this new life of mine some of the things I have lost, or think I lost, were not actually a loss; but were giving people around me and in my life a chance to catch up with the changes, and I was finally understanding I also need to catch up to myself.  I do want you to know this is me and maybe you can relate to my life, or maybe take something from my life with the hopes you can skip a couple of the more difficult steps on your own journey.

I have at this point lived as a transgender female for the past 8 months.  There are some things I would have done differently or if I think about it, perhaps I wouldn’t change a thing for the simple fact I would not have learned from the experience.  I want you to know this is not a cakewalk by any means, but I have found that people in this time are much more understanding or at least just know to keep their negative opinions to themselves, I want to share what I am learning as I walk down this new road of life and what I am learning from all my friends at TGH.  Do find a therapist and a good doctor to work with; they can help you more than you think.  When and if you make the change in your life you will be surprised how many people will see how much happier you are and you will notice how much you will like who you becoming. So don’t use the excuse you’re too old or you have too much to lose in your life, because it could be your life for real…

With all my hopes and love I hope one day you will be your true self, and walk out that door and show everyone and yourself who you really are: a person who is just putting the pieces together to be happy with who you are.

Big hugs


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Timmie Sawyer

Hi , my name is Timmie I am 60 yr. old I came out to the world one month ago. I am a carpenter/remodeling contractor for last 26 yrs. before that a steelworker for 15 yrs. and pipe fitter for 5 yrs. boring I know.. I do like what I do, remodeling homes and handywoman stuff too. I feel like I have gone through hell to get here or to be a person I feel like for this time in my life. Well there, so there's much more to me, that's why I'm here to talk and hopefully meet people I can relate too.

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Jaiylyn Lawley
Jaiylyn Lawley(@jaiymelynne)
2 years ago

Thank you Timmie.Mirrors my own journey, which I am truly just beginning,at almost 65. But I can’t think of any way to stop it. Dr and therapist appointments coming soon.
Peace and Love,

Grace Darling
Grace Darling(@gracedarling)
2 years ago

Timmie, I just saw your article from July as I have only just joined TGF. I found it inspiring. And you look amazing.
Big love and hugs,

Deborah Rooks
Deborah Rooks
2 years ago

hi joan dearest..its not to late girl..start now start today!

Deborah Rooks
Deborah Rooks
2 years ago

loved loved your article 58 and restarted my transition almost 2 years ago after stopping for over 5 years. im happier n i feel glad to be a female n have a female shape

Gabrielle Thomas
Gabrielle Thomas(@gabrielle)
2 years ago

Loved your Story! It’s my story too!! You’re right, a lot of us know what you are experiencing…..It’s just nice to hear it from another other than ourselves. We are the same age and would both be at 9-months HRT. I stopped HRT after 3-months as the bodily changes started to take hold. My successful career, my family, any future romantic relationship came about with the Covid-19 lockdowns. I do have a great doctor and therapist but still began overthinking the future unknown. As the hormones cleared my system, I began my male life anew and all the old feelings,… Read more »

Joan Bishop
Joan Bishop(@joantobe)
2 years ago

Loved your story of lifestyle experience and change. I have many similar experinces as you growing up. I’m looking to chat with someone that has gone thru the change and now in my sixties and wonder if it is ,to late age wise, to changs.

June (Rei) Durden
June (Rei) Durden(@reidurden)
2 years ago

Thank you for sharing such an important part of your life. No matter how times I read about someone’s journey, I always find another another insight into my own experiences through someone else’s eyes.

Carly Holloway
Carly Holloway(@carlyellen)
2 years ago

What a wonderful article, Timmie. You have probably mirrored the story of many of us in the “older generation". A mental fixation you can’t shake; secrecy; love and relationships; broken promised; self-denial and rejection….and a huge leap of, what? Faith? Courage? Acceptance? Folly? Whatever! Like you, once I made the decision, the world that I denied myself opened up, with way more blessings, contentment and focus than ever before. After a year, I am absolutely certain that my choice was right for me. I, too, encourage others to take the risk. All those doubts, fears and anxieties are likely to… Read more »

Billie Ellen Grey
Billie Ellen Grey(@billieellengrey)
2 years ago

Thanks for this honest and open narrative. I have a similar experience at age 46. I’m not “out" yet, but I am recognizing that nearly 35 years of unexplained depression may very well amount to living misgendered.

2 years ago

A very similar beginning to my own. You look stunning. Thank you for sharing your story. Am sure that is just an excerpt. Always be happy and true x

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