Often times in the middle of a dressing session while experiencing the absolute joy of being my true self I can’t help but think of all the years I missed out on. Self acceptance was a long journey for me. There were a lot of years of guilt, shame and embarrassment before coming to the realization that this is who I am. Loving who and what you are may be a given for most people but for a lot of women like me it’s not. Learning to love who I am is the greatest thing that ever happened to me. Once I accepted myself I came to view crossdressing not as a curse but as the true gift it is. I love being a crossdresser and wouldn’t change if I could.

I can remember my younger years admiring women, not just because I found them attractive but also because what they were wearing looked so cool, and it made me want to wear the same thing. Still today I see women everywhere and wish I could look like them, or I wonder how they did their hair or makeup or where they got those shoes or that dress and so on. During game seven of the World Series this year (the only baseball game I watched all year) it occurred to me that most boys probably want to be like their favorite baseball player or football player or musician, but for me it seems like I’ve always wanted to look like (and be like) the women I admired. Everyone has role models so why can’t mine be women? My primary role model is my wife of over 30 years. I just love her sense of style and how she does her hair and makeup. She has been such a sweetheart about my dressing and has helped me so much to become who I am today. Since coming out to her and giving her the time and space she needed to process it things have gotten so much better. Our shopping trips are my favorite. Whether we are looking for clothes or makeup or whatever it is so much fun to have that in common with someone I care so much about. Also she is unbelievably good at matching colors.

On to the title of the article. “What My 59 Year Old Self Would Tell My 29 Year Old Self” could have also been “What My Single Self Would Tell My Married Self” or any other “Pre Realization Self Would Tell My Post Realization Self”. The most important piece of advice I can give any young crossdresser is to make allowances and structure your life in such a way as to accommodate your dressing. The urge is not going to go away and will probably get so strong it will over power you. I suppose you could get counselling or take medicine to suppress the urge but that probably wouldn’t make for a very happy life. Every time I see a picture of some poor crossdresser in a hotel room with panties, a bra and pantyhose on (because that’s probably all they have) it makes me want to cry. It reminds me of myself in the early stages of becoming Suzanne. I now have my own wardrobe, my own makeup drawer, lots of bras, panties, night gowns, wigs, jewelry, etc… Being able to dress completely and feel completely like a woman is an experience like no other. Nowadays I don’t dress unless I can go all the way, hair, nails, makeup, etc… Just putting on a pair of panties and a bra doesn’t do it for me any more. The days and times I get to spend as Suzanne are euphoric and so memorable. In drab mode I don’t remember from day to day what I am wearing but I can look back at photos of myself in a dress and remember what kind of bra or pantyhose etc. I had on. As a guy I don’t pay much attention to this pair of jeans or that pair, or this shirt or that but as Suzanne there are articles of clothing I absolutely love. There are dresses in my closet that bring a smile to my face just looking at them. I have some Soma bras I love. A couple of pairs of shoes make me want to put them on every time I look at them.

Unleash Your Inner Woman

The older I get I try to only learn a lesson once and then apply it to my life so I don’t have to learn the same thing again. This has me wondering if 10 years from now will I be writing “What My 69 Year Old Self Would Tell My 59 Year Old Self” or have I learned enough to enjoy my life as a crossdresser/woman to the fullest? Am I going to waste time learning the same lessons again? I want to take in as much as I can now so I don’t repeat my old mistakes and miss out on something else for the next 10 years. I don’t want to take crossdressing to the next level, I want to already be at the next level.

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Suzanne Jeffries

I am a married 60 something cross dresser from the southeast US. I thought about dressing for many years and tried a thing or two like painting my nails or trying on some panties or a bra but never really got serious about it until sometime in my 40's. Since then I have put together a wardrobe, came out to my wife and life is good.

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Marcia
Guest
Marcia

Good story.

Jackie K
Lady

Suzanna, You could not be more right about lost time and lost chances. Chances and experiences that will never be there again. I hope that the one thing anyone reading your story will be able to take away is to be true to yourself. No one can live your life for you and if you let them try your life will be full of regrets. Embrace who you are and you will fell the love you truly deserve. Not only from yourself but you will attract true friends hat will be able to accept you for the beautiful and wonderful… Read more »

Tina
Guest
Tina

Why is it that for some like Suzanne or my self it takes so long to recognize who we are? I am 62 years old and I feel the same way Suzanne feels. All of the lost time! Oh well better late than never I guess.

Carolyn Kay
Lady
Active Member

So….. true, when I think back to all the times I wasted feeling guilty and hiding I wonder how things could have been different. However, then I think of why I didn’t push myself harder, the family, friends, wife, job, and a world that just didn’t understand. I am in my mid 60’s and now have found that to be comfortable in who I am I must find a balance so all aspects of my life are included. I think I have.

Great article

Carolyn

Melanie
Guest
Melanie

Carolyn you are so very wise. There needs to be a balance and it is very different for each of us. However, once you find it things do seem to fall into place. As much as I want to dress all of the time, I am reminded of the wonderful woman that I have married. She deserves my love, respect and understanding just as much as the “other woman” woman that shares our relationship. The hard part is making sure neither is neglected at the expense of the other–something that is not always easily done. I find myself very selfish… Read more »

Helen
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Helen

These stories are so me. So true to my soul

Darlene Davinport
Guest
Darlene Davinport

Suzanne, I too am 59, and as it seems we are not alone here. There are a lot of boomers on this site. That in of itself is interesting. Your story ring so true for me too. It would be so cool to gather together to meet and discuss. I have a great place here in Anchorage Alaska which would make a great B&B, so I’m thinking of doing that for sisters get aways. Well it’s a thought. Hope you all have wonderful holidays. DD

Pippi Long
Duchess
Member

what a lovely story I loved it . it’s amazing how most of us here lived and live such cemaler lives !

https://www.crossdresserheaven.com/wp-content/uploads/2019/11/woman-gray-1.jpg
Guest
Dianne B

Loved your article. I’m approaching 70 and still love the feeling of being in female attire and think I look pretty good for old girl

cindy
Guest
cindy

you are so spot on . all so true thank you

Maria
Guest
Maria

Hi I loved the story I’m only 57 and I know I’ll never get to talk to my 27 year old self lol I wish I could but that might create a time paradox lol knowing the future I certainly would have done a few things differently but I didn’t I’m just stuck in the present doing my best to get through the loss of my late wife it’s been rough with all that led up to it and the aftermath he’s left me broke and disabled living in an Apt. but life goes on my crossdressing is at a… Read more »

Samantha Renee
Lady

God bless you hun. I know it doesnt mean or help much but im so sorry for your loss and also for your struggles lately. It seems good people always have it the hardest dear. It wont let me get to your profile, but please friend request me Maria. My Christmas isnt going to be the way I would have it this yeareven though my sutuation differs from yours. You will be in my thoughts this Christmas and Ive already sent up some prayers for you dear.

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