What My 59 Year Old Self Would Tell My 29 Year Old Self

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.

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 50 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, come out to my wife and life is good.
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28 Comments
  1. Profile photo of Wanda Shirkey
    Wanda Shirkey 3 weeks ago

    Suzanne, I too am in my late 50’s and when I look back when I was in my twenties I struggled a lot. I purged a lot of panties and bras (boy, do I wish I had them now). My wife knows about my cross dressing however she does not know about Wanda. She tolerates me right now. Occasionally, I will get a smart ass remark which upsets me.

    Love,
    Wanda

  2. Profile photo of Terrim
    Terrim 3 weeks ago

    When I was 29, I had just started going out dressed. I had gone to my first CD party and met some really nice people. I am now 68. I am married 45yrs. Over the years I struggled back and forth with accepting my femme side. I think I would say to myself at 29 is to stop fighting these feelings. They are not going away. I would say stop beating yourself up and try to find that balance in your life.

  3. Profile photo of Suzanne Jeffries Author
    Suzanne Jeffries 4 weeks ago

    Thank you to all you wonderful ladies for your sweet comments. I wish all of you the best.
    Huggs,
    Suzanne

  4. Profile photo of Sallysim
    Sallysim 4 weeks ago

    Thank you Suzanne for your article, I wholeheartedly relate to your story.
    I’m at a crossroads in my life, although I find things very tough at the moment, due to circumstances that have been forced upon me 5 weeks ago, leaving the pub and moving house. I am now settling in to my new life and relish the chance of a new start. A new start which centres around Sally. At last I can be my true self and privacy and also the public opportunities to let Sally express herself as she has wanted to for years. I’m not frightened of being who I am I relish every second of Sally
    Would I change? No I would not. I thank you for you’re inspiration.
    Sally

  5. Profile photo of Samantha Renee
    Samantha Renee 1 month ago

    Thank You so much for this inspiring piece of wisdom you have to offer us in this article. Im glad I read this. Im 29 now and can honestly say, Im more accepting of my feminine self as Samantha Renee now than ever before. I too had guilt and shame and felt less of a man (now, not such a bad thing! Lol), and lived in despair because the thing thing in my life that felt so right, also felt wrong. I still feel that shame and guilt sometimes but its almost non existent. The only times I want to purge isnt out of shame but out of the fear that my mom will find my stash(which is pretty big and im proud) and I will be exposed. I have a few times recently but not everything but I am missing my favorite pink bra very much! And a pair of cut off jean shorts and they were so damn cute too . But I dont want want to waste years trying to overcome my crossdressing and feminine urges, because they will not go away, as time has shown to be true in my case over the last 15-16 years. I am a recovering heroin and crystal meth addict and honestly, that is my priority and its hard enough as it is! Crossdressing wont kill me or cause anywhere near the damage drugs have caused and will continue to cause me if I go back (although, it definitely can affect my finances, especially the way I spend. Lol). Im not ashamed. Ive been through a lot and I know Im a strong person and I hope to help others with my same issues. And trust me ladies, I have my fair share of them!!! I try to appreciate everyday given me and I have learned to appreciate who God made me. And thats about 65-70% male and 30-35% female, bisexual and am an intelligent,loyal caring person (best way I could put it). Merry Christmas Ladies!!!!

  6. Profile photo of Lesley
    Lesley 1 month ago

    What lovely words you have shared here. You are so fortunate to have the inspiration and love of someone so close. I love the truthfulness you have in your article. It inspires me and no doubt very many within this community. Thank-you for sharing again.

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