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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30 Comments
  1. Teri 1 year ago

    Am I going to waste time learning the same lessons again?

    so true

  2. MacKenzie Alexandra 1 year ago

    Having only embraced this aspect of who I am, you words strike true to my heart. I buried MacKenzie deep in the closet for more than 20 years after a really bad emotional experience in my teen years. Looking back, I realize that I should have been honest with myself and my parents. My reaction to that experience is my biggest regret in life. I hope that our experiences can be a help to those who are young so that they may avoid our mistakes.

    MacKenzie

  3. Brittany Asher 1 year ago

    suzanne
    Thank You so much. I did the starting over thing too many times. What would I tell my 29 year old self. Stop worrying about what every one thinks or wants ’cause you cannot live their life.
    The only thing I want to have to learn the rest of my life is anything I do not already know, Like how to get my makeup right so I don’t scare myself when I look in the mirror.
    You know 40 years ago it was a lot harder Getting accepted for just being yourself. But ohhh the clothes I gave up so many times thinking I was messed up. Surprisingly a lot of them would still fit. That in itself makes me feel pretty good.
    I have a nice wardrobe again and will not be giving it up. Would love to have some of the miss Elane Gowns back.

  4. Linda 1 year ago

    I was 30 when I first went out in the world and now twice that as in the title would say ‘take pictures’ but then we did not have digital cameras and I was too paranoid to get film developed. I should also say do it more often, the voice works better than you think. However, I should not be too hard on her. She did get out. ‘He’ did buy clothes. There was no internet. You came a long way in the first 20 years and in another 30 years you will still be doing it so stop worrying, enjoy and accept the feminine side of you for it is not going anywhere. Also enjoy being 30 and your femininity as much as you can as you will never be that young again. Those things would just have been reassuring but she did well then and is content now. Thanks for provoking the thoughts Suzanne.

  5. skippy1965(Cynthia) 1 year ago

    I’m still learning the lessons I would pass on to the younger Cyn as she remained hidden from the world. Even now having gone out a few times for a significant period of time, I am still no as open about it as I would like to be. But I have made progress this last year and will continue to do so in the year to come. Thank you for telling your story -it inspires and challenges me to accept mysrlf as well.

  6. Suzanne – as someone who just turned 59 herself, and who spent the first 58 years pretty much not liking myself and not enjoying life until I finally took the blinders off 8 months ago, I feel like you have summed up my own feelings so well. In guy mode one day is pretty much the same as the next, but as April each day is memorable, especially since they are so few and far between. I also need to go all out when I dress, and I love going out because April is a bit more adventurous than my guy self.

    Wish I had learned the lessons I now know 40 years ago. Life would have been so much sweeter. But now I that I have learned I am going to enjoy every moment I can.

    Lovely article.

    Hugs,
    April

  7. Jackie Wild 1 year ago

    It’s true, life is short so why not embrace it and do what we do now. As for your wife and her being so supporting I would say you are one fortunate person. So many don’t have that support and live in constant fear of being found out and losing everything and it’s sad. When my time comes to an end I personally want to be able and say I have no regrets to take with me. That’s the way it should go I believe. Your article is true inspiration for so many.

  8. debbie 1 year ago

    We all have the female gene in here and sometimes it seems to come out later in life for many. You sound Suzanne that you are ready to take it to the next level now hon so go for it. Dont waste time regretting things cause it does no good. Just jump in girl and enjoy what you were created to be

  9. Lea 1 year ago

    Thank you Suzanne for reminding me how important it is to live everyday of life to its fullest, even the crossdressing part of life.

    As each year passes struggling with this dilemma of living my own life vs keeping my loved ones happy, I’m really concious that I’m losing precious days of happiness and enjoyment not being the true and honest about my crossdresssing. I magically hope that my dilemma will solve itself, but I know it won’t. It already feels like I’ve given up so many years already hiding this secret and can’t wait until one day I can just be out in the open.

    Doesn’t feel like I’m asking for much, then again, it is, at least until I confront those around me with the thoughts I desire.

  10. Michelle 1 year ago

    What you say is so true for many of us. Thank You for sharing.

  11. Marcia 1 year ago

    Good story.

  12. Jackie K 1 year ago

    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 person you are. They can’t very well do that if you never show them who that person is. So much you said rings so true to me. My role models have always been women, my desires have always been to be a better person by being a better woman. And yes my greatest role model is my loving wife. I can’t tell you how many times I have said to her ..your a better woman than I am… to compliment her but also to identify how I can improve myself by becoming more like her.once again thank you for voicing what I think every woman here feels down deep in her heart.
    Jackie

  13. Tina 1 year ago

    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.

  14. Carolyn Kay 1 year ago

    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 1 year ago

      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 at times–spending time doting on and dreaming about the “other woman” and forgetting the need to respect and express love to the woman that loves me for who I am regardless of which persona I am presenting. Yes, there are times I would love to take the step and totally embrace the “other woman”, but the reality of the situation is I could never go forward with it. The love, affection and respect I feel for my soul mate–the woman I have married–is just too strong. That being said, the balance in my life will always take into account the feelings and responsibilities to those that I love and share my life with and the “other woman” will always play a subordinate [though not neglected] role. Life is good and I am blessed to be able to see things from both sides.

      Melanie

  15. Helen 1 year ago

    These stories are so me. So true to my soul

  16. Darlene Davinport 1 year ago

    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

  17. Pippi Long 1 year ago

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

  18. Dianne B 1 year ago

    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

  19. cindy 1 year ago

    you are so spot on . all so true thank you

  20. Maria 1 year ago

    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 stand still for now I’m alone in a strange new world well I’ve been in an Apt. before it’s just been 30 years or so I think I don’t like it rumors got out with maintenance in and out so bad nobody talks to me so I’m kind of in solitary confinement that’s ok if I wasn’t broke I can’t even do my laundry well not much of it at least but I’m pretty clean if I can ever afford to do laundry maybe get a few new things no Christmas for me I’m sorry if I got off topic there a little I’m so in and out still too much alone time maybe I’ll just go shower and relax into something comfy and cozy my cat broke my curling iron I’m better at it than my straightener lol anyway thanks for the departure from reality I needed it I love at least being able to talk here Love Maria

    • Samantha Renee 1 year ago

      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.

  21. Lesley 1 year 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.

  22. Samantha Renee 1 year 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!!!!

  23. Sallysim 1 year 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

  24. Author
    Suzanne Jeffries 1 year ago

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

  25. Terri 1 year 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.

  26. Wanda Shirkey 1 year 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

  27. Gina Vizavi 1 year ago

    Wow! How could you write my autobiography when we don’t even “know” each other? I’ve been pondering what advice I’d have for a few weeks now prior to reading your post. One important consideration is the date in history. We’ve come light years from what it was like in our “salad days” yet we have light years to go before we approach anything resembling acceptance.

  28. Marianne 6 months ago

    Thank you Suzanne for your essay. I’m 52 years old and have been crossdressing since my early teens. I have many times thought about and regretted all the years I knew what I really wanted, but kept it secret and hidden. If I could send a message to myself 40 years ago it should simply be “Tell them who you are”, them off course being my parents. I now know that my mother probably would have known what to do, after having an intersexed uncle who transitioned when puberty made clear He was really a She. They may not have been fully understanding at first but I know they would have loved me enough to do what was necessary to make me happy with myself. Now I’m not claiming that I was very unhappy with my life as a boy and man. On the contrary, I have lived a good life there I have been and done nearly anything I wished for. But I always thought my life would have been even better if I could have lived it as a woman. And if I hadn’t transitioned I could at least have taken my crossdressing much further much earlier.

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