Crossdressing Success - From hell to heaven

Crossdressing Success Stories are real stories from crossdressers who have succeeded in an aspect of femininity. Their success may be personal or public, but the lifelong impact is unquestionable. Each step on the way to success builds confidence until finally we can comfortably live as who we are.

Share Your Crossdressing Success Story

If you would like to share your crossdressing success story, please email me at and let me know you’d like me to share with others. Please include:

  • Your femme name
  • A brief introduction (1-2 sentences about where you live, how old you are and such)
  • Your story (if you go over 700 words I’m going to edit you down :) )
  • Optional – A photo of you (no nudity please)

I’ll post your story on Crossdresser Heaven within a few weeks.

Even though your success might seem small to you, I promise you that it will encourage and uplift a sister who has yet to achieve such success.

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Meet Linda

My femme name is Linda.  I am 60 years old and started crossdressing about 10 years ago.

Linda’s Crossdressing Success Story

Before then, I had never been motivated to do such a thing being too busy earning an income and bringing up a family.  Looking back, I do love women and in general preferred their company to men.  When my wife was shopping for new clothes, I always went with her encouraging her and criticising when needed.  In my lunch hour, I often bought clothes for her and was never interested in buying men’s clothes for myself; in fact, the only time I bought my own clothes was when something needed replacing.  I loved my wife to wear miniskirts and high heels, which she didn’t like much at all.  It was only later in life that I realised that I was the one who should be wearing them.

About ten years ago, I started experimenting in secret.  In three years, I had accumulated a small wardrobe of miniskirts and tops and some badly fitting high heels shoes.  It had to be small as I had to keep it hidden in a locked brief case in my study.  I wanted to go further but the secrecy prevented me.  I realised that I must tell my wife and come out of the closet as it were.  I really did not know what to expect, but one morning when we were lying in bed having just woken up, I confessed.  Naturally, my wife was shocked and her initial reaction was that I could continue to do it in private but she did not want to be present at the time.  I asked her if I could email her some photos so that she could see what I looked like.  I guess she must have been curious as she said yes.  We kept talking about it and eventually she consented to see me dressed.  When she saw me, she said I looked OK, although she was a bit jealous of my legs and figure.  Shortly after she told me that she would accept my crossdressing because in her words: “Once I saw that it was still my M________ under the clothes, I realised I had nothing to worry about.”

From then on things just got better and better.  Not only did my wife accept my crossdressing, she became an active participant and supporter.  She helps me buy clothes, jewelry, make-up, shoes, hose, wigs and in fact anything I need to be a girl.  My life went from hell to heaven in no time at all.  Christmas and birthdays took on a new meaning with a whole new range of gifts that could be bought.  We have such fun together; crossdressing has added a whole new dimension to both our lives.  Shopping together is always fun as we are always on the lookout for new “frocks”.  We both know that crossdressing is fun, creative, sexy and harms no one.  And we love it.

The emphasis on the last sentence was mine, just so you don’t miss what a positive experience crossdressing is for Linda and her wife! Read a few more crossdressing success stories, or decide to take the next step towards your crossdressing success. Read a crossdressing book, share a resource on crossdressing with your wife or transform your feminine appearance.


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I’m passionate about creating a safe space for everyone in the transgender community to find laughter and friendship on their journey. I completed my physical transition in 2011 and through it I lost everything, and gained everything. I am blessed that I was forced to gaze inward and embark on the journey to discover and live my authentic self. My deepest wish is that all who wander here may find peace, happiness and freedom.

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15 years ago

And outstanding story,,you are so lucky to have such a strong marriage and friendship with your wife,,heck you look really good to be 60 yrs young…keep on having fun…hugs god bless arla

15 years ago

beautiful story.,

15 years ago

I’m so jealous of you. Gosh.. look at those legs! Wish I can go out like you..

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14 years ago

Hi Linda, I feel so identified with your story, yet I have not begun to be daring and have no one I can share my story.
At 55 I started to crave again what I had done a couple of times around 14 and it sure has me in the want.
Congratulations on your story, it helps a lot.

7 years ago

Linda, I just love you story. I was uplifted by it and am extremely happy for you. Although I am elderly, I have always had the desire to be a woman. My first recollection of it was when I was only 8 years old when I painted my finger nails with red crayon. Throughout my life I have crossdressed from time to time, but have not wanted to come out of the closet, so to speak. But your story sure gave me encouragement. Thank You, dear. Call me Norma

Vera Jane Gonsalves
Vera Jane Gonsalves
6 years ago

Thank you Linda. That was a nice , positive ending article. I wish I can say the same about my life. Have a great time ahead….
Vera Jane

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