Women's leather shoes made from genuine python leather. Female high heel shoes lie on a wooden table

This week our cross dresser success story takes us all the way north to Quebec Canada, where we join Joanna on her journey through hardship to celebrate the woman inside. As regular readers know by now, cross dresser success stories are real life stories from wonderful transgendered woman all over the world. These ladies have conquered self-doubt, bad hair days and all manner of malady’s to achieve success in some aspect of their crossdressing.

Please share your own cross dresser success story. It can be funny, scary, dramatic, emotional or described by some other adjective completely. A small slice of your cross dressing journey will shine a light for those who still travel this road in darkness.

Meet Joanna

My name is Joanna and I live in Montreal Quebec Canada. I have been a crossdresser since a very young age. Now divorced and looking to start the next phase of my life. I am 45 years old.

Joanna’s Cross Dresser Success Story – Celebrating the Woman Inside You

My story begins at age 5 or so when I was playing dress up with my 2 younger sisters. I remember donning a pair of mom’s pumps and putting a rag on my head to serve as long hair.

My mom sent me a strong message that day to never to repeat this (although she does not remember doing so) and things went underground from there. I continued to dress in my room and when there was no one home. I would go into mom’s closet and wear her dresses, heels and makeup.

As puberty hit I started to feel the guilt around my dressing and began the dreaded purge cycle for quite a number of years. You see I was raised in a very religious household and this was an aberration. I remember one time as a teenager crying in the shower praying that the urge would go away. Of course it never did.
I married shortly after my father’s death from cancer (in retrospect a mistake) and tried hard to suppress my desires for as long as a year at a time. I would buy clothes and after having masturbated in them after an outing as Joanna promptly threw them out always promising myself to never do it again.

Then after 12 years of marriage I told my wife about my secret in a letter to her which she actually found before I could give it to her. At first there seemed to be nothing but understanding and compassion around this issue and it was great. I entered a gender therapy program at the hospital to try and figure out where I was going with all this. My wife even went out with me a few times with me dressed as a woman. Then some months later she turned on the whole thing and said she wanted a divorce.

Our marriage had never been the strongest from the start and now this was the camel that broke the camel’s back for her. I was not happy either and after having had a health crisis in late 2007 (as it turned out a small stroke) things started to really go downhill for the marriage. In fact during my 10 day stay at the hospital she came for a one hour visit.
I am now divorced and things seem to be going better. I am feeling more relaxed, my children are adjusting well and my ex and I are able to communicate better. We are co-parenting our children and focusing on them. The therapy helped me to accept myself as I am and to realize that I am this way for a reason. God loves me exactly as I am and there need for guilt or shame regarding this activity. My mother and siblings now know about Joanna and have tried to be very understanding – so while they may not relate to what I am doing they take my word that it is something very deep and trust that I need to express it. God love them for it.
I now celebrate the woman in me by regularly going out and doing the little things as Joanna. I grocery shop or go downtown for a coffee. I get tremendous peace from this and treasure this part of myself. I am currently living with my mother until I get a new place and she faithfully washes my boy and girl clothes. I know I really have a good thing there.
Although I am now alone and would welcome an understanding woman in my life, I will never again suppress this part of myself to please another. I have learnt that we all need to be ourselves and in so doing be a better person towards other people even if society rejects us for who we are.
Peace,
Joanna

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10 Comments
  1. Lynn Jones 11 years ago

    Thank you Joanna for sharing your story. I found it very honest and it can be a rough and rocky road that we walk.

    I hope things pick up for you and you find someone to share your life with.

  2. carlos 11 years ago

    es muy bobito y espero que te vaya bien en esta vida y que puedas disfrutala aqui en españa estas cosa van mejorado y ya hay matrimonios reconocido por el gobierno un beso

  3. Jeri 10 years ago

    Hi Joanna,

    Thank you for your story. I’m a cross dresser too. Have been most of my life. I think you make such a pretty girl! Very classy clothes. You look very cute. I love to dress femme and shop, one of my favorite things to do. Message me some time. I would love to chat with another girl like me.

    Kiss,
    Jeri

  4. Liz 10 years ago

    Hi Joanna,

    My boyfriend is a crossdresser. I myself am bi so there has never been a problem, even though he sometimes wonders about it. I love him dearly and would never do anything that would make things more difficult for him. I’m glad that you share your story so openly and will make him read it as well. I take him shopping, we share clothes, he wears nightgowns to bed and I’m always very supportive. I do what I can for him. I was just wondering if there is anything else I can do to help support him. Thank you again for sharing your story. You are very brave (and very attractive, if I do say so myself).

    Liz

    • Meiliza Darling 9 years ago

      hi Liz, that was great, your support. He must be very lucky to have a girlfriend like you.
      I am also a crossdresser, i love to dress up too.
      But, i prefer to go out dressing, and doing it alone or with my crossdresser friend.
      It is because i shy (and shame) to my woman if i dressed in front of her. She is like you, she can accept me just like you.
      Cud you ask your boyfriend and tell me whether he felt the same too? even a little?

      LING
      Find me on my Facebook : Meiliza Darling

  5. cordelia 9 years ago

    Ok – so done the tears and the shock bit and have got to acceptance. There has to be something in acceptance for the spouse. My deal is when I cross dress – which she doesnt enjoy – I do all the housework, which at leat makes it bearable. I had a lovely nightdress this valentines, but when I wear it (quite often) she gets breakfast in bed

  6. Elaine 8 years ago

    wow, excellent story, good for you for winning it

  7. Elaine 8 years ago

    Like you said Joanna, once there you’ll always want to be there, i know, I’m there AGAIN now

  8. Miss Aud 6 years ago

    Is cross-dressing legal in Ontario ?
    Does it apply to all of Ontario or only some parts of it ? ( if applies only to some areas could you give a listing of which areas permit and which areas don’t permit )
    Will the police detain you or give you hard time,penalize you, because of it ?
    If one was cross-dressed could one walk in public with no problem ?
    Example: Wearing a skirt and top that is chosen by the person lets say close fitting shirt.
    Does skirt length matter ?

  9. Tim 5 years ago

    Are you still around? I will be visiting Montreal next week and would love to go out

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