First Person: Transwoman finds inner peace after four decades

LGBT Perspectives columnist Dianne Skoll kicks off our First Person series with an article about finding herself and coming out as a transwoman. The series will feature first person narratives about personal LGBT-related issues and experiences. An index of articles in this series will be kept at the top of our home page.

By Dianne Skoll
LGBT Perspectives

Dianne Skoll.
Dianne Skoll.

This piece is a departure what what I usually write, as it’s very personal. So please be kind!

First awareness

This is a question I get asked a lot: “When did you know you’re transgender?” Many transgender people answer “Since childhood”, but for me the answer is not so simple. The awareness that I’m transgender actually took a long time — more than four decades, in fact.

In retrospect, of course, there were clues. And I suspect some transgender people who say they’ve “always known” are projecting back what they know now onto their younger selves. I say this so that other transgender people who haven’t “always known” don’t feel like frauds; awareness can come at any time.

My first transgender memory came when I was about 6. When I couldn’t sleep at night, I used to imagine that I was a girl. For some reason, I always imagined myself as a girl in a bathing suit diving into a pool. Possibly, it’s because I wasn’t a girl and I wasn’t a very good swimmer.

I grew up in apartheid-era South Africa and although my parents, family and some of our friends were very liberal and progressive, society in general was not. I knew instinctively that my girl daydreams were not something I should mention.

Progression through adolescence

When I was about 9, a couple of cousins stayed with us for a few weeks — one boy and one girl. I convinced my cousin that we should try on his sister’s clothes. Since she was younger than us, it was a struggle to fit into her clothes, but I managed it. My cousin didn’t seem to care much for it, but I found it oddly exciting. I experienced feelings I’d never had before and couldn’t articulate. Looking back, it was probably a combination of adrenaline rush and erotic excitement (yes, even in a 9-year-old).

By the time I was 14, we’d moved to Canada and I was regularly wearing women’s underwear, usually old things my sisters had forgotten about. At this point, I saw it strictly as a sexual fetish.  I would dress up and masturbate; after the release I would feel disgusted and angry with myself and promise never to do it again. The promise lasted a couple of days, typically.

When I was 19, I finally plucked up enough courage to buy my own women’s clothes.  I concentrated on underwear and lingerie, but did pick out a few pieces of outerwear.  My shopping trips were furtive and ear-reddening expeditions with my heart pounding each time I bought something.  Of course, there was no way I’d try something on before buying, so I ended up with badly-fitting clothes that didn’t suit me at all.

Also, around that time, I grew a full beard that I sported for much of my adult life.  I figured this would make it impossible to cross-dress without looking ridiculous and would act as a curb on my enthusiasm.


When I was 19, I met the woman I eventually married. At 19, I was still a virgin and desperate to remedy that. I thought that “normal” sex would cure me of my desire to cross-dress. I also thought that married couples had lots of sex, so there wouldn’t be time in between for the desire to cross-dress to build up. Of course, I was wrong on both counts.

I told my wife that I cross-dressed before we were married. She was very much taken aback, but eventually decided she could live with it. She believed (as I also did at the time) that it was just a sexual kink. We were married in 1991.


Around the time we were married, I became intensely curious to meet other cross-dressers.  (The word “transgender” had not yet entered my consciousness.)  Since the Internet as we know it was just taking off
in 1991, there was no way to look online for groups. I have no idea how I found it, but I somehow stumbled on a support group called Gender Mosaic. I met with the president, who vetted me — they had serious concerns about transphobic people pretending to join in order
to harass or out the members, or worse.

I shaved my beard and for the first time in my life, went outside dressed as a woman.

Also by this time, my feelings about cross-dressing had changed. No longer was it an erotically-charged activity. Instead, I just felt calm and at peace when dressed as a woman. I had (and still have) no idea why.


In 1994, our first of three daughters was born. She was an incredibly demanding baby, so my free time completely disappeared. I went to a few more Gender Mosaic events until about 1995, and then quietly dropped out of the community. I grew my beard back and spent the next 18 years being a parent to my children. I never went out dressed as a woman until
2013, and I almost never dressed up completely even at home.  If I had desires to cross-dress, I suppressed them and limited them to under-dressing.


From about 2006, my marriage had been going downhill. My transgender desires were part of the problem, but we had many other problems. Gradually, I began withdrawing into myself and closing myself off.  I numbed myself because it was too painful to allow myself to feel anything.

I started to experience intense bouts of gender dysphoria, which was a new and horrible experience.  When I saw women, I had an intense longing to be like them.  The clothes became secondary.

In May 2013, my father died. He never knew I was transgender. He had always told us that we should be true to ourselves, regardless of what other people think. He said it was more important to be authentic than to worry about appearances.

My father’s death triggered roiling thoughts and emotions. I began to realize I had to do something about my gender dysphoria or I would become sick. In September 2013, I shaved off my beard and reconnected with Gender Mosaic. Once again, I ventured out as a woman.

Finding myself

The composition of Gender Mosaic in 2013 was very different from 1995. Whereas in my earlier days, almost all GM members were cross-dressing men, most of them married, in 2013 there was a substantial complement of transsexuals — people who were transitioning or had transitioned.

As I made friends in the group, I found myself gravitating to the transsexuals. Cross-dressers tend to talk about clothing, makeup, shopping, how to keep the activity secret and how to hide your “stash.” I found this incredibly uninteresting compared to the people
who were transitioning, who spoke about finding themselves, what gender really means, and how to live an authentic life.

In December 2013, I went to Gender Mosaic’s Christmas party. I was not yet out to my kids, so I had to change at the venue. It was still a furtive and shameful secret.

At the party, I danced as a woman for the first time in my life. And cheesy as this sounds, my epiphany came while dancing to Girls Just Wanna Have Fun by Cyndi Lauper.

A switch in my brain clicked.  This is who I am.  This is who I want to be. This is right.

Beginning transition

By this time, my wife and I were going to couples counseling because our marriage was clearly in trouble. I had disclosed my cross-dressing, but in January 2014 during one of our sessions, I blurted out “It’s more than just cross-dressing. I want to be a woman.”

This was met with shock by both the counselor and my wife.  Neither knew what to say.

Over the next few months, I started to take steps toward transition. I started seeing a gender counselor on my own. I started laser hair removal and had my ears pierced. Every step forward that I took made me happier and distressed my wife. The emotional stress from being pulled two ways was incredible.

In February 2014, I came out to my mother. She was shocked at first, but was loving and supportive and continues to be so to this day. In April, I came out to my sisters who were immediately supportive. And finally I came out to my children. I feel unbelievably lucky that my children, my sisters and my mother are completely accepting and loving. This has been such a help to me that I think it has literally saved my life.

In June, I started taking a testosterone-suppressing drug. My wife was furious. She also insisted that I come out to her parents, which I was resisting because I knew their attitude would be hostile.

Against my better judgment, I did come out to her parents. Their reaction was as I expected: They essentially called me a crazy freak, an irrational monster, and an idiot to throw away my family life for something impossible. They were convinced I had been confused by immoral and licentious friends and that all I needed to do was “smarten up”.

Final doubts

Although I’m a strong person, I had a much deeper reaction to my in-laws than I expected. I was filled with doubts and confusion and I stopped taking the anti-androgen.   told my therapist I was not transgender, just a cross-dresser, and would manage my gender dysphoria that way.

That June and July were among the darkest months of my life. I felt confused, alone, sick, and filled with fear and doubt.

The right path

Finally, by September I had sorted out my feelings and resumed taking the anti-androgen. I also resumed seeing the gender therapist. In early October, I ended our marriage and moved out of the family home.

From October to December, I gradually started living more and more of my life as a woman. I learned basic skills like how to pick clothes that suited me, how to apply makeup without looking like a clown or a drag queen, how to sit, stand and walk like a woman and how to function in society as a woman. I would force myself to do errands such as grocery shopping or picking up library books as a woman. I knew that I had to combat my fears of not “passing” and of being harassed head-on.

On De. 31, 2014, I came out to my business partner and to two sets of family friends. All were shocked. All were supportive. Again, I feel incredibly, unreasonably lucky.

In January 2015, I finally had nagged my gender therapist enough that she set up an appointment with an endocrinologist.

On March 11, 2015, I started on cross-hormone therapy.

On April 18. 2015, I started living and working full-time as a woman.

Choose life

My life now is very different from before. My gender dysphoria has totally evaporated. I feel at ease in my skin and at peace with myself now. I have made wonderful new friends, and I’ve reconnected with old friends. It’s as if I’d been living in a gray-scale world that suddenly turned colour as I experience life anew.

There have been losses along the way. I have probably lost a good childhood friend. My marriage is over. My children have to change residences between my house and my ex’s every week, which is tedious and unpleasant. I have experienced sexism and condescension; I now really understand what “male privilege” means.

But overall, I feel better off. I feel happier. I feel like a complete person.

Sometimes, I’m asked “What would you do differently?”  Would it have been better to have acknowledge my transgenderism early on and transitioned early? In many ways, sure. I would have had many more years living as my authentic self. The physical process of transition is easier and the results generally more successful the younger you are when you start.

But I’ve never been one to harbor regrets. I look at my three intelligent, funny, talented, strong, passionate, beautiful daughters and realize I would never swap them for anything in the world.

I had to wait 47 years to discover who I am. But the wait was worth it because living an authentic life is incomparably sweet.


5 thoughts on “First Person: Transwoman finds inner peace after four decades”

  1. Always be who you is,
    Never be who you isn’t.
    ‘Cuz if you is who you isn’t,
    You isn’t who you is.*

    Self can never be denied! God bless and keep you.

    *This from a friend in Cape Breton, they talk funny there too!


  2. I am simply astounded by your story. I can only image what you must have endured during your amazing transition. I personaly believe being true to yourself is the most important decision one can make during the short time we have. You have obvisouly made that brave and grand decision. Congrats!


  3. I was deeply moved by your story, Dianne. I remember you as a clever little boy in South Africa, when your mother and I were teaching colleagues. She and I remained firm friends and I followed the outline of your life through letters and then emails. I applaud you for your courage to make authentic choices. I hope you continue to get love and support from the people who really count in your life, and at least respect from those who don’t.
    Sincere wishes. Jenny Christie


  4. Thank you for sharing such a personal story. Ironically, I think it’s universal in its drive to be true to oneself, the opposition one inevitably faces, the self doubt, and finally the sweet result that makes all the pain worthwhile. Andre Gide said, “It is better to be hated for what you are, than loved for what your are not.”


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