Transgender - My Personal Journey

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This is a work in progress.

What a beautiful girl!

I know it means nothing, but I always find it amusing that when I was a baby my mother had to put a bib on me that read "I AM A BOY" because most folks who saw me for the first time would exclaim "What a beautiful girl!".

My childhood was a somewhat confusing time. I was an only child and very shy, which made making friends difficult. Another difficulty, though I didn't really understand it at the time, was that I didn't get on with the boys, but because I was a boy I got thrust into that group.

We moved not long after, to a country town. It was here I learned a few lessons. The first lesson was that effeminate boys got hurt. I was always picked on at school. Eventually my Father decided that boxing was the way to go. I didn't really enjoy it that much. One beneficial effect was that the next time I was picked on, I hit back. As far as I can remember it occurred to me then that the way to survive was to be this macho boy.

My next step wsa to become the school bully.

I formed a group of other boys around me and we became the leading gang at school. I occasionally made forays to try to talk to girls about things that interested me. None of these were successful and I learned another lesson about being a boy.

Despite this, I often did the 'dress up' thing at home, and always wore my Mothers or Grandmother's clothes. I was ashamed of it though, so hid it even from my parents.

High School Hell

Several things happened to me just before, and leading into my High School years. Firstly, my Father put the fear of failure into me. Secondly my hormones started flowing, confusing me even more. Thirdly, just into High School, my Father left.

I'm not sure which of these factors contributed to my first Depression and Nervous Breakdown in Year 7. I vaguely recovered and functioned but I didn't know how to deal with what was inside me. I was attracted to girls, but I was also attracted to boys. I felt confused and a huge amount of guilt. I was also jealous of the girls. I was jealous of what they talked about, their accessorising, of their groups. I didn't understand any of this. I made a few naive, blundering attempts to enter girls groups, but I was seen as a bit strange and laughed at.


By the time I got to college my male persona was well in place. I was no less uncertain of myself, but I was 'male' and that was it. I did guy things (or tried to) and pretty much passed it off. I was seen as strange for my lack of interest in football or mechanics, but I 'redeemed' myself by being 'good at computers'.

Any 'non male' thoughts or feelings were ruthlessly pushed down hard by me, and denied. This of course caused me more issues as I had more and more I had to deal with. My crossdressing continued but it became more and more covert. I also began to steal from the sisters of friends, just so I had some female clothing of my own.


I had more of a vocabulary now, and was less naive. I passed my crossdressing off to myself as a fetish, and remained ashamed of it. In fact I was pretty much ashamed of myself full time. I seemed to be two people: the person everyone knew, and the 'real me' who was a terrible, twisted person. I had got very good at lying to myself and others and I lied without even having to think about it. Luckily none of my lies came back to haunt me; but I am convinced that was purely luck.

The Real World

I got a job and with money came a little more freedom. But not much happiness. I had no girlfriend, only girlfriends. I was very confused as I seemed to have no luck with women romantically. I think most of that was my lack of confidence, and the fact that I wouldn't let people close to me. I still felt incredible guilt and shame at being attracted to men.


I did get a girlfriend at last, though she was 18 and I was 25. It barely lasted. Eventually I found another girlfriend and she became a fiancee, then a wife.

In hindsight it was a doomed marriage. She didn't know who I was because I couldn't tell her. I couldn't even tell myself. She didn't know I cross-dressed, didn't know I was kinky. She didn't know the real me. Come to think of it, I didn't know the real me.

Our marriage was put under strain when I found out about Dominance and submission. For the first time ever I tried to be totally honest with myself and with her. But that kind of relationship, that kind of lifestyle wasn't for her and it almost came down to a choice between D/s and her.

Will The Real Me Please Stand Up

With this new honesty, I was forced to look at all those things I'd hidden, and with it came the realisation that I wasn't the person I portrayed. I wasn't even male inside.

I ruthlessly pushed that down again. I knew that that bit of information would break up my marriage. And from that brief flash of honesty I went straight back into hiding. This time, however, I knew what I was hiding. It now seemed that no matter what I did, I couldn't push my feelings down hard enough, they kept surfacing.

One day I admitted to an online friend that I was a Transgender. It was the first time I had admitted it outside my own head. I tried exploring this side of me 'safely' online. The more I explored, the harder it was to hide it in 'Real Life'. Over and over again I resolved to push it down, to forget about it, and mosty the very next day it surfaced again.

For two years I tried to hold all this inside, hold myself together and hold my marrage together. One day I realised that I had two choices: Tell my partner, or end up in a mental hospital. I'd already suffered a number of Nervous Breakdowns in my life, and I don't think I was that far from being committed.

I agonised over how to do this, knowing that she wouldn't be able to deal with her husband being female. In the end I chose the worst way possible and hurt her, and myself, more badly than I could have.

There is a happy ending to that part. She and I are now as close as sisters. I've been lucky.

Where I am now

Currently I'm living two lives. Yes, the lies are still there. My ex, my family and my close friends all know I'm female. When I go out in public I dress female (even with a bit of a 5-O'Clock shadow). However at work I'm male. Though even there I'm 'getting away with' nice earrings, painted nails and long hair. I hope to come out at work sometime, though I'm not sure when.

1In ACT, Australia, High School is often Years 7-10, while College is Years 11-12. No, I don't know why

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