November 29, 2020

Building a Better Boy…

“Looks like a rooster in the hen house.” The sales associate remarked, “Can I help you find anything?”

I was shopping in a women’s clothing store. The sales-person was trying to be kind and funny. This was for sure one of her go-to quips when a “man” walked into the store.

I just smiled. “No, I’m just looking thanks.”

I was presenting male at the time so her comment was no surprise but for a moment it reminded me how absurd this was…me…a woman.

…and yet here I was. No confusion whatsoever about who I am.


Shortly after I had (mostly) accepted that I was transgender, I had reached out online for some girlfriends of the non-romantic variety.

I lived in a small city and it wasn’t somewhere I could walk around town presenting female without my life totally unravelling.

My new friend and I met for drinks at a local restaurant. She was really sweet. She owned her own business, was really sharp, confident, lots of tattoos, a little witchy…we got along great.

I was describing myself and my new found inescapable nightmare – gender dysphoria.

“So don’t comment on this but it’s like this beautiful thing inside me, burns so brightly, that I can’t understand how anyone walking down the street can’t see it too.”…meaning my true gender.

So she commented on it. “Yeah” as she looked at me accross the table, “I don’t see it.”

Well no shit you don’t see it…that’s what I was getting at. Serves me right for low-key waxing poetic πŸ™„.

…and this is the burden of a transgender person, especially when you are way beyond the age of being able to intervene in your appearance at the developmental stage.

You are stuck with you as-is…without surgery anyway.

I’ll never look like a woman, I thought to myself, I’m right f*cked.


I was five years old when I recall my brain starting to function in an odd orbit.

I wish that part of my story was knowing I felt like a girl at that young age. It was not.

My experience was more tangential. I knew I liked girls more than boys. I was also attracted to them in more ways than one.

I remember wanting to make friends with girls when I was young.

Even at fours year old. I lived in Australia and desperately wanted to make friends with the two sisters next door. I was a boy and therefore unwelcome.

One sister poked me in the eye just to make sure their messaging was clear.

It was. I wasn’t going to be accepted in their circle. πŸ™

I remember living in this housing complex in Calgary when I was in kindergarten. I must have been having behavioural issues. I recall my teacher needing to speak with my mom quite a bit. Once even visiting my house with me at a lunch break one day. We ate grilled cheese sandwiches that my mom made and tomato soup (which I always hated). This memory is odd, it would obviously never happen today.

So at 5 or 6 I:

  1. Became sexually aware,
  2. Became aware of my first fetish, and
  3. Had my first desire to be female…in a way…

I won’t get into number 1 or 2.

Number 3.

I remember seeing women dressed in lingerie in the big Sears catalogues that used to get delivered throughout the year. This aroused me (See items #1 and #2 above) but also had me experiencing odd thoughts for which there was no context in my life.

I wish I looked like her. I wish I could feel like she does.

What is a young “boy” to make of such things?


There was a young girl who lived in my housing complex. One day a house accross the street was burning down, you could feel the heat from fire from where I stood. I saw the girl watching as we all watched the drama unfold.

She didn’t seem to be interested in being friends with me despite my efforts. I was learning that boys and girls, like cartoon dogs and cats, don’t mix.

There was a group of boys that I tried to infiltrate. They didn’t seem to like me either. There was something about the way they were and the way I was that seemed to make friendship impossible.

I somehow perceived I was less-than something (perhaps in more ways than one).

I needed to be more like these boys if I was going to have friends.

One day I saw the girl follow her older brother, who was carrying golf clubs, out to the field adjacent to our housing complex.

I had never seen golf-anything before and the girl was there so I made my way over to where her brother was hitting golf balls down the field.

“Get out of here. You can’t watch!” The young girl insisted vocally.

“You can’t make me. This isn’t your field.”

Apparently she thought differently as she grabbed a golf club (an iron of some kind if I recallπŸ€”) and proceeded to split my scalp open with it. I was a bloody mess. No idea how many stitches were required.

Boys belong with boys. Girls belong with girls. I really knew this now…

The die was, at that moment, cast…if I was going to fit in and have friends, I needed to be a better boy.


I was in elementary school now. Maybe grade six or seven. I would have been 11 or 12.

I still didn’t fit in as well as I’d hoped. Being a better boy was harder than I thought it would be.

There was something I was just missing.

So not only did I have trouble making friends (I was never anyone’s first choice to hang out with). I also had entered the time at school when boys and girls started to become interested in one another.

Here was the beginning of school dances, birthday parties with girls invited, and the odd couple trying their first shot at their version of “dating”.

I envied the real boys. They seemed to get noticed in ways I just didn’t.

Not only was this affirming that I wasn’t making the headway into real-boyhood to the degree I had hoped. It had also laid bare another problem entirely…

Where not being a particularly convincing boy made it hard to make male friends and fit in, it appeared likely that I was not going to be found attractive by girls either.

This was a bigger problem. I perceived that I needed to be accepted by boys to get liked by girls.

This was my first perception of the alpha-male dynamic without knowing it by name.

This is what I had to be…


My early and mid-teens seemed much like my younger years. More feeling awkward and out of place.

Crawling out of my own skin and never knowing why.

I had developed a few fetishes that were most certainly in the female orbit. These had begun in kindergarten and carry on (almost) to present day.

I was excited to be “feminine” sexually. Most notable example was always fantasizing about myself as a woman with other women.

In the lesbian porn I preferred, I was always one of the participants, never a man watching off-camera or third-man in.

I loved heavy metal. I remember buying my first Motley Crue album, Shout at the Devil. Inside the album cover were pics of the band members. They looked wonderfully feminine. They also appeared to have zero issues getting girls…

I was going to grow my hair and get my ears pierced.

I had always wanted to wear hoop earrings. So I did. Back then wearing an earring in your right ear allegedly meant you were gay.

I didn’t care. I got both ears pierced.

Growing my hair out took a while but it happened.

…and so did something miraculous.

Girls started to notice me…but something was still missing…


It was grade 12. I finally lost my virginity. I was still not-quite-alpha but close. I had regular girlfriends now and I had bluffed myself out of some pretty-sure-I-would-have-had-my-ass-handed-to-me altercations (in one case I faced down 2 known tough guys…I should have been killed).

It felt great but I was still crawling out of my skin. I had no idea why other than it had always been that way. I felt different in what really only amounted to a secret life where I got to be a a girl in my head…and it all revolved around sex.

At this point I had also had a handful of platonic relationships with women. Not only did I enjoy their company more than men’s I was also attracted to women romantically.

Only a few times did these worlds nearly collide.


As I moved into full blown adulthood I realized that I still felt like a fraud. I had met “real men”. I knew I was a fake. I imagined they felt it too.

So my struggle continued. As my career began and I was promoted over and over again in a male dominated industry. My ability to fake alpha flourished.

I intimidated many men and women began to find me attractive.

This was where I found myself December 2018 at 48 years old.

I dive with sharks, I ride motorcycles on-road and off. I have a gun collection. I have a massive toolbox and can fix mostly anything. Upper management positions in my field. I have a wonderful and hot girlfriend of two years – I have made it.

A lifetime of trying and I finally have this whole thing by the balls…

…I am finally a better boy.


My mother died that Christmas. I came to visit her.

She had hidden the severity of her cancer. She was stage four and incoherent when I arrived Christmas day.

I lived in a different part of the country. I would have come to see her earlier if I had any idea. She didn’t want me to worry.

That hit hard. My Mom was difficult to grow up with. She has been depressed her entire life. We were close though. I was most like her.

On her death-bed, as I held her hand and stroked her arm (the one without the IV), she became lucid. I could see it in her eyes, they pleaded with me desperately.

She mouthed the words, “I’m sorry.” and they carried the weight of her soul with them. An apology for being ignored and mistreated as a child.

“It’s okay Mom.”

Then I fell apart at her bedside. The last interaction we would ever have.

I missed my Mom and I felt that grief.

A month later and I would know a new grief…and emotional pain beyond words.


Sometime around January 2019 I began to experience changes that had no precedent in my life. My existence had become absurd, surreal.

My experiences lead me to a place around October 2019 that compelled me to accept that I was transgender.

The pain of seeing just wrong in the mirror is something I can’t describe. I have no idea how many hours I have cried.

Eventually I had to tell my girlfriend.

I struggled for months. So many dropped hints and aborted plans to tell my girlfriend who I was and what I had been experiencing the last year.

I fully expected to lose her when I finally came out…but she stayed.

This was a wonderfully unexpected turn of events.

I have texts from her professing her love for her girlfriend Allison. πŸ˜”πŸ’”

The more I became my true-self, the more fearful and distant she became, not because she didn’t love me, but because she wasn’t attracted to me as a woman.

This is what she is attracted to:

This is what she lost:

This is what she has now…

Imagine her disappointment. It couldn’t be any more pointed…and unfortunate and unfair.

I had been in the habit of growing my beard out a bit so she’d be attracted to me.

The other night she just said it “looked weird”…the last of my fake man abilities taken away from me.

Hormones have softened my features, my mannerisms have changed, I dress differently and I spend as much time presenting female as I can.

I’m forever sorry for what she lost. After all, she hasn’t changed for me. I still adore her like when we’d first met.

It is only I who have changed.


No rooster in the hen-house whatsoever. I carried on with my clothes shopping like I belonged there – I do belong there.

My (technically ex) girlfriend was shopping with me. She perceived some confusion from the staff as only I went into the change room to try on clothes.

My girlfriend thought they may have been concerned about a man in women’s change rooms…because the store is for women.

I wasn’t the least bit affected but my girlfriend felt a bit awkward.

I don’t worry at all about this type of thing and I could see it makes her anxious.

We both went up to the checkout. My girlfriend bought some tights.

I was next in line. I bought tights, jeans, a necklace and a blouse.

“Here’s your gift receipt.” The cashier was the same lady who had called me the rooster in the hen-house.

“Oh it’s all for me.” I remarked honestly.

The cashier laughed, “Sure.”

I laughed too.

Once again reminded how absurd the idea of me as a woman is.

As it turns out, I am profoundly and painfully aware of how absurd this is. How hard it is for people on all-levels to accept.

I live this utterly surreal life. I can try to resist but it’s futile. Whatever will be will be and I’m not sure who’ll be in my life at that point.

I must find peace in no longer struggling against the inevitable.

A wonderful quote from the TV series – Sense 8. Nomi is trans.

I’m not sure I’ll ever quite understand why being authentic matters so much…but it does.

I have tried to resist for the comfort of others…and it got me nowhere.

It’s time to end this unforgivable violence I have perpetrated against myself since I first realized I didn’t fit in.

I am no longer lost.

I am no longer building the perfect boy.

Are we destined to burn or will we last the night…

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