For as long as I can remember I’ve had a strong curiosity and interest in dressing up as a girl. I’ve gathered a few vivid memories, some that are as old as I am. Probably I never paid attention on how important and frequent these events were but now I realize this.

So many memories and thoughts came to mind and they are so important to me that I will break them up in multiple chronological posts. Lets get started.


My really early childhood memories

Oh, gee! There are a few, still vivid in my mind but I cannot pinpoint my actual age for most. Definitely one of my earliest memories was soon after my grandmother passed away. I guess I was around 3 or 4 years old. One of my brothers and I had just moved to what was my grandmother’s bedroom. In one of the drawers in the closet, don’t ask me why, but there were some linens there. I specifically remember trying to fit myself into a pillow case as if it was a skirt. I don’t know. It was almost like an instinct to put on something that would make me look like a girl or the curiosity of what I would look like in a skirt.

At some point back in the 70s wigs were in fashion and my mum had a few. I remember being with her in my parents’ dressing room, probably also with a couple of my brothers, and we were just playing around with my mum’s wigs. To me it felt nice having girly hair, but I didn’t want to show too much interest so they wouldn’t figure my attraction to the idea of having a girl’s hairdo.

For this next memory I know my age because it was in the first grade. I must have been 7 years old. The school I attended had uniforms for girls, but not for boys. It also had a pre-year; a year before first grade. I do remember being in first grade and seeing this girl from the “pre-year”, so she was a year younger than me, wearing the girl’s uniform but, and this is a big but for me, she wore her uniform with pants under it. Clearly she was a girl but I kept wondering if she was a boy dressed in girl’s uniform. In my head, the whole idea of a boy wearing the girl’s uniform was exciting. I was totally attracted to her, not because she was pretty, which she was, but because she made me doubt her gender and she made me wonder what it would be like for a boy to wear the girl’s uniform.

As I think about these memories a bunch of others come to mind. Like always paying attention at the kinds of shoes that girls at school wore, or stealing a pair of socks from a friend’s sister, or with the same friend, playing in their pool with his sister’s bathing suits. It was all fun and games… but at the same time it wasn’t. It was something that I had the urge to do. It just felt good. It’s not that it felt right; it felt good. I always wondered what it would be like to put on a girly dress and have really long hair. It was like asking myself what it would feel like to fly with my own wings. Like something that you know is impossible, but still wonder what it would feel like.

Pre-teen and teen years

My mum had a plastic bag where she’d save all her old pantyhose and then she would forget about them and forget about the bag itself. So she would store old pantyhose in that bag and never come back to them. That bag was a frequent destination for me. I’d take a pair of pantyhose out and put them on. A few times I remember going to bed wearing them.

When I was around 12 I had the chance to live a year in a boarding school for boys. Nuns took care of the dorms whilst I was put in charge of the cleaning supplies room in mine. I wish I’d remember the details but somehow I got a chance to steal a pair of pantyhose, I think from one of the nuns. I hid the pantyhose in the cleaning supply room. Just imagine my urge to wear these things, that sometimes I would wait for everyone to fall asleep and in the middle of the night I would get off my bed, sneak into the cleaning supply room, put on the pantyhose and masturbate. I really never thought about it until now, but that was some dangerous stuff! The dorm had 3 rows of beds, a TV on one end, and I remember the nun’s small room on the other end, and right behind it the cleaning supply room. The chances of anyone seeing or hearing me were pretty high! I guess I really never thought about how dangerous this was until now. Good thing I never got caught!

During my teen years I remember always looking at girls, being totally attracted to them, and really analyzing what they were wearing, how they behaved, and what made them feminine, and oh so attractive. I like girls; I don’t like boys (sorry guys). I’ve always been attracted and interested, but my interest has always gone beyond being with a girl. I’ve always been interested in what they wear, their behaviour, and what made them attractive to me. I also wanted to look like one.

In those teen years I kept stealing underwear from someone when I had a chance. I also remember putting on some of my mum’s undies and trying some of her cloths, always making sure no one would ever catch me. One time walking down the street with a friend, a girl in front of us was wearing a bra with crossed straps on the back. I could see the bra through the translucent blouse she was wearing. I made a comment to my friend that I thought that those kinds of bras were so sexy. My friend just looked at me and it hit me that probably he’d never cared that there are different kinds of bras. I never made a comment like that again. Clearly I was on a very different wavelength than other guys on this.

The single time I told anyone

There was the single time in my life, at least prior to 2011  (when I started crossdressing in public), that I mentioned something to someone. I don’t think I was 14 or even 13. In my family we were 4 brothers and my parents. Our neighbours from across the street, I think they were 4 sisters and their parents. The 2 younger sisters, one was a bit older than me, and the other a bit younger than me. Maybe a couple of years each way. One day, watching TV with the youngest sister I found the courage to ask her if she could get me something to wear and a bra from her sister that had already begun developing. I cannot imagine the predicament in which I put her, and I really don’t remember how insistent I was, but one day the youngest sister gave me a plastic bag with a long burgundy skirt and a pink polo shirt. It was crazy because it was clothes for someone roughly my age and size, not my mum’s stuff, nor just underwear. I do remember my disappointment when I saw there was no bra, but gee, this was a huge step. I would put them on when there was no one at home, and then I would hide them away.

The issue hiding a long skirt and a polo shirt is that they take much more space than socks or nickers, so I made the dumb mistake of hiding them in our home’s laundry room. For some time no one saw them, until one day. We had finished supper and I remember just my parents and I still sitting at the table. Maybe my brothers had already been excused from the table or maybe they were just not there that day… And my dad asking me why there were girls’ cloths tucked away in the laundry room. This was one of the most terrifying moments of my life because I had been caught by my parents. Not fun!

With a straight face I told my parents that those clothes belonged to the neighbour and that I had asked for them for some sort of game or play we were going to do at school. I don’t know how or why but my parents believed me… or at least that’s how I understood it. They just asked if there was anything else to which I said no, and no one never ever mentioned anything again. That was the single time that a) I had told anyone I wanted to wear girls’ clothes when I asked my neighbour, and b) that I was caught, not wearing them, but caught having them… by my conservative parents!

Was there a trigger?

Now, as I re-live these events I think of my mum. I believe she now often asks herself if she or my dad did anything that triggered this in me. Of course she or anyone else didn’t do anything to trigger this in me. I had in me this interest, curiosity, urge, whatever you want to call it, for as long as I can remember; since day one. Yes, there were some events where my mum was involved but she wasn’t in the great majority of events where I expressed interest in looking like a girl. This drive was inside me before she or anyone else did anything.

It was me who kept the interest alive in my mind, pretty much every day of my life. No one else ‘to blame’, no single event that triggered it. It just was… and to this day it still is.

P.S. Writing this became a shortlist of the many memories, some of which had started to fade, and many others I didn’t include, but this exercise brought many of those fading memories back.

P.P.S. Some other not-so fading memories:

  • “Sheena” in Tone Lōc’s Funky Cold Medina
  • Boy George and every album Culture Club published
  • The Crying Game – Probably the only movie with a transgender plot I saw growing up
  • Patxi Andion’s “Si yo Fuera Mujer”
  • Jadzia Dax from Deep Space 9 – it took me a while to understand why Captain Sisko referred to the beautiful female character as male

7 thoughts on “Memories Growing Up

  1. It’s a great read, if nothing else it brought up memories for me and some are so very similar to mine, for example -the bag in the laundry room

    1. It’s incredible how trans people have soooo many similar experiences, but at the same time they are, ohhh so different! I’ve always found that fascinating. When I was growing up I didn’t know I belonged to this community.

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