Realising I was trans in my teens

My story

This page is the start of my story from when I first started to feel that I was a girl and not a boy.  I have started at age eleven, which I think was my first awareness, even though I had never even heard the term "trans", and then various experiences that came from these feelings and then eventually finding out what all of this meant a few years later.  

These are my experiences, unique to me, but I'm sharing as they may be relatable.  

First attractions

Although I didn’t realise it at the time, my first attraction to a girl was also my first attraction to being a girl. 

It is strange that I still remember after all this time, but maybe that’s the nature of significant moments in our lives. 

It was 1986 and I was eleven. It was the summer between primary school and senior school and we were on our family holiday on the Isle of Wight. 

I had sort of fancied girls who I thought were nice or pretty or whatever, but only in a childish innocent way. I guess playing at the idea of something without any real concept of what it really means. Up until this point, I had never properly fancied anyone in that way. I didn’t even know how!

This holiday was just like our previous holidays. We had been to this place before, stayed at the same accommodation and played on the same beach. 

The beach was brilliant there. A little stream trickled down from the cliffs and ran over the sand to the sea. All of the kids would take their buckets and spades and spend hours building sand dams to stop the water, which required constant maintenance as they pools behind them filled up and overflowed, breaching the sand and triggering a flurry of excited digging, piling in more sand to stem the breach. Hours of fun and I loved it.  This year, the plan was the same: spend all day at the beach, playing in the water and building dams. Or playing frisbee, rowing inflatables in the sea, proper British seaside fun.  All the kids on the beach would play together, with the older ones looking out for younger siblings. Parents largely left kids to their own devices in those days and sat behind windbreaks reading or doing puzzle books.  We only returned to them for food and the daily ice cream run. 

The group of kids playing together that week were a mixed bunch from all over and both boys and girls. There always had been both and it had never been something I had thought about in previous years. 

This year was different. There were boys. And there were girls. And there was one particular girl who I took notice of. I don’t remember her name but I do remember how she looked. And I remember how that made me feel. 

The girl was pretty, and she had shoulder length blonde hair, which she wore in a pony tail. Her skin was tanned, which we all were in the old days before people realised that the sun was harmful and smothered their kids in suncream from head to toe. We all ran around in swim wear fully exposed to the UV, no hats or t-shirts. For me, that was swimming trunks, no doubt very unattractive and unfashionable ones. For the girl, and in fact pretty much all girls back then, the one piece swimming costume. I don’t know when bikinis became the norm, but in the mid eighties, the one piece was the thing. 

Some girls had colourful swimming costumes, or patterns or floral designs. Sometimes they had like little skirts at the waist for decoration. 

This girl’s costume was just plain black, like the ones they had for school swimming lessons. Nothing pretty about it, low leg, high neck and back, square shoulders, no decoration, just functional and designed to cover up. The one thing that made her stand out though was that she wore a little pale green crop top over the top of her costume. I suppose I now realise she must have been beginning puberty and it was to cover her up and preserve her modesty. But at the time, I didn’t understand any of that. I didn’t even really understand what a crop top was, I thought it was just a very short sleeveless t-shirt. But somehow I found it appealing. I think it was the contrast of the pale colour over the plain black costume. Maybe I was aware of her more feminine shape. Whatever it was, the girl in the crop top was the first time I properly physically fancied someone and felt that kind of attraction.  My first lust I suppose. 

I certainly was attracted to this girl (I do wish I could remember her name), but that was not the only feeling I was discovering. I was curious to know how it felt wearing her swimsuit and the little crop top over. I don’t really know what swimsuits are made of, but it’s stretchy and clingy and the fabric is sort of shiny. I wondered how it felt to have this clingy material all over my body, clinging to my tummy, to Have it over my chest, and held in place over my shoulders. What does it feel like over my bottom, where it stretches and moves when she walks, how would that feel to me?  And how different does it feel when it is wet or dry? What is it like to swim wearing a swimsuit and feel the water through it and inside it? And what about the crop top? Another clingy layer over my chest, how would that feel. Does she feel nice wearing it or is it in some way uncomfortable for her, whether physically or emotionally? Did she wear to cover up because she was embarrassed by how her body was changing or at least self-conscious about it? Was she scared of the changes and becoming a woman? Or was she excited to be growing up, proud of her new shape and sporting a crop top to show the world that she was growing up?  What would it be like for me? What does it feel like to be her, to be a girl, to inhabit her female body and wear her girl’s swimsuit and crop top?

When I lay awake fantasising about her at night, I was thinking of both the girl and of being the girl. But maybe more the being her than about her. 

At the time, I didn’t think that strange. I don’t know any other way of thinking about girls so to me, this is normal. I fancy them and want to be them. I didn’t know either that most males just want the girl, they don’t want to become the girl. And neither did I have any inkling that this is indicative of gender dysphoria. Why would I, to me, it was just my normal feeling towards girls. 

Nothing happened with the girl, we just played together on the beach, had a nice holiday and never saw her again. Well, except in my head, where I can still picture her. 

Early attractions

I have written previously about my first attraction to a girl when I was eleven and how I was as fascinated by how it would feel to be her and wear her swimsuit as I was attracted to the girl herself. 

At the time, I had no idea that this was not “normal” and that it was a sign of who I am inside. I had no external reference as to how you should fancy girls, except for other teenage boys’ conversation which was mainly as sophisticated as saying “phwoar” a lot. This does not provide the unknowingly gender questioning boy/girl with many clues. 

School did provide most of my early attractions and fantasies though. 

One of the new subjects we had to do now I was at senior school was “performing arts”, which was on rotation with art and music. It was sort of a combination of drama and dance and took place in what was officially called the “theatre” even though it had no stage or seating. It was more of a dance studio space I suppose but strangely had no windows or natural light. The one thing it definitely did have though was a very strange and unpleasant smell. And it was this smell that gave the room its name among the kids, of the "cheesey feet room". Because it involved dance and movement, it necessitated changing clothes. For boys, we just wore our PE shorts and t-shirts and went barefoot. But the girls, they were free to express themselves. Being the nineteen eighties, this meant leotards and leggings, usually matching sets and generally in that shiny lycra like the "green goddess" on TV (I realise younger readers won't get that reference!). I expect the "normal" way of looking at my female classmates would be to ogle their shapes and curves in the skintight lycra. Was that how I saw them? Not exactly. I saw the outline of a bra through the leotard and imagined how it felt wearing a bra. Like I had over the summer with the girl in the swimsuit, I longed to know how the tight fabric felt on my body, this time not just the torso, but all over from feet to neck to wrists. Oh my, how must that feel? And those sort of dance didnt just end at the ankle like a regular pair, they go over the foot like a stirrup, covering the sole but leaving the toes, balls of the feet and heels bare. I assume this is for grip on the floor, functional not sexy, but to me, how does it feel to have the stirrup stretch around under your foot? Girls are so lucky! And the ultimate fascination of these outfits was the layering of the two parts. Leggings covering from the sole of the foot to the waist, then a leotard over the top, not just covering them, but somehow securing them (in my mind). Dressed thus, you wouldn't be able to take off the leggings to get to you underwear beneath, at the foot they are fixed by the stirrups and at the top, secured by the leotard. Even now, the idea of this makes my heart beat faster, as a young boy, it was the most thrilling dream of all. No doubt to the cisgender girls, they were just functional outfits that were fashionable and they chose the colour they liked and then maybe felt a bit self-concsious when all the boys in the class just stared at their breasts. Which I guess I did too, but maybe wit different thoughts in mind. So, what have we learned from this little trip down memory lane, if anything? At the time, I didn't know any different, but it looks like from the very beginning of puberty and sexual awareness, I was fascinated by the other path down which I was unable to travel, I was wanting to cross-dress to experience how girls felt, amd I was having female embodiment fantasies. That probably means I was "weird" and I was sufficiently aware of that to keep my feelings secret, even though to me, it was my normal. In case you are wondering, once I had left home and was free to dress as I liked in private in my own place, one of the first things I went out and bought was a leotard and leggings set.  

First dress

The first time I wore a dress was a special feeling. 

At the time, I didn’t know that I was in any sense transgender or gender questioning. I was thirteen and didn’t even know such things existed. I was aware that when I looked at the girls in my class, part of my fantasy was to wonder what it felt like to wear their clothes, and especially their underwear and tights and skirts. 

My first opportunity to find out was slightly unexpected and from the source of my German teacher who wanted her class to stage a pantomime for Christmas. In German obviously. 

I was cast as one of the ugly sisters (oh how apt!) or to give me my German name, a hassliche schwester (apologies for the spelling, it’s been a while and there should probably be an umlaut in there somewhere.)

Our teacher kindly provided the costumes, and I was issued with a dress. It was a long strapless gown of gold satin, which my mum surmised has come from the teacher’s kids dressing up box as it had some elastic sewn in at the top to use as a halter neck and hold it up, and had a few splashes of poster paint on it. My mum washed it and sewed a couple of balled up sock into the chest so my ugly sister would have big fake boobs. 

I remember trying it on for the first time and how it felt, having a lot of fabric around my legs and then the bodice all over my body. The dress zipped up at the back. It was quite tight on me and when the zip was done up and I felt my body pulled in and the fabric tight all over, it was the best sensation! I loved it! 

Suffice to say, I tried the dress on a few times in secret before the play and I was very disappointed to have to hand it back in after the show. 

Although I have many of my own female clothes now, these are mostly casual and I don’t have a ball dress to wear. I am like Cinderella! Poor me. 

So at thirteen, I was dreaming of wearing my classmates bras and skirts; wearing a dress was the most wonderful feeling; I constantly fantasised about having breasts and getting periods. And I had no idea at all that I might be transgender! Really. The very idea just didn’t exist in my world. 

Female Embodiment Fantasies

The term “female embodiment fantasies” is something I have learned fairly recently, thanks to the Internet and the access it gives me to papers on gender dysphoria and transgender issues. 

What I am going to write about here is my inner world as a teenager. A time when I had never heard of gender dysphoria, female embodiment fantasies or even trans gender. I was aware of “gay”, and that everyone at school viewed that as a Bad Thing, but that was all I knew. I didn’t know anyone who identified differently, had never even heard of anyone changing their gender. This was the nineteen eighties and I knew nothing. 

I knew nothing about gender identity but I did know how I felt. 

Please forgive the indelecacy, but as a teenage boy (for so I was), I spent a fair bit of my time fantasising and pleasuring myself. That is normal I guess, but was the subject matter of my fantasies “normal”? 

I am sure I stared at my female classmates just as much as the rest of the boys did. But did I see the same thing? 

I saw girls wearing skirts and the line of their underwear. I expect that the normal boy thing is to see their legs and the shape of their bottoms. I fantasised about the knickers and how it would feel to wear a pencil skirt and to walk with my thighs restrained by it. The school skirt was navy blue, knee length and fitted, pencil skirt style, with a triangle bit at the back with some extra fabric in so it allowed more freedom of movement. If I knew the first thing about fashion I might know the proper name for that, but I’m afraid I don’t so you will have to rely on my poor description. Why do I mention it at all? Because when the girls walked, it pulled tight and then slack again, and the tight the other way, then slack...how did that feel? My trousers didn’t dictate my stride length. I didn’t feel them with every step, like the girls must have. 

Naturally, I observed their breasts too, and that would be normal. Except I was not just interested in them, I wondered how they felt. Through the thin white cotton blouses that were the girls’ uniform, I could see the shape of their bras. From the front, the white triangles of the cups and the thin strap going over the shoulder. From behind, the straight horizontal band, tight around their slender body, with the thin shoulder straps at right angles. The idea of the bra was always overwhelmingly fascinating to me. It was nothing like anything I wore and was part of the special identity of being a girl. In my mind I felt it was like a “contraption” that was fastened around the girl’s body in some sense, but on the other hand, something that gave security and protection. I was fascinated, but clearly also confused! And I was a long way from just thinking about boobs. 

The odd way in which I looked at girls extended into my fantasy world. Although I wouldn’t have been able to describe them as such at the time, not knowing such things, my dreamworld was filled with female embodiment fantasies. 

The obvious things, like wearing a bra and knickers, tights and skirts of course. But also fantasising about having a female body and particularly to have breasts. 

I had no way of realising that sort of dream, or even knew it could be possible to do so, but my imagination dealt with that. 

I imagined meeting a genie who could grant me three wishes. Without hesitation, wish number one would be to be born a girl. It still is. And then I would imagine what my life would be like, about my body and clothing and what my periods would feel like and how much they hurt. 

Alternatively, I would imagine I was forced to become female by some controlling state. Maybe I was captured and wrongly imprisoned and experimented on? Or quite often, I would imagine being locked into an iron leotard that concealed my true gender and gave me a feminine body shape and I couldn’t ever remove it. I think maybe I had recently seen the film of the Man in the Iron Mask and had put my own twist on it. Freud would probably say I felt a need to be seen as female and lock away my male body but needed it to be done forcibly against my will because I was too afraid to admit to who I am. Or something like that. 

Which might be true as my fantasies around that time did tend towards being made to be female by someone else, never by coming out and saying that was what I wanted. 

So that’s a bit of inappropriate sharing from my teenage mind. I’ll end here  

First contact

First contact with a real girl that is. 

Apologies that this post will contain some reference to mild sexual experiences but I will try to be delicate. 

As I have mentioned in other posts, in my teenage years I was as attracted to girls as the next boy, but I was also very much attracted to the idea of being them, although at the time I had no idea this was not “normal” and maybe signified something about me. 

Unfortunately I had little to no success in getting a girlfriend. Ok, let’s be honest: no success. At all. Maybe I wasn’t masculine enough! Hmm. 

I was fourteen before I first kissed a girl. We met at the ice rink, skated together and chatted and then before she had to go home, we “snogged”. I had zero experience so had to follow her lead and she was rather vigorous in her kissing. Forceful even, and pushed her tongue well into my mouth. Frankly, I feared she might eat me. Nice to get a score on the board, but I cannot say that I enjoyed the experience. You have to start somewhere I suppose. 

My second encounter could not have been more different. And I mean good different. We met on a summer camp weekend, sailing and sports and stuff. She was from a different school although still in the same county. Her name was Katy and she was beautiful, tall, slender and with long blonde hair. So far out of my league we might have been playing different sports. Somehow, we got chatting during the day, got along well and on the Saturday evening, left the dancing in the marquee to go for a walk by the lake. Walking became walking hand-in-hand, which after a while became sitting by the lake and watching the sun go down. This became kissing. Kissing Katy was nothing like kissing Claire had been. Where Claire had been firm and forceful, Katy was so soft and so gentle, kissing her was the nicest thing ever. After a time, it got dark and turned colder so we went into one of the tents and lay down, still kissing in this soft lovely way. She asked me to stroke the back of her neck under her hair, gently with my fingernails because she liked that. She did the same for me, it was tingly and felt nice. All the time, kissing one another. At some point I touched her breast, still kissing, still playing with her hair and tickling her neck. Her breast was the most deliciously soft wonderful feeling. Through her t-shirt I could feel the shape of her, her softness, the small proud nipple and the fabric of her bra. She allowed my hand inside her t-shirt, directly touching her bra, which was soft and satiny, no wire or padding. Touching her softness through the satin and stroking the nipple felt divine. It was beyond anything I had ever imagined. Now a "normal" teenage boy would, when he got home, spend a lot of time "thinking about" the kissing and the breast fondling. As we have already established, although I did do that, I was not normal and there was more to it for me. I longed to know what it felt like to her. I put on one of my mum's bras and tried to cup and stroke my own chest, and to find and stimulate my own nipple to feel what that is like through the satiny bra material to try to feel like Katy. But I knew I wasn't feeling it quite the same. My chest was flat and hard, none of her beautiful softness; my nipple tiny and flat, not rounded and raised. It felt nice, and sexy, but in my heart I knew I wasn't feeling it for real. Nevertheless, this remains one of the most influential moments of my trans life. That feeling, of my breasts being touched is still something I long for. It is why bras more than any other garment define for me what it is to feel feminine. It is why the ritual of putting on a bra is key for me when I dress to be Nicola. Fastening the band, covering myself with the cups and then securing it in place with the shoulder straps is so important to me. That first contact with beautiful Katy shaped my vision of femininity, but more than that, it shaped how I see myself as female.