For all I know, I started dressing at the age of 5.
I grew up in a house where talk of sex was not entirely taboo. My parents were teachers and tried to keep my sister and I well educated. But it didn’t prevent them from being quite realistic about where children come from. I don’t think I ever believed a stork had brought me to my parents…
My dad taught science, and I remember on a Sunday morning, he showed us some sperm on the microscope. I did ask half naively how he obtained some. He answered that I knew already where it came from. I was 9 years old, and yes, I knew.
My sister was 5 years older than me. She was rather petite, and somehow the age difference meant that our sizes were very compatible. For instance, my mum would give me an old jumper that my sister didn’t want anymore. It would only be such gender-neutral items of course, but I would not be satisfied by it.
It seems that grabbing my sister’s underwear from the laundry pile was a thing I did. Often. My favourite item was tights. Somehow, it was so different from trousers. My mum caught me once in my dressing gown wearing skin tights. She was not happy with me and asked me to take them off. I had a lesson on clothes for girls and clothes for boys. But I was about 7, and it didn’t make sense to me. I said it felt so good in winter to wear tights. The way it kept my legs warm was a good thing. Also, on my hairless skin, the gentle pressure of the nylon was like a thousand fingers were caressing me.
I was much too young to understand sexuality. All I knew was that wearing tights should be allowed for boys. I took it personally that I was just denied something nice, but I couldn’t fathom exactly why. Nevermind, I kept stealing my sister’s tights from the laundry and to avoid anyone finding out, I did it at night and put them back in the morning. This meant that I wore pantyhoses overnight, in bed, as if they were pyjamas.
When I put PJs on, I would feel their cotton against my skin. Nothing exceptional there. They kept me warm in winter nights, and that is pretty much it. But when I wore pantyhoses, it was like my bottom half was encased in a silky cage. At every turn, I felt the bedsheet rubbing against the nylon, in turn making like millions of micro-brushes were stroking my skin. The sensation was bliss. I kept turning and tossing in bed, only to feel this almost cold sensation of the sheet sliding against my pores, like an army of tiny creatures with icy feet were walking on my skin, sending every nerve in my legs in complete meltdown.
I am not kidding; I believe this was my very first sensation of pleasure. So much so that when I grew a typical teenage boy, caressing my thighs over tights gave me better pleasure than stroking my penis. To this days actually, I find huge excitement in being touched as I wear tights.
As my body evolved, my hands wandered more and more over and under tights. I sill wore them a lot, always seeking these opportunities when my sister would throw away an old pair. I would sneak in, grab them from the rubbish and save them from destruction. They ended up hidden behind the wardrobe, were my small hands could grab what the adults couldn’t.
I was never found out. Lucky me! As I entered puberty and my body kept asking me to experiment with some other sexual pleasures, I kept caressing my nylon-clad thighs. I would place my dick between them, make me look like a girl and simply rub the thighs against one another. My hands would be on the side of the thighs, slowly caressing them. This rubbing up and down would excite me so that I would come. Then another trouble arose. My tights now covered in that gooey sticky stuff were not nice and soon started to smell. Washing them was fine. It’s letting them dry without being seen that was the issue. I would do it Saturday mornings as I was alone in the house. But it was still hard. So I learned to take them down and wank like the boys do, in tissue.
I wanted to push the boundaries as well, and so I started to include knickers in my game. Wearing them under the tights was good fun as my package didn’t quite match their shape. I tried bra too and soon filled them with handkerchiefs or sock. Then came the skirt, the dress, the shirts. My feet were too big for the shoes, I never got to try these. But my Saturday morning routine soon became this: Pick up clothes from my sis’s wardrobe and live as a young teenage girl for a couple of hour. Mostly it finished by a wank, then put everything in place and shower.
That is how I became a closet crossdresser. My first tights at 5, my first skirt at 12 and now I buy my own 😊
Thank for reading, next time, let me talk about the first time I could buy stuff.