My family back home tells me I was always interested in feminine things at a young age, and I have very clear memories of being fascinated by wigs, nail polish, false nails, false eyelashes, etc., but my earliest actual memory of dressing was at school. I don't know exactly how old I was, but it was during sports. I loathed sports and sometimes did not have any kit to wear. The school had bins of "loaner" shorts and skirts for kids who didn't bring their own. On this occasion instead of taking shorts, I picked a skirt and joined the girls’ team. I felt exhilarated
running around in a skirt with the girls, but afterward the teacher made fun of me.The next time we had sports at school, of course I wanted to repeat the experience, but this time the teacher rebuffed me. I was forbidden from doing it again.
When I was around ten years old my first step-father died of cancer and I became withdrawn. My teacher at that time, Miss T, seemed to be looking out for me. I remember that I couldn't swim and she used to stand in the pool and pull me along by my hands. She also made me sit at the front of the class, in front of her desk. Anyway, I used to deliberately drop my pencil on the floor so that I look up her skirt while retrieving the pencil. She wore stockings and I was completely mesmerized by what I saw, and have been an avid stocking devotee ever since !
After my step father passed away, my mother took me out of school and we went and stayed with a friend of hers in Cornwall for a few weeks. During that trip I came up with an imaginary friend called “Helen”. There was a boutique at the end of the street, and I used to look in the window at the clothes. I planned to go in there and buy things for Helen (bra, panties, suspender belt), but being only ten years old I didn't have any money of course !
I remember some other things such as planning to steal my mother's contraceptive pills and take them because I knew that they contained female hormones, she also had an exercise device for enhancing the bust (which I used too).
Later, I had a steady girlfriend from about 13-15, and I did go and buy a red bra, panties, suspender belt, and two pairs black seamed stockings for her. I remember it so well, the woman who served me in the shop made a comment about the items being for me, which I steadfastly denied !
Of course, when I was alone at home I did wear them along with my mother's dresses. I gradually built up a small stash of lingerie which I kept hidden in my bedroom, until my second step-father found it. I felt so shamed I stopped dressing, and when I had split up with the girlfriend, I threw all of the stuff away. 
I left school at 15 and went to college for two years. My last school (11-15) was all boys and we had to wear uniform, so college was a revelation. I became completely androgynous, had my ears pierced, and wore makeup often. It was the 80’s and I could. During this time I had several instances of girls feminizing me, including the girl next door (who was a beautician).
After I left college, I went on a “lads” (Club 18-30) holiday to Corfu, Greece, with my friends. I met a girl and stayed in her hotel room with her and her friend for most of the holiday. The hotel held a “drag” contest and so the two girls did a complete makeover on me. My girlfriend’s friend’s clothes fit me perfectly and I entered the competition wearing them. This didn't go down well with some of my friends, and that was the last time I dressed in public. By the time I was twenty, I moved to London and started my career in I.T. at large financial corporations, and completely lost touch with my feminine side……
Thanks for reading this.
Hugs,
Helen
