Early cross-dressing experiments

I first started to masturbate when I was around 12 years old, though curiously enough it wasn’t in a way one would normally think about it. I liked girls… a lot, in spite of my lack of success with them. I found the female form intoxicating and mesmerising. When we lived on the islands when I was little I used to imagine going through some sort of secret base and coming out on the other side transformed as a girl. As I grew into adolescence, I took this on a step and… am not entirely how it all started, but I used to secretly grab some of my sisters clothes… their tights, bras, panties, dresses… put socks into my bra to make it look like my tits… I don’t know, but I guess it was something about the material as well that felt extremely sexy, and definitely got me very excited. In my bedroom, I would dress the quilt up as a girl as well, imagine that we were both women having fun with each other…. I’d basically hump the quilt until I came.

I never imagined being with a guy—only other women, and I did think a lot about the idea of becoming a woman. I guess at the time though the medical technology was not quite as advanced as it is now otherwise, who knows, I might have given more thought to it.

When I was 13, I went to my second high school, and that was a boarding school, so it was pretty hard to dress up while I was there (I can imagine the reaction of the other kids if I were ever caught!). Though, whenever I went home for weekends or holiday, I would do it whenever I could. Eventually, to avoid having to sneak into my sisters’ bedrooms when they weren’t there, I took some of their clothes that I didn’t return and that I kept it all hidden behind the drawers in my wardrobe.

Once, I remember at around Christmas time, I must have been making a bit too much noise on the bed as I remember my mum shouting up to my room from the living room, telling me to stop whatever it was I was doing as they were trying to watch TV… Another time, I was really needing to do it, so I went quickly into my sisters’ room and got changed there quickly, not realising that one of my brothers was in the room below. He heard my footsteps above him and went running up the stairs shouting, “What are you doing in her room?” I was in panties and a silky dressing gown, so pretty obviously I didn’t want him to see. In my panic I shouted out for him not to come in as I was naked… not really much else I could say.

I never admitted to anything, though of course there were suspicions about the clothes going missing. Who am I kidding?! They must have known! Just nobody ever said anything to me. I remember one of my sisters making a snide comment about gay people dying from aids, probably thinking that if I was cross-dressing, I was gay… (well I would have been, I suppose, just not in the way that she thought!!). It was ironic that that particular sister was a huge fan of the Freddie Mercury, who had died just a couple of years beforehand.

By the time I was 16 though and started my third high school, I kind of… stopped. Am not sure if it was because it was “just a phase”, or if I did just suppress what I really wanted to be… The fantasies of being with women and more than one woman remain, though I guess now I am much happier with who I am than when I was back then… and I do not have regrets about the way it all turned out. I guess that the thought of any sex change operation now would never get any of my attention, though I do sometimes think “what if?”.