I remember my first Cross-dressing experience from when I was quite young, maybe four years of age. I was not yet at school so I was under five years of age. I attempted to put on a pair of my mothers tights and girdle. My older sister caught me and scolded me for it, ( she would play a large part in my future dressing, or at least her clothes would ). I can't recall if she mentioned it to my parents.
I must have continued to experiment as I remember wearing my sisters blue catsuit and boots in my early school years, I think this must have been an issue with my parents as I can remember being made to go out wearing them when I was about seven years of age ( I must surely have enjoyed this ). I vaguely remember saying that I wanted to be a girl, I don't think this went down well with my parents.
In my teens I would venture into my sisters room when no one was home and get dressed in her stuff. I can remember the thrill of one time finding fishnet stocking and a garter belt in her underwear drawer.
On one occasion when I was in her room I clearly remember looking out the window while getting dressed, I had a Bra on, and to my horror my older brother was outside with some friends on their bikes. I remember him looking up at the window, I'm sure he saw me.
Another time when I was dressing I went downstairs to the kitchen, again to my horror my older brother had come home, I remember holding the door closed as he shouted “ what are you up to? “.
At other times if people where home I would go into the bathroom and lock the door, as this was where the laundry basket was kept containing my mothers and sisters dirty washing. On several occasions someone would bang on the door with the familiar question “ what are you up to? “.
I do not know what was going through my mind back then, as I seemed to be taking a lot of risks, even purchasing a pair of white tights from the local shop.
I had been tempted one time to go out fully dressed in my sisters clothes, but thought better of it, instead I put on a pair of my sisters panties and tights under my jeans and decided to take the dog for a walk. My friend had shown up earlier and I left him in with my younger brother, on returning I went upstairs to remove the panties and tights, as I was doing so my friend bounded upstairs to see me. I'm certain he saw what I was doing though never mentioned it.
I would often go to sleep wishing I would wake up a girl, though I never did surprisingly enough. There was no one I could speak to about this and very little/ if any resources like there is today. I have never told anyone about this, ever......
I had seen Transsexuals in the media and I wished I could be like them. But there was no one to turn to, and I feared the reaction of family members if I came out and said I wanted a sex-change.
I don't recall many events in my early twenties apart from the odd bathroom venture.
I moved out in my mid twenties and rented a room in a large house, to my delight one of the drawers was full of unopened stockings/hold-ups, it was like Christmas! I wasted no time in putting them to good use.
There was no Internet at this time, so openly buying female attire was too risky.....
I moved in with my then girlfriend in the second half of my twenties, she was a petite size 8, so most of her stuff was too small, though there where several items I made use of when she was out.
One day after she left for work I immediately got dressed in some of her things, to my horror I heard the key in the door! I bolted into the bathroom, she had obviously forgotten something and asked if I was OK? I said I had the shits....
On many occasions I would dress in her things when she was out, even going so far as to try on her wedding dress and all the lingerie that went with it. Sadly the marriage didn't last , though I have fond memories of her underwear and other clothes.
In the past two years I have purchased enough tights/stockings/hold-ups to last a long time. I own more ladies shoes/clothes/underwear than I own male attire, plus two dildos, an epilator, wigs, make-up etc.
I have been shaving/epilating for quite a while now, the feeling of being hairless and smooth is incredible, I don't think I can ever go back to being hairy, yeugh!
I've even considered buying one of those home laser hair removal kits, but the reviews don't seem that good.
I do say that if I win the lottery then it's hello hormones, boobs, FFS, hair removal etc. A girl can dream huh?
So I can dress whenever I want now, with hopefully no one trying to knock the door down! However I've got absolutely no intention of ever venturing outside in female attire. Ciao....
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