Must've been 5-6...I know I was in kindergarten...I started with panties, pantyhose and gymnastics leotards.
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Must've been 5-6...I know I was in kindergarten...I started with panties, pantyhose and gymnastics leotards.
Aged 10-11. I'd get home from middle school an hour before any one else in the family. "Borrowed" my sister's clothes. I was saddened when she tossed them all at Goodwill a few years after that.
II'd do the same, come home from school being alone for a couple hours meant making a beeline to the panty drawer.
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My first lingerie item in my collection was a black babydoll that mom had hidden away, probably destined for the Goodwill but luckily I rescued it. Perfect condition. I was probably 10 or 11.
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House sitting was a thrill for me too. Neighbors would go on vacation for two weeks every summer (1960s) and I'd be asked to clean the swimming pool. Of course they also gave me a house key. I'd finish the pool and it was off to the bedrooms (daughter and mom). Great fun playing in the lingerie.
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Yes I was already hooked on panties at 4 and was often seen walking around in aunts bedroom with her big panties. Can you imagine the sight? Mom told me these stories when I was older thinking it was just a passing thing. It wasn't.
I would say it was when I young, probably around 8 or 9, when I would find a pair of my mom's nylons and play with them in the bath room. It wasn't until I was in my early teens that I started to occasionally wear a pair of panty hose under my jeans. Later on, during my first marriage, I would start experimenting with wearing my ex-wife's dresses and skirts...even tried her makeup and lipstick in private.
To some extent the question is what is mean by dressing as a CD. If it means just putting on a few female articles of clothing at home, I did this when I was very young, perhaps 10 or 12. If it means going out dressed androgenously, I did this in my mid 20's. If it means going out in a complete female outfit, I would answer my late 20's.
In any case this was much too late and I wish I could have gone out dressed fully as a CD when I was much younger. So much time lost.
The bottom line here is that I have wanted to CD ever since I could remember. It has always been a part of me.
My first memories of cross dressing are in my mid teens (I had no opportunity earlier as i was away at a boys school for the previous 10 years) when I tried on my mother's clothes. Perhaps a little earlier i do remember being fascinated by my mother's big heavy corset and suspenders.
The first time I crossdressed, I was 13. I put my mom's panties, dress and heels. I was in heaven.
It was Halloween when my older sister thought it would be fun to have a little sister to go trick or treating with.
I was around six y.o. I have heard. when She put a old red dress of hers on me and a mask of course and she took me around
the neighbor hood introducing me as her little sister if anyone asked. I was hooked and wore her dresses of and on
until the day she moved out
I was always fascinated by women's boots as far back as I can remember, my mom had a pair of leather 70's black knee high boots with platform heels that I'd be allowed to wear during playtime, that would have been when I was 6 I guess, I loved the feel of my legs and feet encased in those boots and the feeling of a heel under the foot too, i got to the age when I was told off for wanting to wear them, guess mom thought I should have started to grow out of them by that time!
I was 10. Folding laundry one night I found some curious items that made me feel squidgy inside. Mom and dad took square dance lessons on Fridays nights for some reason and sometimes my brother and sister were out too. I tried on the bra one such Friday night. Nice. Then the girdle and the slip. Oh my god! I remember hooking stockings one night but probably not then.
It only took a couple of dress-ups before I was caught. Mom and dad were surprisingly cool about, considering it was about 1967. I recall them, or at least Mom, allowing that it was OK if I wanted to try those things out. I was way too embarrassed to pursue anything though.
A few days later the kid across the street claimed to have seen me through the window 'in a dress and everything.' I don't think anyone believed him and he never mentioned it again that I remember. That's kind of odd now that I think about it. Anyway, all that failure was enough for me for a long time.
My first memory, would have to be , as vague as it may be, something to do with me having to wear green tights for a school play (aged approx 5-8) ....I could have been the tree....not sure.
Next I remember, I'm trying on my mother's tights when my parents go to town....and getting caught once or twice puts me off for years with guilt, shame, abnormality,etc,etc.
My gosh, the firt time like most everyone was with mom's panties etc, the last time was 5 minutes ago !
I was between 3 and 5 years old...hard to remember back that far.