When did you first crossdress?

[GeorgeA]

I copied my post from a few years back as it is relevant to this discussion.

When I was about 4-5 years old I searched my aunt's dresser drawer where I knew she had a bag of candies, next to them were several of her nylons. I tried to pull them on my legs but of course they were too long for my short legs. I tried another and another but none would fit.
Many years later I would sneak my mother's panties and nylons and they were much better fit this time as I was about 12 or 13.
It was only when I started to work that I acquired a collection of lingerie from a mail order catalogue.
To this day nylons, garter belts & slips are my biggest attraction.

[Missy]

I remember wearing my sisters under cloths to play female roles with the boy next door who play the male role got hooked on wearing bras and panties and every thing else at that time in the mid to late 60's

[Quksilver420]

Do you remember the first time you tried on an item of women’s clothing?

I remember putting on my mum’s fake fur coat around age 7 and getting a thrill from my appearance in the mirror. I knew at once that this was part of my future. How about you?

I really don't remember my first time. Only thing I can is that I was a bed wetter. In preschool, after naps I would have wet clothes and 90% of the time no change of clothes. Most days if I wet myself I would go home in girls under ware. Cross dressing just snowballed from there.

[TonyaV]

I may have been born with. I can trace it back unit I was a young child.

[Xandra]

I have really enjoyed reading all the replies. Please keep 'em coming.

[Patty]

Early grammar school 5th grade I think. It was been soon long ago.

[Robin777]

I believe it was 12 or 13. I remember starting with my mother's panties and going from there. It all started with panties, then putting on a bra and slip,then a dress. It went on from there. I remember when I was younger ,I always liked looking at the sears and penny's catalogs. I always went to the women's section. To this day I enjoy shopping for ladies clothing more than mens.

[Trisha65]

Apparently shortly after my birth. I have three older sisters and I have seen pictures of me in hand-me-down sleepers that are obviously girls sleepers. After that, I can remember my sisters dressing me up probably from 3 on. Never objected and never took the clothes off until bedtime.

[regina young]

When I was a very young 6 or 7 year old boy we did not have much, but neither did most of the kids I knew so we really did not realize at the time we were poor. every summer my parents would send me and my brother to live with an Aunt and Uncle who had a small farm, we helped to milk the cows, feed the animals , gather the eggs, work in the garden, etc. One Sunday we were to go to church and I really had no suitable shoes so my aunt put me in my cousins shoes, she was a Brownie and the shoes probably were not that feminine but to me they were girl shoes. Anyway I wore them, they fit, and it was only for Sunday's. A week or two later I had no underwear clean to wear so she put me in a pair of my cousins step-ins, as they called them, they even said Tuesday on them. My protestations were overridden, as I was not what you would call a rebel...yet. Anyway, I liked the feel of the cotton panties and they were in much better shape than any of my own. When I returned home there they were in my bag, I quickly tucked them away, out of the eyes of my parents and would take them out to wear when the opportunity presented itself. So that was the first time I suppose. Funny I have been looking for a set of those day-of-the-week panties now for some time...someday.

[Sami]

For me since 8 or 9 years old and have done ever since

[Jasmyne]

First time was around 8 or 9, during a summer break from school while being left home alone. Tried on some of my mom's panties and a nightee, the feel is what hooked up. I even tried some of her lipstick as well and spent as much of the day as I could like that. Sadly, I've not discovered how much a part of me it is until just recently

[Xandra]

I remember "borrowing" my mum's lipstick when she was out and seeing how my lips looked. So much better!

First time was around 8 or 9, during a summer break from school while being left home alone. Tried on some of my mom's panties and a nightee, the feel is what hooked up. I even tried some of her lipstick as well and spent as much of the day as I could like that. Sadly, I've not discovered how much a part of me it is until just recently

[edith]

Getting into my mom's makeup at around 6 years old, and stuffing balls of yarn down my shirt.

[immike]

I was 6 years old. I was enchanted by pantyhose. I found a chance to wear my mother's hose along with a skirt and blouse. Of course they did not fit, but I was thrilled and began pursuing crossdressing as often as possible. Over forty years later, I'm fully dressed as I type this. The thrill has never escaped me.

My thrill was going
into Mothers closet&finding her French Maid costume from halloween&simply went into her drawer&borrowed new pair of black
pantyhose&put them on&slid into her costume&stepped into a pair of her black heels

[Christina89]

I started cross dressing at the age of 12 when I came home from school one day started watching tv and while I was watching tv I got the sudden urge to try on women's clothing. so I went to my moms and tried on one of her old bikini bottoms and I loved the feel of them on my body.

[Dani0948]

When i was about 9, i frequently played dolls and dressup with my 2 younger sisters. What i remember most vividly was trying on a pair of high heeled pumps given to us by our next door neighbor. I was really sad when i outgrew them.

[Selma]

I always had a fascination for stocking so I had two choices: Put one over my head and rob a bank or wear them on my legs and become a cross dresser.

[Courtney . J]

I always had a fascination for stocking so I had two choices: Put one over my head and rob a bank or wear them on my legs and become a cross dresser.

i love this site ,. some very funny girls in here . :D

[Emmalee]

Pre school in culver city I would wear dresses at the dress up station and I would play with dolls, I told Miss Audry I wanted to be a Ballerina I guess I was always a bit of a princess

[Joy3]

I was about 5 or 6 I believe and a neighbor girl [Cathie] asked me if I would be her "girlfriend". She was my only playmate at the time so I said yes. She proceeded to dress me in her clothes. She also loved playing with her mothers make-up and putting it on me. I loved it! I then started using my mothers things when I was alone and I was on my way.

[tiffanyjo89]

I must have been about 8/9.

I ran out clean underwear, and my mom was NOT going to have me wearing dirty underwear, so she told me to wear a pair of my sister's. I said, effectively, HECK NO! I didn't want to wear girls clothes. What self respecting boy does? But after I got used to wearing them, OMG, I really liked them. It was a basic cotton pair of girls briefs, but they were so much softer and didn't bunch up like my underwear.

I kinda knew that my sister had different styles as well, and as time went along, I really grew to like the different styles she had.

[deborahtg42]

when I was born I got placed in a dress and never stopped crossdressing since then, lol

[aly01]

Was about 10 or 11 tried on slip and panties of sisters.

[devida]

When I was 7 or 8 I used to dress up in my Grandma's clothes when she was out of the house. The I'd march up and down in front of the mirror. Don't all boys do that?

[Pinky188]

As soon as I realized what a dress was.... I was young.