How old were you when you first wore women's clothes?

[Davina-Alba]

I think I probably wore girls knickers from a very young age. I was an only child but I had a lot of female cousins. Back then (the 1950's) attitudes to childred of both sexes bathing together or sleeping together were very relaxed so from an early age I knew that I looked different from girls "down there". One of my aunts had 5 daughters and no sons and the girls were intrugued by my "extra bit" which we soon discovered got stiff if you played with it.

Anyway, I often slept over at my aunts and remember being given girls pants to wear if mine were not fresh and even slept in nylon nighties if I'd not brought pyamas. This happened quite regularly as my father was very ill and ended up in hospital without warning. When that happened I'd be picked up from school by a cousin and so didn't have overnight things. Of course my mother could have left stuff there but the fact was that no-one thought there was anything wrong with a boy wearing girls things.

The first time that I wore female attire and realised the sexual connotations was when I was about 8 or 9. There was a fancy dress party of some sort and as money was tight the decision was taken that the cousing of about my age would go as "Tommy Tucker" a children's character of the time ("Little Tommy Tucker sang for his supper - if you remember the nursery ryme). This was her wearing my school uniform, shorts, shirt, tie, cap etc and carrying a football. I was to go as a St Trinian's Schoolgirl. As I was much taller than my cousin I wore her older sisters school uniform complete with suspender belt and stockings (and carrying a hockey stick). My "extra bit" was very happy with this so much so that two of my cousins had to help me get it limp again.

The rest, as they say, is history!

[Britney Styles]

I was in early puberty when i started wearing pantyhose and womens underwear. I had a fascination with pantyhose since I was a small child. Later in high school I put on an ex girlfriends work outfit, black skirt, white top, black sweater, wedge heels, and pantyhose. This was my first experience cross dressing. Later in college I started buying clothes and shoes that properly fit. I recently just bought a wig. I hope to go out in public someday.

[Kelly_on_platforms]

I think i was about 6...but can't tell for sure. My mother always kept lots of clothing for my cousins at home....and I knew where she kept them. It was a little girly sundress for me the first time. I also remember wearing my cousins summer sandals, but they were a little big on me at the time, but i still enjoyed it a lot. Back then I spent as much time dressed as I could. My parents worked long hours when I was young.

[Jill M]

I think I was about 13. Started wearing my sister's panties, skirt, and silky top. Loved the feeling.

[AmberM]

I was thirteen wearing my mom's white bra/panty set with a little black dress. It felt good, and sexy.

[Julieanne]

Oh my -- the older I get the farther away it becomes. As far as I can remember I've always been a crossdresser. I cannot remember when I was not, so I guess that puts it at 6 or 7? 10 or 11? Either way I've been crossdressing for 5 decades or so.

[Alberta Daisy]

22 years old. My then girlfriend and I had plans for new Years Eve, and I was grousing about the time she was taking getting ready. She said something about if I thought it was so easy, maybe I should try it myself. Being well primed on booze already, I called her on it... Needless to say, plans were aborted, two hours later I was fully decked out from head to foot in matching bra, panties and garter belt, cocktail dress, nylons, strappy heels that her Amazon roommate left unsecured, and a HUGE updone wig. Best New Years ever, and Daisy was born.

[Lilaka Ananda]

I was 18, staying in my girlfriend's stepmother's ski cabin the year I lived as a ski bum. My landlady kept a wardrobe there of various items, and one night, on a whim, I tried on some pantyhose and lipstick. A star (in her own mind) was born that night.

[Avana]

5

wearing my moms clothes and playing house with the neighborhood girls. i used to always play the baby daughter.

[Jaclyn NM]

Probably about six or seven, when I first tried on my mom's high heels, and then her stockings, which really turned me on and started me on to becoming the crossdresser that I am today. And I can honestly say that I have no regrets. I love who I am, and I love wearing my female clothing, especially stockings, and really high heels.

[Rilulia]

If I remember correctly, I believe I was about 7. I just tried wearing my older cousin's clothing just because they were laying around. I have to say, girl's clothing feels so much softer than boys.

[Janine G]

I was 8 my mom (single mother) had me stay with my aunt for a week while she was caring for my grandmother. I didn't have any pajamas, so my aunt dressed me in my cousin's. I remember them like it was yesterday, they were like a yellow camisole and tap pants. I remember lying on the floor watching TV before bed with my cousin enjoying the feel of the satin on my skin. That same week I started to "borrow" my cousins panties.

[drjoancds]

At the age of 8 y.o. or thereabouts: I grew increasingly curious and tried on her panties and nylons and clopped around on her still-too-large heels and she thought it was hilarious and saw no harm, I was still a boy, riding my bike, playing rough with my siblings, catching worms and fishing. My dad took me hunting, I was in the Boy Scouts. At 12 y.o. I was an altar boy in the small town's Catholic church and I LOVED the cassock and surplice I wore serving the priest during Holy Mass; it made me feel angelic, feminine, and yes, it was pretty much a dress, for all intents and purposes. Then I was into mom's or my three aunt's lingerie/nylons drawers and perfumed church-going black kid leather gloves whenever I could 'visit' them clandestinely....and intimately.

The rest is, as they say, 'Herstory'...[/QUOTE]

[drjoancds]

I too was an altar-boy during my formative and exploratory years, and until I read it here I thought I was the only one who ever fantasized that my cassock and surplice was a dress.

[drjoancds]

My first memory of interest in wearing womens clothing was one summer age 6 or 7, alone in the basement family room, playing, and finding a clean laundry basket. I discovered the proverbal mother load of her lingerie, slips, panties, bras, girdles with garters, nylons with seams. I had watched my mother dress before for dinner and dates out with my father. "Lorna" is right, wearing might not be the right description at that age, but for some time I was mom and getting ready to go out. The clothes litterally draped off my body, but in my mind they fit and looked good, especially when padded with couch throw pillows, and lord knows how i ever managed to not ladder her stockings.
I never had a sister, and no female relatives who lived close. It wasn't until 2 yrs later wher we lived in another town that I struck it big time. Our downtown church bought the building next to it and converted the ground floor into a resale donation thrift shop. Clothing of all sizes, styles, colors, outer and under wear. My mother worked sorting and hanging clothes. Needles to say I was expected to volunteer help also, usually fridays after school. The church had sunday school classes in the upper rooms. After church on sunday while the adults were at coffe hour in the parish hall I visited the closed thrift shop and exchanged any clothing I had borrowed the previous week. The trick was to always leave the clothes in better condition than when you borrowed them, cleaned, folded, mended, etc. Never was discovered, and it went on until the church tore the old building down for a parking lot about my senior year in HS.

[StacyCD]

I don't remember that far back! However, I know that I was interested in woman's clothing between 4-5. When I started wearing woman's clothing is a mystery that is forever lost.

[Barbara Dugan]

38 years old but I started having urges 10 years before

[Jill Devine]

I was 5 years old! I can vaguely remember sneaking into the basket that contained the clothing that had been washed but still needed to be sorted and/or ironed. Tried on my mother's pantyhose and the rest was history. But even before that I always wanted girls clothing instead of boys. But I kept the desire very secret and pretended to hate girly stuff.
Denial 101.

[Salina]

I was 15, my bedroom was in the basement which was 1/2 finished. The laundry room was in the other 1/2. One day I walked in the laundry room to get something and there were a bunch of my sister's panties hanging on a line to dry. I recall being intruiged by them, but did nothing that time. Every time my mom did laundry I would go check to see if the panties were there and the urge to try them on became stronger and stronger, it was like they were calling my name,....one day when home alone I broke down and tried on a pair of her nylon day of the week panties and was hooked immediately.

[Pinky188]

I was around 10 or so. I would go in my sisters room and put her clothes on! She is close to my age so they all fit! She had good tast also! She never busted me!

[cdmichelle48]

I don't remenber how old I was, it was before kindagarden, My sister and I were in a small room and we found a pair of silky ladies panties. I tried them on and even at that young age I was arroused. I never tried on clothes with my sister again but after that I was hooked. Every chance I got I'd sneek into the girls room and try on their clothes. I loved the feeling of the panties and panty hose and putting on their skirts and dresses, the feeling of being a girl. Very, very few people Know of my crossdressing. I wish I could dress more often and go out in public and pass as a woman. A lot of you CDs on this site are very beautiful, congradulations.

[susan2010]

I was 4 or 5 the first time I remember, but it may not have been the first time. For some reason I had to try on my sister's full white petticoat. I loved the softness and scratchiness. I wore it many times after that until she married and moved out. Then I discovered mom's slips and nightgowns. 50+ years later I still love petticoats and slips.

[alexiss]

First time...I was living with my girlfriend and she suggested I put on some of her lingerie. I indulged and liked it.

[alexiss]

That was 20+ years ago.

[alexiss]

I'm still shy about dressing... but I did buy a pair of heels today