How old were you when you started and who's clothes?

I definitely started with my mother's stuff. I was an only child, a latchkey kid after school from age 9, so I decided to act on my interest in her lovely clothes. Started with mom's outer clothes, dresses and skirts and stuff, but by the time I was 11, I was into her lingerie and hosiery and heels, as well.
But since it was just my mom and I in the house -- father having split when I was little -- she knew exactly who was leaving wrinkles in her good work clothes. She confronted me about it when I was about 13, but instead of forbidding me from ever doing it, and thus driving a wedge between us, she was supportive of my CDing. She chose to buy me some of my own clothes so I wouldn't muss her clothes up -- some outfits, lingerie, shoes and a shoulder-length wig -- and taught me how to look right in them (like how to walk, talk, sit like a girl, do makeup and nails). She missed having a daughter and enjoyed it when I dressed as one. Basically, if I had my homework and chores done, I could dress en femme around the house sometimes. So I was extremely fortunate to have the mother I did.

Karen :)

mother's stuff when i was 7 x_x...

then i moved on to stuff my cousin never used anymore when i was 13 and above.

then moved on to buying my own stuff ^_^.

I think it's fair to say.... good on you mum

We lived in a small house with a single bathroom and my mother would sometimes leave her negligee hanging on the back of the bathroom door. It was a beautiful garment, made of blue silk covered with a layer of shear white chiffon and delicate white lace. I’d be standing at the sink and I’d notice it in the mirror. The negligee seemed to me to symbolize something joyful and carefree, an effortless beauty and a graceful opulence. One day when no one was about, I locked the bathroom door, stripped naked, and put on the negligee. The few moments in which I dared to wear it were intoxicating. It’s hard to recall exactly how I felt; I know it was exciting and sensual but it wasn’t sexual, I didn’t masturbate, that was still a few years away.

I can remember one time, a long time ago! today, I am 35 and I was 4-5 when I was really intuned with my female side. I can't remember who it was? but, I came to her and touched her pantyhosed leg! It was so innocent and that was an exact time when I knew, even as a boy at the time! This was my awareness of being a girl at that exact moment! Though out my life as youngins, I fastly became more aware of my female intuitions! My adolesense I started dressing up as a girl and well in my teens. Today, I have come a long way baby! I am a vibrant and gorgous plus beautiful "Women" today and every day! through various ways! so, thats a little bit of me! stay sexy n have fun! Ron/Eileenxoxo :)

I was 11 when I first tried on my sisters cute panties unfortunately she didn't catch me :( . Well it has been on and off from then on and when I got my own place I really found out how Lois felt in sexy lingerie. Love the look and feel. Even though my wife has forbidden me to be Lois I have found the time to slip into a pair of sexy panties and visit the forum :)

My dressing started when I was about 9yrs old in my sister’s clothes. I was a bit envious of her I suppose when she seemed to get so many new clothes and I did not. One Easter she got a new red velvet dress, it was the prettiest dress I had ever seen and to this day I don’t know why but I just longed to try that dress on to see how it felt. Up until then I had never had any though of dressing in girls clothes but about 3months later I was left alone in the house for about 2 hours while my mum and sister went to my aunt’s. It was the opportunity I had been waiting for and I quickly ran to her room and found the dress. I took off my shirt and trousers and slipped on the dress,
I then wanted to go the whole way and quickly found a slip and knickers. I took off the dress put on the slip and knickers and put the dress back on. I think at that moment Emily was born
From that day on I sneaked into my sister’s room and dressed whenever I had the opportunity, never getting caught but had some near escapes.

I found my Mom's winter clothes one summer and played in them for a while,. There were other occasions in my youth, but what really got me off the wagon completely was finding a school dress someone had left at school. It must have fallen out of someone's bag, because it was sheer providence that I found it. I have not looked back since.

14 er 15 somewere in there im 18 now cant stand not being in my 'real' clothes not dressed now but im going to go get some outa my sisters room its 1:21 i like sneeking in there and trying not to wake her up and then i put some lip gloss on and act all girly while she is sleeping its so cool

Must have been 15 or 16. My mum went on holiday and I tried on her leotard. I felt wonderful and from then on I have loved to dress. :)

I have a particular fondness still for tight clothes, leotards, corsets, catsuits, I love them all and high heels, mmmmmmmmmmm................. :)

I guess I have a lot to thank my mum for !

Andrea

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Originally Posted by morph

My mama didn't have no girls. Just boys.
She liked to dress me up and call me her "daughter". I liked that. But daddy didn't . He would get mad at her and say she was making a "sissy" out of me. When daddy pasted away. I decided to let mama have her "daughter" back. I was 12 years old.
I'm 25 years old now. And my mama still has her daughter.

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And a beautiful daughter she has ! :)

It was just before my twelfth birthday the first time I dressed and it was my cousin who dressed me in her flimsy white lace knickers, lemon summer dress, white knee length socks and nice little black shoes with a small heel. I felt wonderful and really sexually excited. Needless to say I've been dressing Fem ever since.

my sister tights.

My mum showed me off to the neighbours in my sisters nightdress when I was 6 – she was convinced I’d make a pretty girl. Since then I haven’t looked back. Started dressing in my sisters ballet knickers and borrowing her skirts from age 7 or so, and always raided the bag of clothes destined for the charity sale – got several dresses and bras that way, but had to borrow panties from my sisters bedroom when she was out.

My first time Cross Dressing, was when I was about five or six years old around 1961-62, I was supposed to be taking a nap in my parent’s bedroom, while laying on the bed, I could not help thinking about my mother’s black bra and panty set. I went to her drawer, got them out, and put them on. I then stood on the bed so I could see myself in the dresser mirror. At about that time my mother came into the bedroom to check on me and saw me wearing her underwear. She made me take them off and go lay back down for my afternoon nap. :(

This was just the beginning of my crossdressing. In about 1961, I played dress up pretending to be a teacher, with stockings, heels, and some other cloths which my mother helped me put on. My father didn’t approve. And all this taught me was to do my dressing secretly and covertly as to not to get caught. I stopped crossdressing until about the fifth grade when I was eleven years old in about 1967. I would sneak to the bathroom and put on my mother’s bra, stockings, girdle (open bottom), slip, and shoes. Sometimes I would even put on her eye makeup and lipstick. :cool:

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Originally Posted by Jill

I was about 11 or so when I started my dressing. My sister dared me to try on one of her old dresses one day and I did. I was hooked after that and continued to dress through my teenage years. I had three sisters so I had quite a variety to choose from. How old were you when you started and who's clothes?

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I started at around age 5 or 6. I was young and I remember what a thrill it was to wear moms pantyhose.......and at the age of 7 or so it just exploded, and well here I am. Wow I must say you have lovely legs.......what kind of hose are you wearing?

I was 5 years old and it was my mother's pantyhose.However I was a few years older when I started wearing dresses etc

I was around 7 I think my sister (the one thats a year older than me,I have four older sisters)dawn got me to play dress up and barbies I loved it I would play everytime she asked even though I would get caughtand get a spanking it was always worth that little bit of time to be a girl. I think my sister knew before I did. :o

I was 7 or 8 when I first wore my sisters school knickers, it felt good but I had no idea why. I moved on to her panties and skirts. When in my teens I stopped and joined the Army to prove that I was a "real man". After a few years I married and the sight of a wardrobe full of lovely feminine things triggered off the desires again.

I was seven yo and took part in a Catholic school play. I played the part of a angel. wings, halo, white flowing gown The Nun painted my cheeks with rouge and my lips with red lipstick. By the time the nuns finished with us you couldn't tell the boy from the girl angels . I really didn't want to wear lipstick but the Nun didn't give me a choice. I was actually called "little girl".

Well that was the very 1st time that i looked like a girl and I still remember it like it was yesterday.
Hugs to all you girls.
Mia Lynn

I don't really remember when I first started. I think it was pantyhose. I was young and curious, so I tried them on...it felt very good, and then I was hooked.

I was about 4 when the girl across the road and I swapped knickers and clothes. She was the same age as me.

I was 12 yrs old and the oldest of 5 children so I was allowed to stay home one day while the rest of my family went out. I used to take a pack of cigarettes from where ever my parents would would keep them in their big dresser. Sometimes the carton would be in my dad's part of the dresser and sometimes in my mom's. On that day I discovered the carton in my mom's lingerie drawer. The carton was towards the back of the drawer and as my hand went through my mom's lingerie I felt unbelievable excitement at touching her bras and panties. The next thing I knew I was trying on a pair of her pretty panties followed by a pretty bra. I was instantly hooked and wore them under my boy clothes the whole time I was home alone. I started making excuses to stay home alone and it wasn't long before I was wearing her lingerie, clothes, makeup, jewelry, shoes anything and everything of hers that was totally feminine.

I'm not sure of an exact age but it was preteen i know. i collected alot of clothes from yard sales and such.

i was 10. my sisters dress me up,and i have loved it scence

When i first started i was around 11. I started with my mom's bra, panties and hose. I'll never froget the feeling of silk panties and hose,,,and still love it today

i started crossdressing when i was aboot 9 or 10 i was wearing my sisters clothes.the first time i did it was when she came home from the beach one day and took a shower she left her bikini in there to dry and later that night i took a shower and saw it. i dont no why but i decided to put it on. every night id go in there and try it on until one night she took it out of the bathroom. so when i had a chance i sneaked into my sisters room and looked for it. i kinda forgot aboot it when i found her pantie drawer. she had alot of cute panties so i grabbed some and ran into the bathroom.

I was about 7 years old when i wore my mommies panties.She caught me and dressed up in my cousins panties,slip,stockings ,fancy pink dress and patent leather shoes. She sent me out to the store and i had to pick a specific item ,buy it and bring it hom.She told dad and he started calling me:sissy,pansy and girlie from then on.

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Originally Posted by Jill

I was about 11 or so when I started my dressing. My sister dared me to try on one of her old dresses one day and I did. I was hooked after that and continued to dress through my teenage years. I had three sisters so I had quite a variety to choose from. How old were you when you started and who's clothes?

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Jill, i was about 4 or 4.5 when i started crossdressing. i really enjoyed my sisters clothes. she was almost 7 yrs older. I have been dressing since that time, with very little time off. i am now age 55 and today will be speaking to a psychology class at the university here in phoenix. Yes, i will be dressed.

I remember that I was in Junior High School - well, not in school. I was at home. I don't exactly remember what made me try on my mother's clothing, but I remember I just did dresses at first. Then, as time progressed, I tried a bra. It eventually led to make-up, jewelry and nylons (with a garter). I still remember one black dress that I used to wear. Fortunately, there was a black bra to go with it.

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i started at around 6 or 7 when i disocovered my mom's pantyhose... they've been my favorite part of dressing ever since
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Panyhose is what really got me going also...loved the way it made me feel..

I was 5 years old when i tried on my sisters pantyhose,i was hooked,would put them on all the time,till I got caught and yelled at,then i had to do it more carefully.I had 5 older sisters and clothes were always all over the place,I miss those days

I began when I was 5. I had a little time after kidergarten before my mom arrived home from lunch (the good 'ol days when a five year old could do walk home alone). I wore her pantyhose and it was delicious!

I started when I was about 14. Loved to wear my sisters dance tights and some of her costumes. Have been dressing on & off now for about 20 years. I don't have any plans on stopping either!

The earliest time I can rember is the first grade when i came home from school because i had an accident and teh weren't clean boys underwear so my mom gave me a pair of my sisters. After that from time to time I would try on my mothers and sisters bras and panties. When i got older igot brave and even bought some of my own clothes. I would always throw them out after a while for fear of being caught. This has happened a couple of times and I even got rid of an expensive wig. BUT I always end up comming back to dressing up and loving the way it makes me feel. I will buy more clothes and probably stop getting rid of them.
I know this got off the track a little sorry.
Any how I started young

Dee anne

i was 6 years old when I first wore moms panties and bras. She caught me in her pink undies and was furious. She dressed me up in a little girls outfit and sent me outside to the local deli. i was scared but loved it.She told dad and he started calling me a sissy,pansy and girlie boy from then on.My aunties felt sorry for me and helped by puting my hair in curlers every night until I was about 10. They also did my nails for me.wow was that great.
Love,

girlieboy

I was 4 first time I dressed. I know this because I was dressing to gain attention from my parents while I was ill (it's a long story). Anyway... I was dressing in my sisters clothes, (she was Five and a half) it was just knickers a tartan skirt and a jumper the first time. Within a week I was in my mum's nighties though, and from there on in.... it just got better ! I do recall though, my fave' thing to wear was my sisters ballet leotard. :)

In my twenties...a dress from victoria secret!!! It was just the beggining :)

16
mother's bra and girdle.
it felt fabulous and i was hooked.
can't recall what initiated the feelings though, the very first time?

Love all you dolls!! I started dressing in girls' clothes about age 11 when the girl next door asked if I wanted to try on her clothes. She said I would have to wear all her lingerie, too. I quickly said yes, and that was the start. I have loved dressing as a female ever since. I thank that neighbor friend so much for opening up this wonderful world we all enjoy!!

Kisses and hugs to all,
Peggy Sue

5 years old. My earliest memory. Sneaking in and trying on mom's panties. Then I painted my toe nails a while later.

Then I found the closet...

around thirteen after my not so nice father left us.
started with mom's clothes.
karen.

Mother bought me a shirt which she then discovered was a blouse when we got home.

Not attatching any importance to it, I gladly wore it many times.

As for dressing on my own....

Wearing mother's lipsticks and leather skirts at about 13.

I was 10 yrs old and my Mother had just remarried , we moved to a new house and I found a box of her old clothes and lingere in a box in the basement . I tried them on and became so excited I came in the transpant blue and lace panties I was wearing. I found every excuse to play dress up until I was caught by my step father who dragged me to my mother and laughed and humilated me infront of her and then spanked me for being such a sissy and mommies boy. Little did he know he just got me hooked on getting punished in petticoats

I would've decked your step father if I were in your shoes. Oh and welcome to the site.

I was 11 and one day had an overwhelming urge to try on one of mom's girdles. Back then, the Playtex rubber girdles were the norm --- and they were/are WONDERFUL!!!. Once I had it on and properly adjusted, the feeling was wonderful!! I have been a confirmed girdle girl ever since. Once I was on my own, I then started buying my own clothes. I was ecstatic when I bought my first outfit --- Cross your Heart bra, Playtex girdles (of course), some nice satiny lacy full slips, stockings, 3 inch heels and wig. Over the years, I have accumulated a sizeable wardrobe.

Oh, I forgot to mention --- among my first purchases of my own were several nice dresses. It was fabulous when I was able to wear my very own dresses. I have always preferred to wear dresses and skirts....... so much more comfortable than pants. Just wish I could wear them all the time!!

I started when I was 19. My two best girl friends gave me a pair of boyshorts as a gag gift...little did they know that I cding was something I wanted to try! After I put them on once I was hooked. I had been interested in female clothing since I was about 13 or 14 though.

I Was about 10 yrs old, and innocently pulled on - My Moms boots to run out and check the mail early on a Saturday(blizzard) morning,, the way they felt-on and looked on- and,,then soon after,ventured into trying on ,My cousins, pvc rain jacket,, soooo onward and -Upward!?

i stared when i was 13 wearing my mums stuff first it was the dress she had this blacklace number i used to dress when she was away shopping.from there i started trying on her underwear all the lace & satain i was hooked every chance i had was spent i her bedroom i was the same size as her so it all fitted me even her shose i still have that blacklace number much 2 my mothers hatered i still dress every day trying to make myself pass in public .