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

[linda1977]

My first crossdressing experience was when I was 6, although I always had the urge to wear female clothes before then. This happened during a Xmas panto performance/rehersals in my infant school, where my friend and I took on the roles of "Kings of Topsy-Turvey Land" in Sleeping Beauty. We were "topsy-turvey" because the top half of our clothes were masculine, but we both wore a mini-skirt and pantyhose below! Looking back, I should have been embarassed about that cruel joke put upon by our teacher, but I wasn't. In fact, I was SO pleased that I was given the opportunity.

It was when I reached the age of 11 that I finally had the courage to fully cross-dress, and have continued to do so for 22 years and counting.

[Cassiecd]

I guess this is where I stand out from the crowd:

I started at age 50

I stumbled into cross dressing accidentally, a game of sorts with my wife. ZOWIE! What on earth was I waiting for? I am definitely hooked, but she no longer participates.

[kristinacd55]

Well first I started with girls clothes, since i was 6 or 7 Women's clothes came when I got to be a woman's age.......18? 19?

[CindyT]

It was at about 5 or 6 for me. Mom's girdles and nightgowns, I always liked that silky feel! I was hooked right away!!! When got to be about 17 or 18 I finally got the courage to buy some womens clothing, mostly undies and pantyhose.

[juligirl1984]

I dressed first when I was in 2nd grade. I just moved back to the east coast and was home babysitting my sister after school. Mom was not home so Id put on her bra and do chores with it on. then I tried panties and a bra. after that it kept going to anything she had. I never stopped, I was caught once in my sisters dancing tutu lol! and in my moms bathing suit when I was 14. I was never caught by my mom, just she would find her clothes in my room.(oops!!! LOL!) so maybe she kinda knows?

[Terry V]

I have replyed to this thread before but I was about 9 or 10 and my aunt caught me trying on my cousins panties and wanted to know if I wanted to be dressed as a girl when I said yes she dressed me in her friends little girls Easter outfit and I loved it with a frilly yellow dress and petticoat underneath I always had the desire but when I had that dress on it was more than I could understand but all these years later I thank my aunt for showing me this world I live in and shared with her for many years after.

[gaylegirlify]

I guess i was around 15 trying on knickers and bras, crossing my legs pretending to be a girl, i new i was a girl right there and then.

[DKA]

My first time I was around the age of 7 or 8 - maybe sooner but, thats the earliest I can remember - I know I loved the feel from then on. they were my older sisters and my friend dared me 2do it, I was apprehensive at first then I loved it!

[katrinakat]

me too!!!! all day while my mom worked!

I remember staying home sick from school in the third grade by my self for the first time ever and spending the day in moms bra and pantyhose and sisters skirts and shoes. I know I would try on their panties any chance I got before that and recall being jealous of my sister wearing a type of body suit that I couldn't. That would have been at 4 or 5, but I honestly don't remember the first time I tried on my sisters underwear.

[Tallulah Rose]

I think it's interesting that so many of us started dressing so early on in life. I was about 5 years of age and I was drawn to my mothers high heeled shoes (which were far too big). Then came the stockings. That was the "slippery slope" for me.

[Rebecca Sue]

I grew up in a house with a lot of women and was always slipping into feminine things.

[juligirl1984]

I started at age 7 or 8. I think. I do know it was after parents separated. Maybe what triggered it. I always got yelled at earlier than 7 for touching my moms legs when she wore hose. I do remember that clearly lol!

[Tammy V]

I was probably 6 or 7 at the oldest. I was either 8 or 9 when at my grandmother's house I put on one of her wigs, a dress and some of her shoes and jewelry and walked out in front of her and her sisters. They all got a big kick out of me, but when my garandad came home he was not amused and it was off with everything.

[crashd0309]

I was about 8. I loved the silky feel of my mom's nightgowns. Soon I wore everything of my mom's. I sort of got caught when i was around 10. Mom found some of her clothes scattered about when she came home and she confronted me about them. I was so embarrassed I never did it again....until a few months ago when my wife was behind on laundry and I put on a pair of her panties as a joke. I've been hooked since!!

[Kaz]

10 - 11? That era...

[Billie Jo]

I was probably about 5or6 I only had girls to play with so we dressed up and they dressed me up and their I went

[GeorgieMacD]

My mother came from a family line that dressed all their young children in dresses until about 2 years old. I guess that was a passive start. My first memory of actively trying on clothes was a few years later. My mother always walked around the house wearing bra, girdle and stockings and sometimes a full slip. I remember my fascination with the soft clothes and was always nearby when she dressed. She would let me play with her soft clothes and regularly helped me play dress up. It was certainly the defining time for a lifetime of dressing up. I remember vividly being 10 and in fourth grade when my mother wore her first pair of tights. I just had to have some of my own. She got them for me and they became the first item that was exclusively mine. She added to my collection regularly over the years until I started buying my own soft clothes.

I plainly remember my father's negative reaction to all that and my mother's whispers to him that it was all right. Ironically I found out some time later that my father was a cross dresser. It explained a lot about Halloween and other memories.

[juligirl1984]

lol wow go figure, you dad was a cross dresser and got mad that you were one! maybe he didnt want you to go thru the ??? that he did. that was nice of your mom to support you.

[WheatishCD]

Hi juli, nice topic.
i still remember when i was in in 5th grade i saw my mom all dressed up. she looked so stunning. the moment she went out i just raided her wardrobe. since then it is no looking back.
luv
reni

[latexlover]

I was 15 when I started to crossdress. I had between 10 - 12 pairs of shoes and 3 outlets, but some years later my mom look thru my closet and found the shoes hiding and got in trouble , but later down the road at 21 i was married and back crossdressing when the wife wasn't home and still til today i'm still crossdresser but with a little time to dressed up

[Karen kc]

I was 6y.o. and on a cold January evening the old floor furnace quit,in order to keep me from freezing, mom made me wear a pair of her bright red tights. Wasn't long after that, my oldest brother caught me putting on lipstick! The rest is history!!!!

[Ellenor]

Around age of 10. I had no sisters and was part of a very male dominated house so any weakness was not permitted. Anyway I was a paperboy - humm - paperperson? anyway and saw a customer's bra hanging on the clothesline - well it came home with me. Then came the bathing suits, on clothes lines of course. Then the bras in grocery stores -- easy to take. Not making any excuses - just telling it as it was for me.

[Donna June]

Around 7 or 8. I was lucky in that I had a sister two years older than me who was cute and feminine. Years later when she went off to college, but half of her clothes were still home, I had the time of my life

[CallMeEmily]

currently the story of my life lol.

[Lynn Pennington]

I was fasinated with ads showing womans cloths when I was about 4 or 5,and started dressing whenI was 12. I had a big family besides my mom I had 3 sisters,and always waited till a some cloths piled up in the bathroom,then I would take time with my shower .Trying on things.I loved wearing nylons a girdle and bra stuffed with socks. It was such a sexual turn on.Now I enjoy dressing,and looking and feeling sexy. I can get the turned on feeling if I want to,but rather sit around dressed,and admire myself.

Carolyn