When did you first crossdress?

[Bima]

I have a vague memory that I at age 5 (or perhaps 4) for some reason wanted to wear my neighbor friends mum's coats when I was standing alone looking at the coats in the entrance hallway of their apartment, but I accidentally tore down the entire coat hanger construction in a feeble attempt to reach the coats. I don't remember if I could try a coat on or not in the end, or what happened after I ruined their coat hanger.


Swapped jackets with my first "girlfriend" at age 7. She had a girly orange and red winterjacket that I adored and really wanted to wear. For some reason, she was happy to wear my jacket, and we wore each other's jackets day long, and over a couple of subsequent days.


In my first school years, my first or second grade, 7-8 years old, my teacher had this long slim and beautiful dark brown leather coat with a fur trim which I tried on when she had left it outside the class room and everyone else where away for lunch. I remember that earlier on, the girls in the class had borrowed this coat and walked around the schoolyard wearing it, and our teacher had berated them afterwards. Anyway, I remember that I was really jealous, fascinated and for some reason also wanted to wear the coat and walk around the school yard. At that age, neither I nor them, where that tall so the leather coat nearly touched the ground. And then in the end, I tried the coat on, felt like a grown up woman, and I was in heaven. :-)

[Adriana Moretti]

10 years old? ish... Cousins ballerina dance recital costume found in my grandmothers closet.....

[Berta82]

Started somewhere around 6 or 7. Trying on moms underwear because I loved the feel of silk and satin. The next age I remember when it really took off was around 10 or 11. We had just moved and I would occasionally stay at my grandparents where my parents had stored things in the attic. I remember finding a giant bag of bras, panties, girdles, and stockings. It was heaven and I haven't looked back since.

[lesli]

Alexandra,
i used to run around the house in my mom's heels when i was maybe 4? i loved it! back in the day, there used to be small sample lipsticks that would be given out, and my mom would give them to me to play with--i loved them too.
hugs,
lesli

[Rebekka]

I was about 10 years old. I love the feel of silk and satin. I tried on mom's white blouse and was instantly hooked and I never looked back and have been dressing since then. The feelings are so very INTENSE........I love it !!

[Monet's dream]

I remember being in grade school and sneaking into my older sisters room when everyone was gone and putting on her clothes, starting with undergarment, girdles, etc and then trying on so many of her dresses. Guess I was lucky that she was so much older than I was so that she had enticing clothing - even back in the 60's.

[Julia NZ]

I was about 9 or 10 and was staying at my Grandparents place. It was a big house with lots of bedrooms where my aunts and uncles still had their own rooms even though they were all away from home. I was in an aunts room staying and in the wardrobe was a satin full length bridesmaid dress from a wedding we'd all been at recently.

Tried it on..........gorgeous! And the feel of the fabric..........unbelievable!

[Ally 2112]

about 11 years of age the cding had been working on me for some time ,I was whatching an epesode of happy Days nobody was home .i went up to my moms clothet found a dress i thoght i would fit
It was a feeling i had never felt before or since .But as much as i hate it at times i love it

[Brooke B]

I was about 10. I went to a relatives place by a lake. We went walking and someone had left a pair of white flip flops there. I drug behind long enough to be out of sight and then tried them on. Flip flops don't seem like much, but it was enough to be hooked for life!

[rah]

idk when but i remember when i was forced to do it when i was very young my sister with her friends put on a white frock on me and we went to the mall and i hated than

[paigecd]

since I grew up in the 80's and women actually wore pantyhose, I wanted to try a pair on so I started with my sisters pantyhose at 7 years old and the rest is history

[Debby1194]

I was probably around 4 or 5. A female relative thought it would be fun to use me as her personal Barbie Doll. After that I was hooked

[Caden Lane]

At age 3 I used to run around in one of my moms nighties. At age 7 I found some panties at a friends house. About that same age I discovered my moms square dancing petticoats and pettipanties. From there it was all history.

[Kristy 56]

Yes I do. I was in first grade and the girl across the street who was the same age had a dress up skirt. One day she left it outside. There was no one around so I grabbed it went behind a bush and tried it on. At least that's the way I remember it.

[Donnagirl]

From as young as I can remember... Three sisters made for a plentiful supply.

[ShelbyDawn]

I can remember being five or six and sneaking into my moms dresser and stealing her slips.
I still love satin and lace...
As I got older, I started "borrowing" things, panties, bras, dresses, etc., from my sisters.
Once I moved out on my own, it became more opportunistic; i.e., I would get lucky enough to have a pair of panties mixed in with my laundry in the apartment complex or a girl friend would leave something at my place.

[Vanessa Rose]

4-5 years old. Cousins basement play for parents. I had to wear that pink satin outfit with tutu. I was finished the second I had it on.

I felt pretty and perfect!

Vanny

[Tina B.]

At around 6, sister left her slip hanging on the bathroom door, the fit was bad, but the feelings where oh so good.

[Xandra]

That is a beautiful memory. Thank you for sharing. :-)

I was about 9 or 10 and was staying at my Grandparents place. It was a big house with lots of bedrooms where my aunts and uncles still had their own rooms even though they were all away from home. I was in an aunts room staying and in the wardrobe was a satin full length bridesmaid dress from a wedding we'd all been at recently.

Tried it on..........gorgeous! And the feel of the fabric..........unbelievable!

[K8astrophe]

My first memory of dressing in any form coincides with my first memory of being caught too. Wearing my mother's knee highs at about 6 underneath my footie pajamas. Just before bed my mom came to put socks on me since it was a cold winter night and I was caught red...footed...and faced. She caught me in pantyhose once later at 13... Not the slyest kid in the world.

[CD Husband]

We were at my aunt's house. She was (is) the type that wore pantyhose and heels everyday. I had to go #2 something wicked so she let me use her master bath, which was like finding the holy grail. In there she kept a hamper just for pantyhose and I couldn't resist trying them on. I was maybe 6 or 7. I had them about half on and the door flew open and there was my mother, wanting to know what was taking so long. When she noticed what I was doing, all hell broke loose. Not pleasant.

[stephannietv]

I started at age 11,i was so amazed how good it felt wearing nylons and figured if nylons felt so fantastic,why not try panties,bra,skirt,heels etc and the more I put on,the better I felt and still feel the same,maybe better when I get a chance to dress now

[chrissietoo]

I was in 5th grade when I asked my mom if I could be a girl for Halloween. It just came out of the blue (or out of the pink). I don't recall sneaking into her drawer (at least not before then)....but I admired girls and obviously wanted to emulate them. My mom took it as a crafts project and went to the thrift store, put together a lovely costume. The next I remember was slipping on my girlfriend's bikini and feeling euphoric.

[ArleneRaquel]

Somewhere between 1954 & 1956. I wore some of my mothers things, other than heels I don't remember exactly what. Starting in 1959 I wore her cat's eye frames when ever I could get the chance. She was supposed to wear new first pair of glasses at all times, but for the first year or two after her first fitting she wore them about 90% of the time. I sure did like my look waring red lipstick, red nail polish and her brownish frames. I sure did give me a rush. Her next pair were silver cat's eye, which I don't believe I ever borrowed. My mother went to an ivory cat's eye frame. I believe she looked her most ravishing wearing the ivory frames. Staring circa 1970 dhe went to wire non-cat's eye style. By 1970 I had my own female frames.

[Christen]

I think I was around 6 years old. It was a little embroidered beige cardigan. Belonged to a girl who visited our house. I can't even remember her name or whether she was a relation or not. The compulsion to try it on was so strong.