What was the first item you wore and at what age?

[chris.deee]

First was my grandmother letting me play with her jewelry at her apartment around 7.

After that, it was a towel plus using bath crayons as makeup in private around 10.

First wore a bra and got dressed at 12 when my mom started going back to work. 

I bought my first pair of heels at 23 and switched to having my own wardrobe by 26 when I came out to my wife.

[Rafaela]

a pair of stockings at around 5 or 6. I remember loving how smooth and nice they felt, and rolling around in my parents' bed. When she came in and found me it was weird 
Haven't worn anything like that in a looooong time.

[BeverlyAnn]

Panties and I don't even know how old I was.  I only have faint memories of it and it was kind of strange circumstances.  I was in a day care and I guess during nap time I had an accident.  Since it was long before the days of health codes, the day care actually had spare underwear for when kids had those accidents.  You would wear them home and your mom washed them when she did the laundry and then bring them back.  The day it happened to me, the only underwear they had in the cabinet was girls panties.  Like I say, I don't remember a lot about it but I do remember when I put the panties on, everything was right with the world and this was something I was supposed to be wearing. 

[possiblyrhianne]

I had to wear tights for a school play. Was embarrassed at the time.

If only I knew what I did now hahah....

[bree_davis01]

let's 12ish? wearing a dress my mom was getting ride of. after being caught by my sister, she shared cloths

Sent from my SM-G900V using Tapatalk

[AxelM07]

I guess I was about 12, and I wore one of my sister's guy shirts.

[Alex Forbes]

My cousin's black opaque tights. I think I was 12.

[jacquelynh]

A dress my mom made me try on,I was 7 or 8 years old when this happened.My mom thought I looked cute in it

[Elli.P]

Mom's bra, age 6. Was in the bathroom before bathing. She had D cups and walked in while I was trying to stuff dirty clothes into it to fill the cups. She was very angry and yelled at me to never do it again. But I kept doing it just didn't  get caught anymore.

[FrancisAnn]

That's funny. I loved to play dress up like any little girl would, age 4-5 I guess, red lipstick & red nail polish were so cool & my little feet in my moms high heels. My mom was OK with it but my father was not pleased. Oh & I loved pearl necklaces....any jewelry. Those were great days before my first grade teacher told me I was a boy...ugggg, she was so wrong but I was forced to act kinda like a boy, booooooooooooo.

[DianeofCarlsbad]

I know it was pre kindergarden, so 4 maybe 5 years old. Even after all these years I still remember putting on a pair of my mom's high heels. They were navy blue peep toe pumps. Standing up in them was just such a wonderful feeling. Shortly after that I began wearing her dresses along with the heels.

My mom was a nurse who worked nights so I think anything that could keep me busy while she sleep was ok with her

[Thea]

As a kid, I was always being mistaken for a girl. In the summer of 1972, when I was 12 years old, my older cousin asked if I would go to the mall with her to do some shopping. When I came out of my room in a halter top, short shorts and girly flip-flops, she was a bit surprised but accepted me as I was. She was a good friend then, and a great lady now. To this day, she's the only family member I have that knows my little secret.

[FrancisAnn]

Those were fun days at 4-5 years old wearing my mom's high heels. They felt great & I was such a happy little girl.

[kylie1]

I started with my sisters panties and moms lipstick when I was four.  I felt at home. I even wore my sisters panties to school on and off starting in the first grade.

[GdsMichelle]

20 years old barrow my aunts clothes for Halloween costume.

[Dee Marshall]

20 years old barrow my aunts clothes for Halloween costume.

Goodness! You reminded me...
One year when I was in grade school, perhaps second or third grade, my mother made a ghost costume for me for Halloween. We used to wear our costumes to school and mine came home dirty and ripped. Mind, at that age I didn't know I was trans, no one knew what is was and if I ever had known it was bullied out of me long before.

At the last minute all my mom could think of was to dress me as a little old lady, dress, heels, makeup, hat with veil and all. I had a great time and loved the costume. I guess a cis boy would have been embarrassed and would have refused to go out trick-or-treating.

Should have guessed then and there.

[Vanessa2016]

Sisters bra and panties at about 10 years old

[cdjenna69]

when I was 13 years old I found a bag with girls clothes in it. the first thing I put on was a black skirt and pink panties.

[Amy Chislett]

Two accidental incidences earlier: ten years old, Halloween - not my idea - done up extensively but as an older matroness.  At 23, was having passionate argument with rooms, they were gone, the rented place was filled with stuff - found a polyester white flower dress and put it on for kicks.

And then this first week of April was the first time I took my place in the bedroom and mail ordered black lace stockings w attached garter.  I'm 51.

[FrancisAnn]

Gosh, age 4-5 everything of my mom's I loved to play dress up in her heels, red lipstick, red nail polish. I was just a normal little girl. I've always been female & so glad for that.......