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

[leatherdres5]

I was about 14.

Mom's blue denim skirt.

[Allison Wunderland]

Bath towels as skirts, about 4 yrs. old. And so, is it trans, cross, ambiguous, or sometimes a towel is simply a towel, to paraphrase Freud.

[Aeirs]

Panties jeans and bra that I took when my mom was gone when I was 15

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[ToniB]

My sisters dresses and Panties at about 7 Years old

[Yenneffer]

Alice in wonderland costume at age 3

[Cindy]

A nappy and blanket when I was born?

can't say I remember it

[Kayleewantsout]

9 and underwear

-Kaylee

[Marlee]

I was prolly about 6 or 7 and I put on my mom's clip-on earrings.

[leatherdres5]

Thank you for reminding me.....

I used to wear mom's clip-on earrings.

[Joi]

My younger sister's dress. 8 yrs. old.

[Mado G]

At about 11, I pinched a pink kilt from my sister. I remember once wearing it while using the computer, when my dad came in suddenly, startling me. I was terrified he'd seen it, but he never said anything.

[BirlPower]

swapped panties with the daughter of a friend of my parents during a sleepover. Age 4 I think.

[Stevie]

  I think I was about 7 or 8, there was a box of my older sisters old clothes in the garage. I remember one white dress that was my favorite I was very sad when I out grew it.

[Jacqueline]

8 or 9 YO.

Tried my Mom's but moved to my sisters underwear, slips and hose. Then tried on skirts and dresses and bathing suits.

Loved it, hated myself at the time and did not quite get any of it.

Joanna

[CarlyMcx]

Scrunched and rolled my Fruit of the Loom underwear down into bikini panties when I was five.  Mom never had anything that interested me and my only sister was a lot younger than I was, so there was nothing to steal or borrow.  My first "real" crossdressing was a bikini I mail ordered when I was 20.

[Willowicious]

Mother's bra at age 3

[kittenpower]

...diapers, when I was a newborn, IIRC 

[Kerry30Den]

Pantyhose at the age of 4 or 5.  Found some in a bag and tried them on and I was hooked.   Started me down my path in life.   Fought it for years but finally accepted it around 30 and been happier since.

[gennee]

My wife's skirt-at age 56.

[janetcgtv]

When I was 7 in the 1950's while living in Chicago I was under my front porch and asked my friend if I could wear her babushka and she let me. I loved every moment of it. When older I would buy my own babushkas.

Everyone have a lovely day.
Before that when I was 3, I had put on my mothers perfume.