At 6 I would take my sister's underclothes and her dresses as I grew I'd take more bras panty hose,

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I was about 9 yrs old, I had some alone time, I put on my mom's girdle and stockings she had just taken off after work
I felt so girly and nice.. I was confused as to why but  well we all know the story

My mom's shiny white 80s-tastic dress age 9ish. My mom was the only woman in the household and her fashion was kind of depressing but I'll never forget that white dress with hip flares and shoulder pads.

Clothing didn't matter too much to me when I was young. When and where I grew up, many of the girls wore the same shirt and jeans as the boys and most rolled up the bottom of the shirt and tied it at the waist so that's what I did too. It wasn't until my early teens that I started buying female-specific clothes. The "Uni-sex" fade came at just the right time for me LOL!

Hmmm.

I was about 12-13, and I wore a top, and black tights with heels. I do remember trying on one of my sisters' bras.

At 7, A red dress of my cousin. When I visited my uncle's house. After taking bath, I didn't have any clothes to wear, so my cousin gave me this dress 

Towels, blankets, and whatever early on. At about 9 I found a pretty fabulous high waisted two piece bathing suit from the fifties. Yellow with white fishnet over it. So sad when I outgrew it. Vintage style has always been my favorite.

11 years. My mothers Bra, slip, skirt and pantyhose plus lipstick. My mother was the only girl in our house of 6. I had only fleeting moments to do this.

my mom wanted her firstborn to be a girl so she went and bought girl clothes and when i was born a month early and was a boy she had no boy clothes so she dressed me as a girl til my dad put a stop to it when i was 3. what i was thankful for was gender neutral clothing til i was 13 and started to get into my middle sis underthings,then at 17 started to wear my moms dresses when i was home alone..

Mom's one piece panty /bra /girdle combo, age 9.
Then anything (of mom's) I could get my hands on     
Don't know why, though I'd gone crazy, ashamed, inbarested, but just couldn't stop.

I really don't recall the first item. It was over 50 years ago and it was my sister's clothing. To be honest I've been wearing women's clothes since as long as I can remember 😌😌.
Ciara.

panites i was about age 5

I think I was around ten or eleven and snuck into my older sisters room and tried on one of her dresses and looked at myself in the mirror and twirled around modeling in front of the mirror, it wasn't a sexual high at the time but once I discovered her underwear drawer that totally changed and I got very aroused by slipping on a pair of her panties. I thought they were the most comfortable article of clothing ever and I still do. I always got jealous that girls had such amazing underwear.

Went into the airing cupboard to pull out my sister's knickers. Put them on and had such a buzz.

I was 4.

This dress, at 46.

My mother's underwear, age 12.

Nylons...  I have three amazing nylon memories.... first time I felt them on a girl friend, first time I tried them on, and the first time I had enough courage to buy some for myself.

My cousins party dress that she should have been wearing, instead I was much to countenance of all the adults. Don't remember how it happened had to have been about 6 or 7

Women's underwear. Age 19

I can remember trying on some of my "great-aunt's" underwear when I was about 10.  It is still so clear in my mind that it could have been yesterday.  My gender dysphoria had already been triggered a couple of yrs. earlier.  This would have been in the mid '50's and my great aunt was already old (to me) by then, probably in her mid 50's.  I found the underwear stored in an old trunk in her attic. What was great about it was that they were so pretty and were pantelettes (mid thigh fitting.)  She would have worn them when she was in her late teens or early 20's.  That would have been in the "Roaring 20's."  Sure wish I had them now!