Crossdressers-Haven.com

This one got me thinking. I had some play jewelry and a purse when I was really young, like 2 years old. I was dressed up in a couple of costumes before the age of 5 that involved tights. The earliest thing I remember trying on on my own was my mother's nylon panties around 7 or 8.

Just like many of us. My first item was my sisters panties. I was 13 or so. Cannot remember

Kymmie

All the girls in school got to wear the cute shoes… oh how badly I wanted to wear pretty little shoes. Having two sisters and a mom, of course I’d get into their closets and try on their shoes. I remember carefully sneaking out one pair at a time and putting them in my room so I could wear them at night in private. Silly, but sometimes I actually slept with them on because it was the only chance I got to wear them for more than a few minutes. I’d hold on to a pair of shoes for a day or two, then I’d carefully put them back and select a different pair to wear next.

I think it may have been my aunt's pantyhose or my sister's panties.

Shortly thereafter it would have been my mum's bra.

And then after that my cousin's swimsuit

BUT -- none of those were satisfactory. I had to have my own, so by age thirteen, I was buyng my very own panties and a training bra. And it was then, in wearing them, that I felt complete. (BTW - -I simply CAN'T be the only boy who wore a training bra!)

See the post 'Small Beginnings' for more detail

Hugs

Toni-Lynn

Best I can remember, I was about 14 years old, my sisters bra and panties. Just hitting puberty, you can imagine what happened! It has been a roller coaster ever since.
Dan

The first article do clothing I wore was my sister's pink dress when I was 6 ... Wanted to know why my sister liked wearing! This started my cross-dressing journey

The very first thing item that I remember was playing with the girl from the opposite house when I was 5 or 6 and borrowing her spare tutu so that we could play dancers – I even now remember the great feelings I had wearing it. It was the some years later that I wore my mum's tights and skirt.

My moms red satin dress and her black knee high stiletto leather boots.

My first memory was my mom dressing me in diapers, rubber pants and a sundress, I was 8 at the time

My sister's bra @ 12 years old. I don't really know why I did it. I do know that I liked it.

Rachel

My first item I ever wore was a pantie girdle of my mother's. I was 5 years old at the time. I was a big kid, but I had to hold it up as it was way too big for me at the time. I remember the shiny satin panel in the front and the lace around the cuff of the legs. I was instantly hooked and it started a lifelong passion for Cross-Dressing and Lingerie.

My moms pantyhose and underwear when I was 7.
Also wore my sisters bathing suits at 12.
Haven't stopped since.

JillAnne

My mom's panty hose I still remember slipping them on I was 4 or 5 years old, the feeling was incredible. Girls have all the fun

Pantyhose... my mother actually modeled pantyhose for a stocking manufacturer and there were always a bunch around the house. I think it must have been late 60's or early 70's and mini skirts were in fashion, so the full slip I added next was really short. I did not know any better at the time so I think I put nylon panties on over the pantyhose. I must have been 10 or 11 years old.

my mom and my aunt would dress me in girls clothing because i was such a pretty little boy. i was very fair skinned, big brown eyes (still) and platinum blonde hair. I would also be in the room as they dressed or undressed and i remember playing with bras and all sorts of lingerie. i loved the look of my aunt naked, not in the man sense, but in the sense that i identified with that. As i grew older, i discovered that i loved makeup, perfume, and especially women's clothing and underwear. i remember wearing girls underwear in the 5th grade at Catholic school. i've loved dressing pretty much all of my life.