THE OFFICIAL: What were the first items you wore?

[Vicki OShea]

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.

[KymmieL]

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

Kymmie

[Robyn]

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.

[Toni_Lynn_P]

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

[DanielleM]

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

[StaceyWilliams]

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

[SarahMicheline]

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.

[Nena]

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

[Tammy]

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

[Rachel E.]

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

Rachel

[DorothyC]

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.

[JillAnne]

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

JillAnne

[Danielle R.]

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

[Alisa]

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.

[RaelaCross]

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.