What was the first item you wore?

First, some fifty years ago, was a black full slip with a lace trim. Still am collecting slips.

The very first thing was one of my mom's bras worn over top of my t-shirt. It felt so wrong I had to take it off right away.

Then I removed the shirt and tried again. Much better. :)

For me it was pantyhose back in elementry school. Thats how dressing started for me. I loved pantyhose so much sometimes i would wear 3 pairs at once.

This is kind of silly but I remember it like it was yesterday, even though I was probably 4 or 5. My mother was sewing a fabric cover for a large lampshade with a tropical pattern popular in the late 50s. It looked like a skirt and I just stepped into it and admired myself in the mirror.

Years later, it was her panties, slips, stockings and pantyhose until I outgrew them and gathered my own stash.

As the youngest of three boys, she often told me I was supposed to be a girl. I'm pretty sure that had a huge effect on me and my desire to dress.

For me it was my mothers pantyhose that started me with the whole dressing experience. From that it lead to wearing her bras, panties and slips it wasnt til later on when i started to dress wearing her dresses and heels.

Mom's pantyhose, mom's pantyhose, mom's pantyhose. Did I also mention mom's pantyhose? Got caught, she hid them from me then. The other items didn't happen until the early teens with my sister's stuff. Quite a surprise I got then when I understood just how much I enjoyed it.... Ah, to be 13 again... not!

Ginger

I was 14. Actually went out to the local Federated department store and bought a padded white bra in 36C. About the biggest they had. Talk about nervous. I think I developed pimples, needed glasses, and got dandruff on that very same day.

So after 50 years of being pretty straight, I couldn't resist a pair of panties at JC Penney's and look at me now. LOL

Just realized that I'd already posted to this thread. Oh well, this one's funnier. I hope.

A chastity belt. :battingeyelashes:

My moms heels.Never forget it.Probably about 4 years old.Next was a blouse of hers..

Mom's panties. She left them hanging on the hook on the inside of the bathroom door. I was 10. Then a pretty petticoat and Playtex rubber girdle. But panties came first! Great tactile memories!! I remember they were old and kind of raggy. Poor Mom.

Love,
Stephanie

For me it was probably my mums stuff. But one of the clearest memories I have is my Grandmother talking me into entering a fancy dress competition at her local church. She and my mum dressed me in faded, frayed jeans a bright sweater and a long wig to try and make my look like a "hippy" (this was in the 70's). I was there waiting for the judging when I got talking to two other girls about 11 or 12. One of them said to me "have you started your periods yet" and I realised they thought I was a gg! Never been able to pass since though and don't suppose I ever will!:doh:

I was 4 or 5 and visiting at my aunt's home with my mom. I had gotten very muddy playing outside and they put me in a pair of my aunt's panties. Why they didn't grab a pair of my uncle's briefs I don't know?

geeze girls

rdy to read my dark history? My closet is full of Black lights and fishnets. ive read so many posts in my short time here revealing secret lives of people like my self i feel so inclined to share mine

My earliest memory:

I dont remember my age but i was in 2nd or 3rd grade,
my mom who i only lived with during summers and school breaks often got HUGE bags of used clothing from other families as we were poor and needed help in any way we could get. Clothes were a luxury to us in any form used or new.
There were bags of clothes of all sizes in our garage, and i was drawn to a black dress that i had to tie the spaghetti straps to wear as it was way too big for me.....

My first fashion show:
Around the same time i had another boy friend stay the night on the weekend, being silly kids we went thru the clothes in the garage and tried on the girls clothes, we then decided to have a fashion show for my mom and sisters who were very much younger than me. only to be stopped halfway thru by my mom who was now that im looking back was generally embarrased for us. but did nothing to repremand us on the pretense that we were just kids (my genetic mom is truly a saint)

My first admitance:

Many years later, i was in highschool. i was into industrial and gothic music and met a girl who changed my opinion about myself and showed me that my "urge to dress" was accepted in some way by a underground culture. i met at her house one night before a concert she dressed me and did my makeup. We saw Nine Inch Nails, Danzig and Marylin manson at club five in jacksonville FL. and it was my first outing to a concert in Female attire. I wore fishnets stalkings backwards over my shoulders and crotchless fishnets under my black jeans
in a trashy fashion with gothy guy make up. I was hooked...my GF knew it

Then came a long time of denial....very dark...i spent what seemed an eternity unhappy with who i was

My fondest memory:

Then i met this beautiful girl..fell in love..a year later i told her about my CD ways, she giggled and said "whatever, its just clothes". A year later i asked her to marry me, we have 2 kids
and a great relationship despite the ups and downs of my purging and acceptance of Cding. The first time i was dressed in front of her i wore thigh his and a garter belt.

Well the rest is history

Thanks for letting me share

-Donni-

I believe the first thing i ever wore was a pair of pantyhose back when i was 8ish (i think). it was merely a curiosity thing at the time, but since then, its gone way beyond :)

Earliest memories are of wearing my mom's stockings when I was alone at home. That first experience seemed to sear my brain.

Later, in high school, I worked at a drug store. They kept the broken and open packages in the store room. I could help myself to nylons whenver I wanted. Talk about feeding an addiction!

Heidi

My mother's high-heeled shoes and Skirts. :heehee: :heehee: :heehee:

Spring of 3rd grade I discovered my older (4 yrs older) sister's silky panties and my first recalled erection. I would sneak into the laundry or her room and try them on whenever I could. I stopped for a good 3-4 years when I discovered my oldest (11 yrs older) sister's very sexy, silky an shear panties, thongs, bras and lingerie. I now buy my own, but my curiosity in my sisters' underwear was what got me started.

I remember seeing my mom and sister walking around in pantyhose and I took a pair of my sisters from the bathroom and had put them on and that was it...I was never the same after that!! Later when I was in my 20's and living with a girl was I able to try more things and realized just how much I loved thier feel ect...it never fails to get me down deep.

My mom's pantyhose when I was 11. I didn't even know what crossdressing was at the time. :)

The first thing i ever wore were some a small white and blue thong.

My sister's panties then bra then skirts and blouses then she noticed her laundry kept getting smaller and smaller and asked me and helped me buy my own stuff ever since

It was a pink skirt, the kind of style with the poodle on the corner. We put on a 45 record and danced around the room in our skirts and socks.

Tights were the first thing i wore.....now its entire out fits

A mini-skirt and crop top with boots from my sister, I still remember this from close to 50 years ago. Funny thing, I am wearing a crop top tonight and wore a crop top and mini skirt on Saturday night out partying.

Black and white babydoll dress when I was in 7th grade.