first article of women's clothing that u tried on

I am sure it was a half slip after I dried off after a shower, they were always in the the bathroom drying, but pantyhose was the 1st item I wore longer than a "Cheap Thrill Moment".

nothing cheap about those moments that tranfix a mind to a life long quest!

I think the first thing I tried was panties, and then a bra. I went on to girdles after that, and actually had a couple of them stashed away for when I thought I could get away with wearing them under normal clothes. It felt REALLY risky, as where I grew up was a small place, and if you were found out, you would have been the laughing stock. They were a bunch of straightlaced people.

I never much did the pantyhose or hose at all. I used to hear my mom say how pantyhose were expensive, and were so easy to run. At the time, I think they were pretty new items, and I remember the garter belts and normal stockings for a lot longer. I didn't mess with them much either due to the run issues and the "expense."

So I stayed pretty much with stuff that wasn't easily messed up - or so I thought. The first time I wore the girdle out of the house, I ended up not being able to go and change pror to having to do some family chores. I had to mow two large yards with it on, and it was more than a little bit warm outside. It was a great feeling, but I was TERRIFIED of my parents noticing it under my clothes. I think I was about ten at the time.

As time went on, that one became my favorite article to wear. Turns out it didn't seem to be as noticeable as I may have thought.

I am Erica2

I went with an entire outfit the first time. A friend made me over with her clothes and makeup in high school after she noticed we were the same size. Other than squeezing my foot into her shoes and having to buy my own undies it was great. So I kept doing it. :) And here I am!

my sisters bra panties garter belt and stockings she wanted to see me dressed.

my mother still has a great figure at 50 but back then her legs were amazing..veary meatu and full.looked great in pantyhose and miniskirt.so it was vedy natural to me to try to emulate that look, so the first pieces I tried on where a tanned pair of pantyhose followed by a purple miniskirt it felt awesome

I was initiated by way of a pair of sexy panties! White lace! Fireworks went off!!! It was love at first sight!!! LMAO!!!

My first piece of clothing was when I about 5 years old, when I went into my sisters closet and tired on her one piece swimsuit and also tried on one of her dresses I recall it was a blue one...
It felt accelerating!! =) Until I got caught! lol

i think i was in like 1st or 2nd grade and there were pantyhose drying on a rack in the bathroom... i locked myself in there and tried them on... several times... i loved how they felt...i remember there was a girl in like 2nd grade on the playground wearing tighs or pantyhose and i did everything in my power to try to touch her legs lol :-)

My sisters panties from the dirty clothes hamper worn over my head and situated just-so where the sweet part alligned with my mouth and nose - but that was for arrousal when after experiencing the real life 1st time random whiff of the amazing scent of a woman I quickly became addicted and wanted more and more... so it probly doesnt count :P

So I'd have to say my moms bra, filled with tons of tissue 'cause she was soo well endowed and sexy as all get out ;)

It would have to be my Mom's slip when I was a pre-teen. Life was simple back then...she used to leave her slips and bras and girdles hanging in the bathroom. But it wasn't until I got older and started babysitting in my early teens that I really started.....while watching my young cousins it was my aunt's clothes once the little ones went to bed.....and then my best friends older sister's matching bra and panties....it was so nice to see something other than just white.....

I would have to say rather than a first article of clothing I had a first ensemble of clothing.

One Saturday night when I was nine years old I gave in to temptation and decided to finally find out what it was like to dress as a girl. Luckily I had a well dressed sister two and a half years older than me. I went into my sisters room and got a little green skirt I had always liked. Taking it to my room, I removed all my boy clothes and pulled on the skirt.
I knew I would like it. I had been wanting to do this for years. But I could hardly believe how breathless I felt. I skipped down the stairs wanting to experience the feel of the skirt on my legs. I then sat down carefully smoothing out my skirt, finally performing this simple act I had forever wanted to imitate.
I was then overcome with the irresistible desire to dress completely. I knew that the next day I would have the house to myself for many hours. So I decided to put the skirt back and wait for tomorrow.
So the next day I grabbed the same skirt, and a matching green sweater from my sister's closet. I then went to my mother's room and got underwear. I had watched my mom put on pantyhose many times and always wondered what they would feel like to wear. I was now finally going to find out. As I pulled them up over my thighs and around my waist I remember enjoying it more than I had imagined was possible. The same thing occurred as I put on her padded bra and fastened the hooks in back. Luckily for me my mother wore fully padded bras which provided me with the perfect profile. Next was the skirt followed by the green cashmere sweater.

My Mothers corset and slip It felt so great wish I had a corset now

I started with my Mother's Hanes RHT nylon stockings. I loved the sleek feel of them on my boy's legs and how smooth they made my legs look. I was delighted that her high heels fit my feet perfectly back then and enjoyed many fashion shows with her clothes when home "sick" from school..

I was probably one of the sickest kids in grade school, but not quite so sick I couldnt be left home alone while mom worked.

Cough cough sniff sniff I dont feel so good.

The very first pair of female clothes i tried on was a pair of nude pantyhose and i was 6 years old.

Pantyhose, when I was really little. I loved it <3

My mothers nylon stockings.

The first time for me was while playing doctor with a neighborhood girlfriend. She had laced nylon panties and a training bra that fit me so well that I asked her if she would give me some of her clothes to dress up in. My lifetime passion began at that moment.

Wow the first article woul dbe my sisters bra and panties and quickly progressed to her skirts and tops. I always dug in the hamper for those bra and panties first. the natural scent of a woman was even more for effect when I was arround 12 or 13.

The first thing i wore was a pair of size five white cotton Hane her way panties. They were so comfortable they helped me decided to wear panties 24/7

For me, it was also Mom's bra! I used tennis balls for breastforms, put on a tight T shirt and thought how great I looked. LOL

I was 5 yrs. old. I was helping sort the dryed laundry and had for my moms kneehi's ask what are these and then just put them on. the felt great. It didn't take long to look for them again and found pantyhose. My mom kept a bag of old pantyhose in a closet right across from the bathroom I raided all the time. The of course the silky slips and panites that hung to dry in the bathroom I tryed on next. Everything was big but I grew into her tuff between 10-13 yrs old. When I 12-18 yrs old and left at home alone I wore her clothes that I could fit into.

My moms bra, probably when I was 10 or 11. She had padded bra's. I remember it felt great, no - amazing!

A pair of my mother's pantyhose with some runs that she had just gotten rid of, when I was about 8. I don't I'll ever quit wearing pantyhose, even secretly under my pants.

my aunts panty hose, and bra.

I was 15 and my gf at the time somehow managed to get me 1/2 into one of her bras when we were playing around in her room. First time I actually wore something was later that year @ halloween. A bunch of us did a gender-swap thing, I wore a black tank and a pink skirt.

My Mom's girdle and slip then bra. loved the smell and soft yet tight feel. haven't looked back since.

My first posting so what better than to tell of my first dressing experience?

I was about 6 or 7 and was playing in the lounge after a bath and for some reason put on a pair of my mother's sheer tights (pantyhose). I can still remember tthe thrill! I then put on another pair over the first and proceeded to prance around like a ballet dancer in an attempt to justify wearing them. My mother was fine about it and I sat in those tighhts for the rest of the evening till bed time, when I had to take them off... :(

Soon after that I was sneaking the occaisional pair of tights and then panties and girdles and slips until I hit my teenage years when it all spiralled and I had to have my own stuff. Unfortunately, when my stash was subsequently found, it was not as welcome as my initial 'playtime' dress-up...

Only child with a mother who was a real estate broker and father who was a pilot I had no shortage of alone time or privacy and started at eight with her wigs and makeup. looking in the mirror for the first time with the wig on was the first time I felt my reflection match my sense of self and the mold was set. By thirteen I was the same size as my mother who favored Ann Taylor, still one of my favorites for shopping. She had closets full of clothes and never noticed.

My mom's pantyhose....I was 13 then!

Sisters bathing suit. It was white with a strapless top and had a wood ring in the center of the top. Very Sexy! :)

The first piece of female attire I wore was my moms green floral dress, which I now find interesting since most of you who have posted started out with some form of underwear.

My mother's full slip. White with white lace trim on the hem and bodice

I had it good with my mom's stuff; she worked in the lingerie department of a large department store. She had all kinds of wonderful full slips, half slips, girdles and stockings. Mine was one of her full slips under one of her dresses.
I wish I still had the lingerie she had over the years. I would be the proprietor of a nice little vintage lingerie shop on eBay!

Nylons and I felt something right away

When I was 13, already had breasts so it was natural to try on my moms fredricks of hollywood bras she put up in the closet next to my bedroom when she got too big to wear them.
The feeling of being contoured was an instant hook for me!

Pantyhose and skirt at 13. It was the best feeling ever.

Hmm. I don't really recall the age. And it's hard because I've been doing it since I was very, very young. Even as a small kid in kindergarden, I'd go into my mom's bedroom and wear one of her dresses. I was eventually caught but didn't stop. Throughout the years, its gone from my mom to my sister's dresses and things, to my friend's parents to eventually my step mom's wardrobe until I moved out on my own. I ignored that part of me for years, as I had many roommates who don't share my open mindedness about things until one day, I was shopping for something or other on some sight, came across a silk chemise and ordered that, some panties and a bra. My grandmother, bless her heart, let me use her credit card and only asked once what i needed them for. I gave some silly excuse that I know she didn't buy but a few months after, died of cancer. I like think she knew why. So, I mean, as a kid, my very first time? I think it was my mom's white silk dress. But as an actually crossdresser, something special that was given to me by the first woman who knew and accepted me. =3

The very first item I tried on, was a lacy half slip of my mothers. (I was about 5).

The very first item I bought, was a Pink Garter Panty, followed by stockings. (I was 10). They Felt Wonderful!

my sisters mini skirts when i was little,things in my hair, whatever makeup i could pilfer, and my sisters heels

Several thousand years ago, and (very literally) in another life... In other words, when I was about 7ish... I think; I tried putting on my sister's make up. Sister made fun of me, parents thought I was weird, so I ignored it. Then, about only a few hundred years ago (and still in that previous life), home alone after school, couldn't resist trying on my sister's skirt and matching... Uh.. .Blouse? thingy... that went with it.

Got to be OBG with Tan stockings my mothers and white bra

a full on japanese school girl outfit my girlfriend at the time bought me for halloween

My sisters makeup! and a silk scarf. Oh my god - seems like 100 years ago!

When I was young (about 4 or 5) I had a baby sitter that would dress me as a little girl then we played house. The first thing I tried on my own wad my moms panties and bra when I was about 9 or 10

the first thing that I wore was one of my moms sports bras unmolded and several camis. I wish that I kept some of them.

I was dressed as a girl upto the age of 5. On my own, i strated with wife's panties and camisole

My Aunt's panties and bra. So HOT

If I remember right it was a pair of my mom's panties when I was a teen.