My moms pantyhose when I was 6 or 7.
My earliest recollection of wearing anything feminine was when I was four years old. I found a nylon scrarf in a box of old clothing in the basement. It was purple in color and about eight inches wide and four feet long. I would wrap it around my body pretending that it was my underwear. The siky smooth feeling of it on my skin was very sensual and I kept this scarf hidden and wore it as often as I could especially to bed. I soon grew curious of what real girls panties would feel like and I secretly started wearing my sisters' panties. I had three sisters and they left thier clothes lying all over the place. The opportunity was there for me to start experimenting with other articles of thier clothing and as they say "the rest is history".
If I remember correctly it was one of my sister's cotton summer dress
A pair of denim short-shorts I stole at summer camp. Not a dress or anything, but they were sparkly. :P Sometimes I'd put them on at night, safely under the covers. Sometimes I'd sneak into the bathroom at night and wear them, with a small T-shirt and a bandana to cover my hair.
Did I ever get caught... welllll, one night I fell asleep after taking off the shorts and leaving them under the covers. The shorts made their way to the floor, and in the morning, one of the counselors found them! The counselors made a big stink about it, but only because they thought someone had had a girl over! I sure dodged a bullet there!
Needless to say, that ended in a hurry. Buuuuuut, on the last day, I stole another pair to take home with me.
mom,s rubber Playtex open bottom girdle and nylons, when I was age 11. I probably tried on every girdle in the house at some time or another.
My particular favorite was the Playtex Golden zipper rubber girdle --- utterly fantastic!! And I am still a Playtex girl --- my girdle of choice is an 18 Hour, preferably open bottom with stockings. And I never dress with out my girdle and stockings!!
Afyer 50+ years of dressing and wearing a girdle, I guess I'm just old-fashioned...
[SIZE=4]My girlfriends coat because I was cold and she was shocked that a "man" would even consider wearing anything that was a woman's. She just related this to me yesterday.
The first thing I bought though was fancy panties and a skirt.
Sure it was just a whim had no idea why I wanted or liked them. NOW I KNOW WHY..[/SIZE]
[SIZE=2]Ascended Ancient[/SIZE]
first for me when i was 7 or 8, pair of my mothers pantyhose which had been washed the night before hanging on the shower curtain rod. raw curiosity turned into exhiliration and they just felt good. when i was 13 i got a rare opportunity of the house completely to myself for a whole day. mom's closet got raided big time
For me, it was a pair of white leather and wood platforms with block heels (well over 5 inches) that my mother gave to my father and me to sell in a flea market (we had a spot there). I saw those shoes and knew that they HAD to be mine. I don't remember the price, but I told my father that I sold them (and of course I paid 'em), and hided the shoes for later.
This happened in 1984. To this day I still miss those shoes.
It was a gold mini skirt that i found in the back of my stepmom's closet, it also came with a top
A pair of black stockings were the first item of female attire I tried on,I've loved them ever since.
Christine
For halloween when I was age 5 I dressed up as a girl in one of my aunts red dresses. My mum was suspicious ever since
My mothers pantyhose when i was about 8
My sister's pink dress when I was 13.
My Mom's pantyhose and a slip when I was 4. I remember pretending that I was working in an office and crossing and uncrossing my legs and loving the feeling of the nylon rubbing together and the silkiness of the slip.
A pair of my mom's Candies high heeled mules when i was about 10.
I want to say that I was a full get up from my now ex girl friend
a pair of panties with cheerleader shorts...
and then later that day we cycled through a skirt a dress and some other stuff I ended up keeping those shorts though they were comfy
had the tiny kitten from looney tunes and the word Meow on the ass
One of mom's nighties....double layered nylon tricot...multicolor.
MMMMmmmmm!
I tried on one of my sisters skirts that was just lying around when I was 5
HI All:
The first was my older sister's black lacecup underwire 36B
Vassarette bra in the afternoon sunshine while home alone.
I had just walked past her bedroom and it was on the floor and I stopped and went in and picked it up.
The feel of it was wonderful in my hands, and perhaps I took off my t shirt and decided to try it on because of the previous weeks event.
A hot MILF had whispered in my ear that I should wear a bra as my tits were as big as hers.
I was a chubby self conscious 14yo and about all she didn't do is grab my nipple.
So when I took off my tshirt and slipped my arms thru the straps I was already feeling submissive.
My mother would let me watch her dress so I knew how to reach behind me and grab the ends of the band, so when I leaned forward and hooked the bra,
then nestled my little boy tits into those cups, I was changed forever into being a crossdresser.
It was incredible but that bra fit me like I had been measured for it.
In short order, I stole my sisters bra and matching pantygirdle that was also on the floor, and wore them.
Got talked to about wearing my sister's clothes and was made to promise not again.
So a week later I got into my mom's lingerie.
Can U imagine how exciting it is for a 14yo boy to be strutting in Playtex bra, pantygirdle, stockings and full slip when his mother comes in to talk to him about crossdressing.
So a week later she bought me my own lingerie and the bra was the same size as my sister's.
That is why I know what size it was.
[SIZE="4"]My mom's panties, when I was 5 years old. She made me wear them to kindergarten one day when there were none of mine clean. After that I wore them because they made me feel good. [/SIZE]
My sister put me in a dress when I was 9 or 10 and I was hooked. When I was about 11 or 12 I'd see the girls in school in their girl scout uniforms,and would race home before my sister and try hers on.Still remember all of it as if it was yesterday.