I don't remember exactly which item it was but my dressing started when I was younger and a friend and I used to try on his sister's dresses and see who was the prettiest.
Now the dresses are mine, but I still want to be the prettiest!
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I don't remember exactly which item it was but my dressing started when I was younger and a friend and I used to try on his sister's dresses and see who was the prettiest.
Now the dresses are mine, but I still want to be the prettiest!
My first I can remember was nylon panties at grandmas when I was sick and had no underwear. Later when I wanted to, it was yellow nylon pettipants.
The first really serious thing I tried on was stockings and garters together with my GF ages ago... After that I have been really hooked!
For me I was first maybe like 6, I found some of my moms panty hose in the bathroom so I tried it on, my mom caught me, but just though it was funny. Then at about 7 or 8 I was in a school Christmas play and I was an elf and I needed green tights, I thought those things were awesome at the time. Then I stopped for a while and when I was about 13, my family was out and I don't know why but I thought I wanted to try more, so I went to my sisters room and put on a skirt and lacy shirt. It's advanced from there but not to a make up and wig level.
My sisters' dresses. My three sisters lived just down the hall, and I would borrow from their closet when they weren't around. Had to be very careful to get them precisely back in place.
I was a kid, like 8 or 10? Can't remember, at all.
Age 4, tried on one of my mothers griddles, of course it was to big. My father caught me and and I was spanked. Needless to say that did not stop me. I have always felt more comfortable with feminine things.
My mother used to hang her white Playtex bras, girdles, panties and stockings in the room where our shower was. Needlless to say, the attraction was too strong. The bras and girdles were the most tempting though in my pre-teens, I didn't know that much about it all! I still have a strong feeling for those white, lacey Playtex products. I buy them when I can.
I can't remember the very first thing, probably my sisters panties, however; I do remember clearly going to a fancy dress party in my 1st year of high school dressed in a shimmering blue cocktail dress, fishnets, heels, full length gloves and..... a Miss Piggy mask! The mask was my sisters, it seemed like an easy costume to make, and I remember getting quite excited seeing myself (sans mask) in the mirror. I've since come to realise that I was extremely lucky to get away with it without being mercilessly teased by my fellow students, no wonder I'm still in touch with most of them 20+ years later.
my sister's dress when I was 4
GOLD!!! The signature is a classic too.Quote:
Originally Posted by NathalieX66
My friends wanted me to be princess daisy for our dressup game so I put on the lovely pink dress and the lovely wig and I was hooked from then on
My three year older sister's laddered stockings and tattered garterbelt that I salvaged from the rubbish I was detailed to take out. I was ten years old. I still remember the wonderful feeling of the stiockings on my legs, and the four straps passing over my thighs.
Mom's bra and girdle, later her nursing uniform. I was nine and it felt so wonderful.
My sisters shoes, I would wait for her to leave for school and sneak into her room and try them on. sometimes I would sneak a pair into my room for later and then sneak them back to her closet the next morning.
When I started crossdressing bloomers were still in style.
It think it was shoes and a dress.At age 12 or 13.:hugs:
Angie
my mother inlaws dress. I was so stoked I fit into it.
After being attracted to hosed legs as a child, it was only natural for me to rummage through my mother's hose drawer and eventually try on some nylons. The thrill was intense, but not nearly as intense as the time I decided to venture downtown (as a 13 or 14 year old) with pantyhose under my jeans. I figured EVERYONE on the bus knew my secret.
Now, decades later, I still wear pantyhose under my jeans almost every day.
My mother's open-bottom girdle (like in Pan Am), found in the airing cupboard, when I was nearly 10.
It was a pair of pantyhose that I "borrowed" from my mother. I believe I was maybe 10 at the time.
Over 50 years ago and I still remember......
My cousin's yellow full brief panties. Why did I ever, what EVER possessed me to look into that drawer of her chest?
Funny btw..... in 1970 something while staying at my sister-in-law's trailer while she was out of town, so nobody would rob it...( yes you read that right-- like who would want to rob a trailer?), I found under the mattress a red one piece pull over red lace and nylon bra. I thought it was a pair of crotchless panties. I know better now. lol.
mommy's panties, mommy's panties
Mother's high heels when I was extremely young. She caught me a few times and thought it was funny at first. She had to hide them from me later lol
probably some of my mom's pantyhose and high heels!
This is my favorite thread. Who can forget that first time donning women's clothing? I at once felt that I was taking on a part of the awe and mystery and wonder and beauty of woman. It has been a source of great joy and comfort ever since.
A pair of pantyhose.
I was eight years old and it was a full slip and stockings. Amazing.
I'm not sure this counts but I can remember being dressed up by my friends older sister as a girl when I was 11. The first time I did it on my own was at 15 when I tried on my mothers panties and bra. It was all down hill from there lol
A pretty pair of white panties with blue flowers all over them.
my first pair panties from sister in law she didnt know. I loved it .
My wifes satin string bikinis. I still remember that day VIVIDLY.
it was my moms bikinis that i first tried on when i began.Quote:
Originally Posted by cindi cinnamon
Started out putting on my moms pantyhose. It didn't take long before I was into my sisters panty drawer. Now I fully dress and buy my own clothes.
Pantyhose at around 2-3 years old.
Well I'll give two different times. The first was when I was 8 and my dad forcibly put my sister's red dress on me. I protested on the outside but inwardly I loved every moment. The first article I chose was my mom's white accordion pleated skirt when I was about 12.
I tried on a bra. I was 5 playing dress up with my siblings and my brother dared me to try on my mothers bra. I did. I liked it but didn't say anything about it. Eventually I dressed completely and I still do.
I use to take my sis stuff and wear it. i was about 10 at the time and bought 14ish when i bought my first pair of tights
Pair of butterfly panties and some grey tights
Started at 11 with moms bra and panties but don't know where it's going to go From here.
Makes me so sad reading this thread and how young most of you were the first time. I have missed out on so much by repressing my fem side. First time for me was at a friends party on my early 20s, where I was encouraged to put on my friends, sisters prom dress. I played along that it was just a joke, but inside I loved every moment of wearing that silky blue gown.
Charlotte
I was sitting in church one morning when I was 12 or 13 and I seen all of the women wearing pantyhose, I don't know why but I decided I wanted to know what they felt like. I had alot of alone time growing up so I borrowed my mom's pantyhose and the rest is history. Looking back my mother knew about my dressing, things like she kept a pretty blue pair of panties in her draw that always caught my attention. Looking back they were too small for her, and she stored other clothes in my closet because she needed more room but several of the dresses were my size.
One of my mother's gender-colored bras a log with a set of gender flavored tights. Sara almost got caught as well, but not in that decade.
A Short skirt from my grandma!!!
Panties early 1960s.
I remember it well. The first thing I tried on was my foster sisters panties. I was later caught by my foster mother and made to dress as a girl for a couple days as punishment.
My sisters pink panties and haven't looked back since...pink for me xoxo
I believe I was about 12 yrs old just playing dress up in my dad hat and vest you know watching gangster movies and Roy Rodger's falling of there horse and fighting rolling on the ground. Well one day for what ever reason I found a bag of old clothes that some one had thrown out and I found a Nurse uniform in there and but it on well let me tell you how wonderful I felt just the fell of it on my body made me so horny I didn't want to take it of. Now I still love to be all dressed up
I believe it was pantyhose. I was around 12 or 13.
A long black nightie that my mom threw out and a french maid costume.