When did you first crossdress?

[veola]

12 -13 years. I liked to wear clothes and shoes older sister. I greatly enjoyed.

[Xandra]

Love your story!

[Mayo]

I tried on some of my mother's underwear and a bra when I was around the age of 10 or so (I think I said ~8 in an earlier post but I don't remember exactly) and beginning to get curious about the differences between men and women. At the time it didn't make any particular impression on me and I didn't put on female clothing again until recently, after I'd been actively questioning my gender for a year or so. However, even during my teens I was aware at some level that I had some feminine inclination, component, tendency or wish. I did realize during my pre-teen and teen years that I had a sexual interest in boys as well as girls but, that said, I realize that gender and sexual orientation are not necessarily consonant and I don't know that being bisexual is in any way related to my gender identity (which is still in flux).

[Valerie Beards]

I recall first wearing my mom's clothes when I was about 11. On school holidays and I was lying in bed thinking about what it would be like to wear a woman's clothes. This topic had been something I had been musing over for a while. I suddenly realised I could find out. Lept out of bed and into my parents bedroom. Within minutes I had put on mom's pants, bra. tights, skirt, blouse and also her panti girdle over the tights/pants. This was the late sixties and I had observed mom getting dressed and seen her wearing two pairs of pants. Curious I manoeuvred to look up others womens skirts and saw similar two panties..or as I found out a panti girdle on the top.. I must say I really liked wearing all her clothes and in particular the girdle. Still have one in my collection...47 years later. Needless to say I have never stopped since...

[lostinmyworldcd]

At 14 . My sister went off to college and left her room pretty much as it was when she was there . Hers and my bedrooms were in the very corner of the basement , away from our parents . i first started putting her pantyhose on . Then her heels . Then I had to dress in it all . I even put make-up on and polished my toes and nails as we had a bathroom on the other end of the basement . I would play dress-up all night long into the early morning hours around 5-6 am . I spent many a night prancing back and forth thur the basement , trying my best to walk sexy in heels . Although it was somewhat a rush to me , sneaking around , I enjoyed being "pretty" . I have spent the rest of my life , going back and forth , dressing up. I've bought alot of clothes and shoes , only to end up throwing them away or piling them in a burn pile . At 47 , I don't see myself stopping ......

[Midasgirl]

I had always loved the feel of silky fabric, be it the edging on a fancy blanket or the label on clothing, and around the age of 10 or 11 I began to ponder what it would feel like to be covered in such material. I remember feeling quite jealous of girls wearing satin blouses or dresses and wished I could be the one wearing such things, despite being a boy.
Given this interest, it was inevitable I'd start wearing my mother's clothes when I was alone at home.
The first thing I tried on was a white satin nightdress, an ankle length one. It was one night when my parents had gone out for a couple of hours, and I remember staring at myself in the mirror and running my hands over the silky fabric. It felt so good to be wearing something so girly.
That Christmas my mother received a pair of satin pajamas as a gift, and I wore them anytime I was alone. I absolutely loved those pjs - I'd stare at myself in the mirror and fantasise I'd been turned into a girl. It helped a lot that the pjs in question were a very girly shade of pink.
After that it was satin blouses, then satin blouses and skirts. I've no idea how my mother never realised I was borrowing her clothes so often.
Those early days were over 20 years ago, and I'm here typing this while wearing a glossy satin blouse and skirt. I'm pretty much addicted to wearing satin now
Although these days I buy my own and don't steal my mom's anymore!

[Elli87]

In pre school I'm sure Ms. Audry knew I was a fairy. Wearing woman's cloths in the dress up section, wanting to be a ballerina....playing with dolls. Now years later I look back and say ah I was just a little kid.

[MirandaAlicia]

I'm pretty sure I was maybe 5 or so, big enough that I could wear a couple of yard sale skirts (the sort with the wide elastic waistbands) as dresses. I had a collection of salvaged yard sale clothes at my grandma's house, and fostering creativity we'd roleplay fashion show and I was the runway model, and the lighting engineer, and the cameraman, and all sorts of other roles, with grandma the announcer and judge. (it amused her while she was recovering from numerous hip surgeries and was pretty much bedridden). I also had a cache of clothes at home that I actually would play dressup in with the other neighborhood girls, who didn't think it odd at all. My dad hated it though, but I think more out of the fact that my sister took such an active role in things and he disliked her treating me some of the way she did. I was so -mad- when my clothes got thrown out...

[Chancey289]

I think I was 9 when I first tried on women's clothing. I don't know why I did it, I just wanted to. It wasn't until I got older I started doing it more often and going full blown girl mode.

[Robin414]

Apparently I was fascinated by women's nylons since before I could wall so I'll say conservatively...about 2...yah I was in the 'gifted' class 😁

[Diane Smith]

In pre school I'm sure Ms. Audry knew I was a fairy. Wearing woman's cloths in the dress up section, wanting to be a ballerina....playing with dolls. Now years later I look back and say ah I was just a little kid.

I'm impressed that she tolerated it. I got a sound reprimand from a preschool teacher when I tried to handle some of the clothes and shoes in the girls' dress-up section. It was clear to me from that moment onward that wearing a dress and heels was something that boys are never allowed to do. It must have been pretty traumatic to me because I still remember it clearly over 50 years later.

- Diane

[Staci G]

I think I told the story maybe not, I was young could have been 5 6 anyway I found my sisters panties in the hamper and put them on. I went into the living room sat on my moms lap and she immediately knew. She told me I cant wear them and to go take them off. I found a bra in my moms room one day went to the boys club, must have been around 1965. There was a guy there asked my why I a m wearing a bra I don't remember my answer. Anyway I progressed to sleeping in my sisters and cousins panties and silky pajamas when I got my hands on them. My brother caught me and asked why I said I like it and he never told, never questioned any of it. He was my friend one I always counted on. He stole a full slip one time off a clothes line for me and said it should fit better than moms or my sisters. I'll never forget the first pair of pantyhose I bought myself, they were jade green and MINE!! Haven't found a pair like them since

[jaerina96]

I was around 9, don't remember how it started! Just stuff from out big box of Halloween costumes, my sister and I were pretty close in sizes then. When I hit middle school and had actual home alone time because of the bus schedule I started borrowing old dresses my mom had forgotten about and trying to look like the girls in school.. Of course I got found out and got the big lecture about hellfire and stuff after a couple years I stopped because it was super humiliating and I couldn't get away with shaving my legs without getting caught so I couldn't do it till I lived by myself after college.

[lisa_vin]

Around 3 or 4 years old with my moms nylons and slips.

[Melanie 0339]

I was about 13/14 we had a spare room which was full of alsorts while I was being a nosey teenager I found a suitcase which was full of old clothes inside was a pair of stockings and a suspender belt. I'd seen girls in certain magazines wearing these before and I liked what I saw so I thought I'd try them on to see if wearing them would create the same feeling as seeing girls wear them, and omg it was better then I could have imagined they felt amazing on my legs and the straps rubbing against my thighs as I walked around in them since that day stockings and suspenders are still my favourite item of female clothing and it's very rare for me to dress without them xxx

[Jane G]

Tricky one. I used to dream a lot about being a girl from a very early age but I don't recall dressing up until I was 6 or 7.

[SillyGirl]

Probably 9 or 10 the first time I tried anything on, I remember really becoming enamored with girl's clothes around 12 or so. That was when stirrup pants were a big thing and my step-sister came to visit her dad for a month in the summer. I was constantly sneaking into her stuff and wearing her panties, stirrup pants, anything else I could get my hands on. I initially just wanted to know how the stuff felt but then I liked the way it made me look and feel and it escalated from there.

GG's don't realize how good they have it. One of the things about them I'm most jealous of is how with a change of clothes, hair style, makeup and accessories, they can look like a completely different person. The conservative business woman turns into the night club sex pot in under an hour, etc. Dressed as a guy, that's pretty much impossible to accomplish.

[Chloe1955]

I think I was about 11 or 12 when I used to sneak into my older sisters room and fondle her taffeta half sips, I used to take them into the bathroom and slip into them it felt awesome. My mom was a sewing machinist and used to alter/make clothes for friends and she made an amazing silky dress for a friends daughter and hung it up on the back of the lounge door. When my parents went out I tried it on I adored the tactile feeling against my skin it was out of this world

[melb24male]

I remember when i was around 10 years old, I tried on my mothers Blue one piece bathing suit. I remember instantly getting hard. As i watched my **** push against the Bathing suit. Was hooked ever since

[Jennie2]

How could I not remember something so life changing.
I was about 7, age doesn't matter, It was a small light blue full satin slip, I just had to try it on, it felt so right, I was hooked. Now I am just about to slip into a light blue cotton nightie and white cotton panties, feels so good to sleep en femme.

[QueenShorty]

Was about 7 or 8 when I first tried on my mother's high heels. I wasn't really interested in clothing until my teens. Around 17 was the first time I tried on lingerie. My mother had a box of unused lingerie (her and her friends used to sell them) that sat in the closet for years. I've been hooked ever since I put on that silk camisole .

[Kaze_]

I remember my mother caught me with her panty hose when I was like ~5 actually. One of my first memories is from around that time. It was asking for one of my mothers dresses and getting shot don't pretty harshly. >_>

Dunno why I crossdress but its something that's been with me from the start.

[Sandra119]

I remember wearing my mums underwear when I was about 9 or 10

[Sexy_Stephanie]

When I was like ten I tried on my sisters skirt

[vicky77]

when I was 6 one I was in my sister's room, I saw a summer dress of her and I tried on...I still remember the scene.