When did you first crossdress?

I can remember wanted to from a very early age. But the first time I was probably around 8 when I put on my sisters Guess jeans.

I'm new here, but I couldn't resist answering this thread!

I remember being 10, playing dress-up with my sister and finding an old Halloween costume, some girly pink fairy dress. I put it on just for fun, but when I went to take it off, I caught myself in the mirror and couldn't stop staring. It felt so wrong, but in a way that gave me a crazy rush.

I filed that desire away and didn't think much of it. Then a year or so later, I saw the movie "Ladybugs" on TV. It's about a boy who has to dress like a girl to play on a girls soccer team. In one scene, he has to learn how to act more lady-like, so he's taken to a dress store. He ends up in a white flowery dress with lace trim and a little rose on the front, with a blonde wig with bangs that made him look just like all the girls I had crushes on in middle school. I taped the scene off TV and watched it over and over- I wanted to be him so bad! From then on, I was hooked on dresses- the more flowery the better!

13 tried on a cousins tights,leotard and knee high heeled boots.was going to be a cat for halloween

Nail polish about 5, clothes mmm 8 or so. I still remember pretty vividly putting on nail polish too!

I was you very young 6 or 7 so i really had no idea. But its in some of us. I like been a guy but I also like been girly.

I remember being 4 or 5 and trying on my aunt's stockings that were hanging in the bathroom. I always felt she knew what I was up to in there. I have been hooked ever since

Very early. I must have been like 3 or 4 when my mom asked me to wear my sister's panties since my underwear was all being washed. I must have liked it. The other vague memory is me at about 5 or so wearing a frilly dress from my sister and being caught in it. I don't recall what happened but i was hooked. Ever since then i would wear my sister's skirts in the bathroom and i'd put on pants over them to go to my room. With the benefit of hindsight i believe my parents must have suspected, but said nothing...

i think i was 5 when i put on some clothes of my mother. the blouse was much too large and i had to use a belt for the skirt :)

I started when i was six i used to put om my sisters panties. at 8 my step dad made me dress in all my sisters clothes and sat me on the front porch so everyone could see me.i was hooked for life

I think I wss about 8 when I tried om my Mum's swimming costume. The thing is, I don't know what drove me to want to try it on. It just felt really nice.

I have been wearing womens clothes as far back as a child can remember

When I was about 7 or 8 my mom accidentally washed a pair of my tighty whiteys with a red shirt and they came out pink. She put them back in my drawer and said I didn't have to wear them if I didn't want to. I remember frequently wearing them under another pair just because I loved the look of the pink. I learned how to do my own laundry from this, too :)

From there I waited until puberty and began trying on her undies and even some of my sister's when I was able. Now I don't even own any men's undies (except for a few really high priced pairs from Prevail I purchased years ago before realizing panties were the way to go).

I was 12 wen I first tried dressing up. Was at my aunts house nd noticed sum lingerie she had nd sum thigh stockings. So I took them hm with me nd later on that night I tried it on n mmmmm fell in love with it.

Hi there...

I began when I was about 10 years old. I didn't think twice about doing it. My mother was out all day and I did the proverbial closet raid. I was able to fit in everything quite well...a blouse, panties, tights, heels. The big challenge was putting everything right back where it belonged. Quite frankly, I believe she had her suspicions but it was never discussed.

Anyway, for a months after that, I continued. One great resource I had was the laundry room in our apartment building. There always seemed to be some dresses and stockings that were left behind. We had a neighbor who would ask me to cat sit for her while she would go to work, etc. I would have my little stash of clothes in a bag and dress in her apartment and just hang out.

I have thought about it for a long time, but only got the courage to actually do it after I retired from work.. I just started the first of last month at age 67. I have a lot of catching up to do. I really feel like it will be a great ride!

Like many others, about seven or eight years old, although I know I wanted to long before that--I used to wait for new department store mail order catalogues with incredible anticipation (Eatons, Sears and Woodwards here in Canada)...I would gaze at the lingerie photos with so much longing and curiousity! Finally, I gathered the courage to explore my mom's dresser, and I vividly remember trying on her Vanity Fair full panties and a slip. I was in heaven...but mortified at the prospect of being caught.

I believe I was 8 or 9 and had always had a curiosity of sorts in the back of my head about the womens garments I would see in the Sunday paper and in misc. movies I maybe shouldn't have been watching at such a young age. Like many, that led to me going through my mothers drawers each and every time they had gone out and left me home alone...this carried through til my late teens when I left for college. I really love the various materials of women's undergarments and the way they feel. Safe to say I too am hooked and get some very strong urges to dress at times.

Hi everyone

I started with Moms panties at age 5 and loved it . When I was 9 she helped me dress as a girl fro Halloween panties slip and petticoat dress shoes the works and I was hooked.
She did not take the things back after and I dressed off and on for years I now live fem 24//7 and just turned 69 . It has been a long and wonderful journey.

Hugs Annette

Rikki Dove Honey Congratulations for you sweetie.

The truth is some men are more manly than others , at age 14 I had breasts and a hot woman whispered in my ear that my tits were bigger than hers and I should wear a brassiere and her lips touched me when she said that word , a week later I saw a black lace bra on the floor of my sisters bedroom , I tried it on and almost feinted from the wonderful sensation , it fit me like I was measured for it
and I have loved wearing a bra ever since .

As we age , men turn into women it seems and women get more masculine . Since I turned into a sissyboi at age 14, I wore my moms stuff next and got caught in her bra girdle stockings and slip
all excited and just about to start mincing in the mirror as I looked quite cute with breasts in sexy lingerie, so

my mother was as confused as I was so she asked her gay friends what she should do to help me , she shopped for me and got me my own lingerie, their advise to keep me from stealing as boys
with a sexual fetish for lingerie will tend to do and....

I have kept growing more female as her friends said I would, and I still adore wearing a bra now a 42C and now I love dressing up for men who like sissies in bras and stockings with slips heels and makeup . Some times I even wear my hair styled for a mans pleasure and a hair comb to look as ****ty and femme as I can for him and wear a blouse and skirt too , might as well wear as much clothing as you can if you are going to get stripped right away to your bra girdle and stockings heels to be a femme sissy for real men . So that is where you are heading honey let me know if you ever get to the state of Az we can play , I buy the drinks .

I remember being as young as 5 or 6 when an older girl who used to look after me after school putting lipstick and nail varnish on me and me loving it.

I was probably 14 or 15 when I first started trying on the odd bit of clothing when the opportunity presented itself, and 21 (last year) the first time I ever went full wig, make up, dress and actually passed for a girl.

I was very very young when I tried cross dressing. I would try using shipping box corner isolators tied together with string. It worked until someone found them and removed them.

the first time I was in first grade I put on my sisters panties and tights

I started later in life than most. I used to wear my wife's lingerie during our first years in college.

I believe i was about 6 or 7 when I would play with a neighbor girl, Cathie. Her aunt lived next door and we would play at her house. Cathie wanted us to play as girlfriends and would bring some of her clothes for me to wear. I loved being her girlfriend! We would experiment with aunts make up and i felt so pretty. I then started wearing my mothers clothes when I was home alone.

Vaguely. In my younger teens with what was available. Panties only, I recall.