When did you first crossdress?

[Carla4Guage]

I've told this several times. I first dressed in something feminine at age 59, and yes I am a bit slow! But sister look at me now!

[claire1d]

Must have been around 12, I still see myself exploring my mom drawers.

[Jen84oh]

I was around 6 and tried on my moms pantyhose and love it.

[Kallyope]

First time at around 5... got more serious into it at around 11. So serious that I was feeling more female than men and was totally dreaming about become Calliope full time. But with the kind of family that I had, it was (and still is) unthinkable.

Tried like hell to quit several times. And eventually quit quitting

[carahawkwind]

Found some of my mom's lingerie when I was around 12 or 13, very much a puberty thing.

[Janine cd]

I'm thinking about age 7 when I tried on my mom's shoes. Then again I remember trying on her nightgown and slippers also.

[CindyR]

For me it was when I was 7, I wore one of my sister's dresses and heard my father coming up the stairs. I hid in the closet(no pun), and he found me immediately. To his credit he just told me to get out of my sister's clothes, didn't make it a big deal. Later that year I was out of pants, and told my mother. She made me wear my sister's purple polyester pants to school, I was embarrassed. I had to walk 6 blocks there and 6 back.

[Karolyn]

I was 12-13 when I tried my mom's satin PJ. That's when I knew I wanted to have more satin clothes, but it was hard to find for men. Switched to women ones, and there is no comeback

[Lisa Diane]

I was about 8 and mom was visiting the neighbor lady, for some reason I went into her room and got in her dresser. There I found a padded bra and tried it on, the feeling was wonderful, I had boobs! Years later I had to take out the trash and there was that same bra, it came back in with me and I kept it for quite some time.
Lisa

[SerephineStar]

I started crossing when I was about 12 years old. I was always curious about panties at a young age and I attempted to make them with my own little boy undies XD but that didn't turn out as planned. I eventually started to take my cousin's stuff (I was a weird kid I know) and my mom would forceably clean my room and find stuff so hiding things was virtually the hardest thing to do. but when I was around 14 years old she stopped and I was able to keep up a good amount of stuff to wear. so I guess I can say that I've been crossdressing for about 7 years now.

[RobynT]

I was very young, about 3rd grade I remember getting excited over a classmates yellow dress. I wanted to wear one just like it. As puberty took hold, I became very interested in the laundry hamper. mom and grandma's panties and slips. The feeling was earthshattering... continued thru the teen years ever so deep in the closet. Lots of questions and confusion over the years, but am at a point now that I am good. I guess wisdom comes with age. I am who I am, I do what I do, if you dont get it, that's not my problem. live well, be happy , dress often...

[heather ann martin]

I can't remember a time when I didn't crossdress. Having older sisters meant there were always plenty of dresses, skirts, etc. in the house and I took full advantage.

[MichelleDevon]

Definitely pre-school for me so probably around 4 years old so that makes it almost 60 years! I used to love t wear my mother's nylon slips and feel the slippery fabric against my skin. It was years later when I first got the opportunity to wear hosiery - my mother almost never wore stockings but I did find some as I rummaged through her drawers about 9 or 10 years later. The rest, as they say, is history! I still love nylon and satin lingerie, even better when you can wear them under a skirt or dress with a satin lining, and teamed up with sheer nylon and I am in heaven.

[CD Tammy]

I was five or six. I know the age because of where we lived at the time. I was in Kindergarten or first grade. My step-monster was a socialite who dressed up for everything. I don't think I ever saw her in pants. Since she had way too many clothes, she used the closet in my room as overflow. The closet was full of dresses, skirts and blouses. One Sunday, after church she had to do a quick change from her church outfit to some more formal outfit.

On my closet floor she left a pair of Size B, Leggs Sheer Energy, suntan shade pantyhose. I don't know why I put them on but that was it. At first, I wore them under my pajamas every night. Now, this woman had closets full of clothing. Dressers full of clothing. She never noticed over the years, but she lost many pairs of tights, pantyhose and yes, even stockings. She "lost" nighties and other dainties. When I said that she had a lot of clothing, she had two whole dresser drawers full of pantyhose!

[miko]

I was at the age of 10-11 I remember I had a whole day alone at home
I started playing with my mom's makeup and I wore a corset

[RachelsMantra]

I was a preteen and I found my mom's stocking on the trash. I was curious about the texture and just had to try it on. It felt so good on my skin I was instantly hooked and have been obsessed with nylons/stockings/pantyhose ever since. For awhile I was only into pantyhose but over the last few years I've been working my way to fully dressing including makeup, etc.

[Crystal Beth]

I was 6 and it was at summer day camp. There was a trunk full of lots of clothes for both genders to play dress up with. I was drawn to the dresses (go figure). As the years went by I was stealing my mom's or sister's clothes and wearing them if I was home by myself. I would fake being sick just to stay home and play with the clothes, always being careful to put things back exactly the way I found them. After I was out of the house and living with girlfriends I would wear their stuff if they were out of the house. My only regret is that I have better fashion sense than all of them combined

[Susan Thomas]

We were on vacation in Canada and I was about eleven. My aunt and uncle thought it would be a good idea to hold me down on the ground and make me wear one of my aunt's bras. When we got home from vacation, I had a new-found attraction to my sister's clothing. I started wearing my sister's panties and then her swimsuit. One day, my mom got home from the grocery store, earlier than I had expected. She caught me red-handed wearing my sister's swimsuit. She started yelling at me and asking me "do you want to be a girl"?

Apparently, she put the fear in me, because I didn't crossdress again for ten years. I really didn't have a desire to crossdress, but one day (ten years later) I had an epiphany. I had just finished having a shower and there on the towel rack were my mother-in-law's pantyhose! Before I knew it, I was slipping on the wonderful pantyhose. I will always wonder if being forced to wear my aunt's bra was the genesis of my crossdressing? Years later, my aunt mailed me a picture they had taken with me wearing the bra. I look very upset and unhappy in the picture. Does anyone think that I would be wearing a bra a panties right now, if it hadn't been for my experience with my aunt's bra? Just wondering . . . . . . . .

[droopydog]

Around 10 or 11, sister had a wet look black one piece bathing suit ,just had to try it.

[sweatcakes]

I remember trying on panties and a bra at age 12.

[Jaidyn]

Very young for me. I could barley dress myself. I remember trying my sisters clothes when I was about 3 or 4.

[Dana3]

I've always been since a young age been attracted toward the feminine side

[Alice-n-wonderland]

Always been attracted to feminine fashion, as long as I can remember. It was the nylon clad legs that really caught my eye though. Tried on my first pair of hose at about 8. Can't hardly live without them now. Over time every thing else followed along. Now I go out as a girl, always in a dress and hose.

[CharlotteP]

My sister dressed me in a ballerina outfit when I was really young, like 5 or 6 and I remember that I thoroughly enjoyed it. After that it was when I was about 11 or 12, I wore a pair of my sisters panties. I kept it at just panties through all of my teen years and occasionally through my 20's, it wasn't until my 30's that I took it much further and started dressing fully, and under dressing full time.

Charlotte

[jasmine lee]

I was probably 5 or 6, at my Grandparents house, they had a box of dress up clothes, and I put on one of my cousins old school uniform dresses and wore it outside playing with my cousins. My Grandfather saw me and he wasn't impressed.

Later in my early teens, my Mum and Dad both worked, and I would fake being sick so I could stay at home by myself and wear my Mum and my Sisters clothes. Later while still living at home, I would by my own clothes, but I got caught a few times.

It wasn't until I was in my early 20's when I moved into my own house and really started my alternative wardrobe.

Jasmine