Crossdressers-Haven.com

Woo hoo Rayla. What a wonderful beginning for you. Once you started wearing pretty feminine lingerie and perfumes, you were going to be a lady for life and isn't it such a wonderful thing to have happened to you.

My mother's old girdles, from the 60s. Eventually adding a support bra, that I filled with my socks.

I can't recall. I am not even entirely sure if I was wearing women's clothes at the time, I was still quite young and it is just too long ago for me.
Some of you recall things from even longer ago, but this memory is one that I had almost forgotten about and not very vivid.
I want to say something black or at least dark, but that memory is maybe not very reliable.

The second time, it was the full monty, up to and including underwear. All white. Even earrings.

The third time I think must have been blue or red panties that I 'found' in my dorm.
Actually, thinking about it, I think that might qualify as my first time as well, as this would have been the first time that I dressed myself.

I will explain in a new topic. But first I'll go have something to eat and then get fully dressed as that seems appropriate.

Fascinating to see how many here had experiences at such an early age.
Perhaps this behaviour at an early age is either more common than one might think and it is just that some of us do the same thing later, or it really says something about something deep inside of the people who do it when they get older.

Like many others I started with my mothers items when I was 8. I loved the feeling of her panties and slips. Eventually we were the same size I moved on to trying all of her clothes. I love the look and feel of women's clothes so much better than men's.

as far as I remember, it was a large well worn and liked pair of satin pantys of my mums, then a friend of my big sister stayed with us for a while and her clothes fitted like a glove, satin underwear and mini skirts....

Stepmothers tights (pantyhose), then aunties knickers. Long gap of nothing then sudden need to wear more, so ended up wearing gfs undies and stockings. Shoes came next but they were mine as much bigger feet than any gf i ever had. Led to full dressing later

Hello Girls,
I was probably 13 when I asked my neighbor if he could get me a pair of his sister's underwear. I loved putting them on and feeling the fabric, but they were pretty plain and spent more time in the drawer than on me.. My father had died by this time and I lived with two older sisters, my mother and my grandmother. For some reason I don't think I tried on their underwear or clothes.I was very aware of the undergarments they all wore and enjoyed hearing the discussions about the various items. I used to buy my sisters black bra and pantie sets for christmas, and stockings was a regular gift for any of them. Back then the department stores would have a number of thin boxes with each brand, style, color and size, that they would take these out from behind the counter to show you the stockings you were interested in. For my own desires I was interested in girls clothing outside of the family. I was and remain very close to my sisters and I was their "Baby Brother". I do remember at a very early age maybe three or four exploring the differences in our bodies in a fun innocent way,
I always have had a desire to have women's panties and when I would get some I would be excited and keep them until I began to worry about having my wife find them and I would throw them away.
Now at the age of 66 I have become so happy to explore cross dressing to my heart's content. My first dress arrived in the mail today and it was such a good feeling to pull it on over my head and have it fit and create the look I wanted.
Hugs, Stephanie

For me, it was a pair of my mom's black suede pumps with 4" heels. They made me feel so feminine and sexy. I was 12. After that, it was her skirts, then makeup. And they rest, as they say, is history.

I was very young 6 maybe 7, but I remember trying on my mothers girdle, bras and slips.. she often told people I was a silky baby. lol Little did she know.

started when I was 5 don't recall what I wore I know it was my mom's and as time went on I wore her dresses and shoes until I out grew them and bought my own dress

My first experience with dressing I put on a pair of a friends sisters panties and I was hooked from the start. I have been dressing for many years and panties are still one of my favorite items.

Remember sitting in front of the TV set watching Captain Kangaroo around 1956 or 57 with a pair of pale blue panty's that I borrowed from my older sister.

Yes, after all of these years, it has been those wonderfully soft and silky feminine fabrics that just touch and cling to your skin as you wear them.

For me, it was my mother's lipstick when I was about 5. From there on, it was panty hose, bra and girdle (yes, u heard me!). Went through a lull period until high school. Lost my first girlfriend when she found panties in my bed (mine) and thought I was cheating. Better to lose her than to fess up! Small town and I would have been a gonner!

I started out with a pair of panties that I stole from my sister back when i was 13 or so. It just grew from there.

I started with my mom's skirts.

But really came out in my late 50's donning a hoop skirt, lacey pantallettes, full makeup , purse, wig, bonnet and hooped very lacey petticoat.

Sold on dressing ever since.

Love dressing as and being a woman.