Where did you first crossdress ?

[Neetu]

It was in my cousin's house. they had all gone out of town and I was using that house to study (as mine was quite small). His mom had left her washed clothes lying on the closeline and there was a bra and her panties and a couple of other items. I was facinated by the bra and began wearing that and a blouse on top of that. I remember ignoring the panties at that time because it was a coarse cotton one, not the frilly type I love. Plus the bra is so much more 'woman' than anything else! I guess that is why I was attracted to it.
I would wear the bra and stuff it with whatever was nearby to produce the effect of a bust and wear the blouse and then study in that room, blissful in the feeling that a tight bra engenders!
But the real step up to CD world was when my brother got married and i had access to my sis-in-law's clothes. Now there was everything available and there were many days when i would be alone at home. Oh, I treasure the memories of those blissful days when I could wear anything (they all fit!!!) and move about the house without any worries!
If only life were like that now!
Neetu

[Joan]

Hi Neetu

Like you I have borrowed items of clothing. Apart from my wife's clothes that is mostly in the past for me now.

I found that i also get a thrill from shopping for my own lingerie items. I do this in male mode as I do not have the courage to go in public en-femme. Do you shop for ladieswear or lingerie in India or does your culture make that difficult?

Joan

[Ms Denier]

I also grew up cross dressing at an early age. Mostly in the bathroom wearing my mothers nylons, but never enough time to really enjoy it the way I wanted too. I will never forget that first time I was now old enough to be home alone feeling to sick to go to school. That was a magical day as I wore my mothers open bottom girdle, sheer RHT nylon stockings, short silky slip and her highest spiked heels all day!

Also every home I ever visited as a boy I would always hope to find nylons hanging in the bathrooms as most women did in those days. I would never miss a chance to quickly slip on those silky nylons for a quick needed fetish release.

But my first time really dressing up outside of my own home with any quality time to do so was one summer when I was 14. My best friends family went on a two week vacation that summer and I was to feed and care for their cat. I was shaking with fetish bliss knowing I would be in the house alone and able to wear his mothers and older sisters stockings, garters and high heels. His older sister used to always wear these beautiful black nylons and pointy toe spiked heels. She was tall and her long nylon stockings and heels fix me to perfection....pure fetish release every day for those two weeks!

[Belinda]

In my bedroom. I wore a pair of my mums tights and my school football shorts. i didnt know if my Mums skirts would fit me, I was thrilled to see how good my legs looked in tights, even though I was short. Couldnt stop thinking about my first experience in school the next day. Little did I know that it would get better, I eventually started trying on skirts with the tights, i have naturally curly hair and was very petite so I must have made quite a girl, no makeup alas.

[Becki]

When I was about six yrs old, in my Mom's bedroom, I put on my Mom's Bustier & High Heels.It has never stopped since.That was about 60 years ago.I aways felt I was in the wrong body.Acting to be male.
Hugs, Becki

[LeeAnn]

First time cross dressing? Hmmm I remember just barley having to wear a pair of my sister panties when I was like 6 or so because my mothers washing machine was on the fritz and she had not been to the laundromat before I ran out of underwear. I also remember I liked the way they felt. But I don't think i would call that cross dressing per say.

The first time was about 4 months ago or so. I was in Walmart passing through the women's panties section. A pair caught my eye. They were in a package with 2 other pair. I put the package in the shopping cart and continued shopping. When I got home I took them out of the shopping bag and tried them on. I almost went crazy with the feeling. I have continued wearing them for a few months until I started buying other things (I have 2 bras, some stockings with a garter belt, about a dozen panties, 3 nightgowns, a dress, a skirt and two blouses).

[Carol Esme]

Not counting, the odd items that I experimented with as a child, the first time I fully dressed with wig and make-up was after I got married and had access to my wife's stuff when she went out. I particularly remember a long button up the front denim skirt and a knitted white sleeveless top. They were my all time favourites. I was less thrilled by her long dark straight shoulder length wig with separate fringe on a velcro velvet headband. Didn't suit me really but it was a start.

[Kittie]

Probably as a young lad (girl)
Really it was about 12+ years ago when I realised I had boobs and thhey needed supporting. I then bought my 1st bra and loved it!

[Bernice H.]

Me it was at a Holloween party
I was dressed as a french maid
Got many compliments
Loved it. Now i can't wait to dress