What is your fondest memory of your early crossdressing?

[Jenniferpl]

My mom had longline bra that I would wear every chance I could.

[adrienner99]

I used to pretend to be sick and stay home from school to dress in privacy. My mother had one petticoat which I adored wearing, plus a yellow silk evening gown, black patent high heels, and even gloves. Diamond clip on earrings, too.

With my short black gloves on, I would open her Revlon Cherries in the Snow lipstick. I learned quickly to apply it quite well.

It was heaven.

[Rachel05]

I too remember those early days with great fondness, my mum had some really nice underwear and I used to find it very nice against my skin and I worried so much in them early days about leaving the drawer contents exactly as I found it so she would never know

Yes I used to use rolled up sock to fill the bra's out and my favourite dress of mums was a really nice short white one and by the time I was about 13yo it used to fit me perfectly, I think I used to wear it more than mum did

They were great if not sometimes a little confusing days

[JennaR]

All of those things bring back fond memories. I guess the zipping of the skirt somehow strikes a nerve or the first time I tried on a wig. But I have to say sharing my pictrures to the world through this forum after having to be so carefull that no one ever saw me dressed can't even be measured. Yes, freedom from fear.

[APRIL0401]

I was lucky. During my high school years I had a part time job cleaning classrooms after school for this Catholic grade school.
I found this closet containing girls school uniforms. Girls donated their old uniforms after graduation from eight grade. I was a skinny little kid at the time so the clothes fit perfectly. Many days after I finished work and all the nuns and teachers were gone I would try on a white blouse, the plaid jumper, and the knee socks and walk through the hall ways and go in the eight grade class room and sit in a desk and pretend that I was a school girl. I would do this a few times a week. I would even go outside during the winter months when it got dark early. Those were great days.

[Midnight Skye]

One of my favorites was my first swimsuit. It was white with tiny blue flowers all over it, and it was soft cotten fabric. It was also slightly too small so it hugged me tightly. I can even remember it had crossed straps in the back. I just adored wearing it when I could.

[ArleneRaquel]

OMG - You expect me to remember that far back ECK !!!!!

[Carol A]

I was 14 and poodle skirts were all the rage, I would wear my moms squaredance skirts with 2 or 3 can cans under it put on a bra and sweather and pretend to be like the girls in school.

[Pamela Thomas]

I discovered pantyhose and long leg pantygirdles. The silky feeling of the pantyhose was wonderful. Pulling the girdle on and the feeling of it on was so exciting. It was very pretty.

[JustAlex]

I mentioned the pillowcase the other day and now I ran into this

Pillowcase nightie

I'd love to have one.

[Frédérique]

Can you describe that feeling when you first put on that skirt? Remember the sensation as you raised it over your hips and then closed the zipper in the back? That feeling of being a girl for at least a little while. Does anyone have any memories to share with me?

[SIZE="2"]Yeah, my girlfriend (at the time) left some of her clothing at my house one day. Nobody was around (I think my father was weeding a flower bed), so I put on a skirt and just enjoyed wearing it for a while. If I had felt “silly” in some way, I wouldn’t be here now, but, since I was pre-disposed to feminine things, tactile objects, and free thinking, I reveled in my re-birth after this minor transformation. I went onto bigger and better things, always just out of sight, giving free reign to my sensitive urges. It was a joy to feel the “male” melting away, and I wanted to be in this newfound state as much as possible (still do)…[/SIZE]

[Sarah Doepner]

I'd been caught by my mother but this was before counseling was commonly available so I was sent to spend my way too much free time during summer vacation with my dad and his new wife. My mother and stepdad figured I needed to be deprived of the opportunity and maybe it would cure me. However, I guess the reason for the summertime visit wasn't shared. I was put up in a basement bedroom with an old wardrobe full of girly things that fit me just right. I'm still in love with that short blue dress.

I came back cured! Yep, I wasn't caught by my parents ever again.

[cindycd]

I was 6 and I wanted to trade clothing to shock everybody and to my surprize, I was the one who loved those red pantie's and that green jumper that we traded. After that I couldn't wait to trade with her at any chance we had. Fortunatly for me our familie's were very close so I could do sleep over's all the time and she would let me wear her pantie's and nightie's all the time. Over the year's she never said no if I asked to wear anything of her's and she even used to help me and pick out stuff for me. Unfortunatly she died accidentally about 15 year's ago, and I still to this day love her dearly for being the most under standing woman who ever walked this planet. I wish all my girl friend's over the year's were like her.

[Avana]

fondest -

probably when i was 5 or 6 and I would lay in bed at night dreaming that I could step into my closet and magically transform into a little girl, with a closet full of dresses.


most exhilarating -

when i was in high school i made a few daring runs into the girls locker room during after-school practice to 'borrow' some bras and skirts

[ringedjohn]

I have lots of lovely memories. I remember the first time I put on a pair of nylon panties - lovely exciting smoothness. And the first time I pulled on nylon stockings and fastened them to the suspenders of my open-bottom girdle. I remember the thrill of wearing a bra for the first time. And having my ears pierced and wearing drop earrings. And - lots more......

[ArleneRaquel]

Seeing da covered wagons roll by.

[Monika G]

Thank you for sharing your memories with me. I hope I brought back some pleasant memories to you. I enjoyed reading your responses. I am glad I finally started a thread that struck a cord.

[Lynneth Lee]

[SIZE=2]The first I remember was at about 6. I tried on some of my sisters underware(she was 10). That felt so wonderful, the next time I went to visit mt father & step-mother, that I boldly asked if I could sleep in one of her nighties. She laughed and said they may be too big but, that she had a slip that would fit!(It was satin-WOW!) I thought I had died and gone to heaven! When I slipped it on, there was this feeling of pure joy. They both laughed at me, but I didn't care. I'm afraid Dad didn't like this much and discouraged any more dressing. But my step-mother had lots of satin tap panties and I would sneak a pair to wear to bed every night. Oh, those wonderful days!!![/SIZE]
[SIZE=2][/SIZE]
[SIZE=2]NANETTE FAYE [/SIZE]

[ellenwannabe]

Back about 1971 I got completely dressed with wig and makeup and drove 25 miles to the city and went to the college I was attending and then went to a dept. store and had a hard time when I realized I needed gas and had to speak with the attendent that pumped the gas as my voice is very manly - I had a ball that day and that was my 1st time out by myself enfemme - loved every minute of it and have ever since - Ellen

[Sarah...]

No fond memories for me. Every experience was an exercise in reminding myself that while I knew I was a girl (in those days) everyone else thought I was a boy. Now I have the maturity to say who I am things are much better.

[willowgurl]

Hi My fondest memory was the first time my friend Jonny and I went on a weekend camping trip, and was girl dressed the whole time. I sort of became Jonny's "girlfriend" that weekend. Willow

[Myopedee]

There were several although three stand out. First, was the first time I put on one of my mom's panty girdles. I was then hooked on girdles. Second was wearing one of my mom's suits. Skirt, top, and jacket. I felt so completely dressed and it was my first skirt experience when I figured out you cannot run in one-lol. For those two I was propably 13 or 14 so I was about the same size. Third is when I was over a friends house and she stepped out and I wore her Girbaud denim skirt with FAB deep pockets for about 45 minutes. I was bummed when she returned although I have since bought two on Ebay over the years.

[Christina89]

my fondest memory of CDing is when i first started and how i started.

[ArleneRaquel]

At age 20, I wnt out very late on a number of Fridays ( actually AM Saturday) fully enfemme as Maureen, boy did I have a good time.Sexily, but tastefully dressed.One one ocassion the Cabbie wanted my phone#.

[Ms. Laura]

I remember when I was about 10, maybe 12, I had already discovered pantyhose. They were wonderful. However, my grandmother was quite a fashion plate and had a variety of designer things, plus she was quite young as grandmothers go. She had a pair of 3" heels, sandals, they were like a red and white bead design and I was just transfixed looking at myself wearing heels and hose. I think this is where I realized that all things feminine were what I was after, not just hosiery for kicks. I wish I had never outgrown her things!