What's Your Earliest Crossdressing Memory?

[Xandra]

I wonder how many of us can pinpoint a time we first crossdressed? Or a time we first wanted to?

I can remember my mum, dad, and brother being out of the house--likely I was around 7 or 8--and I took one of mum's fake fur coats from her wardrobe and paraded down the hallway like a catwalk model as I looked at myself in the mirror.

I don't think I had a clue at the time why I was doing what I was doing, though I do recall the thrill.

Alex

[Anne2345]

I remember when I was 3 or 4 years old over Christmas that an aunt of mine painted my toe nails red as a joke. All the adults thought it was quite funny. But I loved it! I absolutely loved it! I did not want it removed. The memory is quite vivid even now, almost 40 years later. I also remember when I was 5 years old trying on a girl shirt belonging to my younger sister. It was too small, and I could not remove it myself because it was too tight. I had to ask my mother for help getting it off. She was not pleased. Lol! These are my two earliest memories of CDing.

[Kathryn Philips]

My earliest memory was when I was 4 years old. I used to play a game with my female cousin, 1 year younger than me. At our grand parents home we would go to the end of the graden where there was a small stream whith a bridge over it. The to of us would hide under the bridge and swap underwear. I don't remember how this came about in the first place, but I'm pretty sure it was my idea, I am and always have been a crossdresser. I also remember asking my mother if I could wear some really nice white girl's sandals, she let me a few times.

[Stephanie47]

I can remember putting on one of my mother's nylon gown when I was a single digit midget. It had nothing to do with cross dressing. Slightly older, but still pre-teenage, I use to try on my mother's slips which hung in the bathroom to dry. There was still no cross dressing motivation. I think in my mid teen I transitioned into cross dressing when it lead to sexual satisfaction, if you know what I mean. Now I share my male body with the woman that also dwells within.

[christinac]

I was about 11 or 12 I wore a black bikini that belonged to a friend's sister.

[Teresa Ann]

Hi everyone I have pictures of me in a dress at around 4 years old and when my wife saw these she was more accepting of my dressing and even helped knowing that it is part of me. I guess I have to thank my older sister for that, and my mom for taking the pictures. Teresa Ann Mudd

[kimdl93]

I'm sure that for most of us, the moment we tried on that first garment is pretty much indellibly etched in our memory. For me - I suppose I was 4 or 5. One of my earliest memories of any kind was putting on one of my older sister's slips. That along with a persistent memory of a dream that probably occurred when I was 3 or so...of women in stockings, garters and bustiers....a swirl of these gorgeous images floating through my mind...and all I could think about was joining them. Can you imagine having such an odd dream at such an early age!

[ziggie]

I hadn't thought about this in years but, when I was quite young - pre-teen by my memory - my mother and sister used to do pedicures for me. Mostly clear polish, but sometimes colored. I'm surprised my dad, a very traditional 1950s father, allowed it, but I don't remember any problems.

I still enjoy having a pedicure done by my wife.

[Wendy_Marie]

I remember getting mad at my older ister when I was 5 because she told me I was a boy and would never have boobs...when I cried and hit her she ran and told Mom, who in turn called dad who then had the "Differences between boys and girls" talk with me.
It was a couple of years later when I actually dressed for the first time...I was about 7 1/2 and found some of my sisters clothing inthe bathroom where i was getting ready to take my bath before bed. I tried on a slip, panties and pantyhose and then climbed atop a pair of candies Mules she had left in the bathroom....That was it for me. I stole a nightgown from the hamper and began wearing it to bed nearly every night...after all isn't that what girls are supposed to do?

[rachaelsloane]

When I was 4 or 5 I remember playing with the girl that lived next to us and playing girlfriends by wearing her panties. I think I then went home and tried on my a pair of my mothers stocking. Little did I know what it would lead to.
Rachael

[TGMarla]

I remember the first time I put on a pair of pantyhose. I actually did this for reasons other than curiosity or crossdressing. But it got me hooked with one try. Ha! Even heroin isn't that strong! [SIZE=1](Umm....I don't know this from experience.)[/SIZE] Anyway, I know that's when I started crossdressing, but I don't remember the very first time after that when I acutally sought out additional women's clothing and wore it. It's all a blur. Before I knew it, I was dressing head to toe...well, actually the bottom of my neck to toe. I didn't have wigs, and didn't try makeup for many years.

[Taylor186]

I was about 5 and tried to fashion a dress out of a bath towel.

[steph1964]

I was probably between 5 & 7 and my older sister put one of her dresses on me. I still remember it was brown and had a frills. She then told my parents who laughed. I acted embarrassed but loved it. After that I would dress in my sisters clothes when no one was home. I have memories of staying home sick from school and dressing in her school uniform. Before we were teenagers she would take colored pencils and put makeup on me. She has no idea.

[Jilmac]

As I've mentioned in numerous other threads, my first rcollection of any kind of crossdressing was when I was 7, years old. A cousin of mine dared me to put on a pair of girls panties and a dress. I remember it was summer and it was hot. We were in the attic of the house our families lived in (my family downstairs, his upstairs). The panties were white nylon, very smooth and soft against my skin, the dress was yellow with red flowers. As soon as I felt the smoothness of the panties and the flowing of the dress as I walked, I was overwhelmed with euphoria. The euphoric state didn't last long though because my cousin grabbed my boy clothes, locked me in the attic, and told me that he was going to bring his friends to come and look at me in the girly clothes. I got scared and hid under an old bed and wouldn't come out until he returned my boy clothes.

After I got over the fear of being seen by his friends I started experimenting with dressing in my three older sisters' clothes. Panties at first then other items like stockings, girdles, garter belts, and bras. I dressed completely for the first time at age 15 and it felt so good, I never stopped.

[sissystephanie]

I was somewhere between age 6 and 7 when I first tried on my sisters panties. I was hooked from that point! they were rayon and felt soooo good!! That was a little over 70 years ago and except for 2 rather short periods I have been crossdressing ever since!!

[Julogden]

As far as I can figure, my earleist memories are from when I was no older than 3. My mom let me have an old petticoat of hers that I wore a lot, and I used to get into her makeup and try to put on lipstick back then too. I used to go into her closet to look at and touch all her dresses, and I remember thinking that I'd have lots of dresses like hers when I grew up to be a lady.

Carol

[katesometimes]

My first time was when I was about 10 or so. I was playing in the basement and found a garment bag with my mom's wedding dress in it. All that lace and beading was beautiful and I just had to try it on. I can remember that even at that age I was too big to do up all those buttons up the back. After that, I quickly graduated to hunting down and trying on my mom's nightgowns.

[Diane Smith]

When I was 2-1/2 to three years old, my mom started occasionally putting lipstick and/or nail polish on me -- I think she liked having a real live "doll" to play with! I didn't initiate it, but it felt neat and I didn't object.

At age five, I was in a summer preschool that met in the basement of a local church. They had separate "dress up" areas for boys and girls to play in that had some old adult clothes I assume were donated by parents. I remember feeling very frustrated that the boys were not allowed to try on the women's clothes. I recruited two or three of my male friends in the class and thought I would lead a "raid" on the girl's play area. I guess I figured the adults wouldn't stop us if we all did it as a group. I got so far as to put on a pair of high heels (not surprisingly, way too big for me) and took a couple of steps in them before one of the teachers firmly stopped me and escorted us back to the boy's section. My buddies were totally useless and faded from the scene at the first sign of a teacher glancing our way, so I took the rap entirely on my own. I don't know if that was my very first experience trying on girl's stuff, or if I had already started doing it at home, but it's the earliest I remember and certainly the most public.

I guess I had the last laugh because now I wear heels all the time, and they fit!

- Diane

[Danni Renee]

My first memory of dressing was about 7 or 8. My two sisters dressed me in a dress, put makeup on me, and styled my hair. I loved it and felt so comfortable. I strutted around the basement for an hour before my father came home. He took one look at me, yelled for about 10 minutes and then did not speak to me for the rest of the day. Sat me back 5 years and still scars my outlook today....

[erickka]

I was about 6 or 7, mom and dad were ouy for the evening. Mom used my closet for all of her dressy clothes. I remember slipping on some hose ,one of the fancy dresses and a pair if spiky stiletto heel pumps. Guess I've been hooked ever since!

[flic]

So i guess the earliest memory of have of feeling tg, is from about 3 or 4. The first time i remember going to our dressing up box and putting on a bright yellow dress, charging downstairs and demanding everybody acknowledge i was a girl. I was never shouted at, or ridiculed for it at the time, which im grateful for. It did come back to haunt me in later life though when a girl who was one of my playmates as a child decided to tell the entire school that i constantly wore dresses as a child,,,that was pretty scarring, but im stronger now!
x Flic x

[Cynthia Anne]

I can remember when I was four, my sister would dress me up from head to toe!

[BLUE ORCHID]

Hi Alexs, I guess it started when I was three days old and Mom & Dad brought me home from the hospital in a little white dressing gown.
Actually my first memories are around five years old in my mom heels and nylons.

Orchid

[lizbendalin]

I can't pinpoint an exact time or age; but...i grew up in a home where going to church was important, we never missed a Sunday. On the Sundays we celebrated eucharist, I always did everything in my power to sit on the aisle (either inside or outside), because there I could see all the pretty shoes as they went up or came back from the front. I know those memories go back to 6 or 7. I'm not sure I dressed until I was around 10 or so (no big sisters, and a not very feminine mom - her closet wasn't that exciting). But, I always knew there was something different about me.

[audreyinalbany]

I was three or four---definitely pre-school--and used to sneak up into my parents' room and try on my Mom's girdles and stockings. Sometimes I'd clunk around in a pair of high heels and even tried on some of her clip on earings.