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! (Umm....I don't know this from experience.) 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.

[Deanna B]

hi honey . oyes i was 3 or 4 i think . i got my mum sexy panties and put them on and love it so i hide them and wear them . then i wanted to be a girl .much better clothes and a lot more colour and softer. love deanna b xx

[EllieOPKS]

Earliest I can remember was when I was about 4 or 5. My best friend was a girl 2 doors down from us. We would play together all the time. She invited me to tea parties with her dolls and we would role play as mom and dad. She suggested one day that she be the dad and I be the mom so we swapped clothes (except for undies). I can still remember how unusually good her leotards felt.

[marissa_sissy]

When I was young, I would sneak into my parents friends bedrooms and look at the females lingerie. As I got older I began to steal a pair of panties here, a slip or a teddy there. My desire was always lingerie and panties, and still is. It started by my account by the time I was about 8. I also stole a french maid lingerie set from a friends mom in junior high. (blush) That was when I realized that the whole french maid thing was what turned my crank. It was not till I got my first computer and internet connection that I even knew any male was into the whole sissy maid thing.

If nothing else your post has given me a chance to think about what a wild and crazy ride it has all been.

[dawnmarrie1961]

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

:devil:In the womb. I had was wearing my mother.:devil:

[NicoleScott]

My earliest memory of different desires began around age 4 or so. Looking at magazines and catalogs, my eyes were drawn to pretty women, especially their high heels and red lipstick, and to a lesser extent, their dresses, lingerie, and hair. In public, my eyes were always looking at high heels and lipstick. Around age 8-10, I started experimenting with lipstick behind a locked bathroom door, and high heels when I was alone. I have an older sister who wore very high heels, and her clothes fit me throughout several teen years. It wasn't until my late teens and into my twenties that I began dressing up and applying makeup for a complete transformation. It took years of trial and error and accumulation of makeup, clothes, wigs, and shoes before getting pretty good at it. All in private, the advantage of which is NO RULES, able to go for the look I love - overdone.

[joannemarie barker]

I remember my first time being my sisters swim suit at 11 but the memory that really stays In my mind was the day I first went to school wearing panties.I chose the day carefully,making sure I wasn't doing pe or anything too physical and picked a pair of satin peach panties from my sisters drawer.I remember having mixed emotions that day.I felt so good wearing something all of the girls in my class had on but looking at the boys and thinking I'll never be the same as you.

[minalost]

Sixth grade I think... sneaking out of bed and getting one of my moms bras out of the laundry basket. I put it on, stuffed it with socks, and went back to bed. Had a wonderful nights sleep...

[billie earls]

I remember I was around 4 wearing my mothers panties and putting a towel around my waist making believe it was a dress.

[Shadeauxmarie]

I think I was 6 when I tried on a pair of my mother's stockings from the trash. I loved the feel, even though they were ripped, and I can remember them smelling like my mother's perfume. They were too big, but i was completely hooked. I have loved stockings ever since. The old fitted style like Hanes with the great sheerness and dark RHTs.

[carhill2mn]

I was either 7 or 8 and I put on one of my mother's silk blouses. It fit me like a dress and I was hooked!

[Donna June]

I was about 7 and desperately wanted to try on one of my older sisters party dresses. When I did it was heaven. My 2nd time was a full slip. ooh la la, been hooked ever since.

[JustAlex]

I can't remember what was first. I have clear images of me wearing my mother's underwear at a very early age.
But one thing that most likely was my first try was a pillow case that I wore like a strapless dress. Although, technically, it wasn't crossdressing...

[Frédérique]

What's Your Earliest Crossdressing Memory?

When I was 3 or 4 I put on my aunt’s lipstick and makeup – does that constitute crossdressing? :idontknow:

[Gocaps14]

I was somewhere around 6-8 when my family was visiting another fam$ily with girls around my age. I snuck aroumnd and found some blue panties. I wore them under my clothes.Mom then insisted I get undressed for a shower and I was caught! Undettered, I wore some yellow ones the next day and well, we all knopw the rest of the story!

[donnatracey]

Didn't realize I was such a "late bloomer"! I first tried on 1 of my mom's dresses when I was in my early teens.....:sad:

[Xandra]

When I was 3 or 4 I put on my aunt’s lipstick and makeup – does that constitute crossdressing? :idontknow:

Yes, I would count it :)

[Xandra]

It's great to read of everyone's early memories. It's interesting how we can recall not just the moment but the feelings associated with that moment.

[donnatracey]

Like the feelings of fear/helplessness I had when the zipper got stuck on my mom's dress and she was due home soon........:cry:

[stellatoo]

Hi, I was 11ish and remember being "aroused" in my sisters school knickers (bottle green colour!!! Ugh) After that there was no stopping me! Even when my stash was found (again & again)

[Susan_Xdress]

My earliest memories of wearing anything female would be around 7 or 8; the first items were my mother’s slips. Not sure if that qualifies as a conscious ‘crossdressing’ experience or simple curiousity. I know they always felt wonderful.

I was 11, it was very wet day and our parents were going to be gone until very late that evening. As they couldn’t play outside, my older sister 14 and her best friend 15, decided to have fun with me.

Their intent was more to be mean and tease, than for any pleasure for me. Ah little did they know that from the first minute when they put me in my sister’s skirts and panties, I was totally hooked.

I never showed any pleasure. I acted upset and the more upset they thought I was, the more they dressed me. The ‘made me’ wear her school skirts, casual skirts, dresses, panties, bras, and slips and they fiddled around fixing my hair, putting some make-up on me and having me walk around the house. OMG ! To walk around openly in the house feeling those skirts and dresses around my legs ! I clearly remember making myself cry at times so they would keep on dressing me.

They dressed me up a few times after that, but that was the first time I wore female clothing and knew that I loved feeling girly.

[NicoleScott]

When I was 3 or 4 I put on my aunt’s lipstick and makeup – does that constitute crossdressing? :idontknow:

Let's pose that question to unaccepting wives. On second thought, let's not. Let's get some psychology academic with lots of letters after his/her name to declare it's not.

[NikiMichelle]

I was 4 or 5 when I started wearing my sister leotards (leggings)...all iI remember is how neat they felt...I have no idea what motivated me to try them on the first time though???

[WillowWriter]

I was 10 years old, if memory serves. My friend dressed me up as a girl because she thought I'd look cute as one. It was a very different feeling in girls clothes, then, my regular boys clothes. My hair was longer at the time, so no wig, but I wore a skirt, training bra and some girly top.

[Dealight]

Had to think about this one....still not positive...but I am SURE pantyhose played a role ! I can remember being fascinated with the feel of nylon...and trying on pantyhose on various occasions from various sources.....later on in my late teens it became an obsession which stayed with me...I still feel more relaxed and comfortable wearing a pair of pantyhose. Hmmmm...think I'll go put some on now......... :)

[dana8656]

Also 4 - 5, i remember sitting on the stoop in front of my neighbors house with the neighbor girl, she was painting her nails, I asked her if she could do mine, she did. when she was done, wanting to be like mum, I went running into the house to show my mum that i was just like her, she promptly scrubbed it off.

[t-girlxsophie]

10yo raiding my aunts closet when staying at my Grans house (mid 70s),I donned yellow maxi-dress,tan hose and pink button thru cardigan,luckily my colour matching has improved through the years:heehee:

Sophie

[aurora_erika]

I was 7 when I tried my little sister butterfly custom she used at school. I like it a lot.

[SusanQ]

We had a foster child living with us. I was an only child, so my folks wanted company for me. One day we were playing in the bedroom and she daed me to put in her panties and slip. I took the dare, and it felt really good. From that point on I was always looking for items from my mother and cousin that I could try on. Fell in love with panty girdles from the moment I tried one on.

[Alisa]

I was 10 or 11 years old and went all in my first time. My best friend's mother and sister dressed him from head to toe complete with wig, makeup, jewelry, etc and as he paraded around the house, they made such a fuss over him... especially his older sister on whom I had somewhat of a crush... I was jealous. At my first opportunity there after (parents were out for the evening), I shaved my legs (not sure why as I had no hair to speak of), put on a pair of my mothers pantie hose, full slip, mini dress, matching pumps, wig, added a little lipstick and blush.... headed out for a walk around the neighbored.... even attracted the attention of a car full of boys... (it was the early 70's and it was a short dress... lol)... Anyway I think I enjoyed the attention more than anything. Well that's my first cross dressing memory.

[kristinacd55]

I was 3 or 4 also....think I had been brought to a wedding and was supposed to be sleeping in bed. Got up and wrapped my blankie around me and pretended to be the bride walking down the aisle

[Juanita O]

I was about 10 when I first tryed on one of my mothers girdles and her stockings.

[Jennifer4cd]

It seems to me that we recognize our crossdressing tendencies at a very young age. I can clearly remember my friends mother painting our nails with pink Cutex nail polish when I was 5 or 6 years old. I liked it a lot then and even more now, 59 years later, now I

[Julie Denier]

I remember, as a toddler, clomping around in my mom's shoes. Much later, maybe in my early teens, I was poking around in a downstairs closet and came across some of my mom's old clothes, and tried on a dress, pantyhose and pumps (the last time, until recently, that I had access to women's shoes that fit me). After that, until college, I'd occasionally try on some pantyhose, maybe a skirt and blouse, and try to squeeze into shoes that were by this time too small. Into my 20s and 30s, I maintained a curiousity about crossdressing, online or secretly ordering some tasteful publications. It wasn't until last fall, now in my late 30s, that I finally decided to dress all the way -- my own outfits, lingerie, hosiery, wigs, makeup, jewelry and -- at long last -- multiple cute pairs of heels that fit.

[Xandra]

It seems to me that we recognize our crossdressing tendencies at a very young age. I can clearly remember my friends mother painting our nails with pink Cutex nail polish when I was 5 or 6 years old. I liked it a lot then and even more now, 59 years later, now I

I think you make a good point. If "caught" at a young age, I wonder what difference the reaction of our parents' makes to our future dressing or desire to do so?

[mishmam32]

When I was 10 or 11 I can remember raiding moms dresser, she had a pantyhose and night gown drawer. I would slip on some pantyhose, and a nice night gown and parade around the house until mom got home. I also used to wear my grandmothers pantyhose around the house while she was out. One time my great grandmother saw me at the top of the stairs with pantyhose on, she just shook her head in disbelief. What always sucked was my foot would fit grandmas boring slippers, but would never fit moms cool heels. Everytime mom would disgard a pair of panyhose because they had a run, I would collect them, wash them and keep them under the bed. One time I came home from camp and they were all gone, deep down I know my parents know I CD.

[Allana W]

Year 1959, I was going into grade 2 and had begged my mother to buy me a beautiful pair of shiny, bright red girl's shoes. I wore them to school and was mercilessly harnessed by all the other boys. I dug in my little heels and insisted on wearing them every day for the whole year. Throughout my school years I wore various female articles, shoes, tops, jeans, and panties and a bra or two, much to the consternation of teachers and counselors. At one point I remember being sent to a psychologist and made to look at Rorschach inkblots. I always wondered if they learned anything interesting from my answers? This experience helped to form my life-long attitude about CDing. If people don't happen to like the way I look then they can just go look someplace else, thank you very much!!

Allana

[Danielle Gee]

Hello Everyone: The first experience I can recall is at the age of six or seven. I was snooping thu my older sisters room and happened upon a white lace,strapless longline bra. For some reaso I felt compelled to remove my shirt and try it on. It had about ten "hook & eye" closures on the back so of course I couldn't fasten it.

I remember my surprise at how stiff,scratchy and unyielding it was. But it was enough to start me down the road to a lifetime of CDing.:daydreaming:

Danielle:hugs:

[LittleCarol]

I remember thinking that it was pretty much like wearing a skirt when you wrapped a bathtowel round yourself. If you you wear white briefs and pantyhose an upskirt shot looks very much as though it could be a female good enough to let you take such a pic.

[julia ann]

About age 4 got caught wearing my mom's bright red lipstick I was fascinated, captivated, hooked and busted. That memory never left me and to this day I love bright red lipstick, even though while growing up I knew I was the only male on the face of the earth that had ever tried on make-up or had thaoughts of wearing women clothes. How much more wrong could I have been?

[durhamgirl27]

Probably around 10. The first time I dressed I think was in my sister's school uniform (we went to Catholic school). Still love the schoolgirl clothes today :)

[Randee]

I was 10 when, out of overwhelming curiosity, I came home after school on the one day a week the house was empty, found my sister's dance bag and changed into my sister's dance leotards and tights after first putting on a pair of her silky panties. I had about an hour or two that one day a week to mince about the house and admire my girlified image in every mirror and enjoy the feel of the panties and the leotards on me. Been hooked on them ever since.

[Jenniferpl]

When I was 7 or 8, my older sister has left a bra in bathroom and I tried it on and the rest is like a blur.

[Nicole Rose]

My remember when I was 5 years old being totally infatuated with a pair of pretty glittery high heels in the costume bin in my classroom at school. Ever since, I've been addicted to heels! lol

[MrKunk]

getting into and attempting to wear my step sisters tights and swimsuits

[Noortje]

I'm not really sure I remember the first time I actually put something on. I do remember my first crossdressing feelings, though. I was reading a comic about Huey, Dewey, and Louie (or Kwik, Kwek en Kwak as they are known to me). This comic featured their female counterparts (I guess they are Daisy's nieces?). For some reason, the three boy ducks dressed up as girls to trick the three girl ducks. Including fake lashes, which are the only way to tell boys and girls apart in the Disney universe. I do not remember why they dressed up, or what hijinks ensued. I do remember a powerful feeling throughout my entire body that this was awesome. I was not old enough to realise that those feelings were considered inappropriate, but through luck I kept my mouth shut anyway. That would have earned me a beating for sure.

[Alyssa Marie]

When I was 8 i was at my cousins house she was showing me her room. I saw a stuffed doll with a really pretty dress on the self and went right for it to check it out. I knew right then i liked girlie things and that I felt like a girl. a few months later when I was 9 i tried on my mom's lipstick in the bathroom.

[FAVORITE HEELS]

I was about 10 when I first tryed on one of my mothers girdles and her stockings.

same here 10yo girdles stockings and heels wearing.It seemed right to be curious about all these underpinnings and frilly things. its funny how we figured out stocking garter and girdle fastening at a young age.I see ther are alot of CDers that do at even earlier ages.

[JulieC]

My earliest crossdressing memory didn't involve any clothing or makeup.

I was young, around 4. Earlier in the day I'd watched a (non-animated) episode of Batman. Batgirl had been tied to a conveyor belt, and was barely saved from a horrible death in some machine. I was fascinated with how she was dressed. Later that evening, in bed, I tried to contort myself to being in the same position as her, and was wishing I was dressed like her.

It was years before I crossdressed for the first time.

[Crysten]

Younger than I can remember, maybe 2 or 3 yrs old. At about 4 I came down the stairs at my grandparents house, during a party, wearing a dress heels makeup....all dolled up from a 4-yr old's perspective. My mom used to have the pictures, but I haven't seen them for years.

[pantynhoseman]

My first memory was at a friends sleep over when i was 9. We were camping in the back yard and his mom had panties and pantyhose on the clothes line. There was 6 of us there and one of my friends dared me to try them on. Well i did and ended up putting on a fashion show and the rest they say is history.

[Vanessac48]

I'm not sure of my exact age, but I'll guess I was 5 or 6 and I starting trying out my Mom's high heels and lipstick

[Lorna]

It seems that I was a relatively late developer. I had no sisters so they didn't try to dress me up and I couldn't be attracted to their clothes. I have no memory of being interested in dressing until I became a teenager (late 1950s). It was when I began to "notice" girls around me and became intrigued by their clothes - especially when they graduated from ankle socks to stockings and I wondered what it felt like to wear them. When I was 13 my grandmother died and that meant I was in the house alone for longer periods and used that opportunity to find and try on some of my mother's stockings and a skirt. From then on I would regularly put those things on when I came home from school and quickly realised that I needed something other than rubber bands to hold up the stockings. An old girdle just about worked but was a bit loose. However, it allowed me to begin to experience those delightful sensations of nylon-covered legs beneath a swirling skirt.

[Brenda Freeman]

I remember every year when the Sears and Montgomery Wards catalogs came out looking through the toy section for boys but also looking at the womens section at girdles slips etc. Probably started around 6 or 7.
I think maybe at 9 or 10 when I had the house to my self I would put on my moms girdle with garter snaps and put on nylons, and sometimes wear her shoes and a slip! She was a petite woman so everything seemed to fit pretty well and felt so wonderful!

[Xandra]

Thanks to everyone who responded to this thread. I, like everyone who posted, can look back to an early crossdressing memory; but I'd be curious to know what percentage of adult crossdressers began to crossdress later--as opposed to earlier--in life.

[AddyCD]

My earliest memory was of my sister playing dress up with me. I was probably 4 or 5. I also remember a time when my family was outside and I walked by my sister's room and she had this beautiful easter dress laying on her bed. I just had to try it on. This was probably around 5-6.

[lynnef]

probably around 5 or so, wondered what it would feel like to wear underwear w/ no fly... before that i'd actually asked my parents to buy me a pair of girls' flats for me (still remember, they were sort if iridescent silver), they gave me a funny look and of course didn't buy them :( at that time i was also often confused for a girl anyway, since i had smaller bones and long (past my nose) curly hair.

got caught a few times later too... fortunately I was never really beaten/disowned/etc, parents seemed more embarrassed by it than i was, heh.

[abbykins]

My earliest memory is in 1st grade (about 6 years old) when my small town had "boy/girl switch day". I wanted to participate, so my mom helped me dress up as a girl. I LOVED it ALL day. I was teased a little but it was worth it.

Another early memory around the same age was watching Wonder Woman on TV. I wanted to be her, so much. I can relate to the Batman and Huey/Duey/Luey stories :) And towels as dresses.

I had younger sisters but never used their things nor my mother's. Every few years I had another CD event, but it's only now that I'm really CDing.

Thank you all for this wonderful thread. It's helped me learn more about myself.

[daviolin]

I remember it vividly. I was 5 years old and I was up stairs putting one my mothers bra girdle and stockings. I heard her comming up stairs and I ran and hide in the cloest. Yeah like she wasen't going to find me. She opened the door and there I was in all my glory. I remember being so embarassed. She never said anything afterwords or told my father. But anyway I was hooked from that day on. Daviolin

[NyssaF]

That is soooooooo weird; that's almost exactly what my experience was. Except my cousin was only 9 months younger than me, and we did that when we were 5. Otherwise, exactly that. Though my cousin wasn't interested at all in wearing my undies, she had no problems at all letting me wear hers.

So many years ago!

[NyssaF]

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....

That is so sad, I'm sorry you had to go through that. :( My parents divorced when I was a young 'un, so i didn't have to worry 'bout that. My mom turned a blind eye, not wanting to embarrass me, I think...

[LoriAnn_CD]

I can't remember the exact age, it must have been about 6. I was in the bathroom and my sister's bathing suit was hanging to dry. I just had to try it on. After that I want to try more and more. My sister is about 3 years older than me so most of her clothes and shoes fit me well. I remember a favorite bra and pantie set, a red plaid skirt and turtleneck sweater that I loved with pantyhose and little kitten heels. She also had a very cute fit and flare dress that felt so sweet. In those early days I had the chance to use makeup as well. My aunt was an Avon lady and there were always plenty of samples laying around that no one would miss. I only wish there had been a wig around somewhere.

[nativegurl]

hi ladies...I would have to say when i was 10 years old...I was left home alone often and one day came across my mother leggs sheer suntan pantyhose and high heel. I decided to put them on and it felt great i was so turn on i had a killer booty and legs to go with it...So, i decided to rob my sister lingrie drawere try on her ****ty tight mini skirt and just xploded..Wink wink....I was hook...hehehehe...

[jim2jamie]

i was in grade school,taking a bath,knocked moms pantie hose into the tub.
decided to put them on,wow what a sensation they felt to me.
i was for ever humping the swing set probably 5 yearsold,always rubbing myself,gertting yelled at by my mom.
she use to tell people i was suppose to be the little girl.
i never put a dress on till recently.i love the feel,dress,no panties,nylons,undergarments,just a dress.

[Hiddenaway]

Oh my gosh, I was probably about 6 years old and my sister wanted to play dress up. However, she wanted to dress up as Daddy and wanted me to be Mommy. I will never forget the feeling of those silky panties and that silky night gown against my then smooth skin. :daydreaming: I have written a 3 page Word Document on some of the most memorable times that I dressed up and am still in the process of writing it. I just felt it was too large for posting and will be after I am finished. :sad:

Heather

[Xandra]

I would love to read that document, Heather. It sounds wonderful.

[Elena Ornamental]

My earliest cross dressing memory is a time my year older sister dressed me in some of my Mom's clothes (preschool age). But it's my second memory I want to share. At a summer church camp our group presented a "beauty contest" where we boys paraded around in some of the girl's bathing suits and lipstick. How everyone laughed when the most masculine boy in our group came out in a two piece. I had a black suit myself. When at the end of the week when we were all collecting autographs from our friends on the camp photograph, one girl (who even went to my church) "Alan, you made a cute girl". Ruthie. That's a real pleasant memory for me. She was a year older and soon left for college so I wonder what opportunity I might have missed, if any.

[Anna B]

It began with my female cousins dressing me up at about 6 or 7 - that was it - hooked.

Anna x

[eluuzion]

It was the gardener...in the backyard garden...with the zucinni...:heehee:

I could swear I just posted a reply to this question or a similar one a few days ago. Couldn't find it on my computer or this thread, so I dreamed it or I am beginning to lose touch with reality...not such a bad deal...could be fun...

Ok, I was 28, just returned to college for more plaques that would turn out to be about as valuble as the wood slab they were mounted on. I was picking zucinni in the backyard garden of my rental house, and suddenly a 12 foot CD fairy appeared....

oops...sorry, got a little carried away...back to story...

I went into the barn to toss weeds into trash can. When I removed the lid
a giant jack-in-the-box CD springwoman popped up...

oops,,,sorry, I am having a hard time focusing...back to story..

When I removed the lid of the trash can, I found a sack with clothes in it. Turned out to be the scrap material from the first American flag ever made...

darn, my appologies...it was really a sundress and a pair of clogs my female room (and bed) mate had discarded. I never had one CD thought up to that point in my life. Five minutes later, I was wearing the sundress and clogs...

everyone can figure out the rest of the story from that point in my life to current day.

I lived happily ever after, just like everybody else here...:D

:love::love:

[missyvf]

For me the first time I acted on my interest in wearing something feminine was when I was 12. Best friends moms panties.

[sweetjan]

My first memory was when I was in my 20's I tried on a pair of my girlfriends panties when she was not home. It all started from there.:o

[Vivian Best]

I can't remember my exact age, probably around 5, thinking I should have been a girl! That thought consumed me from that day on. I didn't have older sisters for a ready supply of clothing I had to rely on my mothers. They didn't fit until I was in my early teens but that didn't matter, I loved them anyway.

[Raynefall]

I probably started around 6 or 7 with some of my sisters clothing. Always had thoughts that I should have been a girl seeing as how I was the only guy in a pretty much all girl family and that includes relatives.

[helenejo]

I must have been about 5. It was one of my mums papery petticoats trimmed with lots of lace and red ribbons. I loved it.

[PinkLover]

i dont remember when exactly but i remember seeing a few pictures of me in girls clothes when i was a kid. didnt really care much at that time and to speak the truth , cant really remember. I officially wear bra and panties when i was 14 i think. i was all alone in the house. everybody is out working or school. so i tried my auntie's panties and bra. the bra was kinda troublesome at that time but i remember how lovely and soft is the panties is. it was rather a one time until im 20. where the urges comes back and i went to buy my first cami. never looked back ever since .. purged a few times but the lingerie stays .. :D

[GirlyBits]

I was about 9 or 10 and I was on a trip to Mississippi to visit some family and my cousin Breezy had dressed me up jokingly from head to toe with make up and all. I can remember that a smile never left my face. Its a memory that has stuck with me forever.

[rachael ann]

think it all started when i was 6. trying on my aunts bathing suit.