Childhood Crossdressing memories??

[Jenny22]

My earliest childhood memories go back to about age 5, and they are very, very vague. So, I can't help but wonder how is it possible for some to say they started dressing at an even earlier age and how their recollections can be so detailed at times. Could it be simply wishful thinking? Hmmmmm.
Your thoughts??

[wanda66]

I really don't remember what age was when I began to crossdress. I dunno I was young Preteens and I love to wear my mom's panties and bras. Actually crossdressing brought me to my first successful arousal. I remember thinking at the time what a wonderful feeling . So in my early youth Crossdressing and masturbation were one in the same, it was later in my teens when I found that crossdressing fulfilled a different need. Now I seldom become aroused with my cross dressing .

[Christie ann]

Very young. First grade, getting up in the middle of the night to put moms lipstick on. Woke up with bright red scrawl all around my mouth. I am sure I did a very credible 6 year old explanation. Things were better in later years when I was alone at home for a little bit before the parents came home from work.

[Lorileah]

Your logic is flawed. Many many people remember things from a young age. My first NON-crossdressing memory was when I was 3. My first transgender feeling I remember was when I was 5. I think most people here may not remember the first because after all, we don't tend to remember daily thoughts, but I will say many here have the first epiphany somewhere in the memory banks. I think it is rather rude to insinuate that members here are "wishing"

[Teresa]

Jenny,
Early recollections aren't wishful thinking I can remember clearly my early childhood when we lived in Malta .
As for Cding memories they are clearly imprinted but then they didn't start until I was 8-9 years old but then it all happened at once, girls, clothes and sex all became entwined leaving me with something that has me affected till this day.

[alwayshave]

I remember wearing my mothers merry widow which she kept on the stairs going up to the attic, the entrance to which was in my room. That is no older than 4 or 5. I have been hooked since.

[Sarah Louise]

I was four and I remember it well. My older brother suggested we try on my mother's tights and show our parents. They found it funny.

The next day, I decided to do the same, but this time my dad shouted "get 'em off" and I scuttled back to my bedroom.

It's still very vivid, even now.

[Milly1410]

About 5 or 6, for fun tried to put on my mother's bra and panties. It went on for a coupe of weeks, until she found me out, and was mad at me.

[BLUE ORCHID]

Hi Jenny:hugs:, I don't even remember what I had for Breakfast this Morning. ~~...:daydreaming:...

[Chelsea B]

I didn't put on an article of female clothing until I was perhaps 14 years old. From there, it picked up momentum pretty quickly and escalated to full dressing within a year or so.

However, I have very early memories, from age 4 (my earliest conscious memories) of utter fascination with girls and women, and the differences between us. Since the body differences were not under my control then, my fascination focused on clothing. It took quite a few years before I couldn't help but try them for myself.

Since then, I developed a very strong love of and respect for women. That has to have contributed to my love for dressing.

Update:

Whoops, I almost forgot. I was probably about 5 years old when my sister dressed me as Cinderella for Halloween. I protested vigorously, but thoroughly enjoyed it.

[Bailey420]

I can remember when I was around 4-5 years old to around 8, I had 2 female cousins who lived a town over who were around the same age as me. In fact our birthdays were so close that we shared birthday parties for a few years, lol. My folks quite often would drop me at my aunt's for the weekend, and the girls and I were very close at the time. I remember how I used to love getting dressed up in their pretty clothes and playing their girl games all weekend. My aunt never said anything, but would make me change if there was going to be anyone else around, or if we went anywhere. I also remember how much I admired how these girls could be so pretty and dainty one minute, then get invited to play some ball or go fishing, and simply transform on a whim. Just throw on a ball cap, jeans and sneakers, and go, and be every bit as "boyish" as the rest of us boys.

My uncle was rarely home, but he did catch me once and made a huge deal about it. He told my folks, and my dad absolutely flipped! Sadly, after that I wasn't allowed to hang with my cousins as much, and they eventually moved away and we lost touch over the years :(

[LacieMarie]

When I was very young I can remember wearing my sisters panties to bed with a shirt on over it. I remember my mom asking me why I had her panties on and I remember telling her I feel pretty in them. I was about 5 to 6 years old at that point remember the house the bedroom I was in. The brain works in ways and memory works in mysterious ways as well.

[Judy-Somthing]

Five dose seem a little to young to remember, I was eight in third grade and would under dress with the tights and Satin ballerina briefs to school.
If any of you older guys remember the clothes of the 60's had no stretch and the ballerina briefs were tight and had no elasticity like todays lycra.
How come girls always had tight fitting clothes and guys had loose? Even now a days.

[Diane Smith]

I have clear memories of my mom putting lipstick and nail polish on me when I was very small, after I expressed my curiosity about them while watching her do her makeup. Later, she told me that this was at about age 2-1/2. My first recollection of actually trying on something without adult help was when I was 5, but I was already quite the student of women's clothes, shoes and makeup by that time, and the switch had been thrown, so to speak, long before then.

- Diane

[aprilgirl]

The earliest memories I have were at age four, though I didn't start cross dressing until I was ten. Looking back, I do recall moments in between that were a sign of things to come, as I had an interest in feminine things.

[StacyCD]

My earliest memory is that of a conversation with my older sister about what to get my mother for her birthday. I suggested a bra--showing an interest in feminine clothes. I'm pretty sure my actual dressing began between seven or eight.

[Valerie Beards]

My earliest memory, which is very vivid was first cross dressing in my mum's clothes when I was about 10. I had for many years been fascinated/attracted by what women wore and what it felt like to wear. One day, whilst mum and dad were at work, I realised I could find out and went on tried on mums. The rest as they say is history...

[sometimes_miss]

Yup, mom dressed me in my sisters clothes when I was a toddler, supposedly to save money so I wouldn't ruin my 'good boy clothes'. It lasted a few years until my dad came home early for lunch and saw me still in a dress (mom would usually change me back to my nice boy clothes for lunch, 'dressing up for dinner' as she put it. Mom also would avoid getting my hair cut, using excuses like the bus came, or the barber was too busy, most likely to keep my hair long. Even with all that, I didn't get what she was doing; I never thought I was a girl at that point. That would all change; a couple years later, someone started dressing me up in his sister's clothing and molesting me, planting the idea in my head that I was really supposed to be a girl. That would go on sometimes every day for weeks at a time. Lasted until I was almost 14. So yeah, I was crossdressing a lot as a kid. By the time I hit high school, I thought I was gay, transsexual, I was really confused. I had attached dressing and behaving as a girl with the only source of affection I had. Sort of like Pavlov's dogs, I think the urge to dress up is simply connected to expecting affection; but now I do it whether the reward comes, or not. Apparently when something is drilled into you during certain periods of development, maybe you can't change it. That would explain a lot of things.

[Karen RHT]

Looking back, there's lots about my early childhood I don't recall clearly. I've often been told that I was very curious and adventurous as a child, but I only recall the details of a handful of those adventures. Mostly I recall fragments or generalities such as always having an interest in watching my mother, aunt, and other women apply makeup, fix their stockings, hitch up their half slips, etc.

My first time crossdressing was one of those adventures I do recall clearly but that's because it was Halloween and I spent a lot of time and energy assembling my costume. I was 11 by that time, and my mom and aunt provided everything I needed to dress completely as a young woman.


Karen

[CONSUELO]

I would agree that early memories of childhood can be vague or even incorrect. However in my case I have a very clear memory of the event that set me on the path of cross dressing. I could well be wrong about my age at the time but I know it was early in my life. Perhaps this applies to many of us cross dressers.

However, I strongly believe that the first time one cross dresses is such a powerful emotional event that it registers very clearly in our memory even though we might be a bit off as to exactly when it happened. So reading peoples accounts of their first time alway seems very authentic to me. For many of us cross dressers this is one of the most powerful and defining events of our young lives.

[Beverley Sims]

I have recalled early memories of dressing here in many different threads.

When I first started here I felt that my activity was minimal.

Much of my experience came between the time of eighteen and about twenty five.

When reading others experiences I can recall things that happened to me.

My earliest experiences were from the age of four to five when my nearest neighbours were girls about the same age as me.

Mothers and fathers, and tea parties were a favourite with the girls dressing me up as a visiting aunt etc.

The father was usually played by someone in absentia.

[Jenny22]

" I think it is rather rude to insinuate that members here are "wishing". I didn't mean to be rude, Lorileah. Please accept my apology. Ditto for others,if they thought the same.

[Confucius]

Childhood amnesia is supposed to take place when we are around seven year old, and as a result we lose almost all memory of our first 3-4 years. In my case, I have retained a number of vivid memories of my infancy, and these memories were somehow reinforced during my growth. I have memories of being in crib, using a bottle, certain infant clothing, and many incidents during my pre-school years. I recall making childish associations to make sense of my world.

In my case, my mother wanted a daughter when I was born. I mean she was bargaining with God to ensure I was a girl. When I was born, I was a disappointment. However my mother did not have to wait long. When I was five months old, my mother was pregnant again. This time her dreams came true and my sister was born. My sister was pampered as my mother's little princess. I grew up thinking that my mother would have loved me more if I was born a girl. I believed that all parents preferred girls, because boys were trouble while girls were sweet and obedient. By the time I was three years old I was raiding my mother's closet and trying on her clothes. (This did not amuse my mom, because I was ruining her good clothes.) I remember telling her that I was just playing "mommies". Somehow I was making my world right. When I was 4 or 5 years old my mother made me a dress for me to play in, but my father stopped that. My dress was given to a neighbor's girl, and I was forbidden from crossdressing..... Well, I never imagined that I was different. I believed that all boys secretly want to crossdress but we had to pretend that we didn't. The idea of male privilege was entirely absent in my childhood.

[Secret Drawer]

It seems that some memories, and for many here, crossdressing/gender expression ones, make especially deep impressions on us. I do seem to recall very early childhood crossdressing/experimenting experiences. Hard to say what age, but certainly single digits. Other memories are a bit less clear, but random "moments" still pop into my minds eye. I have a feeling that for many of us here, varying "milestones" of gender expression are quite clear in our minds. I recall many different crossdressing experiences like they occured yesterday that happened 30 years ago and more. I even seem to recall moments that I was strongly envious and frustrating moments... I take the good with the bad I suppose...

[Stephanie47]

I have to agree with Lorileah on whether anyone may have memories of a really young age. When I was three years four months old our family moved from a grandmother house to an apartment. The house had just too many family members living in a post World War 2 environment. Anyway I can recollect several things I had done, such as riding a tricycle on sidewalks which were large slabs of slate. And, tearing wallpaper off the wall and putting it into a little dump truck. I don't think my grandmother was too happy with that. I also remember looking through a sliding door at a Christmas tree which would have been when I was two years four months old.

Now I'm going to throw a monkey wrench into the conversation/thread. As a very young child between three and four years old I had recollections of myself lying dead in a snowbank attired only in a full slip and panties. Don't ask how I could have had visions of such a thing. We did not have a television set yet. There was nothing at all which would have stimulated that idea, which still persists. I know once a person thinks about something it may persists forever. I've also thought with some degree of hindsight this was a reason for my love of pretty nylon slips. And, this memory totally predates any interest in women's clothing which did not kindle until puberty.

I know I mention awhile ago that living a past life may have a bearing on how a person develops in the current life. Someone on this site said it was a bunch of bunk. She may be right. My wife is in the past lives believer camp or at least does not discount it. Anyway, I just throw that out for consideration, because I cannot reconcile some horrific vision with a three or four year old boy of 1950-1951. And, back in New York City in that era there were maybe fifty murders a year and most were family related and not random.

[Tonya Rose]

For the first time ........ I have to agree with Lorileigh ! Here! She nailed it!!!!!!

[Tricia Lee]

There exists photographic evidence of me, somewhere between the age of 2 and 3, simultaneously wearing a pajama top, holding a toy rifle, while standing in my mom's red slingbacks with a 3" heel. I need to find that picture.

I don't remember that specific event, but some of my earliest memories are trying on shoes in my mother's and aunt's closets. This was all well before the age of 5.

[michellechong]

I vividly recalled my first time wearing a red panties picked up from the ground just outside my classmates's flat, the moment I slipped the lingerie on, I had an instant "release" and this kick-start my journey into crossdressing and beyond. From just panties, I progress to bras, panty hose, dresses, make-up, heels,....Initially I wore my elder sisters" lingerie and clothing, eventually I stole from the cloth-line in my neighbourhood. This went on for a few years till I was finally caught by a man who trailed me into a forested area, waited for me to dress up, before approaching me. This lead-up my progression beyond just crossdressing.

[TrishaTX]

I see your point, usually what we remember is what is reenforced by someone or something over time if it is before the age of 5. I remember very little to be honest before that age. I remember after of course, especially my mothers's night gowns...and that is still my favorite thing to wear.

[karen inside]

Jewelry...that is my earliest memory! I was an oops baby, parents and only sibling were MUCH older and my brother would take me around in his car while visiting his girlfriends (i must had been 5, he bought a car-so he was 17). One of the prettiest , I remember her well, she wore ankle bracelets, lotsa rings, so after a few times visiting her, I wanted to be like her and crafted my own jewelry. Mom saw me wearing it and I think that was stopped by her as she knew dad would have exploded! But within a couple of years things progressed to under garments...naturally! Whether mom knew or not, I don't know-she never said anything.

[ShelbyDawn]

I have verified memories through other family members of things that happened when I was three or four.

My earliest crossdressing memories are about five; I would steal my moms slips and panties from the oldest of my three sisters who was a year younger than me.
Quit wearing my mom's slips in grade school but continued to "borrow" my sisters panties into high school when my mom started buying me men's bikini briefs.
I don't remember ever asking her to buy them and she continued to buy my brothers tighty-whiteys so I think she knew about my little habit...

And I will admit that my sisters panties continued to get 'accidentally' mixed in with my briefs until I left for college.

[Julie Denier]

I remember clomping around in my mom's heels as a toddler. Later I experimented with pantyhose and other clothing. Once, as a grade schooler, I played dress-up with my younger sister; Mom came by to check on us and I tried to change quickly. I think she saw me partly dressed up but never mentioned anything about it. After that, I made occasional forays into my mom's closet. For a while, her shoes fit (size 11) but I outgrew them quickly ...

[Eryn]

I remember a few things from that age. I remember finding that it was great fun to draw on the side of a bookcase with a pencil and pen until an adult happened by. I also remember being at a community dance at age 4 and making the mistake of asking another boy to dance because I didn't understand gender roles. I clearly remember the lesson I was taught by their ridicule.

As far as dressing, I did some experimenting with Mom's hose and lipstick, but was always very careful not to get caught. By that point I knew that what I was doing was wrong in the eyes of everyone but me.

I had no sense of being a girl. I knew I was a boy and that was incontrovertible by the standards I had been taught. It was much later in life that I finally figured out that I could be me regardless of birth gender.

[Cara Lacey]

36-2-29 That was my locker combination in grade school.
Some people have better memories than others.

My very first memory was getting caught at my Mother's dressing table, with bobby pins in my hair lipstick on my face . This is very early on in my life. I could not understand why everyone was so upset because I saw my mother do this.

My second memory is my dad's 49 Studebaker catching on fire. I would have to have been about 3 1/2 years old when this happened, because my dad bought a brand-new 58 Ford in September of 1957.

When I was about five, I remember getting caught in the basement with the kid across the street, trying on my sisters dresses.

And from the time I started second grade up to high school, I wore my sisters panties to school on Monday Wednesdays and Fridays, because those were the days I did not have gym.

[NANNETTE]

I had an interest in female clothes and the desire to want to be a girl from early childhood. I had a deep interest in stockings and tights. My first crossdressing experience was unsuccessfully trying on my mothers stockings at the age of six. Four years later at the age of ten I was visiting my girl cousin who was four years older than me and I begged her to dress me up as a girl in one of her dresses and tights. She had just started to wear tights/pantyhose and I was extremely envious of her. I don't think she wanted to go down the road of giving me a pair of her tights to wear but she did dress me up in of her dresses and she and a friend put make up on me. As soon as I was dressed I adopted the persona of a girl and loved it. The most significant event came two years later when I at last tried on a pair of my mothers tights. I wasn't sure if any of her skirts or dresses would fit me so I just wore the tights whilst wearing a boys sleeveless jersey. It felt so right I could not believe how girly my legs looked. The following day in school I could think about was my first time in tights. It turned out to be the first of many times. Thereafter I wore my mothers tights whenever my parents were out. Still not confident in trying on skirts and dresses I wore the tights with my football shorts to try and emulate the look of a girl wearing hot pants which were in fashion in 1972. A few months later I experimented with my mothers skirts and found to my delight that they fitted me. When I got to the age of 20 I further progressed to my mum's dresses, the feeling was awesome. When I got to 21 I began to pluck up the courage to buy my own hosiery, which opened up a whole new world for me as the style of tights that I bought was more appropriate to my age group. I loved black tights and also white tights and coloured hosiery was also very much in vogue in 1981.

[Jessie29]

When I was really young (3 or 4) I wore my mums heels and fell into a table. Got a scar from it - an ever lasting memory of who I am

[Lorna]

Having no sisters or close female relatives, the only clothes available to me were my mother's. I was in my early teens before I tried anything on and, by then, my height and weight were not too different from hers. What surprises me is the experience of many contributors who wore their mother's things when as young as three or four. For me it would have been impossible: everything would have been very much too big and wearing her clothes in any meaningful way would have been impossible. Her stockings, for example, would have been longer than I was tall at four years old!

[Nine]

Before being 6, Ive received an electric train for Christmas. That was what I wanted and so happy to play with.
My mother was happy to see me not playing anymore with the dolls of my sister. Happy to have a little dude.
Some months after I went to the doctor with her. He told me I was not a girl and I had to stop to wear the dresses and skirts of my sister.
I didn't touch anymore this train after that, but I still get it and I am still what I am.
I don't have so much memories just I liked to wear dress and skirt. That's what I remember of, not really pleasure.

[Jennifer in CO]

photographs help with memories quite a bit...jogging the brain as it goes. My earliest "memory" is a photo of me in a shorts set/romper that was my older Sisters (primrose yellow and very girly). No memory of that event...I was maybe 2 or 3. Do remember even without the movies several Christmas mornings and one particular where my Sister and I come out of the hallway wearing similar flannel gowns. Two seconds later the camera stops and next frame I'm wearing a long blue robe that covered the gown...except the lower 3 inches of ruffle...Several other times I remember being dressed in my Sisters clothes. Don't remember why, but starting at 10 when I went to my Cousins for 3 weeks and spent all of it in her clothes I remember that like it was yesterday. Course, I was writing a diary by then as well so it was easy to remember. When you write something down, it usually becomes ingrained in the mind...the good and the bad...

[Adriana Moretti]

When I was a kid my one of my favorite places to play was my grandmothers walk in closet in the basement ( it was really its own room) it was loaded with my mothers, and my 2 aunts old clothing, and on the top shelf had a colection of all their wigs from beauty school....I played in this room for hours trying on dresses and bad polyester pant suits LOL....and besides that room..my grandmothers bathroom had about a 10 foot makeupcounter and mirror....i would lock myself in the bathroom and play with the makeup too ! xoxo

[Sara Jessica]

What I am able to recall in my mind's eye from before age 5 is like snapshots and there are certainly a handful that relate to dressing up to some extent, whether mom's clothes or my friends (playing house, I was somehow always the little girl). Yet at the same time, the feeling of being transgender was pervasive in my earliest memories, much more so than acting upon those feelings by dressing up.

[rebecca_ns]

My first memory is at age 4. My cousin who is only 10 months older than I, was having nail polish applied by her mother. I said that I wanted some too. My aunt looked at me and said sorry, we don't have any blue nail polish. I replied "but I want pink, like Jo Jo". I was told very sternly that boys do not wear nail polish. That was the beginning of the shame game for me, and the beginning of compartmentalizing and burying this part of my personality.

[AKADonna]

I remember checking out my Mom's lingerie drawer when my parents went out on Wednesday night to play cards. I would put on her bra nd stuff it with socks or tennis balls and prance around the house! She noticed that her things had not been replaced in her drawer properly and one night, I found a new Playtex bra in my size under my pillow with a not that said, Now you have your own, please leave mine alone! Nothing else was ever said, but I still wore that bra until graduating from High School!

[dawn-sussex]

My earliest memory was watching my older sister at her dancing classes and asking her to dress me up in her yellow dancing tutu which she did - this would have been shortly before my fourth birthday. I remember feeling really pretty as a ballerina and asking my Mother if I could go to dancing classes like my sister. Unfortunately it was "for girls only"!

[Hazel King]

I found a corset belonging to an aunt who lived with us, when I was about 10 it was far to big but it felt good, later I found some nylons the rest is history, the same aunt would polish my nails with a pad thingy and tell me my hands were wasted on a boy

[Kiersten]

I was 6 or 7 when i had My first significant memory I recall. If there were any other signs earlier then that I can't recall.

[Sister Rachel]

I remember very clearly. I must have been three or possibly just turned four. I looked in a bedroom drawer and found a pair of my gran's knickers, green lace-trimmed (in some kind of artificial silk ?), immediately put them on, felt wonderful, so wonderful I started bouncing up and down on my grandparents' bed gleefully, was discovered by my granny. Definitely NOT wishful thinking, it's one of my clearest early memories.

[deirdre travesty]

At about 3yo (1946) my Mum put curlers in my hair. Hated it. She was preggers with what turned out to be my first sister
She tried to explain that my girl cousins had to do this but I was not impressed. She had made some curtains and had used a few offcuts to make a little dress. I didn't want to try that on either.
She may of suspected that she was going to have a baby girl and was awash with fem hormones.
Now.... if only she was here to do it again and I still had the hair to do it with.

During primary years at an all boys school some of us smaller "pretty" boys had to dress up as girls for an annual concert and
dance with the more macho taller lads. I remember that my partner had roughish hands. I don't know why he had rough hands. In later years he became a lawyer or accountant or engaged in similar villiany . Definitely a profession for soft hands.
I was decked out in a mid calf length blue ball dress with a red cherry broach attached. In my memory......... very pretty. Sigh.
The women charged with our make up didn't seem to notice that we were all wearing our black boy shoes and long dark school socks.
When we went onstage we wondered why the audience was laughing. It was not supposed to be a particularly funny role. Or so we thought . We had practised the waltz routine for weeks to get it right.
They, of course, were at eye level with the footwear and our chunky boy legs. Very droll minister.
The gender change role did not, at the time, seem to be significant but when I collided with puberty a few years later I started "borrowing" items of female apparel.
Was that the result of the seeds sown back in 46 and 53 and the other chinks in my masculine charade ?

[LookingGlass]

I remember when I was young, about 7 or 8, my favorite shorts were these red ones I later found out were actually girls' shorts. We briefly moved into my grandparents' house when we moved to the same town. Lo and behold she had a dresser in the room I used that was full of young girls clothing she saved from when my mom and aunt were kids (the one time her hoarding habits paid off). Bras, pantyhose, stockings, all kinds that were still in good shape from what I could tell... fun nights sleeping in them underneath my PJs!

[Petra1]

I didn't start til I was about 12 years old. And it had more to do with my fascination for breasts and wanting to experience different things while wearing them. It started with borrowing my mom's bra and stuffing with washcloths and wearing them under my regular clothes. At that age, there was definitely some sexual excitement from dressing.

Before starting high school, I spent the summer visiting my favorite aunt. While she was working, I was home alone. That was some fun to be had.

In my freshman year, I stopped going on the family weekend camping trips because I wanted to stay home and spend the weekend dressed.

In the beginning of my sophomore year, I joined an organization that had a spirit week as part of its initiation. One of those days, all initiates had to dress in drag. When I asked my mom for a bra, she told me she didn't have one that fit me. I had to keep my mouth shut so as not to disclose that I had already been wearing her bras so I ended up having lopsided boobs all day.

That was the same year mom got divorced from her second husband. We moved. Mom ended up working nights. After the siblings went to bed, I would throw on a bra and and stuff wth towels (instead of washcloths because I wanted bigger boobs) under my regular clothes and go bike riding in the dark, around 10pm. One night I went about a mile and a half one-way.

I don't remember if it was that year or the next that I first dressed publicly for Halloween. Mom had an old sleeveless mini-dress, that I stuffed with towels, and a pair of pantyhose. I remember her telling me the boobs were too big so I used washcloths, until she left. Then I went back to the towels. I also took off my underwear and wore only the hose ( the dress was long enough to cover up the boys). Stayed home and passed out candy. Got compliments from a few women. One even said I was the cutest one she had seen. Later took my little brother trick or treating while I was dressed.

Actually, the only times I ever dressed publicly, and actually allowed people to see me dressed, were for Halloween. The second time was in college. The third time was about 9 years ago, again, staying home to pass out candy. The wife wasn't too keen on me leaving the house and didn't like it when a group of kids came back a second time to ask questions because the first time they thought I was really a woman, albeit an ugly one, until I spoke.

My wife has seen me dressed several times but I've since backed off dressing in front of her. When we were dating, she thought it was exciting to see me dressed but I think my wish to sometimes be more realistic has turned her off the idea. Once in a while, I'll trot out a new outfit to model but for the most part, I try to be the man. She says she doesn't mind but I'm not sure.

And now that she's not working weekends anymore, my time is limited. Pretty much only when I stay home while she's working.

[ashley-fl]

I can remember being 5, because i was in kindergarden, and putting on my sisters panties instrad of mine. I had a babysitter that use to dress me as a girl in order to punish me for being bad. Needless to say I was a horror to her.

[Jacqueline1965]

I was between 3 and 5 years old not sure exactly how old but I have a very clear picture in my mind of my mom and my aunt trying on clothes at my grandparents house. They were walking around the house in their panties and bras. It is one of my earliest memories and soon after I tried on my mom's panties for the first time. I was definitely caught at least once and scolded but nothing really happened. I continued to be fascinated with her underwear for several years....after my parents divorce when I was almost six my mom remarried within a year and we moved. She had this NFL football throw pillow that she was making me and she stuffed it with her old panties and slips. Of course I found this and used the items to dress up in at every turn. I also used to wear her panties, bras and slips when she was out..this was all before junior high school. I was pretty advanced for a pre teen kid. I was always envious when we would go shopping and go through the lingerie dept. I wanted those pretty panties and lingerie in the worst way but couldn't let on. I also used to borrow my step mothers panties when I would stay at their house. She had the sexiest panties I had ever seen. This went on for a while until she busted me wearing them under my robe, I was 14! She then discovered all her missing panties in between my mattress. I was sooooo embarrassed. We all had a little talk about privacy etc...and I promised never to do it again. They chalked it up to teenage hormones...but I just really loved wearing her panties. Finally into high school I was able to mail order panties to my house discreetly because I was home alone usually when the mail arrived. I also had a GF in high school that let me wear lingerie when we did "stuff". Once I got caught and just said that the panties belonged to my GF. Whew!

[Angie G]

I think I started at about 10 or so.Well it's been better then 50 years now.:hugs:
Angie

[Ally 2112]

About 11 years old i had urges before and was able to resist for a while .One night i was whatching Happy Days no one was home i went to my mom;s closet and tried on one of her dressess it has not stopped since

[Geraldine1947]

I started dressing at age 13 in Mother's and Grandmother's underwear and dresses. They went out shopping every Saturday leaving me alone in the house. I would raid the washing basket looking for femme clothes to try on. I especially loved Grandmother's longline brassieres and corsetry. Once i had put on stockings I was addicted. Xxx

[SaraCro]

When i was young i always dressedd in some heels and nylons than later bought flats and while was alone at home just enjoyed walking around the house!

[Fiona123]

I can remember when I was about 8 yrs old & trying on a girls swimsuit. I was a crossdresser ever since...

[PattyT]

I don't have any crossdressing memories as a child. I know that I wanted to dress in female attire ever since I can remember. I guess I started trying on my mon's shoes when I was in junior high school and started dressing in closet in high school. This opened a new world for me. I have been hooked ever since.

[Lily Catherine]

Twirling almost every full skirt I wore when I was 11 or 12. I still like to twirl my skirts nowadays, but the effect is less obvious on my skirts now - they aren't as full as those I wore a decade ago.

[NewBrendaLee]

I remember when I was about 5 or 6 putting on some of my moms old dresses and wishing that I was a girl

[dana digs sweaters]

Too many childhood crossdressing memories to list.
Was enjoyable growing up.
One of many reasons to continue full on crossdressing as an adult.

[abby054]

I have three distinct incidents in my memory from age four, my earliest memories, none of them CD related. I went to live for a year with my grandparents the week after my fifth birthday, so I can date things pretty well at that age. I have many memories from that year, including my first CD questions after I met the twin sister of a friend. She was dressed in all the frills that mothers in mid-America dressed their little daughters back in 1960. I remember asking myself why I could not look like that. I asked my grandmother and my aunt, but I do not remember their response. Knowing them well, I can easily and accurately guess what they said, though.

My first dressing experience was age nine, a Halloween parade. Yes, I dressed in public before I dressed in private. That is probably why my parents set an age limit of ten for trick or treating: after two consecutive halloweens of my dressing as a female, they probably wanted to stop it. It did not stop. It merely went underground and started occurring year round.

[Georgina]

Somewhere between 5 and 10 I discovered my mother's slips. That was all I wore for a few years.

[jeanieinabottle]

The memory is quite vivid except the age which is approximate but close. I was probably around 3 1/2 or so to my best estimation. But I clearly remember wearing an emerald green dress. It had a thin white piping around a collar. The front was vertically pleated, buttoned in the back and also tied in the back with a big bow. I remember the scratchiness of the slip producing the poofiness of the skirt, the shininess of the black shoes, the lacy ruffles around the socks and the bow clipped to my hair. I remember standing on our dining room table and looking into a very large mirror on the wall above a buffet and people telling me how pretty I was. After that I remember a yellow dress, a black red and white plaid dress. I remember being in a store with 3 angled mirrors and trying on dresses as I looked in that mirror again probably around 4 or so and at least once riding the bus home wearing a dress that was bought at the store (don't know if it was paid for?). I dressed as I pleased at home, played boy things but also had tea parties and played with dolls dressed as a girl. Then at age 5 I remember my kindergarten teacher scolding me for wearing a dress from a trunk filled with clothes for "dress up" play in the class. There was a little kitchen and I thought I could be the Mom. I was firmly told (scolded) by the teacher that as a boy, I shouldn't dress up as a girl....it was wrong. She called my parents into school and I got the lecture that boys wear pants and girls wear dresses even though prior to that time, there was acceptance. Maybe time to become a boy for once and all. So for nearly 60 years I dressed in secret, held that secret tight, lived with shame remembering my kindergarten teacher's scolding until 6 years ago. Came clean to my accepting wife. Life is now beautiful, peaceful and enjoyable. Too bad, at this point in my life it is also much shorter.

[RobynC]

My earliest memory was at 10 years old on Halloween night. I didn't have a costume, so my older sister and mother dressed me as a girl. I remember as I was going around collecting candy, boys were wolf whistling at me. It made me feel special and that I was missing out on something? Before that I enjoyed playing with my sisters house and dolls, over playing with my toys. I didn't dress then and when dad caught me playing with my sisters things, the roof nearly came off the house. I never enjoyed, as a kid doing boy things. Never played baseball or joined the Boy Scouts and when we went to someone's house and the girls were playing with their things. I cried because I was being left out.

[Imeni]

Oh hell, I must have been like 3. I was old enough to walk around the house and not be constantly looked at from my parents at all moments. I was a pretty good kid, I knew what was bad and didnt do it. I had freedom. I remember one day, sitting on my moms bed while she was doing something in her room and when she opened her closet, some sort of white floral dress, it was silky but not actually silk. I was like, I need to wear it. I dunno why, I don't think there was any good reason. So when my parents had company, i scuttled away and put it on, draped in fabric. I waddled outta the room, all the adults laughed. The next few times I tried, i got in trouble. After that, I kept it a secret. Now, as an adult? Eh. Some people know i do it, but not my parents. I dont feel like having to deal with that bag of issues.

[Suzy Parker]

Way too many memories to list. Very fond memories starting about the age of five. No sisters so I dressed up in moms clothes whenever I could. I can describe her wardrobe in great detail. I was in heaven when I reached the age when she would leave me home alone. She would call and check in on me from work asking how I was doing and I remember replying "Fine" while in her dress or skirt and blouse. Mom had nice things and I explored all of it.

[CarlaWestin]

Of all the assorted bits of memories, the CD start point was possibly in pre-teen when I liked to venture out in the quiet, safe suburban night to the park. One night I thought it was scandalous that I was wearing a jean jacket, a white t-shirt and mom's bra stuffed with socks.

[Lacey New]

I was in my early teens - 13 or 14 in the days of the miniskirt. So every now and then the girls in class would provide and discreet peek and like most young boys I was fascinated by what I saw. I had a sister a year younger and on occasion, she would leave her panties in the bathroom. Temptation took over and soon I put them on and you can imagine the rest. Well, it became more thrilling to try more and more items of lingerie and well, the rest is history. Here I am more than a few years later still enjoying the same things.

[Virginia1983]

Way too many memories to list. Very fond memories starting about the age of five. No sisters so I dressed up in moms clothes whenever I could. I can describe her wardrobe in great detail. I was in heaven when I reached the age when she would leave me home alone. She would call and check in on me from work asking how I was doing and I remember replying "Fine" while in her dress or skirt and blouse. Mom had nice things and I explored all of it.

I completely identify with you and love Secretes in Silk! My sister would play dress up and I always wanted to play too. I was completely fascinated with lipstick and lingerie by the time I was 12 or so. Loved my mothers slips, girdles and peignoirs!

[RobynT]

The earliest memory i have is, when I was 6 or 7, and fantasizing about a classmates yellow dress. At the time I had no idea why I was so fixated on that dress, and it wasn't until my preteen years that i got very curious. Lots of time as a latchkey kid to explore in the afternoons after school, and was only caught once by my dad...(don't think he believed the excuse given, but was never spoken of again). Its funny, how you stick to certain things, I still have a great fondness for the classic maidenform type slips and girdles from those days. I guess old habits die hard..

[Karine]

My earliest memory of crossdressing, or more accurately of wanting to crossdress, was in my early teens. I already like heels and wanted to try some. One of my aunt had left a lot of her old heels at my grandmother house. Unfortunately, i have never found some time to try them on since the house was never empty. However, later, I knew (I saw pictures) that when I was 3 or 4, my older sister used to dress me up as a doll for fun. But I have no memory of it.

[sara66]

One of the earliest memories I have is putting on mom's bra. I had to be 4 or 5. When I was about 9, mom walked in on me it the bathroom wearing me sister panties.( white with little yellow dasies)
She just said take them off. only time i was ever officially caught.

[maya1love]

I had the opportunity to dress as a girl in private and then out at Halloween. I talk about my experience here: http://www.crossdressers.com/forums/showthread.php?229580-Did-your-Mother-dress-you/page3

Happy to chat with anyone about the experience!

[Virginia1983]

For Halloween in 5th grade I convinced my mother to allow me to dress as a girl - red lipstick, blond wig and a princess costume. I always dressed for Halloween after that and the dressing really took over in my teens. Of course it helped that so many New Wave bands and Boy George were crossdressing. In high school my friends and I would go to a gay bar in the city to dance. Drag shows were are BIG revelation to me and before too long I was going out dressed. My mother caught me so many times dressing or seeing boys that she just gave up and accepted it, before later embracing me for who I am.

[Dana44]

I remember a lot when i was young. I did get in my moms stuff and wore them. I remember my sister and I doing that LOL, guess we both was interested. But most of all I remember that I would suddenly switch and did not know what that other thoughts were and why. It took me years and interestingly I did have sex with older boys and I was always the female side of it. But we had being men beat into us by our parents and society in general. When I was married to my first wife. I did crossdress and we went out to dinner together. I was nineteen at that time. Then I spent later years in business. But it took me a long while to know that I switched from male to female and back again. Both sides of my brain are open and operating giving me creativity in art. But in my forties, I went to a holistic doctor and he tested my hormones. When I went in he said that I was female. My progesterone was at eighty percent and my testosterone was low. But I always been sexual and had no problems. But as I aged and the estrogen from foods and other stuff came into me I started to change and now have B size boobs. According to one DES doctors site, the only hormones that we should do is estrogen. Testosterone seems to not be good for us and when he gave my that my prostrate BTH went up and I had to get off testosterone.
So now I know what I am and, heck I am what I am and love it. I am still sexually hot. Male/female is a natural balance for me.

[Majella St Gerard]

When I was about 11 or 12 I tried my on my sister's school uniform a couple of times but never did it on a regular basis. I didn't start dressing until much later in my 30's.

[BillieJoEllen]

I have so many memories of me in girls clothing (mostly panties and tees with a ribbon). Being used as a dress model. Being forced to don girls clothes when I got my boy clothes dirty, wearing a dress for Halloween. Thing of it was I had no inclination to dress at that time even though I always considered myself to be a girl. It wasn't until 5th grade that my curiosity was piqued about girls clothes. I don't know that I would CD today had not a set of circumstances set off a chain of events that stimulated me to start CDing.

[Sandra_tv46]

Loved your story of your beginnings. So similar to mine it's eerie.

[Lily Catherine]

Not directly impacting me until I was a teenager: crossdressing used as a form of punishment and later hazing.

For one, a few boys in my primary school were changed into the female uniform due to violation of dress code - I recall it was hair length - and made to stand in front of the whole school. I did wonder what it felt like to wear a pinafore in place of shorts, but in context I was better off not knowing.

What I reckon sparked me when I was 11 would probably have been the Chinese dance troupe (all girls) with their beautiful dresses that had long, flowing skirts. I wanted to wear their dresses, and above all to look as pretty; as elegant as they were. There was one such outfit at home, although it was more formalwear (on the level of evening dress) than a specially crafted dance costume.

[NancySue]

Ah yes, I remember it as if it happened yesterday. I was an only child. Our next door neighbors had two older daughters with whom I often played. I was 6. One day they were playing "dress up" and asked me if I'd like to play dress up too. They put make up on me which seemed OK. I remember how makeup made me look and feel...feelings I'd never felt before. Then she gave me a pair of her panties. I was really beginning to enjoy this. Next, she gave me her pantyhose. I remember struggling to put them on. She helped. It was then that I experienced such wonderful and feelings and sensations. Next she gave me a pair of high heels which fit. And finally a cute yellow sun dress. She smiled and said that she forgot to give me a bra, so I took the dress off and put the bra on. She stuffed the bra with Kleenex. I put the dress back on. That started it all for me. Needless to say, we played "dress up often. Nylons of all kinds are my #1 love. Yes, I continue to enjoy myself. The wonderful feelings of peace, femininity, and sensuous continue to this day. I've come a long happy way. Love to go out and shop or just walk around.

[bettyloop]

My friend really liked dressing up in his moms clothes and always wanted to play house. I hated it back then, but now I love it!

[Robyn2006]

I was clueless until I hit puberty at 14. I knew I was a bit different, but it took a hormone surge for it all to come together. I had always loved looking at glamorous women, but hadn't yet realized that I wanted to be one. Once I did, I began to raid my sister's and mother's things as often as possible whenever alone. Of course, I was scared to death as I did it all... so frightened I'd be caught and that there was something really, really wrong with me. But to topic, the most memorable day occurred a few months after this discovery.

It was a Saturday and I knew I'd be alone for the day. I so remember the night before laying in my bed and thinking about the day to come. When it did and I was completely alone, the fire within me took charge. Fast forward a few hours and there I was wearing pantyhose and this wonderful, red flower dress of my mother's with one of her full, black briefers underneath that I had stuffed full with nylons to fill its 38D cups. Then as naturally I think as any young girl would, I began to put on my makeup. Of course, I hadn't any idea what I was doing but seems I got the important parts right... in particular, my mother’s red lipstick that I so loved to put on. Back then, I had long blonde hair that made my transformation complete as I brushed it into place. When as fully feminine as I was able to manage, I was so amazed at the young, beautiful girl staring back at me in the mirror. For that wonderful day, I walked through my home as the girl I so wished I'd been born... Scared to death, trembling with each new stroke of lipstick, but in complete and total heaven.

[dana digs sweaters]

Nice story Robyn.
Love the description of the planning the night before too.
Thank you for sharing.

[Angie G]

For me it was around 10 years old trying on my aunts shoes. And they didn't fit way to big.:hugs:
Angie

[Judy-Somthing]

Yes it's hard to remember when you first started cross-dressing but when my sister dressed me up and took a photo at 8 my road to cross-dressing started.
yes a wig would have finished the outfit much better.
She dressed my two brothers also. one cross-dressed with me for a few years and went GAY and the other never dressed with us!
http://www.crossdressers.com/forums/attachment.php?attachmentid=263071&stc=1

[Maria 60]

I sometimes think back and have many memories of my youth, but for some reason for the life of me, I can't remember the first time I tried on a pair of pantyhose and why I did try them on.