First time, thought I know it's been done to death

[Robyn2006]

Lately, I've been thinking a lot about that first time I knew things were different for me, back on a particular day when I was a 14-year-old kid and found myself privately exploring my family's bathroom and all that my sisters and mother had lying about. There, and almost instinctively, I put on my mother's bra and stuffed its cups full with toilet paper, then put on one of my sister's blouses she had hanging up. But it was what came next that changed everything. I opened their makeup drawer and took out one my mother's lipsticks: Avon's Periwinkle Pink, though it was more of a coral red and would be my go-to for years to come. Anyway, it was the first stroke of that lipstick that changed everything for me. With my mother's bra holding everything just right, I fully put on that lipstick and couldn't believe the girl I saw in the mirror. On that day, with that lipstick, I discovered a new person inside I never knew existed.

I'd love to hear your account of when you first discovered the woman inside.��

[Rachelakld]

5 year old, wanting to ride my 9 year old sisters bike, but didn't want people seeing a boy on a girly bike, so decided to borrow sisters dress and be a girl on a girls bike.
All down hill from there (we lived on a hill and getting the bike back up the long drive was difficult)

[GretchenM]

Great story, Robyn. I love your phrase, "I discovered a new person inside I never knew existed." That is actually so profound because it has now been shown that our motivation to dress is due to the existence of that identity that comes from the way we are configured rather than it being simply a choice we make. But seeing the essence of that undetected identity probably triggers what is maybe a predisposition that is the foundation of the identity. And the rest just follows along with each person experimenting and finding what works best for them. The same process occurs in the development of a cisgender identity; it is just that they do not have that other pattern that many or even most of us do. Completely normal.

For me I was about 7 years old when I had a desire to try on some of my mother's clothes and makeup. I do recall that the desire came first followed by the action. Unfortunately, that was 1952 and I got caught at a time when doing this was viewed as a very serious mental illness and not even remotely possible of being something natural built into some of us. Did getting caught stop me? Not at all. I did create the shame and fear that I was crazy in some way. It was 60 years later when I surrendered to the female-like identity and realized, with the help of a therapist, that it was just the way I am. The last 11 years have been, in this regard, the happiest years of my life. Socially still a challenge because of the lack of full acceptance in our society, but fulfilling for me as the real person I am.

[alwayshave]

Robyn, I'm glad that you have such a vivid memory of the first time you dressed. I started dressing at such a young age, 4-5ish, I cannot recall what I first wore. Though, I believe it was my mother's Merry Widow.

[Stephanie47]

My first foray into wearing women's clothing was taking down my mother's white full slips from the drying clothes line in the hallway of our apartment or off the drying rack that hung from the ceiling over the bathtub. I had no thoughts of being a girl. I just loved the feel of the nylon. Like Gretchen it progressed during the 1950's and 1960's when such activity was perversion and society said men wearing dresses were homosexuals. I lived in fear of getting caught and shame and disgust for what I was doing.

[CrossKimmy]

I must have been like 7 or 8 when I discovered that I had a fondness for feminine things. I snuck into my moms drawers and found these two pretty tule skirts in neon green and neon pink. I just had to try them on so I did and played ballerina. I loved it so much I kept them in my own drawer. They were quickly found and I was scolded.


Then again when I was a little older I was discovering things like underwear and lingerie in her drawers and took a great deal of liking to them and wore them whenever I was left alone. I progressed to clothes like dresses and skirts fairly quickly.

[JulieC]

For me, I was really too young to understand what I'd just discovered. I was 5, and possibly younger. I'd watched a scene on a TV show where the heroine was tied up and on a conveyor built. I was entranced with how she was dressed, and later that night I tried hard to corkscrew myself into the same tied up condition she was in, just to feel a bit like her. Not to feel tied up, but to feel like her. A few years later, I tried on my mom's pantyhose for the first time (and definitely not the last!). I was absolutely hooked. I could not believe how I felt. My crossdressing has evolved over the years, but I never feel complete without my pantyhose on. I'm sure that's tied into my first actual dressing experience.

[Maria 60]

For myself sharing room with my slob sister and seeing those biege pantyhose on the floor and the white short half slip was my breaking point. As you said all down hill from there but what a crazy ride.
Something about that slip and pantyhose combo.

[jacques]

hello Robyn,
First time I was not trying to be a woman, I was trying to be Robin Hood and put on a pair of my sister's green tights when I was about 7 years old! I discovered the Crossdresser inside!
luv J

[Sometimes Steffi]

I was about 12. I was old enough to be left alone when my parents went out. I was also old enough that all the equipment worked.

My parents went to a PeeWee hockey game that my brother was playing in. I knew that they would be gone about an hour plus travel time. After they left, I went into Mom's room and grabbed one of her panties to try on. Let's just say that I got aroused, as soon as I got the panty half way up my calves. It turned out to be the first of many times borrowing my Mom's lingerie.

[sometimes_miss]

At age 6, a bit before my 7th birthday, I'm now hanging out at my sister's best friend's house after school, because my mom has gone back to work (Sis's friend's mom doesn't work, and lots of the neighborhood kids hang out there. Seems a safe place for me to be, my mom spoke to her mom and gets the o.k.). Sis's friend's family is huge. Her friend is the youngest of seven. The oldest sister has three daughters, the oldest one only a year younger than me. So I play with them after school until one of my parents comes to get me. Now I'm part of a girl clique, albeit a younger one. At least no one's beating me up.
One day, sis's friend's older brother comes home and sees me playing with dolls with the other young girls, I guess looking not all that happy. Asks if I want to go play stickball. I tell him I don't know how. He says he'll teach me. I jump at the chance. We go outside, he teaches me how to hit a ball. Not an easy trick with a kid who's never done it before. He's nice to me. Treats me like a kid brother, over time teaches me lots of things that an older brother would teach a younger. And lots more.
Now, that families house is four stories tall. The first two floors are my sister's friend (and the guy)'s family. The third floor is an apartment of the eldest brother. The top floor is a vacant apartment, abandoned by a woman who rented it but got sick, went to the hospital, and never came back. Lots of us children would play up there, there was some furniture, a radio, bathroom and kitchen. The woman who used to live there also left some of her clothing behind.
One day we're playing up there, and we have to go to the bathroom. Casually mentions that my penis is very small, shows me his (of course, he's almost 6 years older than me, but I don't put all that information together. All I know now is that I have a tiny penis). He says maybe god made a mistake, and I was supposed to be a girl, and that's why it's so small; says maybe it's going to keep getting smaller till it's gone. I'm mortified. The worst thing in the world for a little boy is to be like a girl. He says wait. He goes to the other room and gets a slip from the dresser, that the woman had left there, tells me to try it on. Now, I don't want to, but this guy is my only friend in the world. So I do what he asks. Of course, it doesn't fit. Again, he says wait. He goes downstairs, brings back one of his sister's dresses (she and I were about the same size). Bingo. It fits. Again, I'm mortified, almost in shock. He says yes, that's it, he's sure that I was supposed to be a girl, because otherwise the dress wouldn't fit so well. Which it, of course, did. After all this I'm almost numb; everything starts to fit together; mom dressing me as a girl, my sister's underpants fitting me, me not wanting to fight and being labeled a sissy, so what he says kind of makes sense. I sit down, just stare at the floor. he asks me if I like the dress. I say it's o.k.(it was one of those little navy blue with white stripes sailor girl dresses). He asks if I want to wear it for a while, I say uh, no. He asks if I'm sure, because god might want me to, I say maybe later, and take it off. He says it's o.k, he won't tell anyone that we found out I'm supposed to be a girl, it will be our secret (we abused children are great secret keepers, aren't we?) The rest of the day is a bit of a haze, I remember we walked to a deli and got soda and some chips. I remember when I got home all I could think about was my life, and everything that pointed towards my new found girlhood, and how I'd die if anyone ever found out. On subsequent visits to that place, he would procure various outfits of his sister's for me to wear. Of course, other children would come up there and play, and several times I almost got caught dressed up. The sexual abuse that would later progress would go on for years, and the continued progression of my personality adapting from the normal boy growing up, to now trying to get ready for when I finally turned into a girl, would preoccupy my thoughts for the next oh, about 15 years, and by then I would always sort of feel like I really was a girl, and would want to dress up as one as often as I could. In those years, dressed and with long-ish hair, I would have easily passed as just another little girl. But to this day as far as I know, no one ever suspected what went on up in that apartment.

[docrobbysherry]

It took me over 12 years to find out there is NO woman inside me.

But, I over compensate for that by perfecting the pretty, young, woman on the outside!

[SaraLin]

I'd love to hear your account of when you first discovered the woman inside.��

Well - It wasn't a woman I found, but a little girl. I don't remember a time when "she" wasn't there.
Of course as I grew up, "she" did too - but more slowly, since "she" doesn't get out much.

I don't remember the first time I dressed, but it was probably by "borrowing" one of my sister's dresses and wearing it under the blankets in my bed.

[Jasmine23]

About 4 or 5, there was this maroon velvet dress with frilly collar and sleeves, it was so adorable I just had to wear it, got caught ( only time ever), but, I was hooked for life. I can't explain why I wanted to wear it so bad, just an urge I couldn't resist.

[Robbiegirl]

Unfortunately for me when I was about 6 my mother and Aunt had this great idea to fool an old nanny that was coming to visit by having me and my younger sister switch clothes. After being shown the simple skirt and being bribed I agreed. Once down to my underwear in the girls room my Aunt found a frilly dress she thought I would look cute as a doll in and despite my objections I was dressed in it. After hair barrettes were added and a hair band I was allowed to see myself in ! I couldn't believe how girly I looked ! I was shocked that It was that easy to make me look like a Girl ! My mother, and Aunt kept saying how adorable I looked and that maybe I belonged in dresses. I remember hating how short the dress was and that my older sister kept trying to talk my mom into putting me into panties with ruffles on the butt. But I kept checking myself out in the mirror in shock that my sisters dress fit so well and shoes and frilly socks. I also remmeber just how weak and silly I felt and how much enjoyment all the women were having laughing and teasing me.

Of course my old Nanny was very late and I had to spend way too much time in the dress so all the ladies got to teach me how to sit and walk and curtsy. My sisters use to love to bring up that story to tease me.

[Christina89]

I remember I was about 12 years old when I discovered the "pre-teen" girl in me. I was home alone one day after school watching tv, I was watching a show called Totally Spies. The main characters were out and about buying clothes for themselves. As I was watching an old memory popped in my mind where I asked my mother why I couldn't buy some of the clothes the girls were picking out for back to school. I grew up with what we all call an extended family and at the time the family had 2 daughters. 1 was about 3 years older than me and the other was about 2 years younger than me. My mother told me I couldn't cause they were girls clothes and deep inside I was deeply disappointed cause I liked the way they looked. Fast forward back to watching Totally Spies and something awoken inside me. Without missing a beat I went upstairs to my mother's room and started looking around. I found one of her bikinis on top of a box going into storage for the fall and winter. I decided to start with those. I took them and went into my room since it was in the back of the apartment and away from the street, the street we lived on was the main road into our neighborhood. I started to strip down and as I was putting on the bottoms I felt the awaken getting stronger. Then I put on the top and tied it up and the awaken came fully out. Afterwards I went to the bathroom and checked myself out in the mirror. I loved the feel of it on my body and had to admit my male breast looked amazing in the bikini top. After seeing myself for a few minutes in the mirror I went back to my mother's room and found a skirt, bra and top in her room and grabbed them. I returned to my room, took of the bikini top and put the bra on. I didn't struggle cause for a short period of time when I was 5 or 6 my mother and I lived in a one bedroom apartment and at times I saw her put the bra on while waking up. After putting on the bra I put the skirt and top on. I returned to the bathroom and saw Christina looking back at me with a smile on.

[Bianca Fay]

From a very young age I was completely fascinated with women and what they wore. In particular I had a strong desire to wear pantyhose but wouldn't allow myself the opportunity to don a pair because I was ashamed and afraid of the intensity of this desire to wear an article of women's underwear.

When I turned 18 I couldn't resist any longer and decided that I absolutely had to find out how it would feel to wear nylons. I finally bought a pair of sheer pantyhose at a local grocery store and I remember how electrifying they felt when I slipped them on. Needless to say, I have continued to wear pantyhose ever since that first experience.

Many years later I developed an interest in trying on other items of women's clothing and my ex-wife was very helpful in this foray; I've been a french maid, a nurse, a saloon girl, a Pan-Am flight attendant, and even a bride. However, the novelty (and work involved) of dressing up in elaborate costumes quickly wore off.

At this point in my middle-aged life I'm content with just wearing pantyhose everyday.

[GraceH]

I was a witch for Halloween in kindergarten, but that didn't seem to kindle anything in me. But on the first day in second grade, my teacher was discussing discipline and went over to her closet and pointed at a stack of headscarves, saying that when a boy acted up, he'd be made to wear one for the rest of the day. I remember feeling a bit giddy. During the school year a couple of boys had that punishment, which included having to wear it in front of the whole class, but then to wear it outside for recess, where the whole school would see you. I was too shy to act up, and was never punished in this fashion, though my best friend deliberately acted up to get to wear the headscarf. What I did, though, was sneak into my mom's drawer and put one on secretly. One day, I walked around the neighborhood wearing it, and was seen by at least two people. I was embarrassed, but loved it at the same time. From scarves, I progressed to other articles of clothing. I think my mom knew I'd tried on one of her bras, but she never mentioned it. When I tried on her lipstick (Victory Red) for the first time, the rush was indescribable. From then on, I'd often dress in various articles of women's clothing. At first, I pretended I was being punished, but by around age 9 or 10, I accepted that I simply loved to dress up. When I was old enough to drive, I'd buy makeup at drug stores, and clothing at Goodwills. Eventually, I lived on my own, and other than occasional purges, I've been able to dress occasionally ever sense. I've been married three times, and I told each of them before the relationship got too serious, about my dressing, and they all sort of accepted it, but none ever embraced it, so it's been basically DADT, but without having to hide the fact that I dress.

[Karren H]

I remember that my mother used to tell me that I was supposed to have been born a girl. A lot. But after my sister was born I started wandering into moms walk in closet and trying on her clothes. Can?t explain why but it started with bras and girdle and stocking and a cute pink sheer babydoll nightie. My parents were out for the evening and the sitter was busy watching tv. I do remember that the feeling was so amazing. I was 7.

[Lorna]

Revisiting this topic is always interesting (to me anyway!).
Bianca Fay wrote: "When I turned 18 I couldn't resist any longer and decided that I absolutely had to find out how it would feel to wear nylons. I finally bought a pair of sheer pantyhose at a local grocery store and I remember how electrifying they felt when I slipped them on."
It happened a few years earlier for me, when I was about 13 and saw girls I knew starting to wear nylons - stockings, not pantyhose because pantyhose weren't around in those days. The difference with stockings was the intriguing mystery of what those girls were wearing to hold them up - and, just like Bianca, I absolutely had to find out how it would feel to wear stockings. Unlike her, though, just "slipping them on" didn't work because the stockings fell straight down again. I just had to find some suspenders and the only ones available to me were on my mother's girdles. Fortunately I was about the right size and stockings and girdle fitted reasonably well. I found out what it felt like - though those girls I knew probably wore suspender belts rather than girdles - and the feeling was enjoyable. Of course, that inevitably led to wanting to know what it was like to wear a skirt.... and so on.

[ClaudineD]

That spark that drives that need on any level is always a fond memory

[BrendaPDX]

I bought my first dress at a second hand store, I was about 14. My hands were shaking when I went to pay for it. I paid my money and practically ran out of the store. I tried it on that night in front of the mirror, it had a side zipper, I had never seen one before. As I zipped it up it drew the dress in around me and fit me perfectly. I stared at myself in the mirror, I couldn't believe the pretty girl there was me. I was hooked on cross-dressing from that point on.

[Debbie Denier]

I tried on my mothers when 10. Purchased a charity thrift dress when I started working. The most memorable was purchasing my 1st dress new from a trans friendly dress shop. The sales assistant help me choose it. I modelled the dress for her complete with underwear , nylons and wig.one of the most exhilarating ,exciting and memorable experiences of my life.

[MysteryWoman]

When I was about 11, I went to the bathroom one day and noticed my mother's nylons hanging on the inside doorknob. Without even thinking about what I was doing or why, I tried them on, resulting in a reaction I'd never before experienced (if you know what I mean). Needless to say that left a major imprint on my psyche that has never gone away.

[Sylvia88]

I was around 11 or 12, sixth grade, had three older sisters and that year I finally got a small bedroom to myself. My closet was packed dresses, shoes, and a dresser with all of my sisters excess!! At first I didn?t pay any attention to this but eventually became curious.
One late night I tried on a green dress with white dots on it. It had a zipper and I worked hard to get it zipped. Then I couldn?t get it unzipped so I slept in it.
The next morning, my oldest sister came in looking for something and saw me in bed in the dress. She asked what I was doing, I just said i couldn?t get it off. She just laughed and came over and unzipped it. She patted my head and left and it was never mentioned by anyone.
I didn?t mess with anything in the closet for a long time but eventually during my high school years as I had more time alone I started trying everything that would fit.
I was an athlete and doing this embarrassed me but I never stopped experimenting and was always careful not to be caught again.
After high school I don?t remember dressing at all then when I got married at 23 another world of secret dressing appeared. I was married for 15 years then divorced. Once I was living alone I slowly started accumulating my clothes, enjoying them in my on privacy.
Over the last ten years or so it has grown into a way of life for me. I only wear panties and I transform myself every day when I get home from work. I spend my weekends dressed and always sleep in nighties and nightgowns.
I do enjoy doing things in male mode but I feel being a woman is my true self and I am very happy this way!! I?m in my early sixties now and don?t intend to change, this is who I am! 🩷 Sylvia