When did you first crossdress?

I was just reading through several of the many replies to this question and it reminded me of how wonderful it felt when I discovered that i loved to dress up in feminine clothing. It was a mixture of heady excitement with a strong feeling that this somehow was a part of one's self. Along with all of the dressing I also remember being fascinated by women and their lovely clothing and also reading about a man who underwent sex change surgery. The latter story just fascinated me so much.

I noticed the analysis done by one of the readers that pointed out that the majority of us cross dressers began this journey between the ages of 5 and 12. It is as if we just found our true selves at that age. Sadly, society's mores and restrictions have landed many of us with guilt and frustration and prevented many of us from truly flowering. I do hope it is much better for young cross dressers today.

You make a poignant point about how wonderful it felt to wear women's clothes for the first time. What a special feeling!

About 15 years ago. I wore a blouse and Capri pants. Had a bra and panties on. No wig. I have a wig just can't get to that stage yet.

Wow...my first time was so long ago I really couldn't pinpoint an age. I remember trying on some pantyhose when I was really little...by age 9 I had managed to acquire a decent sized stash of them. Started branching out into other garments around age 11.

After reading through a lot of the comments on here I find it interesting that, to a lot of society, this is viewed as a choice or a sexual deviation. Most of the stories here indicate that the onset of crossdressing happened during the prepubescent stage. Kind of throws a wrench into the aforementioned societal perception. I have always felt like this was not a choice, but something that developed naturally in me for reasons I don't understand. The posts here seem to reinforce that feeling. I find it interesting.

The first vivid memory of wearing something I have is around 12/14 I found out a cardboard box full of brand-new lingerie (that a friend of the family whom used to own a lingerie shop offered around Christmas and such) and I'd run that box from top to bottom. However I'd previously browse through my mom's cloths and I really wanted to try them on specially shoes, never did (until later and barely could fit them) probably due to fear of getting in troubles.

It's interesting that everybody agrees in childhood memories.
By my side I was may be 6 or 7 and I like to touch my mom's panties and bra. Then being 11 I enjoy getting my sister's, older 6 years, Ra and panties and wear them sometimes but then at 15 I had my first heterosexual experience that last like 3 years, then several girlfriends and after my wife, so sexual activity was enough to put to sleep my femine side.
It was up to my thirties that that desire wakes up again. Just for a joke I start wearing my wife small thongs, that I bought for her, and I like the way I look in the mirror. I have a nice femine butt. But then in some swinger activity, I notice that a lot of guys like my butt wearing panties. Just around 10 years ago i fulfill my desire to completely dress and I enjoyed a lot, since then, any chance I have I do it full and is really pleasureble.

8-9 or 10, don't remember an exact date but was well before puberty. Something I have thought about a million times, why? And what made it stay? It's just an enigma to me.

Some years ago my then wife dressed me. A GF a few years ago then 8? months ago I got into it big time.
Many dresses, 4 bras and 3 wigs. (not keen on the wigs)

Would have to go back to when I was a teenager. I was home alone at times when my grandparents were out at the doctors and doing shopping. I would look in the closet for things to wear. My grandmother had enough clothes to start her own K-Mart so it was easy to search in spots where they wouldn't even notice that I may have pulled something out. I found a swimsuit and a shirt/skirt combo that both fit me and felt good. Most of the time, I was able to put it all back without them noticing. Especially in the closet where my grandmother had bags of clothes, there was no way she would notice anything.

I remember trying on a pair of my mum's knee-high platform boots when I must have been about ten or eleven. Also trying her lipstick on which fascinated me (all secretly of course).

Makeup and shoes are still my thing as well.

When i was 7 there was one of my mothers bras in the bottom of a laundry basket, i think it was left in there and forgotten about, i tried it on and it was awesome. I ended up hiding it in my bedroom for about 3 months, wearing it occasionally. My dad caught me wearing it and scalded me and said it was wrong.
When i was about 13 i think, i was home alone once and I tried on some of my mothers clothes again it was amazing. I am now 18 and Ive been doing this since because i have no money at this time to get my own. Honestly I would love to have my own clothes.

I was a teenager. My sisters had moved out and left all sorts of clothes at home and I would try them on.
Also when a freind and his family went on vacation, I would watch there home and try on his moms clothes. She was a very classy lady and had really nice bras, panties, slips etc. Do you remember the Leggs pantyhose and the plastic egg they came in? I used these as forms.

Now I have my own bras and panties, stockings and more.

Sigh,


Randi

i started at age 6 i really was not sure what i was doing - but got a thrill

I'm not sure when I first put on my mother's panties and slip but I do remember asking why I wasn't a girl when I was four. Around seven the thought I should be a girl really hit me hard and it scared the crap out of me. Shortly after that I did put them on. I remember playing house with my younger sisters and I always played the mother and dressed the part as much as possible.

I remember playing "dress-ups" in a dress when I was about 6 or 7 but got laughed at by family so the earliest I probably actively started crossdressing would be when I used to try on my sisters shoes and dresses after school when I was about 11 or 12. She would be off at lessons or sports so I could try a range of things on.

I was probably 13 or 14, but my sister was a year older, and on occasion, was able to try on her clothes.
When she was able to try on new fashions, including makeup, I wasn't too far behind trying on her look, all while she, and mom and dad were away at the time.
The need to dress took a back step when I left home to pursue work, girls, etc, but the buzz never really left. In fact, meeting a new girl meant the opportunity to try on her clothes when she wasn't around was never far away. All these years later, while the big picture of relationships has finally dawned on me, I still look forward to the opportunity to dress in her clothes when she is not around.

3 or 4 the first time I asked my mom for a skirt. She said it was inappropriate, but understood why I was so drawn to such a pretty skirt.
She had this jewel tone purple velvet knee length skirt that I adored.
Was the early 60's, and what attracted me so much to it, was that anything that touched it (even barely) left a mark.
There was more than one morning that she went into work with tiny little hand prints on the back of her skirt.
After about the second time (after her coworkers mentioned it), she caught on and always wiped the back of her skirt as she left the house.
The first time I actually wore anything was when I was about 8 I guess. Was a white one piece bathing suit, that I found in the basement while searching boxes for something else.
From there I was pretty much hooked.

Wearing my sisters panties when I was around 13 or 14. Would take them out of the hamper
and put them on when she was gone.

I've had a feeling about this for a long while. When I was about 13 I had an awful urge to wear my sisters clothes. First I wore her boots then a skirt. Since then it had waxed and waned so to speak.

I first crossdressed when I was around 8 years old. I found a costume bin with all of my mom's old dance uniforms and old school clothes.

When I was seventeen I would switch clothes with my girlfriend at the time during intimacy.

I was 5 years old, it was Mom's pantyhose and a girdle... yes never looked back either... I knew I was addicted right there!!!

I remember wearing my sisters skirts and dresses at 4.

At -40 weeks of age I was literally wearing a woman who I can only assume was also wearing clothing. ;)

I think I was around 9 tried on my one of sister's dresses and I have been wearing a kilt for 15 years because a mini would just get weirder looks.

That would be about the same age for me. Have never stopped for 50 years!

When I was 22 I took the opportunity presented by Halloween to dress. My gf at the time was frustrated because I kept being too particular (it was just a Halloween costume after all)

I hated my look, but loved the feel. People I worked with on a regular basis didn't recognize me until I started talking, and apparently as long as I kept my mouth shut, i had ppl checking me out as well.

On a side note, my mom saw the pictures and was (still is 9years later) quite upset, even though it was Halloween. So I won't be coming out to my fam anytime soon.

At age 5 I use to wrap my sheet around me and pretend I was a princess. Lol yea it's a choice and your not born this way. I'm sure at 5 yrs old I knew what I was doing.

I related this once before, years ago on the forum,. but here's the extended version.

I don't remember the exact age, but I'd assume it was around 5-7 years old.
For some odd reason, it was a rare occasion that I had the house to myself. It might have been the first time ever experiencing that. Curiosity got to me.

I was not home alone much, and my parents' bedroom was a place I was not supposed to be rooting around in.

Escpecially the dresser. Mother had this wonderful large, wide lowboy dresser with huge drawers and a dark hardwood top that she kept shiny clean and polished with Pledge, so that even a speck of dust could not find a place to adhere.

On top of this dresser was a tri-folding mirror I'll never forget, because if you folded both wings inward they formed almost a triangle, and got you in the middle of them, you were in a house of infinite mirrors. I discovered a magical fascination with mirrors for the first time there.

There were things in the dresser that were tabu. There was occasionally a handgun. My parents were both police officers, so this was not uncommon, and I Dad had lectured, warned sternly, and taken me out and allowed me to fire it many times, partially to scare me with its noise and partially to kill any lingering curiosity that might end with me or my brother being killed. Also, dad's collection of porn magazines, and sex books were in one drawer, buried under some clothes. Once in a while (every time we were home alone together) my brother and I would get them out and curiously look through them. 1970's Hustler magazines (with the most hilarious cartoons in them) gave me my first view of sexual imagery, but didn't keep my attention for long, probably because I was years ahead of puberty. I knew they were something I was not supposed to be looking at, and that made me extremely curious, and was part of the charm that made the dresser this sort of magical box of esoteric wonder. It took on that air of enchantment that creates the sentiment of family heirlooms.

Everything associated with the dresser was magical to me as a child. The magic "zone" between the mirrors, the strange books, the grown-up things, the fact that it was forbidden and we were scolded and told not to open the drawers.

I guess that's why the ornate little box at the back of the bottom right drawer was able to turn me into a crossdresser for life. That box and its discovery was the end of whatever else I might have been in life, and steered its course probably more than any other single thing since. What was it? Why was it stuffed at the back, and covered with old brown corduroy pants?

It was a precious little white box with beautiful designs in it, and seemed to be tied closed with a satin ribbon. From the first time I saw it I had to know what was inside of it, and I began to peek in a corner of it. But there was not an opportunity, as my mother came home and nearly caught me looking in her drawers. I guess I learned that this magic was to be secret even then. I hastily threw the old clothes over it, closed the drawer, and tiptoed out of the room, as she was coming in the front door.

It was a long while before I got the chance to see the box again, but it was always there in my mind whenever it seemed a chance might open. You know the feeling. It's exactly the same one as waiting for that rare day home alone for an opportunity to crossdress. The chance would present itself, and I would seize it, but I could not make or manipulate it to happen, because I was never a very good liar.

It took a long time. but eventually it did happen one day that my father was at work or on a trip, and my mother took my little brother into town to the mall and the market. I was on the sofa, noncholantly pretending to be too engrossed in a cartoon or something to want to go shopping with them, when I was in reality anxiously waiting to see the car pull out of the driveway, so I could sneak right back to the dresser and open the precious little box.

As I've said, this dresser was like magic to me, charged with exotic sexuality, forbidden tabu, the danger of being caught, mixed with this endless dimension of triangulated mirrors atop it's impossibly glassy surface. And now there's this beautiful little box tucked way in the back.

I set the box on the top of the dresser and opened the lid, terrified to the point of physically shaking that I would not be able to close it again without it being obvious that I'd trespassed. How would I tie the ribbon again? It didn't matter at the moment. I had to get inside.

White tissue paper was folded in many leaves just under the lid. I carefully unfolded each leaf, cringing at the crackling sound even though I was home alone.

I was greeted, at the heart of all these things magical and secret, with gleaming white satin and lace. My anxiety ws at its peak, and the fabric seemed to glow ferociously as I lifted the garments from the box. A beautiful shiny pair of gleaming white shoes, precious little white socks with lace frills all over them, a lacy little bonnet with long ribbon ties, and a satiny sort of gown, white and perfect. My aunt who lived out on the country collected doll, and had a house full of them, and these clothes were clearly the type that I'd seen on the prettiest ones she had whenever I'd visited. But they were bigger, person sized, it seemed.

This became my ideal of the feminine dress. Well, I can laugh today at the irony, because what I was holding in my hands, though charged with as much emotional and spiritual energy as if it were a voodoo idol covered in freshly sacrificed blood, were my own clothes. It was my infant-age (or toddler) christening gown my parents had put away as a momento, a family heirloom. If only they know how much of an heirloom it is to me!

There was no thought or debate as I immediately stripped off my clothes and tried to put these garments on. This is the most curious part of the tale, because I guess I could have shrugged and put them back away, and I guess many would have done just that, but I did not. I was absolutely compelled to wear them, and there was no will in the matter. I was already lost to this spell.

The first thing I discovered was that everything was too small - much too small. As I've said, I'd outgrown these things I didn't even know were mine.

Pre-enacting a scene that would repeat itself over and over in my live (as I am rather large) I wrenched myself into these beautiful things as best I could, hearing stitches pop as I did so. I was going to become a beautiful doll like one of the ones my auntie collected, all dressed in white lace.

I got myself up on the dresser, feeling the delightful satin slide weightlessly over the glossy frictionless surface, and folded the two side mirrors in, and beheld...

And there I was lost forever, with just me, myself, and I, and yours truly, and the author, and this person right here, over and over, from a thousand impossible angles, in this beautiful gown and these beautiful socks and these shiny white shoes stuck over only the front half of each foot.

After considering the impossibility of the image before me for a lost moment in time, my next rational thought was "I need to put some of mother's lipstick on..." a strange dictate, but rife with compulsion -- and that's all she wrote, everything that happened since began at that moment.

I had instinctively placed myself in the middle of some ancient ritual with this triangle of mirrors, magical dresser, secret tabu box of exotic wonder. It was like I had built for myself a soul trap. I'm still there in it to this day. Odd. Funny old thing, life.

Possibly if this had happened a few years later, the recipe would have been different, and I would have evolved a more fetishistic fascination, but this moment forever tainted my dressing with this weird magical and spiritual vibe that goes quite deeper than anything that came later to turn me on sexually. I cry when I think about this. I cry when I write about this, but they are good tears, the kind that come when you stop to consider heavy things like the passing of time.

My parents are in their 70's now, and one day when they pass away, I guess they will leave me the dresser. I have not looked at it in many many years, but I don't need to right now. One day, when the opportunity arises, the haunted dresser will fall into my possession, and it will assuredly be a sigh of a milestone in life. I bet the little gown is still in the back of the drawer where I replaced it, and that in all these decades, nobody has ever noticed the ripped stitches or that the little heirloom socks are a bit stretched.

I remember wearingmy mothers skirts when I was 6 or 7, and skirts remain my thing, lingerie being merely a way to feminise my body shape and hold breast forms.

Wen4cd that is a beautiful story. I could see everything you was saying in my minds eye. Thank you for sharing

The best I remember it was around 3 or 4 .I remember walking around in my moms silk slip and her shoes playing around the house. I did this several times as a young kid and I remember I liked it and got upset when I had to take it off. After that I would wear anything I could when I got the chance. I continued this when I got the chance .I was about 10 or 11 the first time I put on a 1 piece bathing suit and played in our kid pool. That was fun til my dad saw and yelled at me. After that is when I started sneeking around and wearing things..

I think it was around 7-8 myself, trying on some of my sister's things

I’ve crossdressed very sporadically since my early teens, having had access to women’s clothing through my family, direct and extended. I was jealous of my younger sister since my mom and grandmother would spend hours making her dresses from childhood up until our teens. I remember that in my early sessions I found the sensations of the textures of fabric and materials very sensuous and connected to the new physical feelings I had becoming an adolescent. Dressing felt a guilty pleasure, but a compelling one to which I’d return on occasion. --- Camilla

About 8 years old.
My mums pucci evening dress and gold evening shoes.
I felt regal.
Lol.

I wonder if a person CAN stop? I can't!

Quote:

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Originally Posted by Nurse Sally

That would be about the same age for me. Have never stopped for 50 years!

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I started like lots of us long ago. When it wasn't unusual to see garter stockings on the clothes line.
Now its my stockings on the line.

I was 10. I found some girls clothes. Basic but turned me way on

Age 10 with Mom's Playtex panty girdle, 53 years later still can't get enough!

I was about 16! A friend of our stayed with us and I would look through her clothes. I found a nice outfit and put them on along with a pair of her boots. After that been dressing like that ever since!

First thing i wore was girls jeans when i was in 6th grade was teased alot at school

Probably around age 14 or 15. My sister's panties. My mother bought them for her as her first pair that were not kids panties.
They were very see-through nylon with lace trim.
She actually hated them so they stayed unworn (by her) at the back of her drawer.
She had no idea that I often wore them and put them in the laundry basket the next day. Our mother would wash them and put them back in the drawer, assuming that my sister had worn them.
To this day, neither my sister nor my mother knew the truth.

Around 3 or 4 years old.

I was about 6 or 7, its was my mother's nightgown.

I was 13, had a morning paper route. It was 1966 and I saw some pantyhose and a bra and girdle on a clothes line. Wanted to try them on and see what they felt like. Have loved crossdressing ever since.

First time i wore womens shoes well my wifes boots actually i was about 26, nothing else for about 10 years, now i dress fully and only wish i had started doing this alot younger, im not full time just for fun. But feel i missed alot of good years lol

Quote:

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Originally Posted by AlleyKat

When I was 22 I took the opportunity presented by Halloween to dress. My gf at the time was frustrated because I kept being too particular (it was just a Halloween costume after all)

I hated my look, but loved the feel. People I worked with on a regular basis didn't recognize me until I started talking, and apparently as long as I kept my mouth shut, i had ppl checking me out as well.

On a side note, my mom saw the pictures and was (still is 9years later) quite upset, even though it was Halloween. So I won't be coming out to my fam any time soon.

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Mums can be right bitches, if I'm honest. Mine is still none approving after she has known for 40+ years.. Doesn't make life any easier if I'm perfectly honest.

I was quite young, its a very old memory, 4 maybe 5 I dont know, and it was high heel boots, bought my own things in my early twenties I think.

When I was about 4 or 5, I used to wear my grandmother's slips and girdles...progressed to my mom's stuff and my sisters....
Now I have more clothing and lingerie than they do!
As I transition to 24/7, its fun to look back at how it all began.
I fully envision being a old woman in "old lady" slips and girdles...
So, it will end like it began for me.
:love:

I clowned around with crossdressing off and on since I was in my teens, but I never took it seriously until just recently.