When did you first crossdress?

[CONSUELO]

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.

[Xandra]

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

[Michele14]

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.

[Taragirl427]

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.

[cdheels]

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.

[Devi SM]

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.

[Tara Rushing]

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.

[Allison_CD]

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)

[AllieBellema]

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.

[AmyX]

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.

[EllieMayxxx]

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.

[Rhandi Spencer]

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

[erica2054]

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

[Vivian Best]

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.

[Alytv]

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.

[Tania75]

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.

[JessiAnne]

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.

[Daryl]

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.

[denisepascali]

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.

[sbay06]

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.

[Invisible Emily]

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

[CindyT]

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!!!

[tanya_cd]

I remember wearing my sisters skirts and dresses at 4.

[debstar]

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

[Jonni Lin]

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.

[Nurse Sally]

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

[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 anytime soon.

[Cdcdgirl]

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.

[Wen4cd]

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.

[Skirtgirl]

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.

[EllieMayxxx]

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

[mikayla1964]

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..

[SamanthaP]

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

[crobeson96]

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

[JosieH]

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

[Xandra]

I wonder if a person CAN stop? I can't!
That would be about the same age for me. Have never stopped for 50 years!

[Jess S.]

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.

[Ustour]

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

[Annamarie B]

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

[~Katelyn~]

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!

[LashingKarma]

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

[HollyGreene]

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.

[lisa_vin]

Around 3 or 4 years old.

[Kiersten]

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

[lauren21403]

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.

[Emma 1973]

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

[Jane G]

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.
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.

[Mykaa]

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.

[MissVirginia-Mae]

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:

[Cristy2]

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

[jahan]

I started crossdressing form the age of 13

[Michelle123]

Miss Virginiamae, I know exactly what you mean when you say you envision yourself as an old lady in slips and girdles. I see myself as the same as I grow older. very similar to my grandmother. She was the type that always wore her girdle and stockings daily, even around the house doing housework, or just lounging. it was always her daily routine to don her bra, girdle, stockings every morning as soon as she woke and bathed. I love visiting her, and sneaking one of her girdles and a pr. of her stockings, wearing them under my boy clothes the whole time I was there. Sometimes a bra too for bedtime. I would wear them all night. She would often comment on how long I liked to stay in bed in the mornings. I just didn't want to get out of bed. I wanted to stay in her lovely things in bed as long as I could. I loved seeing her lounging in the evenings, watching TV, laying bac on the couch, with her shoes off, showing her nyloned feet in her lovely rht stockings. Little did she know that I had on one of her girdles, and a pr. of her stockings under my boy clothes. Those are wonderful memories.

[ChristinaMarie50]

My first time dressing in private was with my older sister. She used me as a life size Barbie cool. My first time by myself was at 13, and I got caught by my mom. My first time dressed out of the house and with a guy was at 16. I lost my virginity that night.

[ZelenaCD]

I was about 14. Tried on a pair of my step-moms sexy satin panties and I was hooked♥ I knew there was something when my **** got instant hard. Now I dress all the time.

ZelenaCD

[wyomingwaine]

i was 7-8 when i tried on a pair of panty hose.loved how sexy they made me feel.i love wearing sexy skirts and panty hose.i recently moved up to womens tight jeans.the tighter the better my wife loves to put her make up on me and make me look like a hot chick wich i love.if i had the money for a sex change id do it in a heart beat cause id love to be a real women and wear what i want all the time without being judged for being me and finally being happy and feeling free.after my mom died a few weeks ago my entire family quit having anything to do with me after i told them i was a crossdresser and have been my whole life.now i still have to hide who i am.

[Sonyla]

At age 30, it seems to be rare :idontknow:

[MissVirginia-Mae]

I was 4 years old... dressing up with my grandma's girdles, slips and bloomers....then moved to my mom's lingerie....
Now I own more than they owed in their whole lives.....
:love:

[Geraldine1947]

I was 13, at home alone laying on my bed masturbating, as you do at that age. When I noticed mother's brassiere poking out of the washing basket. I went over, opened the lid and what a wonderful sight. Her knickers, brassiere and full slip were all there. I took them out, put them on and laid back on my bed. What an orgasm I had, I was addicted after that and wore her underwear at every opportunity I could. I found her suspender belts and corsets later on and I adored those too.
I have purged but always return, I find being en femme relaxing and calming. Xxxx Gel

[Yael L]

My first time was my first time at sleep away camp. There was a play being done by my cabin (all boys) and for some reason they chose me to play the role of the girl. I spent the day in a dressed as a girl. I was hooked.

[Valerie s]

For me it was Halloween was coming up I was 12 and was out running around with mom and she asked what I wanted to be for Halloween and I told her I didn't know. When we got back home she was upstairs and called me up and ask me if I wanted to wear one of her dresses for Halloween. Trying not to show my how happy I was at first I told her no but she said it would be fun so I said ok. We spent the rest of the afternoon trying on her dresses. We ended up picking a long ball gown that she had. It was now Halloween day and mom did my makeup gave me a bra pantyhose and wig. I was in heaven. Have been hooked ever since that day:)

[josie_S]

I was about 10 or 11 and I was home by myself. I'd already been very interested in lingerie and girls' clothes since we lived with aunt and uncle and my girl cousins for a while when I was much younger. I have two older brothers so I had never been exposed to much femininity until then, but I never touched their things (but I was fascinated by them!). So that day, home by myself, I walked into my parents' bathroom and found my mom's black lace bra draped over the towel rack and without thinking I slid it on over my t shirt and looked in the mirror. I remember the bra clasped in the front which I found even more thrilling (and still sort of fetishize to this day). Of course I took my t shirt off then, clasped the bra back on, and stuffed it with my socks and I could have stared at myself for hours! But soon after my brother came home and I then learned the panic of almost getting caught and the art of putting everything back exactly where I found it

[CCDTanya42]

Was 10 or 11 and had began masturbating by rubbing on my soft satin blanket on bed. Made me curious about wearing my mom's silky clothes so i went and tried pantyhose, panties, slips, girdles, and teddies.

Was instantly hooked, and would rub and orgasm while wearing her clothes. Firing blanks at that age, so i could orgasm without making a mess.

Was dabbler in CDing from then until early 20s when i started buying my own stuff (stripper heels, bikinis, etc) and as closet CD have gotten more into it in the past 5 years or so.

My dressing has always been sexual and will always be sexual. Not trans, but enjoy being feminine and bisexual fantasies.

[Alexa CD]

I think I was 8, it was a black pair of brand new pantyhose.

[Karine]

Even if crossdressing was in my mind since 15, I only started at 30. I was in a bad period (stressed because of work, not really happy). I said to myself: "life is short. You want to try crossdressing, you think you could enjoy it, so do it."
I have had so much fun.

[Tabitha_Sinn]

The first time I crossdressed was when I was 18. I of course, was alone when I did. I had a girlfriend at the time who had come over the next day. She spotted cigarette butts in the ashtray with lipstick on them. She thought I had another girl over and was not happy! So I had to tell her the truth. Lucky for me, she was very supportive of my crossdressing.

[nikkiwindsor]

Somewhere between 10 and 12 yrs

[budlinda2]

My sister dressed me at 7 and then i started to dress myself at about 13 I started just using lipstick and then slowly i added more and more.

[SeanErin]

The usual kids stuff when we didn't know what we were doing. Started about two years ago.

[Mylie Taylor]

About 14 years old. Little white tennis skirt from mom's closet. Was thinking about getting one this weekend, it looked sooo good lol.

[Desiree2bababe]

Five, I distinctly remember swiping my sisters yellow slip and wearing it when my Dad took me to a pond to fish........before that it was only mothers heels around the house. I still can't believe I got away with it.

[Martha G]

Age 59.

I went to a costume party as Charley's Aunt.

Beautiful, full hoop skirt with very lacy hooped petticoat, wig, bonnet, small drawstring purse, light makeup. very lacy pink satin pantallettes, nice gloves, fan ,broach, ladies shoes and an attitude.

After that I was hooked. Thoroughly enjoyed being dressed as a woman that night.

I believe that I had a pent up desire to be a cross dresser and it was this function that brought it out.

Have enjoyed dressing as a woman ever since.

[NancySue]

I think I was 6 or 7. We lived next door to a nice family who had two older daughters. I was an only child and would often play with them. One day they were playing "dress up" and they asked me to join in, so I did. They were putting makeup on and wanted to put makeup on me. I didn't object. When they were finished, they put a dress on me. We just laughed. A few days later, we were again playing and they asked me if they could dress me. I said "sure". They had an entire wardrobe. First, they did my makeup. Then nylon panties, next a bra, (I kinda got nervous). Then they helped me put on a pair of tan thi high nylons...I WAS Hooked! Then they gave me a pair of high heels. I put them on and they felt great and after a few steps, I could walk pretty well in them. Next came a half slip, skirt,a wig, earrings, necklace and bracelet. I wasn't sure how I looked, so after some touch ups, we went into their bedroom to look in the mirror. WOW...I thought I looked very nice...and so did they. I couldn't stop running my hands up and down my nyloned legs. We continued this fun, but I also began wearing my mothers clothes. I found her garter belt, girdles and nylon stockings. Oh my...need I say more? My mother would occasionally complain about the runs in her nylons. I just smiled.

[ChristaB]

The first serious time, head to toe, was about ten years ago when I was in my early forties. Prior to that I dabbled in wearing panties (not my own) going back to when I was a teenager.

[msannacd]

I was 13 and found a maroon bridesmaid dress in the basement. I was caught by my mom, yelled "I was curious" and we both laughed it off.

[TakaraYu]

If my memory is correct, my first time was around 8 or 9, but it wasn't until about 17 when I realized that I liked wearing what is classified as women's clothes

[CatchQueen]

Must've been 5-6...I know I was in kindergarten...I started with panties, pantyhose and gymnastics leotards.

[GBJoker]

Aged 10-11. I'd get home from middle school an hour before any one else in the family. "Borrowed" my sister's clothes. I was saddened when she tossed them all at Goodwill a few years after that.

[Sandra_tv46]

I
Was 10 or 11 and had began masturbating by rubbing on my soft satin blanket on bed. Made me curious about wearing my mom's silky clothes so i went and tried pantyhose, panties, slips, girdles, and teddies.

Was instantly hooked, and would rub and orgasm while wearing her clothes. Firing blanks at that age, so i could orgasm without making a mess.

Was dabbler in CDing from then until early 20s when i started buying my own stuff (stripper heels, bikinis, etc) and as closet CD have gotten more into it in the past 5 years or so.

My dressing has always been sexual and will always be sexual. Not trans, but enjoy being feminine and bisexual fantasies.

I'd do the same, come home from school being alone for a couple hours meant making a beeline to the panty drawer.

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My first lingerie item in my collection was a black babydoll that mom had hidden away, probably destined for the Goodwill but luckily I rescued it. Perfect condition. I was probably 10 or 11.

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House sitting was a thrill for me too. Neighbors would go on vacation for two weeks every summer (1960s) and I'd be asked to clean the swimming pool. Of course they also gave me a house key. I'd finish the pool and it was off to the bedrooms (daughter and mom). Great fun playing in the lingerie.

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I don't know what age I was, but it was definitely pre-school. I put on a pair of my mother's panties and walked around the house in them. When she saw me, she laughed hysterically and said her panties were way too big for me. My desire to dress in women's underwear lay dormant for quite a while after that, then came back full throttle about the time of puberty. I raided my mother's lingerie drawer every chance I got until she caught me one day posing in front of the mirror in her bra and panties. She scolded me for what crossdressing might lead to, but bought me a package of white nylon briefs for my own. I've been addicted ever since.

Yes I was already hooked on panties at 4 and was often seen walking around in aunts bedroom with her big panties. Can you imagine the sight? Mom told me these stories when I was older thinking it was just a passing thing. It wasn't.

[mickynylons]

I would say it was when I young, probably around 8 or 9, when I would find a pair of my mom's nylons and play with them in the bath room. It wasn't until I was in my early teens that I started to occasionally wear a pair of panty hose under my jeans. Later on, during my first marriage, I would start experimenting with wearing my ex-wife's dresses and skirts...even tried her makeup and lipstick in private.

[PattyT]

To some extent the question is what is mean by dressing as a CD. If it means just putting on a few female articles of clothing at home, I did this when I was very young, perhaps 10 or 12. If it means going out dressed androgenously, I did this in my mid 20's. If it means going out in a complete female outfit, I would answer my late 20's.
In any case this was much too late and I wish I could have gone out dressed fully as a CD when I was much younger. So much time lost.

The bottom line here is that I have wanted to CD ever since I could remember. It has always been a part of me.

[Stephanie58]

My first memories of cross dressing are in my mid teens (I had no opportunity earlier as i was away at a boys school for the previous 10 years) when I tried on my mother's clothes. Perhaps a little earlier i do remember being fascinated by my mother's big heavy corset and suspenders.

[fun_girl]

The first time I crossdressed, I was 13. I put my mom's panties, dress and heels. I was in heaven.

[Lori_Lyn]

It was Halloween when my older sister thought it would be fun to have a little sister to go trick or treating with.
I was around six y.o. I have heard. when She put a old red dress of hers on me and a mask of course and she took me around
the neighbor hood introducing me as her little sister if anyone asked. I was hooked and wore her dresses of and on
until the day she moved out

[Abby710]

I was always fascinated by women's boots as far back as I can remember, my mom had a pair of leather 70's black knee high boots with platform heels that I'd be allowed to wear during playtime, that would have been when I was 6 I guess, I loved the feel of my legs and feet encased in those boots and the feeling of a heel under the foot too, i got to the age when I was told off for wanting to wear them, guess mom thought I should have started to grow out of them by that time!

[CassandraRae]

I was 10. Folding laundry one night I found some curious items that made me feel squidgy inside. Mom and dad took square dance lessons on Fridays nights for some reason and sometimes my brother and sister were out too. I tried on the bra one such Friday night. Nice. Then the girdle and the slip. Oh my god! I remember hooking stockings one night but probably not then.

It only took a couple of dress-ups before I was caught. Mom and dad were surprisingly cool about, considering it was about 1967. I recall them, or at least Mom, allowing that it was OK if I wanted to try those things out. I was way too embarrassed to pursue anything though.

A few days later the kid across the street claimed to have seen me through the window 'in a dress and everything.' I don't think anyone believed him and he never mentioned it again that I remember. That's kind of odd now that I think about it. Anyway, all that failure was enough for me for a long time.

[BayBeeBlue]

My first memory, would have to be , as vague as it may be, something to do with me having to wear green tights for a school play (aged approx 5-8) ....I could have been the tree....not sure.
Next I remember, I'm trying on my mother's tights when my parents go to town....and getting caught once or twice puts me off for years with guilt, shame, abnormality,etc,etc.

[wanda66]

My gosh, the firt time like most everyone was with mom's panties etc, the last time was 5 minutes ago !

[Jacqueline1965]

I was between 3 and 5 years old...hard to remember back that far.