When did you first crossdress?

[Carla4Guage]

I've told this several times. I first dressed in something feminine at age 59, and yes I am a bit slow! But sister look at me now!

[claire1d]

Must have been around 12, I still see myself exploring my mom drawers.

[Jen84oh]

I was around 6 and tried on my moms pantyhose and love it.

[Kallyope]

First time at around 5... got more serious into it at around 11. So serious that I was feeling more female than men and was totally dreaming about become Calliope full time. But with the kind of family that I had, it was (and still is) unthinkable.

Tried like hell to quit several times. And eventually quit quitting :)

[carahawkwind]

Found some of my mom's lingerie when I was around 12 or 13, very much a puberty thing.

[Janine cd]

I'm thinking about age 7 when I tried on my mom's shoes. Then again I remember trying on her nightgown and slippers also.

[CindyR]

For me it was when I was 7, I wore one of my sister's dresses and heard my father coming up the stairs. I hid in the closet(no pun), and he found me immediately. To his credit he just told me to get out of my sister's clothes, didn't make it a big deal. Later that year I was out of pants, and told my mother. She made me wear my sister's purple polyester pants to school, I was embarrassed. I had to walk 6 blocks there and 6 back.

[Karolyn]

I was 12-13 when I tried my mom's satin PJ. That's when I knew I wanted to have more satin clothes, but it was hard to find for men. Switched to women ones, and there is no comeback :)

[Lisa Diane]

I was about 8 and mom was visiting the neighbor lady, for some reason I went into her room and got in her dresser. There I found a padded bra and tried it on, the feeling was wonderful, I had boobs! Years later I had to take out the trash and there was that same bra, it came back in with me and I kept it for quite some time.
Lisa

[SerephineStar]

I started crossing when I was about 12 years old. I was always curious about panties at a young age and I attempted to make them with my own little boy undies XD but that didn't turn out as planned. I eventually started to take my cousin's stuff (I was a weird kid I know) and my mom would forceably clean my room and find stuff so hiding things was virtually the hardest thing to do. but when I was around 14 years old she stopped and I was able to keep up a good amount of stuff to wear. so I guess I can say that I've been crossdressing for about 7 years now.

[RobynT]

I was very young, about 3rd grade I remember getting excited over a classmates yellow dress. I wanted to wear one just like it. As puberty took hold, I became very interested in the laundry hamper. mom and grandma's panties and slips. The feeling was earthshattering... continued thru the teen years ever so deep in the closet. Lots of questions and confusion over the years, but am at a point now that I am good. I guess wisdom comes with age. I am who I am, I do what I do, if you dont get it, that's not my problem. live well, be happy , dress often...

[heather ann martin]

I can't remember a time when I didn't crossdress. Having older sisters meant there were always plenty of dresses, skirts, etc. in the house and I took full advantage.

[MichelleDevon]

Definitely pre-school for me so probably around 4 years old so that makes it almost 60 years! I used to love t wear my mother's nylon slips and feel the slippery fabric against my skin. It was years later when I first got the opportunity to wear hosiery - my mother almost never wore stockings but I did find some as I rummaged through her drawers about 9 or 10 years later. The rest, as they say, is history! I still love nylon and satin lingerie, even better when you can wear them under a skirt or dress with a satin lining, and teamed up with sheer nylon and I am in heaven.

[CD Tammy]

I was five or six. I know the age because of where we lived at the time. I was in Kindergarten or first grade. My step-monster was a socialite who dressed up for everything. I don't think I ever saw her in pants. Since she had way too many clothes, she used the closet in my room as overflow. The closet was full of dresses, skirts and blouses. One Sunday, after church she had to do a quick change from her church outfit to some more formal outfit.

On my closet floor she left a pair of Size B, Leggs Sheer Energy, suntan shade pantyhose. I don't know why I put them on but that was it. At first, I wore them under my pajamas every night. Now, this woman had closets full of clothing. Dressers full of clothing. She never noticed over the years, but she lost many pairs of tights, pantyhose and yes, even stockings. She "lost" nighties and other dainties. When I said that she had a lot of clothing, she had two whole dresser drawers full of pantyhose!

[miko]

I was at the age of 10-11 I remember I had a whole day alone at home
I started playing with my mom's makeup and I wore a corset

[RachelsMantra]

I was a preteen and I found my mom's stocking on the trash. I was curious about the texture and just had to try it on. It felt so good on my skin I was instantly hooked and have been obsessed with nylons/stockings/pantyhose ever since. For awhile I was only into pantyhose but over the last few years I've been working my way to fully dressing including makeup, etc.

[Crystal Beth]

I was 6 and it was at summer day camp. There was a trunk full of lots of clothes for both genders to play dress up with. I was drawn to the dresses (go figure). As the years went by I was stealing my mom's or sister's clothes and wearing them if I was home by myself. I would fake being sick just to stay home and play with the clothes, always being careful to put things back exactly the way I found them. After I was out of the house and living with girlfriends I would wear their stuff if they were out of the house. My only regret is that I have better fashion sense than all of them combined :tongueout

[Susan Thomas]

We were on vacation in Canada and I was about eleven. My aunt and uncle thought it would be a good idea to hold me down on the ground and make me wear one of my aunt's bras. When we got home from vacation, I had a new-found attraction to my sister's clothing. I started wearing my sister's panties and then her swimsuit. One day, my mom got home from the grocery store, earlier than I had expected. She caught me red-handed wearing my sister's swimsuit. She started yelling at me and asking me "do you want to be a girl"?

Apparently, she put the fear in me, because I didn't crossdress again for ten years. I really didn't have a desire to crossdress, but one day (ten years later) I had an epiphany. I had just finished having a shower and there on the towel rack were my mother-in-law's pantyhose! Before I knew it, I was slipping on the wonderful pantyhose. I will always wonder if being forced to wear my aunt's bra was the genesis of my crossdressing? Years later, my aunt mailed me a picture they had taken with me wearing the bra. I look very upset and unhappy in the picture. Does anyone think that I would be wearing a bra a panties right now, if it hadn't been for my experience with my aunt's bra? Just wondering . . . . . . . .

[droopydog]

Around 10 or 11, sister had a wet look black one piece bathing suit ,just had to try it.

[sweatcakes]

I remember trying on panties and a bra at age 12.

[Jaidyn]

Very young for me. I could barley dress myself. I remember trying my sisters clothes when I was about 3 or 4.

[Dana3]

I've always been since a young age been attracted toward the feminine side

[Alice-n-wonderland]

Always been attracted to feminine fashion, as long as I can remember. It was the nylon clad legs that really caught my eye though. Tried on my first pair of hose at about 8. Can't hardly live without them now. Over time every thing else followed along. Now I go out as a girl, always in a dress and hose.

[CharlotteP]

My sister dressed me in a ballerina outfit when I was really young, like 5 or 6 and I remember that I thoroughly enjoyed it. After that it was when I was about 11 or 12, I wore a pair of my sisters panties. I kept it at just panties through all of my teen years and occasionally through my 20's, it wasn't until my 30's that I took it much further and started dressing fully, and under dressing full time.

Charlotte

[jasmine lee]

I was probably 5 or 6, at my Grandparents house, they had a box of dress up clothes, and I put on one of my cousins old school uniform dresses and wore it outside playing with my cousins. My Grandfather saw me and he wasn't impressed.

Later in my early teens, my Mum and Dad both worked, and I would fake being sick so I could stay at home by myself and wear my Mum and my Sisters clothes. Later while still living at home, I would by my own clothes, but I got caught a few times.

It wasn't until I was in my early 20's when I moved into my own house and really started my alternative wardrobe.

Jasmine

[Alison Bellis]

I think I must have been about 6, or thereabouts when like so many of us I discovered a cardboard box under my parents bed containing a number of girdles/corsets with suspenders attached and wrapped in tissue paper. An Aladdin's cave of feminine delight to me. I was hooked and have been ever since.

Hugs

Alison X

[melanie7412]

My sister dressed me in a ballerina outfit when I was really young, like 5 or 6 and I remember that I thoroughly enjoyed it. After that it was when I was about 11 or 12, I wore a pair of my sisters panties. I kept it at just panties through all of my teen years and occasionally through my 20's, it wasn't until my 30's that I took it much further and started dressing fully, and under dressing full time.

Charlotte

My sisters used to dress me in a ballerina outfit too! Couldn't have been more than about 7 years old.

[Karyn Marie]

I started when I was about four or five. I remember being at some of my mom and dad's friends and was supposed to be taking a nap, but I found their daughters tights, and put them on. They felt awesome. I had felt even before that that I was a girl in a boys body, and the tights just enforced that. My mom gave my sister some of her old dresses to play with when I was about six, and I used to wear them all the time. When I turned thirteen, I was wearing my moms bras, but got caught by my dad, and tried to suppress it. I was not able to do so, and by fifteen, I was wearing my mothers dresses and undergarments. I loved it, and it felt so good. I went into the service and kind of quit, but once out of the service, I started wearing my wife's clothing. I am dying to get my own wardrobe including panties, bras and pantyhose, but I do not have a supportive wife, so have to stay in the closet. I THINK she suspects, but I think she is at the DADT stage.

[Pink]

I don't remember this at all, but I've been told that my cousin dressed me up in a tutu and a leash and pretended I was her dog.

And apparently I liked it.

I dunno.

I can't remember.

[Robin414]

Pretty young for me as well. I remember as a kid about of about 10 my older sister had a gorgeous pink ski jacket she asked my mom if she wanted...my mom said no and she said she would just toss it out...I almost cried!

[Kacey Black.]

Let's see... about age 12 for me. Mom was at work and I was home from school!

[LuciaRamos]

I've started very late, was about 23? maybe 24 and found a Victoria's Secret Cataloge, was curious so bought some black boyshorts on ebay.... I would actually say I have not yet begun as I am barely branching out into swimsuits and yoga pants......I do like the business woman look so maybe in the near future I will strive for that look.

[EmmaB]

It was around 11 or 12, I can remember snagging my moms bra and panties and whatever else when no one else was home. But then it stopped for little bit and started up again in my mid 20s. I dont get to dress often nowadays but when i have the house to myself i do love to throw on a sexy bra and panty set or some yoga pants and a top and enjoy myself!

[wiwaw]

Age of five. Stood in a pair of my aunts heels and loved the feeling of it on my foot and how it made me taller. I then put on my sisters dresses and wore the heels around. I have been hooked ever since. I have slipped something of a womans on every week for the last 20 years.

[abbylhr]

I was around 12, saw a photo to a bride and groom, and my first thought was I wanted to be the woman. My first crossdress was much later.

[Mia27]

My family had a huge box of dresses and tutus and things like that. I remember being around 5 or 6 and loving dressing up in all the different clothes. But i was told to stop. It wasnt until i was about 10 or 11, i was walking past my sisters room and saw folded laundry on her bed. The panties are what caught my eye, I wanted to try them on. I snuck in there and stole a pair of panties, a bra, a skirt, and a shirt. I ran to the bathroom and tried it all on. It was like a dream.. I felt so amazing. I did that for awhile, sneaking all those clothes. I stopped for a long time. And now recently i dress fully make up and all. My GF is supportive which is nice:) i dress up fully every two weeks or so!

[kinkyboots]

5 or 6, mom had some clothes drying in the bathroom, I tried them on and got busted (and punished). after that parents were always checking up on me, got busted twice more later into the teens, got better at hiding. got the gay talk twice (Jesus would cry) didn't matter i was also busted with playboys, or how much i pleaded that i like women. my parents are all black and white

when i got married, my mom hugged my wife and told her she was scared i had been gay, but everything was okay now.

[GeauxStacy]

I was about 13. It started as a joke to shock my younger brother. I got dressed in my mom's work clothes. Nothing fancy just a skirt, blouse, heels, and some makeup. He was really surprised when he got home and I really thought I was just joking, but part of me felt, hey this feels nice.

[FayeXD]

Sixth, or seventh grade. About the time when I started to realize that girls have all the fun. Hmmph!

I went to a private school, where we wore uniforms. I always wanted a skirt of my own -- so I wore my sisters (secretly).

[Melissa in SE Tn]

91,000 hits on this thread... Incredible viewing

[Caryn Lynn]

I was about 6. I remember it started with my moms panty girdle and briefer. I just couldn't resist trying them on. After that i kept trying on more things especially a blue full slip and a bodysuit she had.
I was real sad when she finally gave them away. Even though she never worked and was always home I would sneak to the basement where the laundry was and try on what i could. Didn't get caught until years later.

[Lily Catherine]

Technically, age of 11. Qipao blouse with a floor-length pleated skirt. When I did it fully (lingerie, wig and all) it was a mini-dress converted from a skirt with a very short petticoat underneath. I also wore black over-the-knee stockings with that.

Strictly speaking however, I have been wearing women's jeans on multiple occasions since I was 9...

[Alicia S]

My first recollection is when I was 8. Tried on my older sister's school pinafore dress. The rest as they say is history

[Bunty]

I do like the business woman look so maybe in the near future I will strive for that look.

It's a great look! Go for it! :)

[Dixiecd]

I was in the navy and one of the females had left a set of panties in the dryer and it ended up in mine. I tried them on but felt silly however I could never let the memory go. I realize now that all the sexy "male" underwear was really to try and replicate that feeling.

[karenfry]

Preteen started wearing my mothers stockings and panty girdle.Then my sisters fishnet stockings. Then my wife's pantyhose and bra. Finally started buying my own clothes.

[Michelle 78]

For me I was around 8 when I very first tried my mothers dress and heels, it just felt so awesome, not to mention when I started to wear my mothers tights as well I was hooked!!

[cindi cinnamon]

It came late for me... Sorta.... When I was 7 or 8, I was constantly rearranging my tighty whities, by folding or rolling the waist band down, to resemble low cut or string bikini's... When I left home, I started buying my own undies, and quickly gravitated towards buying Jockey brand, Elance bikini's. Mostly in light colors to help with the "feminine look".
It wasn't until I was 40, that I tried on my first pair of women's undies. WOW !!!! I didn't realize until then, what I had been missing all of those years. I've been underdressing ever since. (23 years).
I had gone to Fredrick's and bought my wife some satin string bikini's as a Christmas gift, but she didn't care for them too much, because she didn't like the way they fit.
Soooo.... One day, I got them out and decided to try one pair on.... They fit me so incredibly good !!!! Next thing I knew, I was sneaking down the hallway, and peeked around the corner into the living room, where my wife was sitting.... I walked out into the room and her immediate reaction was that of shock and COMPLETE approval, and then she proceeded to chase me down the hall and into the bedroom, where we all know what happened next !!!!
I am so lucky to be married to her... She is so accepting and supportive...
And, like I said earlier, I've been wearing panties ever since !!!

[vixenvicki]

Well when I was a child my mother had given me an old purse and some costume jewelry (along with a few dolls) as play toys. [I always got the sense she had expected to have a daughter.] I'm sure I played in some of her clothes at an early age. My first conscious recollection of actually cross dressing was when I was about 7 or 8 and I got into my mother's underwear drawer. Got caught a few times with panties hidden in my room. In high school I acquired a pair of panties and bra of my own and got better at hiding things. In college, I started going to department stores and buying Vicki her own wardrobe, most of which is still hanging in my closet today.

[vixenvicki]

... and quickly gravitated towards buying Jockey brand, Elance bikini's. Mostly in light colors to help with the "feminine look".

Cindi, I totally love Jockey Elance panties. The microfiber ones are my new favs, if you haven't given them a try.

[cindi cinnamon]

Vixenvicki... I'm sorry, I should have been a little clearer with my statement... I meant Elance bikini's for men.

They served their purpose for a number of years, but I don't wear them anymore... Only the real thing for me nowadays.

[CastleCD907]

I started cross dressing when I was about 10 years old, I used to do laundry after school while my mom and dad was at work and I started to get curious about my moms underwear. When I started getting even more curious I decided to dig into my moms closet and found her lingerie and starting prancing around the house in it while no one was home. Once I started working and making my own money I began shopping at Ross or Marshall's for lingerie, panties, bras and started getting more serious and grew my collection. Now that I'm in my mid twenties I have had a lot of fun dressing especially now that I know how to do my makeup very well.

[teenagecd]

I remember that I used to dress up in the girl's costumes in kindergarten and play with them as if I was a girl. I was always a fairly girly boy and all my friends were girls. I was more likely to play with Barbies or princesses than superheroes or trucks.

It wasn't until I was about 12 though that I started dressing regularly. My mom had clothes that she stored in my bedroom which was formerly the spare room. I happened upon a bin of her old clothes as well as some cute heels I fit into back then. i put on the heels, an old dress and conveniently a wig from Halloween and felt soooooo pretty. After that experience I was hooked.

[Cynthia T]

Spring. I was 13 or thereabouts -- Only reason I know is that I didn't notice what my 7th and 8th grade teachers were wearing, but I still remember the heels my freshman Algebra teacher wore. Anyway, I was home alone, supposidly doing homework while actually reading a paperback, when one of the characters mentioned high heels. Suddenly whelmed, I got a pair of my sister's heels and tried them on. I've been borrowing/finding/buying girl things ever since.

[Katiekins]

My first time was when I was about 10 or 11, possibly earlier because I'm sure it was before I started high school (UK not American). I was in the bathroom and looked over to the laundry basket and had an overwhelming urge to try on my sisters clothes. Since then I doubt there been a day where I've not thought about dressing in some form.
Katie x

[Kandi Robbins]

Age 5, a dress behind the garage with the 2 neighbor girls. I still remember it 48 years later!

[Ellen2d]

I was probably 11 or 12 when I would sneak my sisters underthings. When I was 13 I went out for Halloween en Femme. I really liked it but really didn't do any more until I was in my 20's. It was in my mid 40's when I discovered a local crossdressers community. After going to my first meeting I went full throttle getting a wig, buying clothes and attending more meetings which were held in the party room of a local gay bar. The first time I went out on my own was after a makeup session with a pro. I went to the Mall Of America in broad daylight. There were a few shops there that catered to the CD community and I was treated very graciously. Today I'm older (20 years) and I don't venture out. IN fact I haven't done much other than wearing panties and occasionally nylons. Yesterday I had an urge to do more but when I opened the suitcase with my stuff I found it filled with mold. (We'd had a flood last year after a power outage, I thought I'd taken care of everything but apparently not) So I think I can salvage the wig as being synthetic it wasn't destroyed, just smells musty.

[claire_hollinger]

I would have to ask my mother lol. I have tried to dress since can remember. Ended up in counseling for it, and they even made it a rule of my juvenile probation (unruly child for dressing against my parent's wishes). I later had the rule removed as it violated my civil rights, but It was a very bad time. It wasn't until 2 of my brothers came out as gay that i was able to even speak to my mother about it without being judged.

[Mink]

2 gay brothers AND a crossdresser?

she must have felt like something was in the water!

[claire_hollinger]

She had my two older brothers, then me, then 9 years later she decided she wanted a girls and tried again. She had a boy, but thats because she ALREADY had a girl, she just didn't know it :)

[Joan.Meredith]

I was house sitting for some neighbors while they where on vacation and their girls were my age, and I tried on one of there swimsuits plus a few other pieces of clothing. That was about 10-11 years old, I already knew something was different about the way I was. It just helped me confirm that, "yeah I'm not like most boys".

Joan

[CorsetsnPetticoats]

For me it was probably around 6-7 years old and it snowed outside. My mother was worried about me getting cold, and made me wear my older sisters pink dance tights under my outer clothes to keep warm. I remember being embarrassed then, but it must have been the trigger that started on my path for a love of frilly things.

[Diane Douglas]

The first time I remember actually wearing girls clothes I was 15 and put on my sister's bikini for a minute or so. The first time I fully dressed was when I went to see Rocky Horror on Halloween with my GF and other friends. I had wanted to dress in girl's clothes several times before, but couldn't because it wasn't right.

[Pat]

I don't know when I started but I know that when I got caught I was 6 or 7. My Mom had a really nice bathing suit made of some kind of stretchy / slippery fabric. I found it in storage one day and put it on and felt so awesome that I hid the bathing suit under my mattress and every night after my brother fell asleep, I'd wriggle out of my pajamas and into that bathing suit and sleep in it. Early in the morning I'd wriggle out of the suit and get back into my pajamas. This went on for over a week. Then Mom changed the sheets and found the bathing suit. She told my Dad and he flipped out. He was shouting and carrying on and I learned a very valuable lesson -- don't get caught. ;)

And I didn't get caught again until I was 11 and my grandmother found me where I had tied myself up to try to look like one of the girls on the covers of my Dad's "Men's magazines" from back in the day when they all had women bound up in skimpy clothing and threatened by Nazis or what-have-you. She wasn't at all cool with it, but she didn't tell my folks.

So many of us started in the single-digit age range -- long before puberty. The need to dress has to be baked-in, I can't believe it's learned behavior or choice. I'm on the right track, baby, I was born this way....

[tammie]

I first was dressed at age 4 by my mother who was put out with me for annoying my older sister and her friends , she stripped me naked and put ruffled panties on me and then lacy socks and maryjanes , then she put a blue gingham party dress of my sisters on me , that buttoned up the back (I knew I couldn't take it off by myself) .

This was so humiliating for me in front of my sister and her friends , I was both stimulated and shamed . I don't know if that helped influence me to put on my older sisters black underwire bra one afternoon when I was home alone .
But soon after I was caught by my mother wearing it and she got an eyeful of how much I liked it when she made me strip and took my sisters bra and LLPG away .

Wearing that bra that fit me like a glove , changed my life in that instant I got all adjusted into those lace cups. I still love it when I wear a brassiere just as much as the first time !

[amberporteraro]

My mother caught me at her makeup counter putting on mascara when I was 6. Haven't stopped since.

[Justice327]

I used to wear my mom's clothes at like 8 when she was at work or out of town. Luckily I was never caught. But I didn't fully dress (make-up, hair, clothes everything was about 2 years ago when I came out to my wife. She did my make up the first time I dressed for her. She picked my clothes out some me and did my hair.

[ashleymcculloch90]

Age 3, sisters pink tutu, mom found me and when I started crying said "it's ok honey you can wear anything you want. Still took me 20 years to admit to myself that I wanted to be fem all the time.

[toriryan332]

My foster parents were leaving town for an extended weekend and didn’t exactly trust me ( who can blame them…) so they decided to have someone house site with me. Cindy, the daughter of a friend of a friend of my mothers’ had agreed to watch me and the house for 4 days. She had told my mother that she was 20 and home from college, actually she was 17 and just wanted the money and a cool house and car to use for the weekend. When she showed up, my jaw hit the floor. The doorbell rang, my mother opened the door, and there stood the hottest girl I had ever laid eyes on, tight jeans, lace up boots with fur at the top, and sexy white puffer coat with black fur around the hood! After spending most of the afternoon and evening at the mall, we returned home and decided to watch a movie, Cindy suggested we change into pajamas and just crash in front of the tv. About 30min into the movie, we are both lounging on the couch, and I mention that I was cold and could she hand me the blanket on her end of the couch. She reached over grabs her sexy puffer coat and says “here just use this” and proceeds to snuggle up to me and cover us both with her jacket! I sat motionless, not knowing what to do or say, just taking in the moment, not wanting it to end. A few minutes later she asks if Im warm enough, and then starts to gently rub my arm as if to warm it up. I slowly relaxed and the next thing I knew her hand moved lower to my hip where skin was exposed between my shirt and pajama pants. It tickled and I squirmed, now realizing I was ticklish she proceeded to laugh and try to tickle more, which turned into a wrestling match. The next thing I know she is sitting on top of me, her coat between her and my pelvis and she starts to grind. After a few minutes she leans down and kisses me, and I started to have the weirdest feeling between my legs. She reached down, grasping my **** through her coat proceeds to stroke me, finishing with the first orgasm of my life. She rolls off of me and I go and change. I come back and curl up next to her on the couch and she covers me again with her coat. As we are leaving the house, I can’t find my jacket. Cindy tells me to just wear her coat and that she has another one she can wear. I look at her strangely, and she says…”just put it on!” I oblige her and look in the mirror as we are leaving. I love the look, although it is a little femme.
Once at the mall, we proceed from store to store looking at clothes and I was getting quite bored. Cindy and a couple of her friends start whispering and giggling. Next thing I know they have picked out some clothes and hand them to me and tell me to go try them on and model for them!

And Ive been dressing ever since! and I have an insatiable coat fetish!!

[tammie]

HI All: I swear some guys have all theluck.

[talonX]

I remember getting into high heels when I was around 12, then dressing as much as I could when i was home alone in high school - usually when everyone else was at church, oddly enough...

[fiseldon5]

My mom bought some panties for a neighbours daughter and I found them and tried them on. OMG. Hooked from there on.

[RobynT]

My earliest memory was very young,1st or 2nd grade and obsessing about a classmates yellow dress. I wanted one just like it. Didn't know why at the time, it was just pretty... Growing up in a house with my Mother and Grandmother, I remember them getting ready to go somewhere, putting on make up, in a slip and panties (age disclaimer, grew up in the 60's/70's..great vintage lingerie). It then moved to the clothes hamper, and quickly progressed to raiding moms panty drawer(one of the benefits of being a latch-key child). I dabbled for many years, including through a 15 year marrage, living in silence. Since the divorce, there's been no looking back

[DonnaP]

for ne grammar school sometime with my sisters sweaters and Bras and a few times with my Moms even tried best friends sister clothes once. Very scary when you enter another house when no one is home also very exciting and stimulating but never went back to much fear of getting caught.

[pinkDOT]

As a young kid, 6 or seven i used to play around with purses and stuff my toys in there :) at such a young age i did not understand why boys weren't allowed to carry such a cool gadget. I have also played a witch in a school play and wore a skirt :) (because I was the only one who could remember so many lines of text). Years went by and the first time i put some clothes on, innocently, was at the age of sixteen. I have asked my good friend who was opsn minded if i can try on her bra, panties, put on a tshirt and try on her jeans. She was ok with it and i was just being "curious". Well now I know that it was not just curiosity, it was something tht made me smile. It felt good :)

[Carolana]

Greetings. I had a surprise introduction. I was about 12 or so and had never had any sex education. I was totally in the dark about it. My first erection came as a result of my brothers and I playing good guy and bad guy. We were pretending to be captured and tied up (big surprise...not). We happened to be in a large closet and my brother pointed to a dress and suggested I put it on. The connection to the erection was innocent but established. At a later date I wore the dress while alone and had another erection. Not understanding what was happening, I just went with the good feeling. One day I had a climax while in a skirt. I was confused and concerned, not knowing what that was. By the time I found out its real purpose I was rather hooked on the practice. So, the basis is the sexual comfort and pleasure I get from it. However, I am in no big rush to climax while cross dressed. It just feels too good to end it, as the climax usually takes away the immediate urge. cheers, all.

[auste]

i was as i remember about 14years, i tried make up and the mum dresses, it was amazing

[rhondasmith42]

It started around 7 when I tried on my mothers shoes (i am now a shoe demon) and it took of from there.

[Minerva Morgan]

Perhaps the greatest difficulty in such surveys is memory. I do not think too many people can remember specific events at ages 1-2-years with any accuracy or completeness unless it was something especially significant.
The following numbers are, therefore, not particularly accurate. Having examined similar polls in the past, I decided that I would divide the ages into three-year segments. This may not be a particularly effective means of examining the results. For example, most of the 1-3-year range was age 3; so 3-6-years would be a better range giving 37.7% of the responses.
Most persons responding would give a two-year range. The ages of 5-6 were very popular. Where such a range overlapped (i.e., 6-7-years) I would take the lower age. Where persons gave a school grade, I would add 5-years (grade 2 = 11 years). This also affects accuracy. Some people answered more than once. I think I caught most of those. Some person’s answers were simply too vague to derive an age with any reasonable accuracy. Basically, the results, while indicative, are a bit fuzzy.
The first time I saw such a poll, I was a bit stunned at how early the onset of Gender Variance or cross-dressing would be. The conclusion I take from that is that the predisposition to Gender Variance exists before birth and/or is evident from the time a person is capable of making the distinctions between genders. Also, that Gender Variance will most often manifest itself in using socially defined Symbology associated with gender. That is a young male will see femininity expressed and will want to use similar means to express their femininity. Not only does the sense of gender exist at an early age, but also the sense that a gender or varying genders are appropriate to the child. What is generally known as Gender Identity develops probably prior to or with the development of the ability to identify persons, objects and elements of language.
Another factor is that the onset of cross-dressing is dependent upon two factors. First is the ability to distinguish gender. Since what gender is basically defined rather than a pre-existing condition this is an introjected perception. For example, that wearing earrings is feminine is true in some societies, but not in others. Even so, the need to make such a distinction, regardless of how that distinction is defined, appears to be intense and derives from some prenatal factor. Otherwise it would not be evident so early. For the Gender Invariant ‘sex-matched’ persons (i.e., wholly masculine males), the matter would not be overly significant until later years. For the Gender Invariant ‘cross-sexed’ person (i.e., wholly feminine males), the early years would be very difficult and conducive to despair and depression; and they would not fully understand why this should be so.
That a large number of respondents state that ages 5-6-years were most significant to them probably ties into the period when one engages in a wider socialization (i.e., pre-school and kindergarten) heightening the awareness of a perceived difference between masculinity and femininity. Such a period may be very stressful for the Gender Invariant androgyne who feels compelled to avoid any gender presentation.
As well as a predisposition to Gender Variance, the onset of cross-dressing requires opportunity. Most often some factors include the presence of females in the family and a period of being alone at home. It seems that the second condition, of privacy, would be rare for someone of a very young age. This is another reason why the responses given are a bit surprising. Being home alone, Hallowe’en, theatrics and juvenile high jinks are commonly mentioned.
A very quick survey of the responses so far gives roughly:

1-3 34 5.0%
4-6 222 32.7%
7-9 139 20.5%
10-12 167 24.6%
13-15 58 8.5%
16-18 15 2.2%
19+ 44 6.5%
Totals 679 100.0%

Again, if the earliest group were revised to be ages 3-6 (and few, if any, actually mentioned ages 1-2-years), that would be 37.7% recall a very early onset of Gender Variance or cross-dressing. Probably due to a lack of opportunity more that a lack of predisposition, ages 7-15 (when children are given increasing independence) are 53.6%. Although cross-dressing is often described or thought of as a sexual activity, and while very young children develop and exhibit elements of sexuality (I recall being attracted to girls, especially ‘older women’ of 5 or 6-years, at the age of 4-years although I did not understand the nature of that attraction), it would seem that sexuality at a young age would not be a dominate factor. Pubescence would likely emphasize the sexual element of cross-dressing, and ages 10-15-years comprise only 33.1% of respondents. For the older respondents (13+ years) only 17.2% indicated a later onset. For them, while repressed gender expression may have been a factor, sexuality would likely be a key (and sexual situations, or even a lack of available sexuality) are often mentioned as relevant.
Another way of looking at these numbers is the classifications:

Prepubescent: 58.2%
Adolescent: 35.3%
Adult: 6.5%

These are similar to a generalized summation of several similar polls:

Prepuberty 63-70-71% 68±4%
Teenager 21-22-34% 26±6%
Adult 3-7-9% 6±3%

The onset of Gender Variance is, generally, in North American society, at an early age (roughly 3-11-years: 58-68%) with the bulk of the rest of persons exhibiting Gender Variant behaviour (roughly 11-18-years: 25-35%) in their youth. This is not consistent with a view that cross-dressing is necessarily sexual, necessarily related to Sexual Orientation or necessarily a matter of choice. It is consistent with the concepts that Gender Identity develops very early and is based on some sort of prenatal predisposition that will be expressed when it is permitted to be expressed.
Such polls are useful but, sadly, usually overlooked by those who could most use them. For example, those who feel that cross-dressing as some sort of adult paraphilia sometimes mistakenly referred to as a ‘fetish’. Usually those persons do not understand what ‘gender’ means, ‘fetish’ means or the nature of cross-dressing. They, however, influence public opinion as they are supposedly the ‘experts’.

Minerva.

[Lee Andrews]

I'd have to say in my early years 7,8 or 9. Found my love of nylons and I guess thats why I to this day can not go without them. I used to go and wear my moms shoes, nylons and skirts when ever I had the chance. Around 14 sucked when I my feet grew bigger than my moms shoes and I couldn't wear them anymore. My love of female clothing had me worried and confused in my younger years, still does to a point today. But I've come to the realization it somehow is a part of me and life goes on.

[Glorialovesheels]

I remember early on being interested in my moms heels say around 5 or 6 but for me it did not surface until much later say around 18-19... I discovered that women in high heels would arouse me .. and was curious to see what it would be like to wear them...it was such a turn, on and I wondered if stockings and panties would have the same effect. It did and used lingere and high heels to satisfy my cravings and used it as a "sexual aid" for masturbation for many many years... I never really had to urge to full on cross-dress until later mid twenties ...again in stages... next came skirts... then dresses... not until I moved out on my own that I fully transformed myself as a "women"

[Andrea_cd]

My earliest memory was mabey 5 or 6 trying on my sisters dress , it all started from there

["Gabriela"]

I think I was becoming a teenager when I tried one of my mom's skirt and lipstick... It all began there :o

[Emily CD]

I want to say I began around age 8-10. For me it was all about pantyhose at first. I am the youngest of 3 and routinely found myself home alone quite a bit. The absolute greatest attraction was in the form of pantyhose. This would have been back in the late 70s, which of course pantyhose were extremely popular in the states then and throughout the 80s and early 90s. Every time I dressed in anything feminine it always had to include pantyhose. The greatest thrills were wearing my sister's high school cheerleading outfit, which consisted of pantyhose, leotard, and a form fitting skirt. Next was wearing variety of grandmother's dresses, with bra, cup inserts, pantyhose, and heels. This lifestyle has done nothing but expand from there.

[victoria76]

It started for me around age 10, I tried on my little sister's swimsuit, just to see if it fit and found this amazing feeling! Before long I was wearing skirts, dresses, whatever I could find. I did it in secret and had no idea why I wanted to do it, but I couldn't stop!

[thecddj]

I was about 7, was a winter and was cold so i put a slip of my sisters on under my pj's, never looked back since :)

[KatherineH]

First time was when I used to put on my mums clothes & shoes when I was about 5. Then started again when at about 13 @ school.

[carroll1967]

I was 6 when mom caught me wearing her panties in her bathroom.The only thing she said was to put back when I was done.

[adrianacd92]

I was about 10 my sister left for college and she left a lot of extra clothes in her room since she always bought stuff and wore it once they were all like new and I had a nice starting wardrobe

[Karen62]

I have vague memories of being a little boy young enough to be put down for a nap. I remember not sleeping that afternoon, but instead finding a pair of my mother's pantyhose lying in a small brown heap on the top of her dresser. I pulled that gossamer fabric up my short, little legs and was immediately in love. Of course, they didn't fit at all (I had to hold them up by the waist), but the feeling was exhilarating (I don't remember, but I must have already known what nylons were at that age -- you know, when a small boy walks up to a trusted adult woman and extends his hand out to instinctively touch her, and he gets an unexpected surprise of a handful of smooth, silky nylon-wrapped leg). I seem to recall that I was caught jumping and dancing on the bed while wearing them. I was shamed for that stunt, and it was then that I immediately learned that a boy must be more discreet about these things. And for nearly 50 years since then, I have been.

[Vanessa2014]

August, 2014, age 68.
Never even thought of it before. I have seen it, and it never bothered me, though I was curious why.
Now I am curious why it is me, but am enjoying it as I could never possibly have imagined.
I am truly trying to slow down, as so many here have advised :-)

Vanessa

[Shads_Firehawk]

I had not long left school. I was 16 at the time. My mother used to go out a couple of times a month in the evening. It was around the 4th time that I had snuck into her bedroom, and dressed in her underwear, tights, a blouse, skirt, crammed my feet into her best shoes that were 2 sizes too small along with some lipstick and eye shadow.

She came home an hour early than I expected and I got caught. My mother was upset but didn't fly off the handle the way I thought she would. I knew she was not really happy with me doing it but put up with for few years before I suddenly stopped. That is a long story which I will put in another thread.

[crissytgirl]

It's tough to remember where or when I started to feel the urge to dress like a girl. I think I was about 10 years. I remember seeing my mom get dressed in the morning a few times and for some reason was really drawn to her dresser. There was a really perfume-like smell that came from her clothes. I looked in her top drawer and it contained her panties, bra's, and pantyhose. I did it in stages. I would try on her panties and bra when they weren't around. I can't even remember where they were, I didn't think I was old enough to be at home by myself. I enjoyed looking at myself in the mirror. I did that a few times, and then added her black pantyhose. I enjoyed walking around the room and watching myself. I got caught because I left her Bra's hooked.

[sarah555]

I was 14, tried on sisters underwear then moved on to her skirts and blouses whenever she was out.

[Rebecca Leigh]

I was like 12 or 13. Sister left for college and left so much for a bright, budding CD to enjoy.

[Miss Melissa]

I was 6 when I first tried on a pair of my mother's tights. I remember I'd been thinking about it at school & went straight upstairs when I got home, locked myself in the bathroom and put them on. I remember there was a diaper in the laundry cupboard too and I wondered if I should try that as well, but I just didn't get an urge to do it like I did with the hose.

[Patti Remick]

Ive been a CDr as far back as I can remember. I am the youngest of 3 with 2 older sisters that were 6 and 7 years older than me. My father travelled a lot on business and was away from home for days and even weeks at a time. When I was about 7 my mom went back to work full time. My mom always considered me a very 'grown up' little boy and felt I could take care of myself at home after school until my older sisters, and eventually she, got home. So from the time I was about 7 (c 1965) until well into my early teens I had plenty of afterschool 'home alone' time (this would be anywhere from 3-6 hours depending on when I got home and when my sisters did as they were very involved in aftershool activities). And for a young CDr our home was a paradise. My mother was a total pack rat (probably from growing up dirt poor herself) and kept almost all of my sisters old clothes from when they were younger. So I was home alone in a house filled with tons of perfectly fitting girls clothes. My father even had built a huge walk-in closet in our basement for my mother and sisters to keep there clothes in! My sisters had so much stuff - dresses, skirts, blouses, jumpers, even their old shoes! I wore their panties, tights, vests and training bras, and pantyhose. I wore almost everything of theirs that I could and by age 9 or 10 I was one of the best dressed little CDrs you could ever meet. Complete outfits head-to-toe, inside-out! And this was the 1960s and girls clothes were GIRLY. One of my sisters even had some wigs (she obviously was experimenting with her own looks) and they were just the icing on the cake for this little CDr. There were even ballet outfits and a skating dress. I dressed almost daily from age 9 to about age 14 in perfectly fitting and age correct little girls clothes!! I am sure this is the reason for my preference for little girls and girls clothes, as opposed to womens clothes, today (I can and do dress my age but prefer the younger -much younger - look). Eventually my sisters grew older and moved out and eventually most of the clothes were gotton rid of. I was never 'caught' or anything but certain events would lead me to speculate that my sisters and mother may have suspected something - Im just not sure. I was always very carefull to put things back the way they had been in closets, drawers, etc., but doing this so often I never could be absolutely sure I covered my tracks. I think my best allie in stealth was the fact that my mother and sisters were so involved in their own lives they did not have time to really see what I was doing. To this day nothing has ever been said. I look back on that time in my life with both joy and sadness. Joy in what I had and sadness that I would never have it like that again.

Love and hugs to all,
Patti Remick

[Aerotgirl]

First time when I was in second grade...I was a girl for Halloween.

Dani

[wanda66]

As long as i can remember i have worn panties, not all the time just when i could slip out of the wash and put them back before mom would miss them. I never dress fully untill a few years ago. I was spending some time away from homeand was out shopping and it hit me. Out of the blue i got everything from my toes up. Shoes ,hose, panties, bra everythin,then i had my hair done. That was a fabulous week . fortunately iam able to spend a lot of time as my other self if there is a good balance i think I've found it.

[icrossd777]

it started when i was 12 i was to dress with my moms clothes when der was no one at home

[ChynaDoll]

I can remember the first times I wore female attire. It was downright exhilarating! I was about 13 years old, and my older sister is about a year older than me. When no one was home, I would sneak into her room and try on her clothes. My favorite outfit was a jean skort and a tight fitting striped short sleeve t-shirt. This was a very confusing time for me. I mean, I really enjoyed this and every chance I could get to sneak into my mom's or sister's room, I would.

Converse sandals were my typical shoe choice with the skort/t-shirt combination.

[ChynaDoll]

So I was home alone in a house filled with tons of perfectly fitting girls clothes. My father even had built a huge walk-in closet in our basement for my mother and sisters to keep there clothes in! My sisters had so much stuff - dresses, skirts, blouses, jumpers, even their old shoes! I wore their panties, tights, vests and training bras, and pantyhose. I wore almost everything of theirs that I could and by age 9 or 10 I was one of the best dressed little CDrs you could ever meet. Complete outfits head-to-toe, inside-out! And this was the 1960s and girls clothes were GIRLY.


Wow, that sounds like heaven girl! :)

[CoraDee]

the first time i crossdressed was when i noticed my sister's laundry in the dryer. i was about 10 or so, and i had always wanted to just try girl clothes. i took out a few pairs of panties, a bra, feminine jeans, and a low cut shirt and off i went!

[tina16]

I honestly don't really remember the first time but it was at a very early age. I think it my have started when my Mom thought it would be cute to dress me up as a little girl for Halloween. I don't really remember the occasion but I've seen the pics.

I know most of my early dressing was at my Grandmother's house. I stayed with her while my Mom worked and she had a bunch of clothing that was her daughter's (my aunt) when she was a kid. I took the clothing for my own and my Grandmother was ok with it. This went on for quite a while (at least a couple of years) until my Mom found out and she freaked. I had to get rid of all the clothes but she let me keep one dress. Until my Mom found out, I thought it was perfectly normal for me to wear girly things. I don't think I even wore the dress she let me keep because the whole situation of me getting caught by her traumatized me and it was quite a while before I dressed again.

[Ozark]

5 or 6, mom had some clothes drying in the bathroom, I tried them on and got busted (and punished). after that parents were always checking up on me, got busted twice more later into the teens, got better at hiding. got the gay talk twice (Jesus would cry) didn't matter i was also busted with playboys, or how much i pleaded that i like women. my parents are all black and white

when i got married, my mom hugged my wife and told her she was scared i had been gay, but everything was okay now.

In my case it was my dad telling my wife shortly before we got married (1973), "I glad you two got together, we were beginning to worry about him." Later, she asked me what did I think he meant by that. I knew exactly what he meant by that.

[Laurelanne]

My first real recollection was, my Moms garter belt and stockings I was about 10 yrs old, she and dad were out, my aunt was upstairs with her Boyfriend, I put them on , I felt so girl and 'right".

[MarinaSweden]

I remember it so well. I was lying on my moms bed alone in that room. Reason why was probably because it was the only empty room in the flat we lived in. We were seven in our family and always some extra people visiting. I shared room with my older brother and didn't always want to be in the same room as him. But it could have been for another reason. I was probably about 6-7 years old.
My moms nightgown was on the bed. I felt the fabric with my feet and what happened in me I do not know. Electricity. I had to put it on and I did. Wow it felt good. Obviously my father came in and started to laugh a little, I think I said I was playing store. I wasn't embarrassed really, at that time I didn't see any problems with it. I don't think my father thougt of it again.
I even remember the colour of the nightgown, a bit offwhite. Made of nylon of some sort, probalby a cheap one, we were not a very wealthy family.

I was hooked after that I can tell you, and that is around 40 years ago.

[EmmaB]

I remember it like it was yesterday. I was about 13, maybe just under. I used to sneak into my mothers drawers and grab a bra and pair of panties to wear around the house when no one was home. It was an unlined white bra with a floral pattern and a blue and back thong that I fell in love with.

[Aprilweathers]

Right around 12-13 here,

Right around the time I started noticing girls in an amorous way, I started experimenting with their clothing. It was an on-again/off-again thing for a long time after that, episodic dressing here and there. It's funny, but I've been crossdressing for 20 years, but only in the past year or two did I start to consider myself a crossdresser.

[Missy_am_I]

I dont remember my first time, but I DO remember the first time I almost got caught. I was in 6th grade and my Dad almost walked in on me in my mothers bra and panties. Really scary at the time. Lol

[Suzie Q]

So, am I unique here? I'm retired and really only began cross dressing a few years ago when I discovered that my wife's panties fit me perfectly and I could wear them to work. Since then I've become "addicted" to dressing and part of my closet and some of my drawers are full of wonderful women's clothing. I do love it so when I get the opportunity to have the house to myself and I can dress fully.

[Nicole T]

When I was around 5 or 6, I put on a pair of my mother's pantyhose (I didn't think much of it in terms of crossdressing). My brother told on me and I got in trouble. I never dared to wear women's clothes ever again.........until now.... ]:)

[Jackmore]

I have always had a fascination with ladies heels, stockings, lingerie. I have no sisters so it was my mothers stockings/ heels I first tried in my younger years, thru my teen years. rarely done as a big fear of being caught. Later years not very often when I was living with someone. Big fear of being caught. Now for the last 15 years I have been alone and its nice to be able to lounge around the house in stockings and heels.

[SophieBee]

I had put my first time right out of my mind as it was in a previous life when I was in the depths of separation & divorce from my first wife. She had left some clothing in the house when she left and I suprised myself by finding comfort in he clothes. None of it fitted though so it was not very pretty and I put the whole thing away until CDing burst in on me again last year and it all came flooding back. I have to say it's all much more fun this time round!

[Eleonore]

I think I was around 10, I stole pantyhose from mum's wardrobe and .......I felt in love with that. Why did I start? I have no idea. Would I start again if I get to chose? YES endless times !

[pamela7]

Hi Suzie Q,

I think we're all-ages. as far as i can recall i was about 41 when i started. My wife was in on it, and we went shopping for me, such an exciting trip out.
i found that the thongs really don't work for me for all-day, but great for sexplay with her. I'm now wearing bikini briefs and high-leg briefs all day, home and out, and we're discussing the next step of me going CD at home. It's been long and slow, but I feel like a rush now to progress.

[CONSUELO]

Thanks to Minerva Morgan for conducting an analysis of the data here. I did a very crude one some months ago but the number of responses has increased greatly since then. Just like Minerva I was surprised by the number of people who remember cross dressing at a very young age and certainly before 10 or 12; over 80%. I started very young and being "dressed" was one of my earliest memories. She may be right in her conclusions.
The surprising part of this "survey" is the small number of people who did not begin dressing until much later in life. I wonder about that.

[Yulialuv]

I think I tried on my sister's dress when I was home by myself at like age 11 or so. But high heels seemed to be hardwired into me, I've been fascinated with them since I was really little.

[LexiNexi]

I started wearing my sisters clothes at the age of six. Dressed in a female part in our kindergarten school play about the same age.

[LexiNexi]

Thanks to Minerva Morgan for conducting an analysis of the data here. I did a very crude one some months ago but the number of responses has increased greatly since then. Just like Minerva I was surprised by the number of people who remember cross dressing at a very young age and certainly before 10 or 12; over 80%. I started very young and being "dressed" was one of my earliest memories. She may be right in her conclusions.
The surprising part of this "survey" is the small number of people who did not begin dressing until much later in life. I wonder about that.

I often wonder why we do it before puberty. Age 6 for me was really young.

[abby054]

I don't know, but I was at most five years of age. I recall asking my aunt, only five years older than me, why I could not wear the same pretty clothes like those that she and and other girls our ages wore. I do not recall her answer, but she let me wear one of her skirts and my grandmother's heels. I first went out in public fully dressed at age nine, at Halloween. My mother did a good job of making me look authentic in a long skirt and a peasant blouse.

[CONSUELO]

Several have wondered why we found cross dressing at such a young age and well before puberty. I distinctly remember having an interest in sex and being sexually aroused at a very young age. I noticed some of my nieces and nephews showing an interest in their genitalia at a very young age also. Of course it was only the parents who were embarrassed as for the children it seemed natural. I was sexually active well before puberty and once I found soft silky lingerie I tried to dress up and obtain sexual satisfaction frequently.

I think we have a certain sexual plasticity at that age and that is why an interest in clothing and other objects can be imprinted early in life. I have read that for males this is especially so as the male genitalia are external and easily stimulated which intensifies the response.

[missynicole]

about 11 or 12....my mom's bra and panties....

[Bea]

I was around 11-12 years old when I began wearing my mom's bra and panties. I was raised in a primarily female dominated environment and it seemed rather natural at the time.

[Jackie Meyer]

Not only can I remember I was 12 years old, but I can still remember the exhilaration I felt on my way home from school. This would be the day that would change the course of my life. Forever.

[Sarah-RT]

When I was 5 or so my sister dressed me in her communion dress for a laugh, hated it simply because of sibling rivalry but I recall my mom putting lipstick on me as a joke which I remember finding fun but I wouldn't relate it to crossdressing.

I was at my god mothers one time and she asked would I tidy up her kids playroom for 5 pounds(dollars) which I did and found a blonde wig which I wore doing it, I remember being afraid her or my mom would catch me doing it.

Around 6 or 7 I had a female friend who was my best friend since we lived in an area with a lot of older families with few young children and I remember she gave me a make over one time which I enjoyed but had no idea why, years later she had moved away and I stayed the weekend once and she did ballet and thought it'd be fun to let me try on her ballet clothes which then I knew I'd enjoy doing.

As a young teen my mother got married and I got a step brother and sister slightly younger then me and she'd often dress the two of us up which I definitely liked doing and my step brother didn't.

My first girlfriend was my step sisters friend and I told her about my dressing because I had learned what crossdressing was and wanted to do it, she bought me a corset and a mini skirt for 1 of my birthdays as well as gave me some of her old clothes. She seemed supportive but I never really dressed in front of her more then once or twice.

A funny story was we were making out on her couch one time and she put lip gloss on me, later she went into her kitchen and her sisters boyfriend asked her was she painting her face with lipgloss because she had it all over her cheeks and forehead and that I was hardly wearing lipgloss. We had a good laugh over that.

[Lisa LIckorice]

My younger cousin would always wear women's heels and nightgowns. My favorite aunt thought it was so cute and he always got a lot of attention. I'd sometimes slip on a pair of heels if they were laying there, but started dressing at my grandmother's home after school. I would go there after school while both she and my mom were at work. I'd be there alone for probably two to three hours per day. I remember the first time I slipped on her pantyhose! That was the first time I remember getting a hard on. My grandma had a lot of money and a ton of lingerie. Closets and closets full. She had maybe three hampers filled to the top with pantyhose! That is where she stored them because she had too many pairs for her drawers. It was a sissy heaven. After that I found the key to the "special closet." Grandma was a freak! She had dildos, strap ons, whips, handcuffs, etc. I started experimenting with her toys. I'd do my best to clean them up, but she knew what I was doing. I remember one December I got into the closet and there was a wrapped box with my name on it. I opened it up and it was my very own bright pink dildo. We had a talk about it later and after that I'd often go to Dillards and Macy's with her and she'd buy me lingerie. She was a queen and let me be a princess, never telling my mom or dad. Love you grandma! :)

[JessicaFoxx]

I first started when i was 16 we had a closet that stored extra clothing, and there was a women's dress being curious i decided to try it on and it fit, well i started going in the closet more often so i could wear it and it made me happier, so then we moved, and the laundry basket moved into the bathroom instead of the hallway and i would wear my moms and my aunts clothing (I know they were dirty but I was going to be cleaned soon) well that was a everyday thing. then when they would go into town for 2-4 hours i would go in their drawers and wear their clothes around the house. I guess that's how it started with me

[MsLana]

I played dress up when I was a kid with my older girl cousins a few times .I was maybe 6 or 8 yrs old.I don't really count that though. it was just fun kid stuff.Fast forward to adult life.I was in my late twenties , going thru my "cougar" phase ( before the word was fashionable)..I was living with a woman in her late 40's..worked in a hair salon and styled wigs on the side. Well , her partner and her started using me as the "wig head".We would party and they would style wigs and it was fun.One night they got the idea of dressing me up etc with make up and the whole works...it was just another fun kinky thing to do.Well , they then got the idea of me going out with them dressed!!!..WHOA!!! hold on sister..."aw come on it will be fun"..sooooo...I said just this once...they got me all dolled up and away we went..to a club which I think catered to CD and was pretty laid back actually. I was hit on continuously!!!...one guy bought me a damn rose...and they wanted to dance..the part I was digging was the drinks they were buying us..we did this scenario several times after that and well, it just kinda grew on me I guess...I passed very easy in those days..I am only 5'6" and was thinner then (of course) so it was quite a thrill to say the least.Now I am content to have playtime at home and the need to "go out" is not a burning desire....It's very therapeutic to me to be able to get dressed and just hang out at home in what ever I want to wear and be comfortable.

[Kathleencd]

I was about 14 when I started wearing my sisters bra and panties.

[JimmiLynn]

I was about 12-13 years old when I found some clothes someone had given us but my mom couldn't wear them. There was a bra 34d faded pink and a 1 piece swimsuit black with gold trim, tried them on and loved them. I had them until I went into the military.

[Michelle_G]

It seems like its been forever but I must have been in the 7 to 10 range. I remember trying on my mom's pantyhose and I was hooked. It was such a thrill I looked for more things to try on. I found her swimsuits and some old dance leotards she had in a closet. I still remember the leotards were the best . Both were black ,one was a soft stretchy cotton material with a scoop neck. The other one was more of a shiny nylon material and had a back zipper. I would sneak the pantyhose and the leotards into the bathroom to try them on.

[CD_Princess1234]

I agree it's been a long time since the first time. I remember trying on clothes of a friend's sister. My favorate dress believe or not was a shiney, shimmery gold dress. I played the part of his "girl friend" and he had to asked me out. We would lie on the couch, kiss and make out. It later grow to wearing my mothers panties and underwear. I remember when she caught me with all her clothes in a bag. I told her it was for Halloween and I was to play the "girl friend" of one of the guys. "It's a prank mom!" Really I want to wear it and be that person that wanted to come out. She wasn't happy and a bit confused I was cught and disappointed. I kept dressing even from my teens. It has been off again on again and now it's out there. Ive purged in the past and lost out on some great outfits. Now it's all in and fun. It's part of my life and part of who I am. It's trying at times for me. I have to see is it me or the person people think I am. Today I find woman very attractive and desirable. But at the same time... I appreciate the attention of a man when I dress. It's a completely different feeling as a woman. I get excited when a man holds me tight.

[Riddhima.mehra]

I was 10 then & I wore a bra. Unfortunately, I was not able to close it; since the buttons were at the back.

[melaknee]

playing dress up with 3 sisters when i was probably in 3rd grade. they were a bit older than me. heehee it's true

[Ellen2d]

I was around 12 when I first played with my older sisters clothes. Primarily it was her nylons panties and bra. I would wear them during the day when I was alone in the house. I think I was 13 the first time I wore a dress. It was Halloween and I went as a girl. I wore a dress and some makeup and since I didn't have a wig I wore a scarf. I remember going to a young woman's house that worked where my dad worked. She invited me in and was all complimentary. I often wonder if there was something I missed out on.

[Ms.Kenadie]

I got scared one night and slept on the floor in my Grandmothers room. I guess she hadnt cleaned up before she went to bed. There were a pair of pantyhose and panties. I was about 6 or 7. Been in love with the feel of pantyhose, panties, and lingerie ever since.

[vickie1952]

I started dressing at about 16, i'm not sure now why but it just seemed natural to me and i still love the feeling.

[Jayne]

At 5 or 6 a would swap shoes with girls under the table at primary school.
7 to 8 I could get into the pretty yellow bridesmaid dress in the play box at home and would hide it in the toilet then go put it on when no one was about.
In early teens I painted my toenails and borrowed my sisters tights, bra, skirt and boots and dressed in the local park toilet then delivered my papers before I changed back and went home.
The urges got stronger from there onwards, the rest is history.

[girlbh44]

I think I was about 10. I was at grandmother's and my little sister wanted to play dress up so I did too.

[casper064]

When I was about 4, maybe because the weather at my place was really hot, My mom then put me in one of her tank top. I can not forget the felling of the fabric.
Maybe that event was the reason why I am always attracted by women's clothes.
Long time later, when I was already in high-school, then I had a lot of chances to put on my Mom's bras and panties that she left in bathroom.
I have been married for 2 years. And now I can have my own wardrobe which was selected by me and my wife. I even have more bras than her :).

[Ceera]

For me there is a big difference between "When did you first try on women's clothing?" and "When did you first underdress or want to put on a complete female outfit and appearance?".

When I was something like 8 to 10 I know I tried on some of my mom's clothes in the privacy of the laundry room. Tried it on, looked at myself in the bathroom mirror, and took it off again quickly. But back then I wasn't about to try wearing her panties or bra under my clothes, or spending any length of time wearing any of it. And I certainly wasn't considering putting together a whole outfit, with or without a wig and makeup. I think I stopped trying on her stuff well before I started high school.

I knew by the time I finished high school that I was probably bisexual, but I suppressed that too, because I also knew my dad was homophobic.

It wasn't until I was in my mid 50's, after the death of my father, that I decided to try wearing panties or a corset, and purchased some for myself. Back then, I'd been writing fiction for 5 to 10 years that included some characters that were gay, lesbian or transgendered. And in one of my recent stories there was a young male who was experimenting with crossdressing. I wanted to try wearing panties and doing tucking, at least in part to better describe the feel and the process in my stories. But I also realized that my wanting to write those stories was probably an indication of some desires on my part that I had been denying all my life. With dad gone, I no longer had to fear him finding out. Kept it in the closet, though. I underdressed with panties full time, and admitted wearing the panties to my wife and daughter, but kept my small duffel bag full of a wig, my corset, women's clothing and one pair of shoes that I had collected over the next six months my secret. I doubted I would ever do more than dress at home, though I admitted to myself I wouldn't have bought the shoes unless I had some intent of trying to leave the house while Dressed.

A couple of years later (about a year ago) was my real turning point - when I would say I really started crossdressing, at age 56. My wife had also passed away, and I decided to actually buy some full outfits and some good wigs and makeup and prepare myself for actually going out in public in female mode. I came out to my daughter and soon half my closet was girly stuff. I have more makeup and girly clothes than my 19 year old daughter has! And for the past 6 months or so I get out 3 to 4 times a month in female mode!

[CDRMolly]

When I was 2or3 my aunts would play dress up with me(Iv'e seen pictures,I made a cute little girl),at about 12 or 13 I started trying on and wearing my sisters clothes-panties,bras,pantyhose,girdles.Wore some on and off for years until the last five or six years the urge really took off,and now in my 50's and enjoy it more than ever.

Thanks,
"Molly"

[Xandra]

I have been away from the site for a while but have so enjoyed reading the replies and the stories. Please keep them coming!

Xandra xxx

[Amanda77]

Thr first time wow, what a feeling. I was 12 and looking for something in the closet i came across a box full of my sisters old clothes and underwear. I just looked through the first time then a day or two later i whent back to it and took a training bra and panties to my room and slipped them on. I have no idea what compelled me to but like i said wow, it felt so good. a few days later it was bra, panties, and t-shirt and shorts. I'll never forget that day.

[susancheerleader]

Does wearing my sisters one piece swimsuit and gymnastics leotard count? That was the first garment I wore at about the age of 13.

[Kathrine]

When I was about 5 I used to sneak into my sisters room and try on a brown fake fur coat she had. I loved it, it had brass buttons on the front. My Dad caught me one day and told me it wasnt for me. I didnt wear female clothes again until about 12, when I started trying on my sisters clothes.

[SonjaThompson]

I was about 13/14 when I first tried on a pair of tights (pantyhose for US types), mainly because I really fancied women who wore them and I was curious. I tried this a number of times, and tried a pair of knickers and bra on once, felt ridiculous and then didn't bother at all until about two years ago. My wife was away for a weekend and I suddenly decided to try on some of her clothes. I ordered a wig, shaved my legs, and the rest is history. I honestly have no clue what prompted me, but I am happy I did.

[chris63]

Don't know the exact age. but around 10-12 years old. Wore my mom's lingerie and sister's panties. Fun!

[Satwiwa]

a few times in my 20's.. in my 30's I had the good fortune to have a Friend stay with me & my house mates for a few weeks. she brought a fair amount of clothes and they were kept in my walk in closet. once she went back home, she had mistakenly left behind some of her clothes. she didn't pick them up for almost a month. in which time I wore many of them - mostly her bras, panties and the bright Pink silky Negligee. I would put them on in the evening, lay around in my bed and often feel asleep wearing them. They felt soo wonderful and sexy. I took very good care of her clothes while i had them. I felt sad when she finally picked them up.
I loved that period and it certainly allowed me to be myself and start wearing women's clothing...

[suzzi]

All I remember is anytime I was home alone I put on my sisters panties bras nylons shoes and nite gowns! It was so much fun and exciting ! I was 10 or 11 and still enjoy dressing up when I'm alone.

[Joy3]

I was about 5 yrs old when a girl neighbor dressed me up in her clothes so she could have a girlfriend to play with. I loved it very much she and I played many times and i was hooked!

[Sophie Hogletta]

About 12 years old I think. It emerged at exactly the same time as normal sexuality. Kind of in tandem. Then through my teenage years I remained bewildered by it, trying female clothes on every so often. It never really goes away does it. It seems to be very hard coded.

[Cynthia99]

I was 12 or 13 - and I never understood it. It still makes no sense to me, as I am not passable at all. If I were pretty, I could almost understand it...

Good luck. I think this is a good group.

Cindy

[Sophie Hogletta]

Ballerina outfits. Nice. :battingeyelashes:


I was about 5 yrs old when a girl neighbor dressed me up in her clothes so she could have a girlfriend to play with. I loved it very much she and I played many times and i was hooked!

My best friend when I was five or six was a girl, but we never did that. You are very lucky! Innocent times . . .

[ErikaS]

About three/four years ago have been wanting to wear a black dress and the opportunity presented it self and wow what an fun night.

[Cassandra*]

My first event was in the 1990's. My first wife had this beautiful floral sun dress that just felt like it was calling me. I slipped it on and applied a little makeup and looked in the mirror. Everything just felt right. After this event there was a teddy she once wore and put aside in a bag under the bed. One day we decided to escape for a day trip and the strap was peeking from under the bed( cats must have been playing with it) so I tried it on. felt so goood! She never suspected not to this day. Started wearing VS panties a few years ago and my current wife thinks its weird. My theory is whats the different's between men's UW and women's UW? who's wearing it at the time. Now I've been venturing out and buying my wardrobe.

[Mink]

Does wearing my sisters one piece swimsuit and gymnastics leotard count?

nope!

sorry it does not...

:(

[darci17]

Tried on pantyhose and heels at age 5. Liked it. The rest is history.

[xXxTina]

At around 18 years of age I discovered a pair of leopard-skin victoria's secret panties in a drawer in my dad's closet. It seemed strange to me for something so sexy and exciting to be in a closet belonging to such an unsexy and conservative dad. Maybe it was his? Or a partner's? Either way, they had a hypnotic power over me.. Mesmerized, I completely undressed myself and put them on in my father's closet -- Oh, they fit perfectly! and they felt incredibly silky!

What started as a closet lingerie fetish evolved over 9 years into a full-fledged women's clothing lifestyle choice, in which I now love publicly expressing my femininity while wearing women's clothing! :)

[brynnewilliams]

I was 5. I tried on my mothers pantyhose. Ever since then I loved pantyhose. In my twenties I started wearing dresses, heels, wedges, and such.

[Alex!]

Though I dabbled in crossdressing since my teen years, I didn't go "full up" until April 2006. At the time, I was 36.

[AlexaK]

I tried my mom's panties on a few times, I was probably around 12. At the time, thought I was being weird and such, put it pretty well out of my mind. Little things would popup in the very back of my mind then go away again, forgotten. It stayed that way until after a friend came out as trans and started her transition. Learning more about transgender in general had me thinking about dressing. Was a few more years before denial was finally conquered. That takes me to October, been slowly progressing since then. Came out to a few female friends recently, they are helping when they got time.

[blackcat01]

In our high school, the seniors had at that time, what was called a "Senior Slave day" and There was an auction of sorts in the gym and the underclassmen would bid for the services of the seniors for that day. I was dressed up as a woman for that auction. (Many many years ago)

I don't have any negative feelings at that time. It was later I tried on some female clothing articles.

Found it quite exciting!

[cheryl reeves]

when i was born,mom wanted a girl and went and bought girl clothes,when i was born a boy i had to wear them til i was 2 when my middle sis was born and that was when i started getting boy haircuts which i hate to this day. i experimented on and off from 9 to 22 when i quit for 11 yrs which almost destroyed me and my marriage. ive always been enfeminate but bullys found out quick i was mean and left me alone for the most part.

[gailbridges]

14. It was 1978. About to be 15. Getting ready for sophomore year of HS, and really starting to notice girls.

(clearly I was a late bloomer compared to a lot of you girls. Story of my life)

I'll never forget that day. I even remember thinking that day, "This is one of those impactful, life moments." (though more in teen language, I'm sure.)
I was on my way to the shower in the master bath (attached to mom and dad's bedroom), and saw mom's used, work pantyhose on the floor. I already knew that she had a drawer FULL of her old (runs), laundered hose, (Mom was all about making crafts and did a lot with yarn and nylon) and went poking in there for a pair to try on. Found some, put them on and just laid on their bed.
Nothing much happened at first besides my erection. Didn't know what to do. Just laid there. But eventually started squeezing my (what I later found out was) prostate, and soon climaxed.

I've been chasing the dragon ever since.

While that was the first time involving actually putting something on, and involving masturbation, I remember inklings of things:

When I was 7 or 8, I was in a kid's bowling league. I remember mom and I were car-pooling with some other teammate's in their car, and mom and I were in the back seat. Well, being that age I slunk down on to the floor (remember when using seat-belts was optional) and I was just hanging out down there, and then just hugged mom's leg for some reason. She was wearing a skirt and nylons (real nylons, not pantyhose. This was probably 1970.) I just hugged her leg and my face was touching her knee. I remember then feeling that was something special to touch.

When I was 9-ish, a buddy and I were wandering around in some empty fields near our neighborhood and we found a bunch of junk that somebody had likely just dumped there. We were sort of poking through the stuff, and we found these low heels. I was fascinated with them. For some reason, I said to my buddy, "Maybe we should try them on." I don't remember what he said, but I'm sure he looked at me like I was nuts.

6th grade. 11 years old. (before the obligatory health (sex education) class)
I remember standing on the basketball court, and wondering if it was possible that as we grow older that maybe we change genders, and it was a secret and no one wanted to let me in on the secret yet. My parents never had the "talk" with me. (I'm still waiting, and they've been dead 10 years. :devil: C'mon, that's funny.) My closest sibling was 14 years older than I, and she already had a family of her own. I had NO idea what girls had down there. I thought maybe they had really tiny penises, and they had to have surgery to give birth. I thought maybe boys penises and girl penises touched and pee'd on each other somehow and that's how the girl would get pregnant.

Anyway, it seems the bullets were already loaded in the gun well before I pulled the trigger.

[Heather_Shirly]

I cant remember clearly but the first time i realized i wanted to put something one was finding this blue satin and lae bra, garter belt and panty in the laundry closet of the first house we lived in. I had to be around five or so.

The first time i remember putting on female clothes was a purple satin full slip. I still remember the chills i got from being so thrilled looking at myself and feeling the satin all over me. I was at least 11 then.

Lots of cross dressing ups and downs since then...

[Natasha 22]

Bra n thong around 12. Dressing fully at 14

[susancheerleader]

I was about 12 or 13.
I kept taking and wearing my sisters onepiece swim suit and or her gymnastics leotard.
My mom and sister kept catching me with it on. Or just finding it "hiding" under my mattress and would scold me. I kept taking it anyway but eventually stopped because I was sick of being caught and bitched at.
It was nearly 40 years later when I bought a skirt on eBay. I have been hoarding other types of clothes since then.

[missynicole]

I was probably about 12 or 13 and would be home alone and would put on my mother's bra and panties. Just now accepting myself.......

[girlyboy8]

There are more girls in my family and want to dress me as a girl @ 8 yrs

[Dana44]

I was about 6 or 7 as I remember playing housewife with my sisters.

[Maxie]

I was 11. Took some of my favorite cousins bra and panties.

[Xandra]

I am not passable either, Cindy, and I still don't understand the urge to crossdress. But I love doing it!
I was 12 or 13 - and I never understood it. It still makes no sense to me, as I am not passable at all. If I were pretty, I could almost understand it...

Good luck. I think this is a good group.

Cindy

[LisaKarenAZ]

I was around 9 or 10 and I had gone over to visit my best friend who lived next door, and he wasn't home. It was just his mom and sister home, who told me to wait if I wanted. His sister was playing dress up/house, and told me to join her tea party. What I didn't know was that it was a "girls only" party, and she proceeded to have me dress up in a pretty dress, underwear, training bra, and makeup. Although she was 2 years younger, I was small for my age and we were the same size.

After playing dolls for a bit, she and her mom thought this was cute, and walked me to see my mom and her friends with at were visiting. They all giggled, said what a cute girl I was, and my mom telling me I shouldn't wear someone else's clothes, and to go change.

Through the years, I was caught plenty of times by both my parents dressed up.

[cd_dominique]

I don't remember my age, but I was fascinated by my mom's and sister's underwear drawers. When I knew they'd be out for a while, I'd sneak into a drawer and put on a bra just to see what it was like.

One night when both were out, i had gone into my sister's closet and put on just pantyhose and a dress (wearing men's underwear) and was checking myself out in the mirror. Unfortunately, the phone rang and my little brother, whom I was babysitting, answered the phone as I tried to run down to get it first. He saw me dressed as i was and actually said into the phone "You'd better get home, there's something weird going on", referring to me.

[Angela Marie]

Not sure how you define crossdress. I began wearing my moms tights when i was 11 or 12. Loved the feeling and to this day I love tights and pantyhose. I'm also a runner so when running tights became popular I wore them even more. It wasn't until my late 40's early 50' that i began dressing more fully. I was terrible at makeup. I had my first makeover when i was about 52 or 53 and looked awesome. A bell went off in my head and i've been dressing ever since.

[Kristie23]

I was 16 and house sitting for my girlfriend as her family was overseas. I'd always liked her gstrings so started by trying one of them, then I had to see how it looked under every piece of clothing of course.

Next thing I know I'm wearing a pair of her sisters heels and dressed up in a ****ty mini skirt and nice top.

[Brandy]

When I was little, I played with my mom's slips and loved how they felt. Eventually, my parents said I couldn't do it anymore and took them away and I forgot about it until puberty (13ish) when those memories came rushing back suddenly, and I felt a great urge to try things on again. I then started wearing my mom's panties, girdles, slips, and night gowns when I was home alone and have been doing (now with my own collection) for 20 years.

[kryss.cd]

I was 14 and moved into my sister's house. There was a drawer full of her old lingerie in my room that I explored. I tried everything on and didn't touch anything again until I was 16 and my girlfriend at the time dressed me in her lingerie. I've been underdressing on and off since then.

[Teressa]

I must have been 8 or 10. Saw one of my mom's full slips hanging on the closet door and something told me to try it on. OMG I couldn't stay out of her closet from then on. Still have a thing for full slips.

[Karen RHT]

I was 11 with Halloween coming up. We had moved into another house recently, and a lot of stuff was still in boxes. I always enjoyed Halloween (still do) and always wanted "something different" for a costume. My mom knew how much I enjoyed Halloween, and frequently used her sewing talents to help make my costume a reality. We were going through boxes when I came across one with some of her things in it. Looking at them, the thought of dressing completely as a woman entered my mind. Told mom that's what I wanted to do. She thought about it for a moment, said it would take some work if I really wanted to pull it off, and asked me if I was sure I wanted to put in all that effort. Without hesitation I said yes, which started me down the crossdressing road. :)


Karen

[Sandie70]

I don't know if this counts, but my mom really wanted a girl. So, she let my hair grow out and dressed me in girl clothes up until I was six years old.

From the pictures of me in little, frilly dresses with ribbons and bows in my hair, I was really cute. Prettier than my GG cousins.

Guess all that was quite prophetic. When I look at those pictures I regret that mom didn't let me remain a girl. But in those days, that would not have been acceptable.

Sigh.

[Marie-Claude, France]

I was 11 or 12 and I was playing with my cousins; since we were all boys I declared that I would be a woman and I dressed with some of my mother's clothes. The rest is history.

[charlenemichaels]

My 1st CD expeience was around 9 years old when i went to the bathroom and saw my grandmas silk stockings drying on a rack.
They were dry so i carefully removed my boy stuff and pranced in the BR with them.
Instant attraction, instant lightning! Only trouble was i forgot to lock the door and got caught.
Grandma made no big deal of it and never told my folks.

She gently admonished me to leave her things along.

:)
~Charlene

[Piora]

I was 14 and moved into my sister's house. There was a drawer full of her old lingerie in my room that I explored. I tried everything on and didn't touch anything again until I was 16 and my girlfriend at the time dressed me in her lingerie. I've been underdressing on and off since then.

Kryss, I had a similar experience to yours. When I was about 15, my parents and I were staying with relatives while vacationing in the UK. A neighbour of my grandmother offered to provide me accommodations, as there wasn't really enough room for us all at my grandmother's. It was her daughter's room, and she had just got married, and moved out. She had not yet picked up any of her things that were in the dresser. As my grandmother's neighbour was a widow and worked during the day, I found myself exploring the contents of the dresser. This was in the mid-sixties, so it was all stockings and garter belts. The only colour was white back then, also. Anyway, I dressed in stockings, garter belt, bra, panties and slip. There were some shoes, but far too small for my feet. I spent many a morning looking at myself in the full-length mirror. I was very sad when we left for home.

Oddly enough, and believe it or not, I never pursued dressing again until I was married, and in my early thirties. Since then, I've had the occasional hiatus, but I always had the desire come back. When it does, I indulge even more than the time before!

[Heelios]

My first CDing experience was trying on my friends mums heels which she kept in the porch at the front of the house. I used to deliver the local newspaper there when I was about 14 or 15 and one time I was there and they were out so I took a pair off the shelf and forced my feet into them - they were way too small but it felt amazing!! The CDing thing has slowly crept up my body from feet ever since!

[Michelle_Diane]

I was about 9 or 10 and my mum had some tights hanging up to dry. I tried on a pair and loved the silky feel and how they encased my toes. It just grew from then on.

[Wandacdmn]

I was 16 years old. I matured very late so I was a smooth boy. I tried on my mom's "hot pants" and I was totally smitten with crossdresser desire...

[StefaniLara]

I have a vague memory of wearing my mother's dress when I was around four years old, then immediately being chastised for it. I conformed to societal expectations until I hit puberty when I started to dress in private. It wasn't until college that I started to experiment.

[Cynthia T]

1961. I was 11. Had no interest in girl clothes. Then, one evening home alone, I was reading a book that mentioned in passing a woman in high heels. I was immediately turned on, went and got a pair of my older sister's heels and put them on. Scrounged in alleys for more women's clothes, until I was old enough to buy.

[Lilblondecutie1407]

I knew I had a fem side around 5. By kindergarten I already envied the cloths the girls got to wear. Although I can fit in with the guys, I seem to gravitate towards the girls. I seem to feel more comfortable in a group of girls. Once I have been there for a short time they seem to accept me as one of them in our conversations.

i had a very similar experience but did not start dressing with a better understanding of who I was until I was 18-19 ish and started really dating, but once I started it was full steam ahead.

[Li'l Miss]

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.

[ChubbyLeahCD]

Not sure when but when I was in kindergarten, I went to a school that was small and ran by a few people my mom knew.
The owner was brunette, tanned skin, sweet with cute feet. How do I remember her get? She wore sandals that I remember liking and she used to stand in a girly way and I remember copying her discretely.
That same school offered ballet for the girls and I wanted to do it to be with them and to have tight ballet clothes, even if they were male clothes.
Then I remember spending the night at my grandma's house and seeing her panties drying in the shower and always putting them on...
Fast forward to puberty, with my parents letting me stay at home alone more often, I started digging my mom's clothes from the dirty laundry basket and wearing it. I know it sounds disgusting but the excitement was such that I knew it was safe to let my juices so to speak, get the dirty panties dirty.
Clearly remember when I was around 12, trying on my mom's teddies and remember putting on her silk rumper pajamas and her flip flops.
Then in late middle school I stated going for her closet. Tried dresses, pants, bathing suits, shoes, everything.
Almost got caught one time: she came home and I had locked the door to the garage. She had an opener but no keys. She knocked but I was way too caught up in Leah's world.
She called the house and when I picked up she was yelling for me to open the door...and here j was in her lingerie.
I scrambled to put it all away and when I opened the door she was asking what was I doing in her room because we had a control panel for our alarm in the garage and she could see the zones I was in.
I don't remember what excuse I gave her but she never brought it up. All that continued and then I thought being a CD was too weird and I buried until. Then as a junior in college I bought used outfits and lingerie from an amateur actress called PussyCat on SouthernCharms.com and I used to dress up in my room in my apartment.
Lost all that when an ex girlfriend who liked me CDing threatened to out me to everyone when we broke up so out of fear I tossed it all away...
Then bought more stuff from her and still have it today. As of today I wear my stuff, and my wife's that fits me still and have bought a few things myself, cheap so she won't suspect the money leaving the bank.

Sorry I gave more than what the topic asked for but I just caught myself walking through my entire timeline as Leah and couldn't stop.

[Kimberly Adams]

I was 6 or 7 yrs old. I remember trying on my moms bras, way to big but oh well it seemed ok. I also remember around the same time cutting the bottom half of a t-shirt off and putting it on like a skirt with a belt. So fascinating this starts at such a young age.. I can still remember the exhilaration.

[franlee]

My 16th birthday, I conned or got conned on a made up bet to get out of my clothes and my Girlfriend out of hers. It worked to well, we did a complete swap from the skin out. And I was smitten-ed from then on.

[Glendy]

I think I was around 12 years old I used to see my sisters wearing their sex night gowns.

[Belle Cri]

I was raised in Europe, specifically in Italy, and there it was quite common for young children to wear some form of, well not a frock really, but sort of a dress. So, pretty much before I ever got out of diapers. What a surprise LOL.

[rachey77]

It was probably down to my sister actually!!! she dressed me up in her yellow party dress, I thought to myself; this is so much nicer than pants!!

[Alice_2014_B]

First time trying on a single item, that being high heels, I must've been around seven.
First time fully en femme was just about a year and half ago, early 2014.
:)

[veola]

12 -13 years. I liked to wear clothes and shoes older sister. I greatly enjoyed.

[Xandra]

Love your story!

[Mayo]

I tried on some of my mother's underwear and a bra when I was around the age of 10 or so (I think I said ~8 in an earlier post but I don't remember exactly) and beginning to get curious about the differences between men and women. At the time it didn't make any particular impression on me and I didn't put on female clothing again until recently, after I'd been actively questioning my gender for a year or so. However, even during my teens I was aware at some level that I had some feminine inclination, component, tendency or wish. I did realize during my pre-teen and teen years that I had a sexual interest in boys as well as girls but, that said, I realize that gender and sexual orientation are not necessarily consonant and I don't know that being bisexual is in any way related to my gender identity (which is still in flux).

[Valerie Beards]

I recall first wearing my mom's clothes when I was about 11. On school holidays and I was lying in bed thinking about what it would be like to wear a woman's clothes. This topic had been something I had been musing over for a while. I suddenly realised I could find out. Lept out of bed and into my parents bedroom. Within minutes I had put on mom's pants, bra. tights, skirt, blouse and also her panti girdle over the tights/pants. This was the late sixties and I had observed mom getting dressed and seen her wearing two pairs of pants. Curious I manoeuvred to look up others womens skirts and saw similar two panties..or as I found out a panti girdle on the top.. I must say I really liked wearing all her clothes and in particular the girdle. Still have one in my collection...47 years later. Needless to say I have never stopped since...

[lostinmyworldcd]

At 14 . My sister went off to college and left her room pretty much as it was when she was there . Hers and my bedrooms were in the very corner of the basement , away from our parents . i first started putting her pantyhose on . Then her heels . Then I had to dress in it all . I even put make-up on and polished my toes and nails as we had a bathroom on the other end of the basement . I would play dress-up all night long into the early morning hours around 5-6 am . I spent many a night prancing back and forth thur the basement , trying my best to walk sexy in heels . Although it was somewhat a rush to me , sneaking around , I enjoyed being "pretty" . I have spent the rest of my life , going back and forth , dressing up. I've bought alot of clothes and shoes , only to end up throwing them away or piling them in a burn pile . At 47 , I don't see myself stopping ......

[Midasgirl]

I had always loved the feel of silky fabric, be it the edging on a fancy blanket or the label on clothing, and around the age of 10 or 11 I began to ponder what it would feel like to be covered in such material. I remember feeling quite jealous of girls wearing satin blouses or dresses and wished I could be the one wearing such things, despite being a boy.
Given this interest, it was inevitable I'd start wearing my mother's clothes when I was alone at home.
The first thing I tried on was a white satin nightdress, an ankle length one. It was one night when my parents had gone out for a couple of hours, and I remember staring at myself in the mirror and running my hands over the silky fabric. It felt so good to be wearing something so girly.
That Christmas my mother received a pair of satin pajamas as a gift, and I wore them anytime I was alone. I absolutely loved those pjs - I'd stare at myself in the mirror and fantasise I'd been turned into a girl. It helped a lot that the pjs in question were a very girly shade of pink.
After that it was satin blouses, then satin blouses and skirts. I've no idea how my mother never realised I was borrowing her clothes so often.
Those early days were over 20 years ago, and I'm here typing this while wearing a glossy satin blouse and skirt. I'm pretty much addicted to wearing satin now ;)
Although these days I buy my own and don't steal my mom's anymore!

[Elli87]

In pre school I'm sure Ms. Audry knew I was a fairy. Wearing woman's cloths in the dress up section, wanting to be a ballerina....playing with dolls. Now years later I look back and say ah I was just a little kid.

[MirandaAlicia]

I'm pretty sure I was maybe 5 or so, big enough that I could wear a couple of yard sale skirts (the sort with the wide elastic waistbands) as dresses. I had a collection of salvaged yard sale clothes at my grandma's house, and fostering creativity we'd roleplay fashion show and I was the runway model, and the lighting engineer, and the cameraman, and all sorts of other roles, with grandma the announcer and judge. (it amused her while she was recovering from numerous hip surgeries and was pretty much bedridden). I also had a cache of clothes at home that I actually would play dressup in with the other neighborhood girls, who didn't think it odd at all. My dad hated it though, but I think more out of the fact that my sister took such an active role in things and he disliked her treating me some of the way she did. I was so -mad- when my clothes got thrown out...

[Chancey289]

I think I was 9 when I first tried on women's clothing. I don't know why I did it, I just wanted to. It wasn't until I got older I started doing it more often and going full blown girl mode.

[Robin414]

Apparently I was fascinated by women's nylons since before I could wall so I'll say conservatively...about 2...yah I was in the 'gifted' class 😁

[Diane Smith]

In pre school I'm sure Ms. Audry knew I was a fairy. Wearing woman's cloths in the dress up section, wanting to be a ballerina....playing with dolls. Now years later I look back and say ah I was just a little kid.

I'm impressed that she tolerated it. I got a sound reprimand from a preschool teacher when I tried to handle some of the clothes and shoes in the girls' dress-up section. It was clear to me from that moment onward that wearing a dress and heels was something that boys are never allowed to do. It must have been pretty traumatic to me because I still remember it clearly over 50 years later.

- Diane

[Staci G]

I think I told the story maybe not, I was young could have been 5 6 anyway I found my sisters panties in the hamper and put them on. I went into the living room sat on my moms lap and she immediately knew. She told me I cant wear them and to go take them off. I found a bra in my moms room one day went to the boys club, must have been around 1965. There was a guy there asked my why I a m wearing a bra I don't remember my answer. Anyway I progressed to sleeping in my sisters and cousins panties and silky pajamas when I got my hands on them. My brother caught me and asked why I said I like it and he never told, never questioned any of it. He was my friend one I always counted on. He stole a full slip one time off a clothes line for me and said it should fit better than moms or my sisters. I'll never forget the first pair of pantyhose I bought myself, they were jade green and MINE!! Haven't found a pair like them since

[jaerina96]

I was around 9, don't remember how it started! Just stuff from out big box of Halloween costumes, my sister and I were pretty close in sizes then. When I hit middle school and had actual home alone time because of the bus schedule I started borrowing old dresses my mom had forgotten about and trying to look like the girls in school.. Of course I got found out and got the big lecture about hellfire and stuff after a couple years I stopped because it was super humiliating and I couldn't get away with shaving my legs without getting caught so I couldn't do it till I lived by myself after college.

[lisa_vin]

Around 3 or 4 years old with my moms nylons and slips.

[Melanie 0339]

I was about 13/14 we had a spare room which was full of alsorts while I was being a nosey teenager I found a suitcase which was full of old clothes inside was a pair of stockings and a suspender belt. I'd seen girls in certain magazines wearing these before and I liked what I saw so I thought I'd try them on to see if wearing them would create the same feeling as seeing girls wear them, and omg it was better then I could have imagined they felt amazing on my legs and the straps rubbing against my thighs as I walked around in them since that day stockings and suspenders are still my favourite item of female clothing and it's very rare for me to dress without them xxx

[Jane G]

Tricky one. I used to dream a lot about being a girl from a very early age but I don't recall dressing up until I was 6 or 7.

[SillyGirl]

Probably 9 or 10 the first time I tried anything on, I remember really becoming enamored with girl's clothes around 12 or so. That was when stirrup pants were a big thing and my step-sister came to visit her dad for a month in the summer. I was constantly sneaking into her stuff and wearing her panties, stirrup pants, anything else I could get my hands on. I initially just wanted to know how the stuff felt but then I liked the way it made me look and feel and it escalated from there.

GG's don't realize how good they have it. One of the things about them I'm most jealous of is how with a change of clothes, hair style, makeup and accessories, they can look like a completely different person. The conservative business woman turns into the night club sex pot in under an hour, etc. Dressed as a guy, that's pretty much impossible to accomplish.

[Chloe1955]

I think I was about 11 or 12 when I used to sneak into my older sisters room and fondle her taffeta half sips, I used to take them into the bathroom and slip into them it felt awesome. My mom was a sewing machinist and used to alter/make clothes for friends and she made an amazing silky dress for a friends daughter and hung it up on the back of the lounge door. When my parents went out I tried it on I adored the tactile feeling against my skin it was out of this world

[melb24male]

I remember when i was around 10 years old, I tried on my mothers Blue one piece bathing suit. I remember instantly getting hard. As i watched my **** push against the Bathing suit. Was hooked ever since

[Jennie2]

How could I not remember something so life changing.
I was about 7, age doesn't matter, It was a small light blue full satin slip, I just had to try it on, it felt so right, I was hooked. Now I am just about to slip into a light blue cotton nightie and white cotton panties, feels so good to sleep en femme.

[QueenShorty]

Was about 7 or 8 when I first tried on my mother's high heels. I wasn't really interested in clothing until my teens. Around 17 was the first time I tried on lingerie. My mother had a box of unused lingerie (her and her friends used to sell them) that sat in the closet for years. I've been hooked ever since I put on that silk camisole :).

[Kaze_]

I remember my mother caught me with her panty hose when I was like ~5 actually. One of my first memories is from around that time. It was asking for one of my mothers dresses and getting shot don't pretty harshly. >_>

Dunno why I crossdress but its something that's been with me from the start.

[Sandra119]

I remember wearing my mums underwear when I was about 9 or 10

[Sexy_Stephanie]

When I was like ten I tried on my sisters skirt

[vicky77]

when I was 6 one I was in my sister's room, I saw a summer dress of her and I tried on...I still remember the scene.

[ashley-fl]

I would wear my sisters panties when I was about 5-6. I liked how hers looked better than mine, but I didn't start wearing other female clothes till I was about 10-11 and have been dressing ever since.

[alison301]

The first time I can remember is about 5 or 6. When I was growing up we were quite poor and I remember I had to wear a pair of girls bikini bottoms (kids) but frilly, so we could splash around in a little paddling pool one of my neighbors had set up in the garden. My mum never had the money to buy me some so my neighbour lent me her daughters and I still remember her saying it would be ok as I was so young.

[ashleyjane15]

The first time was when I was really young. I know I was younger than 5. I tried on a pair of my babysitter's panties. Later on I started wearing my mom's clothes when I was home alone.

[boots]

I was attracted to my aunts fur and suede coat when I was 4.I loved the feel and never quit dressing up since then

[Quintaseg]

In started when I was 35...late starter. My first dressing session was in a festish place. The lady dressed me up..... It was out of world feeling. I felt like I am me but not exactly me. I can recognise my voice but not myself. Its an awesome feeling.

[KrisB]

Personally I blame a Perfect Storm of the old Batman TV series and early 70s womens' fashion!

It's about 1973 and I'm 6 years old. I was totally into Batman and decided I had to have a Batman costume. At the time brightly colored tights were a big thing in fashion and my 18 year old sister had a drawer full of them. I grab some black, gray and yellow tights, find myself some scissors and start snipping away. When I was done, I realized I made a huge mess I couldn't talk my way out of easily. I also realized the tights were making me feel really, REALLY good for some reason! Needless to say I got caught.

I periodically wore tights and pantyhose in my room but that was it. I fully dressed up for the first time when I was 47. Sometimes I think I'm not so much a crossdresser as a hosiery fetishist who put up with all the other female clothes to get a chance to wear stockings in public in a (reasonably) acceptable way!

[Robin414]

When my wife found a pair of panties and a bra in my truck! JUST KIDDING, I don't have a truck! 😂 Just reading some serious threads and needed a laugh, sorry!

[julie marie1]

When I was in my teens one of my sisters and her girlfriends decided it would be fun to see me in a dress. Sometime later I started wearing my mothers clothes. For many years I was a secret crossdresser, wondering what was wrong with me and being ashamed of myself. More recently,thru the internet, I have come to enjoy myself and really make and effort to pass. So, maybe the first time I realy crossdressed was when I went into a bar and asked for a glass of wine, enjoying myself although the others present knew I was a guy in a dress.

[Infused]

When I was 6 or 7 I looked in my sisters underwear drawer and tried on silk panties. As a teenager, almost daily after school I would try on a pair of my sister's panties, she had lots of sexy undies. I didn't know what a thong was until I found one of hers and when I tried it on, that was a defining moment for me. For years I just loved panties and never really thought about dressing up more. It wasn't until my 20's that I was able to acquire and keep my own clothes. Now I dress head to toe, I like the way I look as a girl, and love the way I feel.

[Xandra]

Love it. Thanks!

[Bobbi46]

Properly? about three years ago, knowing I could do it and not worry of getting found out by family etc.

[VictoriaBabes]

I was 11 and I first started with undies. Had an older sister and I always had a fem shape so it just seemed natural. I used to wear sexy type of undies and loved mini skirts. I stole a few mini skirts from here and hide them in my room lol

[Scarlett Viktoria]

It was about 5 or 6 years ago while my wife was away on business. I always loved womens clothes and became curious to know what they felt like on. So I siezed the opportunity and tried on every dress and pair of heels in the closet. I loved every bit of it from then on.

[PegyL]

I started at eleven putting on my Nanas bloomers, in those days there were only two kinds of colored panties white and pink. While I could pass many years ago, if you were found out you ended up in jail if you were lucky, other wise you had the crap beat out of you by those others.I often wonder today what does and old lady do today with all you young lovely ladies present. OH MY PegyL

[MissDanielle]

8th or 9th grade. Off and on since but it's due to a woman being stuck in this body if I had to guess.

[Sarah.Jane]

wow, i love this thread.
I think I was about 9, I stole some of my little sisters clothes, a slip and skirt, luckily she was bigger than me so I could wear them, I used to steal clothes when we visited people.
Now internet shopping doesn't help my bank balance.

[Jacqueline StGermain]

Before kindergarten ( like 5?). Tried on my cousins stuff , we remained the same size for the next 25+ years,
We look almost like twins ( she doesn't know ), my sister and I don't look at all like siblings, plus her stuff was a little too small for me.

[kittie60]

I was 10 , and had a dress and tights in that were my step mother's. Wow, 50 yrs ago. Been doing it ever since

[girltime]

I was 11 years old. Sneaked my mom's panties and a bra. Didn't know at the time this was a lifelong thing. My wife surprises me with new dresses at birthdays and holidays. She knows this is something that kind of defines who I am. I don't go out dressed up.. But I do often sleep in my panties and a nightie.. Always look forward to opportunities to get some dress time.

[maryelizabeth]

I was around 10 or 11. Growing up with older sisters always made it easy to try on different things.

[AltairaMorbius]

Around 7 here, we lived in a small house with one bathroom, where Mom would wash and dry her delicates as she called then. I remember on the weekends her soaking her panties in the sink then hanging them to dry, along with her heavy duty bras in the bathroom. One night before my bath I looked in the hamper and found a pile of her panties ready for the wash. I remember to this day that my heart was pounding as I stepped into them and pulled them up. After that it became an on and off again thing for the next 50 years, lately it is mostly on.

[shining-sera]

I was around 11 or so when I first tried on a pair of my mom's underwear. My parents found out I took it and had a long conversation about how wrong it was for boys to wear girls clothing (my parents are pretty conservative). Needless to say, my family still doesn't know anything about my habit.

[Jamie390]

I was probably around 12. I always liked swimming or showering in clothes. One day when my parents weren't home, I got the idea to wear mom's bra and underwear under the clothes that I was showering in. That progressed to showering and bathing my mom and sister's clothes and bathing suits.

[Scarlett Viktoria]

Am I the only girl that started in her late 20's? Lol.

[MsMissy]

Around age 13, my Mom wanted a girl, imagine growing up knowing that - conflicting thoughts. Started with a me and mom wearing the same size 12 pants, then it progressed to her painting my face with makeup then it went to white bikini undies that I tried on, it was a fetish for about 7 years, (got in trouble once, parents thought i was gay and grounded me, my Mom hasnt changed her idea of anything my Dad doesn't care one way or the other.

I started buying my own stuff around age 16-17, the fetish disappeared after I went out in public a few times. I purged many times and then started hording certain things, went thru styles like a teenage girl changes clothing.