When did you first crossdress?

[CherylFlint]

Same with me, somewhere around 4.

[NANNETTE]

I was twelve years old. It was my first year in high school and I was so envious of the girls in my class. At the time it was the fashion for girls in school to wear tights under their school socks. Oh I how I wanted to be like them, it was frustrating beyond belief. At the end of 1972, I wondered if my Mums tights would fit me, to my surprise they did. At first I wore tights under my football shorts, I imagined they were hot pants. It was the era of the go go boots and and tan tights. I saw a picture in a Pop music Christmas annual of the lead singer of Middle Of The Road in boots, I so wanted to be like her. Eventually I started trying on my Mother's skirts when my parents were out, a lovely experience I felt so much like the girl I always wanted to be. I wore my Mother's things for eleven years before I plucked up the courage to buy my own tights in Woolworths in 1981. Once I gained confidence I would buy dozens of pairs of tights in department stores.

I think the boys in my school knew I was different from them they used to tease me and call me a girl, I used to pretend to be annoyed but secretly I liked it. One boy said I shouldn't be wearing boys clothes in the gymnasium and I ought to be with the girls wearing leotards. I was thinking the other day that it secretly excited me, I so much wanted to be a girl. I opted out of subjects like Woodworl and Metalwork in favour of short hand and typing. One boy said I went to the girls typing classes because I wanted to be a secretary with a mini skirt who would bend down to show their legs to the boys, he was only joking but it really was what I would have loved to happen.

[Michelle V]

I must have been younger than four, I remember it because it was way before my parents divorced, my female cousin who is my age came to my house to visit and left her very pretty jacket in my room, I snuck upstairs to was it an was caught by an older cousin, I was very embarrassed and it left an impression on me, however, I've never stopped. Much as I tried I've never stopped, I just wished I had come to terms with who I am when I was younger, this way I believe I would be in a bette place with my self.

[SaraNZ]

When staying at my grandmothers I use to want to put on a small purple dress she had (dont know whos it was, she only had boy grand kids at that point) I must have been around 5 I guess. Moved on to trying on mums dresses and boots (no sisters - I imagine I could have progressed quicker if that was the case :) ), even pushing her earrings through my lobes when I was about 13/14 after school...only for a minute or 2, they'd have to ok by the time mum got home haha.

:)

[Jennifer in CO]

Somewhere around 5-6? possibly earlier but I don't remember it. As a very sickly child, if it were a real cold night out I was put to bed in my older sisters long flannel night gown that had full sleeves and a high-neck collar. A funny to this is there was a home movie I saw a long time ago. Sis and I come stumbling into the living room on Christmas morning, both of us in long white flannel (frilly) night gowns....movie suddenly stops. Next frame she's still dressed the same but I'm in a dark blue floor-length robe (also my sisters) but it wasn't "girly", just long (covering up the gown). I've seen many a picture of me from the early 60's in my sisters hand-me-downs (shorts, rompers, etc) playing in the back yard. Thinking about this, I'm not sure why my Mom was so upset when she picked me up from my cousins (when I was 10) after spending 3 weeks with them...all of it dressed as a girl?.?...hmmm

[DebbieL]

When I was 2, I made a "dress" out of a dry cleaner bag. Mom thought it was cute and even made a belt out of some of the plastic. Dad freaked out because he was afraid I would suffocate in the plastic.

When I was 4, me and some other girls put on a "Circus". They dressed me up in white tights and a leotard and I jumped off the garage roof into a pile of mattresses.

The first time I was fully dressed entirely in actual girls clothes I was 5. I was playing Barbies with 4 other girls and we were trading Barbie clothes. Then the girls started trading clothes with each other. One of the girls wanted to try on my clothes and the girls decided to dress me up. They had me change everything. I was wearing panties, tights, Mary Jane shoes, a pretty dress, and even some jewelry. We played together that way for a few hours until the girl's mother came home and saw me in the dress. She freaked out, made me change into my boy clothes, and told me never to come back again. The next day, none of my friends, nearly all of the girls in my class, would play with me. The teacher told me I had to go out and play with the boys. The mother had called all the girls' mothers on the PTA as well as the teacher, to make sure that I wasn't allowed to play with girls anymore.

I kept dressing on the sly all summer, dressing in my mom's clothes, digging them out of the clothes hamper. Mom finally caught me and bought me a pair of tights, but dad insisted that I get a matching T-shirt and had mom make me a cape, so I could be "Superman" instead of Wonder Woman. Big let-down.

From that point on, I lived in "stealth mode" for nearly 20 years. I came out to my first wife when we moved in together, but before we were married.
I didn't go public until I was 34, and a year later I was seriously considering transition. After my dad died, when I was 55, I decided to transition.

[Xandra]

You make a great point about wishing you'd come to terms with who you are at an earlier age.


I must have been younger than four, I remember it because it was way before my parents divorced, my female cousin who is my age came to my house to visit and left her very pretty jacket in my room, I snuck upstairs to was it an was caught by an older cousin, I was very embarrassed and it left an impression on me, however, I've never stopped. Much as I tried I've never stopped, I just wished I had come to terms with who I am when I was younger, this way I believe I would be in a bette place with my self.

[SamBrook]

I was 6 when I first tried on some of my sisters panties. They felt so good I couldn't get enough so I tried her leotard too. I remember even sleeping in those panties I had and now I am still the same way

[Jessica S]

I was helping my mom sorting socks and a pair of my mom's Kneehi's were in the pile, I was around 4 or 5. Something clicked and I had to try them on. Then came pantyhose then panties and everything...

[Rebecca Cross Bracer]

I remember having an pantyhose fetish at an very early age. I think I was 10. I loved The way they looked on women, how "see through" they were, The shine they gave off and how cute they made feet look. It was within that same age that I wanted to know how they felt on me so I stole a pair of my mom's. They didn't look as good as they did on other women (to find out it came down it brand and such) yet they felt amazing! There was little turning back after that.

Almost the same story for me, but I loved the look and feel of the pantyhose and progressed from there. Slowly at first, mostly just pantyhose for a few years, then my sisters' bras and dresses, now all out when possible.

[Karen_the_Cutie]

i wasnt even in kindergarten yet, so i guess like 3 or 4. first thing i wore was my sisters pantyhose. also my moms bra (which was waaaay too big for me being so young. lol) and my sisters nightgown shortly after, but not same day. I wish I had been open about it then, I even knew I wanted to be a girl then. I remember playing with my grandpa and asking him to call me tiffany, cause that was the cutest girl in my class and i wanted to be like her :3

[Christine.Lolita]

I have memories of wearing my mother’s clothes at around age 12. If I had a sister I am very sure I would have been wearing her clothes much sooner.
I bought my first dress when I was 32. It was a French maid dress I got from “LD Fashions” an online shop that sells sissy dresses, little girl dresses, and maid dresses. I had no shoes, makeup or wigs.
I wore the dress for about 4 months and when I had to leave home for work, which was my own house, I was so worried that someone would find it I threw it out before I left.
In hind sight that was a silly thing to do.

[monica.missil]

I was 12. Put on mom's bra and girdle. Then put on her nurse uniform.

[Xandra]

I love the progression!
I was 12. Put on mom's bra and girdle. Then put on her nurse uniform.

[renee elizabeth]

started when i was around 7 or 8, i started coloring my toenails with markers because i wanted them to look pretty, then i started to wear my mom and sister's clothes and makeup, never was caught

[DaisyDell]

Wore costume dresses at my neighbors house when I was probably 7. We would "force" each other to wear them and dance around and act like a girl. Started regularly wearing moms hose and lingerie when i was probably 10 or so. I would put on entire outfits with bows in my hair and model in the mirror. Didn't dress for a long time before and after i got married, and I buy my wife lots of lingerie. I just put on her swimming suits a few weeks ago and it all came rushing back. I would say it felt like another "first time"

[Gia Villafana]

Seems like 12 is a very common age! That's when I wore my mom's underwear and stuffed using tissue and later baggies filled with water. I stole bras from various family members and friends. When I turned 16, I was able to drive and get my first wig from a black beauty store. My first forms were those little silicone breast enhancers.

[ringedjohn]

I tried on one of my mother's girdles when I was around 12. Shortly thereafter I bought a light-weight pantie-girdle for myself. The fascination with girdles/pantie-girdles has never left me. Bought my first corset at around 22 I think - and about the same time I tried on my first bra. Nice memories.

[Princess Grandpa]

I have been giving this a lot of thought over the last few weeks. The first memory I have is coming across mom's teddy. I guess I was 12 or 13. If it was going on before that I just don't recall. I have been wondering of late if maybe mom played dress up with me in retrospect she clearly wanted me to be a girl. If so, I would like to thank her.

Hug
Rita

[Seana Summer]

I first tried on my sisters pantyhose at 3 or 4. I don't remember for sure but I know I wasn't in school yet. Don't recall trying anything else on until I was probably 8 or 9. When I was 10 or 11 I found a box of nylon stockings! WOW that was the best discovery ever (at the time). At 14 I was dressing up, strictly in private, in nylons, panties, bra, slip and dress, mostly from my sister and other relatives. Then I gave it up until I was out of school, I recall purging at least once:( One time I dug a deep hole and buried my cloths!!. Somewhere around the time I broke up with my girlfriend at the time, several years later, I started getting the urge to start again, this time I bought my own cloths.

Ahhhh the memories :):):)

I will now reminisce the rest of the day!!

Seana

[Christina81]

I was pretty young. I was in that age of cuteness of 5. I wore my sister's dress and went down to my mother with it. I cant remember what she said though. I didn't take much notice of women's clothes for years after until my sisters grew up and instead of playing with my older brothers, I played dress up and played with my younger sisters. Now I have my own clothes and love who I have become.

[Courtney . J]

dont remember my age , probably 4-6yrs old , but for some stupid reason my brother talked me into wearing a pair of my moms panties for a day ,. i think we made a bet or something that i would get something if i did the task

then a few yrs later i stole one of my other brothers metallica tapes ,. he found out and the only way he would let me keep the tape is if i (again for some stupid reason i have no idea why) would let him put lipstick on me as a joke or to make fun of me , or whatever .




funny thing is they had no idea that i actually enjoyed these things and them feelings have never left me and have only grown stronger


if only they knew what they started , idiots ... lol


:heehee:

[ange_o]

Probably was around 6 or 7 years old. Was in my parents room and tried on one of my moms bra's that was lying there. Coincidentially was also the only time I have been caught dressed.

[Hannah W.]

I was about 12 I guess, like many of us I starting trying on my mothers clothes. Felt so wrong & elicit...but so right too! Feelings disappeared in my early 20's but have returned recently & now I'm out to my wife, feels so good that I can actually act on my feelings!

[Claire Cook]

Probably around 4 for me when my mom let me play "dress-up" in one of her old dresses. Soon graduated to getting into her lingerie drawer whenever I could -- girdles, bras. Shared the guilt many have expressed here. but it just felt right. My fave thing was a crinoline -- I loved wearing that, and have not seen one like it since.

[GeorgeA]

I copied my post from a few years back as it is relevant to this discussion.

When I was about 4-5 years old I searched my aunt's dresser drawer where I knew she had a bag of candies, next to them were several of her nylons. I tried to pull them on my legs but of course they were too long for my short legs. I tried another and another but none would fit.
Many years later I would sneak my mother's panties and nylons and they were much better fit this time as I was about 12 or 13.
It was only when I started to work that I acquired a collection of lingerie from a mail order catalogue.
To this day nylons, garter belts & slips are my biggest attraction.

[Missy]

I remember wearing my sisters under cloths to play female roles with the boy next door who play the male role got hooked on wearing bras and panties and every thing else at that time in the mid to late 60's

[Quksilver420]

Do you remember the first time you tried on an item of women’s clothing?

I remember putting on my mum’s fake fur coat around age 7 and getting a thrill from my appearance in the mirror. I knew at once that this was part of my future. How about you?

I really don't remember my first time. Only thing I can is that I was a bed wetter. In preschool, after naps I would have wet clothes and 90% of the time no change of clothes. Most days if I wet myself I would go home in girls under ware. Cross dressing just snowballed from there.

[TonyaV]

I may have been born with. I can trace it back unit I was a young child.

[Xandra]

I have really enjoyed reading all the replies. Please keep 'em coming.

[Patty]

Early grammar school 5th grade I think. It was been soon long ago.

[Robin777]

I believe it was 12 or 13. I remember starting with my mother's panties and going from there. It all started with panties, then putting on a bra and slip,then a dress. It went on from there. I remember when I was younger ,I always liked looking at the sears and penny's catalogs. I always went to the women's section. To this day I enjoy shopping for ladies clothing more than mens.

[Trisha65]

Apparently shortly after my birth. I have three older sisters and I have seen pictures of me in hand-me-down sleepers that are obviously girls sleepers. After that, I can remember my sisters dressing me up probably from 3 on. Never objected and never took the clothes off until bedtime.

[regina young]

When I was a very young 6 or 7 year old boy we did not have much, but neither did most of the kids I knew so we really did not realize at the time we were poor. every summer my parents would send me and my brother to live with an Aunt and Uncle who had a small farm, we helped to milk the cows, feed the animals , gather the eggs, work in the garden, etc. One Sunday we were to go to church and I really had no suitable shoes so my aunt put me in my cousins shoes, she was a Brownie and the shoes probably were not that feminine but to me they were girl shoes. Anyway I wore them, they fit, and it was only for Sunday's. A week or two later I had no underwear clean to wear so she put me in a pair of my cousins step-ins, as they called them, they even said Tuesday on them. My protestations were overridden, as I was not what you would call a rebel...yet. Anyway, I liked the feel of the cotton panties and they were in much better shape than any of my own. When I returned home there they were in my bag, I quickly tucked them away, out of the eyes of my parents and would take them out to wear when the opportunity presented itself. So that was the first time I suppose. Funny I have been looking for a set of those day-of-the-week panties now for some time...someday.

[Sami]

For me since 8 or 9 years old and have done ever since

[Jasmyne]

First time was around 8 or 9, during a summer break from school while being left home alone. Tried on some of my mom's panties and a nightee, the feel is what hooked up. I even tried some of her lipstick as well and spent as much of the day as I could like that. Sadly, I've not discovered how much a part of me it is until just recently

[Xandra]

I remember "borrowing" my mum's lipstick when she was out and seeing how my lips looked. So much better!


First time was around 8 or 9, during a summer break from school while being left home alone. Tried on some of my mom's panties and a nightee, the feel is what hooked up. I even tried some of her lipstick as well and spent as much of the day as I could like that. Sadly, I've not discovered how much a part of me it is until just recently

[edith]

Getting into my mom's makeup at around 6 years old, and stuffing balls of yarn down my shirt.

[immike]

I was 6 years old. I was enchanted by pantyhose. I found a chance to wear my mother's hose along with a skirt and blouse. Of course they did not fit, but I was thrilled and began pursuing crossdressing as often as possible. Over forty years later, I'm fully dressed as I type this. The thrill has never escaped me. My thrill was going
into Mothers closet&finding her French Maid costume from halloween&simply went into her drawer&borrowed new pair of black
pantyhose&put them on&slid into her costume&stepped into a pair of her black heels

[Christina89]

I started cross dressing at the age of 12 when I came home from school one day started watching tv and while I was watching tv I got the sudden urge to try on women's clothing. so I went to my moms and tried on one of her old bikini bottoms and I loved the feel of them on my body.

[Dani0948]

When i was about 9, i frequently played dolls and dressup with my 2 younger sisters. What i remember most vividly was trying on a pair of high heeled pumps given to us by our next door neighbor. I was really sad when i outgrew them.

[Selma]

I always had a fascination for stocking so I had two choices: Put one over my head and rob a bank or wear them on my legs and become a cross dresser.

[Courtney . J]

I always had a fascination for stocking so I had two choices: Put one over my head and rob a bank or wear them on my legs and become a cross dresser.

:laughing:

i love this site ,. some very funny girls in here . :D

[Emmalee]

Pre school in culver city I would wear dresses at the dress up station and I would play with dolls, I told Miss Audry I wanted to be a Ballerina I guess I was always a bit of a princess

[Joy3]

I was about 5 or 6 I believe and a neighbor girl [Cathie] asked me if I would be her "girlfriend". She was my only playmate at the time so I said yes. She proceeded to dress me in her clothes. She also loved playing with her mothers make-up and putting it on me. I loved it! I then started using my mothers things when I was alone and I was on my way.

[tiffanyjo89]

I must have been about 8/9.

I ran out clean underwear, and my mom was NOT going to have me wearing dirty underwear, so she told me to wear a pair of my sister's. :eek: I said, effectively, HECK NO! I didn't want to wear girls clothes. What self respecting boy does? But after I got used to wearing them, OMG, I really liked them. It was a basic cotton pair of girls briefs, but they were so much softer and didn't bunch up like my underwear.

I kinda knew that my sister had different styles as well, and as time went along, I really grew to like the different styles she had.

[deborahtg42]

when I was born I got placed in a dress and never stopped crossdressing since then, lol

[aly01]

Was about 10 or 11 tried on slip and panties of sisters.

[devida]

When I was 7 or 8 I used to dress up in my Grandma's clothes when she was out of the house. The I'd march up and down in front of the mirror. Don't all boys do that?

[Pinky188]

As soon as I realized what a dress was.... I was young.

[laura.lapinski]

I remember I had erotic thoughts at age 5 or 6 ? about wearing women's underwear. I don't remember actually putting anything on until about age 12 when I put on my cousins one-piece, body-hugging bathing suit in the privacy of the bathroom in their house. It felt so great.

[ReineD]

I remember I had erotic thoughts at age 5 or 6 ? about wearing women's underwear. I don't remember actually putting anything on until about age 12 when I put on my cousins one-piece, body-hugging bathing suit in the privacy of the bathroom in their house. It felt so great.

Thanks for mentioning this. A lot of people think that starting to CD at a young age means that it is not sexual for them, when in fact, children do begin to experience sexuality while very young.

http://nctsn.org/nctsn_assets/pdfs/caring/sexualdevelopmentandbehavior.pdf

[tanya2013]

the first time i cross-dressed i was about 10 trying on my sisters underwear while everyone was out and it was only until about 6 months ago i started wearing dresses and other womens clothing. it feels great and even better as my wife enjoys me doing it.

[alicia45]

I was about 4 and trying on my mom's clothes and pantyhose. I did it openly but then my step-dad wigged out a bit when he came into our scene. My mom didn't like it but let me do it. I was a kid after all and playing at being Peter Pan with nylons as tights. Later from about 11 to 14 years old, I'd hide it but would go out when my mom was at work in the city and would take me with her. I'd stash some clothes in a backpack. Back then my hair was a bit on the longish side and I could muster a decent pass but without makeup or very little since I had to remove it in order to check in. I'd walk to shops and try on clothes and shoes. Did anyone notice? I'm not sure, but I felt I was believable. Once I did get busted buying pantyhose when the clerk asked in a snarky tone if they were for me. Another time was when I was trying on Mary Jane china flats that were popular back then. The clerk told me to scram because I was a boy. I had it out with her, but I don't think she was convinced. Others didn't seem to mind.

[Marissa V]

My first memories are from when i was 4-ish. Dressed in clothes from my grandma (very tiny and slim woman), with a self made 'microhpone' singing along with Waterloo from Abba. I never really wondered about it until i was 7. First soccer match and we had to hit the showers after that...but that was a big no no for me. No way i was going to shower with the boys...

[scarletgender]

Mine was when I was five. I only really remembered this a few years ago. At primary school, once you had finished your work you were allowed to play with the toys and so on. There was a Wendy house in the corner of the classroom with a dressing up box. I remember a turquoise dancing leotard that had a frilled skirt to it. I would sometimes put this on (and so would some other boys, if I remember). It was definitely my first sexual experience and i remember feeling all tingly.
:)

[StephanieCD21]

It was mom's shoes when I was about 5. Over the years the occasional piece from mom, aunts, girlfriends, etc. Oddly, it would be over 20 years before I figured out what was really going on. So may years of not dressing wasted. <sniff>

...OK, I am glad I missed 80's fashions.

[Andi.Devine]

I don't remember exactly when my first time was, I was probably about 10, but I do remember exactly what I put on. It was a matching satin and lace pink camisole and short set. It was my Moms. I believe that I can still remember how I felt when I put it on, quite erotic.

[miss_jessie]

I must have been around 7 years old. I remember sneaking into my sisters room and trying on underwear. From there it was 'borrowing' skirts, tights and underwear when everyone was out.

[billy419]

when I was about 17 I would wear panties sometime, in the last year I have been dressing up some

[catdogs]

when i was 12 i seen this lepord bra and matching panties on this porno and i got trund on so the next day i whent in my moms room and got into her bras and panties and the rest is history

[PattiMichaels]

I was 4 years old at my grandmothers house. Mom was working nights in retail and Dad was out. I insisted on being allowed to wear a pair of her pantyhose, which is ironic since I now prefer bare legs nearly all the time.

First time out dressed was 17 years old, but that's another story...!

[chelyann]

i was about 10 when i put on my moms bra and nylons and the pink fog set in and has not gone away. i would not change a thing

[DanielleT]

I think I was in 4th or 5th grade when I started wearing my sisters bras and panties. Sadly, it took me another 20 years to admit to myself that I really was (am) a woman. Thankfully, both of my sisters have accepted me as such.

[katia]

Aged about 10 ,tried on my mums tights and loved it then teenage years use to try on my sister clothes when they were out :)

[Margaret]

Aged about 4. i remember trying on a friend's lacy petticoat. then at around 6 years old I remember going to the beach with some neighbours. I had no swimmers, so they gave me a girl's one-piece to wear. i loved it!

[Didi]

I was 8 or 9, and tried on my older sister's girdle and nylons.

[SophieKitty]

I was 13 when I first slipped on my sister's PVC top with a tight fitting faux leather mini skirt. By the time I was 14 I got scared and Sophie has only recently resurfaced.

[Karen kc]

5 or 6, tried moms pantys,she didnt have pantyhose, just garter stockings [early 60s] tried them on but didnt know about the garter belt! Remember wearing her pantys to school when I didnt have gym. Never looked back!!

[Joy3]

When I was 5 or 6 a neighbor girl would dress me in her clothes so I could be her girlfriend. We played all the games girls enjoyed. She would put make-up on me as we would play big girls. I really enjoyed these days as girlfriends and missed them terribly when she moved away. However, I was hooked and have been dressing for many years and loving it.

[Laurie A]

I started being interested in my mom and sisters clothes sometime around 7 or 8 years old, but I don't have a particular first time memory of trying something on.

I scanned the responses to this thread, and it seems most replies involve not only the memory of when, but exact what each person wore the first time. Most responders started between ages 4 and 14. Most responders mentioned the specific items the wore. If you look at the replies, there are several common categories in order of popularity: 1. underwear/bras/panties/slips/girdles 2. pantyhose/tights/stockings 3. skirts/dresses 4. shoes/boots 5. makeup/jewelry/nailpolish

[CONSUELO]

It is interesting that all of the replies are so specific about how and when cross dressing began. I remember the feel and look of the corset that I wore. The sunlight coming into the bedroom and the strange inner thrill that suffused my body when I looked down at the silvery panel at the front of the corset.

Also interesting is that the urge to cross dress diminished during teen years only to appear in the twenties or a little later. I have noticed this pattern in a number of replies.

[Xandra]

For a long time dressing was an erotic experience for me, too. It still can be, albeit less so.
I remember I had erotic thoughts at age 5 or 6 ? about wearing women's underwear. I don't remember actually putting anything on until about age 12 when I put on my cousins one-piece, body-hugging bathing suit in the privacy of the bathroom in their house. It felt so great.

[AlexisRaeMoon]

When I was 5, I put some balled up socks in my shirt to see what it felt like to have breasts, but I don't really think that counts as wearing girls' clothes. But when I was about 13, I pulled on a pair of old pajama pants that I stretched into a tube dress, and supplemented with mom's pantyhose and red heels.

[michelle-]

I was around ten. I was going to have a shower and my sister had left some clothes in the bathroom. I tried on a bra and filled it up with my socks. I think I tried a top as well and red lipstick. All this while the water was rumning. I kissed a sheet of toilet paper and had my shower. I kept that paper with my red kiss on it for some time.

[Tiki]

I had tried my mom's lingerie when i was something 13 or 14.
Feeling was great. Unfortunately couldn't continue it and regret now.

[Lexi Moralas]

I was 11

[Roli F]

I was 14 house sitting pets for friends his older sisters clothes were left on the maiden, dry I was captivated, crapped myself thinking they would notice the clothes had been worn when they got back, they didn't. hooked ever since never looked back.

[clarisse-tv]

first experience was about 12 with moms pantyhose.
first full dressing was 6 years ago
last full dressing was 4days ago

[Valarie]

I remember (because of my therapist) I had one of my mom's night gowns as a security blanket, I loved the silk feeling. But when I was 4 it was taken away from me. Around 8-9 my harder childhood years I found it so much fun, I would be left alone for hours, and would walk in pantyhose and heels. I loved it. But then I was caught, and had to repress it.

[Sissy_Michelle]

There were some girls down the street when I was like eight or nine. Since they were about my age I was invited over a lot and vice versa. During one of their parties I got wet and was given a change of clothes by their mom, the sisters and their friend made fun of me and said if I didn't put on the clothes that they laid out for me they were going to send me home. I didn't have a lot neighbors or friends for that matter so I was dressed up in dresses and and anything they gave me to wear. After the first time it became a habit to dress up with them, it lasted well into high school.

[Rick5881]

I was probably about twelve years old the first time I remember wearing my mothers panties, bra, girdle and makeup. I remember because my mother came home early and nearly caught me. I ran to the bathroom trying to wipe my face and remove her undies at the same time. If my mother saw me, I'm really not sure, she never said anything. I've been a cd ever since, but always when I'm alone, but now I'm trying to get the courage to be me, when I can.

[Cindia]

I honestly can't remember the very first time. First extended time (more than just put it on , take it off real quick) was in third grade, so I would have been 8, almost 9 Stayed home from school sick for two days, but not too sick to spend most of them wearing my sisters clothes. Wore everything, panties, bra, blouse, skirts dresses, shoes. Got pantyhose from, mom, sisters had a few pair of tights but I liked the pantyhose better. I remember wanting to wear a one piece shorts/jumper type thing that my sister wore when I was 3 or 4. Can't say I ever got to.

[JenniferYager]

In eighth grade I wore some of my mom's clothes. I actually dressed up as a cheerleader for our spirit day in high school as a sophomore, that was my first time out in public. Funny enough, nobody cared except the assistant principal, who said my boobs were too big (I had overstuffed them a bit)!

[DanyGirlie]

I first crossdressed when I basically started walking!!! I can't remember a time when I wasn't a xdresser... that's why I feel like I'm a girl although that doesn't effect my masculinity.

[Martha G]

Basically in my late 50's

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

I wore a beautiful period dress supported by a 120"lace trimmed hooped petticoat. I had a gray wig with curls, a fancy bonnet, hanging earrings, string purse, a black lace fan and a large bust. I also wore a pair of yellow satin bloomers with a lot of lace. The makeup was basically foundation, lipstick and eyebrow pencil.

Since then I have developed a few more female characters such as a duchess and a Southern belle. Also I dress as Martha Stewart.

Off and on throughout my life I wanted to at one time to dress s a lady but it never was a compulsion.

My avatar and profile photo are me as Martha Stewart.

[Valerie1973]

I remember I was 5 or 6. I liked this rust colored dress my mom had. I liked dresses and skirts there after. By age 10 I started trying on everything I could get my hands on. Mom was very fashion savvy and loved to shop and had a closet full of dresses, skirts, blouses, high heels, drawers full of pantyhose, slips, bras. This was 1983, Boy George and glam rock on MTV had a huge influence on young Valerie. I started experimenting with make up too. This is when I also learned to walk in heels. At age 12-13 mom's clothes were fitting me just perfect but her little size 7 feet and me at a size 9 men's, I no longer could were mom's high heels. :(. I am an only child, I was left alone a lot. This was my routine during summer vacation. My parents would leave to work around 7:30ish and I'd bounce out of bed and doll up with make-up, do the underwear, pantyhose, slip, bra padded with whatever, then find a dress or skirt and blouse outfit, and then heels. Back then it was OK to leave a kid at home at age 10 or 11. I think that's about when I started staying home alone. I'd spend the entire morning like this, changing out fits, reapplying lipstick, walking back and forth in the house. I was a healthy normal young crossdresser. By 11 11:30 I'd put everything back as perfect as I could and wash up. My mom would come home for lunch. The rest of the day I was a normal boy playing Atari 2600 and hung out in the yard or street with the neighborhood kids. Still dressing up after 35 years.

[mexdresser]

I started at the young age of 6. I used to love watching my mom get all made up and think what what it must feel like to wear makeup. Later in life, I remember how excited I would get when I found out I would have the house to myself, even if only for a few hours. Back then I was able to fit in my mom's clothes, even her shoes. I suspect she had suspicions but never said anything.

[Allison Quinn]

I can't even remember the first time anymore.. it's been a thing in my life ever since I as born. I just genuinely liked the way I looked 100 times more.

[Breanneb]

I think I was 5 when i first put on a pait of moms stockings and fell completely in love with them, boy if she could see me now

[Stacycdinma]

I'm probably like everyone else. Put on mind bra at a very young age and pretended to be a dancer. Later on I tried her panties and couldn't believe how good they felt. Have been wearing lingerie and dressing on and off ever since

[Ceri Anne]

I was just talking about this the other night at the Transgender Institute in Kansas City. My first time was one summer when I was about 10. The girls in the neighborhood, had been putting on nail polish at the picnic table and left it out. I was drawn to try it. Painted my nails a deep cherry red, then realized I didn't have a clue how to take it off.......oh well, it wore of soon enough. My next time I was around 13 and my mom had a stretchy satin body shirt and brown velvet kulaks. I had so much fun, I had to do laundry when finished............ I have always have a strong fem side, but never fully accepted it until recently. I've always gotten along better with girls, and in fact, never had a real close male friend until the last few years.

[Ceri Anne]

There were some girls down the street when I was like eight or nine. Since they were about my age I was invited over a lot and vice versa. During one of their parties I got wet and was given a change of clothes by their mom, the sisters and their friend made fun of me and said if I didn't put on the clothes that they laid out for me they were going to send me home. I didn't have a lot neighbors or friends for that matter so I was dressed up in dresses and and anything they gave me to wear. After the first time it became a habit to dress up with them, it lasted well into high school.

You are such a lucky girl Michelle, that would have been so incredibly fun

[irishsissy]

I was about 10 yrs old.

[Bethany38]

I think I was seven-ish. I tried on some clothes of my cusin.

[sperow2003]

My first real crossdressing came about when my wife to be suggested I try on her panties (way before marriage and children). She must have seen my reaction because it soon escalated to me occasionally wearing a favourite dress of hers which was floral and extremely silky. Over the years this "pastime" has given us both so much pleasure, me especially I must add.

[melissagrrl]

At about 6 years old.

[SamGreen]

I was 6, my aunt had a box of see through baby dolls, or something like that, and I just needed to put them on when no one else was watching. I've been hooked ever since.

[themodsca]

sisters heels,....
started from the feet to the head i spose

[mykell]

same for myself except they were my aunts heels, mom and dad were divorced when i was two, did it whenever i could, would love to sleep in my sisters pantyhose, cant believe all the story's hear, i feel so at home.

[jennygirl65]

I was maybe 7, had been at my cousins playing and got dirty and my aunt gave me my female cousins clothes to wear til mine were washed cause we were the same size. Been hooked ever since

[Macy4KH]

13 years old

[MichelleinEugene]

I was probably 8 or 9 when I dressed the first time. I was fascinated by one piece swimsuits. My mother had several and I stole one and hid it away for myself. It was black with little lime green stripes. /sigh

[TessaGirl]

It started late and developed slowly over years/decades for me. Think it began with girls' jeans when I first started buying them myself, about 16-18.

[ellieparsons]

I was 7 or 8 with my mothers pantyhose and never looked back.

[Nancy Salandro]

8 or 9...maybe 10...trying on my mothers shoes and tights and my aunt's lingerie and clothes. also, my aunt was a equestrienne who had jodphurs and riding boots and tight vest-like jackets. they were incredibly hot. to this day I appreciate tights, jodphur-like pants (with silk panties beneath) and a great looking pair of boots.

[KayleeTaylor]

I was around 6 or 7. My mom worked at a non-profit agency and would always bring home bags of clothes that she would sort through. When she wasn't looking, I acquired lots of girls pants and shorts from helping her sort though the clothes. Oh, they are sooo comfy! I love the fit and feel of them! To this day, I still wear women's jeans while in drab because of how comfortable they are.

[Karmen]

As much as I can remember, I first put my feet in my mom's shoes at 5, maybe a year or 2 later, but I knowingly crossdressed for the first time at age of 12, when I put mom's pantyhose on and walking around the house dressed like that when home alone after school. Soon after that my "crossdressing career" started and I wore her clothes as much I could, when no one was at home.

[LoJo]

I was about 8, started wearing my Mother's panties.
Off and on ever since, you know, acquire panties and bras, the purge.
Now back at it with a vengeance.

[KaceyR]

Well, I'm kind of new to CDing. And to the board. I'd put this in my intro but:
I'm unsure when my first literal crossdress was.
First CD technically probably happened after winning a camisole at a lingerie party I DJ'd back in '86,'87. (didn't have or get girlfriends so one day thought "let me try this on... " :) ) This was probably within a year or 2 of winning it. Still have it too, although it really doesn't fit anymore. Amazing how clothes shrink even while in the dresser... :)

[Confucius]

I've been cross-dressing all my life. I can't remember a time when I didn't enjoy it. Even as a 3-4 year old, I remember going into my mom's closet to "play mommy". I think I believed that my mother would love me more if I was born a girl.

[Tracee-Anderson]

Probably about 12 or 13. Mom's pantyhose. I was so enthralled by them I stole them outright. :devil:
Many years later I tried on my first dress. That was simply amazing. :):)

[JenniferR771]

In sixth grade, about age 12. It was Halloween and a boy in our class wore a beautiful dress, heels, and wig to school. His mother was a beautician. Everyone thought he was a substitute teacher. I was totally fascinated. I wished I had the nerve to do the same. But I kept my escapades with my mother's clothes and cousins bathing suit totally secret. Except when I was caught--and my parents wanted to send me to a psychologist. I told them it was only a one time thing. Ha!

[kelly10]

I was perhaps 4 or 5 when I would hide under my mother and father's bed when dad was at work and mom was housecleaning or preparing dinner (amazing how at that age I was thoroughly aware that it was wrong or shameful) and put on my mother's nylon stockings simply loving how they felt.

[Carla4Guage]

I've told this before, but here goes. I started at age 59 - 60. Yeah, REAL late. Never tried anything of my Mothers, had no sisters or close female relatives. I think I'm getting better at it!
Hugs,

[Ellie Bunter]

When I was about 8 I would wear my Mums tights (pantyhose). Even then I loved the feeling when my legs rubbed against each other.

[Violet-13]

about a month ago

[Martha G]

I've told this before, but here goes. I started at age 59 - 60. Yeah, REAL late. Never tried anything of my Mothers, had no sisters or close female relatives. I think I'm getting better at it!
Hugs,

Same here. Late fifties.

Went to a costume party as Charley's Aunt in a large hoopskirt, laced hooped petticoat wig, bonnet, lace fan , string purse and satin pantellettes with a lot of lace and makeup.

It was a lot of fun, so I have been developing some female costume characters along with my male ones.

Basically I do this at costume events or Halloween.

Sometimes I like to do just a lady and not necessarily a costume characters. Try to keep everyone guessing! Lol!

So want to perfect my walk, voice and mannerisms.

[Shanine]

Lets see, i tried on things when i was a teen. Mostly moms things. Really only got serious about this "hobby" like 3 years ago, so really i probably started "dressing" 3 years ago.

[tiffanynjcd24]

Since i was 13. I painted my toe nails and wore women clothing until i got caught and a beating

[Trishpdxcd2]

I was a late bloomer...a gf dressed me up a bit in college but started in earnest about 6 years ago.

[PurryCross]

hey my frends... I was start wearig girls clothes obaout 3 years ago,when i was 26.... first i use thung,nylons..and stuff from my girlfrend, i was use her clothes 6 month,than i started buying my own....

[trista.flowers]

i'm soooo depressed that i missed the beginning of this thread, and i wanted to post so badly that i only got through the first 20 or so posts before skipping here to the end to post my own:

i suppose it depends on what you mean by 'crossdress'. like a lot of us here (and probably a lot of boys who'd never have an interest in coming here), i recall a female relative ---- my paternal grandmother --- tying a scarf around my head when i was maybe 6 and telling me what a pretty girl i was. i think one time she even put lipstick on me. but i recall that instead of finding it thrilling, i found it annoying.

some time around age 10, i started to develop a fascination with two things: the first was women's boots. i frequently spent days at my aunt and uncle's house while my mom worked, and in the garage i discovered a box of pairs of go-go boots of many different colors. my older (gg) cousin was part of a dance troupe at the high school and she'd purchased the boots for various routines. after trying my best to resist, one day i rolled up a pantleg, slipped my foot into the right boot of a red vinyl pair, and pulled up the zip. as i felt a rush of excitement and an erection that surprised me, i turned to see a neighbor boy staring at me through the garage window. he took to calling me 'rachel' in private but never outed me, and i now realize he was fascinated, actually.

the other fascination was women's clothes made of certain materials that at the time i thought of as 'shiny' --- leather, leather-like, and pvc/patent materials, and when i'd see them (usually in pop culture, not my conservative midwestern surroundings), that meant miniskirts and boots, naturally. the fascination wasn't yet about wearing them, but i couldn't stop looking at them. i remember tearing a small ad out of a magazine ---- i think it may have been popular science!!! ---- with a photo of a man in casual clothes standing as a woman in a faux-leather top, miniskirt, and boots had her arms thrown around his neck and gazed at him adoringly. i hid that ad in a book of mine and actually found it twenty or more years later....

it was around this time that i started obsessing over a fantasy, working it out in more and more detail. i was the only child of a clothes-obsessed mother who frequently took me shopping with her. i began to fantasize about stumbling into a secret back room in the women's section of a department store where i'd be asked to choose items from all departments to be brought to me as i transformed myself into a woman, by all appearances, and then walked out to ... escape. as an adult woman.

it wasn't long before i started trying to make myself appear feminine, but it was only kind of dressing. most of the clothes i wore were my own, but i'd add a pair of boots my mother had abandoned in the basement, tried to use some rags and a shiny piece of fabric to create a bandeau top and small breasts, and tie a scarf over my head to hide my boy hair. this started out terribly exciting but quickly became ..... frustrating.

i was 12 or 13 when i finally 'went all the way'. like others here, this happened on days when my mother had to work but i had no school. i quickly found the only sexy pair of panties she had and used carefully rolled undershirts to fill out the bra. the very first time i raided the drawer in her dresser that held her pantyhose, i discovered this odd pair of items all the way at the back, sheer and black but only long enough to cover a leg each, and my fascination with stockings began. (it also explained the strange clip-like things on each leg of the girdle i wore --- it wasn't until i went to university that i realized that garter belts weren't only worn by naughty sexy english girls in music videos and monty python sketches). i chose a suede pencil skirt and a bronze-colored satin blouse, tied a satin scarf around my neck (even though my adams apple wasn't yet big enough to need hiding), and a pair of strappy black patent sandals with 3-inch heels. that's pretty much what i wore every time ui dressed for the next two years, nearly. i got pretty good at makeup, but hair was always a problem --- i tried slicking mine back (with vaseline --- ugh!!) but usually simply tied a scarf over it.

not long before my 15th birthday, on a weekend evening when i expected my parents to come home very late, i was mostly dressed and about to do makeup when i heard the garage door open. i managed to get everything off, but couldn't hide the evidence. my parents badgered me into confessing, which started a year of weekly visits to a therapist to 'break this habit'. the irony is that the first time i was alone with the therapist, after we talked for a while about my 'problem', he told me i'd probably want to do this for the rest of my life and that it was perfectly okay, but since my parents weren't okay with it ---- the clear implication was that they were overreacting ---- i should probably wait until i'd moved out of their house before trying again. which is precisely what i did four or five years later!

[Michelle504]

I was 13 and had a day off of school. I was really bored and wanted to see what I would look like as a girl. So i put on my mother's makeup and discovered that it was exhilarating. Of course I had to try on the clothes after that. I loved it! It was right then and there that I knew I was different than the other boys I'd known. For a while I thought I might be gay and it bothered me. But that wasn't the case. I would dress-up every 6 months or so, not very often - didn't have the privacy. Now I'm much older and I'm out to my wife. I have my own closet space with girl-clothes and heels and all. Being en-femme now & then is a part of who I am and I'm glad to have something that I can enjoy. We hafta make life liveable! Not as cute as I was when I was 13 tho! Nature - whatcha gonna do...

[Adrienna]

Goodness....I was about 5 or 6 when this fetish thing hit me which started with boots, my own, "Wellies". Rubber, pvc and leather fascinated me to no end and was determined to obtain some garments of this material and don them. Well, to cut to the chase, I have CD'd off and on all my life always in secret. Played many fantasy roles with a few partners(female), and now rarely dress. I guess with age weariness sets in but the desire is always in the back row. But I enjoyed it immensely and when I do Cd I still do.

[dana digs sweaters]

4, was wearing a slip and I do not remember this but have a pic of me in it. Was 5 when I took a cardigan from one of my sisters and remember that.

[andrea35]

The earliest I can remember was maybe five. My parents had a big fight my mother was crying and I was frightened I ran to the bathroom where my mother had left a blouse that I liked because of the patterns and colors. I put it on of course it was too big but the feel of it was something new for me and I did it every chance I got ever since.

[AmandaJosefine]

First time for me was when I tried my 3 year olders sister's one piece swimsuit when I was 6. I liked it back then so my mom asked me if I wanted her old cloth. I said no cus I was affraid, regrets regrets

[Paula Siemen]

I was probably 11 or twelve. I had a sister two years older than I and watched as she developed from a girl to a woman. I was so intrigued with all the girl stuff she had. Panties, bras, pretty dresses and the makeup. When everyone else would leave the house, I'd go into her room and try on her panties and bras. I was heavy, so I really couldn't get into her dresses. I loved the feeling of her clothes. Just everything in her wardrobe was so intriguing to me.
It set me on my path to the CDer I am today.

[Joy3]

At age 5 a neighbor girl would dress me in her cloths so I could be her girlfriend. I loved it and started wearing some of my moms things. I was hooked and love it to this day!!

[Lacyfem]

I was ten when I slipped into my mom's panty and bra and was immediately hooked!

[Connief]

I was about 5. During the summer, mom would leave me with a babysitter while she went to work. The babysitter's daughter and I use to play dressup then play with her dolls. I loved dressing in her pretty dresses. Sometimes the babysitter would let us wear her necklaces and earrings. After that I was in mom's closet every chance I could get. Loved wearing her peignoir sets and dresses and yes all the under trimmings.

[teri222]

Carla, 59 or 60? Unbelievable! You are so feminine and "dress" so well. Hey girl, I just took a look
at your pictures on flickr. Very well done. Thank you for sharing them with us.

[missjoann49]

Four and five years old, my mother had me put on dresses she made then have me get on a chair so she could make the hem straight. Sometimes wore those dresses all day long. My father was away in the hosptial then and never knew my mother dressed me in dresses.

Phoebe, you and I had kimd of the same experience, I was around 3 or 4 years old, an only child and my mom had always wanted a girl...my dad worked alot of nights, so when ever she had the chance she would dress me as a girl, this went on until about my first year of high school then she stopped....It was only a few yrs later while I was on my own that I started doing this again as I had missed it so much....hence after a couple of bad marriages I am well on my way to who I am and who I will be till the end of my life
Hugs
Joann

[CONSUELO]

I found this particular thread very interesting. The commonality of experience is astounding, though the details vary a lot. I was impressed that so many respondents mentioned that the first dressing experience was so clear and so powerful and erotically arousing. So, I did a count to see which ages were the most common. I divided the replies into bands;<5, 5-10; 10-20; 20-30; and lastly 30+. I could not get a clear age for a few responses and there were several multiple responses that I caught, but I may have missed a few. So, there are some errors of course but not too bad.

Anyway, 28% of those responding reported a memory of cross dressing at or before the age of 5. The largest group sat between 5 and 10 years--- 45%. There were 24% between the ages of 10 and 20. After that it tails off quickly with about 2% reporting a first experience in their 20's and a similar number for the 30+ group.

i didn't break it down any finer but of the 5 to 10 group there were many who stated 6 or 7, so the data may actually be skewed toward the early part of that range. I had to go through 16 pages to get this result so I don't feel motivated to go back and regroup the data. Perhaps someone else has done so already.

So, just as we all thought, the age at which we first experienced that cross dressing thrill, mostly with lingerie by the way, was younger than 10 years old. However, a significant number did not start until they were in their teens.

Any thoughts or comments from anyone?

[krissy]

I traded clothes with my sister in a movie house at the age of ten but i use panties at 7

[JessMe]

I've got a sister that is four years younger than me... not sure of my exact age at the time, but she wasn't born yet when I started making "dresses" from my bedsheets.

[Katy120]

I wonder whether you can draw a direct line from the experience of dressing in your mum's intimates as a youngster and crossdressing as an adult. Is wearing your sister's panties a seminal event? I'm sure I don't know. However, I wouldn't be surprised to learn that many young boys try on bras and panties as a child and never crossdress later in life.

[kristy321ca]

My mom's panties were accidentally in a pile of my own laundry when I was about 10. I have no idea why, but I put them on, looked at them on me, and got a huge rush of excitement (metaphorically and unfortunately, literally). The rest is history.

[CONSUELO]

I wonder whether you can draw a direct line from the experience of dressing in your mum's intimates as a youngster and crossdressing as an adult. Is wearing your sister's panties a seminal event? I'm sure I don't know. However, I wouldn't be surprised to learn that many young boys try on bras and panties as a child and never crossdress later in life.

Perhaps they do not go on to become a cross dresser but for me and the several hundred others on this site and hundreds of thousands of cross dressers around the World, it must have been a life changer.

[dawnmarrie1961]

"It all began such a very long time ago...." Actually I haven't the faintest idea. I'm still working on that one. Ask me again later. OK? I might have an answer then.

[Wezzcott]

My first time was when I was around 4 or 5 years old. I used to find my mothers pantyhose and put them on and really liked the way they felt. Then, at around 12 or 13 years old, I really got into nylon panties and loved wearing them and pleasuring myself with them. As my teen years went on, it kept getting more intense. When I was around 17, I started buying my own clothes, usually from thift stores and such. By the time I was 20 I had a full wardrobe and became who I am now.

[Susan.]

I barely remember my two little sisters and I dressing up while playing in a pile of dirty clothes. I was probably 6 or 7.

[Kelly Anne]

I don't remember how old I was however I remember wearing my mother's thongs and bras and even though I was very careful (I thought) at putting them all back where I got them they disappeared out of her drawer after about a year of me doing this. So when I turned 16 I started wearing men's thongs and told my mom that I wanted to wear thongs which she supported and even went shopping with me to buy them. I told her there wasn't much selection so we could always go look in the women's department to find some since they're basically the same thing... She said there was no way she was buying womens underwear for her son. She never said I couldn't but she wouldn't buy them. So after I left for college I started buying... not I have a lot of lingerie to make me happy :)

[CarlaWestin]

I was an astronaut. While listening to the final 10 seconds of the countdown, I used my smartphone to order a leather corset and six inch heels from ebay.

Not really. At age ten or so my mother's bras called to me from her lingerie drawer.

[Stacy_sometimes]

I was probably 4 or 5 years old... I used to like to play in the freshly dried laundry because it was nice and warm out of the dryer. One day I found a pair of my mom's trouser socks in there and loved how smooth and comfy they were so I would sneak them on and wear them around the house. One day I was caught and got pretty embarrassed so I stopped for a while.

I started again in my early teens, but was much more careful about being caught. I got progressively more and more into it through high school and college and started buying my own things...much more fashionable than my mother's clothes! :battingeyelashes:

[Katey888]

This is a really interesting thread and question (and answers!) - really made me think too. I would have been about 6 or 7, and girls' fashion at the time (this was late 1960s) was for fluffy, acrylic hats that tied under your chin. At school, I would ask to use the toilet (restroom...), go into the cloakroom that was outside the classroom and try on the girls hats. It's weird now thinking/writing about this, but there was obviously something sensual happening about both the feel of the clothing and the fact that it was 'disguising' or transforming me. I've only thought about this now, but that desire was overtaken very rapidly by coming in contact (literally) with my mother's nylons which were obviously lying around the house. I can remember the thrill of trying on different styles and colour stockings in my bedroom and loving the sensation - it's still there today. That progressed to illicitly obtaining my first pair of fine grey tights/hose a few years later and wearing them with a wraparound skirt - the combination was quite explosive... Wow...

[karens70]

I dont remember exactly, I think it was around 9 or 10, I just remember that the sensation of pantyhose did something to me that I could not explain but I really liked. I do then remember moving into trying other clothes that belonged to my sister/mother and found that adding a dress/shoes etc enhanced those feelings.

[Marla]

Loved wearing my Moms lipstick.

[laciewhite]

it was very early for me, not sure exactly what age but pre-school, trying on my mum's shoes and stuff like that. i always felt it was a naughty thing to do and always did it in a very secretive way.

and when i started school i remember wishing i could wear knee-high white socks like all the girls did.

i got interested in nylons and lingerie pretty much from puberty onwards. started trying on my mum's things. and my dad's girlfriend's stuff (my parents were divorced by then).

got into make-up and buying my own clothing in my twenties.

[Shar]

I started at the age of 17 and by 18 I was full time,going to college as a coed. Never looked back.

[Billiejosehine]

I don't know exactly when, but I do remember wearing my moms stuff sometime at a young age. I think it was at the of 15 when I really began CD and I have been doing it ever since.

[asiants]

I started when I was 8 or so, and trying out mom's clothes and lingerie and along my teen days.

[MsPriscilla]

aged about 13. got this urge to try on Mum's clothes while she was out and got that sexual buzz, loved it and still do

[Courtney Ramona]

I believe I was 5 when I found my mom's clothes from when she was a kid in a suit case. I didn't give it much though but I kept on dressing never felt bad never felt wrong

[Algoma]

I remember being 5 or 6 putting and on my mothers jewerly, clip on earings and lip stick. By jr high I had taken her fishnets, loved them. By college was into my girl friend clothes. Put dressing aside for 20 years and didn't buy my first pair of pumps until much later, 40's then the dam broke, with clothing, corests, wigs and makeup. The rest is history, Algoma

[valerieg]

My earliest memory is from when I was about 4 years old. My mother had a short black gaucho that I could wear like long pants. I'd put them on an run around in the laundromat on Saturday morning laundry runs.

[Arianny]

When I was about 5, tried on some pantyhose and have loved it ever since.
But I only do it for the sexual thrill, once I relieve myself I put on my regular clothes.

[VickieFairfax]

Growing up with 2-older sisters that are close in age, I was always jealous of the attention and clothes that received. I'm not sure if at what age (7 or 8) I first tried on a dress, but I've been hooked since.

[Becky Adams]

Started about 8 whn I was "used" as a model for a flower girl's dress for a neighbor girl's wedding...told to my face I was too pretty to be a boy

[NikkiBeth]

I don't remember exactly but I remember trying on my mom's stockings and white fishnets in our laundry room. I was probally around 4 or 5. The rest is history.

[Stephanie Julianna]

I'm the youngest with four older sisters. I was 6 when my oldest sister was 16. That was 1955 and the girls' dress were to die for. I think I started around then because I was old enough to be left home after school until my mom came home from work in an hour or two. In that time I tried on every bouffant petticoat and dress my sister owned.

[SarahBJackson]

Over 5 years ago, I dug into my wife's drawers looking for pantyhose or tights because of a sexual fetish. However, in May 2012, Sarah emerdgeed and I started dressing then again NOT sexual fetish, but because I'm probably a transgender.

[LadyInRed]

For me it would have started at about 9-10, I realized there was something not fair, girls got all sort of fun clothes, skirts pantyhose, makeup, and that wasn’t even including underwear, I started playing with my moms makeup trying it on, at some point I would sneak into my parents bedroom and I tried on some of her clothes, then my parents caught me one day, boy did I hear about that. And that ended that while I was under their roof

So the first time I actually tried full on when I was 20 and living on my own

[NathalieX66]

This is the classic and famous question, and it appears on this forum from time to time, and every now and then.

Without getting into specific times and dates in our lives, it often begins in that very moment in our childhood lives where we ask that question "why do girls wear dresses, and boys wear pants?"

[Jamie Christopher]

As I remember, I was about 11. We had a big house, 8 kids, 3 girls and 5 boys, the girls all my elder. I went up in to the attic one day, and was going through some boxes of stuff, and found a white full slip. I remember taking off my shirt, and pulled that slip over my chest and pulled it down....the feeling was intoxicating...and the eventual result is what you might imagine; a first for that little boy...lightening! There was no turning back after that, I was changed forever! After that my mom started finding me hiding one of her bras between my mattress, oye! Still one of my favorite things: pick out a pretty white bra, insert my breast forms, and pull a nice lacy full slip over and down over my body...heaven! I always wished I could look down at my chest and see female boobs.....

[Michelle Wright]

When I was about 9, my sister had a heap of dressup material in our playroom, so I was frequently in girls clothing and jewelry, my sisters had this sort of coloured lip gloss and I started wearing that. As I got older, I started wearing girls clothing more frequently, I was still using lipgloss and lipstick up until I was about 12. One day I planned to try a full girly makeover in the bathroom, so I grabbed a few of my sister's dresses, a bag of jewelry and my mum's bag of makeup. I was very rough with my makeup skills and I looked a bit subpar. Over the years I have improved greatly and could pass for a female with a wig and a bit more skill, I still can't apply blush, lol.

[auroraonline]

I think I must have 4 or 5, sneaking into my mum's room as she slept, trying on here underwear and nylons.
I remember also nagging my Grandma for lipstick at this age.
I seem to remember having to wear green tights for a school play at a similar age. Protesting to my parents that these were for girls, but secretly loving it.

But it really started when I hit puberty, in my mums wardrobe, and faking sick days to stay home from school.

[Confucius]

I understand that about 70-75% begin in early childhood. Then about 20-25% begin in adolescence. Finally about 5% begin in adulthood.

As for me, it goes back to my very earliest memories. My mom would tell stories about how she wanted a daughter when she was pregnant with me. I was a very clingy baby, always wanting to be carried by my mom. When I was about 6 months old, my mother was pregnant again. This time she gave birth to my sister. My mother finally got the daughter she always wanted. My sister was pampered, spoiled, and I was jealous. When I was about 3 year old I started raiding my mom's closet and playing "mommy". In order to keep me out of her closet my mother made me a dress as play-clothes. My father was upset with this and the dress had to go. I had to undergo some sort of aversion therapy, but it didn't take.

[autogirl]

12 years old

[FeliciaCDSNJ]

The earliest I remember, would be around 5 years old. It began with pantyhose and scrunchies and escalated from there. Been caught plenty of times and had my butt beat for every time too but in my opinion it was well worth it and now at adulthood, it's all fair game. I remember being caught before school wearing a bathing suit under my clothes, I had got the bad end of the belt and hand before school and more of it after I got out of school. It made me much more wise were to stash my hidden gems out of the gaze of parental figures and siblings. I didn't start fully dressing, however, until the age of 19 where it felt so natural to me to be dressed up, even it was just around the house.

[Xandra]

There's dedication for you. Luckily I was never caught. :-)
The earliest I remember, would be around 5 years old. It began with pantyhose and scrunchies and escalated from there. Been caught plenty of times and had my butt beat for every time too but in my opinion it was well worth it and now at adulthood, it's all fair game. I remember being caught before school wearing a bathing suit under my clothes, I had got the bad end of the belt and hand before school and more of it after I got out of school. It made me much more wise were to stash my hidden gems out of the gaze of parental figures and siblings. I didn't start fully dressing, however, until the age of 19 where it felt so natural to me to be dressed up, even it was just around the house.

[Steph70]

I see a trend here...it's the pantyhose! The pantyhose companies made them so irresistible so they would have a more people to sell to. It sure worked on me lol. Probably about 10 like a lot of people here. I do remember putting on as many pantyhose as I could find at one time. Not sure what that was about....

[Carrols]

I was 11 or 12 when I tried on my sister’s bikini. I remember loving how good it felt. Next were her panties and a bra. I found a pair of my Mom’s stockings and a girdle with garters in the bathroom and tried them on. I wore them to bed that evening. That was 48 years ago and I still love the look and feel of a bra and stockings!

[Patty-Fay]

I was around 4 years old, this was 1958 (before there were panty hose, btw. I had two older sisters, 5 and 8 years older than me. I remember always being jealous of the pretty clothes they always got (I suspect this jealousy is at the root of my obsession with feminine attire). I specifically remember coveting the younger one's new red petticoat. I put up such a fuss she let me wear it frequently. In later years, I'd sneakily wear their panties and bras, and put on lipstick. When I got a job in my later teens, one of the first things I bought myself was a cute baby doll nightie. I never fully dressed until I moved away from my parents in my early 20's, and I had both the time and money to indulge myself.

[Bima]

I have a vague memory that I at age 5 (or perhaps 4) for some reason wanted to wear my neighbor friends mum's coats when I was standing alone looking at the coats in the entrance hallway of their apartment, but I accidentally tore down the entire coat hanger construction in a feeble attempt to reach the coats. I don't remember if I could try a coat on or not in the end, or what happened after I ruined their coat hanger.


Swapped jackets with my first "girlfriend" at age 7. She had a girly orange and red winterjacket that I adored and really wanted to wear. For some reason, she was happy to wear my jacket, and we wore each other's jackets day long, and over a couple of subsequent days.


In my first school years, my first or second grade, 7-8 years old, my teacher had this long slim and beautiful dark brown leather coat with a fur trim which I tried on when she had left it outside the class room and everyone else where away for lunch. I remember that earlier on, the girls in the class had borrowed this coat and walked around the schoolyard wearing it, and our teacher had berated them afterwards. Anyway, I remember that I was really jealous, fascinated and for some reason also wanted to wear the coat and walk around the school yard. At that age, neither I nor them, where that tall so the leather coat nearly touched the ground. And then in the end, I tried the coat on, felt like a grown up woman, and I was in heaven. :-)

[Adriana Moretti]

10 years old? ish... Cousins ballerina dance recital costume found in my grandmothers closet.....

[Berta82]

Started somewhere around 6 or 7. Trying on moms underwear because I loved the feel of silk and satin. The next age I remember when it really took off was around 10 or 11. We had just moved and I would occasionally stay at my grandparents where my parents had stored things in the attic. I remember finding a giant bag of bras, panties, girdles, and stockings. It was heaven and I haven't looked back since.

[lesli]

Alexandra,
i used to run around the house in my mom's heels when i was maybe 4? i loved it! back in the day, there used to be small sample lipsticks that would be given out, and my mom would give them to me to play with--i loved them too.
hugs,
lesli

[Rebekka]

I was about 10 years old. I love the feel of silk and satin. I tried on mom's white blouse and was instantly hooked and I never looked back and have been dressing since then. The feelings are so very INTENSE........I love it !!

[Monet's dream]

I remember being in grade school and sneaking into my older sisters room when everyone was gone and putting on her clothes, starting with undergarment, girdles, etc and then trying on so many of her dresses. Guess I was lucky that she was so much older than I was so that she had enticing clothing - even back in the 60's.

[Julia NZ]

I was about 9 or 10 and was staying at my Grandparents place. It was a big house with lots of bedrooms where my aunts and uncles still had their own rooms even though they were all away from home. I was in an aunts room staying and in the wardrobe was a satin full length bridesmaid dress from a wedding we'd all been at recently.

Tried it on..........gorgeous! And the feel of the fabric..........unbelievable!

[Ally 2112]

about 11 years of age the cding had been working on me for some time ,I was whatching an epesode of happy Days nobody was home .i went up to my moms clothet found a dress i thoght i would fit
It was a feeling i had never felt before or since .But as much as i hate it at times i love it

[Brooke B]

I was about 10. I went to a relatives place by a lake. We went walking and someone had left a pair of white flip flops there. I drug behind long enough to be out of sight and then tried them on. Flip flops don't seem like much, but it was enough to be hooked for life!

[rah]

idk when but i remember when i was forced to do it when i was very young my sister with her friends put on a white frock on me and we went to the mall and i hated than

[paigecd]

since I grew up in the 80's and women actually wore pantyhose, I wanted to try a pair on so I started with my sisters pantyhose at 7 years old and the rest is history

[Debby1194]

I was probably around 4 or 5. A female relative thought it would be fun to use me as her personal Barbie Doll. After that I was hooked

[Caden Lane]

At age 3 I used to run around in one of my moms nighties. At age 7 I found some panties at a friends house. About that same age I discovered my moms square dancing petticoats and pettipanties. From there it was all history.

[Kristy 56]

Yes I do. I was in first grade and the girl across the street who was the same age had a dress up skirt. One day she left it outside. There was no one around so I grabbed it went behind a bush and tried it on. At least that's the way I remember it.

[Donnagirl]

From as young as I can remember... Three sisters made for a plentiful supply.

[ShelbyDawn]

I can remember being five or six and sneaking into my moms dresser and stealing her slips.
I still love satin and lace...
As I got older, I started "borrowing" things, panties, bras, dresses, etc., from my sisters.
Once I moved out on my own, it became more opportunistic; i.e., I would get lucky enough to have a pair of panties mixed in with my laundry in the apartment complex or a girl friend would leave something at my place.

[Vanessa Rose]

4-5 years old. Cousins basement play for parents. I had to wear that pink satin outfit with tutu. I was finished the second I had it on.

I felt pretty and perfect!

Vanny

[Tina B.]

At around 6, sister left her slip hanging on the bathroom door, the fit was bad, but the feelings where oh so good.

[Xandra]

That is a beautiful memory. Thank you for sharing. :-)
I was about 9 or 10 and was staying at my Grandparents place. It was a big house with lots of bedrooms where my aunts and uncles still had their own rooms even though they were all away from home. I was in an aunts room staying and in the wardrobe was a satin full length bridesmaid dress from a wedding we'd all been at recently.

Tried it on..........gorgeous! And the feel of the fabric..........unbelievable!

[K8astrophe]

My first memory of dressing in any form coincides with my first memory of being caught too. Wearing my mother's knee highs at about 6 underneath my footie pajamas. Just before bed my mom came to put socks on me since it was a cold winter night and I was caught red...footed...and faced. She caught me in pantyhose once later at 13... Not the slyest kid in the world.

[CD Husband]

We were at my aunt's house. She was (is) the type that wore pantyhose and heels everyday. I had to go #2 something wicked so she let me use her master bath, which was like finding the holy grail. In there she kept a hamper just for pantyhose and I couldn't resist trying them on. I was maybe 6 or 7. I had them about half on and the door flew open and there was my mother, wanting to know what was taking so long. When she noticed what I was doing, all hell broke loose. Not pleasant.

[stephannietv]

I started at age 11,i was so amazed how good it felt wearing nylons and figured if nylons felt so fantastic,why not try panties,bra,skirt,heels etc and the more I put on,the better I felt and still feel the same,maybe better when I get a chance to dress now

[chrissietoo]

I was in 5th grade when I asked my mom if I could be a girl for Halloween. It just came out of the blue (or out of the pink). I don't recall sneaking into her drawer (at least not before then)....but I admired girls and obviously wanted to emulate them. My mom took it as a crafts project and went to the thrift store, put together a lovely costume. The next I remember was slipping on my girlfriend's bikini and feeling euphoric. :)

[ArleneRaquel]

Somewhere between 1954 & 1956. I wore some of my mothers things, other than heels I don't remember exactly what. Starting in 1959 I wore her cat's eye frames when ever I could get the chance. She was supposed to wear new first pair of glasses at all times, but for the first year or two after her first fitting she wore them about 90% of the time. I sure did like my look waring red lipstick, red nail polish and her brownish frames. I sure did give me a rush. Her next pair were silver cat's eye, which I don't believe I ever borrowed. My mother went to an ivory cat's eye frame. I believe she looked her most ravishing wearing the ivory frames. Staring circa 1970 dhe went to wire non-cat's eye style. By 1970 I had my own female frames.

[Christen]

I think I was around 6 years old. It was a little embroidered beige cardigan. Belonged to a girl who visited our house. I can't even remember her name or whether she was a relation or not. The compulsion to try it on was so strong.

[Rachel292]

I'm not sue, it was either my yonger sister's checked mini skirt or my mum's green tight skirted almost backless 1950's/1960's style dress. It must have been mid/late 1960's when i was about 10 or 12

[Barbara Jo]

I was about 8 years old back in 1955 and had a younger and, an older sister who was about 4 1/2 years older then me.
Yeah, I was the middle child with two sisters.

I began to wonder what it felt like to wear all those feminine, '50s female clothes.
So, one day, I put on one of my mom's nylon panties and full slips.

I was hooked and soon began to also try on my older sister's things as she got into her early teens and began to get very feminine grown up lingerie and other clothes. :)

[Annette_boy]

Hi everyone

I was 5 years old (in 1950) when I first tried on a pair of moms Panties they were nylon and felt real silky I was hooked from then on in 2006 I went fulltime and have not worn male clothing sence

Hugs Annette :D

[Princess_pantyboy]

I think my mom put me in girls clothes when I was small because we had some hand me downs and she said I was two years old, and put me in a dress and brought me to the mall.

[Xandra]

Thanks to everyone for the responses. I am so loving reading about your memories. Keep 'em coming..

[Kit]

The first time I completely dressed was at an anime convention. I build myself up to it for like 6 months, getting the costume and wig together and teaching myself makeup, how to walk in heels and other tricks, but that was the first time I felt complete lol. I was so damn nervous and almost didn't leave the hotel room about 5 times but I was finally convinced to, and within the first 10 minutes got some cool responses so I ended up having a blast :D have loved it ever since.

[timbertv]

I remember being in 8th or 9th grade and watching a talk show during the summer and seeing Rupaul and decided to go get some of my sisters clothes and try them on.

[lovetobedani]

I can remember back as far as when i was about 4 playing with and trying on my mothers bra and heels. A friend of hers was over and saw me and commented on how cute I was to want to look like my mom. Then I looked at lingerie ads in publications and wondering if I would grow up to look like this. Nothing was ever said to me about either. Maybe thought that I was just too young to understand. This was in the late 50's. It wasn't until I was 12 almost 13 did I dress fully. I have no idea why. It just felt like the right thing to do. From that day on I get the most wonderful clam feeling as if this is the way I was meant to be.

I've always been jealous about how many different choises women have in clothing styles and colors. Men have a basic and limited choises that's not diverse enough for me. I once told this to a GG I was dating and she told me that she would teach and help me dress if I wanted to. Like an idiot I said no hiding for the fear of being humiliated for what I've been doing for years. I look back on this as one of the greatest mistakes I've made in life.

What I find the most amazing is so many of us have the same past from the time we experiemented at an early age to looking forward to the hamper, bathing suits and lingerie hanging to dry in the bathroom when we were in our early teens.

[Peta-Downunder]

I have always had a thing for satin and silky fabrics for longer than I can remember, I guess my main source of that was woman's clothing an mainly underwear and sleepwear and progressed from there. Wasn't until my late teens I was in a position to start my own collection.
Now just shy of 40 I only just got my first wig, make up, and shoes that fit in the last month or so as I am now living alone and can have this sort of stuff around :) Been shopping online now too building up a collection.
First time I got myself funny done up it just felt terrific, one of the best things ever!

[DorothyElizabeth]

Here's a little essay I posted on another site a little while back.

Feb 2005

So, when she left, I was devastated. I felt so ALONE – so vulnerable. I’d come home from work to an empty house. I wandered from room to room, searching for - for what? For her. Not just some sign of her; they were everywhere. I saw them in the rooms where we had sat and drunk coffee together, in the kitchen where we cooked, and ate (both food and each other) together. NO, I wasn’t looking for signs; I was looking for HER.

It took a year or two, and I finally got used to living alone – well – not really – used to the feeling of emptiness. And I no longer missed her, specifically – I just missed having a woman around. Then, one day I got a call to go play Cabaret.

In Cabaret, the orchestra is a part of the show; they are all supposed to be musicians in over-the-top drag queen outfits and makeup. I was a little leery, having never cross-dressed – well, not since I was a very young child, playing dress up. But the gig paid $350.00 for two weekends performance, and two rehearsals, so I accepted.

At first, it felt strange, sharing the dressing room with strangers of both sexes, but there was a certain decorum. Of course we all looked at each other, but there was no open staring, and no gesticulation or even raised eyebrows. By the third performance, we were used to seeing each other nude, and began to be a little more relaxed about our sexuality. Clearly, it was not something that could be ignored entirely – but we laughed off the occasional erection (over either men or women) and we all became more like siblings than couples viewing each other as potential sexual partners. (Though there was a little of that going on between some members of the cast, in a reasonably discreet manner.)

But the odd thing was, one night the power went out just as the final curtain went down. Emergency lights came on, and the audience vacated the building in an orderly manner. But we who were in costume and makeup couldn’t see in the dressing rooms, to wash the makeup off, and couldn’t see to sort out our clothing and such. So we all decided it was easier to drive home in costume, and change there.

When I got home, it was like a light bulb went off in my head. Suddenly, there was a woman in the house. It felt right, somehow.

I have been “dressing” ever since.

I rarely go out dressed; I don’t care to bother with all the makeup and such that is necessary to “pass”, and there are too many people in this essentially rural county who know me from the years I spent working for the local government. But I always “under dress”; I no longer even own any male under clothing, except socks. In warmer weather, I only wear a bra if I am exercising (I need a sports bra, to keep things from bouncing and hurting – a by-product of testosterone blockers I take for my enlarged prostate) or wearing a suit jacket or blazer. But in cooler weather, such as we are having now, it is easy to hide the telltale straps and clasp under bulky sweaters or a down vest (purchased online from the “Women’s Outerwear” section of Lands End, thank you very much). No one has ever noticed that it closes the “wrong” way; or if they have, nothing was said.

[Zimri]

College! Found myself with the keys to the theater department's costume storeroom. A world of exotic clothes, shoes, corsets, you name it... no turning back ;-)

[Xandra]

Delightful :-)
College! Found myself with the keys to the theater department's costume storeroom.

[Shadowgirl89]

i must have been about 7/8 years old i remember seeing a pair of my moms panties they were white satin bikini with little red roses on them i love the way they felt and i had to try them on and it was one of the greatest experiences of my life

[FairyLink]

When I was a little kid. Not sure what age. Under 10 though.

[JazmyneCD]

I was definitely under 10 when I first tried on a pair of knee highs. I loved the feeling and eventually graduated to pantyhose. Of course, I'm still doing it as well as a handful of other girly things.

[AKADonna]

When I was about 12, my parents would go out every Wednesday night to play cards, leaving me home alone. Well, after rummaging through my Mom;s lingerie drawer one evening and trying on one of her Playtex bras, I was hooked. Wednesday evenings became "play night" where I would dress up in all sorts of girdles, bras, longline bras, strapless bras, slips, dresses and heels. I stopped it when we moved about a year later and didn't resume until I was more than 50 years old. I've since been dressing for the past 20 years!

[Annaliese2010]

My sisters panties when I was a little kid.

[lisagurl]

my aunt dressed me up as a girl, then i went home and began to wear my step mom panties :) i started at like 10 or so

[Milou]

I started when I was 13 and quitted for around 10 years. Even though I'm alright, I had my fair share of guilt and anxiety. I will probably crossdressing in March and hopefully I'm able to accept and love myself.

[deevon89]

My cousin completely dressed me when I was 7 and I mean top to bottom purple silk panties purple bra cute lil flower dress curled what little hair I had and full make up and nails .... Best feeling of my life

[FeliciaCDSNJ]

There's dedication for you. Luckily I was never caught. :-)

I was caught numerous times, from my hidden stash to me actually wearing the items of choice but that never stopped me. :-) Even now, I own no male underwear and restarting a wardrobe that was lost to me due to an ex abandoning our old apartment when we went our separate ways.

[prettygirl4]

It was probably elementary when I secretly tried on my sister's clothes. However, as young as 5 I was always envisioned myself in a wedding dress one day so I always sort of knew. Did it secretly for a few years and now it's all I wear. I've thrown out all my men's clothes (im now 22). It's so freeing to walk around in what your comfortable in

[CONSUELO]

I have really enjoyed reading this thread. My early cross dressing experiences were so intense and I look back on that time with great fondness. Reading this thread takes me back.
By the way. How does one start a thread?It might seem like a stupid question but I am really not sure how to do it.

[Corrina]

I remember when I was ten. Wearing my stepmoms silky full slip, oh the deposits I left on that!! Hooked for life :-)

[Helen Grandeis]

I was in seventh grade. My parents were out. For some reason after my siblings had gone to bed, I wandered into my parents bedroom and put on my mother's girdle with attached garter stockings. It was surreal. I did a gymnastics move supporting my self on my arms with elbows tucked into my abdomen with my body horizontal. I rubbed my stocking clad legs together. The heady erotic feeling plus the physical exertion resulted in my first orgasm. Thus imprinted, various strenuous positions plus silky stockings reliably produced the same results. For a while, I could also fit into my mothers 5-1/2 pumps in dozens of colors. This carried me through middle school and high school.

[CDAshleyAnne]

Like many who have posted before my, I've had the urge to crossdress since I was very young. I actually can remember fantasies from before I was 8 involving a complete transformation of my body. When I became a little older, I started exploring with my sister's clothing and one distinct memory was the year that I, under "extreme protest," allowed my Mom and sister to dress me in my sister's junior high cheerleader uniform for Halloween.

[Anna H]

Hmmm, not sure if mine counts....but my mom was the
oldest of 4 sisters. One was still pretty young. They
weren't a well-off family, so when i was brand new, for
my first few years, my clothes were hand-me-downs
from the sisters.

My mom told me that years later. I do vaguely recall
sitting under the ironing board in the half-assed shack
we lived in and one of the sisters teasing me about the
little dress i was wearing. Playfully, of course.

On my own was about 8. I didn't know or care about
anything to do with sex....i just liked the clothes.

I made several mini-skirts from just cut-off jeans for
years after. I could make them whenever i wanted
a new one.

~♥~

[Randee]

I became curious at age 9 when I saw the girls at school wearing leotards and tights in my sister's dance classes, especially recall when a girl appeared in my classroom wearing leotard when performing show and tell. I satisfied my curiosity the next year when I was 10. While mom and sis went to girl scouts one day a week, my carpool dropped me off to an empty house. All I could think of on the way home from school with my friends was what I was going to be wearing secretly when I got home, and hoping they could not sense how tingly it was making me feel. I was able to locate my sister's dance bag and slip into my sister's black tights and black short sleeve backzip leotard after first stepping into a pair of silky panties in the hamper. The feeling of being zipped up in her leotards and tights was so amazing I have been hooked ever since looking for any excuse to wear them, but was terrified of getting caught wearing my sister's dance clothes. Nevertheless girl scout day for sis became my weekly girl time to pad about the house for a couple of hours zipped up in her leotards with the silky panties peeking out under the tights. While dressed I put the dance bag back in her closet and kept my clothes in the bathroom so I could make a quick escape if someone came home early. One day my worst nightmare almost occurred when I heard a car door slam outside and quickly went to unzip the leotard only to find the zipper stuck so I could not get them off. I decided to duck into the bathroom and put my clothes on over the leotard and tights to give me time to work on getting out of them later. I felt strange stuck in them under my clothes with Mom and sis present for about an hour when I finally went back in the bathroom and was able to get the zipper unstuck. Later I was able to sneak her leotards and tights back into the dance bag folded the way I found them. It was a close call but it did not stop me from my weekly girly time wearing her dance wear and old recital costumes about the house as well as her nylon one piece suit she wore for swim team and pantyhose when she started to wear them. As I grew older I found some of Mom's tights and bathing suits to try on.I knew it was wrong but I just had to know how it felt to wear these female outfits so different from anything I wore as a boy. Anybody ever get caught like this?

[XemmaX]

8 or 9 maybe..

[ElisabethK]

For me I started with pantyhose and tights at around age 5. Refused to have interest in anything else until I became curious about heels at around 15, then finally went for full dressing once I was around 20.

[suspender]

I was 10. I remember the day well, and that was over 40 years ago.

[VeronicaBea]

I was 13, and I was about the same size as my mom then. When the house was empty for the next few years I would wear my mom's panties, bras, pantyhose, and dresses around the house. I feel bad about invading my mom's things without permission now, but I'm so glad that I did it because it has made me a happier person. Plus, being girly for a while is so much fun.

[bomba]

when i was very young around 7&8 i hung out with my sister(one year younger) at her friend rieta, next store.we were so young.we played with barbi dolls.then one day rieta brought us into her older sisters room and we started trying on her cloths and playing acting games.i will never forget the pink tutu outfit i would always wear.a pink body suit with the ballerina tutu and tights.in the games we played i always was the one to do what ever they told me.

[Aylineira]

Before I was 5 that's for sure - I had put on my Mother's red heels and walked around in them. Few years pass and around maybe 8 years old I'm in my sister's drawer stealing undies and pantyhose and wearing them. I also remember when I was in 5th grade and I underdressed with the undies and showed them to my friends (who thought I was weird). Too many memories!!

[Xandra]

I was 10. I remember the day well, and that was over 40 years ago.

Interesting that you say that because I remember the first time well. What happened in later life was validation of that.

[Bryn]

I guess I remember trying on bras and stuff when I was a kid, then in highschool I crossdressed once or twice with clothes borrowed from a friend (just a woman's shirt/pants)

[jane]

i started like most people here apparently, stole some white pantyhose to my sister when i was 12... i was hairless at the time so it looked/felt incredibly good

[seemlessph]

I always enjoyed when my cousin would play "dress up" with me in her tights and leotards from ballet class. We were probably 5 or 6 yrs old and loved every minute of it. Always played in her and her moms pantyhose too...innocent fun

[Brandi Lesalle]

I remember in my prepubescent years looking at alll the lingerie in the jc penney and sears catalogs and wondering how wonderful it must feel to wear all that silk and satin all the time. One thing lead to another and I began like most sneaking things to try on

[CathyGal]

I think I was 12 or 13, we were cleaning out closets in our home and an old mini skirt was tossed my way. A few days later I tried it on, along with my mom's pantyhose. Later it was my sister's clothes as well as mom's, and much later I bought my own clothes.

[mirima1992]

14, sisters high heels

[Aly Cat]

I had forgotten how fun this thread is! I enjoy reading everyones stories.
I think I have already replied to this thread like 10-15 pages back lol. For me, like most, I was very young. I remember when I was 5 or so dressing up with my sister in my moms skirts (which went from my shoulders to the floor). We would put sand buckets on our heads and stomp around the house with our fairy wands in our hands like little fairy soldiers. Other times, I would wear my sisters socks which had the frilly lace on the tops of them, wear her nightgowns when no one was around, etc. I continued to wear her clothes in secret until she moved out of the house when I was around 16. If only she knew back then, she would have bought me my own stuff. Then I could have been wearing my own and not have to have stolen hers! Or so she says now that we are all growed up. We have always been best of friends.

[carrie2014]

When my first wife left me for another man I cleaned the house found pantyhose bras panties and and lots of other clothes. Tried them on, I was 35 years old, It was great! The rest is good times.

[Brea Lynn]

I was 12 or 13, and rummaging through my closet of all places, it was used as a spare for a bunch of things that didn't fit both my parents since it was pretty large. I found a Fredricks' babydoll and another nightgown, both of which I tried on and wore several times after. What was the real deal sealer for me was the absolute very first time I put on that babydoll, I also had my very first orgasm, so it probably subconsciously locked into my brain that CD-ing feels good. :P

[Martha G]

I know that I have answered this question in the thread "from an older one" but not sure on this one.

Well, here goes.

I donned my first dress late in life at age 59 and WHAT a dress it was!

I was dressed as Donna Lucia d'Alvadorez ( Charley's Aunt) from the play Charley's Aunt for a costume party.

The dress ( which had some lace brocade on it)was a hoop skirt supported by a 115" hooped lacey petticoat. I wore a wig with ringlet curls, a bonnet, carried a small string purse and a black lace fan. Underneath I wore satin pantallettes with a lot of lace. The makeup was minimal. It was a lot of fun.

Since then I have developed some other female costume characters such as a midieviel Duchess and a Southern Belle.

[Felicia Dee]

I started cross dressing when I was 11. Never felt comfortable around guys and this made it even harder to actually be a guy. Now that I am older, I feel like I know myself better and have found a good balance. I can enjoy my maleness but love the freedom to explore my femme side from time to time, too...

[kev.wong140]

January this year.

[Xandra]

I started cross dressing when I was 11. Never felt comfortable around guys and this made it even harder to actually be a guy. Now that I am older, I feel like I know myself better and have found a good balance. I can enjoy my maleness but love the freedom to explore my femme side from time to time, too...
I echo your sentiments. Beautifully stated.

[sonialexis]

It would have be around when I was about 8 or maybe 10 I would wear my mother's panties, I remember the silky, soft tissue like material. Then about that time I came across her stash of stockings and pantyhose. I have rarely felt so excited as I tried each and every one. fun times.

[Rosie87]

I think I was about 6 when I was staying at my grandparents' house. I remember wearing a dress out of the cupboard and pretending to be a girl in front of my brother. I also remember stuffing the dress under the bed when I heard my grandma coming up the stairs! Didn't try it again until I was 13.