When did you first crossdress?

[xandralovesleather]

Looking back, I can remember putting on my mum’s coats when she wasn’t around and admiring myself in the mirror when I was 7 or 8.

[Krea]

I think many here have childhood origins to their CDing, so i'm probably in the minority coz i only began crossdressing a few years ago. (i am forty-something)
Looking back tho i have always had much insecurity about myself, without actually knowing what caused it and i feel much happier about who i am now i can crossdress with the support of my wife.

[Alice_2014_B]

Completely from wig to heels was around January 2014.
:)

[sometimes_miss]

The first time I wore girl clothes was as a toddler when mom dressed me in my older sister's hand me down clothes, ostensibly to keep my from ruining my 'good boy' clothes. She also kept my hair long, I remember her giving excuses like running out of money, or time and needing to catch the bus when at the end of a day shopping when she had planned to get my hair cut. This went on until I was just past three, when my dad came home for lunch early and found me in a dress and blew a gasket. So that stopped, as well as him deciding to take me to his barber regularly from then on. The first time I dressed myself in my sister's clothes was when I was four, she, getting ready for school and mom getting her prettied up and doing her hair, I went and put on a dress and then went and told them that I was ready to go to school, too; basically probably a maneuver to get mom's attention to me. Mom simply changed me back, and we took my sister to school. When we came home, she asked me if I'd really like to wear the dress, but said it in such a way as to imply that my answer should be NO (as in, "you don't really want to wear a dress like your sister, do you?"). So that's how I answered, even though my feelings were actually 'YES'. But it wasn't a statement of wanting to be a girl, just not wanting to be dressed in my worn out ugly boy clothes, and of course, wanting her to be nicer to me. Mom was a first born, as was my older sister, and so mom sympathized with sis whenever sis complained about me, because mom resented her younger sisters when mom was young, and still did throughout her life, often complaining that she had her life limited because of her own mother's insistance that mom watch over her sisters, and that her sisters always were shown preference instead of her. So I suppose my mom's behavior showing preference to my sister might well have made me feel that it would have been better to be a girl, instead of a boy. Still, this didn't make me feel any more female at all. That would change a few years later, when I was molested, and told that god had made a mistake, and that I was really supposed to be a girl. He presented his reasons, which at that age, I wasn't able to debate. So, thinking that I was supposed to be a girl, I developed a desire to dress as one and behave as one, in order to be good and hope that god would eventually fix my body, too. My abuser dressed me in his younger sister's clothes regularly, and over the next seven years, made me into his own personal girlfriend. By the time high school rolled around, the notion that I was supposed to be a girl, and wear girl clothes, was firmly set into my mind, and even though all evidence that exists tells me that it isn't true, the feeling has never gone away; I still feel like I'm supposed to dress and behave like girls do. The problem is, I'm not attracted to boys, only girls. And I don't see and experience the world as girls do, nor communicate like they do, or behave as they do. Whenever I got the chance, I would scrounge up some of my sister's old clothes to dress up in, always hiding it from the rest of the world. So I'm in an odd position, feeling like I'm TS while retaining my male desires and thought processes. I'm neither all girl, nor all boy. And for the past almost 50 years, have felt like an adolescent girl, forever waiting to become a woman. Needless to say, despite praying endlessly throughout my childhood, god never got around to answering my prayers or fixing my body. The whole story is in my bio, link is in my sig at the bottom of thiis post.

[NancySue]

When I was 5 or 6, I found a pair of mom’s sheer nylon stockings. Don’t remember “why”, but felt a strong urge to try on...and did. That was the kickoff and the game continues.

[Tracii G]

1968 I was 15 went to the prom.

[Beverley Sims]

I think about four or five when playing mothers and fathers with older girls.

I was the little baby as I could be put in a large pram and wheeled about.

I thought this was good fun as I was given a bottle with warm cocoa in it.

That I did enjoy, I liked cocoa.

After that I think it all got imprinted on me like a chicken to the mother hen.

[wanda66]

In the beginning.......

[Taylor186]

I was six when I fashioned a dress out of a towel. (Is that crossdressing?) I was seven or eight when I discovered stockings that were hanging on the towel rod to dry. It progressed quickly from there.

[carhill2mn]

About age 8 when I put on one of my mother's silk blouses. It fit me like a dress and I loved it! Soon I was wearing her wedding dress as often as possible.

[Paula2]

Nice question..I cannot tell you when I started..1976??
I have done it all my life..I cannot tell you when I started..I have done it since my very first memories..And yes Taylor I too remember making skirts out of towels..LOL..now they are called "Wrap Skirts"

[DIANEF]

I first wore a dress when aged 15, that was in 1979. Many years before that all I had worn was underwear and swimming suits, after that I only ever wanted to fully dress.

[jaerina96]

I don’t really know, literally it’s been as long as I can remember. I don’t remember trying on my first dress. By the time I was 10 I was already “wig to heels” in the hours between getting home from school and when my parents got home from work, a mix of old dresses my mom kept in the trunk with the Halloween costumes and things I snuck out of the bags of stuff that was supposed to go to Goodwill. I’d pad bras with polyester filler, and had a cheap old costume wig. Things fell apart after getting found out a few times and lectured / screamed at about it being a sickness and going to hell, that sort of stuff. Body hair was the real killer for it, I couldn’t get rid of it without being noticed and it grossed me out so bad that I couldn’t continue. Then I ended up in one of those church youth cults, went through a very very long self-hating religious phase, and after an extremely bad prolonged depression stopped fighting it and started again around when I turned 30. First time out in public was less than a month later. With the exception of a year and a half pause when I had a serious relationship, it’s been a regular part of my life ever since.

[Jenny Brogai]

I started around 12 or 13 with my mum and my aunts stuff, never forget the thrill of it! The first time I dressed up in a wig and heels, I was 25.

[t-girlxsophie]

When i was 10 in my Gran's house,first wore my aunties clothes that she had left there,still can't explain what drove me to do it

[Tracii G]

Sophie I don't think any of us could answer the question why and trying to pinpoint an answer is a fruitless venture that just causes more questions.

[Chloe Triss]

Around like 11 years old when I was alone in my house for the first time, I went on and wear my aunt favorite victoria secret undergarment set and her big red black spotted dress.

[Lana Mae]

Mom's undies in elementry school! Mom's nylons, long leg pantygirdle, bra and full length slip in my teens! Fully; wig, forms and make up going on 3 years! All started when Lana(my namesake) flipped her dress over her head and I wanted a dress to flip over my head! LOL Hugs Lana Mae

[Diane Smith]

Among my first clear memories are my mom letting me try out her lipstick and earrings at about age 2-1/2. Nail polish followed soon after. No clothes at that point, but by 5 I was playing with her shoes, stockings and girdles.

- Diane

[Esther Latour]

When I was in the first year of art school, at a fancy dress party. It was supposed to be ironic but of course it really wasn't. I had been having fantasies about it for years.

[chelyann]

7 or 8 when I was left home alone for a little while

[sara66]

I was around 5. I found one of mom's bras. By the time was a teenager my mom's and sister closets were my playground.
Sara :heehee:

[Jodi]

Eight years old. Discovered my moms high heels

Jodi

[Raychel]

i was probably 7 or 8 when I first started with the underwear and pantyhose.
that progressed over the year to full dressing when I was 43. It has been almost 15 years now.

[Jenn_8B]

I don't know when I first cross-dressed. I can vaguely recall trying on some of my mothers clothes, probably as a teenager. I have been overweight most of my adult life. About 10 years ago, I lost a lot of weight and started trying on some of my wife's things. Several years later as I gained the weight back, I had a desire for "softer / sexier" clothes than men's clothes. Somewhere about then I started wearing panties with my wife's permission and things grew from there.

[Jaymees22]

I know I was 7 because I was in the second grade production of "Cinderella". I played one of the ugly sisters, type casting? Anyway I looked happy so it must have been the start of something, I wonder what?

[alwayshave]

I know I was about 4 or 5, my mom kept stuff on the stairs to the attic which was in my room.

[Tracy Irving]

My best guess is somewhere in the six year old range when I discovered how wonderful it felt to wear my mothers panties.

[kayegirl]

It seems so long ago now that it's hard to be precise. I had been playing dress up since the age of 5 or 6. Somewhere I even have a photo of me wearing my sister's bathing costume. But I was 13 when I first consciously dressed full girl. Home alone and again with my sister's clothes. For me it was a true epiphany, and I knew that I wanted to be that girl forever afterwards. Sadly it took many years before I could be as open as I am now, but that's another story, and too long for now.

[Megan b]

I was 12/13 when I tried on a pair of my moms pantyhose for the first time. I was hooked from that moment on. Shortly after the hose came panties, then girdles, slips, bras and finally a dress. No wig or makeup till years later. But now I can't really imagine not being a crossdresser, it's just part of me.

[MarinaTwelve200]

I started with Mom's lipstick at age 12------Since I was 8 In the late 1950's,I remember the (joking) threats by Mom other women and older girls at our consolidated School, to put that red 1950's lipstick on me. The idea horrified me. especially since I thought it would not come off. The worry was for naught, none of them ever followed through with their threats----Although I came pretty close when, at a whim, Mom had dad hold me down, one time, to actually do just that, but "chickened out" at the last second "I don't know, it might give him a complex" was her excuse.-----But the prospect fascinated and horrified me for years later---at about age 12, I was left alone at home for some hours, and decided "what the heck, GO for it!" I first tried a touch on my wrist---and behold! it wiped OFF!---Then on my lips it went.----at age 13 I tried on a girdle, some panties and nylons from the laundry---THEN, (why not) a bra (stuffed with my underwear) and a slip and finally a housedress to top it off---Then Lipstick (of course) and a scarf to cover my head.---I was Completely Dressed! ----And continued (with some breaks) when I could, to this day.

I still have some "holdovers" from my roots--I need the darker shades of red Lipstick to really feel "dressed". Yes, I have tried other shades, and I really look good (if not better) in them, but I just cant get my "rush" in anything without the red lipstick. (the 50's influence is still there, I suppose) Perhaps it is a "fetish"

[Anna Stouf]

The year was 1954. I was 10 years old. On Halloween that year, Mom sent me to school completely dressed as a girl. Panties, slip, and pretty dress. I loved it soooo much.

Been doing it ever since.

[mdavis]

I started in about grade 6 or 7. Same as many. Tried on a pair of my mother's nylons. Loved the feel of them. Progressively would try on some of her clothes as well. There was a pause for several years until shortly after I got married. That was about 27 years ago. I've dressed on and off since then but, for the last three to four years have dressed more and more fully (wig, full outfit, at the very least lipstick) and today purchased some of my own makeup to try.

[michelleg]

About 11 or 12, home alone and got the urge to try on my Mom's slip, it felt wonderful and I loved it. So then came the panties, bra and stockings, heels that didn't fit but still looked nice. Took a look in the mirror and was hooked, anytime after that when the opportunity was there I was dressed.

[krissy]

I was 6-7 i used to wear my sisters clothes .when mom didnt do laundry i would wear her panties .loved it:daydreaming:

[Lacey New]

I guess that depends on how you define crossdresing. If it is the very first time that a person wears an item of cloting of the opposite sex or is it the very first time that a person wears an item of the opposite sex specifically for their pleasure? I remember one time when I was about 10 at my Aunt and Uncle's house playing with my female cousin in the creek. We got all wet and muddy and my Aunt put me in a pair of her side zip bluejeans while my boy jeans were in the wash. That was when I was about 10 and I thought nothing of it. However, by the time I was 13 or 14, I was "borrowing" my mothers and sisters panties for my pleasure. And while I don't remember borrowing any other lingerie at that time, I knew that I wearing women's clothing was exciting and that I wanted to wear more. So I guess that was the start of my crossdresssing.

[Ginni]

I was around 11.

[stephNE]

When I was about 5, I remember going into my mom's dresser and getting out a bra and panties. I loved hooking the bra and spinning it around. Of course the panties were too big, but I would put them on overtop of my little boy clothes, and tuck the panties into my waist band to keep them up. I would put them on, and go back to my room to play.

There were two boys in our neighborhood that were about the same age as me, but I didn't like playing with them, they liked playing outside and getting dirty. The house across the street from us had three daughters, all older than me. I loved to play with them. At least once (also about age 5) they dressed me up in a dress with shiny black patent leather shoes and white socks with ruffle tops.

[Georgina]

I was somewhere between 6 and 10 years old and my first garment was my mom's slip. Never looked back since.

[Elizabeth G]

I was right around 11.

[Satellite]

It was when I was 13. I was home alone for 2 days and I went into my mom’s lingerie drawer. It was full of panties, stockings and pantyhose. I was in heaven. I put on my mom’s panties and stockings attached to a black suspender belt and I started walking around the house. It felt so nice. I could not resist and I took a pair of pantyhose for myself. I would wear them everywhere I go, under my jeans of course. I used to hide them under my pillow until my mom found them while cleaning my room. We had a conversation and she told me that I should have spoken to her about my curiousities. She asked me if I tried on anything else while I was home alone and I told her that I tried on her panties and stockings. My mom was surpised that I was honest to her and she told me that I shouldn’t wear someone elses underwear without permission. She also asked me if I liked wearing panties and I told her that I fell in love with them because they were so comfortable. She told me that we will go out shopping tonight. That night we went in town to a lingerie shop (i don’t remember the name of the shop, sorry!) and she told me to pick the panties that I liked the most. I remember choosing some purple hipster panties. I tried them on until I found the right size. The experience was so nice. She ended up buying me panties so I wouldn’t use hers again. The next day she came home from work and she told me that she bought something for me. It was a pair of black pantyhose. I hugged her and then I thanked her. A few weeks later, everytime I went shopping with my mom I was asking her if I could get another pair of panties and she never refused me. Best mom ever!

[Michala]

Don't remember the exact age but pretty young. Put my mom's bra on and then her nylons, no pantyhose back then. As I got closer to my teen years I developed gynomastia and then bras started to fit better. No one ever knew, other that probably my mom as I'm sure she could tell when I had worn some of her stuff. She never said anything and I would have died if anyone ever caught me.

[Cherylgyno]

I was 6 year's old. I wore my mom's pantyhose, rib knit body suit and bra.

[candice.aihara]

I was twelve years old when I slipped into my first pair of panties. They were purple with tiny white stars. The panties were a bikini cut made of soft cotton with a tiny lace trim along the waist. I felt excited and nervous as if I was doing something deliciously forbidden. My head was spinning. Around the same time, I paired the panties with a demi bra. It was lightly lined for a subtle lift and had underwire cups. It was probably made of nylon and spandex. I distinctly recall it was coconut white. The feeling was sublime!

[BillieS]

I was 8 or 9. I tried on my mom's bra and girdle, and almost got caught!

[xandralovesleather]

What a memory! I love how you bring it to life with your words.

- - - Updated - - -

It was meant to be!
When I was in the first year of art school, at a fancy dress party. It was supposed to be ironic but of course it really wasn't. I had been having fantasies about it for years.

- - - Updated - - -

That's some mum!
It was when I was 13. I was home alone for 2 days and I went into my mom’s lingerie drawer. It was full of panties, stockings and pantyhose. I was in heaven. I put on my mom’s panties and stockings attached to a black suspender belt and I started walking around the house. It felt so nice. I could not resist and I took a pair of pantyhose for myself. I would wear them everywhere I go, under my jeans of course. I used to hide them under my pillow until my mom found them while cleaning my room. We had a conversation and she told me that I should have spoken to her about my curiousities. She asked me if I tried on anything else while I was home alone and I told her that I tried on her panties and stockings. My mom was surpised that I was honest to her and she told me that I shouldn’t wear someone elses underwear without permission. She also asked me if I liked wearing panties and I told her that I fell in love with them because they were so comfortable. She told me that we will go out shopping tonight. That night we went in town to a lingerie shop (i don’t remember the name of the shop, sorry!) and she told me to pick the panties that I liked the most. I remember choosing some purple hipster panties. I tried them on until I found the right size. The experience was so nice. She ended up buying me panties so I wouldn’t use hers again. The next day she came home from work and she told me that she bought something for me. It was a pair of black pantyhose. I hugged her and then I thanked her. A few weeks later, everytime I went shopping with my mom I was asking her if I could get another pair of panties and she never refused me. Best mom ever!

[Scarlett398]

I was around 9 or 10 and found one of the drawers in my mom and dad's room full of sexy black thigh high hose, panties, garter belts, and black lingerie. Everything in that drawer was black and sexy and I just couldn't resist trying on the black thigh high hose, a pair of her black panties, the black garter belt and found out real quick how to attach the black thigh high hose to the garter belt, and one of her sexy black bras.
I just had this sensual sexy feeling all over my body and in my mind. Upon further snooping that day while no one was at home, I found my father's Playboy magazine collection hidden underneath the bed.
Well you girls can just imagine what I did myself when I laid down on the bed with all of that sexy black stuff on with my dad's Playboy's open and next to me! After that day, I've been hooked ever since.
I've personally tried for many years to take my cross dressing to a the highest level possible and I'm always looking for ways to improve.
Thanks for reading my note...Sincerely Scarlett :heehee:

[jennifer0918]

I was around 10 years old I wore a pair of jelly shoes back in the 80ies.

[JennyLiz]

I was about 12 or 13. It was my sisters swimsuit, then her panties. Been hooked ever since, swimsuits are still one of my biggest enjoyments to this day.

[jamienoir]

Since I can remember. I got spanked when I was 5 or 6 for wearing my sisters panties. By the time I was 10 I was full blown dresses, heels, makeup etc. I can't imagine why I started. I would go to the local library and get books in transvestim and hide in a remote corner reading the very adult theories. I then discovered the term drag queen due to an article in a magazine abt La Cage. That really gave me more subject matter to look up!

[dana digs sweaters]

Kind of like this :battingeyelashes:

290645

[Diane Taylor]

I was a late bloomer if you mean fully dressed. I didn't fully dress until I was in my 40's. if you mean a few items of underdressing, I was in my 30's, but when I was 8 my mother made a Halloween costume for me that included one of her short dresses and some lipstick.

[Sandra_Dodds]

Somewhere around the age of 7 or 8, when I first tried on mum's tights. I have a distinct memory of being in primary school and seeing a girl in tan colored tights with white knee-high socks and being totally fascinated with how those tights looked and felt.

[xandralovesleather]

Love that.

[StefaniLara]

Gosh, I can't remember that far back! I would have to say around 12 years old, right around puberty.

[CONSUELO]

This thread repeats a very common topic. While it is always interesting to see how others first began to dress in female clothing the question I always have is rather different. I'm sure that many young boys experimented with trying on female clothing at some stage in their young lives. But how many found it thrilling and incorporated it into their lives from then on?
A young women told me of how she used to dress her younger brother as a princess for her games. He would play along with it but he never became a cross dresser. I wonder why?
What is the cause of the trigger that turns a single dressing occurrence into a life time need/

[Heather Anne]

As a teenager in the early to Mid-1960s I was constantly getting into my sister's things. Unfortunately I was also getting caught by my parents. One time I wore her GoGo boots, busted the zipper and had to take my allowance and buy her a new pair.

[lynnmcarthur]

I was 4 or 5 and had thought about being a girl around that time. Going on 66 yrs of feminine thoughts

- - - Updated - - -

And in reply to Consuelo, I was thrilled form the beginning

[Fiona Lindum]

I started with tights and underwear when I was about 14. Progressed to skirts and dresses in my 20,s.

[immike]

My dressing began years ago,probably 15-20 years ago,as I began experimenting secretly,wearing mothers clothes.I would wait for her to leave for work,and lock the house&close windows and blinds,and each morning I would spend mornings trying on her dresses,
and skirts,and her soft,silky blouses&her dress slacks&regular shoes.Over time,I got bold&lifted a fresh pkg of beige pantyhose,put them on&added a short dress,or skirt and a blouse&began trying on her heels&learning to walk around the house in heels.As I became better balanced,I began trying on all of mothers good outfits,all of her pantsuits&I would dress in one of her expensive skirtsuits&sit at her makeup table&try on one of her wigs&spend mornings dressed.My favorite outfits were one of her mini skirts,a soft
silky blouse&her double breasted blazer,a pair of off black pantyhose&heels

[Stephanie47]

I've always taken the position that donning a singular article of women's clothing does not make a cross dresser. Does a guy who dons female attire as a joke on Halloween make him a cross dresser? I think not. to me there has to be some feeling or motivation coming from the inner self to do it. A cousin forcing a young boy to wear girl clothing is not cross dressing.

That being said the first time and subsequently I wore my mother's nylon full slips. I had zero desire to be a girl. It was nothing more than the feel of the fabric. Nylon was like no fabric I had in my boy clothing. First it was fondling the nylon as the slips dried in the hallway of our apartment. Finally, I had the desire to put one on to see how it felt on my body. The slips felt wonderful. I still had no desires to proceed further....until puberty....when hormones started to rage. Then came the panty, bra, slip, hosiery, and, the one dress I was able to fit into. Then came the confusion in sexual identity. What caused the compulsion to wear women's clothing? That was when I feel I became a cross dresser, a confused young teenager wearing his mother's clothes.

[immike]

I thoroughly enjoyed wearing mothers clothes,we were the same size&height&I never worried about stretching anything,like a skirt,or a blouse& I would shower,so the scent of perfume would not be on me.I always ordered frilly undies&pantyhose online&had it
delivered to a UPS mailbox,and soon all of my wardrobe was ordered online.I still have a key to mothers house,to keep an eye on animals when she travels,but I still enjoy dressing in her good wardrobe,especially her good skirtsuits

[Queen Bridget]

I tried on a pink frilly dress when I was 15.

It put a spell on me that still hasn't been lifted.

[texasm31]

OMG. I do remember doing this too!!

- - - Updated - - -


I was six when I fashioned a dress out of a towel. (Is that crossdressing?) I was seven or eight when I discovered stockings that were hanging on the towel rod to dry. It progressed quickly from there.

OMG. I do remember doing this too!!

[Jessica S]

I was helping my mom sorting socks and a pair of my mom's Knee-hi'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 else

[Rhandi Spencer]

My sisters used to dress me in little girl clothes when I was very young, they thought it was just wonderful having a baby sister.
I was 15 and house sitting for some friends and I would go into the daughters room and try her stuff on but it was all to small so I ventured into the moms room, tried on panties, bra's girdle and panty house. For whatever reason I never tried my mom or sisters clothes on. I tried my wofes bra and panties on once and determined then that I needed my own garments.

Game over

[Desiree2bababe]

I've been walking in heels since the age of five, started wearing sister's slips at age of 8, went full drag age 15. It's been a lifelong affair.

[BLUE ORCHID]

Xanten :hugs:, Probably around day two or three when Mom dressed me in that pretty little White receiving Gown,
when I came home from the Hospital, I was hooked for life

Around age four I would play with Mom's heels & Hose and the rest is History.

I've been in this program for 71yers now.

>Orchid...:daydreaming:...

[KelleyB]

I was 6 or 7, found one of my mother's half slips in a closet, and tried it on. Shortly after that, I added her panties.

By age 10 or 11, I'd started wearing her bras and dresses as well.

I like to think I was never caught, but that's likely wishful thinking.

By age 13-14, I had started building my own wardrobe.

[Rhonda Jean]

I was 5 or 6. My dad and brother were painting the house and my mom and sister went to the grocery store. I was alone inside the house and decided to play with my mom's makeup. When I heard them come home I hurriedly tried to take it off and found out it didn't come off that easily. My mother came in and called for me and I was in the bathroom with the door locked. I was petrified. She made me unlock the door and, of course, saw me with the smeared remnants of makeup all over my face. She said, "It doesn't come off very easy, does it!" She took it off and told me not to play with her makeup, that if I wanted to play with makeup to ask her. I don't remember ever asking.

I had long hair even back then, and at about that same age I remember her rolling my hair for a family reunion dinner at a restaurant. I've been told that wasn't the first time, but that's the first (of many) I remember. Also at about that same age, maybe a little younger, I remember being out in the garage where the washer was and getting one of my sister's skirts out of the dirty clothes and putting it on and twirling around the garage. My dad opened the door to call me for dinner. Nothing was ever said about the skirt.

[Kay222]

I seem to be in the minority, like Diane. I can't remember really ever having a strong compulsion to cross dress until the past few years, and I just turned 60. I don't think I had been purposefully suppressing something, but maybe I was. Who knows. But I certainly enjoy it now.

[stephaniestilley]

I remember trying on one of my sister's dresses when I was 8 or 9, but the first time I fully cross dressed was when I was in 10th grade and I managed to get a hold of a dress, a bra, a pair of panties, and a wig and went for a walk around my neighborhood really late at night so no one would see me. It felt really interesting until a police officer drove by and stopped me and I got really scared. I made up some story that I was doing this as a dare and he just let me go home. I was so scared that my parents would find out that I immediately ran home and was shaking like a leaf for the rest of the night. I never talked to anyone about because it was a really terrifying experience. Until recently, that was the last time I cross dressed and now I wear dresses and skirts more than I wear men's clothing

[Ashley090]

Being dressed in costume of Forest Fairy by my mom for kids party counts as start? Then its about when I was 4. Dressed on my own was when I was 7. But it has been only two years since I ventured out to world.

[Amymonroe]

i'd say somewhere around age 13. it started with under wear and bathing suits and casually went on from there.

[Heather Anne]

The first time I was dressed completely from head to toe en femme was during a makeover with Phoebe Cross, near Atlanta. She gave me the phone number Sigma Epsilon Atlanta. My first meeting was on a Friday. Saturday I came back. Changed clothes applied makeup and went to Ruby Tuesday for lunch April 2004. The first time out in public completely dressed en femme. Prior to that was when I was a teenager always getting into my sister's things (mid 1960s) and getting caught by my parents.

[AllieBellema]

I was 17, if I recall correctly... it was a wig and a sock hop costume I bought at the local K-Mart. Not sure how I got the courage to take it up to the register to pay for it, but left it in the trunk of my car when I got home until I knew the coast was clear to get it into my room.

[Karmen]

I was secretly trying on mom's shoes since I was a little boy, but my real first crossdressing attempts came in my teens when I fully dressed in mom's clothes while home alone. At that time I also started wearing panties and pantyhose under my male clothes as much as possible while still living at home. I started fully dress, with wig and makeup and going out like that at night only in my 20s.

[Jennifer2918]

I was probably 8-9 and was in my parents bathroom which had the shower. Mom's nylons were hanging in there and I could not resist trying them on.

It laid dormant for a number of years after those years of nylons, but about 20 years ago (I'm almost 60) it came raging back. First was the wife panties, then my own panties, then nylons, then outer wear.

Just loving the adventure.

[Rollermiss]

I think I was 10-11 I bought (second hand) and wore one of my skating partners old costumes. Kind of kept snowballing from their.

Kelsey

[Amelie]

When I was 15 I was sort of androgynous in dressing, sort of like Bowie or a cast member from a Warhol film, kinda like a glam rocker. Think of the band "The Sweet". I knew I was a girl but didn't start to fully dress as a girl till late teens, then I became a punk girl.

[Cynthia T]

I remember exactly. I could even figure out the day if I worked at it.
An evening in May, when I was in 7th grade. Home alone, supposed to be doing homework but wasting time reading a paperback. One line in the book described the character getting stepped on by a woman in high heels. Bang!?!? I went back to my sister's room and put on a pair of her heels. Starting borrowing, scavenging, and buying my own after that.

[Victoria_Winters]

well I was always curious growning up. It wasn’t untill high school that I actually really wanted to. I saw Sherley Manson from garbage, my favorite band, in a pokedot dress and I wanted to wear it. I got my first clothes that belonged to me durring high school. My mother helped me at the store find something. Super awkward. And after I graduated and moved into my first place I actually started dressing up. That was years ago. I still have most of my original wardrobe including the first dress I ever bought. Can’t fit any of that stuff anymore but I can’t bring myself to get rid of them. I keep deluding myself into thinking I’m going to loose enough weight to don’t my old cheongsam.

Love that dress. I fell head over heels for it when I saw it and bought it on the spot!

[Maria in heels]

I just love this thread every time it comes back up.....

My first time was when I was about 7 years old and I discovered the world of my grandmothers bra in the bathroom on the drying rack. From there, it jumped to her black patent kitten heel pointy shoes (those killer ones from the late 40's to early 50's). Then behold.....my stepmothers closet with those fabulous pair of round toe black patent platform pumps with those 4 inch block heels from the late 60's to early 70's....i'm still looking for a pair that is just like those....

[--Nina--]

I was 10 my room was in the basement so was the laundry room.

[Shayla]

That is the best Mom ever Satellite!

[missynicole]

i remember putting on my mom's bra and panties when i was about 11 or 12.....no one was home at the time.....i did it many times

[Angela Marie]

I was about 8 or 9 when I tried on a pair of my mothers black tights. I was immediately hooked. I will be 64 next month so, as many of you probably know, I grew up in a much more repressive area as far as cross dressing was concerned. I’m a runner so when running tights were introduced you can imagine my exhilaration lol. I did not start fully dressing until about 54. I often wonder how things would have turned out if I were in my 20’s today.

[IamWren]

I have worn items intended for women, once or twice here and there, as far back as 30 years but it wasn’t but just three years ago at age 48 that I wore women’s clothing for the deliberate purpose of trying to look like a woman.

I’ve learned a lot on how to to do that better and have even, with the help of members from this site who live in my area have found the nerve to go out while dressed.

[darla_g]

i was a young teen in middle school. I put on my mom's stuff while she was away. I somehow decided that my brows were too thick and i proceeded to shave half of them off.

It was torture in middle school! I wouldn't cross dress again for another 15 years. below was my next attempt.

[Robin777]

I was around 12 or 13 and tried on my mothers panties. Then it went on from there.

[Rachel05]

I was 8yr old and it was my mums panties, I have no idea why I felt the need to try them but I do remember feeling good about it even back then and here I am 50 years on and crossdressing me still feels good

[BobbiKay]

In my middle teens I explored my mother's drawers, including the one that held her drawers. I tried on her girdles and hose. Loved the look and feel of the tight Spandex and the nylons secured by garters. Still do, but now it's leggings or jeggings. My sister was younger and smaller than me, so no opportunity there. As a 30-something, I would sometimes wear my SO's pantyhose under my suit to the office, and her bodysuits around the apartment.

[KellyGCD]

I remember as a kid, trying on some clip on costume jewelry, so I guess that was the "first" time. As a kid in middle school, I definitely tried on some of my mom's clothes. I guess the rest is history from there.

[Sashauk]

I was in my early teens when I discovered my older sister's knickers and bras. I got such a wonderful feeling when wearing them that 50+ years later I'm still wearing knickers and bras.

[Charlotte7]

It was so long ago, before I went to school. I can not remember a time when I didn't want to wear girls' clothes. The first time I remember was one summer, I just wanted to wear one of my sister's summer dresses. I asked my mum, (possibly I pestered my mum) and was allowed to wear one for an afternoon. Then, there was a time when we were on holiday, we were on the coast and took at boat trip to a nearby island. The crossing was rough and I got quite wet and had to change. I didn't have any spare clothes and so my mother put me in a pair of my sister's shorts. They were just red shorts, but, even aged 5, it meant so much to me that they were girl's shorts. Then, another time, around about the same age, we were visiting our cousins and for some reason it was decided that we would play doctors and nurses and I was able to wear the nurses dress. Then, as has been mentioned before here, I discovered towels and for a while I enjoyed what I called my 'Fashion Shows'. Then, I discovered where my mother kept her underwear and, after a short period of overdressing, I started wearing them properly, and then I wore them as often as I could. And the rest, as they say, is history.

[elliemoss]

I was about 13/14. Out of nowhere I started to notice what ladies were wearing on TV and at night time in bed I was bombarded with thoughts of femme clothes. I finally gave in to an over bearing urge to try on some of my sisters dresses and skirts. It felt amazing and ever since then been hooked. Wassn't until about 10/12 years later until I fully dressed up with wig/full make up/heels. My GF at the time was away for the weekend so I had a girly Satruday watching girlie movies, TV then got dressed up and walked around the block late at night. It was such a unique thrill feeling the cold November wind blowing my dress against my legs and the clipping sound of my heels on the pavement.

[faltenrock]

Can'r remember exactly when, but I think I was around 12-13

[Marie Boisvert]

For me it started around 8 years old. I tried my mother's bra on. I was hooked ever since. 40 years later I have never looked back. I have enjoyed the progression, I look forward to another 40. Marie

[Mary Lawrence]

I have dim memories of being a 5-6 yr old, following my mother as she shopped in a nearby department store. Many of those visits entailed walking through the lingerie department in order to get somewhere else. When surrounding by all the bras, panties, girdles and slips that were on display, I covertly looked at them. To this day, I still don't know why the looks were "covert" and not "with longing" or simply neutral. Regardless, when in that surround, everything felt surreptitious to the point of giving me an odd sensation in my belly and embarrassed me. With the hormones that came with adolescence, I again felt the same pit-of-the-stomach fluttery sensation when around my mother's panties, bras and girdles, but the feeling was also accompanied by an overwhelming urge to try everything on, particularly the panties and girdles. That continued, in secret, through high school. I was married soon after college and my wife's panties (girdles were out by that time) fit nicely! Only after our first child was born and I was in my thirties, did I dress completely in my wife's clothes. There was no wig or shoes yet, but after that full dress event, I long for more opportunities to repeat it, but now in my own skirts, wig, slacks, bras, panties, slips, jewelry, makeup and, yes, shoes that fit me. But, I don't yet have a decent pair of boots.

[Melanie Vee]

I was in 4th grade and I saw a clip of Jimmy James transforming himself into Marilyn Monroe on Entertainment Tonight. Later that night, I put on some of my mother's lipstick and blush as well as a tank top and bra.

[kathy chelan]

The first time I know of for sure is that I remember I would put on my sister's sandals when she took them off while we were playing outside...this was probably about when I was 5. She is 21 months younger than I, and I could wear most of her things until about high school age when my growth spurts started---girls have them earlier, you know. At age 6 in first grade, I had a short walk to where she was babysat all day, along with another girl her same age named Betty Ruth H. They had a habit of taking their shoes off and putting them under the edge of a table. When I got there I would wear Betty Ruth's shoes---black patent leather (ballet) flats. Mrs. K kept all 3 of us until my mom picked us 2 up after her work, about 6 pm.
Once we were invited to go swimming with the family of the girl next door to us who was my sister's same age. Sis didn't have a suit. so they loaned her what was then called a two-piece "sun-suit." That evening when we were at home and this was hanging to dry in the bathroom, I put it on and walked around like I did Betty's shoes at Mrs. K's. When my dad saw me, he bellowed at the top of his lungs for me to take that off and never to let him catch me doing something like that again. I sure didn't. From then I dressed in secret only, apart from a few times I talked mom into "dressing (me)up like a girl" to go trick-or-treating. Mom still had a matador costume from her high school years and both of us used that a time or two.
Once at Mrs. K's, she had twin granddaughters visit her (they were at least 5 years older than us 3), and they played with us while their mom was inside with Mrs. K, her mom. Since I again was wearing Betty's shoes, they suddenly decided they wanted to dress me up like a girl. I was thrilled inwardly, but dare not show it outwardly. But suddenly they were called to get ready to leave. I didn't let on to my sister or Betty but I was inwardly very disappointed. From 2nd grade on, I always wore my sister's things when no one else was home, and I was a sickly kid anyway.

[jeni]

My first time was when I was 16. It was in my neighbors Apartment she was dressing her self at the time. Wearing my first dress I felt at home with my self.

[laura.lapinski]

I had some thoughts at a very young age, and I put on a one piece stretchy, skin tight bathing suit when I was 13. Loved it.

[Barbara Jo]

OK....
I was born in '47 and had a sister 4 years older than me, and another sister that was 4 yeas younger then me.
Yeah, I am the middle child.

So early on, I had access to all that great 1950 lingerie and other female clothes from my mother as well as from my older sister... I was attached to their clothes... even before puberty.

When was almost 9 years old and my older sister was 13, she had made the transition to adult lingerie and clothes.
I kept wondering how wearing those clothes felt....
I cold not fight it anymore. At about 9 years old, I had to find out,
So, when I got the chance in private, I started with panties bra, slip Eventually I often added gaiter belt and stockings, a dress or skirt / blouse .
My sister's (and mothere's) clothes were just a bit big on me but, I absolutely love the way they felt.... they felt so right and pleasant .
I loved feeling feminine/girly. :)

[Patience]

5 or 6, from what I remember.

It felt right the moment I put it on.

Xox,

Tina

[Millisense]

I was fortunate enough to have a much older sister so there were always clothes of hers from various ages to be found in the attic or her bedroom after she left for college -- skirts, panties, pantyhose, everything. Just recalling those lovely afternoon dress-ups 50 years ago sends nice shivers, so thanks for the thread!