How old were you when you first wore women's clothes?

[qaws123uk]

How old were you were you when you first wore woman's clothes?

For me it was when I was about 7 in primary school - it was for some play and I had to dress up as a spider so that was a black leotard and black tights.

I remember we had to borrow a leotard from girls in the school - seems odd having to borrow some girls leotard and not having the parents buy a new one. I think the tights were borrowed too?? I guess since I didnt have a sister, parents would have had to buy some clothes which would never have been worn again. Is this when it all started??? :)

Of course I didnt think of this as "crossdressing" and it wasnt until I was about 12 I think when for whatever reason I wore some of my Mums tights. Dont know why - just did. Just wore tights now and then after that I think but not regularly.

[Terrihoney]

I can't remember exactly how old I was, early grade school, but I had a fasination with my Mom's bras. Of couse they were too big for my skinny little chest. My brother and two sisters shared one large room. Once, I stuffed with hanfuls of toilet paper and paraded around the room. Later, Mom found the wads of TP with her bra in a closet. Busted!
In 7th grade, I was a girl for Halloween, dress, wig, and make-up! Now, all growed up, I'm going to be a woman.

Hugs, Terri

[Renee_E]

Fully dressed up when i was 18. I was left at home for the weekend. Bra, panties and my moms shift. I went out for a drive and got stopped. That night I slept in one of my Mom"s nighties. It was full length with a lacy top.

[Danielle Gee]

I was about 6 or 7, and I spotted my sisters lacy long-line bra laying on her bed. Well I didn't know much when I was that age, but I knew I just HAD to try it on. Well naturally i got busted which led to being forced to wear the party dress and Mary Janes!!
I spent a goodly portion of my childhood as a young girl encourged by not only my Sister, but my Mom and Dad too!!

Danielle:heehee:

[Heather_Marie]

I was 18 when I got up the nerve to go and buy and wear my very first pair of panties. It took a litlle longer to buy some cloths but panties was my first and I have never looked back.

[tommi]

my moms nylons at 4 or 5

[Jessica Keys]

While in a small school play that was given to the parents each year for some reason??? I was given the part where I was to change into a girl half way through the play to catch the bad-man. I remember my mom sewing up the fly (LOL) of my briefs so nothing would fall out under the dress I was to wear. I was around nine years old at that time and was already dressing behind my mom and sisters back when they were out of the house. I remember slipping up on the bad guy and whacking him on the head with something soft and he fell down and I straddled him and that was the end of the play with much laughter and applause as the curtain closed.
Little did I know then....Later in the same small school we had to dress-up as the opposite sex entering high school. But that is a whole different story and I was fourteen at that time and knew a lot more about myself??

[Crystal Alberta]

I can remember thinking about crossdressing (mostly just vague, idle notions - nothing really concrete) from the time I was four or five, but it wasn't until I was thirteen that I finally took the plunge. I think one reason I put it off so long is that I somehow knew that once I started, there would be no going back. I was quite scared of that at the time, although it seems silly in retrospect. I was right, though. I never have gone back!

Crystal

[Rachel Morley]

My earliest recollection is of a time when I was 6 and I was playing hide and seek with my best friend Rebecca who lived next door. When we were hiding she insisted she dressed me in her pink cardigan. I can still recall to this day the intense feelings of excitement and fear that I had when she was doing this to me. I think the fear was borne out of doing something (wearing a girl’s cardigan) that was somehow “forbidden” and also the fear of getting caught. We could have been found at any moment. All I know is, that after this event, my desire to want to dress up grew stronger and I started trying on my moms old clothes that were in a box in the bottom of her closet. The rest, as they say, is history :)

[Robyn2006]

It was my sister's 16th birthday, I was 14… off alone at our Disneyland hotel room. Funny now when I look back on that day, it all was so right, such a natural thing really. When the notion struck, there I was within in my mother's bathing suit, stuffed full with toilet paper, and putting on her lipstick. It was a watershed day, completely changing my life forever.

[vickilynn]

I was about 4 or 5, started wearing my cousins dresses

[GaleWarning]

13 years old. Female chorus girl in a Gilbert and Sullivan opera (boys only school).
I remember thinking that the bra I wore felt uncomfortable.
And the make-up was difficult to remove (with cold cream).

Things are different now ...

[ColleenW]

It was about 13 or 14 when I started wearing my sisters panties, garter belt and stockings. After that I'd pinch her bras. I guess I was lucky that we both wore about the same size.:o

[t-girlxsophie]

I was 10yo while staying at my grans house I wore my aunties yellow maxi dress and pink cardigan (no im not colour blind :))dont know why I did it but never looked back since that day

:hugs:Sophie

[tamarav]

At age 3 that I remember, but my sisters used to dress me as their little sister long before that.

[MargaretJ]

About 4.

[shaq91]

My mom's heels in 4th grade!

[linnea]

Seven--I remember it vividly. I put on one of my mother's girdles.

[Paula G]

I was probably around 10 when I found my grandmother's thigh-highs and tried them on, then it was a neighbor's pair of shoes that she threw out. After that it was grandmother's heels and mother's shoes. Didn't try on skirts and hosiery until after I was married, but after that there was no turning back.

[Amy Hepker]

I am very unsure but know I was playing dressup with my sisters and they put a polyester dress on me, it was worn by them years before. I would say I was around 5.

[Nicola2876]

I played dress up with a friend when I wasabout four. Tried on panties at about six and then became a regular tights wearer at ten. Fully dressed soon after and about 27 years later I'm still going strong!

[Bobbi Lynn]

Around 4-5 I started trying on my mothers and grandmothers panties. Still do not have a clue as to "why"?

[Cheryl T]

I was 7 or 8 when I first donned something of my mom's.
I had my first full outfit when I was about 16 and played with makeup at about 18. All those years I could have been perfecting my look and instead hid in my closet. Such a waste...

[suchacutie]

You might not understand, but the answer is 55. Silky black shirt, platforms, stockings, garter skirt. And who did I dress for the first time? My wife! It was the day she exclaimed "we HAVE to buy you a dress!". Did that ever shock me, but it also make something go "click" in my brain. That was the day Tina was born!

tina

[Susan Thomas]

You always hear stories about people being forced to wear feminine clothing, but that is exactly what happened to me. I was about twelve and we were visiting our relatives in Ontario, Canada. One day my aunt decided it would be funny to put one of her padded bras on her nephew. (me!) I can't believe that my parents let my cousins hold me down as they forced the bra on me. It is strange, because years later my aunt actually sent me a picture they took with me wearing the bra. I do look very upset in the picture. Wouldn't you know it, later that summer I started trying on my sisters panties. I wonder if I would have had the inclination to cross-dress if I had not been forced to wear the bra? Later that summer, my mom caught me trying on my sisters swim suit. She yelled at me and asked me if I wanted to be a girl. It is kind of unusual, that I didn't cross-dress again for ten years until I was twenty two. I was quite enchanted with pantyhose. One day as I was getting out of the shower at my in-laws house, I noticed my mother-in-laws pantyhose hanging on the towel rack. I couldn't resist and slipped on the pantyhose and have cross-dressed to this very day!

[StaceyJane]

I think I was 12. I put on my mom's pantyhose for the first time. Soon I was secretly wearing her dresses and putting on an old wig she had.

[Diane Smith]

My mom used to put lipstick and nail polish on me occasionally when I was as young as three, but that doesn't really count because I didn't initiate it at that age. My early memories are rather fuzzy and full of gaps, but I know I was trying on her heels, stockings and girdles by the time I was 5. I didn't get beyond the lingerie and into outer clothes until my teens, but that was mainly because I had no access to anything that would fit until then.

- Diane

[Samantha43]

12 or 13. That was 35 years ago. Been hooked ever since!

[nikkijo]

3 as far as i can remember. but at time it was more of a practical problem than me causing trouble.... my younger cousin(by a month) got car sick and threw up all over everyone in the car, and the only clothes clean in the vehicle was hers, we spent an hr at the road side creek washing everything but still needed something to wear in the interm

a pair of osh kosh over alls...

[Christina89]

i was 12 years old when i first stated and i have been hooked ever since then.

[happy2cd]

I was in kindergarten and tried on a wedding dress that was in my sisters' dress up box. I later wore one of my sister's underwear to school and got caught. At the same time I used to go to my Grandmother's apartment for nap time with my little brother. My Grandmother used to put a full slip over me for a sheet. Before to long I got up and tried it on in the bathroom---slips are still my favorite article of femme clothing.

I stopped for a while but would sneak a nightgown or bathingsuit once in a while. When I was teenager I couldn't stay out of my mother's and sisters' closets and underwear drawers.

Now I have way more clothes than my wife and I am far more interested in slips, nightgowns, dresses, etc. She prefers pants and shirts and I prefer frilly, silky, lacy things. She wants me to purge and give it up, but I have told her that I can't so I keep my things in a storage unit and wear them when I can...like Halloween.

[ANA LILIA]

at 10 years, I found clothes my aunt.

[noeleena]

Hi.

I was dressed as a girl for our end of year do a pantomime for our chuch in front of about 80 to 100 people & my Mum was there as well all dressed up clothes make & all & on stage , age 10 - 11 in 1958 -9, Mum was not bothered & it was fun , the fore runner to what i am now no i cant say that tho i knew i had a female side ,

...noeleena...

[Claire Cook]

I was 4 or 5 when my mom let me play "dress-up" in a dress and it just felt so right. After that I would get into her closet whenever I could.

[SusieB]

At seven or eight I played dress up with my next door neighbour. I tried on all her cloths and was instantly hooked. This continued for about two years. Everytime she got a new dress she would let me try it on. Finally goy busted by her mother and that was the end of that. I dont think she told my parents because it was never mentioned. I have no sisters so opportunities rarely presented again until I left home.

[Alisa]

I started dressing at a young age. My best friend's mother and sister would often dress him and compliment him on how pretty he was, etc. At around ten years old, made me curious enough, to try on some of my mothers clothing. Started with pantyhose and soon added a full slip, mini dress, heels and a wig. Even ventured out for a stroll around the neighborhood after dark.

[ILV2DRESS]

I was around 6 or 7 I used to wear my sister pantyhose boy over my regular underwear (yuck) .. I loved them and to this day that is my favorite.. I also love an silky lingerie and dresses..I used to dress in their stuff when ever i could.. I still remember the first time I wore a pair of panties and pantyhose with out anything underneath it I was like 7 or 8 talk about heaven.. still to this day i love putting on a nice little thong and pantyhose..

[Melody Phillips]

I was in my early teens. It started out with bras, underwear and nightgowns. I fell in love then and there with the feeling of womens fabrics and clothing.

[missjoann49]

For me I started at an early age of 3 or 4. It was my moms doing, I was an only child, and she had wanted a girl instead of a boy. My dad used to work alot if nights so whenever he wasn'y home my mom would dress me as a girl..this went on until I was in the 8th grade..in some ways I wish she had never stopped dressing me, now I do it when ever I can, but not near family
as they wouldn't understand. Last weekend I took some time for myself and went up to Wells Maine, I will post something on this later, but it was a wonderful weekend for me..I became the woman of my dreams for the entire weekend

[Cindia]

I remember staying home sick from school in the third grade by my self for the first time ever and spending the day in moms bra and pantyhose and sisters skirts and shoes. I know I would try on their panties any chance I got before that and recall being jealous of my sister wearing a type of body suit that I couldn't. That would have been at 4 or 5, but I honestly don't remember the first time I tried on my sisters underwear.

[Annette_boy]

It was age 5 tried on Moms Panties loved it been hooked ever after. That was 60 years ago, I now dress 24/7

Hugs Annette

[MaryAnn40c]

Lets see I was 8 years old and at home...the first time I was out I was in grade 7 and was in a dress,bra,undies,nylons....it was a guys dress as girls and girls dress like guys....the whole school(7-9) did this. Hmmm so much fun.

[Stephanie47]

I was less than ten! My mother use to hang her hand washed slips in the only bathroom. Early on I would try them on still wet, but, the feel of dried slips probably turned me into loving sensuous fabrics. Later I found she stored some of her dresses in the closet of my bedroom. They were truly of the 1950's- form fitting at the bodice with a flared skirt and side zipper. I loved squeezing into those dresses with a slip, bra and girdle and stocking. However, she had the ugliest panties.

[crashd0309]

I think I was 8 or 9...whenever my mom/dad started letting me stay at home alone. I loved the feel of my mom's slip and panties so I tried them on. Soon I was trying on her nylons and bra. I did it for about 2 years until I got caught. I was so ashamed I didn't start again until age 41, about 2 months ago.

[Margaret]

My earliest memory is trying on a slip of the daughter of friends of my parents. I was four years old. When I was seven, I was loaned a girl's swim suit to wear at Balmoral Beach (Sydney). The day was hot and I had not come to the beach with any swim wear.
Many years later (over 40), the lady who gave me the swim suit reminded me of the occasion in front of many friends and family. I was mortified.
I discovered my mother's all-in-one open bottom girdle when around 13 years old: the first time I was home alone while mom and dad went out. I don't think they ever knew. I still love all-in-ones 43 years later!

[AKAMichelle]

at age 5 in kindergarten I use to play dress up with the girls

[sonna]

4 or 5 sisters pantyhose

[Lorna]

Simple answer: 13.

Even at that age my mother's clothes (I had no sisters) were rather loose on me. I am intrigued by the several contributors who wore their mothers' things when only five or even younger. At five I could have got most of my body into just one of my mother's stockings and her girdles and bras would have gone round me twice - and my mother was a slim woman. Perhaps, when they say they "wore" them they really mean something rather less than that.

[Tasha McIntyre]

I was 11 or 12 when I first tried on my mothers clothes which were quite awful to look at, but felt great th wear. I was 16 when I bought my first skirt of my own :)

[Leanne2]

Well, not exactly womens clothes, but around age four I put on my cousins party dress. It was intended to be a hand me down to my little sister but I kept it as mine for years until it fell apart.

[Tomara]

I was six years old the first time I put on one of my older sisters bras , I loved the way it felt on me that day and I still love the way they feel on me today !

[ringedjohn]

I only like under-dressing. I tried on one of my Mom's girdles at around 12. I bought my first pantie girdle soon after - and have never stopped.

[SusanLCD]

Probably around 11 or 12 yo. I don't recall a specific instance. Only that I was able to sneak into my mom's (and others') things, infrequently. The dishonesty of it bothers me to this day.

During my married years, i largely suppressed it in favor of the relationship. It would erupt periodically, but, mostly I kept it locked away. Back then, being out en femme could have resulted in arrest and social stigma, which was a deterrent to letting anyone know. (I have no nostalgia for that type of restrictive social structure.)

The first time I owned my own clothing was only a few short months ago. How liberating!

[Jilmac]

I know I shouldn't get so technical but I didn't start wearing women's clothes until I was about 16 and I had three older sisters who were into womens sizes. All right, I'll come clean and admit that I started at around age 7 when cousin dared me to wear panties and a dress. Of course, they were technically girls clothes. I experimented with female clothes (girls' and womens' sizes) until age 16 when I dressed fully in my adult sister's panties, bra, girdle, nylons, slip and dress.

[Enrico]

I must have been around 12 years old at a friend's house. His mum had a box full of clothes, including short skirts, heeled boots, stockings and so on. Whilst we were alone at his house, we decided to dress up as women. The feel of nylon and heels was great, the short skirt revealing my thingy before the friend was awesome. We did many sessions after that one. Still dressing in heels, stockings and short skirts 34 years later.

[elsbethcollins]

i started at 12 with my sisters tights - kept on this way (along with bras dresses etc) until I had the house to myself one weekend, maybe 17 or 18 and dressed completely and tried makeup for the first time

been hooked on the whole thing ever since

[Margo Paulse]

I started at age 4. Tried on my mom's girdle. I also had a homemade stuffed cat -it was stuffed with old pantyhose:)

[Jay Cee]

Sometime around puberty for me. I think I was 13 or 14 years old.

[Leesa2]

I was five, a girl my age that my mother used to babysit wanted to trade clothes. We hid in the corner of my living room behind our black vinyl lazy boy and exchanged clothes. I still remember that she wore satin panties that day! It was absolutely wonderful and we did it a couple of times after that...

[scpantyhose]

I was 5 I think. Before kindergarten. An aunt's panty girdle. I was in her bedroom and saw them on a chair. For what ever reason, I put them on and played at being two different people (with and without the girdle).

[dylan136]

I think i was around sevenish i can barely remember it though

[Ria]

I must have been around 5 yrs old, My mom's pantyhose felt so good to me. I was compeled to put them on for some reason? I loved them.

[Kate Jennings]

I was about five when I went into an old dresser and hit the motherlode! I distinctly remember putting on a bra, girdle and throwing a fur stole over my shoulders while I pranced around the room. Years later it was lipstick, Mom's wig, heels and the rest is history.

[PippaJ]

I remember playing dress up with my nan when i was really young, I'd play with her earrings (because she had lots of clip on ones) & walk round in my mums heels; I remember trying on one of my mums dresses when i was about 6 or 7 as well.
as for actually dressing it was one year ago on sunday :D lol

[Collins]

I was about 7 when I found some of my sisters silky underwear, I loved wearing that, then I was hooked, I went out dressed for the first time when I was about 15.
Now I'm married with a 16 year old daughter and I still love dressing up.
My family don't know about my fetish, but I love wearing my daughters school uniform and other clothes.

[paulaluvssz8]

I can't remember how old I was. I do remember as I got into my teen years it got stronger and I would go into my moms room or my aunts room and borrow their panties. And the story goes on still today. Except I buy my own panties and things now.

[NikiMichelle]

I was about 5 when I first started to wear my sisters tights...why I started I have no idea but here I am now a 50+ full fledged CD with a wife of 30+years who has known for over 10 years.

[KellyCD]

I was 7 years old, and started with some of my older sisters panties. I'm 27 now.....it's surreal to think I've been dressing for 20 years....

[Jenny Gurl]

I can remember wanting to be a girl in Kindergarten, and trying on moms things. I asked my mother once when I was that curious and naive age why men don't wear pantyhose. Her reply was "they gave them a chance once but they didn't want to do it" I remember my mom had stored a lot of older cloths she and my sister could not wear anymore in the attic. Dresses, swim suites, pantyhose, bra's, etc. She also had some older lipstick that I can still remember the smell of when I wore it late at night. I remember wearing the pantyhose underneath the one piece swimsuit, all underneath sweats, socks, and a shirt. Wake up early for school and take it off. I was always jealous of the girls at school because they got to play with fashion, makeup, nails, shoes, etc. You can say I started early, and reconfirmed my crossdressing attraction consistently throughout my life. I probably will outgrow the urge when they close the lid on the casket. Of course that is when I will be reincarnated into a man in a woman's body. :heehee:

[Hayley Comets]

I was probably 11 in primary school. I had forgotten to bring my gym kit, I really wanted to join in the game so a girl who was excused offered hers to me. The boys gym kit had blue shorts and a grey t shirt, the girls gym kit was a white tank top with red running shorts (they were basically shorter). Running around in that felt really good. Of course the boys were jerks and called me names but the girls were more than happy to welcome me to their team.

I bought my own girls kit and wore it several times to class before the coach made a big deal about it. Hit some bumps but you could say I never looked back since then.

[brandi.tgurl]

I used to play dress up with my sister. I think as early as 5 or 6. However, I didn't realize how much a part of me it was until late in high school when I began dressing again.

[Crysten]

At age 3 that I remember, but my sisters used to dress me as their little sister long before that.

Also around three....and I was definitely too young to know there was anything "wrong" with it...since I came down the stairs all dressed up in a dress and heels into a family gathering!! My mom had pictures of this event for the longest time, don't know what ever happened to them though.

[kimdl93]

probably about 5...I can still remember finding my sisters slip in the laundry...slipping it on and the thrill and embarrassment of that moment. Even then, I'd a perception that what I was doing was somehow forbidden.

[Empira]

I don't remember exactly, when I actually wore my mother's pink tights but I was about six or seven. I had been fascinated with dancewear for several years prior to that. The Sears catalog was an obsessive focus for me during that time.

Empira

[Warcraft_Girl]

I was young enough that I didn't know what I was doing. All I knew was that I liked the feeling of soft and silky things on my skin.

[joanna marie]

I was around 8 when I started wearing my sisters clothing
really enjoyed her catholic grade school uniform,dark blue jumper,white blouse with peter pan collar ,and saddle shoes

[AvidFan]

I wore my sisters bathing suit to be funny when I was 6. It was really to be funny. My mom told me my junk would shrivel up and fall off like a raisin. Scarred the hell out of me. Didn't do it again till my early 20s

[Jordan]

I was about 10 when i started to womens clothes. I took stuff one time from hudsons department store to have my own my mom found them a while later I never had to explain it they blamed somebody else what a dispointment I lost all my clothes but now I have plenty

[Jaydee]

At age 10 I was going to be taking ski lessons. My mom obtained a pair of black tights from a friend's daughter. I didn't like the idea at first, but soon loved them. A couple years later I found some discarded pantyhose in a spare bedroom. It took off from there.

Jaydee

[Charise52]

I was about six... I wanted a cowboy outfit and my mom, probably for economic reasons got me a cowgirl outfit... skirt, vest, hat, gloves and a cap gun in a holster... I wore that skirt everywhere for almost a year before the first grade... then I was hooked...

[KylieQ]

I can remember sneaking into mom's closet as early as age 6 to try on her dance gear. It was when I was 10, though, that I first really dressed. We moved into a new house and for some reason my mom decided to store a bunch of dresses and shoes in my closet. I was in absolute heaven!!! We lived there for about 4 years and the dresses were there the whole time (and got worn quite often by me).

[Tbirdgal]

Uh 4 or 5 , I'll be sixty this year and I'm full time now .

[KarenEdwards]

I was around 4 or 5 years old. For some reason, I decided to try on a pair of my mother's panties. It just kinda grew from there and I bought my own lingerie at 14 from money I made mowing grass for neighbors.

[PattiMichaels]

I was 4 years old when I first dressed, and I VIVIDLY remember INSISTING that my grandmother let me wear a pair of her pantyhose. My mom and her carpool girlfriends all had a good laugh at my expense when they picked me up that night.

Fast forward to my early teens when my mom started working days and afternoons. I started off with her pantyhose this time, and later discovered her lingerie drawer. Of course I discovered her make-up drawer, and I actually remember painting my toenails one afternoon as well. By this time, we were perfect size matches (and remained so for 3-4 years!) and I very quickly progressed to entire outfits, down to shoes and accessories.

I first went out fully dressed when I was 17. I made-up a story about going to a costume party and had a full make-over and hair styling at a salon downtown. I even gave myself a pedicure and false-nail manicure. All I did was wander around downtown on a Friday afternoon as Patti. Thank goodness for mom's dna and wardrobe!

[Amy S]

I don't remember the exact moment myself, but it had to be 6 or 7. I remember always running up to my sister's room when they were gone and trying on their clothes.. Must have done this until I was about 16. Now I can buy my own :-)

[Janet Bern]

I think I was about 8 or 9 when I started wearing my aunts things.

[Marla]

I was about 7 and I put on my moms lipstick. Wow! Im sure she wondered why she had to keep buying new lipstick. When I got old enough I started buying my own and have never stopped. I was married to a beautician and loved every minute of it until she realized that I was wearing her make up and wigs and divorced me. Oh well some people dont have a sense of humor or any sense at all.

[Tasha2633]

I was home alone around 12 and i was drawn to lingerie. had to put it on.

[barbara f.]

I was about 12. tried on my some of my sister clothes and the feeling of them on me felt pleasurable. suppressed my dressing for fear of getting caught and wearing my sisters clothes. thank god for the internet it is easy to buy clothes.

[tgcowgirl]

I don't ever remember not wanting to be a girl...to wear what I saw other girls wearing. I was 6 or 7 when I actually got to wear a dress for the first time.

[maggi]

about 10 or 11 years old i always liked to put on my sisters gymnastic suits or my moms underwear

[danielletorresani]

I was probably 13 or so when I first tried a dress on. I didn't really start CD'ing until I was probably 15 or so.

[JESSICA 003]

I was about 5, got caught in my mums slip.

[Zoie]

I was young so i cant really pin point it but id say kindergarten timeframe.. didnt know what I was doing really seemed natural.. thats why id like to have a test to see what my sex chromosome really are!

[Didi]

I was about 8 or 9, I wore my sister's girdle and stockings.

[Kerrie Sifton]

I was around 10 and found one of my moms dresses, black satin and lace, like my avatars, in a box in the basement. I had a girlfriend come over and we dressed up, at which point i did not want to undress. It was a lovely sensation.
Today I still remember that dress, and am on the look for a replacement....

[clairebostock]

Depends on how you class when you started me i was 8 and i wore a girl's school dress.
properly i was dressing when i was 22. started with mum's clothes (like us all at one time or another ) till i could buy my own.

[aya-chan]

I was about 7ish when I tried one of my mam's skirts for the first time. Obviously I had to hold it up with a hand as it was a bit big lol. First time full outfit and make-up was 13 I think.

I've just started buying clothes of my own now, which eliminates all the sneaking around I used to do lol

[Julie S]

I was about 4 or 5 when I persuaded my mum to let me wear her tights. I've never looked back.

[ShelleyTVUK]

I was about 4 or 5 when I remember taking my mum's bra and slip into the toilet to try them on. No idea why, seems like such a young age to be doing something like that. It wasn't until I was 13 or 14 when I started dressing more fully. I used to wear my sisters dresses and jewelery. It was a good age then because everything fitted!

[linda1977]

My first crossdressing experience was when I was 6, although I always had the urge to wear female clothes before then. This happened during a Xmas panto performance/rehersals in my infant school, where my friend and I took on the roles of "Kings of Topsy-Turvey Land" in Sleeping Beauty. We were "topsy-turvey" because the top half of our clothes were masculine, but we both wore a mini-skirt and pantyhose below! Looking back, I should have been embarassed about that cruel joke put upon by our teacher, but I wasn't. In fact, I was SO pleased that I was given the opportunity.

It was when I reached the age of 11 that I finally had the courage to fully cross-dress, and have continued to do so for 22 years and counting.

[Cassiecd]

I guess this is where I stand out from the crowd:

I started at age 50

I stumbled into cross dressing accidentally, a game of sorts with my wife. ZOWIE! What on earth was I waiting for? I am definitely hooked, but she no longer participates.

[kristinacd55]

Well first I started with girls clothes, since i was 6 or 7 :) Women's clothes came when I got to be a woman's age.......18? 19? :)

[CindyT]

It was at about 5 or 6 for me. Mom's girdles and nightgowns, I always liked that silky feel! I was hooked right away!!! When got to be about 17 or 18 I finally got the courage to buy some womens clothing, mostly undies and pantyhose.

[juligirl1984]

I dressed first when I was in 2nd grade. I just moved back to the east coast and was home babysitting my sister after school. Mom was not home so Id put on her bra and do chores with it on. then I tried panties and a bra. after that it kept going to anything she had. I never stopped, I was caught once in my sisters dancing tutu lol! and in my moms bathing suit when I was 14. I was never caught by my mom, just she would find her clothes in my room.(oops!!! LOL!) so maybe she kinda knows?

[Terry V]

I have replyed to this thread before but I was about 9 or 10 and my aunt caught me trying on my cousins panties and wanted to know if I wanted to be dressed as a girl when I said yes she dressed me in her friends little girls Easter outfit and I loved it with a frilly yellow dress and petticoat underneath I always had the desire but when I had that dress on it was more than I could understand but all these years later I thank my aunt for showing me this world I live in and shared with her for many years after.

[gaylegirlify]

I guess i was around 15 trying on knickers and bras, crossing my legs pretending to be a girl, i new i was a girl right there and then.

[DKA]

My first time I was around the age of 7 or 8 - maybe sooner but, thats the earliest I can remember - I know I loved the feel from then on. they were my older sisters and my friend dared me 2do it, I was apprehensive at first then I loved it!

[katrinakat]

me too!!!! all day while my mom worked!
I remember staying home sick from school in the third grade by my self for the first time ever and spending the day in moms bra and pantyhose and sisters skirts and shoes. I know I would try on their panties any chance I got before that and recall being jealous of my sister wearing a type of body suit that I couldn't. That would have been at 4 or 5, but I honestly don't remember the first time I tried on my sisters underwear.

[Tallulah Rose]

I think it's interesting that so many of us started dressing so early on in life. I was about 5 years of age and I was drawn to my mothers high heeled shoes (which were far too big). Then came the stockings. That was the "slippery slope" for me. ;)

[Rebecca Sue]

I grew up in a house with a lot of women and was always slipping into feminine things.

[juligirl1984]

I started at age 7 or 8. I think. I do know it was after parents separated. Maybe what triggered it. I always got yelled at earlier than 7 for touching my moms legs when she wore hose. I do remember that clearly lol!

[Tammy V]

I was probably 6 or 7 at the oldest. I was either 8 or 9 when at my grandmother's house I put on one of her wigs, a dress and some of her shoes and jewelry and walked out in front of her and her sisters. They all got a big kick out of me, but when my garandad came home he was not amused and it was off with everything.

[crashd0309]

I was about 8. I loved the silky feel of my mom's nightgowns. Soon I wore everything of my mom's. I sort of got caught when i was around 10. Mom found some of her clothes scattered about when she came home and she confronted me about them. I was so embarrassed I never did it again....until a few months ago when my wife was behind on laundry and I put on a pair of her panties as a joke. I've been hooked since!! :)

[Kaz]

10 - 11? That era...

[Billie Jo]

I was probably about 5or6 I only had girls to play with so we dressed up and they dressed me up and their I went

[GeorgieMacD]

My mother came from a family line that dressed all their young children in dresses until about 2 years old. I guess that was a passive start. My first memory of actively trying on clothes was a few years later. My mother always walked around the house wearing bra, girdle and stockings and sometimes a full slip. I remember my fascination with the soft clothes and was always nearby when she dressed. She would let me play with her soft clothes and regularly helped me play dress up. It was certainly the defining time for a lifetime of dressing up. I remember vividly being 10 and in fourth grade when my mother wore her first pair of tights. I just had to have some of my own. She got them for me and they became the first item that was exclusively mine. She added to my collection regularly over the years until I started buying my own soft clothes.

I plainly remember my father's negative reaction to all that and my mother's whispers to him that it was all right. Ironically I found out some time later that my father was a cross dresser. It explained a lot about Halloween and other memories.

[juligirl1984]

lol wow go figure, you dad was a cross dresser and got mad that you were one! maybe he didnt want you to go thru the ??? that he did. that was nice of your mom to support you.

[WheatishCD]

Hi juli, nice topic.
i still remember when i was in in 5th grade i saw my mom all dressed up. she looked so stunning. the moment she went out i just raided her wardrobe. since then it is no looking back.
luv
reni

[latexlover]

I was 15 when I started to crossdress. I had between 10 - 12 pairs of shoes and 3 outlets, but some years later my mom look thru my closet and found the shoes hiding and got in trouble , but later down the road at 21 i was married and back crossdressing when the wife wasn't home and still til today i'm still crossdresser but with a little time to dressed up

[Karen kc]

I was 6y.o. and on a cold January evening the old floor furnace quit,in order to keep me from freezing, mom made me wear a pair of her bright red tights. Wasn't long after that, my oldest brother caught me putting on lipstick! The rest is history!!!!

[Ellenor]

Around age of 10. I had no sisters and was part of a very male dominated house so any weakness was not permitted. Anyway I was a paperboy - humm - paperperson? anyway and saw a customer's bra hanging on the clothesline - well it came home with me. Then came the bathing suits, on clothes lines of course. Then the bras in grocery stores -- easy to take. Not making any excuses - just telling it as it was for me.

[Donna June]

Around 7 or 8. I was lucky in that I had a sister two years older than me who was cute and feminine. Years later when she went off to college, but half of her clothes were still home, I had the time of my life

[CallMeEmily]

currently the story of my life lol.

[Lynn Pennington]

I was fasinated with ads showing womans cloths when I was about 4 or 5,and started dressing whenI was 12. I had a big family besides my mom I had 3 sisters,and always waited till a some cloths piled up in the bathroom,then I would take time with my shower .Trying on things.I loved wearing nylons a girdle and bra stuffed with socks. It was such a sexual turn on.Now I enjoy dressing,and looking and feeling sexy. I can get the turned on feeling if I want to,but rather sit around dressed,and admire myself.

Carolyn

[Dawna Ellen Bays]

Wow! I thought I had replied to this thread already. I couldn't have been more than four or five, and I demanded that I get lipstick out on me because my sisters were getting it, too. Around the same time, my aunt had a pair of boots that I thought were really awesome, and I would sneak into them whenever I got the chance. It only dawned on me the other day that stepping into those seemingly gigantic boots gave me a tingly feeling inside. I experimented with makeup for the first time around 14 or 15. I put on everything but foundation. I didn't clean off the mascara very well, and a friend of mine almost busted me: "Why are you wearing Egyptian eye makeup?" It wasn't until I turned 18 that I realized I was a CD/TV...

[Carmon]

Ten, I remember putting on my mom's slip, nylons, girdle and one of her dresses being stored in the attic. What a wonderful memory! I've been hooked on dressing ever since.

[Madilyn A.]

I was in the 4 to 5 yrs.old range with shoes and stockings and lipstick. I know by 3rd grade I was well into complete lingerie and dresses, garterbelts, stockings and makeup. How I wish I had continued my feminine ways at that early pace.

[CDSamantha]

I was 8 when I tried my mother's slip on. The feeling of the satin and the look of the lace hooked me for life.

[jasmine57]

I was about 12 or 13 when I first tried mom's pantyhose and girdle. And like so many others haven't looked back.

[Xandria]

i remember sitting in a highchair while my mom painted my toe nails and finger nails, then, and i'm not sure if this was before or after the mentioned memory that she put makeup on me as well. yeah.. she wanted a girl pretty bad me thinks

[paulaloha]

I was 4 or 5...

I remember it was a blue sparkly leotard that my little sister had, I just remember that I always wanted to try it on, so I did. I have dressed in my sisters clothing on and off ever since.

[Dana]

I was around 11 or 12 when I started raiding my sisters lingere?

Even as a little tyke ~ feminity always allured me.

In my obsolescence? My sister moving back in with me and my Dad re-awakened my interest in such?

Until it lay dormaint.

At first I rationalize it as trying to understand girls and women ~ which was total and complete BS!

Later I joined the Marines and then marriage.

I tried another long term relationship in which she told me I was "part girl"

This was on the dawn of the internet per say, but just her saying that excited me mentally, pyschologically, emotionally and yes even sexually to no end!

Back in 'tha day' I didn't know where all of this would lead?

But now "Back in the Future" I would love to be the "wife" of some GG.

I know that's never going to happen!

[nicole12]

I was around 11 or 12 when I started raiding my sisters lingere?

Even as a little tyke ~ feminity always allured me.

In my obsolescence? My sister moving back in with me and my Dad re-awakened my interest in such?

Until it lay dormaint.

At first I rationalize it as trying to understand girls and women ~ which was total and complete BS!

Later I joined the Marines and then marriage.

I tried another long term relationship in which she told me I was "part girl"

This was on the dawn of the internet per say, but just her saying that excited me mentally, pyschologically, emotionally and yes even sexually to no end!

Back in 'tha day' I didn't know where all of this would lead?

But now "Back in the Future" I would love to be the "wife" of some GG.

I know that's never going to happen!

I was 14, i remember the day well , had day off school and tried on my sisters make up and clothes and was so very very exciting.
Through my teens i dont remember other than that day dressing until 18 years of age when i was overseas of a year.

Through my early twenties i dressed on and off i remember going to business here that did transformations.

Then i worked overseas for a while from 27 onwards and dated for 3 years and can remember only dressing on the one occassion then.

Come back home in my early 30's started dressing again and been on and off since, last gap has been 12 months i guess and only started again last week and alot of my desires have also changed etc.

[Lexine]

Not more than two years old. Honest!

[Nicole Anne]

I was just talking to my mom about this at Thanksgiving. I asked her how old i was when i was seen wearing something of hers. She just laughed and said she remembers once when i was about 5, she called me to get ready for dinner. Well when i came to the table i had put lipstick on myself. She then said it became a regular thing after that. Yes she was very supportive. "Love ya Mom"

[Sally1983]

I was 12 and I dressed in my older sisters clothes. She found out after not long of course, and she wasn't really happy about it. She ended up giving me a skirt,a dress and a top that she didn't want anymore on the condition I didn't raid her wardrobe anymore.

Gotta be happy with that :)

[Davina99]

Sister's silky panties at about 6 or 7. Graduated to her bras and tights a few years later. Fully dressed at about 14. Then she got married and left home. Took a few years to get up the nerve to get my own gear after that.

[Carly D]

Preschool somewhere/sometime.. Me and my older brother would play "Charlie dress up" and I always gravitated to moms clothes..

[SallyS]

Not knowing what it was all about I'd say six years old....mums slip I think?
Knowing what it was I was doing.....my teens....sisters and mums stuff!

[Lexine]

Hi Lexine! I like your outfit and you look pretty! :)

Thanks! You should see the picture thread I posted! It has more :D

[TracyBoy]

When I was about 10. My friend and I found my Mom's bra and other clothing. I put it on and pretended I was a girl and kissed my friend. I've liked it ever since!

[stellatoo]

I was about 10 or 11 and it was my sister's panties! Once during a biology class I asked the teacher what a boy wearing women's clothes was called! Then I had a name for my "hobby". There was also a group of about 25 teenage boys staring at with with a "WTF" expression on their faces! I don't remember anyone saying anything though...

[Jessica S]

I was 5 yrs. old. I was helping sort the dryed laundry and had for my moms kneehi's ask what are these and then just put them on. the felt great. It didn't take long to look for them again and found pantyhose. My mom kept a bag of old pantyhose in a closet right across from the bathroom I raided all the time. The of course the silky slips and panites that hung to dry in the bathroom I tryed on next. Everything was big but I grew into her tuff between 10-13 yrs old. When I 12-18 yrs old and left at home alone I wore her clothes that I could fit into.

[jamey]

I was three. My mother thought it was cute at first. Then I would get in trouble for wearing my female cousin's shoes so I learned to hide it!

[TianaCross]

really young, probably about 3 or 4 when i first tried my sisters clothes... theres just nothing that would sexualy arrouse a child at that age... but it did feel great..and as i see, many CDs started at that age.. kinda gives u something to thing about...as i continued quite regulary to dress from then on when i get the chace.. but hey, im one of those people who think that the idea of reincarnation is not that crazy ;)

[VanessaVW]

I was 4 or 5. My grandma dressed me up in panties and a slip. It was way too big, but it made a lasting impression.

[Michelle 2774]

I remember that I had seen the Wizard of Oz the day before, and wanted to recreate it in my childlike fantasy...my sister became the Scarecrow, and my other two boyhood friends became the Tin Man and the Lion and of course, that left me to be Dorothy which I had wanted since it was my idea! I had a basket and when we all came in for lunch, I asked my mother to lend me my sister's dress so we could finish playing.

My mother thought it was cute so she gave it to me!! I had a much longer discussion with her several years later about this incident but that was my first time. I was six or seven at the time......

[avalana]

i guess i started out as a little girl at age 3. grew into bigger and better things a i grew older what with 3 sisters and a bunch of girl cousins who all wanted neices! first was panties and cute little dresses. pantyhose,slips and bras around 11 or so they felt so good under the dresses it was hard to breathe sometimes! hardly ever wore guys undies in over 50 yrs. certainly never bought any......

[charlytuna]

only childhood I can remimber with women clothes I was around 12 when started going through the dirty clothes in the bathroom when I took baths and trying on my mom & sister clothes mostly bras & panties then when home alone go through their closet & trying on dresses. Got caught once by my sister [that I can rember] in the bathroom with her bra & panties on. she just scream at me & left not another word was said that was back in the 50's I often wonder if she ever think about that day I do

[Davina-Alba]

I think I probably wore girls knickers from a very young age. I was an only child but I had a lot of female cousins. Back then (the 1950's) attitudes to childred of both sexes bathing together or sleeping together were very relaxed so from an early age I knew that I looked different from girls "down there". One of my aunts had 5 daughters and no sons and the girls were intrugued by my "extra bit" which we soon discovered got stiff if you played with it.

Anyway, I often slept over at my aunts and remember being given girls pants to wear if mine were not fresh and even slept in nylon nighties if I'd not brought pyamas. This happened quite regularly as my father was very ill and ended up in hospital without warning. When that happened I'd be picked up from school by a cousin and so didn't have overnight things. Of course my mother could have left stuff there but the fact was that no-one thought there was anything wrong with a boy wearing girls things.

The first time that I wore female attire and realised the sexual connotations was when I was about 8 or 9. There was a fancy dress party of some sort and as money was tight the decision was taken that the cousing of about my age would go as "Tommy Tucker" a children's character of the time ("Little Tommy Tucker sang for his supper - if you remember the nursery ryme). This was her wearing my school uniform, shorts, shirt, tie, cap etc and carrying a football. I was to go as a St Trinian's Schoolgirl. As I was much taller than my cousin I wore her older sisters school uniform complete with suspender belt and stockings (and carrying a hockey stick). My "extra bit" was very happy with this so much so that two of my cousins had to help me get it limp again.

The rest, as they say, is history!

[Britney Styles]

I was in early puberty when i started wearing pantyhose and womens underwear. I had a fascination with pantyhose since I was a small child. Later in high school I put on an ex girlfriends work outfit, black skirt, white top, black sweater, wedge heels, and pantyhose. This was my first experience cross dressing. Later in college I started buying clothes and shoes that properly fit. I recently just bought a wig. I hope to go out in public someday.

[Kelly_on_platforms]

I think i was about 6...but can't tell for sure. My mother always kept lots of clothing for my cousins at home....and I knew where she kept them. It was a little girly sundress for me the first time. I also remember wearing my cousins summer sandals, but they were a little big on me at the time, but i still enjoyed it a lot. Back then I spent as much time dressed as I could. My parents worked long hours when I was young.

[Jill M]

I think I was about 13. Started wearing my sister's panties, skirt, and silky top. Loved the feeling.

[AmberM]

I was thirteen wearing my mom's white bra/panty set with a little black dress. It felt good, and sexy.

[Julieanne]

Oh my -- the older I get the farther away it becomes. As far as I can remember I've always been a crossdresser. I cannot remember when I was not, so I guess that puts it at 6 or 7? 10 or 11? Either way I've been crossdressing for 5 decades or so.

[Alberta Daisy]

22 years old. My then girlfriend and I had plans for new Years Eve, and I was grousing about the time she was taking getting ready. She said something about if I thought it was so easy, maybe I should try it myself. Being well primed on booze already, I called her on it... Needless to say, plans were aborted, two hours later I was fully decked out from head to foot in matching bra, panties and garter belt, cocktail dress, nylons, strappy heels that her Amazon roommate left unsecured, and a HUGE updone wig. Best New Years ever, and Daisy was born.

[Lilaka Ananda]

I was 18, staying in my girlfriend's stepmother's ski cabin the year I lived as a ski bum. My landlady kept a wardrobe there of various items, and one night, on a whim, I tried on some pantyhose and lipstick. A star (in her own mind) was born that night.

[Avana]

5

wearing my moms clothes and playing house with the neighborhood girls. i used to always play the baby daughter.

[Jaclyn NM]

Probably about six or seven, when I first tried on my mom's high heels, and then her stockings, which really turned me on and started me on to becoming the crossdresser that I am today. And I can honestly say that I have no regrets. I love who I am, and I love wearing my female clothing, especially stockings, and really high heels.

[Rilulia]

If I remember correctly, I believe I was about 7. I just tried wearing my older cousin's clothing just because they were laying around. I have to say, girl's clothing feels so much softer than boys.

[Janine G]

I was 8 my mom (single mother) had me stay with my aunt for a week while she was caring for my grandmother. I didn't have any pajamas, so my aunt dressed me in my cousin's. I remember them like it was yesterday, they were like a yellow camisole and tap pants. I remember lying on the floor watching TV before bed with my cousin enjoying the feel of the satin on my skin. That same week I started to "borrow" my cousins panties.

[drjoancds]

At the age of 8 y.o. or thereabouts: I grew increasingly curious and tried on her panties and nylons and clopped around on her still-too-large heels and she thought it was hilarious and saw no harm, I was still a boy, riding my bike, playing rough with my siblings, catching worms and fishing. My dad took me hunting, I was in the Boy Scouts. At 12 y.o. I was an altar boy in the small town's Catholic church and I LOVED the cassock and surplice I wore serving the priest during Holy Mass; it made me feel angelic, feminine, and yes, it was pretty much a dress, for all intents and purposes. Then I was into mom's or my three aunt's lingerie/nylons drawers and perfumed church-going black kid leather gloves whenever I could 'visit' them clandestinely....and intimately.

The rest is, as they say, 'Herstory'...[/QUOTE]

[drjoancds]

I too was an altar-boy during my formative and exploratory years, and until I read it here I thought I was the only one who ever fantasized that my cassock and surplice was a dress.

[drjoancds]

My first memory of interest in wearing womens clothing was one summer age 6 or 7, alone in the basement family room, playing, and finding a clean laundry basket. I discovered the proverbal mother load of her lingerie, slips, panties, bras, girdles with garters, nylons with seams. I had watched my mother dress before for dinner and dates out with my father. "Lorna" is right, wearing might not be the right description at that age, but for some time I was mom and getting ready to go out. The clothes litterally draped off my body, but in my mind they fit and looked good, especially when padded with couch throw pillows, and lord knows how i ever managed to not ladder her stockings.
I never had a sister, and no female relatives who lived close. It wasn't until 2 yrs later wher we lived in another town that I struck it big time. Our downtown church bought the building next to it and converted the ground floor into a resale donation thrift shop. Clothing of all sizes, styles, colors, outer and under wear. My mother worked sorting and hanging clothes. Needles to say I was expected to volunteer help also, usually fridays after school. The church had sunday school classes in the upper rooms. After church on sunday while the adults were at coffe hour in the parish hall I visited the closed thrift shop and exchanged any clothing I had borrowed the previous week. The trick was to always leave the clothes in better condition than when you borrowed them, cleaned, folded, mended, etc. Never was discovered, and it went on until the church tore the old building down for a parking lot about my senior year in HS.

[StacyCD]

I don't remember that far back! However, I know that I was interested in woman's clothing between 4-5. When I started wearing woman's clothing is a mystery that is forever lost.

[Barbara Dugan]

38 years old but I started having urges 10 years before

[Jill Devine]

I was 5 years old! I can vaguely remember sneaking into the basket that contained the clothing that had been washed but still needed to be sorted and/or ironed. Tried on my mother's pantyhose and the rest was history. But even before that I always wanted girls clothing instead of boys. But I kept the desire very secret and pretended to hate girly stuff.
Denial 101.

[Salina]

I was 15, my bedroom was in the basement which was 1/2 finished. The laundry room was in the other 1/2. One day I walked in the laundry room to get something and there were a bunch of my sister's panties hanging on a line to dry. I recall being intruiged by them, but did nothing that time. Every time my mom did laundry I would go check to see if the panties were there and the urge to try them on became stronger and stronger, it was like they were calling my name,....one day when home alone I broke down and tried on a pair of her nylon day of the week panties and was hooked immediately.

[Pinky188]

I was around 10 or so. I would go in my sisters room and put her clothes on! She is close to my age so they all fit! She had good tast also! She never busted me!

[cdmichelle48]

I don't remenber how old I was, it was before kindagarden, My sister and I were in a small room and we found a pair of silky ladies panties. I tried them on and even at that young age I was arroused. I never tried on clothes with my sister again but after that I was hooked. Every chance I got I'd sneek into the girls room and try on their clothes. I loved the feeling of the panties and panty hose and putting on their skirts and dresses, the feeling of being a girl. Very, very few people Know of my crossdressing. I wish I could dress more often and go out in public and pass as a woman. A lot of you CDs on this site are very beautiful, congradulations.

[susan2010]

I was 4 or 5 the first time I remember, but it may not have been the first time. For some reason I had to try on my sister's full white petticoat. I loved the softness and scratchiness. I wore it many times after that until she married and moved out. Then I discovered mom's slips and nightgowns. 50+ years later I still love petticoats and slips.

[alexiss]

First time...I was living with my girlfriend and she suggested I put on some of her lingerie. I indulged and liked it.

[alexiss]

That was 20+ years ago.

[alexiss]

I'm still shy about dressing... but I did buy a pair of heels today

[alexiss]

I know. I felt it too but was compelled to mask my feelings.

[alexiss]

I want to post a pix but can't even edit profile.

[alexiss]

I don't think my wife cares that I wear her clothes. In fact she asks what I think of combos she tries on. She doesn't like me wearing her shoes but oh well. I bought my own today..Merry Christmas to me.

[alexiss]

It's okay to b straight but like...no...love being in female clothes? Something about the taboo I guess.

[alexiss]

Am I talking to myself?

[alexiss]

I'll be back. XXOO. I'm heck on my new heels!

[Karen Johnson]

I was 5 or 6 years old and tried on my sisters white cotton panties and sun dress. That was almost 50 years ago and I still remember the exhileration that I felt.

[Laurenlovecd]

I just started this year at 42. I have always loved the smell of lipstick though and sometimes stopped to get a fix even when I was young.

[annie428]

lets see i was about 12 or so maybe younger. I remember putting on all my moms things and feeling so good. and all the girls in the neighborhood use to dress me an a few other boys as girls for fun and they could tell i liked it alot more than anyone else. but wow thats were it all began.

[Mary M]

think i was seven or eight. don't remember what prompted us, but my sister and i somehow decided to raid our parents closet and she wore my dads clothes and i wore one of my moms dresses and some pumps that were way too big for me. the rest of the family was home and they thought it was cute. it was a few years after that before i started craving to wear girl clothes.

[Drew Painter]

13 mothers thing, hamper...the usual

[Kate Lynn]

I really don't know,I joke around about the Baptismal Gown,robins egg blue with white lace,and white patent maryjane flats with cute white socks,but I really can't say.

I know I used to love wearing my moms shoes when I was 4 years old,my stepdad would pound the snot out of me as punishment,for several years he used to make me wear girls clothes to try to cure me,but that never worked,my favorite shoe color is bright red.

Now I dress in womens clothes all the time,mainly low rise boot cut jeans and skinny jeans,prefer heels with the boot cut jeans,and ballet flats with the skinny jeans,I'm not into wearing skirts or dresses in public,people here are ignorantly intollerant of others who are different.

It doesn't matter why I like to dress like this,I think it's just one of Gods plans,and proves he has a funny bone,as for my wife,she never has a negative comment about my choices,she says,"it hurts no one",and "some people do worse things".

[Tina Francis]

I was about 11 years old. My mother bought some nice skirts. I don't know why, but I loved the colours and flowers so much. When she wasn't at home I took them out of the wardrobe and tried them. They were far to big, but I enjoyed it.

Since that time I dressing more or less, depending on the situation and feelings. I will never miss these experiences.

[BLUE ORCHID]

It was about sixty three years ago when I was around
five or six years old with my mothers nylons and heels
after that there was no turning back.

The sad thing was becoming a teenager and moms heels no longer fit.

Maybe it all started when I was a couple days old I was dressed
in a little white receiving gown when mom and dad brought
me home from the hospital.

Orchid

[stefanie]

maybe 6 or 7.... i remember the excitement and anticipation as well to this day.... having 3 older sisters helped

[alli2229]

I was somewhere between 10 and 12. Love the look of the lacy undies mom and sister wore and once I tried them and felt how good they feel I never looked back.

[kimmie_sub]

I was maybe 7 when my mom dressed me as a European girl for Halloween but I was 11 when I started with my mother's panties, bra, panty girdle (like I needed it!) nylons and high heels. I remember how sexy the lingerie felt and the sexy walk the heels gave me. I would take things out of the hamper in our full basement and practice walking down there. I vividly remember wanting to be 'seen' as a girl but too afraid to come out to my family, so one summer day I gathered my favorite dress, high heels and lingerie from the hamper (my clothes closet back then!) and went to a local park & forest preserve. I changed there, putting a scarf over my head since I had no wig and walked the trails in the forest preserve, my heart pounding in my chest. I had no idea what I would have done if anyone saw me, or if a man wanted to get "friendly" but I went back several times, sometimes to also indulge in one of my fetishes too.

[Tammynnj]

Moms nylons at 7 or 8. After HS not again till my 40's.

[VTDresser]

I was 11. Our family was painting our grandmother's house and I was the unfortunate one that had to use an old rickety table to stand on to reach the area i was assigned.

I stretched a bit too far, the table couldn't handle the strain and it collapsed. I fell to the ground and the paint bucket, full of red barn paint, flew up into the air and landed on my chest.

Paint all over the place, all over me...quickly dispatched to the cellar to get out of the painted soaked clothes with nothing else to wear.

Grandmother comes down the cellar stairs holding a nylon night gown, nylon panties, and a towel. I had to go upstairs, shower, and put on the silky attire while I waited for my clothes to be washed and dried. It was the most intense four hours...raging arousal, laughter from my family, and shame/embarrassment.

Finally the clothes were dried and I could dress back into my clothes. I hated the feeling of my clothes...and the door that lead to the path of dressing opened that day to let me in.

[Debutante]

I was about 11 yrs old. My parents and family were away for a few hours. I found myself mysteriously attracted to my mother's closet. I tried on some
of her clothes, it being both very exciting, arousing, but also shame-producing. Later I tried in undergarments, then make-up. I did this for several years. I'll never forget it!

[Vintage4sarah]

Wow, this thread brings back memories! In my early pre-teen days, I use to raid our family hamper and try on my Mom's nylons and eventually her girdles. Since I was far taller than her, the fit was not always right, but heaven came when I "dog sat" my neighbor's home when they were away around 14 years old. Bingo, this would be the start of dressing completely as their clothes (mom and daughter) fit me and I was able to see myself in the mirror as a complete women. You can image how exciting this was. It last for at least three years and this really hooked me for life.

[yvonne10]

i rember i was about 5 when i sneeked into my mum and dads room and got some tights out of mums draw and wore them then i hid them in my room which i shared with a younger brother when he was asleep i used to put them on and get into my bed it felt great

[Virgin1A]

'bout nine or ten, I started experimenting. I was very fond of my sister's two-piece swim suit.

[herwannabe]

First time that I can remember was about 6th grade, so what? around 11 years old. My mother was very large breasted like 44, I would stuff those boulder holders with whatever I could wasnt till 12 that older sister came to live with that I had clothes more my size to wear.

Michelle

[Charleen]

My Mom's high heels at 4, her other things at 12.

[Julie Denier]

Can't recall the exact age ... I remember clomping around in mom's shoes as a toddler, and I was perhaps in my early teens when I would occasionally dip into mom's closet to try on a few things. But it wasn't until last fall, at age 38, when I assembled my own wardrobe for the first time and dressed fully, head to toe, including wig and makeup.

Julie D.

[Tina B.]

5 or 6 is when I remember trying on panties and bra, might have started earlier, but at 67 I don't remember a lot of childhood anymore. As to why, best I remember, just because I could, at it felt right.
Tina B.

[Jenn868]

I think I was around the age of 5 or 6 when my sister dressed me up into one of her dance recital tutu outfits lol. then here and there for years from girl friends and like womanless contests and halloween.

[gungho]

I can't remember the exact age but I know I was still in elementary school(4-5 grade, can't be bothered to do the simple math to find the age).When visiting my aunt told me and my brother about a trans person she hired and how she had no clue at first. It got me interested in the concept and I tried on a few of her things when everyone was in another room watching tv.

[missyvf]

I was 12 when I actually put on a pair of panties. I didn't dress completely...wig, make-up, etc. until I was 20.

[NathalieX66]

I must've been a full-grown teenager when i triend on women's clothes.

Anything earlier would have been girls' clothes...starting with my sister's. :heehee:

[markinhose]

i started at the age of 12 wearing my moms pantyhose. i was so addicted to the feeling i wore them almsot regularly until i was caught by my mom and 1 of my sisters. as time went on i was again caught by mom in her pantyhose. this time however my sisters were going away for the weekend for a sleep over at thier friends house. so it was just me an mom. she woke me up that sat morning told me to shower and that we were going shopping. when i came out of the shower mom had laid out some of my sisters cloths on my bed and told me to dress with everything on the bed. when i finally came out of my room dressed in a red dress a slip bra panties pantyhose and shoesshe took a picture and told me i was going out shopping with her as her niece. she put on some makeup and curled my hair a bit and off to the mall we went. she told me if i wanted to dress i had to have my own things, i was so exicited. i was actually hit on by the shoe salesman. as he put on 1 of the shoes he started running his hand up and down my calf. i didnt know what to do. anyways by the end of our shopping i had a dress bra a few pairs of panties and pantyhose and a pair of heels. . on the ride home she pulled over and had me drop a letter in the mailbox as i walked back to the car she told me she would meet me home and just pulled away leaving me to walk the 5 or 6 blocks all dressed back home. only problem was i had to walk by the park where all my friends were playin. needless to say i took another route home. all this was an attemp to get me to stop dressing however it only just lit the fuse.

[nancigirl]

Markinhose, Wow, what an interesting story. So after that memorable day, did your mom ever catch you again and find out that her plan to get you to stop dressing did not work, or actually backfired?

[ikthys]

My real first memory of it is from around 10. My sister's panties were on the floor. I liked her white silk panties with small lace around the waist. I wanted to look like a pretty girl. Mom's pantyhose came next at around 13, and quickly everything else too.

[kati57]

I was 10 years old when I first started wearing womens' clothes. The initial view was as I saw I woman, wearing a skirt, nylons and heels walking around a corner in my hometown. Still remember that picture.
And of course I had to try and make myself look alike. So I took the next opportunity and dressed in what my moms drawer had to offer. And I took my time, so by the time they came home , I had to rush and remake myself presentable. Actually I was just putting my sweater on when they saw me coming out of the bathroom. "I was just sweating so much and decided to wash myself" was my excuse as they trapped me like this.

I will never forget the view of that gorgeous woman!

Kati

[Heathersgams]

Great thread, probably confirms what surveys would say. However, I'm feeling a bit late to the party, started at 42. Late to the party.... story of my life LOL

[Kim Welcher]

I was 3 or 4 years old when I was forced to wear little girls panties for a reason out of my families' control. It was later when I would watch tv shows that showed male characters crossdressing that made me curious what would it be like to dress like a girl. Finally in the 7th grade I took the plunge and wore one of my mother's dresses when I was home alone. I've been dressing since then.

[Charise52]

I had just turned six, when my mom got me a gitl's denim skirt (knee length) and matching top... I loved that outfit and wore it everwhere all spring and summer and into the fall until i started school... then i wore it on weekends... I really came to love the feel of a skirt...

[Juanita O]

I was 10yrs old

[jessicaheartt09]

I was maybe 6 at the time and I was in my younger sister's room helping her clean up and then we played with her porcelain dolls for abit. I then asked her if I could try on her dress she must of just got and worn somewhere. It was a black and red velvet stretchy material dress and I tried that on and a pair of tights to go with it. After that every so often I would get dressed on and off but always feeling more similar to girls and always jealous of what they were wearing if I thought it was cute.

[bostonbecky]

I want to say it was about ten years ago when I was 8... rummaging through a box of old clothing with a friend I came across some random dress, jokingly I told him to wear it but he refused so I tried it on, at that point in time it was just a funny joke. I don't know how or why but when I was either 12 or 13 I just had the urge one day to wear panties so I went into my sisters room and wore some of hers... After that I started wearing my mom's clothes because they fit perfectly but now that I'm in college I've been able to go panty shopping for myself and am seriously looking forward to beginning my own wardrobe :)

[CaitlynRenee]

Oh MY! New here, so here goes.......

I don't remember if I ever commented here before, but if not I'll do so now. I've been reading this site for a few years and have found great empathy and comfort here. Thanks.

I first remember when my Grandmother did the wash one day and forgot to put my underwear in. (The only guys were me and Grandpa in the house since my Dad was overseas in the service. Mom was a nurse and my younger sister and brother hadn't been born yet.)
Since Grandma was only doing the lingerie that day, I had to wear my older sisters panties and silkyshift. When Mom got home from work, she laughed and told Grandma I looked 'cute' . I did at that age I suppose. Grandpa was too busy to notice or at any rate didn't seem to care. Since it was easier to buy just one type of undies for 'the girls', I ended up being dressed until about the age of 5 or 6. Along the way, I was the full size 'living doll' that my sister and her friends had always wanted. My toenails were painted, my lipstick was their favorite. Gramps never said a word and told me years later he didn't think it mattered. I was who I was and should be proud of myself, no matter how I felt. Pretty advanced for a burly guy who raised himself living off the land from the age of 10, as an orphan. Also perplexing to me at the time since I'd never felt any 'need' to express myself by dressing, enfemme. Confused, but compliant...... Yep, that was me.

My life followed that of many men. A 22 year career in the Marine Corps saw combat duty in the Republic of South VietNam in the space of two years 'in country'. Fifteen years as a Sheriff's Deputy followed that. The rest of the time, I've been a 'house-hubby' which fits my personality just fine. Dad always said that if I couldn't clean my own clothes, darn my own socks and cook for myself, I'd never make any woman a good wife! (OH he knew me so well). During my time 'in country', I had a trophy pair of silken panties from a sweet little girl in Thailand that I spent a week with. Believe it or not, SHE gave them to ME. Said they 'might not fit'. Hmmm Did she know???

To bring things up to date now, I have a career Air Force son who just may be CD (he was in High School), a beautiful college freshman daughter who is Bisexual, a gorgeous arrow straight wife with her own career who has passed the 'big M' in her life and is not very interested in sex any more. The wife and daughter know of my clothing preferences and the wife buys me nice things from time to time. I've slept, cuddled, and made love while enfemme. I'm dressed now (underneath). When dressed, I have the normal feminine fantasies. When in macho mode, I hunt, fish, work on my truck and Jeep and garden while sipping a beer and don't have any feminine thoughts. Women totally turn me on. If I were a woman, I'd be bisexual.

Being 'enfemme', makes me feel at peace. I don't feel the need to prove myself to anyone. I need to be held and comforted. Truth to be told, the softness of nylon, silks and satins has a calming effect on my tortured soul and helps make the pain of loss from my years 'in country' fade away............ for awhile.

Now if the wife and daughter would just let me shave the mustache!
In kindergarten, I put on some of Mom's panties without knowing why. She saw me and said they were too big and to take them off. Next day, I found four pairs of brightly colored nylon panties in my drawer. Heaven?? Ohhh YES!

[Katie Mathos]

I was 13 years old the first time I tried on a pair of panties, bra, and girdle. I've been dressing part-time since that time. (I'm in my 50s)

[Jess Marie]

I was 9 or 10 when I tried on a pair of panties. Been full time panties ever since and just recently started wearing a bra to lounge around in my room

[linda allen]

My mother had no daughters but she liked to sew so she sewed dresses for her nieces. She made me model them so she could mark the hems. I often wonder if that's at the root of my desire to dress - to be the girl my mother always wanted.

edit: I forgot to answer the question. Probably five or six years old.

[JenniferLynn0370]

Well, does being brought out of the delivery room in a Pink blanket count? Beyond that, I started before I really remember...my parents will unashamedly show the "cute" pictures of me with my elbow length white gloves on and white purse in hand waiting to leave. I apparently carried that purse a long time. I do remember being told by my Mom once that "you don't need your purse for this trip sweetie". I have always crossdressed; more at certain times in my life than others, but never enough!

[Meghan]

I was 6, just starting the 1st grade when my babysitter let me have her boots!

I wore them to school the next day, then I got a talking to from my mom...then I didn't get to wear them out again

Meghan

[Morganx]

It started around six or seven with me. I'm pretty sure The Benny Hill had something to do with it.

[Newmichelle1959]

I was 11. i had just lost a bet to my brother ( we were home alone after school). As "punishment" I had to put moms bra, panties, hose, skirt, top and heels on. Just as i got it figured out, guess who comes home early.......you got it! Our mom.....needless to say, my REAL punishment began. I was made to wear a dress to church for a month AND i had to wear a bra and panties under my school clothes. I didnt tell her until i came out as Michelle years later that she actually helped me find the real me.

[Joanna_81]

Unfortunately I don't exactly remember that "very first time" - neither "when" nor "what I was wearing", which is actually bit strange, because I have lots of even very early memories. I can only say that it was certainly when I was already going to school (so was above 7), and before I was 10. But from very early age I was showing some very un-boy-like interests: I loved to play dolls, or "house", or "school" with my older Sister and was very interested in my Mums sachet with old lipsticks, eyliners, powder etc. My Mum was very unenthusiastic about all of it (she wasn't too tolerant about such issues), but since I liked to play with toy cars, She assumed that it's just a stage I simply need to pass and fighting it won't help. Well, now I know that it rather didn't pass. ;)

[Jenniferathome]

7. Just panties then. Put on my first dress at 12 and LOVED it! I remember like it was yesterday.

[ginafaye]

i kinda remember having to wear my older sisters panties a lot. it was just a hand me down little kids thing . i think mom just thought under wear didnt matter to kids. i was 4 to 8 ...and later she took in sewing and i was always the dress dummy never my sister...wish i would have figured it all out back then maybee i could have gotten some bras and pantyhose a lot sooner

[k lynn]

age 5

[Tara Jordan Campbell]

Can't remember exact age but I was young, maybe 6 or 7. I used to go through my Mom's dresser looking for anything silky. I would take the items and put them all on, jewelery and lipstick too.

[Jennifer Freeman]

Attached is a photo of me aged 8, in August 1944:o - when I began wearing my Mum's and my Sister's knickers!:devil:
Jennifer Freeman

[*~Cassie~*]

Must've been 6 or 7, dunno if it was my mum's or my sister's, but someone's bra was hanging to dry over the bathtub, and it just looked nice so I had to try it on, naturally :)

[Kathryn Philips]

I was 4. I used to play a clothes swapping game with my female cousin of same age. How it started, I'm not sure but surely it must have been my idea.

I also remember at the same age asking my mother if I could wear a pair of white sandals (similar to attached image), and she did let me wear them a few times. I am not sure if they where her own or she actually bought hem for me, because as far I remember they seemed to be the right size for me. I have never asked her about this, maybe one day.

When I was 6 or 7 we had a female house guest who would spend a few nights a week at our apartment. She slept in a spare bed that was in my room. When she was away I would sleep in her nightie, which she kept under the pillow.

[Annie M]

First time was about 7, I dressed in my moms clothes while mom and dad were both at work, I had about an hour on my own, they thought I watched TV ha! Never quit, loved 60's and 70's dresses, and was so jealous of the girls at school. Back then they had to wear skirts but didn't want to I wanted to but couldn't, life just isn't fair. One girl I knew wore a yellow dress with buttons up the front I really wanted one like it. I saved and bought something similar for my mom. Well it didn't really work for her as it was a bit short and the sleeves were oh so 60's but I really enjoyed it, and she of course, would not wear or toss it. Later mom ran a dress shop and as young teen I told her I would clean up the place in the evenings and weekends, vacuum and dust etc, it was CD heaven.

[joan658]

I think I was around 10 when I first tried on some of my mothers lingerie.

[CarlaWestin]

Yes, growing up surrounded by females and all things feminine I believe set the tone to have male and female personae. I was perfectly comfortable playing with my sister and her friends with dolls and dress-up clothes. For some reason, around age 12, I became fascinated with wearing my Mom's bras under my clothes. Also, little pervert I was, I wouldn't miss any opportunity to explore a neighbor's or relative's lingerie drawer. Found some really great stuff but never took anything.

[Paula Siemen]

I guess I was 11 or twelve when I started raiding my two years older sister's bras and panties when I was home alone. Tried on a few dresses but wasn't able to zip up the back. On one occasion I was home alone and had my sister's one piece swimming suit on. I heard the front door open and didn't have time to get out of the swim suit. OMG!!! I was frozen in fear! With my sister, was the older sister of a girl in my seventh grade class that I had a serious crush for. All I could do was get into my sister's closet and shut the door and PRAY they didn't need anything from the closet. I was shaking so hard, I'm suprised they didn't hear my bones ratling. They were in my sister's room about three minutes and off again without a clue of me in my sister's closet in her swim suit. I nearly collapsed with relief when I heard the front door close as they left the house. All this as it was.........it didn't stop me from dressing again in my sister's clothes.

[Monica Mercury]

The first thing I remember was my Mom's pantyhose and silky slips; I was about 7 or 8. I quickly progressed to skirts, heels and makeup, but shut it down for the most part around 13. It wasn't until a couple of months ago that I fully dressed again (I'm 41). It's been repressed and such a source of guilt and shame, but it's so liberating to finally embrace who I really am and not beat myself up over it. I'm dressing tomorrow with two close GG friends and I can't wait!

[tammii1111]

Dressed up in moms lingerie all the time at age 12-13 or so. Dressed as Tammii for the first time at about 22-23 and have ever since when time allows.

[SusanQ]

I was about 5. We had a step-child living with us. She dared me to put on her panties and slip...I did it. Felt really good too!!

[christine55]

I could not possibly have been any older than 5 or 6. Was visiting my aunt with gg cousin. Went into bedroom to took nap and a full slip was sitting there on the chair. I remember that I had been wanting to wear girls stuff a year or two before that. Anyway, I put on the slip. I so wanted to just leave it on but I was too scared. Didn't dress for a couple of more years when I neighbor boy wore his sisters stuff. I of course joined him. Was too afraid of being made fun of that I only did that once. Started sneaking my moms petticoats shortly after that. My brother caught me dressed when I was about 12 and for a few years after that would get dressed when my folks were out and I would play girl with my brother.
If I had been braver my life would really have changed when I was about 20 when I girl I knew told me that she wondered what it would be like to play the male. My hung up secretive self really effed up. If I had taken her up on her not so veiled offer I would probably now be ts and I would have had my youth as a girl. Long hair, my own done in a salon. We miss
so many opportunities. Seems like I am getting a few opportunities to know some very possibly sympathetic gg's pretty well. Who knows. How I would love to take a vacation with a gg
as a girlfriend. Even live together as girlfriends. Wow?
Hugs, Christine

[missyvf]

12 for me. best friends moms panties

[Christina..x]

i was 13 wore snow white dress :)

[UNDERDRESSER]

I first tried on my sister's clothes at about 8 or 9, someone had the idea we would switch, ( I think it was her ) and we changed either side of the bathroom door. My Mother came home and caught us, she was pretty mad. Thing is, I had had a weird fantasy about a girl at school when I was maybe 7? Somehow this linked into it, and in my memory I "modified" the daydream/fantasy to incorporate the crosssdresing thing. I went on from that to sneak into my sister's stuff from time to time. I did try on some of my mother's stuff, but there wasn't much opportunity, and the sizes were so different. Whereas the fact my sister's stuff was a bit too small. and tighter! Still have a thing about those green school knickers even now....

It's definitely a fetish thing for me, I'll admit to having a strong feminine side, along with a strong masculine side, but I don't feel there is a girl inside trying to get out. Almost all of you have a name for "alter ego" I don't really see myself that way. I'd like to try full en femme, but would need some heavy duty help to be convincing, and the thought of the way I would look without that help, really turns me off..

[Christina..x]

i did ballet when younger always expressed femine side girls played prank and took my original ballet clothes replaced it with skirt and tights how embrassing it was then picked it up from there

[lynnlmb]

I was 10 when started to wear my sisters panties .they where all nice silky noylon panties

[crystalbath]

I was about 13 i think and i tried on panties for the first time

no idea what ever made me what do to do it, all i know now is - i love it :)

[HK SPICY GIRL]

About six my sisters dressed me up.

[MercedesFantasy]

I was 6 or 7 when a friend and I got into his sister's dress up clothes. Over and over and over. I still remember one silky blue dress that I wore!

[BillieJoEllen]

I had been dressed in girl's clothes many times as a child. Girl's panties and T-shirts because my boy undies were 'dirty'. Baptized in a frilly white dress when I was 3 and a half, used as a dress model by my mother until about 11, forcefully dressed by an aunt when I was between 6-8 yrs old and encouraged to dress as a girl for Halloween when I was 11. It was this last incident that led me to experiment some more because of some comments I heard some girls make. I soon developed a curiosity about girl's clothing. I tried more and more things finally turning to try on women's things. I could have given up CDing at that point but I happened to hit the right combination of clothes AND WOW!!!! Its at that point I became a CD and never looked back....

[Linda Stockings]

At about age 7 I tried on a pair of super sheer RHT stockings my mother had discarded because of a run in them. I loved them and was probably hooked then and there. I went further one day while home "sick" from school at about age 14. I borrowed my sister's stockings, pantygirdle, bra, slip, and shoes. I was so taken with that feeling that it made me dizzy. I've been CD'ing ever since, and have been out in public many times, some successfully, some not so much. I still can't get my face to look feminine. I wish I knew a really good makeup artist to teach me. Anyway, the bottom line is that I started very early, loved it, and never stopped - like a lot of ladies who have responded to this thread. The similarities are fascinating. I wonder: how did we all start in such a similar manner? Linda