At What Age Did You Start To Crossdress? / What age did you start cross dressing? Why

I'd have to say about 5yrs old I was in my grandma's bathroom and her stockings where hanging there and I wonder how those would feel on my legs it was great as the yrs went by I tried on more of her stuff I can even remember my kindergread teacher 4in blk pumps :love: of corse the day i was caught I was dressed head to toe no getting make up plus a girdle off b-4 your found hiding alot of talk and yelling I was sick and needed help I was a boy for along time but thought of dressing all the time to any new cds don't toss your stuff out and think your normal agin it don't work that e-z I belive I have a female soul inside of me somehow and she loves to shop on at 53 I still like to get all dolled up and somehow I know I'd do it all over agin

I statred a thread like this too. I started at 7 with my moms panties,pantyhose and knee socks.A few months later I tried my first skirt.At 10 I tried a bra and top too, in my teens i grew my hair out at 18 to my bra strap. I then started to wear panties 24/7 , I also wore girls jeans ,tank tops,and wore my hair with barettes,updo's. That lasted into my twenties until I needed to tone down to get the job/family. I just crossdress when I can now.
Sarah

I blame Pans People (that’s done it, how many UK girls out there remember them,
Just shown my age up)
They where a dance group who appeared on a TV program Top of the Pops
in the __ __ es.
Well my mom’s girdles found another use
I did not really get going until my twenties

I was about11 when istarted.I borrowed panties at first.At about 13 I started wearing my sisters jeans.Even wore them to school a couple of times in high school.I really do not know exactly what triggered it though.

Between the ages of 5 to 10 I had the occasional desire to have my nails polished (like my younger sister) or wear lipstick (like one of my teachers). I didn't get the chance until I was in the school Christmas play choir at age 11. They wanted us all to wear lipstick for the visual effect. I remember my dad saying I'd never let them do it to me. I did, and it changed my life.

Not long after, when home alone one day, I went searching for my mom's lipstick. As I searched through some dresser drawers I came across her bra's. I couldn't resist the urge to not only have the lipstick on, but to have a bra and a top on also. As you all probably know, it felt unbelievably fantastic!

After that I tried to stay home alone as much as possible.

It still feels as great today.

I tried on my mom's inderwear when I was about 8 or 9 and always had a fascination with sexy lingerie------but it was 40 years later that I finally was able to fully enjoy the pleasure of dressing like a woman-----and I will always regret having wasted all those years

Under two :
As an infant I was placed in opened bottom dresser drawer to sleep. My parent's apartment bedroom had no room for a crib. Their landlady did not allow children and they moved when I was about six months old. Perhaps this was the dresser drawer where my mother's undergarments were kept. I have an aural memory of this as well as a life script (since overcome) of "be quiet, don't cry someone will hear you (the baby)."
I have mental images of watching my mother dressing as I lay on her bed--I must have been a toddler.

About four:
Wanting a dress like my sister had received on her second birthday, We share the same birthday day only two years apart. Apparently, I threw a tantrum, but I cannot remember if I ever got a dress.
I can clearly remember the feeling and visual aspects of my first babysitter's stocking clad legs as I walked around her or sat on her lap. She was a kind, older woman.

About five or six:
Being small enough to hide under tables and occasionally view the ladies from that vantage point. I do remember being at a wedding party and hiding under the longs skirts of somebody's dress.

About ten or eleven:
Taking stockings and underclothing out of my mother's bottom drawer and trying them on.
My sister had some dress-up clothes that consisted of high heels, old stockings, crinolines and slips that had belonged to my mother. These were in the basement and on occasion I put them on

Around thirteen to fourteen:
Being home alone all morning before going to high school (afternoon class schedule) and dressing completely in my mother's clothing--from the undergarments out--often including a smart looking basic black dress.
I also tried on stockings and a few garments at my grandmother's house while she and my grandfather were away in Arizona.
I was caught once by my father. I do not believe he told my mother. He got me a book about the facts of life, asked once if I had any questions and never talked about my dressing again--even as we sat alone together in his hospital room near the end of his life. Throughout my high school years, he did encourage and financially support my hobby of model railroading--perhaps thinking that it would keep me out of the bottom dresser drawer.

One of my earliest childhood memories was going downstairs and finding newly washed panties on a pile of clean clothes and having a overwhelming urge to try them on (of course doing so). Must have been 4 or 5. Became a panty thief in my preteens (mom's and sister's) and aside from the ussual purges and swearing to give it all up I am still crossdressing.

When i was about 12 or 13. at the time i lived with my uncles, in a house next to that of my parents. I used to sneak in and wear my mom´s things...

Like most it was early in childhood 7 or 8 and it was mom's pantyhose and slips . I soon discovered shoes and that has become my passion. In drab I wear a men's 12 so I have had a hard time finding womens shoes that fit me over the years but love it when I find a sexy pair that I can wear.

My earliest memory of girls clothes is my sisters school knickers-bottle green and big, but magnificent to wear.
That started the usual rummage through wardrobes for the rest of my teen years.
I would wear nighties to bed, under my pyjamas, getting caught twice by little brother who shared the came room. A bit of teasing is all I can remember.

Earlier than that though I remember being put in a nappy by an aunt whilst staying over at her place and this started me on a bit of age regression role play. Playing with dolls and other girls toys and finding substitute nappies. I would wear them to school on occasion until a spate of "debagging" caught on and I was petrified of people discovering!
After that it was strictly home only for me. Overnight under "my" nightie.

My mother found my stash on a couple of occasions and confronted me but I stammered something and wriggled out of it. I would have wanted to tell her but my dad would have killed me...


Bye ladies

Stella

Actually one of my earliest memories is putting on panties, was too young to understand (4?) new it was wrong, but it felt so right

I started around age 8 or 9. My parents divorced and on weekends my brother and I would stay with my Dad and Step-mom. She had a daughter 2 years older than me so there were plenty of clothes to try. My favorite was her Cheerleaders outfit. Short skirt, crop top, and Pom Poms!

I have dressed off and on all my life with a few periods of a year or two without. I have dressed pretty steadily over the last 7 years.

I started Cding at age 14 yrs , during my schooling , now reached to college level .. though caught twice one by mother and my elderly sister and both the time escaped ..

I started cross dressing for fun ,but that fun proved to be birth of girl inside me and iam now regular cross dresser , though I have stop for some time in between ...

the outfits are mainly Indian , and I love them too much ... ummmh .. but still hesitant to buy personally but thinks to do it soon , so that i can have my favorite specifications

I have an older sister and two younger sisters, and I used to get dressed up with them, I can't even remember how old I was. As I got older that became less acceptable to our parents, so I started dressing in secret around the age of 8. Borrowed/stole pantyhose, slips, bras, etc.

Why? Beats me. If I suppress the urge more than a couple months it gets almost unbearable.

I was 5 years old was the first time my dad devoice from my mom in 1973 mest up her head and she hated men and started drinking and hanging out with her girl Friends for support.
So to make a long story short I was my fathers son and she was going to fix that so my hair grew long and she started treating me like a girl so that easter I got my hair done at the beauty paler and a new dress and white Patin leather shoes lace sox and panty hose and it started there and has not stopped even when I had the choice! It really made me a better male to be treated as a girl for so many year and I never dated any men in my life I would find girl that liked other girls so the dressing would not get in the way.
They were happy and I was happy win win.
My wife now was striate from the start and she still like me for what I am but I do hide it from my kids But my hair is still long and I still shave my legs and arm pits every Friday so if I want to dress it takes me about HR to curl my hair and Min to put on some make up and all set to go.
Jackie

I got interested in dresssing around 16

when i was 13 my twin step sisters dared me and i liked it so i kept taking mums and sisters cloths they were about 10 at the time and have forgot

I Remember Being In The Back Of The Family Station Wagon On Vacation When I Was 10 Or So Just Laying There Praying To God To Make Me A Girl. Dont Know Where It Came From But I Will Never Forget That

Talk about late starters, I think I'll honestly report "my mid-sixties"; and that was initiated as a prank by my good wife and our camp mates at Burning Man (burningman dot com). I remember at pre-school age clumping about in my father's shoes, but nothing else.

I was three. My mother was getting ready to go to college classes and I remember vividly laying in a basket of fresh laundry. I was surrounded by her clothes, and although that sounds erotic, it actually felt right.
Even at that young age I already knew I was different.
Panties were always my downfall because I could wear them all the time. Even under my boy clothes, I could be myself and nobody could take that from me.
When I was eleven my parents divorced and lost the only male influence in my life.
Now, when I was six or seven, I remember my father catching me in a pair of panties and damn near beating me to death yelling "You're not a girl!!!"
The funny thing is, I never thought I was. I just knew something was different about me.
Anyway, I spent my teen years in the early 80's surrounded by nothing but feminine influences.
I experimented a lot with making my own fake breasts, and discovered the wonders and joys of pantyhose.
I dressed in private all through my teen years. Fortunately, the androgynous look was in, so I could push the rules a little and get away with it. It was during this time I played with makeup quite a bit. You can see pictures of me as an 18 year old and god, I looked great..
In my early adult years I went through a few instances of trying to purge, but have always found myself allowing myself the one thing that society frowns on but makes me feel whole.
And now, I'm married to a woman who is not only understanding, but dresses with me, for me.... dresses me. :)
And in return, she is treated like the amazing goddess she is for accepting me exactly as I am.

It started when I was 14 15 years of age. When I found a box lingerie.

I think I was about 10 or 11 when I started crossdressing. I would sneak some of my sisters clothes out of her room when I had the chance. Everything from panties,bras,tights,skirts,tops,dresses. I would go back to my room and try her things all on and oh how I loved the feeling! Then when I was done with her things, I'd sneak back into her room and carefully put everything back where I had found it. I don't believe I was ever caught, but my sister may have had her suspicions. Although she has never to this day said anything to me. I love dressing as a woman, the clothes just feel so much better than a mans. The only thing I haven't done is shaved or gone all the way with the makeup. I don't have a wig either so I only dress in the privacy of my own home. I am pretty much a closet cd'r. :sad:

Hugs....Melissa

wow great post! It started for me about age 8. I remember when my mom used to take a nap in the afternoon she had left some panties out and also her bra, of course I had to try them on. At the time i don't think that i put 2 and 2 together, just a curious boy. I think when it all sunk in, i was about 19 yrs. old and parents away for the weekend. I went through my mom's drawers and found a brand new pair of black pantyhose (control top) i tried them on and the rest of the weekend i never took them off. What a great feeling. After that I have always had at least one pair of pantyhose in my drawer. The urge to try on other items came just about 2 yrs ago, in my late 30's. My wife had a dress that i was dying to put on it was a little black dress and oh so sexy. After that there has not been a day go by that I have not had on at least a pair of panties or hose.

At What Age Did you start to cross dress?
I would have to say I started at 18 I was a late starter. However I remember walking home from elementary school and hanging on the chain link fence at pair of panties and bra. Pink I think but from that point on I love what I saw. Wow to see that at my age I went straight home and being an artist I went into my mom’s closet and drew a picture.

After that I did not think much about it until 10 or 12. Then puberty hit then I started looking through magazines and seeing women’s ads for panties and bras so I cut them out and looked at them all the time. I always wondered how they felt so it wasn’t until I had my first girlfriend that I got to try them on they were her pair and wow it was great.

Then I was out of my parents house so I bought my first pair they were playboy panties and I wore them all of the time and never looked back.

So 18 I started cross dressing.

What age did you start cross-dressing? Why

Also at 18 my girlfriend dolled me up in here clothes. It also felt great however I did not buy any clothes because I was afraid of being caught. I just stayed to panties and bras however that was at the time a hard thing to do to. However you could not try them on you just had to buy them. Clothes you have to try on.