Ever wonder what made you try it on?

[Julia Cross]

Besides what item we first started with, I often wonder what gave me the curiousity to try it on in the first place. In my case, nylons. It's not that every boy thinks to do this, so why did I?

Anyone else wonder why they thought to experiment in the first place? Had I/we never tried this, would I be a crossdresser today. Was it simply meant to be?

Julia

[Sophia Rearen]

Why did I have to watch the NewlyWed game that day??

[Deborah]

I remember being a little girly anyway. So when i saw my sister's dress laid out for her to go to school the next day all i can remember thinking is "why not?"

[CarmenG]

I guess it was me. I felt different, my early years were directed in that way, but that did not feel the same. I knew I was doin something that I was not suppose to do and getting away with it..... it's been a lonf time ago but I think that was it.

[Holly_of_Bucks]

Oh it was long ago and far way. I just held that scrap of cotton and thought, 'Why not'? Then when it had slipped onto me I began to know.....

[tammie]

Hi All: Like most lifelong CDs I ahve contemplated why did I ever try on a bra. I started with my older sister's black lacecup underwire bra laying so innocently on the floor. As soon as I slipped my little boy breasts into those cups and felt the underwires supporting me I was changed in that instant into a lifelong crossdresser.

There R two incidents that may have come into my subconscious desire to try on a bra. It is unclear to me if I would have done it anyway or if I was led to do that.

The first incident was when I was about 5yo, my sister 9yo. My mother had my sister and 2 of her little friends over and perhaps I was being a pest, but my mother playfully said "Lets see what U would look like as a girl". She stripped me in front of the 3 little girls and then put me into my sisters white cotten panties, lacey socks, maryjanes and a blue gingham party dress. I was crying, but stimulated. I remember it quite well. Then my mother said "look at this cute little girl". I was dressed that way for several hours until my sister's friends left.

The second incident that may have influenced me happened not very long before I put on my sister's bra. I was at my friend's house after school and was wearing a thin Tshirt and levi's. His mother who was a beautiful young woman I was quite smitten with said " U should wear a bra, your nipples R as big as mine". I was absolutely embarrassed almost to wanting to die right there. It was only several weeks later that I put on my sister's bra, and I was off to the races and have never stopped. Although like many I have purged and tried, only to restart and expand on my wardrobe of lingerie to where now i have at least one of everything I think.

[Donnie]

the sheer feeling of lace, silk - oh, I have to stop

[linnea]

This is an interesting question to me because I can remember the situation quite clearly, but I can't remember the reason or reasoning. I was about seven years old, so a lot of time has passed. However, I have had a few "flash backs" of memory, especially in the last ten years. These have opened up some renewed memories. I think that the reason for the flashbacks is that my mother died at that time and a few years before she died, she revealed something that happened in her life at the time I was about seven years old--she had another baby. My older brother and I were being reared by her alone, since my dad had died when I was about five. My mother dated a little, but in those days for a woman to have pre-marital sex was still somewhat scandalous. So when she got pregnant, she apparently felt that she needed to keep it a secret, particularly because the father was a married man.
I still don't know some of the details, but I learned quite a bit when the child she bore came into our lives on a quest to find his birth parents. He had been adopted at infancy, so my mother never knew him. NOW BEFORE AN ADMINISTRATOR SAYS THAT THIS IS OFF THE THREAD, let me say that my first "try on" was a Playtex rubber girdle. I put it on and stuffed a big towel into it. Looking back, I think that I was simulating the appearance of pregnancy. At the time, I did not consciously know that my mother was pregnant. My mother actually caught me, and only said, "What are you doing, Johnny?" I answered, "Nothing." She never said another word about it. But from that time on, I began trying on my mother's underwear and eventually whole outfits of her clothes. That was over fifty years ago. In some future thread, I would love to tell more of the story and some of the other influences on my dressing--including the fact that my mother had me wearing girl's panties from very early age until I finished the sixth grade.
So that's part of my story of my first "try on."

[angelinamillar]

Strange one really. I alway remember when I was very young that i had a security blanket, u must remember the old blankets with the holes but most importantly the silky edging strip, I remember the silky fell of it and used to love the feeling of it when i went to bed. the silky feel i discovered was the same as the feel of legs in nylons. Now the feeling of wearing nylons and the touch of them, I was only about 7 at the time, And so it begins :)

Hugs

Angelina xx

[MarinaTwelve200]

Besides what item we first started with, I often wonder what gave me the curiousity to try it on in the first place. In my case, nylons. It's not that every boy thinks to do this, so why did I?

Anyone else wonder why they thought to experiment in the first place? Had I/we never tried this, would I be a crossdresser today. Was it simply meant to be?

Julia


I think a whole LOT more boys than we think, think to do it---out of curiosity, mostly. Considering how many of my friends in their teen years dressed as girls for halloween, (I didnt BTW), and noticing the nervous reactions of other friends and adult males when the subject of women's clothes comes up (even my father)---I would dare say that at least 80% of boys have tried on an article of female clothing at LEAST ONE time in their lives.==Perhaps even more. For most it may have been a ONE or two time thing that satisfied their curiosity, and that was it. They just NEVER tell ANYBODY

The minority, of boys , though, are the ones who KEEP doing it. The clothing either "resonated" with them or gave them feelings of pleasure. and /or relaxation. These are the one ones who become Cross Dressers.

I started at age 12 with lipstick myself---I was curious to see what I would look like as a woman (so i told myself) I also had a "fear" of it since I was ALMOST "lipsticked" by some teenagers (and later my mother) at age eight. ---The curiosity and fear finally got the best of me, and I finally put it on my myself , when home alone one day.==I got quite a rush from it, but I never could get quite a handle on "what i looked like as a girl", which lead to adding more and more items to my CDing---dressing completely by age 14.----and I STILL do it.

[prohetJoel]

when I rember is the curousity of looking at my mothers dresser drawers of clothing and was fastinaticed by the feel of panites. I touched them and it felt what they where like. so like it. so I was alone and put them on and has been for sometime now. I liked them I was young now I am a man I even wore my moms prom dress.:happy:

[Diannna]

They say we really can't remember much before the age of 3 or 4. But I swear that at around 3 or 4 I remember wearing my mothers long leg snap crouch girdle. I would put it on and hide under the bed. Then I can remember wearing my grandmothers open bottom playtex girdle, and hiding behing her rocking chair in her bedroom. Don't know what it was about the girdles but I have a special fondness for them till this day. I never dress without wearing some sort of girdle.

[Joanna0909a]

OK, this is a really interesting question, one of which I have given a lot of time too. Like many, I have purged a number of times only to start over and get even more sophisticated in my dressing. Anyway, when I was about 11 or 12, I accidentally saw this picture of a young model wearing nothing but two LP records. Something went "Click". About one day later I tried on my moms panties and bra. 40+ years later I have now admitted that the picture actually awoke the female part of me that was always there and always will be there.

[Shelby]

I remember as a little kid, my sister and I found our mom's slip, we both tried it on and my sister even run down to show mom, she wasn't happy. Growing up, we were trained to do the laundry, so you naturally end folding the clothes which include panties and bras and nylons. It felt weird to handle these items, like I was breaking the rules or committing a crime. One day while folding I decided to try on a bra and a sweater of my mom's and my sister came in, laughed and left. It was like forbidden fruit, they are things that men don't wear, but are simply curious to know more about. Then my mom bought a dress for my sister from a garage sale. It belonged to the hottest girl in my elementary grade class. I had such a crush on this girl and now her dress was in my home - naturally I felt the need to wear it. I gave me a connection with her. The ability to feel so close to someone who you physically can not be to yet wear something of theirs (legally in a round about way).

Once I got my first apartment in college, a Vic Secrets mag came in the mail addressed to the previous tenent or current. I decided what the heck, I single, living on my own with my own money and mailbox - why not. When I moved back home after quitting that college, I purged those items just incase because I was really scared and not so confident. Then I helped to create a community theater and the first show I we did involved a guy who had to wear a dress - I thought that would be cool to do. The funniest thing about that show was this girl who was the damsel in distress (a melodrama play) had to go in disguise as a boy and played my brother. She forgot to bring a pair of jeans to the performance and wore a pair of mine that I wore to the show. So now I have this hot blonde girl wearing my pants and I get to wear them after her - how cool is that. Well I always said, if you're in theater long enough, eventually you'll wear a dress. Well that time came with a musical we did and I had to dress up as a greek courtisan. Only I grew a beard for the show. I had fun and found an outlet to wear women's clothes in public for theater events without anyone realizing my secret desire. I still feel that wearing women's clothes is a way for me to feel intimately close to one since I have been single. I keep thinking that that feeling will subside once I am in a relationship, but after reading from many of you - I don't think that will be the case. I don't forsee myself coming out to anyone, but I'd trade the feel of wearing silk for the feel of a female next to me anyday.

[kwebb]

It could just be simple curiosity, in my case I just don't know. I remember these cheerleader bloomer type drawers in the basement sewing room I tried at about 4 yrs old. Then when I was 10 and in the 5th grade I was looking at my teacher's stockinged legs one day and it was as if I got possessed by something. Like someone literally flipped an "on" switch in my head. And from that point on, its been on. From the time I got home from school that day I started scheming and trying to do it.

[annekathleen]

Why I tried them on?
Perhaps it was the way they looked, perhaps the way they felt.
Before I started buying my own, I used to "borrow" quite a few
from my girlfriends, their sisters, my buddies sisters, my cousins friends, my friends wives.
Just knowing that those beautiful ladies once wore them and that those panties were once so close to their private areas, I couldn't wait to try them on.
Then, once they were on, the feel of the fabric drove me wild.
And looking at myself in the mirror as I was wearing them,
well, you know, one thing just lead to another.

[RenaCD]

I remember like it was yesterday, Once Upon a Time, Long Ago on a Girl Scout Camp Far Far Away. I was the only boy at a camp my mother was counseling with about 200 girl(Pure Heaven)
We had a week of rain and everything I owned was soaked.
Getting Donations from the Girls, I was told to put on the dry Clothes whether I liked it or not, I LIKED IT, I LIKED IT, that was the begin and I still love the Memory and the Feeling
I was also made an Honorary Girl Scout that week!

I Love Scouting Rena

[veronica]

:cute: well....
besides knowing deep inside it would be great somehow.


i was told in no uncertain terms that these items were not for little boys:rolleyes:

well don't tell anyone but they are much more fun as an adult girl



(you understand the term adult is just a referance to physical age and nothing to do with my state of mind)

[linnea]

This is an interesting question to me because I can remember the situation quite clearly, but I can't remember the reason or reasoning. I was about seven years old, so a lot of time has passed. However, I have had a few "flash backs" of memory, especially in the last ten years. These have opened up some renewed memories. I think that the reason for the flashbacks is that my mother died at that time and a few years before she died, she revealed something that happened in her life at the time I was about seven years old--she had another baby. My older brother and I were being reared by her alone, since my dad had died when I was about five. My mother dated a little, but in those days for a woman to have pre-marital sex was still somewhat scandalous. So when she got pregnant, she apparently felt that she needed to keep it a secret, particularly because the father was a married man.
I still don't know some of the details, but I learned quite a bit when the child she bore came into our lives on a quest to find his birth parents. He had been adopted at infancy, so my mother never knew him. NOW BEFORE AN ADMINISTRATOR SAYS THAT THIS IS OFF THE THREAD, let me say that my first "try on" was a Playtex rubber girdle. I put it on and stuffed a big towel into it. Looking back, I think that I was simulating the appearance of pregnancy. At the time, I did not consciously know that my mother was pregnant. My mother actually caught me, and only said, "What are you doing, Johnny?" I answered, "Nothing." She never said another word about it. But from that time on, I began trying on my mother's underwear and eventually whole outfits of her clothes. That was over fifty years ago. In some future thread, I would love to tell more of the story and some of the other influences on my dressing--including the fact that my mother had me wearing girl's panties from very early age until I finished the sixth grade.
So that's part of my story of my first "try on."
__________________

[Jodi]

This made me stop and think. I was 8 years old and the first thing I tried on was a pair of my mother's high heels. Thinking back, I believe it had to do with watching television. THe year was 1953. I had seen a Superman show where Lois Lane was taken hostage by a madman with a bomb strapped to him. He took her out the office window and they were standing on the narrow ledge of the Daily Planet building about 20 stories up. It focused on Lois's high heels and the trouble she was having standing in them on the ledge. She eventually slipped them off and allowed them to drop to the street. I can remember of being intrigued as to what it was like to walk in heels. That evening, I looked in my mother's closet and found a pair of her heels--black 3" slingbacks with a peeptoe and 1/2" platform. I remember them well. I tried them on, walked around in them and noted that I really enjoyed it. The rest is history.

Jodi

[Carlacd]

The only answer i can give is "It was there". So why not. Never stopped since.

[Kristen Kelly]

I can rememberbeing being 4 or 5, and my mom folding clothes bras, panties, panty girdles and slips, the phone rang and it didnt take me long to have the girdle on, slip on over my shoulders and bra on my head. I must have looked funny when my mom cam back into the room. When I was older my room had a closet where out of season clothes were stored (or out of present size I guess too) and there were dresses, shoes, and full slips stored. I would take a pair of panties from mom's dresser and dress in her clothes and look at myself in the full lenght mirror behind the door. I loved the feel of the silk, nylon and the look of lace, and though I purged many times I have come to realize a lepard couldn't change his spots as much as I can't stop dressing.

Clothes are and expression of who you are, girls clothes don't make you a girl, just a man in a dress, the girl is inside of us .

[danielle_from_cal]

I look at photos of myself when I was ten years old and can see that I looked like a girl. And I recall even thinking back then that I loved it when someone told me I looked like a girl.
My mother never wore much for makeup, but I used to wear her one and only red lipstick when I was 14. She probably wondered why it disappeared so fast.
I first tried my sister's underwear when I was 16, and haven't looked back. I can never get over the feeling of femininity.

[Jennaie]

I knew inside why I wanted to wear them. I wanted to feel feminine, I wanted, to be a girl.

[MaylinJane]

I grew up poor in the mountains of PA, and I had to were my older sisters hand-me-downs. No dresses, but jeans, shirts, undershirts, and panties. It wasn't till I went to grade school that I got regular boys clothes of my own.
However, I still continued to wear my sisters clothes on my own.
I'm sure a therapist would have a field day with me:cheeky:

May

[Amanda T]

I was about 10, and forced to try on a swimsuit my parents were buying as a birthday present for my girl cousin, who was about my size. My mother would tell me to stand still, and hold various suits up to me -- right in the middle off the store -- to see how they looked and might fit. When I got uncooperative, my faher took me outside and threatened that he would buy me a dress and make me wear it all weekend. I agreed to cooperate. Then my mother took me into the dressing room, and had me try a couple of swimsuits on, and kept asking me how they fit and how they felt (how was I supposed to know?) All the while other family members were peeking in to see how I looked, while I was forced to twirl around to show the front and back. We bought one of the suits, and I was mortified as we stood in the checkout line -- as the teller was also the sales lady, and knew what went on. Well, we went to my cousin's, and gave it to her. No one ever said more about it, but I kept thinking about it, trying to make it turn out better. Within 2 years I was dressing completely in my mothers clothes whenever the whole family was gone, and seem unable to shake the attraction to this day. Finding so many other people with the same attraction (for whatever reason) has been a big help.

[nancy58]

I was pretty sexually repressed when I was a teenager. I wanted very badly to make love to a girl, or really just to touch one, but that was out of the question because good Christians don't do that, do they? So once, when the rest of the family was gone, I tried on my mother's bra, and the rest is history.

Nancy

[Steph]

my sister and her friend forced me, and I loved it.

[marciegirl777]

I knew from early on that girls clothes had a strange attraction for me. I wished I could wear cotton panties like the girls wore. I didn't understand until one day I went on a trip with our neighbors who had a 11 year old girl among their siblings. I was alone in the bathroom doing my thing and I saw her swimsuit hanging over the tub. The attraction was incredible - it was almost as if it was calling out to me "try me on, you'll look sooo cute!" I was 14 at the time and much too big to fit in her swimsuit, but the image and desire to try it on was powerfully seared in my mind. Twenty years later when I married, the same attraction overcame me again. One afternoon when I was alone, I was I pulled out my wife's swimsuit. I remember I was almost shaking; wearing a woman's one-piece swimsuit just seemed as taboo as they come. But when I looked in the mirror, I nearly "melted" with pleasure and delight at seeing myself looking so beautiful and attractive. I finally knew then that this was a part of who I was.

[maid phylis]

i can remember when i was around five years old i used to play in my parents bed when they were out at work.for some reason now forgotten i put on my mothers nylons and this was in the 50s when women wore nylon stockings,once i had put them on i was forever started down the merry road of being a crossdresser ,and why i did it that first time ,maybe it was meant to be .and i am glad that i did it. :love: :doll: :jumping:

[Siobhan Marie]

I tried on a pair of my mum's panties when I was small (can't remember how old I was) and knew that it felt good and couldn't understand why. As I grew up I had lingerie around me. It was only recently that I realized that I am a crossdresser that needed to dress fully. I had accepted that I needed to wear panties, nighties and other items of lingerie 24/7. But I must say that I feel so much better having found the Anna side of me.

:hugs: Anna x

[Robertacd]

I remeber the first time I noticed one of the girls in my class was wearing a bra. I thought to my self "I should be wearing one too". Wasen't long before I tried on my moms bra and panties. It just felt so right, and that feeling has never left me.

[Lawren]

Hmmmmm. Good question. I aiways thought of it as just plain curiosity but now I wonder why I was so curious in the first place. Was it because I had three sisters and only one brother, who was away at a private school when I started CDing? Was it because I was not popular with the girls at school? Or because I just liked the way dresses looked on girls? I really don't know. I had good relationships with both Mom and Dad so that probably had very little influence.

Well. Enough rambling. :D

[Jennaie]

Honestly, I think what made me try it on was that I was hoping after I had it on I would look like a girl.

[Laurie Ann]

It goes back to age 4-5 with my aunt dressing me up as a little girl. Dress, ruffled panties, anklets and patent leather mary janes. It felt right then and still does.

[jenny_cheerleader]

It was when i was younger, maybe 5th or 6th grade. my sister had this huge dress-up trunk with all sorts of 80s stuff. i used to see that stuff and something in me just thought, why not try it on. so i tried on this red dress she had and even though it was a little too small, i thought "this is wonderful" i wasnt able to do much more than that until ebay and my later HS years, but now that i have my own place, as soon as my income stabolizes i will order stuff!!!

[Kate Simmons]

Girl's clothes were always prettier than boy's clothes. That's why I liked 'em. Was kind of a "no brainer" to me. Ericka

[ava_bruna]

Hi Hon, I myself started I think by looking in the Sear's catalog see all the undie's and wondered about how they would feel, I was perhap's 10. so being alone once I looked in my Mom's drawyer's and found her undies and felt the urge to try them on.I enjoyed it very much but it really didnt impress me all that much till my later year's, after I married a few year's after I started wearing my wife's pantyhose but they were to short so I got some of my own, then a bra next panties ect, so have been dressing over 25 yr's now and love it so much, I just wish *I could do my nail's and makeup more:( butjust cant in our new situration. im sure most of us started out pretty much like this. huggie's, Ava.

[Gurly]

I was always keeping an eye out for the Sunday paper's supplements, which almost always had some women's underwear ads in them. I was very young, so I had to be sneaky about it, as I had older brothers and sisters. For some reason I was fixated on bras and eventually starting wearing my mother's bras and open-leg girdles. It eventually developed into full dressing and I wouldn't give it up for anything.

[Helen MC]

Even as kid I found girls' and women's knickers (panties) had a great attraction for me and whether I was looking up some girl or woman's skirt or saw them flapping on a washing (laundry) line, or displayed in a shop window or piled up with the laundry at home I got a thrill and tingling sensation which I now know was sexual.

I started to have the urge to wear a pair of girls' knickers (full cotton briefs) instead of the Y Fronts I then wore like most other boys of my age then. Eventually just about the time of my 12th birthday in 1965 the circumstances were right one day and I took a pair of my 14 year old sister Anne's knickers and tried them on. WOW! They were just a pair of white cotton interlock briefs with elastic through the waist and leg bands and a double gusset, but to me they were like the Golden Fleece. Not only were they far more comfortable to wear but the thrill of so doing was fantastic! I wore them under my trousers for the rest of that day. From then on I secretly shared panties with my sister on all days except when I had to do PE and Games at school and when I ditched that subject which I hated anyway when I was 15 I wore panties 24/7 and have done so every since. The rest as they say is my personal history.

[melanieee]

I remember mums black nylon full brief panties.Dad had come home from an overseas trip with several pairs of Panties.This was about 1965. One pair had a target on the front with the words''your target for tonight'' The other pair said 'hands off'' I got a transistor radio,which was cool,but I was more interested in the panties.
They were like nothing I had ever seen,and awakened an interest in lingerie.I used to track them through the house,in the laundry, out on the clothesline, in the drier, back in mums lingerie draw and around again.
Dad was at sea and when Mum would go out for a evening, I would sneak into her bedroom and put them on.What a great feeling!!
I progressed to other Items, longline bras,and panty girdles,slips etc.(as you do!)One girdle had roses embroidered on the front with 4 loops for stockings.I htought it was the most arousing garment to put on.
I envied her for the nice things she had to wear.Some times I would be asked to do up Mums zip on the back of her dress,dad as sea,and I loved being in the bedroom as she got ready.She would put on her stockings in front of me,I tried to make out I was not too interested in the proceedings.
Maybe she suspected something........
Im more into lingerie than going wigs and makeup,though I did go to a dressing service once,and enjoyed it very much.I looked like my younger sister,Mel,so thats my name.
this is my first reply, this is a great place, it feels like home,I can be me here and not be judged for my fashion and taste in lingerie.

[redsatinmaid]

My first time I was 12 and they were my babysitters nude pantyhose she wore to her graduation. She looked so sexy and I wanted to feel that way. She moved in with us temporarily and I was always in her room while she was gone trying on her panties, dresses, and pantyhose. I;ve been dressing ever since.

[VERONICARH]

I remember the first time I tryed on my mother's girdle and stocking after I had taken a bath . It felt great but did not understand why. Been doing it every since. I think I was around 11 or 12. Veronica

[cdgirl]

Besides what item we first started with, I often wonder what gave me the curiousity to try it on in the first place. In my case, nylons. It's not that every boy thinks to do this, so why did I?

Anyone else wonder why they thought to experiment in the first place? Had I/we never tried this, would I be a crossdresser today. Was it simply meant to be?

Julia hi julia at age 12 went into my mothers dresser draw put on her seamed stockings bra and girlde.and then it began and then i never wanted to remove them.don't ask why i went in there.but im glad i did.

[Tina Dixon]

I just remembered those two layered nighties from the sixties, my mother had one laying out and just stood there looking at it, next thing I knew I was naked puting it on, the rest is history.

[ShortSkirt]

I don't remember why I did the first time. What I do remember is, I was 7 or 8 and standing infront of my mothers dresser very nervous and excited. I remember the white bra and girdle in the drawer and how scared I was. The part that I remember most, was after I had it all on, I just totally relaxed. It just felt so....right. Not really sure how to explain it, but it was and still is, a very powerful feeling. I still feel that elation when I'm out dressed.

[Jerry]

I was about 5 and at the neighbors house playing. We started playing dress up. (That was before today's kids dress up boxes.) I put on the girls tights, a red plaid jumper, and mary janes. After that I kept going over to their house.

Thanks, neighbor!

[sally angora]

I remember the first time I saw my sisters new angora cardigan , I knew it was special and something inside of me just clicked....I wanted to wear it.
I was very young at the time and waited until after school when no one was home , snuck into her room and tried it on , the feeling was so wonderfull.
from there it was just a progression to wearing all those other delightful feminine clothes. What prompted the attraction I have no idea , but I am glad something did!

Sally

[Jemanda]

Curiosity made me experiment at first, I had no sisters or close female cousins of friends so I suspect it started at the bottom of my mothers wardrobe where her old wedding shoes were, I was always curious as to how it was to walk in them, then I suspect I wondered about the rest of her clothes, what did a skirt feel like and why were her undies different, gradually experimenting with individual items of her clothing (which didnt fit because he was much shorter), at a point I no longer fitted in her stuff so had to grit my teeth until I could go out there and get me own. I also wondered about the girls in the primary school I was in, why was their uniform different to ours and wh7y did they get to wear such nice mary janes with anklets and I couldnt! My first purchase was a pair of wedge heeled sandals and after that it became a regular obsession to buy something new to try on. Numerous purges later I am still at it! (now I want one of those flared skirts...)

[HaleyPink2000]

Yeah, I wonder all the time. " Why "???:happy:

[Nicole Lee]

I first tried on pantyhose to be like the wrestlers on TV with their spandex tights. I soon evolved to spandex tights, and then started wearing more and more female attire and now it's an unstoppable addiction! ;)

[ginafaye]

the earliest was my mom hadme wear my sisters panties .iwas about 5 or six and it was a hand me down thing underwear was just underwear to my mom. later as she took in sewing iwas the dress dummy........never gave it much thought untill puberty and i experminted a little with moms and my sisters things . didnt do much more till after a long time ......after the army and my first marriage. but about ten years ago i wont bore you with the deatails my wife and i discovered or reawakened this side of me and ive been dressing ever since

[carolynn]

i was 14 when i tried on mt first pair of stockings.me and my mum had been to a wedding and when we got back home she went up stairs to change.she left me alone to visit a friend.i went up stairs in to mums room looking for something cant remember now wot it was now but i saw a pair of stockings and suspenders on the bed i kept stareing at them and had a powerfull urge to try them on and i did just the feel of the stockings blew me away.i am now 44 and the same feelings i got back then i still get now.i have no regrets.

[maid phylis]

for me it was also nylons and i tried them on when i was five years old.why i dont know but from then on my life changed .love phylisanne:love:

[Gurly]

Well, I remember my sister trying one of her skirts on me when I was around 4years old or so. For some reason it felt very good, so I guess the desire was in me at an early age. Soon after I was attracted to my mother's bras and from then on I was "hooked".

[avawho]

Looking back on it, even as a very young child I was already quite aware that I was different and couldn't understand why adults didn't treated me as one of the girls... took ages to sort that one out... The first thing I ever tried on was a pair of my mothers high heels, as they were in the pile of shoes at the front door, it just seemed the right things to put on that day...
the rest was history

Cheers
Ava

[keeley]

for me it was a pair of red silky knickers in my early teens. I just wanted to know what they would feel like. From there I can't really remember what happened next or when I tried on a bra and any other items. I guess I just wanted to know what I'd look like as a girl so for me the knickers didn't start that but if I hadn't tried them on and enjoyed the feel so much maybe I wouldn't have tried anything else.

[Olivia]

When I was 13 my family moved to Geelong, Victoria, Australia for my dad's job. I can still vividly remember the "first" for me although it was now 40 years ago. My bedroom was an addition and somewhat isolated from the rest of our house. For some reason, still unknown to me, I decided to try on one of my mother's bras. She was a buxom woman and of course, the brassiere was way too big for me, but that didn't deter me in the least. I retrieved one from the laundry room and in the privacy of my little room I tried it on. Oh, I can remember how exciting it was for me both mentally and physically. My reaction was immediate! I was hooked (you'll pardon the pun of course, lol) and from that point on, whenever my parents were away I was in their room trying on various items of my mother's clothes.

I developed the stealthy instincts of a cat burglar; learning to try on clothes and carefully replacing them exactly as I'd found them. In fact, I began to pride myself on that ability and my technique. I waited until they'd been gone at least 15 minutes before venturing into the dresser drawers and developed a "sixth sense" on how long I could stay dressed before they would return. This continued after our return to the States and all through the years that I lived in their home. To this day, I really don't believe my mom ever discovered anything amiss with her clothes. Oh, I was good, haha. No crossdressing mission was impossible for me!

I know now that I am what I am and was probably that even before the event happened. I would not change that if I could, believe me. Now, I'm blessed with a loving, supportive wife(of 29 years) and two accepting, grown children too. I stay dressed 90% of the time whenever I'm at home and wear panties everyday beneath my male work attire. I can think of a couple incidents from very early in my life that might have been catalysts for my crossdressing but that is just armchair psychology at best. The "why" doesn't matter that much to me now; that seems irrelevant at this point in life. More importantly, I am very comfortable with what (and whom) I am and look forward to many more pleasurable years being Olivia.

[medias35]

The very first thing that led me to the wonderful world of dressing, was nylons. My mom's friends would come over, they would sit at our dinner table and talk. I would always sit under the table and rub thier feet and legs. To make a long story short one of her friends probably wanted to cure my curiosity, because one day she asker me if I liked how her stockings felt. Before leaving she went to the restroom and came out barelegged. I went to the restroom after she left, and was in uphoria. I was only 4, 31 years later I don't go a day without sheer-to-waist pantyhose.

[KimberlyS]

Julia, I have often thought of the same question in the past. While growing up I did things with my Mom, but not any girly things. Just helpped with things in the kitchen and around the house. And I did things with my Dad and enjoyed doing both of them. While growing up I had both boy and girl friends. I do remember when growing up my Mom, if we were going out some place dressed up, would be getting ready in our shared bathroom wearing PH, bra, and slip as she did not want to get her clothes dirty while getting ready.

But what made me pull that first bra out of the garbage when I was about 8-9, I really do not know. I tried it on and then purged it. Then several years later i pulled out a bra, panty and PH out of the trash. I had those for a couple of years before purging them. Then a few more years later it was on to the things in mom's drawers.....

But what made me pull them out and hide them until I can could try them on I do not know. That is a very good question.

I have never felt like a girl or girly, even when I am fully crossdressed. I have never felt like a macho man even though I do many macho male things. And as long as I can remember I have always just been a male with a mix of male and female attributes and characteristics.

So I am just a guy that likes to wear feminine clothes at times because that is who I am.

KimberlyS - CD

[rachelusissy]

i was around 5 or 6 i can remember watching a show on the tv and a girl in the show was wearing a pretty pink cardigan and mini skirt and i can remember thinking when i am a big girl i`m going to dress like that but i did not wait untill then,i got dressed in my sisters similiar clothes 5 sizes to big.

[myMichelle]

How did I get started?

When I was six years old, there was a woman who lived next door. This was back in the early 70's, and one day, while I was over at her house, she threw away a pair of white go-go boots. I really liked those boots! I liked them so much that I secretely dug them out of the trash can, and tried them on...I can still remember that they were size 9M. They were actually a cuople of sizes too large, but I wore them anyway. I used to sneak off into some nearby woods and wear those go-go boots for hours on end.

Growing up, I used to tell myself that just because I liked to wear women's shoes, that did not mean that I had any interest whatsoever in wearing women's clothes...I suppose that made me feel like I wasen't so "different" from any other boy. My world got all turned around when I was in college and I began to realize that I did, in fact want to start wearing more than just shoes. The rest, as they say, is history.

[Julia Cross]

Hi everyone, thank's for the many insightful responses. It would appear many of us don't know why we tried things on other than we just thought they looked nice or felt nice. Perhaps when we were younger, the boundries were not so strictly engrained in us as to what is for women and what is for men only, so natural curiousity played it's part. What made us continue and others not, that is something I am still trying to fully understand.

Julia

[Jamie Coffee]

there was a boy in my second grade class who dressed as a girl for holloween and I have always thought about that and I wanted to try it one year for trick or treat and have been doing it everytime I get the chance

[Sky]

In my case, first were my mom's panties. Then her nylons. Then her shoes... until they didn't fit anymore.

And it was a bit more than curiosity, I wanted to be a girl. Can't say I succeeded at it, but it sure wasn't for lack of trying!

[Angie G]

Besides what item we first started with, I often wonder what gave me the curiousity to try it on in the first place. In my case, nylons. It's not that every boy thinks to do this, so why did I?

Anyone else wonder why they thought to experiment in the first place? Had I/we never tried this, would I be a crossdresser today. Was it simply meant to be?

Julia
It was so long ago it don't come to mind but i know I liked it

[Robyn2006]

Plain and simple, it was watching my incredibly gorgeous older sister put on her lipstick. She's 8 years older and so many of my earliest memories are of sitting there in our bathroom talking to her while she got herself all dolled-up, glammed-out to the max, driving every guy in the neighborhood nuts... I just knew inside that I had to be able to do that too!

xxxooo,
Robyn

[Glenda]

My first time wearing women's clothes was during a "Prom Dress" theme skate with a group of roller bladers. A couple of months after that my girlfriend at the time wanted me to dress as Mrs. Doubtfire at Halloween. She went as Ross Perot. Ever since the first time I saw myself in the mirror in make-up and wearing a wig I knew that it was something I was meant to do. My girlfriend even commented, "My God Glenda, you look so natural as a woman." Hence my name and my passion.

I knew I thought differently from my brothers and friends while growing up but never dreamed of dressing as a woman.

[Claire_CD]

What got me started was my neighbour.
She was divorced, but had one daughter that I knew since I was 1 years old.
When I was 10 my brother was born and he had to goto a specialist for his heart problems, because I'd get in the way, my neighbour looked after me for 2 weeks.
During that time, I had got drenched in the rain and had nothing to change into as the rest was in the wash (even my nightwear), so being there are no male clothes in the house I had to change into a skirt and small blouse type top as the girl was 2 years older than me, she found it funny and suggested I wore some tights, It felt awsome and I said liked it, I had fun the rest of the week by dressing up in all sorts of clothes, I am now 19 and still go round hers to do it as my parents would go mental on me if I did it at home.