Why did we start?

[Jackie C]

I am curious about how all you gals started in the fabulous world of crossdressing! My first experience was pantyhose, of which I still have a huge fetish! This occured when I was around 7 or 8 years old, when I snuck around wearing them as much as possible. I never got caught wearing them, but my mom did find an empty No-Nonsense package in my bedroom. She really freaked out! In my late teens in evolved into high heels w/ stilletos being my favorite. Then as I hit 25 it was all the way baby: Wigs, makeup, hose, heels you name it. My only wish is to be a little shorter, (I'm 6'3"), and a little thinner. (yes I'm working on that too :cheeky:)

My first reaction to womens clothes was comfort, just love the feel of all those frilly things on my body. It still is very sexual for me...an extreme turn on.

Sorry this is so drawn out!

Kisses!

Jackie

[Shelly Preston]

I think it was being in the house alone and exploring.

When I found my motheres stockings well it just went down hill from there.

And I love every minute of it.

[Nikki Dee]

Mom's underskirt and stockings at about the age of 11/12...nothing seemed the same after that.!!!...know what I mean.!!!!!!!
Nikki. xx

[davine]

Hit puberty at 13 and suddenly the urge was there. I loved the silky feel of fem clothes against me still do though now it is less sexual as I like to explore new looks. That was 43 years ago.
D

[stuart]

I have been dressing up in women's lingerie since I was about 7. I have been married for 10 years and my wife has no clue. How do I tell her? Should I tell her? Does anybody have words of wisdom for this fellow cross dresser?

[Kimberly]

Always had a fascination.

Something that will stay with me forever: I was once round a GG's house, friend of mine, we were about 5 - I was trying to put on her white shoes... you know, t-buckle styly... she was trying to stop me. "They don't fit you.... they're not meant for you..." Those kind of transophobic comments.

Lol... it's been a long time. But I've always loved fem shoes. :) xx

[ERIKA1963]

I got started when I was about 8 or 9 my cousin was the same age a me was wearing a pair of shoes that had a little heel maybe two inch or something like that we were playing for awhile running and jumping she took off her shoes and went in the house to go to the bathroom and I tried them on and its been heels for me baby ever since. If I could dress alot more I would but we all know how that is. ERIKA1963 :o

[maid phylis]

I have been dressing up in women's lingerie since I was about 7. I have been married for 10 years and my wife has no clue. How do I tell her? Should I tell her? Does anybody have words of wisdom for this fellow cross dresser?
dear sister i have experience in telling ones wife,all i can say it took me 34 years to finally tell my wife and i was so relieved that she accepted me for who i really am,my advice is if you have small children or none at all then try to tell them sooner than later so you will know that she really loves you ,i know that this is a big decision but it nearly killed me not being able to tell her so many times.well good luck your sister phylisanne:doh:

[Aileen]

I started when I was 11. My parents were away, and there was a babysitter downstairs. I tried on a colorful dress of my Mom's, which turned out to not be a dress but a romper. I stuck two small baseballs down it, but no bra. That was all I dared to do at that time. Later it was lingerie and pantyhose. You know, I never figured out how to masturbate successfully until I was 20.

That's how I started. As to why I started: I started because I'm a crossdresser.

[kristytv]

not to make this a saga, i was dared to dress up like a girl when i was oh 11-12, i did , and i loved it, i kinda puzzled my friends, but it felt right and wondered why i wasnt born this way , it was electric , the begining of my sexualitly and all, and here i am, it also led to some things that are not so clean to talk about here

[trisha_anne]

Growing up my mother always kept her dresses in my bedroom closet because hers was full with everything else and all my clothes went into my dresser. Anyway one day when I was 13 I stayed home from school for a reason I forget and the temptaion was too much they had always been there but it was like they were calling to me. I was all alone, so I put on one of her dresses and pranced about the house. The more chances I got the more I started adding on until finally I got the courage to get all dressed up in a dress, pantyhose, heels, and make-up and it has been in my life ever sense.

I have actually told my mother this and she laughed and said, " At least someone got some use out of those old things"

[CarolDonna]

I was around 14 when I tried on one of my mother's dresses that I found in a trunk.

It may have happened much, much earlier though. I have a distinct memory of being around four years old and trying on "shorts" I found in a linen closet. I've often since thought that they probably were my mother's panties. I never saw her wear shorts in my life.

Carol

[Laurie Ann]

The story is too long to go into here but suffice to say it started when I was 4-5 years old my aunt would dress me up as a little girl and take me out. Why I have no idea but its been in my mind since then.

[AprilMae]

It was cheaper than learning to play golf.

[Lilac]

It started when I was around 8. My cousin tried to humiliate me and dressed me up in a nightgown. For some reason, it felt right. After that, it went to bathing suits, then bras and panties. Now I'm wearing outfits, dresses, and even costumes. I eventually want to try wigs, pantyhose, and eventually shoes.

[Darlena]

Seven seems to be the magic number. If not that, then twelve. I was seven when I went for the dressing up gig.(in front of others) Then twelve when I more outwardly expressed my innermost desire to be a girl (participatory). I suppose we have our own demarcations of that eventful influx in our personhood. None the less..,we all found fit at some time in our lives to be outted to our own private selves. Then the matter of the public...I found that to be when I was 20 or so. I've never looked back since. Love & kisses,

[pauleen]

I started around 5 or 6 wearing my sisters shoes ,then progressed to panty hose I just loved the soft feeling they made on my body ,and of course my sister loved high heels ,"little did she know I loved her heels too"16 yrs old I started wearing dressesI only had one 18 through my 20.s I went dorment for awhile ,then in my late twenties I went back into it full force and never looked back ,but I,m still in my closet ,thats another issue ,and another story .

[Natalie]

i started young, i remember trying on my mom's shoes when i was maybe five, and it went from there. sneaking dresses that my sisters outgrew and just moving onto lingerie and everything else.
i love stockings the most at first, then panties and bras.
of course as soon as i moved out, i was wearing nighties to bed and panties every day. i now own several pairs of shoes, even thigh high boots, a few dresses and tons of panties.

[Angela Burke]

The first vivid memory I have is being at home during school holidays aged about five wearing a white blouse, a cardigan, a pleated grey school skirt, navy blue knickers, white ankle socks, and strappy sandals.
My memory is vivid as it's a memory of an old b&w photo. I don't know what happened to it, I've looked through all the usual family photos and there are a few of girls of about that age.
I've consulted with my sisters but sadly none of them are me.
But I did find out from my sister June that although it was her hand me downs I was in, I was wearing my own knickers.
This was how I first found out about my Mothers rule about everyone wearing their own (nametagged) knickers.

[EjayeCD]

When I was around 5, I didn't have any boys my age in the neighborhood my age & the older boys didn't want a little kid around, so I played with my sister & her friends. We played all girl games including dressup in girls clothes. I got hooked & never stopped dressing. When I got older, I just loved the feel of the underwear, dresses & skirts.

[Helen MC]

Trying on a pair of my big sister's knickers (panties) when I was 12. I had found these lovely garments fascinating for a few years before that but it was then that I first had the urge to wear them and have never looked back since, wearing female underwear instead of male ever since. This led in time to my wearing her skirts, bras, blouses etc and later my Mum's as well when I was alone at home.

[DawnRodgers]

Well, at first, curiosity. Loved the look and feel of ladies things so it seemed natural ro try them on. It had the desired effect. It looked good, felt good, and it led to self satisfaction. After that it got easier and more desirable. Guess we train ourselves in a cause and effect manner.
As I got older, I got more elaborate, got a few items mtself and before O knew it I had a complete wardrobe, about 6 pairs of shoes, lingerie, a wig, jewelry, pefume and breast forms. After a while it felt more comfortable than wearing mmen's clothing, certainly was sexier amd felt like I wanted to dress that way for the rest of my life.
Dawn

[ocxdresser]

Many years ago my ex gf whom had been living w me moved out abruptly...and neglected two loads of laundry (one in washer one in dryer) in her hurry to leave....she never asked for/about them and all the sydden i had a fairly good sized wardrobe...its been sheer heaven ever since .....if she could only see me now ...!!!!

[GypsyKaren]

I remember wearing my mother's nightgowns when I was 5 or so, I also used to get into her lipsticks. I started serious dressing when I was 11 or 12, I really don't remember why. I found a pair of stockings and put them on, and that was all she wrote, I was hooked. Switched to pantyhose when they first showed up in my step-sister's drawer, I was 12 or 13 then, and became instantly and totally addicted to them. I've been at it ever since, and since I'm out of the closet I wear them everyday now.

GypsyKaren

[Lois82]

I guess I was about 11 when I tried on my sisters panties but actually got hooked when I was 18 and in my own apartment. Thanks sis :clap:

[Foxy Lady]

I went to Catholic school and in fifth or sixth grade the nun caught a couple of us boys picking on a couple girls. She said we would be punished the next day. Next morning she took us boys to an empty room and made us put on skirt and blouse and wear them all day, I was hooked.

[susancheerleader]

Gorowing up I had two sisters and we were all a year apart, so we didn't have much of an age difference.
When I was about 11 or 12, they started gymnastics. I loved watching the girls in thier leotards. One day when I was home alone, I took one of my sisters leotards and put it on. I loved the feel of it, and would always wear it under my clothes, or to bed.
I kept getting caught because my sister or mother would come in my room for something, and there I was in a leotard. I'd get yelled at and have to give it back, but soon after, I'd find another one and repeat the whole deal.
I gave up doing that a yer later, and didn't ever try on another girls item again. Until last year when I remembered the feel of the leotard and that was 30 years ago. But I bought one anyway, and instantly loved it and bought more. I also found a love of cheerleading items (hence my avatar) and mini skirts, tights and panties, and... and ... and.......

[Ellaine]

Hi Jackie :) That's the toughest question of all!! So "Why" has become translated to "how".

And only Alan has answered the question. ;)

Too tough for me, though. I know I was suddenly taken over by a mysterious force. I'll never know why my Mothers stockings suddenly had to be slid onto my skinny ten year old legs, (not a pretty sight!). Nor will I ever know why it was terminal. Past caring why. lol

Hugs Ellaine.

[MelindaC]

Curiosity, at first, I think. I know for sure the need to dress female had been with me since I was very, very young. But it wasn't until I was 11 that one day I had an overwhelming urge to try on one of mom's Playtex rubber open bottom girdles. Once I figured out how to get it on properly, I was completely hooked. But something was missing --- a pair of stockings to wear with it. So I found a pair of stockings, put them on & hooked them up to the garters on my girdle. Now I felt even more feminine.....

And more curiosity led me into slips, bras, dresses, heels, etc........ that plus feeling more comfortable dressed en femme kept me going......

[livy_m_b]

It depends on what you call crossdressing in part at least. when I about 4 there was a box of high heeled shoes in my closet (I think my mother's sister had given them to her) and I remember wearing them and enjoying it.

Then, my mother's dresser had powder, Jergens Lotion, earrings (screw down type), a few costume jewelry necklaces, and I would sometimes try those.

Then, about 8, a friend from a block away and I dressed in his mother's dresses and stood out on the front porch of his house en femme.

Then, about 13, a neighbor moved out of an apartment near us and stored her clothes in our basement - it was late 50's and there were skirts, blouses, etc. - I would wear some of my mothers bras and those clothes.

It's been downhill from then.

Why? I strongly identified with my mother - I was said to look like her - but I tended to engage in other gender-specific activities available in the 50's - embroidery, house cleaning, washing, ironing, sewing, baking, cooking - why did I do those things? I can't say - I just did them - it's only gradually that I was able to draw the conclusion that my gender identification was feminine....

[kaliope]

It all started with my neighbor's dr scholl sandals. She wore them all the time with tan hose. I was 14 and we lived in an apartment building and she would leave her sandals outside the doorstep. I tried them several times and I decided I had to have a pair. I saved my money and bought a pair at the local drugstore and wore them in secret with my sister's pantyhose, Then I don't really remember what happend but after my first girlfriend I stopped. Then I got out of college, got the urge so I went out bought a pair of black scholl sandals , tights, knee highs and and demin skirt and went to my first TV bar. I haven't look back since...I love la Perla lingerie, it's a great treat.

[Amanduhrob]

The why I believe is because I had a cousin dress me pretty regularly while she babysat her sister and myself, that was from ages 7 to 9.

I started dressing myself around 16, and thou I don't dress often, I do go all out, with the exception of breast forms, which I'm considering now.

[pammiecd]

I remember a dress of my sister's that had a smell was so sweet. I was only about 4, but I used to put it on, or just sit and hold it. Later, when I was about 13, I found a bag of her old nylons, and I was in heaven, and hooked since. As far as telling your wife, I was succesful in hiding it fir about 3 years. At that time we were working opposite shifts. One afternoon, I left some things out in the open, she found them when she got home from work. She confronted me, she thought I was cheating on her. She was actually relieved when I confided in her

[Girly Sara]

I tried on my Mum's panties when i was around 13 years old. There was no turning back after that experience.

Sara xxx

[Dragster]

Like MelindaC, I became so fascinated by my mother's hook-side open-bottom girdle when I was about 10 or 12, that I felt compelled to experience what it was like to wear it. It was so tight on me, and the pressure on my stomach and my penis felt really great. At the time, I didn't know why it felt so exciting when my penis hit the floor as I did press-ups in it on, until I had my first (accidental) orgasm into it. Boy did I panic that I couldn't clean it and dry it before she returned! When you have an experience like that, what do you do? Repeat it of course, but with more care, and 50 years later, I'm still doing it!

Also like Melinda, I progressed to stockings, bra stuffed with socks, slip and dresses (shoes didn't fit) whenever I got the chance.

Tony

[lela]

I've aways known that I was different. I dabbled into trying my mothers dresses and shoes on when I was 8 or 9 years old. I'm 57 years old now, so back then, being interested in girl things was taboo. I remember being jealous of the girls I went to high school with, I always had the urge to be one of them. The urge to dress was always there, but I didn't really start to explore it until I was well into my marraige. I had an aunt who knew of my desire to dress that helped me a lot. I would spend Saturdays with her learning about fashion, makeup and hairstyling. She was much older than I, and she was a very refined lady. When I came out to my wife, she couldn't believe the knowledge I had on women's fashion and makeup. She supported me and thanked my aunt for helping me be myself.

[TGMarla]

Though there may have been some kind of curiosity element prior to this, I started because of an "ugly" contest in Junior High School, the 7th grade, during homecoming. I had had the idea that if I were to put on a pair of pantyhose, and cut flaps in it that hung down, it would look like flaps of skin coming off of my legs. You see, I really didn't know how any of this worked at that time. My mother told me that that really wasn't going to work that way, but since I was in my early teens, I knew everything, so I insisted.

Well, it didn't work that way, and I had to bag the idea. But the feeling of wearing hosiery was absolutely electric! And things progressed from there. Oh, and I came in second in the "ugly" contest. Some other kid put tape and axle grease over one of his eyes, and looked absolutely hideous.

[Robertacd]

I think I was in 4th grade when I noticed one or two of the girls were begining to wear a bra regularly. I remember thinking I should be wearing one too. Soon there after I was home alone and tried on my mothers bra and panties, took one look in the mirror, everything just felt so right and the rest as they say is history...

[TracyDeluxe]

I think I started because I always had that core feminine gender identity. My very first memory of wanting to dress prettily was when I was very young, certainly under 5, probably more like 3 or 4 (if we can remember that young?), anyway, my mother had bought the prettiest pair of frilly blue panties for a friend's little girl's birthday, I guess, and for some reason showed them to me. I asked her if I could have them, and she told me, "No, these are for little girls, and you are a boy." And I remember saying that "Well, maybe someday I'll grow up to be a girl, too." I swear to God that is a true memory.

To make matters worse, I had literally no male role models in my formative years (my dad was traveling the world at that time, working on big construction projects), and my mother and I lived with her sister, and her 3 daughters, all older than me. I was immersed in feminity, but though I begged them to dress me as a girl, they only did once or twice, and then laughed at me, not what I wanted at all! I soon learned to hide my desires, and to think of myself as "bad" for wanting to dress and be a girl, and it has taken years and years to become fairly accepting of myself, and to live as a woman 24/7. There are still times when I look in the mirror and hate myself for being the way I am, but thankfully those feelings don't come too often, anymore.

http://static.flickr.com/32/99667254_af75a4683a.jpg

As I sit here typing this, my heart goes out to all little boys who want to be little girls.

[KarenNY]

I think because my mother was such a huge influence in my formative years -- my father had split when I was about 5 -- I sort of idolized her growing up and wanted to be like her. I actually also remember being in kindergarten and really noticing the dresses that girls got to wear, and feeling sort of jealous. When I was 7 or 8 I started getting into my mother's clothes, starting with her outer clothes (dresses, skirts, blouses) and things snowballed from there. By the time I was 11, I was dressing in pantyhose, lingerie and her outer clothes -- she worked for a financial planner so she had all kinds of really nice dresses and skirt suits (it was the early '80s by the), so I liked to dress up just like her and pretend I was going to work too! I did this behind her back (I was a latchkey kid from fourth grade on), until she found me out when I was in seventh grade. Then she got me my own girls clothes so I would stay out of hers (and they were more appropriate for a teen girl)!

[Amelie]

For me, it was sexual but in a different way.

I was having sex with guys, mostly older guys when I was in my teens. No, these guys didn't force dress me. But they did have a way of treating me like a girl. I have seen how guys treat and talk to girls and these guys would talk to me in the same way, sort of like some people here on the forum say that others mistake them for women when in drab. It was quite a few guys who treated me in this way, I was very confused, sexually,, and gender wise. These guys played with my inner emotions, in some way I was uncomfortable with who I was.

These guys saw a girl, so I became this girl that they saw. I first became a girl on the inside of me and then changed my outward appearance to look like a girl. I was no longer confused, well I still have questions, but I have been happy ever since I became a girl.

[Marie CD]

All of you seem to have know at such a young age. i was in my early 20's when i started putting on my wifes clothes and i use to sneak her make-up to. I'm divorce now and she still doesn't know that i dress. i just wish i would have accepted myself when i was still in my 20's . I'm 41 now and regret the years i have lost trying to deny who i really was.

Live life to the fullest, for it could all end tomorrow.

be well all
marie

[madeline]

For me it started at age 10 with was my older sister's ballet tights, leotards, and pink leather ballet slippers and pointe shoes. I would sneak stuff out of her room during the day and then at night, when I was alone in my bedroom I would excitedly dress in my girl things. It felt so wonderful and relieving to be able to dress as a girl. My dressing experiences soon expanded to include her panties, bras, and nighties. I would dress and then fall asleep with them on. Finally after about 2-3 years I was trying on her dresses and shoes (strappy sandals) and completely dressing as the girl I knew I was.

[Alystin]

For me it started when I was 10 or 11. My parents were going through their divorce and my mom was staying with her parents. My brothers and I would spend a night in her bed, seeing as though my dad always slept on the couch. Then curiousity got the better of me and I started trying on some of her things. And it cascaded from there. Once she moved back in, I would sneak in and borrow her clothes, I didn't really focus on anything in particular. And take them back to my room to wear throughout the night. I always felt more comfortable sleeping in her night gowns and slips then in my own pjs. Wearing her clothes just made me feel more like myself, or at least who I was suppose to be.

[Victoria Pink]

I started at age 5. I was "drawn" to my sisters pink panties. The color was wonderful and the material was soft and silky. One day sis and my cousins were playing dress-up. I was watching them strip down t their panties as they changed outfits. They invited me to play with them. I jumped on the opportunity. Went and put on sis's pink panties and then came to where they were playing an put on a red dress and high heels. I don't think they expected that and went and told my mom and aunt. I got into trouble over what I had done.

However, I never forgot the excitement of the panties and it continued from there. Today, I often dress. My wife is supportive and realizes my need to do this.

Victoria

[the475574]

my first experience i remember was at maybe age 3 or 4 i started wearing my moms makeup and wearing her pantyhose and shoes. then in middle school i went to a catholic school and they had a room were they kept uniforms in one day i got the bright idea to tell them that i needed to buy a boys uniform so the lady told me to go down to the room and find clothes in my size. but when i got in there i tried on the jumpers and then the skirts and blouses untill i found one that fit me and took it home with me. if the lady at the school knew anything she never said. My first trip out in public was on halloween (the best holiday!) when i was in high school I looked so much like a girl that everywhere i went i was referred to as ma'am misses untill i opened my mouth and started to talk and then it was almost comical to watch the peoples faces and reactions. i havent been out in public recently though because i no longer have a wig and i dont have much money
but my natural hair is almost shoulder length so maybe i will go out some more soon

[Lilith Moon]

My first memory of dressing is standing in my cot so I could see myself in a bedroom mirror. I had found a plastic sheet underneath me and wore it as a sort of cloak, with another sheet as an improvised skirt. Not sure how old I was.

[Rene]

I was 6 or 7 when I first tried on my mothers slip. I was caught by a babysitter, who didn't really mind. It was only a few years later that I would be dressing completely.

[Stacy Reso]

i stated when home alone and thought i would try for some reason unkown to me and i dont regret it. then i couldnt stop doing it i started sleeping cd and being cd when no1 was around

[MsJanessa]

started when I was 11 in moms lingerie because I loved the feel and the look.

[Francesca Chantel]

My worthless ex girlfriend called my wife (when she and I had first started dating) and told her that I was gay, wore women's underwear and took pics of myself while wearing it. None of it was true, so her plan of breaking us apart backfired drastically. My wife, hoever was so turned on by the idea that we went and bought some outfits and the rest, as they say, is history. :)

[kris_dresser]

For me, it was in the early 70's (I was around 9 or 10), a neighbor boy, who had an older brother and sister that had moved out, and we found his brothers porn collection. We started acting out the scenes, dressed in his sisters clothes, all hippie style from late 60's to early seventies. That only lsted a couple of years, and would dress on and off until I left home at 18. I would dress in my sisters gym clothes, and my mothers slips, stockings, and all-in-one open bottom shper with garters, which may explain my penchant for vintage lingerie. From the age of 18 until age 33 I never dressed, then I found a pair of matching panties and bra in the laundry room, and I guess they were abandoned, since I saw them for 2 weeks straight. I took them and dressed for about 6 months every night in them. I stopped again for aboyut 8 years, and started again last year. Now have so many bras, panties, slips, shpers etc.. I need another closet and dresser!

[DonnaT]

I was 6 or 7 when, one day while playing army with some of the guys, saw a girl in my class dress up her brother. They were in the basement of their house, and I was outside the window hiding from the guys. I was immediately fascinated and wished it was me she's was dressing up.

I didn't have any sisters, but saw her in class everyday in a nice dress, which kept reminding me of that day. For some reason, maybe the style, maybe the age, but I didn't even think about my mother's clothes.

One day, when I was around 10, I think, I was cleaning an area of our basement so my dad could build us boys an exercise/weight room. I came across some things my mom had stored, and these were from her youngerr days. One was a nightie and there was also a white peasant blouse and black skirt.

Maybe it was the thought of dressing enfemme many years before that remained in my memory, maybe it was something else, but all I know is I liked the feel of the nightie and put it on. What a rush that was. The next day I tried the blouse and skirt on. Perfect fit and feel.

I took the items from the box and hid them in my room, and the rest, as they say, is history.

[Billie Jean]

Started when my mom let me and my sister wear her mismatched stockings that she was going to throw out. I guess I was around 4 or 5. Then when I was about 11 or 12 I started wearing my sister's pantyhose. That was a sexual thing at the time, but as I got older I around 20 I started wearing heels and quickly progressed to wearing dresses, panties, and the whole echilada. I told my ex about my dressing a few weeks into our marriage and she helped me with my hair (which was shoulder length) and makeup. I'm 48 and have my own wardrobe complete with wigs, makeup, and lots of costume jewelery. I dress as often as I can and love the way it makes me feel and the older I get the less I care who knows.
Billie Jean

[Keri]

The when? as a pre-teen
The where? my mom's lingerie drawers
The what? mostly her long satin nighties
The why? jealousy that my 5 sisters got to wear all the 'nice' stuff;
also, it felt soooo nice ... a sensual feeling par excellance!

[susancheerleader]

My first encounter with "cross dressing" was about 12-13 years old. My sisters were on a gymnastics team, and I was in awe with the girls in leotards. One day I desided to "steal" one of my sisters leotards and put it on. It felt great! I kept doing this, and kept getting caught by my sisters or mother all the time. It lasted a few months before I gave up. I never dressede again and never thought of it at all untill last year.
I was at work and it was hot as hell. I work in a kitchen and was not allowed to wear shorts. So I was always in long pants. I kept seeing the waitresses in thier skirts and wished I was able to wear them.
On day (as a joke) I went into the dinningroom and said to the dainningroom manager (I am the kitchen manager) "If I wear a skirt can I wait on tables" She replied that if I wear a skirt I can do anything I want.
So, a few days later I bought a skirt at a thrift shop and brought it to work. When the staf got there, I went into the bathroom and changed into my skirt I bought. went into the dinningroom and everyone dropped what they were doing.
I said to the dinningroom manager "You said if I wear a skirt, I can wait on tables." She replied "I didn't expect you to do it!" But handed me an apron. Sonn the owner cam in and insisted to take my picture. Soon after that, I went back to the kitchen in my long pants.
But the feeliong of the skirt remined me how good I felt when I tried my sisters leotards on.
It was then I went on an online shopping spree buying leotards, skirts, and "Cheerleader" uniforms.

[Julie Avery]

I've puzzled over this subject quite a bit, and in my individual case, here's what I think.

My dad was an overachiever, very driven, macho, and masculine. My mother was very pretty, petite, and harshly critical of her sons.

I suspect I found it easier to identify with the f than the m in that context. Your mileage may vary.

[Julie Avery]

TracyDeluxe, what a beautiful photo.

[Kimberley]

I cant ever remember not being involved so I would have to say around 4 years of age or younger. I still remember the first experience...vividly. :cry:

Hugs.
Kimberley

[Kimberley]

My first encounter with "cross dressing" was about 12-13 years old. My sisters were on a gymnastics team, and I was in awe with the girls in leotards. One day I desided to "steal" one of my sisters leotards and put it on. It felt great! I kept doing this, and kept getting caught by my sisters or mother all the time. It lasted a few months before I gave up. I never dressede again and never thought of it at all untill last year.
I was at work and it was hot as hell. I work in a kitchen and was not allowed to wear shorts. So I was always in long pants. I kept seeing the waitresses in thier skirts and wished I was able to wear them.
On day (as a joke) I went into the dinningroom and said to the dainningroom manager (I am the kitchen manager) "If I wear a skirt can I wait on tables" She replied that if I wear a skirt I can do anything I want.
So, a few days later I bought a skirt at a thrift shop and brought it to work. When the staf got there, I went into the bathroom and changed into my skirt I bought. went into the dinningroom and everyone dropped what they were doing.
I said to the dinningroom manager "You said if I wear a skirt, I can wait on tables." She replied "I didn't expect you to do it!" But handed me an apron. Sonn the owner cam in and insisted to take my picture. Soon after that, I went back to the kitchen in my long pants.
But the feeliong of the skirt remined me how good I felt when I tried my sisters leotards on.
It was then I went on an online shopping spree buying leotards, skirts, and "Cheerleader" uniforms.
*********
I love this story!!!! Great one Susan.

[Mona]

Always admired the sexy feminine things women wear. Tried my sisters panties when I was around 17, then stole an ex girlfriends panties much later, then met someone who bought me my 1st thigh highs and been adding to my wardrobe ever since!

[Lilith Moon]

As I sit here typing this, my heart goes out to all little boys who want to be little girls.

TracyDeluxe, just to say, you look great !

[arianacd]

I was around 6 , my sister ans I are a year apart and I found her panties in the bathroom and tried them on. I Just loved it. After that I would look forthem in the dirty hamper (which was in the bathroom) and I woulkd try them on. Laterit progressed into her blouses, bras, skirts etc. My parents cfound me out and took me to a shrink but of course that did not help. I have a feeling my mother knows but won't say anything. My younger sister and older bvrother caught me dressed once but have never said anything. My sister is a shrink so I am always careful as to what I say around her, I wish I could talk to her but I know she won't. but alas I am very happy with who I am.

[cutieamy06]

I started a very, very long time ago. When I was 5 or 6. I lived with my mom most of the time and I was always exposed to a more feminine world. I remember I started experimenting with my moms stuff and then it just grew into what it is today. I'm a full-time crossdresser/transgender.:p

[Penny]

Well when I was about 5 I got into my mothers shoes but then again I also
played with army men so I'm not sure that that counts. At age eleven, while at one of my playmates house. he enticed me to get into his sister's underthings along with him. Well that was the start. I have no idea where he is now but I would be willing to bet he too is a sister.

[Jodi Lynn]

I would have to say the same as many other girls, I started around 9 or 10 putting on my mom's things. I would wear every thing of hers bra,panties, hose and dresses. I was allways into make-up too, well at least lip stick. I can remember finding those little sample lipsticks and putting it on my lips

[angelinamillar]

Same as girls, started wearing tights when i was about 7, then when feet were the right size for my moms shoes i would wear them 2. But when i was 13 i went to stay with my dad and i would play dress up with my step sister, so she would dress me in her ballet gear, tights, leotard, tutu, Spent many a happy evening playing dress up whilst our parents were out. And now, I dress as much as i can, just can't get enough of it and have no intention of ever stopping :angel:

Hugs,

Angelina xx

[gennee]

I started crossdressing last June at age 56. I put on my SO's dress and was hooked. mediately. I am a panty nut. Can't have enough panties. I have some tops, skirt, and dress. I slept in a night gown when my wife wasn't home. Man, was that great! I'm looking for shoes and a dress. I love my life as a CD.

Gennee:angel:

[franny]

I wanted to be like mom. seen her in garter and hose, the next day i had her slip on in the basement. fem felt good then i was gone.

[deana cd]

I guess I was about 8 or 9. I began by trying on my moms' slips and hose. I soon thereafter began "borrowing" panties from my sister who lived nearby.

[MsJordan]

just seemed to be drawn to pantyhose and heels since 7 or 8 but finally home alone duringa break from school at age 9. I got a little bored and started trying on mom's hose and heels and dresses even though they were a lot bigger than I was. It was addicting!!

[rachel-h]

first memories were at playschool dressing up in girls dresses then again at 7at a friends house with his sister and being caught by my mum.
Since then it has just been with me off and on and i have loved it, hated it, needed it,and have at last accepted it as part of me.it has taken time though and a lot of heart ache

[karen marie]

i can see how the question why turns into when.i
don't think that any of us really know why we
do it.for myself,i've always had a strong identity with
females.i really believe there are a lot of genetics involved.
hugs,karen.

[Sec_C-CD]

I think it goes back to the arousal I got looking at bra and panty ads in the newspaper. Around age 7 or 8 I remember sneaking a feel of the real things in the laundry. Around age 12 I began to sneak them on for a quick while when I could. Between 14 and 16 I was secretly acquiring my own bras, panties, and lingerie, and exploring my fem side. By 16 I was dressing up alot when I got home alone time. I'm in my thirties now and since 16 I've developed a fine interest in all sorts of female apparel, and it's led to some wonderful encounters.

[jesse]

I guess I was about 11 when I tried on my sisters panties but actually got hooked when I was 18 and in my own apartment. Thanks sis :clap:
it was my sis' romper dress when i was about 10yo

[Monique_Lynn]

Around age 4-5,I spent a lot of time with a widowed aunt, became facinated by her nightgowns, had to try them on, got caught more than once by her, she ended up giving me a couple of smaller nighties and allowed me to play dress up in the attic where ther were acouple of trunks filled with old clothes shoes etc. the rest is history~
ginger

[Lilith Moon]

This thread has reawakened quite a few memories for me...

I must have been very young when I improvised a dress from a bedsheet and wore a cloak, which was actually the plastic undersheet from my high sided cot. Then I graduated to mothers underwear. Oh what wonderful and innocent times!

Other memories from an early age...

Secretly dressing in my younger cousins raincoat and being exposed to the whole family by her older brother.

Dressing up in our garden in some discarded womens clothes...including a raincoat again ! The lady next door, who normally would never associate with us, came out and helped me. In hindsight...I wonder if she had some sort of "thing" about little boys trying to dress as little girls.

On quite a few occasions in my childhood I found discarded bras, corsets and similar just lying around in wooded areas. I had wonderful fun with them at the time although now I think "Yuck"

[Alexandria]

Why did I start? The arousal.

Last year when my GG friends introduced me to crossdressing, I had had a preconceited notion that all crossdressers were gay or transsexuals.

Yet the first day I tried on my first dress (the first time in my life actually), I was aroused. The silk clothing, the feel of a long dress, the satin gloves, the makeup. Most girls probably wouldn't think anything of it, but for me I loved it.

I asked myself "Why do I get aroused?" when I found that things started clicking together starting at an early age. For example, the fashion catalogues I used to stare at, the women I adored, and the sexy clothing I wished women would wear more often.

All my life, I loved seeing women dressed up in fine clothing and it wasn't until I started dressing up till I started appreciating it even more. Apart from the arousal, crossdressing has also strengthened friendships, made me a better male dresser (I rarely wear the same old boring t-shirts anymore), given me motivation to work and more of a reason to draw and write.

I used to dread waking up in the morning to go to college/work. Now I get excited simply by opening my closet and saying "What dress should I wear today?" with work being always a motivation as I have a means to get the clothing I've dreamed of.

[Tammy Lynn]

I Started Puting On Pantyhose An Dresses. I Think Some Of Us Was Girls Back In Previouse Time. I Allso Wore Panties Bras Underneath At School. An I Played In My Mom Closet An My Sister Did To.




Tammy Lynn

[Adele]

I have a similar story to Trisha Anne.

When I was around 6 or 7 I used to try on my Mothers old tights that she put in her sewing store. She also kept some dresses and heels in my bedroom so it was quite easy to dress up at bedtime.

I always remember how elegant Mum looked when my parents went out. I knew then that was how I wanted to look.

Adele. xxx

[barbie lanai]

It was that Sears & Roebuck catalog we got back in the '50's. Would leaf through the women's wear section and see all things girls got to wear that was out of sight from boys. I would imagine what it was like to wear their things. Also with my imaginary money; was buying everything in sight as well.

Then one day I was left alone in the house, and knew no one was going to return for hours. Just started trying mom's things on. Good ol days, no body, hair, no beard, and her clothes & even heels fit me.

By the time I graduated from eight grade (12-13) I had been repeating the process whenever I could for several years. The real kick I got, was when the 8th grade girls were allowed to wear nylons & heels for graduation. I had been wearing the same things before most of them were permitted.

And there I was stuck with a white shirt, bow tie & suit.

[AprilCD]

I was 5 years old when my mom dressed me up in girls cloths for halloween. I complained but when everydoor I came to all I got was, where's your custom little girl? I started to relize then that I enjoyed being a girl.
Years later I saw a movie called "Norman is that You". I started sneeking my mother's nighties and wearing some of her clothes. I think I was around 10 or 11 years of age at this time.

[Lorna]

Being new here, and obviously incompetent, I managed to post a message under the above title, intended for this thread, into the "Schoolgirl attire" thread. I don't know how to move it, so I can only apologise to everyone and promise to try to be more careful next time.

[peterseaking]

had an older sister, 6/7 years older, we were very close. At about 14 years she would let me see her in her underwear, stockings, girdle, panties, some times naked !! Was fascinated, then found some of her underwear, tried it on, was hooked. here I am many years on, still hooked !! Sometimes arousing, another time just NICE !!

[michellecd9999]

well....
I was told my baby sitter used to dress me up when I was under 1 yr old. But the first time I did it was around 12-13. Put on a nightgown.. one of those layered things of nylon and tricot. This would have been around 1969. I loved the feeling. Then moved on to slips, hose, pantyhose, panties, dresses, etc.
Did not dress fully in wig, makeup until I was in my 40's.
Michelle

[Melora]

It all started at a very young age, around 3-4 yrs., my mom would give my a pair of pantyhose to fascinate me.. and oh my god I have been fascinated ever since! Things started todevelope in my late teens, Mome was a Cameo Co. Lingerie sales woman- With a huge amount of showoff peices!, I was inheaven for a very long time.:happy: I Was discovered but she kinda understood, (I think)?, Anyway I started to buy my own lingere, hose, sweaters and blouses and things. Now I am tottaly addicted< with some other problems. I LOVE feeling like a woman!

[MsMichelle22]

Well I got into crossdressing when I was 9/10 because of my older sister.
I remeber it like it was yesterday. One day she was bored so she asked me if she could dress me like a little girl at first I didn't want to but lucky for me she kept begging til I said ok. She dressed me in frilly yellow panties, white petticoats, white tights, black maryjanes, and lovely yellow satin party dress.
She also put pink lipstick on me and came up with my girly name Alexis Michelle. I ended up loving it so much my mom started buying me my own clothes and raising me like a girl and actually got me into an all girls school for middle and high school no one found out my secret but one girl who is now my wife.
Aaah memories:battingeyelashes:

Michelle:doll:

[Khriss]

a blizzard..boots...age 9...and...

[PennieS]

My first memories of it were when i was about 5 or 6 I found some old clothes of my sisters and moms in the basement and just had to try them on. Found some nice days of the week girls panties and a short grey skirt which i just loved and hid and wore whenever i could get a chance. i have been hooked eversince and even was as brave to wear the panties to school some days. i still vividly recall looking through that first batch of girls clothing in the baement that day arround 45 years ago.