How did you start dressing

[charlotte72]

Hi

I was age 6 in a school play as a mouse wearing brown polo neck, brown tights, ears and plimsols. It was a feeling that never left me how comfortable tights were. After that i dressed at every opportunity. My mother's old clothes were used. I was caught and talked about my dressing and had therapy at university but nothing has prevented me from dressing at every chance i got. I hid bags at work and in my loft.

I am not convincing but i am convinced I am right and should enjoy life and being me.

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you are right its the feel and escapism. The need to express in whatever clothes you have.

[Lori Anne]

I was about 13 or 14, and had a younger sister who was a "clothes hound". I started by "borrowing" a pair of her panties from the laundry, next came a bra, then a skirt and top; then it just escalated until I finally got caught. A few years later, I discovered mail order catalogs. A few more years later, I got brave enough to do my own "in person" shopping.

[Mackem Sue]

Bizarre is one way of saying itt.

Strip Poker Computer Game mid-to-late-80s, got the lady down to her undies and stocking before she beat me. I wondered what said attire would look like on me as I liked too much what I saw.

Sampled. First time tights.
Second times bottom half (tights, knickers, skirt heels). Third time full crossdress including bra and laid my hands on girdle and stockings.

No turning back.

Sue.

[Michelle1955]

I was very young, the only kids on my block was 3 girls / 2 my age / 1 little younger. So by default my daily playmates. So their was a lot of playing house. I do feel it does start in the brain and do believe even before we are born for some of us early bloomers.

One day while playing with one of the girls in her bedroom we ( around 5 years old to the best of my knowledge) decided to trade underwear/ panties to each try them on.

Still was a defining moment in my life the feel of panties and her my underwear.
60 years later still my preferred choice (panties) 24/7. Underwear not in my dresser drawer.

[Larissa Cassandra]

I actually started with lipstick. I didn't have a mother or sister growing up, but maybe it's because of that that I became infatuated with girls and women. They were these marvelously beautiful creatures and I was jealous that they got to wear clothes that I couldn't, and make their faces pretty with makeup, and have fancy long hair styles. So I would put chapstick on my lips and pretend it was lipstick. Then a miracle happened - a girl who came over to my house to see my older brother left her lipstick on our piano. OMG, a REAL LIPSTICK!!! I surreptitiously put it in my pocket and later went into the bathroom and put it on. It was a light pink, what the girls were wearing at the time, and it was an amazing feeling, not just the creamy feel of it, but the taste, and of course the way it looked on me. This was very arousing and the idea of adding lingerie, stockings, and dresses was extremely appealing, but I had no way to get any of those things. I did try on my aunt's slip while visiting, but that was about it until I was married for the first time and could attempt to try my wife's things when she wasn't home. They never fit well, so fast forward about 25 years and I started accumulating my own clothes and makeup. It's getting better all the time (where have I heard that before???), and now I'm dressed most evenings in the comfort of my home, and with my loving and supporting current wife.
~Larissa

[Diedre]

At around age 12 or 13 my mother started using me as a dress dummy for dresses and skirts she would make. I really got hooked and started showing way too much interest in helping. Unfortunately I got replaced by a dress form from a resale shop. I did get to continue dressing with the help of a female cousin, but that's another story..

[JulieC]

I didn't have any sisters, so raiding their clothes wasn't an option. The only option was mom's clothes. It all started with pantyhose when I was around 8. I had the occasional time home alone, and would take advantage of it. This didn't happen very often though. I wonder if she ever suspected. Fast forward to age 14, and I had a paper route. I accumulated a few things which I hid rather poorly, and my mom discovered my stash. My mother, being a single mother, was under enormous strain. I didn't realize this until I was much older. She read me the riot act, etc. None of it had the effect which she intended. It taught me to start a new stash, and to hide it very, very well. I left home two weeks after graduating high school (bootcamp) and never lived at home again, other than a week or two here or there, holidays, that sort of thing. I loved my mother dearly, even though she was never accepting of my femme side. That was the only encounter we had on that front.

On the plus side, my experience with my mother on this topic helped to teach me to not embrace non-acceptance. It took a while, but I eventually got to the point of refusing to accept anything less than heartfelt acceptance in women I dated. Had my mother never discovered my stash, it might have taken me longer to gain that strength. In part thanks to that, I've been married nigh on 20 years to a wonderful, amazing woman who accepts all of me, and buys things for me on occasion (including a beautiful pair of Bandolino pumps that she wishes she had bought for herself!).

[Tracy Irving]

I started with my mother's nylon granny panties around 5 or 6 years old. I remember putting on many pair until the drawer was almost empty. One just wasn't enough...

Better yet was when the panties were in the laundry basket waiting to be folded because I didn't need to be as careful putting them back.

[Melanie Sykes]

The first time I remember consciously thinking about it was at the age of about 4. My mother's friend had come round to visit with her daughter, who was a year older than I was. Rachel and I were playing in the back garden - it was early morning before school, and she was in her school uniform with these really shiny patent black Mary Jane shoes, and white pereline socks. I remember looking at them and wishing I had a pair of shoes like that.

A year or so later Rachel's mum had left her with us for a couple of hours, and Rachel and I were playing in the back garden again, this time with a paddling pool on the lawn. Rachel fell over the edge into the pool fully clothed and promptly began howling. The pool and the weather were both pretty cold! My mum ran out, wrapped her in towels and took her into the house. Rachel emerged later fully dressed in my clothes, my mum having put her clothes to dry. I remember thinking at the time that if that had happened to me at Rachel's house, there's no way they'd have dressed me in Rachel's clothes, and that made me sad.

One night when I was about 8 I had been in the bath and was on my way back to my room when I passed my parents' room with the door open. My parents were downstairs watching TV. I went in to have a look in their built-in wardrobe - sometimes they hid boxes of chocolate bars in there ready for Christmas, the sort of bulk discount boxes you get from a warehouse. I don't remember if I found any chocolate in the wardrobe that time, but I do remember spying a pair of tights and a long pleated skirt on the floor. I wondered what they must feel like to wear. They looked as though they'd feel great, but I also knew men weren't supposed to wear them. So I stealthily slipped on the tights, and then the skirt, and walked about softly in the room. The feeling was absolutely electric and there was no going back. It was years before I ever got to fully dress though - well after I was married IIRC. Through my teenage years I was happy with tights, knickers, and a skirt, borrowed from my Mum due to a lack of sisters or au pairs. By the time I thought about shoes, my feet were way too big.

[RobynG]

I was 13 when my sister moved out of the house. My parents were starting to find a way to eventually to get divorced. I found some clothes she left behind in her room and I tried on a bra (that i eventually fit into) nylon panties and a denim miniskirt, that was the start of 47 years of dressing as my alter ego. First wife bailed when she found the stash, 2nd wife is okay with it as long as she's not watching the other side

[andreah]

started when l was around 11 years old , found a pair so stockings my sister put in the laundry basket , decided to see how they felt on my legs ,so l try them on ,and l love how they felt . when pantyhose came along decided to try them on also , l would dress in my sisters dress pantyhose and heels when the family was out for the day , one day l showed my friend next door how l was dressed , he liked seeing me dressed ,and l would dress just for him this went on for a couple of years until we moved away , l kept on dressing every now and then , until l moved away , now l dress for my self and for a few of my female neighbors they seem to be okay with it . l only dress from the waist down

[Taylor186]

At six I fashioned a dress out of a bath towel, with marginal success. At eight I was "forced" to wear tights as a part of an elf costume in a class play. Quickly thereafter, I progressed to my mom's bathing suit with a flared skirt (loved that), her stockings (drying on the shower curtain rod) and girdle. But really, it was just bits and pieces in my teens and twenty's. Early thirty's I first went out fully made up, on Halloween. of course. It snowballed from there.

[sometimes_miss]

Shortest answer: Mom dressed me in my sister's old clothes when I was a toddler. That stopped when dad came home early for lunch and went ballistic. Later, when I was envious of mom getting my older sister ready for school, I took one of sis's dresses, put it on, and went to them and told mom I was ready for school, too. She changed me back. After we walked my sister to school and got home, mom asked if I really wanted to wear the dress, but said it in such a way as to imply that I should say no, so I said no, even though I did.
After 1st grade, met an older boy who would tell me that the reason my penis kept disappearing (it was cold outside, was the real reason) was that god made a mistake, and that I was really supposed to be a girl. He 'proved it', by getting me some of his sister's clothes to try on, which at that age, of course, fit perfectly, and when I looked in the mirror, saw what appeared to be a cute little girl looking back at me. He would turn me into his private little sex toy girlfriend for the next 7 years, while I patiently tried to learn how to be the best little girl I could be, and waited desperately for god to 'fix me' and turn me into the girl I was then sure that I was supposed to be. All during that time, I would raid my attic of all my sister's old clothes that mom had stored up there, always careful to put stuff back exactly as I found it to avoid any suspicion of what I was doing. Since mom and dad worked, and my sister got an after school job as soon as she could, I spent much of my middle and high school years after school, in dresses and skirts, pretending that I had, indeed, become a girl. After all that, apparently the idea that I was supposed to be a girl became permanent in my mind, even though the conflicts between being a girl and being a boy remained.
Long answer is in my bio, link in my sig, below.

[leliani]

I think my start was possibly a little different compared to most. Up to the age of 17/18 I had no desire to be girl or wear girls clothing. Then I was visiting England (I grew up in England and moved to America when I was 15), and was out by myself walking around London. I was walking down the street and happened to walk past a lingerie store. In the shop window, the mannequin had on a sexy pair of silky white panties with pretty bows and lacy accents. And I just remember wondering what it would be like to wear them. I figured the satin/silk would feel really good.

Later that trip I found myself alone again at a local shopping mall. I decided I would go and sneak a feel of some panties. I went into a large department store where I figured I could go mostly unnoticed, but I was still so nervous and my heart was racing. I must have walked past the lingerie department 8-10 times waiting for people to clear out.

FINALLY I managed to sneak in and quickly ran my fingers over the crotch of a satin pink thong. It only lasted a couple of seconds, but it was enough for me to make a promise to myself that once back home, I would buy a pair for myself. And that's exactly what I did. I'll never EVER forget the feeling of running a pair of satin panties up my legs for the first time. And after that it just went crazy. From panties I went to bras, then pantyhose, lingerie (nighties, teddies, corsets), then finally clothing (skirts, dresses, leggings etc.).

I have to be honest and say that at first it was purely sexual. But once I starting wearing proper clothes...my feminine side was almost uncontrollable. I am a completely girly girl when I'm dressed...all because of a pair of white satin panties in a shop window...

[AllieBellema]

For me, it started when I saw my grandma watching movies like Gone With The Wind and when I saw the gowns in that movie, I fell in love and wanted something like that. Obviously, those were old times and stuff like that wasn't passable in the age I was in when I was a teenager. However, my grandma also had enough clothes to start her own K-Mart.

On days when my grandparents went for a ride and left me home alone, it allowed me to explore her closet and another closet that was stuff to the gills with clothes. I found some nice blouses, skirts, swimsuits, etc. Eventually, I kept some of them in my closet where they wouldn't know that I had them. Eventually, when I got ready to move out of the house, I had to wait for a time when I was home alone again just to put it all back. They never knew that I had anything in my possession.

[JuliannaS]

When I was a teenager, I used to "make" my own girl clothes out of old clothes, cutting them up and sewing them. I'd also use my mom's nail polish when no one was home.

[Claire M]

Another mission for when they invent the time machine, go back and tell young little me that someday people on computers will ask you multiple times about this scary thing you started doing so make sure you permanently remember the first time!

I still remember every detail of my first time ... the time of day, the room, even though pattern of the cloth ... and most importantly how I felt about it!!

[Alex!]

I believe I tried on a pair of opaque black stockings owned by my cousin. I've no idea what prompted me to do that. I also have a vague memory of being an elf in a Christmas play, and that meant wearing stockings and some makeup. Maybe that's how it started, in the midst of puberty, which locked in two streams of excitement to produce a unique result

[Lacyfem]

Well I guess prior to my putting on my first pantie and bra at 10 I enjoyed seeing my mom get out of the shower and sitting naked on her vanity stool and putting her makeup on. Then her slipping on her panties, slipping her bra on my leaning over and putting her lovely breasts into her C cup bra, then into what she was going to wear that day or evening. So, one day the folks went out to dinner with friends and they'd had a few cocktails before going out so everything was left out and I decided it was time to try dad's bourbon. It didn't take long before I was a bit high and I guess a bit uninhibited as I proceeded to take all my cloths off and went to mom's hamper and put on her full cut nylon pantie and then her bra which I stuffed with other panties which were in the hamper. It felt so right but I was basically a bit drunk. I then went out into the yard which was quite private and felt so free and I guess fem and proceeded to walk around the house and I'd stop and take the pantie off and pull another out of the bra which I'd stuffed in there and put that on. I did this for quite awhile all the while feeling like a grown up gurl. As you can imagine at that time of my life it was so exciting that I was very sexually aroused though I knew very little at that time about sex. So it was quite an evening and I must have got all back in order as nothing was said the following morning. However, even to this day when I just put on a bra and pantie I want a sip of some bourbon as that was my starting point and glad I did it.

[Barbara Jo]

I was born in 1947. I am a middle child with an 5 year older sister and a 4 year younger sister.
Wen i was about 8 years old in the mid 1050s and my older sister was was 13 years old, she started to wear some of the quite feminine clothing of the day.... dresses, pencil skits etc... including the great 1950s lingerie... including nylon stockings and garter belts.
She mainly dressed up when going to school as most girls did back then .
Her breast were also developing and she started to wear a bra.

BTW, my mother also wore all the female clothing and lingerie of the day.

Anyway, one day I began to wonder.... more and more, what it felt like to wear all that female clothing and lingerie.
One day, when I could no longer resist it ... when I was going on 9 years old..... I secretly put on one of my sister's silky panties, her bra and a full slip..... and I was hooked.
I then secretly wore female lingerie and clothing every chance I got

[Jannis]

That could be my story. Oh, this started so,young.

[Lori Ann Westlake]

I started getting the urge about the age of thirteen. I only had my mother's clothes to wear at the time, but they fitted me fine back then, even her shoes. Although her silky panties were especially erotic to me, as they were to so many others, the odd thing was that I didn't start with her underwear or nylons. Rather, it was one of her skirts that first attracted me, so I put it on and it gave me a thrill. While I soon found her panties held a special thrill of their own, I think at some level I was attracted to dressing completely as a girl right from the start, so a skirt seemed an obvious place for the first tentative experiment.

Anyway, once I'd tried that on, everything else came in a rush. It seems strange that I can't recall the first exciting time I slipped into her panties and other underwear, but while I can't remember for sure, I suspect what happened is that I did plan and jump into everything all at once one day. Certainly as a rule I would wait until a morning when I was alone in the house, then collect up bra, girdle, nylons and panties, full-length slip, skirt and blouse (or dress) and shoes, laying them out and surveying them with anticipation before putting them on one by one, leaving panties until last, sliding them up nylon-clad legs under my skirt, then reveling in the sensation of being completely dressed as a girl in skirt, blouse and underwear. I was very careful about putting everything back afterwards. I continued doing this through my teens. I don't think my mother ever knew; at least, if she did suspect, she never said anything. In my later teens I started buying a few items of my own: blouses, panties, half slips and so on.

[Jamie1980]

Somehow, with my sisters help, I put one one of her dresses. We were under 10 at the time. It was a whiten dress with a dog on it. I ran around the yard and my life has never been the same.

[dalearden]

lust floored at so many similar stories! I to started young, maybe not even teenager, I remember trying on a pair of hose and a dress at home, the feeling was overwhelming....I didn't do much with it until and adult and ordered a pair of tights one year...and discovered online ordering!

[DTelia]

Seems these repeated question/post come all of the time and these stories go on and on. They intrigue me, because on one hand I like to relive it in my mind, but it?s sad on the other. And when I see the post, I?m a sucker to read them. I WISH there were some good stories that were more ?discovery type? stories, w/out the perversion that I sometimes see...I don?t mind the hormones/sexual tension, but some of the stories...are just stupid and so fake, they don?t do anything...so if you know of any good ones...please share.

Here?s mine....I have no regrets however.

I was probably five years old. I enjoyed watching my mom do her hair in curlers and then wearing a bandana all day long...nothing really ?pretty? about that and the wife cracks up when I tell her. But I either asked her to do it to my hair, or she just did it...and there I was w/my own curlers and bandana. I don?t think anyone beside mom saw me. They did see the curls, and I got attention that I didn?t like or understand...I didn?t really think curls were natural back then...it was a girly thing.

So from that time on, girly hair drew me in. But not all hair and not on all girls...to this day, there?s a right and wrong way, so I learned to have an eye for detail.

But I kept it a total secret until I met my wife to be.

I wanted to be 100% honest with her...so I was. I didn?t really translate it to ?dressing up?, but dressing up kinda made they hair, the face, the look...more complete...so my interests grew.

Love women...love their beauty, and my wife could see my genuine curiosity about it. She encouraged me occasionally to dress, to grow my hair, which we really never did until about 10 years into marriage, when she wanted me to try it. She started buying me some stuff and I would try things...she was surprised that I looked ?ok?, and little by little, maybe once a year we would try more. I was always open and honest with her. About 10 years ago on my birthday, she bought a bunch more stuff, and encouraged me to dress more. I did a little bit, not much...but then I started to embrace it, I started realizing the improvement in my life that it brought me (I know this is debatable for some, but my wife sees it).

Now, for the first time in four + decades I?ve grown my hair (grateful I have hair!) for the second time in two years to small pony tail length and TODAY, I gathered all of my hair into a full pony for the first time...walk around the house and have even been out and about with it. It?s wonderful...and honestly the pink fog isn?t much a thing with my hair like this. Hoping to keep it in a nice low bun like length and then bring it down and do other things when the fun starts.

I would love to talk to my mom about it, but don?t want to worry her, so I?ll keep my secret.

I could right countless stories about my sad experiences that never happened...but I?m honestly so grateful to have a wife who not only supports me, but stands up and encourages me...?You can keep it DT, play w/it...I?ll play with it, etc...but you have to keep it looking great (healthy).?

It?s really crazy...I wanted to dress every Halloween....NEVER did. I didn?t want to be caught or accused...there are so many other examples like this. The lesson I learned is that in the end, most people don?t care. My biggest thing, is keeping the kids in the dark on this...to them, Daddy just has cool longer hair (or maybe they think I?m weird), but that?s it.