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KIM SLIMS
03-14-2021, 09:30 AM
Hi I was wondering how we all get started. I started with my sisters clothing like panties and bras got into jeans and dresses. I was busted by my mother one day. She was not really ok with it but she did take me shopping for my own girls clothing. When I was 18 I only had girls clothing to wear

Star01
03-14-2021, 10:13 AM
Got into some clothes in the attic in 1964 at thirteen. First gender related memory was Superboy #78 story about being changed into a girl. I was probably around 8 and vaguely recall expressing a desire to be a girl. I remember a blowup between my parents about me and comic books and I think there is a connection.

shortskirt87
03-14-2021, 10:19 AM
when i was about 15 years old or so, my mom and i were at the mall and she asked if i wanted my ears pierced. it was popular then, and then i started wearing her earrings all the time and fell in love with the feel and look of girly earrings. i started wearing more of her clothes and it spiraled from there.

MysecretSummerlife
03-14-2021, 10:30 AM
I started with pantyhose. Loved the feel and look. Id "borrow" them from my mom. It then progressed into panties. That lasted up until high school. I got busted a few times and was forced to go to counseling. I stopped through high school and regained a love for panties and hose in college. That progressed into being able to dress since I was away from home. Now 10 years later and I dress when able.

stefaniec
03-14-2021, 11:39 AM
My story is pretty similar to most. I started to notice and be attracted to girls around middle school, but part of what I was attracted to about them was their cute uniforms (private school) and tights they could wear. As a kid, there was just a big basket in the laundry room where everyone put their stuff that needed to go in the wash. So one day when I was putting some clothes in the washer, I noticed a few pairs of mom's pantyhose in there from the work week. I was really fascinated by them and snuck a pair off to my room and tried them on. I just remember what a thrilling experience it was. I had never felt anything close to the feel of that beige nylon on my skin, and knowing that I was doing something I shouldn't have been doing was also a rush.

After that I was obsessed with exploring more. I wanted to try on panties, skirts, bras, high heels, the works. Unfortunately by this point in time there was a noticeable size difference between me and my mom, and with no sisters I was mostly limited to sneaking away her pantyhose and panties. One time I had a chance to check out the shoes in her closet but they were way too small.

I didn't get to dress much in my teens or college years, but once I was on my own and had my own place I really got into dressing a lot more. The last phase for me wasn't until my early/mid 20s when I finally started buying wigs and makeup. That really launched my dressing up to the next level.

docrobbysherry
03-14-2021, 11:49 AM
A tenant moved out and left a box of her old clothes!:devil:

Karren H
03-14-2021, 12:01 PM
I was 7.... mom had always said I was supposed to have been a girl. She always wanted to make me girly dresses for Halloween. And I never took her up. But when my sister was born I became obsessed with sneaking into moms closet and trying on her bras and girdles and stocking and nighties. That was over 6 decades ago and I am still obsessing and have the breasts to prove it! Lol.

MonicaPVD
03-14-2021, 12:05 PM
Around first or second grade I started borrowing mom's hose. It was all downhill from there. Fully dressed for the first time around age 15, went out in public for the first time around 16, dressed a lot during college, then became a boring hetero guy for a very very long time. Too long.

CrossKimmy
03-14-2021, 12:14 PM
I was probably 7 or 8 years old when I got into my mother?s wardrobe. I was alone for like 3 seconds and saw her pink and neon green tulle skirts and was quite taken with them so I put them on and played ballerina. Then I decided to keep them in my wardrobe but they were quick to find them and I was told that this was not acceptable. But they probably thought it was a phase. Well look how well that turned out for them lol

Elizabeth G
03-14-2021, 12:45 PM
I was about 11 or 12 years old. My mother ran a pretty tight ship at home so the only thing around the house that might satisfy a young boys curiosity about girls were the lingerie sections of the Sears and JC Penney catalogs. Over time I realized I was just as fascinated with what the models were wearing as I was with the models themselves and I found myself wishing I was one of them. It just took of from there.

Pumped
03-14-2021, 01:02 PM
I was very young, maybe 5-6 years old. This was early 60's, living on a farm miles from the city so I couldn't just go buy stuff. I started messing around with my moms bras even though they were huge on me. I would stuff them with t-shirts and pull another t-shirt. I cut up up a t-shirt to make a skirt. I had an older sister, but she didn't have much girlie stuff. It was pretty much a disaster, but it was all I could come up with. Even then I was into big boobs!

Later on in my early teens my parents got divorced, lived with my dad and I was able to collect a few items. Then dating and marriage and I took a 30-some year break even thought I still thought about dressing. My wife is tiny so her clothing wouldn't fit and nowhere to hide anything away living in a tiny apartment.

kellyanne
03-14-2021, 02:12 PM
At a very young age , bras, panties & the appearance of lingerie clad women in catalogs were very appealing.
Years before puberty, wearing my mother's bathing suit made me feel free, whole and truly myself, I had went to the dryer , opened it and felt I had to wear it to be me.
In grade school, the sound of the walking teacher's pantyhose on her girdle was beautiful to my ears.

In retrospect, the onset of puberty seemed to put the dressing aspect in dormancy but the love of lace continued.

I couldn't dress in full until I lived on my own in the last year of college.
Before the last year , leaving town for summer work forced a toss my ladies clothing for lack of storage.
Since then I have lived on my own and dressed at will.

It took some time to do it well, size properly, match colors well and put on make up better.
A wig website helped pick the better wig style and I have pretty well stuck to it.

The 2 things I wished I had done earlier is buy breast forms& Transform bras and a shaper girdle.

Make up is easy once you get the hang of it.
A really nice lady gave me 2 tips always remembered:
- less is more
- blending ( with the fingers) is the secret to a great natural look.

I enjoy seeping in my bra, forms, panties and nightie every night and it gives the same sense of freedom to face to day as such.

At 60, coming up 50 + years dressing, almost 40 + years dressing in full with wigs, make up, heels etc.

We can only be what we are.

Marcia Blue
03-14-2021, 04:27 PM
I was 5 years old. Mom and Dad had gone over to the neighbors for a visit. I was attracted to Moms lipstick samples. Mom sold Avon so there were lots of choices. I tried on several colors that day. I was hooked. That same year I started trying clothes along with the lipstick. By the time I was 8, I was also into mascara. I never ever really stopped dressing.

Mom caught me once in High School. Dressed to the nines, in her clothes. She never said anything to me about it. I learned to be even more careful. Once when Mom, Dad, and my sibs were going out of town, after she caught me. Mom pulled ma aside and said to behave while they were gone. She also told be to stay inside if I, was not "properly" clothed. I stayed home except to go work. My hair was bra strap length then. I wet set my hair, and spent most of the week dressed. To this day I wish I would have at least gone out for a drive all dressed up.

Bluesman
03-14-2021, 08:54 PM
I was 15, playing one of the kid roles in a professional production of Macbeth. Dressing room space was limited, so couple of the gay men and me (go figure!) shared space with the female cast with just a clothes rack separating us. One night when I was alone in the dressing area, I noticed a pair of panties on a chair. I pocketed them, took them home, put them on and masturbated. Around that same time I discovered a trunk in the attic with a couple of nightgowns in it and started wearing one to bed. Over the next years I found or purloined panties until I got up the nerve to buy my own along with a matching bra in my early twenties. Dressing was limited to those kind of lingerie items, off and on, periodic purges, reading cross-dressing letters and stories in Penthouse Variations (how many remember that publication?) til my mid-30's when I bought by first dress, which was later purged. Things continued that way more or less for the next 20 or so years, hiding it for the most part from my wife. In my late fifties decided the only thing "wrong" with CDing was hiding it from her, so put it more out in the open. Didn't go well initially, went back into hiding although the secret was out of course. Eventually started purchasing dresses, skirts, blouses, shoes, etc. wearing them in private, and occasionally being caught if my wife came home unexpectedly. It's all out in the open now although not always comfortably so. I mostly dress when she's out and I change before she gets home (she usually texts me she's on her way). Sometimes she forgets to text and I'm still dressed; it's a little awkward but not distressing. Occasionally I will dress when she's around, especially during the lock-down period when we were pretty much home-bound all day. So that's the journey that all started with a horny teenager and a pair of purloined panties.

Sometimes Steffi
03-14-2021, 09:36 PM
I was about 12 when I stepped into my mom's panties one leg at a time. I didn't realize that there was any other way to do it.

ShelbyDawn
03-14-2021, 09:51 PM
Five or six, fell in love with how soft my moms slips were, started wearing them when no one was around. Quickly gravitated to stealing/borrowing panties from my sisters, and then on to bigger and better things as I got older.

AndieB
03-14-2021, 10:23 PM
Age 3 or 4 I was caught wearing one of my mom's nighties. My dad said to my mom, "looks like we caught a princess." I'm fairly confident that is one of the earliest memories in my life and I've been dressing up to some degree ever since. I didn't really get into makeup until my later 20's though.

Jeanettew
03-15-2021, 12:38 AM
I was a late bloomer a few years ago when I was about 35 the football club I go to was holding a Miss Club contest, and as a laugh some of the guys said we should try and railroad it and one of us should enter, my wife overheard and said she would help, the day arrived and so in my man undies she gave me some of her old tights found one of her lose fitting dress's and old Bra and some balloons she filled with rice for boobs, some make up and one of her sisters wigs, shoes were hard but she found some at an op shop that fitted, off I went and it was a fun night.

Laying in bed that night all I could think about was how nice the tights felt against my legs and the dress was something else to wear and I wanted to try more, it was a few weeks later when she went out for the night with the girls and I spent the whole evening trying on her cloths, I was hooked, but I needed my own so I started to build my own closet, Stocking Undies dress's, skirts and heels, I just live for the feel of stocking and heels. that was thirty years ago

Cass42
03-15-2021, 04:44 AM
Age 7,was at an aunt's house and she had this dark navy dress on the floor.Mom and I were over to visit.They discovered I was gone and the bathroom door was closed.Was in the bathroom putting the dress on.I walked out with it on.Both saw there was something about me,I was not the typical boy into boys loved to do.Saw I loved wearing this dress.

SaraLin
03-15-2021, 08:11 AM
I've always felt like I "should have been a girl", but also knew from a very early age that this wasn't "normal". Needless to say, it caused a lot of turmoil until MUCH LATER I learned to start accepting myself.

But putting that aside - the first things I remember doing were (not sure of the order)

Spending the night at grandparents house. They didn't have PJ's for me, so GM used one of her house dresses, with a belt to tuck up the excess length. I was in heaven!

Cub scouts - in a skit, got cast as the princess - string mop head for hair, and a paper heart pinned to my chest - that I gave to the prince who rescued me - from what I don't remember.

"borrowing" my sister's clothes and wearing them in bed, under the covers - until mom found them, and I had to scramble for a good lie.

Finding boxes of feminine clothes in my grandparents' attic that I could wear. I "liberated" some of these and hid them in an abandoned house in the woods, where I could go and be a girl.

One halloween, and too poor to afford costumes, mom let me put on a dress -and yes, another mop head for hair. A neighbor lady loved it and said I was "the cat's meow"


It would be easy to claim that these things LED me to my feelings, but in fact, I feel it was my inner feelings that led to most of the events.
For example, I would make up excuses to stay the night at my grandparents' house, knowing I'd get to "be a girl" for a little while.
About the only one that I can't say was a result of my inner she-ness, is the scouting skit. and maybe even there, they sensed that I was the right one for the part???

Beverley Sims
03-15-2021, 11:03 AM
I was dressed by the next door neighbours girls we playedmothers and fathers and I was the baby.

Later they dressed me up in their clothes and went for drives in the country with their parents.

Cheryl T
03-15-2021, 11:08 AM
At about 5 or 6 I suddenly had the urge to wear mom's panties.
Of course at that time they were nylon and so silky and smooth. They just felt wonderful. Next I wore a slip for the same reason, but noticed the "pockets" up top and stuffed them, but everything fell out so eventually came a bra and sock stuffing under the slip. From there it was her OBG with garters and then stockings and her heels. The rest is history.

Deborah G
03-15-2021, 11:50 AM
Started with my sister's clothes, i.e. panties, high heels and Keds shoes. She and I were about the same size. Then I tried on her hose with garters, dresses, bras, skirts. The feelings I have wearing these things cannot be described! Some things just feel right!

Felixkoch2312
03-15-2021, 12:22 PM
Liked your one ;)

Claire M
03-15-2021, 05:49 PM
The first I consciously crossdressed I was 13. I had a major urge to see what it felt like to slip into a pair of my older sister's panties (white cotton with little blue roses still remember every minute detail 50+ years later). A few weeks later I HAD to see how one of her bras felt. And within another couple weeks I was fully dressed in one of her skirts a sweater and heels ... just to see how it felt. Needless to say it was wonderful .. confusing ... scary ... me (usually followed by a bit of guilt and shame be a useful after all boys shouldn't do things like that.)

Jemima Stephens
03-15-2021, 06:26 PM
When I was 7 or 8 I went to childminders after school every day who had 2 daughters similar age to me. One day one of the girls spilt her drink all over me, so when my Mum came to pick me up I was in a pink T shirt, brown girl's trousers and pink knickers. I remember getting home and standing in front of the mirror not really understanding why it felt oddly nice.
Needless to say the girls thought it hilarious so I got drinks spilt on me a few times after that!

Georgina
03-15-2021, 08:35 PM
It was over 60 years ago that my interest in female clothes began. I am not really sure how I started but, since I had no older sisters, it was my mother's clothes that attracted me. I remember beginning with slips and moving on to girdles and stockings. I was never interested in panties and, to this day, I still am not that involved. I wore only lingerie for a few years but eventually moved on to outer wear. Now at 68 years old I still wear a girdle, stockings and a slip with my dresses and skirts.

Christina89
03-15-2021, 09:05 PM
I was about 12 or 13. I was watching a TV show called Totally Spies. I suddenly had an urge to go upstairs and try on some of my mother clothes. The first thing I tried on was one of her bikinis. I loved the feel of how it felt on my body. After a few minutes I took them off and went back to my normal routine for the night. The next day at school I couldn't get the thought out of my head. It was all I thought about. I couldn't get home fast enough to explore it further.

Katherine L.
03-16-2021, 10:24 AM
I got started when I was 11 or 12 and tried one of my mom’s bras I found in the clothes hamper. After that first time, I would regularly check the hamper to see
if there were any bras I could wear. One time she caught me wearing one, but didn’t make a big deal of it. I was extremely embarrassed at the time, but not enough to ever stop.

Stephanie47
03-16-2021, 05:09 PM
I had no older sisters or female cousins and no female playmates. As a little kid I did like the feel of my mother's nylon slips which I fondled and finally put one on. I loved the female of the material. Had no desire to be a girl. When puberty hit I found myself delving into my mother's lingerie drawer and wearing her girdles, bras, panties and slips. That lasted until I outgrew them.

Lana Mae
03-16-2021, 05:49 PM
At 4-6, a playmate flipped her dress over her head! That was neat! I wanted a dress! No, boys don't wear dresses!
13 or so, mostly a sexual thing that lasted many years! It only involved panties! Once though, it was panties, bra, long leg panty girdle with stockings and a slip!
Then married and wife didn't want another woman in the relationship! 34 years and 5 months later she passed away! During that time only panties 5 times and purged each time!
Found this site and the rest is history!
My little playmate that started it all was Lana!!!
Hugs Lana Mae

UsuallyRick
03-16-2021, 06:16 PM
As a youngster my parents friends were over with their daughters.. I was probably 8? We found my older sisters dress up clothes and got dressed up!! It felt great and I have since that day (or maybe longer ?) had a thing for stockings, dresses,panties etc .. liked the style and colors more than the drab Wranglers boys wear.. did I mention the girls and I got caught? Yup barely even a question and I admitted I liked it! Years later in high school I had some friends with hot sisters, I would steal their sexy panties and wear them,nearly got caught several times and accidentally left some in laundry, mom did my laundry and left them nicely folded on top of the pile.. I assumed she thought a girlfriend left them? Or not...?? I was that awkward size where boys pants were too short and men's were too big around so handmedown girls jeans became the norm.. then several years before my wife and I married we went to a Halloween party dressed as hookers.. now I can't get enough and have more skirts etc than guys stuff

jacques
03-18-2021, 08:38 AM
hello Kim,
I started by wearing tights,
luv J

BrendaPDX
03-18-2021, 09:12 AM
The moment when I knew I was hooked was when I bought a dress from the Salvation Army. It was a little on the modern side with beautiful colors and pattern, it fit perfectly, and when I looked into the mirror I knew I was hooked. I remember thinking a girl that pretty would probably never date me. LOL

LeannS
03-18-2021, 09:18 AM
It was 10 yrs ago I left a job and moved. It was a economical depressed area and I thought I had some pretty good job skills boy was I wrong. anyway moved in with a gal that would become my wife 3 yrs later. So I took on a role of a maid, chief bottle washer, cook and personal assistant. I thought hell if I am doing the part I might as well dress for it and so I did just so happens she was the same size as I am. The rest you might say is where I am at today Hair on, nails on and dressed to do the house cleaning leggings, knit dress and boots. Have a great day

CynthiaD
03-18-2021, 10:11 AM
I’ve told this story before, but ...
When I was 3 I begged my mother to paint my nails with red nail polish, and she complied. I ran outside to show the other kids, but they all told me that only girls wear nail polish. I didn’t care. I loved the way they looked. And 69 years later, I still do.

Dana3
03-18-2021, 06:18 PM
From as early as I can remember as a young boy, I've ALWAYS been strongly drawn towards girls ~ women and any all things related to.them and feminity.

I never felt i.wss anything other than the person I was born. That is to say i wouldn't say I was nor suffered from gender dystopia.

That was "part" of it ~ part of my internal make as an individual.

I always preferred the company, companionship, being friends ~ playmates with girls ~ women.

That to was part of of my internal makeup.

I've always been somewhat envious ~ jealous of girls ~ women.

When just entering adolescent ~ early on set of puberty i was drawn towards a need to experience and express feminity.

First with my Sisters and Mothers lingerie, clothes and makeup, and later with that of girlfriends and later my first wife.

alwayshave
03-18-2021, 07:44 PM
Started wearing my mother's and sister's clothes when I was 5ish years old.

mbmeen12
03-19-2021, 12:14 AM
I wish I had 5 bucks every time I'd see "THE" question lol. Ill bite, 12 yrs old apx give or take and wearing panty hose found in the laundry.

HelpMe,Rhonda
03-19-2021, 03:18 AM
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!

cosmolovesph
03-19-2021, 04:27 PM
I was probably around 7 years old and as a kid in the 70's into the 80's and the great time of Pantyhose everywhere (including mom wearing ) I was draw to the great tan nylon and once I got my hands on some (might have been laundry or discarded pairs dad used for gardening) I was in love. It evolved from there but mom was short (still is) and I had to get my own and that was probably in my later teens and just got more into women's clothing since. The first time I was able to wear some heels with pantyhose, I knew it was part of me and never looked back.

Genifer Teal
03-19-2021, 08:38 PM
I had a really short teacher in 6th grade who wore really high heels to compensate. I was super curious how it was possible to walk in them. I mastered walking around the house in six inch heels in about a month. I quickly got bored. I wanted to go out and walk further in them. I couldn't do that without completing the look. That's how it grew.

Angela Marie
03-20-2021, 06:13 AM
I started by wearing my mothers tights (now called leggings) was I was about 10. Immediately hooked. At almost 67 they remain my favorite article of clothing.

Jill_cd
03-20-2021, 10:54 AM
My story is very similar to most. When 7 or 8 I started wearing my mother's slips. The feeling of silk against my skin was indescribable. It wasn't enough and I eventually began wearing my sister's panty hose, high heels, and dresses. The rest is history, as they say.

Karren H
03-20-2021, 11:20 AM
I got started when was 11 or 12 and tried one of my mom’s bras that I found in the clothes hamper. After that first time, I would regularly check the hamper to see if there were any bras I could wear. One time she caught me wearing one, but didn’t make a big deal of it. I was extremely embarrassed at the time, but not enough to ever stop.

My wife stopped putting her bras in the hamper because she thinks I would be in there trying them on... But I wouldn't... again... they are too big and she has really ugly bras... lol

Lacey New
03-21-2021, 07:31 AM
I think the seeds got planted in my early teenage years. Biology took over and I started to take an interest in the opposite gender. And back then girls wore short shirt to junior high school and it was not uncommon to se a glimpse of panties when one of the girls behind me sat down or got up from her school desk. I would imagine and wonder what was under those pretty panties. Well, I had a young mother and a sister who was only a year younger and we had a shared laundry hamper. And if I timed things right, I would usually have about a half an hour alone in the house after school. One day, I went to the bathroom and there was a pair of nylon briefs hanging out of the side of the hamper. So, out of curiosity, I put them on and the feeling was wonderful and exciting. Naturally, I took care of business. I felt guilty like I had done something completely forbidden and I said that I would never do it again. Well, that did not last long. Soon I was making sure I had that half hour alone as often as I could. Eventually, I got a little braver as well and figured out that if panties were exciting, then panties and a bra might be more exciting. It was. And eventually other lingerie as well. So, there was never any doubt that for me that dressing was a sexual fetish. The instant rush is gone, but it is still very sexual for me.

Misty_cder
03-21-2021, 11:58 PM
When I was in my early teens, my mother would hang her aerobics tights and body suits in my bathroom to dry after washing them. Late a night, I would go in and enjoy the feeling of the fabrics on my skin as I put the garments on. My plunge into expanding my dressing started when I lived on my own after college. I would frequent adult stores to purchase lingerie and got dresses through catalogs. Thinking back on what I had, I would say my look was more on the trashy side. It wasn't until after I told my girlfriend (now wife) about my dressing did my outfits start to change and become more acceptable for my body type and, more appropriate, age. I would also say my dressing first started out as a sexual release for me. As I've gotten older, dressing has became more of a way to release the stresses of my career.

BLUE ORCHID
03-22-2021, 04:24 AM
Hi Kim :hugs:, Around age 4 I started playing with Mom's Stockings & Heels, >Orchid **O:daydreaming:O**

patycd83
03-22-2021, 04:28 AM
I was started with my mothers clothing like thongs and bras.

Jane G
03-22-2021, 04:50 AM
I have two sisters and five female cousins that I used to play dress up with. What chance did I have.:heehee:

charlotte72
04-29-2021, 09:37 AM
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.

- - - Updated - - -

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

Lori Anne
04-29-2021, 09:55 AM
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
04-29-2021, 08:15 PM
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
04-29-2021, 10:31 PM
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
04-30-2021, 12:59 AM
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
05-01-2021, 08:53 AM
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
05-02-2021, 12:18 PM
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
05-02-2021, 12:43 PM
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
05-06-2021, 02:55 PM
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
05-07-2021, 06:24 PM
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
05-08-2021, 06:58 AM
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
05-08-2021, 12:19 PM
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
05-15-2021, 05:53 PM
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
05-15-2021, 08:21 PM
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
05-15-2021, 10:26 PM
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
05-16-2021, 01:41 PM
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
05-17-2021, 09:04 PM
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!
05-18-2021, 10:11 AM
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
05-18-2021, 10:33 AM
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
05-18-2021, 02:01 PM
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
05-18-2021, 10:39 PM
That could be my story. Oh, this started so,young.

Lori Ann Westlake
05-19-2021, 04:35 AM
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
05-21-2021, 10:03 PM
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
05-24-2021, 10:52 PM
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
05-25-2021, 08:32 PM
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.

HeatherW
05-26-2021, 04:38 AM
I was maybe 7, and my mother borrowed a dress from the girl that lived next door. Against my protestations, that and a wig she got somewhere became my Halloween outfit. At some point I remember feeling comfortable in the dress and wig and liked being pretty. As time wore on, 9 or 10 years old, I became aware that girls underwear felt better than boys underwear. When putting on my mother's underwear, I felt pretty again. Curiosity had me trying on her bras and skirts and looking at pretty me in the mirror. I've been looking for and at Heather in the mirror ever since.

shimmeryphantasy
05-26-2021, 09:09 AM
As far back as I can remember maybe 3 or 4 , all my earliest memories are of getting into moms and sisters drawers and putting on the soft things . Mom had a big drawer for her panties and one for her hosiery and one for all her wonderful nightgowns . When I was that little her pantyhose would cover my whole body over my head , I loved doing that . Her slips were so soft and slide over the hose and felt so good . Then I would put a nightgown over all of that and slide around in her bed rubbing the softness all over myself until I was pulsating with pleasure , I loved how it felt so much I would do it every chance I could. I loved how her slip would slide on her black panties if I turned the slip inside out so the softer side was sliding on the panties , I would always wear the nightgowns inside out so the softer side would be against my skin and I started putting on 3 or 4 nightgowns alternating layers so they would be super slippery.. It is 50yrs later and I have many nightgowns and pantyhose and wear them whenever I can.. I live in a small town so I have to keep it all in the closet but what a wonderful closet it is :)

Maid_Marion
05-26-2021, 09:14 AM
My wife suggested I start wearing women's clothes when it became obvious that finding age appropriate men's clothing in my size wasn't an option.
Turns out that women's XS or size 2 clothes fit amazingly well--with a little bit of hunting I can find clothes that fit well right off the rack without any alteration!
My waist at the time was 28 inches. With some exercise I can get it down to 25. Men's sizes start at 30.

The first really feminine clothes I bought was VS PJs. She was OK with me wearing them, but she, like many GGs, had issues with VS because nothing sold there fit her.
We had a talk and set boundaries.

Marion

DanielleCD
05-26-2021, 09:50 AM
Like many.. with my mom's stockings and then my sisters underwear.. I guess I was about 13 or 14 years old? I was so hard trying to be a boy but girlie underwear felt so different, and felt so nice and right. I spent many years confused, embarressed and hidden.

LindaSheer
07-16-2021, 07:18 AM
I started with Mom's stockings in the '50s. I was done for at that point. Lifetime wearer.:o

Gilly68
07-17-2021, 01:44 AM
My story is the same as a lot of other girls here.

My neighbours kids when I was seven or eight were all girls, so we would play house together. I remember me playing mum and stuffing things up my shirt to look more like our mothers.

When I played with action figures I used to pretend that the male ones would get magically transformed into the female ones.

First experiences of actually crossdressing was with my mum's clothes, like a lot of girls here.

When I was old enough to stay home alone whilst my parents went shopping, so maybe 12 years old or so?

I would go rummaging in her drawers and wardrobe, trying on bras, knickers, dresses, and my favourite thing was trying on her one piece swimsuits and stuffing socks in the bra cups.

I even remember trying on her lipstick and trying to make a wig from her knitting wool!

And carefully placing everything back exactly as I found it, and the worry she would notice things had been moved around :)

BustyOlivia
07-17-2021, 03:03 AM
I started when I was under 10 and used to wear my moms heels and dresses to feel pretty. Then later I put socks up my shirt and pretended to be a girl I knew. That was it for me then

MargaretJ
07-17-2021, 06:50 AM
My earliest memory of cross dressing was when I was 4 or 5, and trying on my mum's open corselette with suspender hooks, and high heels. Since around that age I have been fascinated with stiletto heels and stockings, and I generally will only wear heels. I would usually only wear tights and sometimes panties till I was around 12, then I started to wear my sisters clothes. My cross dressing would come and go, but the last 12 years or so after buying my first wig and breast forms, and using make up, I am well and truly in to it now.

Maria 60
07-17-2021, 06:52 AM
I shared room with my sister and she was a slob, and I remember that morning like it was yesterday. There was a pair of pantyhose on the floor next to my bed, my sister had left the house early and I put them on and went to town with them. From then I started staying in bed later then her and just would sneak more and more things under my sheets. I could still remember the rush that morning I put on her pantyhose and a white slip, the feeling was unbelievable.

NickieWild
07-26-2021, 06:00 PM
I went back and forth from a youger age ( around 6 or 7), with my mom and aunts clothes. Later I bought myself some lingerie but it never stayed. It always come in waves, sometimes i dont feel like it, other time I do. But now i am well equiped ! 😄

NewSally
07-26-2021, 06:08 PM
Similar story for me, as I began by rummaging through Mom's dresser of the laundry hamper, and trying on her pantyhose and bras on occasion when I was entering puberty. From then on it was very hit and miss, and later in life when I had girlfriends I would sneak some of their lingerie to play with. Always on the DL, though. Never had the courage to tell anyone I was dating (including my now wife) about my desires in that regard.

GiovannaBotta
07-29-2021, 02:45 PM
I had an aunt that I stayed a lot that was a boot lover... high heeled boots mostly. Don?t know why around 8, 9 years old started wearing them while alone at her house. Then it was mom?s clothes and shoes (always the shoes) and soon makeup, dresses, clip-on earrings... and there goes 30 years!

kimdl93
07-29-2021, 03:50 PM
Depends on what counts as the beginning. My earliest inklings trace back to mental images from when I was perhaps three or so, very young, remember trying on an older sisters slip, and around that time, some recollection of being teased for doing things girls did?not sure what those things were, but the message was clear. I suppressed that as much as I could into my teens. Then I spotted a younger sisters pantyhose. Then some 30 years of little more than a pantyhose fetish, with the usual denial, attempts to quit, and repeat.

Somewhere along my mid 50s I found myself curious about venturing further - prior to that I had always assumed I just could never dress fully and presentably as a woman. I tried on a few things that belonged to my then wife?and wasn?t appalled by how I looked. I got some make up, a wig and some breast forms?and it just clicked, I could do this. And I wanted to do this.

Jennifer2918
08-08-2021, 06:01 PM
I was born in the mid 60?s and one of the first things I remember being truest enjoyable was the streaking fad of the late 60?s / early 60?s. Fast forward a few years and I was going to take a shower and found mom?s pantyhose hanging to dry. Well, I tried them on and that was it I was hooked.
In high school, for a Halloween party senior year, I borrowed a girlfriends cheer leading outfit. It was a great time. I should say one year I wanted to go out trick or treating as a girl and mom was firmly NO.
Anyways, junior high and most of high school was the streaking thing, it from the early 20?s I would ?borrow? my girlfriends lingerie.
Then thinks went quiet for several years (maybe 10 years or so). No dressing.
Then about 10 years ago it came back full force.

BustyOlivia
08-08-2021, 06:52 PM
Being raised by women, I think I always wanted to be a girl. Started wearing heels when I was 7 and then dressing around 12. I?ve gone through long times without being Olivia, but now I know we are the same person, I am Olivia, I just only look like her sometimes but I can feel like her in my imagination in those times where I can?t physically transform. Now I?ve come so far with breast forms and beautiful wigs and a wardrobe with some heels that I am the best version of me I?ve been even though it?s been decades!

TexasLegs
09-16-2021, 07:35 PM
I've thought a lot about this. I grew up with 2 sisters but they didn't have any influence on me. For example, they never dressed me up and I never wore any of their clothes.

It was my mother. Her and my father were swingers. She had all types of sexy lingerie And my dad had all the magazines like Hustler, Playboy and Penthouse. I found women in stockings and garters hot as hell. I'd masturbate to their pictures all the time in my teens. At some point, alone in the house, I snuck in to my mom's drawer and got her stockings and garters. At 13-14, I was too young to have a girl and I suppose the idea was just to put them on myself.

But it never went further than lingerie until I was divorced in my 40s. I finally had money, a place to my own and one thing led to another until I was a full blown CD with thousands of dollars of clothes, makeup, shapewear, silicone breasts, wigs, jewelrly, shoes, etc.