What was the first item you wore?

[JackieD85]

For me, it started when I was in elementary school (I dont remember the age) with my mothers panties.

[CharlotteCD]

I can't remember exactly, but one of my earliest memories was being confused and scared by my body's reaction to my sister's underwear. I would guess it was either wearing that, or it was my sister and her friends dressing me in her dresses when I was about 4 or 5.

I know for sure it was tights, or a bra or anything like that. I didn't discover those until much later. My dressing interest moved with my sister's age progression as she was my size, and dressed more my age than my Mum, whose stuff I never wanted to touch.

[~Joanne~]

Pantyhose. I didn't understand the allure of them, still don't, but found they were/are absolutely amazing to wear. All of my outfits start with the hosiery.

[Raychel]

that would have been panties or a girdle for me, Soon followed by pantyhose
A slippery slope from there :heehee:

[Kris Burton]

My wife's nightgown. I put it on as a joke to her. After the laugh, she asked if I liked it. I said no. I lied - big time. I had a few occasional skirmishes with her pantyhose over the years as well, but it was not until I got my own articles did things really take off, and now here we are.

[SophiaRose]

Sister?s panties when I was about 9. I vaguely recall wearing a one piece bathing suit at 8 yrs old but that memory is a bit murky.

[sara66]

My mom's bra when I was around 4-5.
Sara

[Crissy 107]

My Moms panties at 11-12 and like Raychel said, a slippery slope for sure.

[Fiona_44]

My mother's girdle.

[Elizabeth Marie]

My mother's nylons when I was about 5.

[Maria 60]

I believe my first time was when I was sharing room with my slop sister. She left a pair of beige pantyhose on my bed post. All I remember was seeing them and I tried them on and there was fireworks going on under those sheets. I believe the same fireworks are still happening up to today when I put on a pair of pantyhose

[tbryant2k16]

A pair of my mother's panties when I was 8 or 9 years old. From then I got hooked. It was just something about them that I liked.

[NancySue]

At 5 or 6, one rainy day, I was invited to join neighbor sisters for some ?dress up?. At first, no interest, but did join them. Nothing happened until I slipped on a pair of pantyhose. Wham, Bam, 💥 I couldn?t believe it. Next, I tried on a pair of sheer nylon stockings. That started it. Like Maria, to this day, Wham, Bam.

[sandy_folsom]

Middle school. I was a latch key kid with both parents working during the day. One afternoon I tried on my mother's calf-height boots and it felt very sexy.

[Georgina]

My mother's slip at about 8 years old.

[JulieC]

The first item I wore was my mom's pantyhose around age 8-9. But, the earliest memory of the desire to crossdress I can trace back to around age 5, wanting to dress like catwoman.

[Jessica S]

I was 5 yrs. old. I was helping sort the dryed laundry and had for my moms kneehi's ask what are these and then just put them on. the felt great. It didn't take long to look for them again and found pantyhose. My mom kept a bag of old pantyhose in a closet right across from the bathroom I raided all the time. The of course the silky slips and panites that hung to dry in the bathroom I tryed on next. Everything was big but I grew into her tuff between 10-13 yrs old. When I 12-18 yrs old and left at home alone I wore her clothes that I could fit into.

[Sometimes Steffi]

Mom's panties, and then it quickly progressed from there to girdles, My mom didn't wear pantyhose at that time. Just carter stockings attached to the girdles.

I never knew how to put on stockings until I saw Lauren Bacall put them in in a movie.

[Toni in nz]

My sister's one piece swimsuit it fit really nicely when I was around 6-7 yrs and got caught by my sister she made me take it off but never said anything to my parents, then a few months later I put on my mums nylons and it got me thinking there's something wrong with me because it felt normal to ware female things , I was totally confused but I couldn't ask or tell anyone how I felt.
It wasn't till I found this site, stared reading articles from people here and realised I wasn't alone that was about 9 yrs ago, I was 56yrs old.

[DanielleDubois]

When I was 10 or 11 I discovered a lace up corset style girdle and a beautiful mohair sweater dress in a cedar chest in the basement. Tried them on and the rest is history. I have never figured out why those two particular items were stored in the chest because the only other contents were some old old newspapers and random financial paperwork.

[DavynaCD]

For me it was my sister’s suspender belt and stockings that I “discovered” in her drawers when I was 8 or 9. My love of lingerie was born and the rest is history.

[Visitor]

The first item I wore belonged to a curvaceous next door neighbor I'd been ogling all summer as she mowed the lawn in short shorts and a halter top that was overflowing. I was twelve when she asked my mother whether I might be interested in babysitting for her 7 year old daughter. It was agreed. When I arrived the girl was already in bed. The couple departed and with a racing heart I went into their bedroom and searched dresser drawers until I found her lingerie. I was about five feet tall at the time so I had no difficulty putting on a bustier with cups formed by a layer of foam rubber. I stuffed the cups with panties and was in heaven. Over that winter I played my games often, even putting on lipstick. One night my mother came to check on me. Fortunately I'd locked the door so had time to wipe the makeup off and get dressed. I told her I'd fallen asleep.

It was a very exciting time for an adolescent boy to be indulging in these erotic games. The rest is a VERY complicated history.

[bridget thronton]

Mother's heels

[kayegirl]

Sister's one piece bathing costume, aged 5 or 6. Still have the photo that my Dad took of me happily playing in a public paddling pool. There may well have been earlier stuff. I often wore some of my Sister's hand downs, although not dresses or skirts, but the swimming costume was the first memory.

[Debbie Denier]

My mothers sheer tights/ pantyhose . They were 15 denier tan shade. The feeling was electric. There was no turning back from there.

[Tanya silk stocking]

My mams old rockabilly under skirt

[Genifer Teal]

Probably high heels. I needed panty hose to help them fit. First outfit included a black suede skirt that was tight at the legs. I liked how it limited my stride.

[Abby-Becca]

I don't know if this counts, but I would 'fashion' my own skirts and dresses, as a three to four year old toddler, out of things like towels. Mum and dad worked in a infant / primary school, so, even though I wasn't old enough to go there, I could still play with the toys after everyone had gone home, I would dress in the fairy and princess outfits - dad looovved that - not! I got into so much trouble for it.

[Lacey New]

A pair of my mothers nylon granny panties out of the common laundry hamper. They have been my favorites ever since.

[alwayshave]

I am reaching back to when I was 3-4 years old, but I believe it was my mother's Merry Widow.

[SophiaRose]

Merry Widow? I had to google that. Now I want one!!

[susan2010]

4 or 5 years old. My older sister's full petticoat. I loved it!!
And I still have a "thing" for petticoats 65 years later.

[krissysSecret]

Not sure exactly, but I was in grade school. I put on my sisters swimsuit..loved it! She was in ballet classes so I tried on her ballet outfit..it had a poofy skirt that got me pretty excited. Ah..the good old days! ��

[danniUK]

Hold-up stockings that my then-girlfriend bought me for a schoolgirl fancy-dress outfit, almost exactly 30 years ago!
I still have a photo somewhere... ah, the beauty of youth!

[Harriet14]

My auntie's long-line bra, girdle and tan nylons. I was about 14. I still love lingerie of that era. Harder to get now, though.

[CarlaWestin]

Mom's bra.

Next question, please.

[ColleenA]

Age 9 - a pair of black lace panties that must I must have somehow gotten from one of my older sisters. Would wear it under the sheets at night.

[Leah87]

A pair of my older sister's knickers when I was 13.

Some years earlier, I had been delegated the job of emptying our clothes from the tumble drier and putting them into individual baskets for my younger sister, myself, and my older sister. I hated it.

But just when the job started to get really interesting, my older sister decided that she no longer wanted her younger brother handling her underwear. Great while it lasted.

[Cheryl T]

My mom's white nylon panties when I was about 5.
Somehow it just felt so right, so natural. Soon after that I wore them and her bra. Then of course I began wearing stockings, a dress and heels.

[JesseVF]

Definitely Mom?s bra at around 5 - quickly followed by slip and girdle - strangely never had desire for actual clothes until 40 or so years later.

[KrissyTN]

My Mom's bra ....quickly followed by panties and pantyhose. When I discovered a swimsuit she had with built in cups....heaven!!

[Celee]

Mom?s bra quickly followed by panties. The best was when I found my moms girdle.

[Stephanie47]

It was one of my mother's white nylon full slips. She use to dry clothes in the apartment on a washline that ran the length of the hallway leading from the living room to the bedrooms. I loved the feel of the nylon. At first I would fondle the slips and eventually took one down to try it on in the bathroom. Full slips were my gateway drug to women's clothing,

[Aubrey Cane]

Pantyhose at the age of 8, have been wearing pantyhose ever since and wear almost daily and it is the staple item when i dress.

[Steph_CD_62]

I remember being caught by my mom when I was probably around 5 wearing her panties.
Not sure why I did it and can't even remember if I enjoyed it. Just remember being caught.

[KrissyTN]

Mom?s bra quickly followed by panties. The best was when I found my moms girdle.

Celee,

Agree!! When I spent a summer at my grandmothers and discovered some Playtex all in one girdles - with garters she kept downstairs amongst some discarded clothes - it opened up a whole new world!!

[Megan b]

It all started with a pair of my Moms sun tan pantyhose. I was around 12 or 13 years old. That was over 40 years ago. After the hose came panties followed by slips and girdles and lastly a bra. Next would be a dress and shoes. I'd have to wait till my 30's before I'd get a wig and breast forms.

[Toni B]

Suntan pantyhose

[Celine 9]

A dress that ordered from the JCPenney catalog along with a black DD bra.

[Alice92]

When I was little I was too afraid of being caught so I only tried on my mother?s stuff that I could put over my normal clothes and quickly remove like her pumps (too big), a fur coat, a scarf, gloves and a hat. Then I became more reckless and I started putting skirts or dresses over my clothes lol

[Girl]

My mother's nightgown.

[Christina C]

A satin and lace night dress that my boyfriend at the time bought me.

[Kelli_cd]

First for me was probably my grandmother's petticoat. I was 4 or 5. Then, my mother's girdle. When I was 11,I tried my sister's nylon bikini panties. Been hooked ever since.

[Christina89]

I was about 12 years old when I first tried on one of my mother?s bikini. After that I loved the way they felt on my body and then tried on a collection of her clothes. I can tell you it was a moment I?ll never forget. After I tried on a skirt and top of hers, I saw Christina in the mirror that night smiling that she had been freed.

[Michelle1955]

Panties around 5 years old.
One of my friends that I played with lived on the same block.
She and I were plying in her bedroom and we switch underwear and panties while playing.
But had interest in female cloths before that.

[Claire M]

My sister's panties ... still remember the first time vividly. Cotton briefs, white with little blue flowers and little loopy trim around the leg openings. Remember seeing them lying on the bathroom floor and had this overwhelming need to see how it would feel to wear them. Same curiosity led me to try on her bra a few weeks later ... then a skirt and sweater ... then ..........

[chrissy111]

According to my Mother, the first thing I wore was a diaper when I was born.

[AllieBellema]

For me, it was a Poodle Skirt halloween costume that I bought at the local K-Mart. I was gonna go big for my first time wearing something femme.

[Sometimes Steffi]

According to my Mother, the first thing I wore was a diaper when I was born.

Was it pink, blue or white?

[CDMargret]

Nylons. Mom's nylon pantyhose. Then my sisters ballet outfit and on and on....

[rachellegsep]

Moms Corselette with black seamed stockings.

[Linda E. Woodworth]

Mom's pantyhose, I was fascinated with nylons.

She even had a pair of "Beauty Mist" in the open box that I tried. Hell, if they were good enough for Joe Namath?

[Deborah G]

My sister's panties. All my firsts...heels, hose, dresses, skirts, flats and Keds were right from her closet. So nice we wore about the same sizes!

[CarynPB]

One of my other's slips...soon followed by most of whatever was in her lingerie drawer.

[Bruce64]

A panty always panty

[Angela Marie]

My mothers tights (which would today be called leggings). I was about 12, so almost 60 years ago.

[MarinaTwelve200]

My mother's red lipstick when I was 12.

[Jennifer_Ph]

L'eggs Sheer Enegry Sheer To Waist, Suntan, from an egg! Still my favorite today!

[tiffyjo]

Mom had a "rag bag" upstairs in my closet and I found an old pair of her panties in it. I tried them on when I was probably about 8 or 9 and I was hooked. I almost wonder if maybe she wanted me to find them. I almost bet she knew I was wearing some of her items. Memories!!!

[BrendaPDX]

I am with Jennifer, "L'eggs Sheer Energy Sheer To Waist, Suntan, from an egg!". Loved the way they made my legs look then and love them now!

[cpt2669]

Was my mother's one piece bathing suit. Was 10,11 or 12 not sure. To this day one piece bathing suits are my favorite fem clothing to wear.

[Ann Simpson]

my older cousins yellow cotton briefs. I snuck them out of her dresser drawer. I don't know why I did it.

[Monique65]

My mother’s open bottom girdle and stockings. I slipped them on and my life changed.

[BrendaPDX]

Like a lot here, pantyhose from my sisters dresser.

[Jane G]

Not even certain what I wore first. I used to play dress up with my cousins from a young age, every one a girl. Certainly by junior school I used to wear girls panties. Those navy blue ones. Basically, as I grew up I would wear whatever my elder sister wore, whenever I got the chance. Mum and dad never approved to their dying days.

[Freddi]

One of my mums skirts and tights. No other girls in the home when I was growing up but I'm told that when I was 4 or 5 there was a girl similar age lived 2 doors away and we would often swap cloths and toys......her my Action Men, me her dolls.

[CDJessica4U]

My mothers pantyhose and her winter knee high boots. I would get very aroused.

[NjJamie]

Jackie, a bit complicated but I remember being dressed up as a young girl for a Halloween party (8 yrs old?) at the church but the first time I did it for myself was a few years later (11 or 12). I was occasionally sleeping in the extra bedroom and for whatever reason, looked into the closet and found a bag of older pantyhose and the black go-go boots I wore to that party, put them on and the rest is history.

Within a few months, I was using any chance I had to try on everything I could, even occasionally faking that I was sick to stay home. Starting the moment I was home alone I would shower and start in nightgowns, etc., working up to business type outfits and dresses as the day wore on.

I clearly remember every "first" from that day on, first makeup or nails or stockings or stepping out the back door and finally stepping out the front door and driving away.

[Misty_cder]

The first item of woman's clothing I wore was my mother's light blue one piece leotard and white tights. She would wear this outfit when she went to aerobics class and then after washing it, hang it up to dry in the bathroom I used.

[Allieboy]

I very clearly remember at the age of 5, I had just had a bath and my mother was getting me ready for bed. She realized that I did not have clean pajamas or underwear as the wash hadn?t been done that week. She asked my aunt, who lived with us, if she had any small panties to put on me. I remember they stood me up and put the panties on me and they giggled and remarked how cute I looked. To have never forgotten this episode of the first time I wore panties surely had an impact on my life long desire to crossdress

[Traci H]

Somewhere around age 8, I was at a friends house with my family. My friend and his older sister were pushing me to try on his sisters shoes, some low heeled flats. I did slip them on and they tried to drag me into the room with the adults thinking it was funny I was wearing girls shoes. I got them off, but the incident always stuck with me. I enjoyed wearing them and still do!

[Jessielle]

Hi. My first was from my mom, a black lace bikini panty when I was 11. Memories.

[krissy]

i wore my sisters pink panty slip it was short and lace accents around the bottom i loved that slip i felt so pretty when i wore it :daydreaming:

[CynthiaD]

I really don?t remember, but it was either my mother?s panties or one of her slips. Or both. I started with red nail polish at the age of three. I was 12 the first time I dressed fully en femme. Bra filled with socks, panties, slip, and a discarded dress of my mother?s. No wig though. My short hair made my appearance somewhat disappointing. I sometimes would wrap a towel around my head and pretend I was a nun. That solved the hair problem.

[Mr Quirky]

My first outfit was a gymnastics leotard, i now have 35

[Cross1976]

For me it was aged probably about 5/6 so the early 80s, mother always wore tights, grey, barley black or tan, loved them, she never stopped me either, obviously the older I got the more it was frowned upon and soon became a secret.
Now latter in life still love dressing, wife knows but I have to do it when she's not around, wish she would let me do it with her but that's life....

[CDJoyce]

A pair of my sister's panties. They looked like ones worn by a topless model in the newspaper. So I tried them on and my crossdressing started from there,

[Cross1976]

I don't and never will be able to look like them. But the lingerie that they wore always made me want to wear and look like them!

[Leohose]

I am with Jennifer, "L'eggs Sheer Energy Sheer To Waist, Suntan, from an egg!". Loved the way they made my legs look then and love them now!

So true the early commercials enticed you to slip into their pantyhose

- - - Updated - - -


The first item of woman's clothing I wore was my mother's light blue one piece leotard and white tights. She would wear this outfit when she went to aerobics class and then after washing it, hang it up to dry in the bathroom I used.

Yes same except it was a black leotard and white pantyhose that were like tights soo amazing

[BaliGirl]

The first thing I tried was one of my mom's bras when I was 12 or 13. I went into her lingerie drawer when no one was in the house.

[tmannref]

When i was about 12-13 i would slip into my moms panties and bra and stockings when everybody was out of house on a saturday. Loved the feeling of the stockings and i would stuff the bra as
mom wqas about the same size i was but well endowed in the chest area . Occasionally i would add a dress and heels

[MsEva]

I think the first thing that I can say was totally fem was a Merry Widow corsolette that the former owners of our hose left behind in a hope chest. The corsolette was left I guess for hopes of a wedding event that never happened for the former occupant. I love the satin feel of the fabric. I was over the moon with the feeling.

[audreyinalbany]

I am a total Boomer.... first time I tried on was my 1950's Mom's rubberized girdle, the ones with the built in hold ups for stockings. I tried the stockings on as well and (probably) one of her pointy bras, but I don't remember that quite so vividly Pretty sure it must have said "PLaytex" on it somewhere.

[crissy7]

My sisters red bra and panties.She had great clothes that i wore till she moved out.

[SaraLin]

It was so long ago that I'm not sure, really, but was probably one of my sister's dresses.

I was really young (6 or 7, maybe) and to me it was about trying to look like a girl, not so much about the feel.