first article of women's clothing that u tried on

[LitaKelley]

First my sisters satin panties, then her tights and leotards. I forget my exact age, maybe tween or early teen, not sure

[Mistybtm]

For A school play I had to wore green tights when i was about 9.:o then in my young teens moms pantyhose and bras.:battingeyelashes: and it just snow balled from there.:D

[CalamityJane]

Some lovely suede ankle boots....and then it just all progressed from there.....over the many,many years:-))

[silkihose]

The first time was around 5-6 with my mothers pantyhose,sheer energy control top in suntan.

[briannaluvCD]

The first article of women's clothing that I wore was my moms shoes. sounds sick to me now but that was the beggining of my journey. It progressed to x-girlfriends panties and bra's.

[rachellenicole]

The first thing I tried on was my mothers High Heels, then my next adventure was trying on her panties, bra (Which was huge) a girdle and stockings then a slip and her heels, then proceeded to parade around the house.... This was magic for me, I was about 6. I progressed to raiding my cousins panty drawers and acquiring lingerie any way I could.

Rach

[Jay Cee]

A bra. Not sure who it belonged to - I just know that I loved the feel of it. That was probably 30 years ago now. Geez, that's a long time ago. :)

[Jilmac]

Actually for me it was girls clothes. Acousin of mine dared me to wear panties and a dress when I was around 7 years old. I don't know to this day where he got the girls clothes from because ha had all brothers, but the minute I felt those silky smooth panties next to my skin, I was hooked

[aggi123]

Mine was a swimsuit in a game of truth or dare a long time ago. I think I was about 9

[ladyinblack]

for me I think it was a pair of my moms panties a short jean skirt a bra and a bright pink blouse with pantie hose and a bright pink pair of high heels

[KatieV]

I must have been only 4 years old; my mother had a clothes hamper in the bathroom of our small apartment where she kept her nylons. Not pantyhose but seamed hoisery. What led me to try them on I'll never know; I do remember that they carried the scent of her body which I found to be very evocative. I was hooked.

[Jamie.cd]

The first article of clothing I can remember trying on was my mum's pantyhose. I think I was about 4 or 5 years old.

[Gina X]

The very first girls clothes I wore were from the dressing up box when I was about 4 and I always wanted to be the fairy, then when I was about 6 my mum and I were staying at some friends and and it got too late to go home so the friend gave me a nightie of her daughters to sleep in. Then when I was about 10 I started to wear my mums panties and it was downhill from then on and that was over 50 years ago now.

Love GinaX

[herwannabe]

My mothers Bra and panties only problem was she was 44dd and I was skinny as a toothpick took a lot of padding to fillerup ;-)

[Emma Leigh]

It was my mothers slip, my sister and I used to get into our parents bed at the weekend, and I put on my mothers black slip,it did,nt go down too well,I dont know why I did it, but done it ever since those 8 year old days,and with no regrets either, you are what you are!!!!

[Susan Thomas]

I think it was when I was 11. My sister's panties and then her bathing suit. My mom came home from getting groceries and I was caught red-handed. It is funny as I didn't cross-dress again after getting caught for ten years. Fast forward ten years:I was at my in-laws house for the weekend. I was getting out of the shower and hanging on the door were my mother-in-law's pantyhose. I couldn't resist and slipped on the pantyhose. Now I am sitting here typing this message wearing a bra and panties!

[winny]

I was about 5 years old when I tried on my mom's heels... I remember how nice it felt to wear them... There was no cd activity until I was 23 and in college... I found a pair of bikini panties in my laundry basket as I was folding my clothes... A female co-ed must have left them in the dryer... Tried them on and was hooked! Wow that was almost 20 years ago and am still hooked on women's clothes....

[Kelley Girl]

Nylon panties, I love it.

[Terry V]

I wrote about this before but I love the story. My Aunt caught me trying on my cousins panties and asked if I liked wearing them and I said yes and she asked if I wanted to see how I looked as a girl and when I said I did she let me dress in a yellow Easter dress and from then on I loved to dress as much as I could and that was over 50 years ago and still going strong

[Sophie86]

First item was a pair of my older sister's panties. My mom made me wear them because I didn't have any clean underwear. I was probably around six or so. Next time was when I was about 10. My older sister talked me into dressing up for Halloween. She dressed me in one of her dresses, a bra, pantyhose, and boots. IRRC, I drew the line at wearing panties. It was two or three years later that I started dressing for my own amusement. I started with mom's and older sister's panties, then bras. I branched out from there into lingerie, dresses, and pantyhose.

[krissy]

my sisters pink panty slip with lace trim and my moms mini skirt and her red bullet bra

[Loretta]

For me, it started when I saw a pair of red flats in my mom's closet at the age of 12 or 13. Red was my favorite color, so I figured that they would look good on me. I walked around in them a bit, and found them to be very comfortable. I wondered that if Women's shoes felt this nice, what else would of, So I put on a white skirt, a red tube top, a pair of black pantyhose, and I was hooked.

[Tiffany2]

Not really sure, I think it may have been panties, I love the way they feel, especially the microfiber now.......

[xdresser4u2dressup]

you could say I didnt try it on but had no choice , I remember when I was little I ran out of clothes cause the washing machine was on the fritz and my sisters had to put me in one of their dresses . Since then Ive been hooked , then the second was pantyhose as i loved the tan legs my sisters had as mine were always white .

[G.Grace]

It was my sister's uniform. It was a black, blue and white plaid jumper with a white shirt and white panty-hose.

[larissa-laurie]

Mine was my sisters school uniform too, only she had me go all the way at once. It was fun hooking up the nylons to my long leg girdle. Her bra fit perfectly, slip, blouse and skirt and vest were perfect too. She was like a makeup artist and made me really look like a girl especially with her long haired wig. I couldn't believe the transition in the mirror. My feet were too big otherwise I would have had her pumps or heels on too. We tried this 3 nights in a row. I have been hooked ever since but it hasn't been a cakewalk getting the chances to dress up. I just don't understand how I like the feeling so much of dressing in slippery lingerie and wearing skirts or dresses with heels.

[Carey2bcd]

Like most I guess, it was my mothers bra, panties and lingerie. I remember she had a cute sequin dress I tried on, I just wished it would of fit better I was probably only 12 or so. Can't forget the heels, I loved wearing her heels.

[RachelF]

Wow, believe or not, I am not 100% sure. I was 12 to 15 years old (47 today). First things were sister´s underware, I think the very first ones were a set of yellow panties and bra and pantyhose. After several sessions I was caught by my mother and never tried again until few years ago. I restarted crossdressing with my first panties: a black thong.

[Lorna]

What surprises me is the number of people who say they began when they were very young - anything from 3 to 8 or 9 years old. I didn't start until I was about 13 or 14 and by that age my size was not hugely different from my mother, so I could try on her clothes (I had no sisters). Had I started when I was only 5 or 6, all of my mother's things would have been far too big for me, yet plenty of posts in this thread talk of trying on mothers' bras, stockings, panties, etc at that age.

[Marilyn Beck]

My mother's bra, when I was about 12 years old. It was hanging up to dry in her bathroom one day and I couldn't resist trying it on when nobody else was home. I never had the nerve to raid my mom's dresser drawers or closet.

[hayley_babe]

my first piece, and i was probably around 14 or so was a one piece bathing suit, it felt so nice on me and from there i plucked up the courage to try on both panties and bras before moving onto the whole deal later on...it was so fun back then.

[Maria 60]

sharing room with my sister was great, it was a long time ago but i remember the first thing was here pantyhose, what a feeling. Then my mothers slips. They were great together.

[Lucypink]

My oldest memory is of me with a nice girl dress when I was like 5 Years old, at a my parents friend home, I remember dancing with their daughter, both dressed with Flamenco dresses.

[HairyBethCD]

I'm told I used to raid the washing basket for panties from about 3 but my first conscious wearing was my sisters panties and stockings when I was about 12 or 13. I started buying my own when I was about 15/16. I was staying with relatives in a different part of the country so felt anonymous and bought a bra/tanga briefs/suspender belt and stockings, all in white. It was wonderful!

[Timycd]

The first ... I think my mom's high heels and after her pantyhose and a red summer clothes

[Melody Phillips]

my older sisters bra and panties. I guess i was around 12 or so when i "got the calling"

[Roxanne_Alternate]

Technically it was when I was around 5-6 years old I think, when I'd play dress-up with a friend of mine. I sometimes wore skirts then. After that, I started trying on my mom's clothing at around age 12-13. But then I outgrew my mother and because I had no sisters, I pretty much didn't dress up for quite a long time. Now that I buy my own clothes, it's not much of a problem anymore.

[RachelDenise]

It was my mother's bra, followed by her panties and a girdle. Eventually tried on her pantyhose too.

[NikkiW1971]

a long sleeved leotard. It's still my fave garment

[HeatherKirk99]

For me, it was my mother's pantyhose when I was about 4 years old. I have no memory of why, just went and put them on one night, and went to bed. Then nothing until I was about 11 or so, at which time I rediscovered her pantyhose, and high heels this time. Also a very long halter dress.

Ahh, those were the days...I could wear heels that were in an average women's size (7 or 8 I think).

[Brendastevens47]

Age 11, my mom's silky white full cut panties. I so wanted to put on a dress when I was about 5, but resisted until I could not resist anymore. Off the clotheshorse the panties went...and oh my...the feeling and finally being the girl I am. I never stopped from that point onward, then started to wear a bra with slips and nighties and wearing nylons and dresses by my early 20's. Still cannot resist a lovely silky pair of girly panties....that is just the girl in me...hugs..Brenda

[wildman2]

Wife's bathing suit thongs. they actually fit okay and i liked the tight feel around my ****.
then it was panties - both thongs and full back.
i loved it.

Her pantyhose did not fit so eventuyually i went out and bought my own. That was fantastic.
i did not like the bikini tops - they did not fit at all and i thought looked ridiculous.

Last year i forgot my male thongs for my trip to St. Martin so used her bikini thongs at the beach and pool. I loved that!!

[wildman2]

Are you still turned on by wearing these items? I am.

[Noemi]

My Moms Panties, and a 60's type girdle than bras. Love panties have been wearing them 24/7 for years. This is a powerful thread. I can smell the perfume.

[Annabelle1962]

For me it was a pair of my grandmothers bloomers as I had wet the bed and my pajamas where wet so I was put into them by my mother. The first things I actually tried on of my own chosing was a bra, knickers, suspender belt & stockings of my mother. This then led on to my sisters gymnastics leotard and dresses.

[regina young]

I used to be packed off, along with my brother to stay with an Aunt and Uncle during the summers. One Sunday morning I had no dress shoes so my Aunt puts me in my cousins Girl Scout shoes. And with very few underclothes she also used to put me in my cousins panties, except she called them step-ins back then. I t was tough being the youngest and the littlest. Still like those step-ins though.....regina

[KayleighMadison]

For me it was my mothers panryhose just because it was the first thing in the drawer. Soon after I discovered her panties and bras. But it all changed when I found her heels. I have been obsessed with high heels ever since.

[munshine nightwood]

I can remember that it was a pair of my mothers high heels at the age of 4 with one of her purses. by the time I was 9 its all that I could think of. then at 11 I got my very own pair of panties and a bra, now I'm a female impersonater full time. I have started the next step of my crossdressing life, I'm working on starting to enlarge my breast and it is great!!!!!!!!!!!

[Traci Elizabeth]

If I could remember that far back in my life, I'd contact Ripple's! In fact, I think that when I started wearing woman's clothes folks were still dressing in deer skins and carried clubs and spears.

[charlene#2]

i remember playing strip poker with 3 sisters when we were all maybe 14-15 yrs old and we were all down to our skin and still playing and i picked up the older sisters panties and slipped them on,they were all nylon with the nylon gusset(too bad they dont make them anymore)they felt great and no one said anything about me sitting there in a pair of pretty panties.i hated to have to give them back when we quit playing poker.

[kate473]

Mentioning the one-piece bathing suit... brings back memories.

[neworleanssusan]

Pretty sure it was an old bra of my mothers....w-a-a-a-a-ay back a long time ago.

[kelliboots]

Boots!

[Feather]

High heels, way way way way way back though, and I just did it cause I thought it was a "fun" thing to do.

[sonna]

sisters panties

[MichelleOhioCD]

Bathing suit - ashamed to admit it was "borrowed" from a clothesline and I went for a late night dip in Lake Erie! (I put the suit back reluctantly)

[seatown9]

Sisters pantyhose...

[Vicky-m]

my moms panties and stockings/pantyhose and a really pretty sweater she had

[Tammy V]

It would have to be either my mother's panties or pantyhose. I was so young I cannot remeber exactly.

[JaytoJillian]

Hmmm, I must've been about five when I tried on a pair of my older sister's tights. The intent was to play "Superman," But the sensation was so super that I never got over it. Next was a few times in college, but I was just goofing around. I finally got the swing of this hobby in 2006, and Christened myself, "Jillian." And damn, I thought golf was expensive.

[Vspink101]

Sister's panties...I'm not sure what drove me to wear them but I can still remember how much softer they were than my underwear and how jelous I was.

[Rachel Mari]

My mother's stockings at 5yo.

[elle_2000]

I think I was 12 and I was home by myself. I went into my mom's closet and tried on a few of her dresses. At that time I had no idea what crossdressing was but I knew that I wished I had been born a girl.

[Michelle1056]

I came across a pair of panties that I tried on. For a while thereafter, those would be the only types of women's clothing that I would wear. I fell in love with thongs! Some time, I want to try other types (like bikinis).

Michelle

[gagina]

That would be pantyhose

[Rachael502]

At age 8 I first tried on Mom's black nylon panties.......The rest is history!!

[JustineFallow]

Pantyhose seems to be a common answer; no different for me, but as I mentioned in another thread there's a picture of me putting them on while I was still in my crib. Now you don't get much earlier than that, do you?

After that it was still pantyhose and nothing else until about 11 or 12 when I branched out into the other underthings. Out of mom's drawer, of course.

[Amy Hepker]

That would have been one of my sisters Dresses.

[GirlieAmanda]

First, I can't believe the ages of the people when they first tried stuff on. Further reinforcing my notion that the propensity for being a TG person is something u are born with. I first tried on my Mom's bra, pantyhose and burgundy leotard. I used other pantyhose to make boobs. Very vivid memory.

[PattiMichaels]

Pair of Grandmother' pantyhose when I all of 4 years old...kinda ironic, since I wouldn't be caught dead with anything but bare legs and open-toed heels today!

[Jennie1975]

My now ex-wifes panties and bra.

[Stephanie47]

The first article of feminine clothing I wore was a slip. My mom use to hang her hand washed slips in the only bathroom. At first I tried sliding into them as they hung wet. Ultimately I would put them on, wet or dry, and, then re-hang them. I loved the slinky feel of the nylon. Now I own numerous slips, full and half slips, in a rainbow of colors. I love wearing a lacy slip under a pretty dress. My favorites are lacy ones with shadow panel or double layers. My favorite color remains pure white.

[mscatie85]

At a very young age me and my sister use to play house and one of the things we did was put on our parents shoes. For some reason I always tended to choose the pair of black stiletto shoes. I could not have been more that 5 and I already knew I had a preference for feminine things. Too bad it took so long to realize what it all meant.

[Heather J]

The first item of Woman's cloths I tried on were panties

[patricia88]

I talked my mother into dressing me up in a "girl" costume for Halloween.

[rocktheplank]

The first item of Woman's cloths I tried on were panties

Ditto on the panties, I tried them on real quick while a gf was sleeping

[Samantha_Smile]

Mum's white satin bra. I'd have been about 13.
Mum, Dad and my brother had gone to town and I was alone and bored.
Tried it on from her underwear drawer. Only had it on for a minute when I paniced about them coming home finding me.
In the panic, I couldnt release to hooks and fumbled for a good 2 minutes before turning it around on me and un-doing it at the front.
5 minutes later, when I realised they'd be gone for hours, and had only been gone for 30 minutes, I was back in the drawer trying the matching knickers and the bra.
Then the matching suspenders too and some tan stockings.

So the very first was a bra, but in the same day I was up to full underwear.

The next saturday I went a lil further, more so the week after... and the rest leads me here :)

[Roberta Roberts]

Melinda,
In response to your post...I too am a girdle and longline bra person. I just do not feel properly dressed without. I really like the Playtex offerings but my preference is the 18 hour high waist long leg style, followed by the ICBIAGG, also high waist long leg and a truly great (but very tight..at least to me) double diamonds high waist long leg. I have a collection of girdles, ranging from: Rago, VaBien, Flexees, Miraclesuit, Cortland, and when available on eBay, Subtract. And for special occasion wear, I like the Custom Maid 299 and the 612 (both being super controlling and provides a very firm shape. One of my all time favorites was Cupid Duotrol, which had a 4" hi waist, double self reinforced panels for the tush , hips and triple reinforced tummy panel...crushingly tight when first putting it on but after 10-15 minutes, super smooth and firm but very comfortable even after 10 hours.

I also have an extensive collection of longline bras. My current favorite is the Elilia front hook style....I have a muffin top issue that needs much help. This is my reason for the high waist girdle and longline bra combination. It simply works for me.

RR

[katrinakat]

Pantyhose and tights. from there it progressed to everything.

[Tasha2633]

for me it was my sistes skimpy panties and bra. I felt so sexy. after that, i couldn't get enough.

[LauraEwing]

My sisters sandals, purple dress and panties.

[danielletorresani]

I tried a dress of my mother's on. Didn't do much for me because it was so loose fitting, but it was enough of a taste that I was hungry for more!

[Ashlee]

pantyhose at age 5 or 6. From there it just progressed. Still my favorite item to wear.

[sarah1992]

For me I think it was quite lucky, I was on a gifted and talented french course. We were put in groups and had to make some sort of Jermmy Kyle TV show and it turned out to be a cross dressing one so somehow I got voted in for being the CDer and well we found a white prom dress in my size in the props area, it was amazing

[khadivh]

at age 5, my sister's panties and flower girl dress from my aunt's wedding. to this day i still love the feeling of silks and satins against my body, especially formal gowns. at 10 was the second time, and it was her junior prom dress, silky panties and pushup bra. after that it went to nightgowns, corsets, and swimsuits.

[pantiwaistjamie]

I started with all my step-mother's things, and getting caught wearing her 1-pc swimsuit. and then My neighbor Shirly, I would sneak a couple pair of her full sized briefs, my step-mother found them in my room. then I started dating Sarahjustine, she had me wearing her lingerie, she weighed 400lbs, I loved it.. I live here in Alaska, where we do not have a LaneBryant or a Fashion Bug!! I miss shopping with my step-mother, we had so much fun!, call me 255-0797.

[AmberM]

My first articles of woman's clothing was my mom's white bra/panty set with a little black dress.

[StacyChambers]

First item was a frilly pink dress. Liked it so much I hid it, in a shoe box, behind the toilet so I could wear it whenever I felt like it. The next day mom found the box and confronted me. She wasn't happy about me hiding it but did say she would let me dress up if I wanted. Stupidly, I said no then ran back to my room!

She also caught me holding up one of her bra's to my chest. I've since learned how to be more discreet.

[Susan Thomas]

For me it was my Canadian aunts padded bra. I was actually held down by my cousins as they put the bra on me. I was only twelve years old and I was quite upset. It is funny though, when we got back home, I found myself trying on my sisters one-piece swimsuit. I then started wearing my sisters nylon panties. My mom caught me wearing my sister's swimsuit and started yelling at me and asking me if I wanted to be a girl. I guess she frightened me, because I didn't cross-dress again until I was out of college. I succumbed to my mother-in-law's pantyhose hanging in the bathroom. As I write this note, all is well and I am very comfortable wearing my pink bra and blue panties.

[Kimmie W]

It was a white brocade dress with matching heels and I was transported to heaven when I put it on and did my make up. I was probably 10 or 11 at the time. It was truly magical. I felt absolutely feminine and alive.

[Rachel Mari]

My sister's panties when I was around 4 or 5. Three of my sisters (ages 6, 8, 11) used to dress me up like I was a living doll for them, dress, panties, makeup, wig and shoes. Then they would parade me around and show everyone in the house and the nabors too. My other sisters (ages 20 & 22) didn't show much interest. Later (I know I was 5 at this time) I put on a pair of my mothers stockings.

[Donna June]

It was a slip, a nylon yellow full slip for a young girl (I was about 8). I tried it on and have been hooked ever since. I have a number of vintage slips now. A lot of my dresses and skirts don't need a slip but when they do, well lifting the hem of my dress / skirt and seeing the lace of a slip is just so feminine to me.

[DaphneATX]

I would assume that most of us tried our moms clothes on. Im not any different I would find her lingerie, heels, stockings, pretty much anything I could find... when I wanted sexier clothes I would raid friends sisters drawers for thongs and other things

[Briana90802]

The first thing I tried on was my sisters leggings and her pink leotard at age 7. We were playing dress up. I was parading around the house and my dad saw me and asked me to sit down. He told me that no matter what I do in life, as long as I don't hurt anyone, that I was his son and that he was proud of me no matter who I grew up to be. I didn't know what he was talking about at the time but of course now I do.

[Michelle_ct]

bikini...mmmm...felt so yummy. hehe

[Dannigirl]

My sister's friend had an awesome purple string bikini, I loved that bikini, in fact I loved my sister's friend as well but she was wayyyyy older than me back then (3 yrs.) :) I guess I would have been around 6 years old. Then my sister and I would change bathing suits in the pool as well, she only had a boring one piece, but it still felt great.

[Davina-Alba]

Mum's white satin bra. I'd have been about 13.
Mum, Dad and my brother had gone to town and I was alone and bored.
Tried it on from her underwear drawer. Only had it on for a minute when I paniced about them coming home finding me.
In the panic, I couldnt release to hooks and fumbled for a good 2 minutes before turning it around on me and un-doing it at the front.
5 minutes later, when I realised they'd be gone for hours, and had only been gone for 30 minutes, I was back in the drawer trying the matching knickers and the bra.
Then the matching suspenders too and some tan stockings.

So the very first was a bra, but in the same day I was up to full underwear.

The next saturday I went a lil further, more so the week after... and the rest leads me here :)

Jumping in at the deep end is often the best way :battingeyelashes:

[Starla]

One of my grandmother's full slips. I think I was about 7 or 8 at the time.

[Cari]

either pantyhose or a nightgown ; Ive tried to remember but just cant.

[Vikki Vixen]

High heels followed by stockings and suspenders.

[ziggie]

My mom's granny panties. Horrible as they were i liked it.

[Wantin_to_play]

My sister's panties when I was around 4 or 5. Three of my sisters (ages 6, 8, 11) used to dress me up like I was a living doll for them, dress, panties, makeup, wig and shoes. Then they would parade me around and show everyone in the house and the nabors too. My other sisters (ages 20 & 22) didn't show much interest. Later (I know I was 5 at this time) I put on a pair of my mothers stockings.

Do your sisters still help you?

[Cindygirl65]

For me it was my mothers navy colored leotard and a pair of her navy tights. I also donned her red wig. Oh I felt so sexy.

[bostonbecky]

One day when I was really young like 7 or 8 I remember jokingly asking my mom to try on her bra, and she thought it was hillarious

[sue1965]

A pair of my sister's black panties, then a bra, teddy and night gowns. i still remember the first time she caught me in her room dressed in her clothes.. :)

[Billie Jean]

For me it was my moms pantyhose when I was about 6.My mom's RHT stockings. She used to let me and my sister wear the ones with runs in them. Billie Jean

[lisagurl83]

was really young 4-5ish and i wore my cuzs tights and mary janes and went to play with her and her friends!!

[Stockingstopgirl]

OBG , stockings and bra, my mothers felt great.

[CaitlynRenee]

Panties and slip, age 4 or 5. Thanks, Grandma............., Thanks Mom......................., Thanks Sis and all of your friends too.

[rhonda]

I was 11 and tried on silky slip and dress , couldn't leave womens cloths alone ever since hooked and love it

[janetcd2]

For me it was my mother shoes she had so many beautiful pair I just love wearing them

[Rachel Lea]

High heels which were in my toy box when I was very small, but PANTYHOSE, when I was old enough to "know better".

[Rachel nylons]

My Mum's 15 denier tan tights, when I was about 8 years old.

[donnatracey]

Mom's dress...boy, was getting that zipper up tough in the back.......come to think of it, getting the zipper down w/o ripping anything wasn't easy either!

[laurajade]

My mom's pantyhose that I snuck out of her room. WAY too big for me at the age I was (which I can't even remember right now). Then one day my parents and I were walking through the mall parking lot and found a pair of Legg's Sheer Elegance in Size A. They were going to set them aside for my cousin, but I wound up sneaking around and wearing them whenever I could so much I put runners in them. My mom suspected what had happened and called me a sissy (of course, in a non-approving way).

[Janine cd]

My mom's slip and panties.

[WillowWriter]

My friend dressed me up in a bra, pink panties, a skirt and a tank top, then, styled my hair.

[Dfuzzy]

One of my mom's pantyhose. Loved them every since

[GingerLeigh]

Oh, pantyhose for sure. My mom had to hide them from me. First dress was my sister's ballerina tutu/tights costume. I may have been 5.

Ginger

[joanne51]

My mum's little black girdle (wore it in bed). Never realised at the time that it wouldn't end there!
It was long before the internet, so you felt cut off from anyone else who felt the same.

[SusanQ]

When I was 5 we had a foster child living with us who was an 8 year old girl. We always played together (my parents actually took in the foster child so that I'd have company, since I was an only child). One day we were playing in her room and she dared me to put on her panties and slip...I didn't think there was anything wrong with doing it, and had wondered how her clothes felt, since they were so different from what I wore (how come no opening in her underpants??? :))so I took the dare and put them on. We never told my parents that we did this...but from that time on I'd try to sneak some of my mother's things on me (vastly too big!! :)) and eventually I started going into my cousin's room who lived in the apartment upstairs of ours, and try on her bras, slips, panties, girdles and nylons.

[katesometimes]

For me it was my mother's wedding gown. I had never seen anything so fancy and when I found it I just had to put it on. I think I was 9 or 10 at the time and remember that even then it was too small for me to do all those buttons up in the back. Ever since, I've wanted my own wedding gown!

[SuzanneBender]

Like many of the women in this thread I started with my Mom's bra. I think I was 7 or 8 at the time. It was huge and I looked ridiculous. I had some girlfriends in the neighbor hood that had their dress up box. I would play with them and we would play dress up all the time. I had an outfit that I loved. It was a huge red hat, black dress, and white plastic pearls. I felt like the Queen Mum at high tea in that outfit.

[crystalbath]

For me it was a black thong,

tried and never stopped - felt way too good and natural

[meichenchan]

My sister was in ice skating. When her old ice skating dress was warn out, I snagged it and put that on along with an old pair of my mom's pantyhose. I think I was like 10 or 11 at the time.

[pantybear_oz]

My sister had a really nice one piece swimsuit that I tried on when I was about 10 or 11. It got me hooked. I still have swimsuits better than any other female clothing except maybe for a matching bra and panty set :-)

[christinac]

I don't really remember now what was the first article of womans clothing. I think it was a friend's sister's black bikini, but I honestly don't remember anymore.

[VioletJourney]

My mom's denim skirt and a black camisole. I tried desperately to put on some high heels, but she's got really small feet (size 7, I think)!

[longirl]

My Cousins Panties and after i tried one on i took all of hers

[Janine cd]

For me it was my mom's high heels. Actually, my first real experience at crossdresing was about 3 years latr when I tried on my mom's bra, panties and slip.

[Jennifer Soames]

my sisters pink and white panties

[LoriAnn_CD]

my sister's one piece clack bathing suit and then some of her dance leotards

[Julie Rose]

Panties!!! Panties!!! Panties!!!
Still love them 35 years later!!!

[Sarah V]

Mom's pantyhose and a chafe' panty of hers.

[becky9300]

All about the high heels and hose for me. Started with moms but the best were a friends sisters and ladies Id babysit/housesit for

[Jackinhose07]

Definately was all about hosiery for me, from a young age....Tights and pantyhose started my love for everything fem. And are still my favorite :).

[Makina]

The pantyhose of my mum when I was 4. They were drying and I was fascinated. My mother let me take them and play whith them

I remember wearing them over my clothes. They were so big for me that I almost managed to raise the waist of them above my face.

[Heather_Marie]

It was my girlfriends nice silky white bra with a pink little rose on the front 36B I still have it a wear it I love it.

[JainaCarpaccio]

that i remember, would by a pair of my sister's cotton panties, and one of her bras.

[Diane Meris]

It was my mom's panties and bras and stockings. I grew up and started dressing in pre-pantyhose days, or at least my mom didn't wear them. I progressed to dresses, nighties and all the other fun stuff pretty quickly.

[sexysarah20]

first thing for me was a pair of my sisters panties when i was 12

[jenna_woods]

for me my sisters panties, loved it that frist time,and wanted my own but that did not happen for a few years.

[Shanice]

If I remember correctly, it would be probably a dress, but I don't remember who's it was.

[CindyT]

Mom's pantyhose and girdle when I was like 6 or 7. Felt so good, like many others here, I never stopped! :-)

[missyvf]

my best friend's moms panties was the first thing I ever tried on

[Chrissy.Sexton]

Mom's silky half slip. Mmm, so lovely!

[Kalli]

For me it was one of my mom's panties and bra.

[dtride]

For me it was my mom`s high heels, then it turned into her pantyhose, it felt great

[Samanthascloset]

I would have to say a wig. there is a pic of me with one on when I was under a year old...I dont know who put it on me but if they only knew. I often wonder if that has anything to do with why I am the way I am....Thoughts?

[ToxicAvenger095]

Ah, I remember it was a little dress that was my sister's. Not sure how young I was...It must of been like during 2nd or 3rd grade! I just remember it was sitting on the couch, my mom left for a minute to take my dad to work, and I tried it on. I just remember how long I had been wanting to try girl's clothes on, and then I was hooked.

[Corrina]

For me it was a pair of spandex pants my sister had, then i quickly discovered pantyhose!

[tiffanyfisher]

I first wore a pair of green metallic panties that my ex had left. I can still feel the satin.

[hollydee]

My sister's red dress when no-one was home.

Holly

[crystal amber]

The first thing I wore was a pair of pink Leos split sole pointe shoes. I still dress like a ballerina and really wish I could take lessons.

[CandyH]

Mum's pantyhose, panties, dress, bra and heels. I was 7. Pantyhose are still my favourite!

[christina s]

My moms closest was overflowing at the town house we live at when i was younger .So she stored some of her clothes in my closest and the one thing that still stands out to me is a pink nighty .

[Marinamaze]

A pair of my mothers stockings and garter belt in 1969

[mooseboy77]

About seven years old and I tried on my mother's nightgown.

[stockinged nemo]

My Mom's pantyhose somewhere around the age of 8.

[Steph22]

For me it was my sisters panties when i was 13 i think.

[Natalie D]

Mums panties aged 12/13.

[girlygirly]

The first thing I tried on was mom's undies, and that was when I was eight.

[autumnrenee]

One of mom's bras around age 10 or so.

[Meredy]

My cousin dressed me up when we were very young, I remember she made me up to be her sister. I believe she had me wear everything.

[Marabelle]

My mothers slips at about age 4 or 5
Marabelle

[rhonda]

for me it was slip and satan dress from then on I could not stop very long any way

[KandisTX]

for me it was slip and satan dress from then on I could not stop very long any way

I wonder if this was a Freudian slip considering many feel that crossdressing is the work of the devil. ;)

[Shelley]

When I was 5 or 6 I found a box of girls clothes in the attic. I remember a pink dress, I think it was satin and lace. I concider to this day wearing that dress my first sexual experence.

[Phoebe P.]

My first time was masturbating in my Mom's pantyhose. Hopefully that's not overstepping my bounds and it doesn't sound too freaky!

[MaryAnn40c]

panties and bras....my mothers

[Randilegs]

My mom's pantyhose... and I was hooked from that moment on!

[joanna4]

My sisters colorful pink/green dress when I was around 3? She was crying and my mom told me to give it back while I was jumping on the sofa lol. Thats about all I remember.

[daywalker1966]

I esperimented with my mom's skirt and heels just to see how it felt, thenforgot about it. Years later I put on a vlevet dress and went to a party. It was fun as hell. I upgraded to a hoop skirt, and recently a bit more hot looking fishnets and corset. Someone mispronounced my name. Gene, and called me Ginnae years ago, so I kept that. I like to make Gene vanish as if he never existed and let Ginnae take over. It's a blast.

[brucelina]

i first wore my mums lingerie and clothes when i was 14 and now i have a good selection of womens lingerie and clothes and i also have a whole selection of womens one piecswimsuits that i wear when i have free time to wear them around the house

[kilted68]

I can vaguely remember being taken home from my aunts house wearing one of my cousin's dresses, when I was 4 or 5 and being "displayed to a neighbor lady". I don't know why my mom put the dress on me, but I think I liked it. Mom also dressed me as a girl for most Halloweens using my cousin's dresses.

[bridgette63]

The first thing i ever wore was a pair of panties and a silky nightgown,,, I was hooked after that.

[Adriennegrl]

Somewhere I have toddler pictures of me wearing my aunt's heels, so it started early for me. The earliest conscious memory is wearing my mom's pantyhose as an early teen.

[sallyissuper]

First panties then tried pantyhose. Loved mom's lipstick! Now it's shoes.

[Jamie-Lynn]

Pretty certain it was pantyhose when i was around 5-6.

[Shayla99]

Pantyhose.... tights.... a repressed child by religion exploring new desires (Sexuality), by a church that forbid desire....so I found stockings to be my sex, as a boy. Fantasizing of a girl wearing them, until that just became me wearing them??

[Nicola]

It was a green leotard and green footless tights back in the eighties. Having been scared out of my wits actually buying them, I couldn't wait to get home and try them on. I think it was during the reign of the "Green Godess" fitness woman. A pretty vile colour of green it was too but I was very pleased at the time.

[Cd.Nikki]

a green fun fur dress/skirt, i couldint resist, it was one of my sisters

[LoriAnn_CD]

first clothing was my sister's one piece, black bathing suit. It was hanging on the shower curtain rod to dry and I really wanted to know what it would feel like. I was young maybe 6 or 7. First outfit was my sisters also. I was lucky to be 2 years younger and about the same size. First outfit was always my fav - pink bikini panties and matching bra, tan pantyhose, a blue plaid skirt with a royal blue turtle neck sweater and about 1" heels. Add a little lipstick and I was in heaven. I "borrowed" many of my sisters clothes, hose and nighties over the years!
Love to all
LoriAnn

[texasm31]

Wow. I envy those of you that grew up with sisters. But then again, that might have been a good thing that i did not because I'm sure I would have been a bad little kid...and probably would have been caught numerous times.

[stonec657]

for me it was a pair of my sisters panties when i was 12 they were silky and felt so good i never gave them back shortly after that i liberated one of her bra's I was very lucky to have an older sister that was very fashionable.

[undergroundgirl]

My first experience was when I was 12. I went to my female friend's house and she made a dare for me to try on her clothes, I was hooked. I wish I would've had an understanding older sister, that would've made life easier than sneaking around and hiding in the dressing rooms at walmart.[/I]

[joanncd]

Put in a dress, had my hair styled, and sent to the shops.

[Darla]

Had to be a nice pair of red tights that were a hand me down in my moms "old" clothign drawer. A friend of mine's sister dared me to try on her old crocheted tights, and I did. Over my jeans! She was pissed I stretched them out. So the seed was planted and I had to try these tights on that were lying around my house. They were the most incredible shade of red, I remember - how can girls not totally freak when you can change your leg color with all these awesome tights? After that it was a slippery slope into sister's tights, leotards and tutus, and then into Mom's pantyhose. Eventually I tried her real silk stockings.

[Suzy Parker]

A late sixties short mini dress of moms that was royal blue with an empire waist and the top was a lighter baby blue with ruffles in the middle going around the neck with long sleeves and the same ruffle around the wrists. Pantyhose and everything else came a little later, I was only 6 at the time.

[Brandi layne]

My first article was my moms banana yellow 2 piece bathing suit I just loved the color of it and the way it felt and once I tried it on I loved the way it looked on me lol.I was around 13 at the time

[AmandaBlack]

Wife's thigh highs...shazam!!!

[ashleyfine]

The first thing i tried on was a bra and panties

[lynn_lynn]

I haven't yet posted here.

The first thing I truly wore all day was, a pair of white with black dots, lace band panties. with a tiny little bow in the middle. I wore them all day to 8th grade. Next time I wore a pair of black lace panties. They felt really nice under my Jordache jeans.

[amy817]

my first time was my cousins panties and later a different cousins bras, have been hooked ever since

[diannecourtney]

Well it started with men spandex briefs, loved them and wore them out with two or three years of consistant wearing. They were no longer available,what to do? Ah ha, the wife girdle, it was even better than the spandex and so much more sexy.

[Farrah Rose]

a pair of my mothers pantyhose, then the dress and heels weren't far behind that :p

[darla_g]

i think it was a bra, but it quickly progressed to a full outfit. my mom had a wig which i tried on along with these boots that had heels so i guess a full outfit is the correct answer. we should make this into a game show or something

[TeaganNataliaAcheson]

My mums bra and heels. Bra kinda just slipped right off, I was like 7 and the heels were obviously way too big.

[Kinky Keds]

A pair of womens white Keds canvas sneakers.
The first pair weren't my size, so I had to squeeze into them.

[MisterMark_1]

I first tried on my cousins swimming suite, then i moved on to wearing my sisters underwear. loved it! xx

[MargoM]

I am sure it was a half slip after I dried off after a shower, they were always in the the bathroom drying, but pantyhose was the 1st item I wore longer than a "Cheap Thrill Moment".

[suit]

nothing cheap about those moments that tranfix a mind to a life long quest!

[erica2]

I think the first thing I tried was panties, and then a bra. I went on to girdles after that, and actually had a couple of them stashed away for when I thought I could get away with wearing them under normal clothes. It felt REALLY risky, as where I grew up was a small place, and if you were found out, you would have been the laughing stock. They were a bunch of straightlaced people.

I never much did the pantyhose or hose at all. I used to hear my mom say how pantyhose were expensive, and were so easy to run. At the time, I think they were pretty new items, and I remember the garter belts and normal stockings for a lot longer. I didn't mess with them much either due to the run issues and the "expense."

So I stayed pretty much with stuff that wasn't easily messed up - or so I thought. The first time I wore the girdle out of the house, I ended up not being able to go and change pror to having to do some family chores. I had to mow two large yards with it on, and it was more than a little bit warm outside. It was a great feeling, but I was TERRIFIED of my parents noticing it under my clothes. I think I was about ten at the time.

As time went on, that one became my favorite article to wear. Turns out it didn't seem to be as noticeable as I may have thought.

I am Erica2

[Kaitlyn26]

I went with an entire outfit the first time. A friend made me over with her clothes and makeup in high school after she noticed we were the same size. Other than squeezing my foot into her shoes and having to buy my own undies it was great. So I kept doing it. :) And here I am!

[Ruthi]

my sisters bra panties garter belt and stockings she wanted to see me dressed.

[latnheat]

my mother still has a great figure at 50 but back then her legs were amazing..veary meatu and full.looked great in pantyhose and miniskirt.so it was vedy natural to me to try to emulate that look, so the first pieces I tried on where a tanned pair of pantyhose followed by a purple miniskirt it felt awesome

[SweetIonis]

I was initiated by way of a pair of sexy panties! White lace! Fireworks went off!!! It was love at first sight!!! LMAO!!!

[Jamie92]

My first piece of clothing was when I about 5 years old, when I went into my sisters closet and tired on her one piece swimsuit and also tried on one of her dresses I recall it was a blue one...
It felt accelerating!! =) Until I got caught! lol

[Jenny26]

i think i was in like 1st or 2nd grade and there were pantyhose drying on a rack in the bathroom... i locked myself in there and tried them on... several times... i loved how they felt...i remember there was a girl in like 2nd grade on the playground wearing tighs or pantyhose and i did everything in my power to try to touch her legs lol :-)

[Annaliese2010]

My sisters panties from the dirty clothes hamper worn over my head and situated just-so where the sweet part alligned with my mouth and nose - but that was for arrousal when after experiencing the real life 1st time random whiff of the amazing scent of a woman I quickly became addicted and wanted more and more... so it probly doesnt count :P

So I'd have to say my moms bra, filled with tons of tissue 'cause she was soo well endowed and sexy as all get out ;)

[Brown Eyed Girl]

It would have to be my Mom's slip when I was a pre-teen. Life was simple back then...she used to leave her slips and bras and girdles hanging in the bathroom. But it wasn't until I got older and started babysitting in my early teens that I really started.....while watching my young cousins it was my aunt's clothes once the little ones went to bed.....and then my best friends older sister's matching bra and panties....it was so nice to see something other than just white.....

[RachelX]

I would have to say rather than a first article of clothing I had a first ensemble of clothing.

One Saturday night when I was nine years old I gave in to temptation and decided to finally find out what it was like to dress as a girl. Luckily I had a well dressed sister two and a half years older than me. I went into my sisters room and got a little green skirt I had always liked. Taking it to my room, I removed all my boy clothes and pulled on the skirt.
I knew I would like it. I had been wanting to do this for years. But I could hardly believe how breathless I felt. I skipped down the stairs wanting to experience the feel of the skirt on my legs. I then sat down carefully smoothing out my skirt, finally performing this simple act I had forever wanted to imitate.
I was then overcome with the irresistible desire to dress completely. I knew that the next day I would have the house to myself for many hours. So I decided to put the skirt back and wait for tomorrow.
So the next day I grabbed the same skirt, and a matching green sweater from my sister's closet. I then went to my mother's room and got underwear. I had watched my mom put on pantyhose many times and always wondered what they would feel like to wear. I was now finally going to find out. As I pulled them up over my thighs and around my waist I remember enjoying it more than I had imagined was possible. The same thing occurred as I put on her padded bra and fastened the hooks in back. Luckily for me my mother wore fully padded bras which provided me with the perfect profile. Next was the skirt followed by the green cashmere sweater.

[Jennifer811]

My Mothers corset and slip It felt so great wish I had a corset now

[JillyNylonz]

I started with my Mother's Hanes RHT nylon stockings. I loved the sleek feel of them on my boy's legs and how smooth they made my legs look. I was delighted that her high heels fit my feet perfectly back then and enjoyed many fashion shows with her clothes when home "sick" from school..

[Suzy Parker]

I was probably one of the sickest kids in grade school, but not quite so sick I couldnt be left home alone while mom worked.

Cough cough sniff sniff I dont feel so good.

[Sam1985]

The very first pair of female clothes i tried on was a pair of nude pantyhose and i was 6 years old.

[Trina90]

Pantyhose, when I was really little. I loved it <3

[Mikka]

My mothers nylon stockings.

[demibra]

The first time for me was while playing doctor with a neighborhood girlfriend. She had laced nylon panties and a training bra that fit me so well that I asked her if she would give me some of her clothes to dress up in. My lifetime passion began at that moment.

[kassy]

Wow the first article woul dbe my sisters bra and panties and quickly progressed to her skirts and tops. I always dug in the hamper for those bra and panties first. the natural scent of a woman was even more for effect when I was arround 12 or 13.

[Angel Wesch]

The first thing i wore was a pair of size five white cotton Hane her way panties. They were so comfortable they helped me decided to wear panties 24/7

[AKADonna]

For me, it was also Mom's bra! I used tennis balls for breastforms, put on a tight T shirt and thought how great I looked. LOL

[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.

[sarah kay]

My moms bra, probably when I was 10 or 11. She had padded bra's. I remember it felt great, no - amazing!

[heel_addict]

A pair of my mother's pantyhose with some runs that she had just gotten rid of, when I was about 8. I don't I'll ever quit wearing pantyhose, even secretly under my pants.

[Danielle_cder]

my aunts panty hose, and bra.

[wish4naught]

I was 15 and my gf at the time somehow managed to get me 1/2 into one of her bras when we were playing around in her room. First time I actually wore something was later that year @ halloween. A bunch of us did a gender-swap thing, I wore a black tank and a pink skirt.

[cdtraveler]

My Mom's girdle and slip then bra. loved the smell and soft yet tight feel. haven't looked back since.

[caroline2k]

My first posting so what better than to tell of my first dressing experience?

I was about 6 or 7 and was playing in the lounge after a bath and for some reason put on a pair of my mother's sheer tights (pantyhose). I can still remember tthe thrill! I then put on another pair over the first and proceeded to prance around like a ballet dancer in an attempt to justify wearing them. My mother was fine about it and I sat in those tighhts for the rest of the evening till bed time, when I had to take them off... :(

Soon after that I was sneaking the occaisional pair of tights and then panties and girdles and slips until I hit my teenage years when it all spiralled and I had to have my own stuff. Unfortunately, when my stash was subsequently found, it was not as welcome as my initial 'playtime' dress-up...

[KellyJameson]

Only child with a mother who was a real estate broker and father who was a pilot I had no shortage of alone time or privacy and started at eight with her wigs and makeup. looking in the mirror for the first time with the wig on was the first time I felt my reflection match my sense of self and the mold was set. By thirteen I was the same size as my mother who favored Ann Taylor, still one of my favorites for shopping. She had closets full of clothes and never noticed.

[Birgitta]

My mom's pantyhose....I was 13 then!

[lindseycdg]

Sisters bathing suit. It was white with a strapless top and had a wood ring in the center of the top. Very Sexy! :)

[Vanessa Winters]

The first piece of female attire I wore was my moms green floral dress, which I now find interesting since most of you who have posted started out with some form of underwear.

[Susan_Xdress]

My mother's full slip. White with white lace trim on the hem and bodice

[steftoday]

I had it good with my mom's stuff; she worked in the lingerie department of a large department store. She had all kinds of wonderful full slips, half slips, girdles and stockings. Mine was one of her full slips under one of her dresses.
I wish I still had the lingerie she had over the years. I would be the proprietor of a nice little vintage lingerie shop on eBay!

[DivaB]

Nylons and I felt something right away

[candykowal]

When I was 13, already had breasts so it was natural to try on my moms fredricks of hollywood bras she put up in the closet next to my bedroom when she got too big to wear them.
The feeling of being contoured was an instant hook for me!

[Jacy]

Pantyhose and skirt at 13. It was the best feeling ever.

[Imeni]

Hmm. I don't really recall the age. And it's hard because I've been doing it since I was very, very young. Even as a small kid in kindergarden, I'd go into my mom's bedroom and wear one of her dresses. I was eventually caught but didn't stop. Throughout the years, its gone from my mom to my sister's dresses and things, to my friend's parents to eventually my step mom's wardrobe until I moved out on my own. I ignored that part of me for years, as I had many roommates who don't share my open mindedness about things until one day, I was shopping for something or other on some sight, came across a silk chemise and ordered that, some panties and a bra. My grandmother, bless her heart, let me use her credit card and only asked once what i needed them for. I gave some silly excuse that I know she didn't buy but a few months after, died of cancer. I like think she knew why. So, I mean, as a kid, my very first time? I think it was my mom's white silk dress. But as an actually crossdresser, something special that was given to me by the first woman who knew and accepted me. =3

[JaniceP]

The very first item I tried on, was a lacy half slip of my mothers. (I was about 5).

The very first item I bought, was a Pink Garter Panty, followed by stockings. (I was 10). They Felt Wonderful!

[natalie james]

my sisters mini skirts when i was little,things in my hair, whatever makeup i could pilfer, and my sisters heels

[GBJoker]

Several thousand years ago, and (very literally) in another life... In other words, when I was about 7ish... I think; I tried putting on my sister's make up. Sister made fun of me, parents thought I was weird, so I ignored it. Then, about only a few hundred years ago (and still in that previous life), home alone after school, couldn't resist trying on my sister's skirt and matching... Uh.. .Blouse? thingy... that went with it.

[Stockingstopgirl]

Got to be OBG with Tan stockings my mothers and white bra

[Darlene92]

a full on japanese school girl outfit my girlfriend at the time bought me for halloween

[bellini]

My sisters makeup! and a silk scarf. Oh my god - seems like 100 years ago!

[Dixie]

When I was young (about 4 or 5) I had a baby sitter that would dress me as a little girl then we played house. The first thing I tried on my own wad my moms panties and bra when I was about 9 or 10

[Gangsta_Gus]

the first thing that I wore was one of my moms sports bras unmolded and several camis. I wish that I kept some of them.

[kundthu1]

I was dressed as a girl upto the age of 5. On my own, i strated with wife's panties and camisole

[BrendaT]

My Aunt's panties and bra. So HOT

[Julie1123]

If I remember right it was a pair of my mom's panties when I was a teen.