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What item of clothing got you into cross dressing?

117 Posts
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Posts: 185
Duchess
Topic starter
(@joannat)
Reputable Member     Gwynedd, United Kingdom
Joined: 4 months ago

As a child, I tried on my mother’s tights (pantyhose), but what I think really did it for me, was Dr Scholl’s exercise sandals.  I was a boy in 1970s England, and every trendy girl or woman seemed to have a pair of these wooden soled sandals , including an aunt and my slightly older cousin Susan.

As a nine year-old, I was fascinated by Sue’s Scholls. How on earth could she walk around on two bits of wood? The navy blue straps with their gold fastener looked smart, and the soles made a great clip-clopping noise whilst she walked. Our feet were the same size, and one summer’s day, she let me wear her Scholls for an afternoon together, in exchange for my own flip flops, and I was hooked! I couldn’t believe how comfortable the wooden soles were, and I loved how they looked on my feet.

Sadly, my mother wouldn’t let me have a pair of Scholls of my own, as these were ‘girls’ sandals’, so I just had to carry on with being given a a new pair of flip flops each May. 🤷‍♀️ Sue would always let me wear her Scholls after that first time though, and when she got a new pair, the old ones were put aside for me to wear whenever Mum and I went over there, until I outgrew them.

 Needless to say, as Joanna I am now regularly clip-clopping about in Scholls during the summer months, as they’re great for showing off my pedicure, and have a second pair as my house slippers!

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116 Replies
31 Replies
(@brittney2016)
Joined: 6 years ago

Prominent Member     Cincinnati, Ohio, United States of America
Posts: 907

@joannat; It was three pairs of nylon panties that I found in my Grand Aunt's spare bedroom dresser drawer. I asked her if I could try them on and she said I could. I was 8 years old; later on she allowed me access to all of her panties, slips, and dresses. At the time I considered it playing "dressing-up", not crossdressing.

The experience stayed with me into my adult years; when at 43, I bought my first panty that started my feminine clothes collection.

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(@briefgirl)
Joined: 2 years ago

Active Member     Palm Springs, California, United States of America
Posts: 5

@brittney2016 I also had an aunt that always had freshly laundered panties in her bathroom. She’d catch me trying on her panties and never cared. She’d let me wear them until mom came to pick me up.

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Lady
(@stephanieann)
Joined: 2 months ago

Prominent Member     Northern California, California, United States of America
Posts: 531

@brittney2016 

Lov your wonderful story,  I would have lov to know your Grand Aunt ,  and had the wonderful loving experience. 

 

Huggs 

Stephanie👠 

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Lady
(@jessicaskye231)
Joined: 11 months ago

Eminent Member     Michigan, United States of America
Posts: 15

@joannat for me it was the first time stepping foot into heels.  Not sure why, but the feeling was sooo good and felt so right.  That is when I knew I wanted to fully dress and there was no going back. 🙂

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Duchess
(@jennconn)
Joined: 2 years ago

Noble Member     Florida, United States of America
Posts: 768

@joannat it was my fascination with stockings.  They didn’t have panty hose when I first thought about crossdressing, so every proper lady that wore stockings had a girdle or garter belt to go with those pretty stockings.  I still love wearing all of these items, but the thought of those is what got me started.

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Duchess
(@aliceblack)
Joined: 5 years ago

Honorable Member     Massachusetts, United States of America
Posts: 431
Duchess
(@aliceblack)
Joined: 5 years ago

Honorable Member     Massachusetts, United States of America
Posts: 431

@jennconn I am with you. I found a girdle, garters and stockings to be enticing and sexy. Thus, I have purchased that grouping.

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Duchess
(@rebeccaoh)
Joined: 7 months ago

Estimable Member     Oxford, Ohio, United States of America
Posts: 77

@joannat My first memories of crossdressing I was I think 7 at the time. I would sneak into my mom’s room to just go through everything imaginable. My favorites were heels and panties for sure. Back then I was lucky enough to have feet small enough to ply around until I was a teenager. Puberty hit and my fun came to an end lol. I still remember the way I would just prance as if I had any idea how to walk in a heel then haha. Still seem to be drawn to those items more than others, but my dress collection has taken over the closet these days 🙂

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Lady
(@wendye47)
Joined: 9 months ago

Estimable Member     Clwyd, United Kingdom
Posts: 79

@joannat It was my Mum’s stockings and girdles. I loved the wonderful feeling of the garments on my skin. Soon followed by her high heeled shoes, petticoats and all in one swimming costume. Great days.

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(@geniv_cd)
Joined: 8 years ago

Reputable Member     Minneapolis, Minnesota, United States of America
Posts: 269

@joannat For me it was my Mom’s red lipstick. 🥰

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(@charlenecd62)
Joined: 2 years ago

Trusted Member     North Carolina, United States of America
Posts: 20

@joannat for me it was pantyhose. I was helping put away the laundry and marveled how they felt. Later I had to sneak in and something called to me to try them on. I’ve been hooked ever since.

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Lady
(@briana)
Joined: 2 years ago

Estimable Member     Florida, United States of America
Posts: 67

@joannat Hi Joanna,  i first tried in mom's bra and panties, followed by panty hose and a slip. i was a kid at home, about 10or11 years old.   i was inspired by the ads for Frederick's of Hollywood in mom's Cosmo mags in the mid-1970s.

 

 

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(@Anonymous 100045)
Joined: 2 months ago

Eminent Member
Posts: 28

@briana I remember those ads! They also had ads for high heels in larger sizes for men.  I wish I could remember the brand, but I remember being fascinated by the concept.

Cosmo was the best!

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Baroness
(@chrisfp99)
Joined: 2 years ago

Famed Member     London , Kent, United Kingdom
Posts: 1733

@joannat Look girls, you know my story but as it's rather unconventional I'll repeat it briefly. I had no inkling as a youngster. No desire to try any of my mother's things. Then in my early twenties I suddenly experienced an overwhelming desire to put on some lipstick. I can remember that moment as if it were yesterday. Sort of ballooned from there but won't go over it all again now xx.

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(@dovemtn2016)
Joined: 1 year ago

Honorable Member     Tucson, Arizona, United States of America
Posts: 313

@joannat What a great question! I did wear my mother's things with her permission. Amazing! 

The first item that REALLY got to me was heels. I was in my mid-thirties and I was walking home with my girlfriend and I saw a pair of black patent leather heels in a store window. For some reason I had to have them! The next day I bought them for her. 

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Ambassador
(@alexina)
Joined: 1 year ago

Illustrious Member     Fife, United Kingdom
Posts: 2212

@joannat 

It was a pair of my mum's real nylons, it would be early to mid sixties, before tights became universal.

I was just curious to see how different they would feel compared to my socks. That clearly opened the door to recognising my female side and so began well over fifty years of furtive dressing, being consumed with guilt and shame and believing that I was not as good as the other guys that I hung about with.

That short paragraph doesn't even come close to describing how I've felt for most of my life but not anymore 😊.

I still love and occasionally wear real nylons, there's nothing like them!

Great topic, Joanna.

Allie x

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Lady
(@sunnyday)
Joined: 2 years ago

Estimable Member     Oxford, Oxfordshire, United Kingdom
Posts: 140

@joannat - I'm not sure. It's difficult to place cause and effect. I remember hiding my mother's bras under my pillow - I might have liked the smell of her. I remember my mother dressing me in my sister's skirt while outdoors because I got my shorts wet in a paddling pool - I went home with her on the bus like that. I remember the 16 or 17 year old sister of a friend of mine rubbing against me (innocently) in her short dress and tights. I remember being hugely aroused by a girl in our street who wore very short skirts and long, over the knee, leather boots. With that array of experiences, it's difficult to say!

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Lady
(@sunnyday)
Joined: 2 years ago

Estimable Member     Oxford, Oxfordshire, United Kingdom
Posts: 140

I blame Dame Joan Collins as well. Especially her appearances in 'The Bitch' and 'The Stud'. My goodness - that lip gloss, that eye makeup, that beautifully coiffed hair (wig), that lingerie. I so wanted to look just like her. 😊 

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(@davinaes)
Joined: 2 years ago

Estimable Member     El Segundo, California, United States of America
Posts: 73

@joannat 

For me, it was my mother's lite blue leotard and white leggings. I was a young teenager in the 80's and aerobics was at its peak.  She would hang the leotard and leggings to dry on the bathroom door I used. If they were hanging there when I got ready for bed, I would try them on and admire how I looked in the mirror.  

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(@denimwear)
Joined: 4 years ago

    Other, Alberta, Canada
Posts: 697

@joannat 

For me it was my sister's dress when I was eleven years old. 

Lynne 

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Duchess
(@aliceblack)
Joined: 5 years ago

Honorable Member     Massachusetts, United States of America
Posts: 431

@denimwear I am with you. I wore my sisters things as well as my mothers.

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(@cdashley)
Joined: 5 years ago

Noble Member     Oshawa, Ontario, Canada
Posts: 1489

@joannat Those pantyhose hanging over the shower curtain rod drying. Yes it was either my moms or sisters pantyhose that sparked the flame for me , soon after a girdle and slip.

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(@jennyphose)
Joined: 3 years ago

Estimable Member     West Midlands, United Kingdom
Posts: 96

@joannat 

Hi Joanna - this is a great question, and it looks like there is often a bit of a common theme here, with either mothers, sisters or a relatives clothing just tempting us to try them on....  I wonder why there was just such a pull for us - and often at an impressionable age?  I suppose there is a lot of psychology around it, I won't pretend I understand it though - many here might.

For me it was my mothers suntan coloured tights (pantyhose if you are in the US).  I was probably around 10 years old - they were drying over our bath - I think she'd recently hand washed them and draped them over the bath to dry off.... they were just a bit damp still, but nevertheless, I just had a strong desire to try them on - so I did.  They felt amazing, though I knew it was wrong for me to be trying them on, as they were for ladies - but this was the start of things for me.  

In previous times I remember being fascinated as a child by the hosiery department in our local town, that had mannequins (bottom half, hips and legs only) displaying an array of different colours and designs of tights - so I guess that may have been in my subconscious that I needed to try them on? 

So from then on, I would occasionally try a pair on when I got the chance, and I noticed it aroused me greatly - and it continued to do so for many years - I started to buy the odd pair as I got older, and hid them from sight.  Again, I knew deep down that this was wrong, and that they were for women, so I convinced myself I was just weird, and this was like a kind of fetish and I told no-one about it.... I didn't really know what "cross dressing" meant, until much later.

My love of tights grew, and led me to want to try them with shoes - I bought several pairs of heels to wear with them in private, and that was enough for many years.

More recently, as I approached my 50's, I felt the urge to try more clothes - the tights and heels thing was still there, but I just wanted to try more things.  It was at bit of a tough time in my life, and I think back now that it may have been a bit of a coping mechanism, a distraction from what was going on.  So I ended up buying some clothes, and that was really the time that Jenny came to be.... over time I bought a few more clothes, makeup, wigs, more shoes and so on.... I feel I'm still in my early stages of cross dressing and still building my alternative wardrobe, and I know I have so much more to learn (especially about make up and co-ordinating clothes properly) - but I have been out at Jenny as many times which is a great thrill - it all goes back to that first time trying on tights when I was 10 years old.....who would have thought eh?

I guess many here can relate a similar story - I now know I am not alone, which is a great comfort.

Jen x 

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(@stephaniegirl226)
Joined: 8 years ago

Estimable Member     Wisconsin, United States of America
Posts: 104

@joannat My Mother had a red slip with lace. I loved it! Vert feminine

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Baroness
(@samarawilson)
Joined: 2 months ago

Estimable Member     Buffalo, New York, United States of America
Posts: 55

@joannat Mini skirt, stockings and panties. Still my favorites to this day. 😉

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Duchess
(@gemmalovegood)
Joined: 2 years ago

Estimable Member     Lexington, Kentucky, United States of America
Posts: 75

@joannat Bathing suits were my gateway, which soon gave way to panties and bras (naturally).

I found some of my sister’s old bathing suits in the attic, and would wear them whenever I was alone. The slick and shiny fabric, and tight fit just felt glorious, and natural.

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Duchess
(@elguapo)
Joined: 9 years ago

Reputable Member     The Villages, Florida, United States of America
Posts: 314

@joannat mother's square dance dresses.

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(@Anonymous 100045)
Joined: 2 months ago

Eminent Member
Posts: 28

@joannat My mom had a pair of caramel colored knee-high (on her) boots that I remember being obsessed with when I was maybe 5 or 6 years old. I would sit on the floor of a bedroom closet (oh, the irony) and slide those boots on every chance I got. I didn't understand the feelings I would get by wearing them, but I knew for sure that I liked it!

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Baroness
(@chloec)
Joined: 5 years ago

Prominent Member     Lakeshore, Michigan, United States of America
Posts: 864

@joannat Probably shapewear, but what I remember most that I was in love with was a 'party dress' - from the 50's of course - that my mother had (probably 1961/2). Tight bodice, full skirt, medium short sleave, collar, brown and white sort of polka dot (iirc!!!). That's what I imagined myself to look like if only........<sigh>

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Duchess
(@loneleycd)
Joined: 5 years ago

Famed Member     Roland, Iowa, United States of America
Posts: 2157

@joannat For me it was a pair of my mother's old pantihose which I pulled onto my legs in front of everyone in our living room when I was about 6 or 7.

 

Cassie 

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Lady
(@astridt)
Joined: 2 months ago

Estimable Member     London, United Kingdom
Posts: 102

@joannat it really was a scarf that some lady had left in public transport when I was a kid, the smooth fabric felt amazing and it had a wonderful feminine scent. I was hooked from that moment on!

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Posts: 2172
 J J
Lady
(@jjandme)
Famed Member     California, United States of America
Joined: 5 years ago

I would have to say it was my soon to be wife's panties. I wore them on day when she was out of town and loved wearing them, and told her so that nigjr when we takled on the phone.

I qualify that because I did dress a couple times as a kid on a whim. I just wondered what it was like so dressed fully in my mom's things. Stockings, girdle with garters, bra dress wig and shoes. Wvwrything but make up. At the time I had no burning desire to dress and had not been sneaking chances, I just decide one day to try it all on and it was fun and wonderful, but almost a one off thing, (I vaguely remember dressing one other time.) I did not even think about it for many, many years until I put on the panties. 

Once I wore her panties, I was hooked, but it was a rare occurance that slowly grew and then syaryed to include wear her bra during sex. She was fine with it, and we both enjoyed it so it slowly began to occur more ogten and eventually led me to fully dress, always with her full knowledge.

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Posts: 1209
(@lauren114)
Noble Member     Delaware, United States of America
Joined: 2 years ago

For me it was stockings followed closely by high heels.   It was pale colored stockings that first caught my eye especially this one pair that has a built-in lace panty top.  I have always loved black panty hose too.

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Posts: 4023
Lady
(@harriette)
Illustrious Member     Toronto, Ontario, Canada
Joined: 2 years ago

My recollection is that a pair of what I call harem pants caught my eye, on a mannequin in front of a nurse's scrubs supply store.

Thin, in a medium blue, and obviously loose and desiged for women. Perfect for lounging around, but I also wore them abroad, probably much to the embarrassment of my wife. 

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Posts: 485
Lady
(@cherylt)
Prominent Member     Honesdale, Pennsylvania, United States of America
Joined: 7 months ago

My first item was a pair of mom's nylon panties. They were so different from what I wore and my curiosity got the best of me. From the first day I wore them I knew I wanted much more. They just felt so natural to me even at age 5. After that it was a bra. That did it and from then on I just knew there was a girl inside. After that I just had to try everything.

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Posts: 98
(@judevderl)
Estimable Member     London, United Kingdom
Joined: 2 months ago

Great topic, Joanna!

It was a pair of my sister's knickers which I saw in the drying / laundry room a matter of days after I turned 15. I just looked at them and thought I've got to try them on. A switch must have been flicked in my head when I turned 15 as I'd seen her underwear lying around many a time but never even thought about wearing it until then.

Things quickly progressed to bras, tights and then on to one of her skirt suits and heels that she bought for her first job closely followed by other items of her clothing. My timing was good as despite her being a few years older, we were both small in size so her clothes were a good fit. Then I had a bit of a growth spurt which made things, well, a bit tight and uncomfortable really.

The rest is history, I guess.

 

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Posts: 812
 Leah
Baroness
(@leah63)
Noble Member     Minneapolis, Minnesota, United States of America
Joined: 7 years ago

It was my sisters pair of pink satin panties when I was about 4 yrs old, from there it went to bras and stockings and garter belts and baby dolls ..it continued from there to where I am today

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1 Reply
(@briefgirl)
Joined: 2 years ago

Active Member     Palm Springs, California, United States of America
Posts: 5

@leah63  I remember at around 4 or 5 mom putting me in my sister’s nylon panties for some reason. I remember how silky they felt and how exciting it was to wear them. I was hooked on panties from that point.

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Posts: 13
(@dstephans)
Eminent Member     SF, California, United States of America
Joined: 2 years ago

Little Dotty always admired nylon covered legs. So one day when my parents were away Dotty had enough and had to try them for herself. She went into my mother’s dresser and put on a pair of my mothers sears hug along nylon’s. Dotty’s feet and legs were way too small for them to fit properly and then she got caught wearing them by the baby sitter. So that’s what planted the seed and shortly after that it grew into regularly wearing my sister’s tights. There were certain types of tights that were smooth like the nylons not the same but at least they fit well. Then it happened the day my sister got her first pair of pantyhose. Dotty couldn’t wait to get her hands on them and her legs into them. When that finally happened I was in 3rd grade in school. That was the magical moment when it happened the first time finally getting to wear pantyhose. It felt so wonderful that Dotty had to instantly  put on a matching skirt and blouse set that belonged to my sister. And the rest is history. So it was most certainly the pantyhose that triggered a life time of dressing.

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Posts: 142
(@katiep)
Reputable Member     Nottinghamshire, United Kingdom
Joined: 3 months ago

For me it was white girdle with 6 suspender straps and stockings. 

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Posts: 124
(@kpl58)
Estimable Member     Virginia, United States of America
Joined: 4 years ago

The item that got me started was my mom’s bra that I discovered in the laundry hamper when I was 11 or 12. From the moment I put it on I was hooked.  I would regularly check the hamper and wear the bras I found there.  Unfortunately, she caught me one day, which was very embarrassing, but she didn’t make a big deal out of it as I suspect she knew what I had been doing all along.  Despite my embarrassment, it didn’t stop me from wearing her bras, which later also included wearing bras I found in her dresser and storage trunk.  Ever since then, bras have always been my favorite item to wear.

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Posts: 3446
Hostess
(@ab123)
Illustrious Member     Surrey, United Kingdom
Joined: 5 years ago

Mine was dresses when I was four or five. My sisters were wearing colourful ones and I felt deprived wearing drab. Any chance to wear one was taken and then things developed from there when I realised dresses weren't the only things nor a phase - they were for life.

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4 Replies
(@Anonymous 100045)
Joined: 2 months ago

Eminent Member
Posts: 28

@ab123 is that what you all call masculine clothes "drab" I've just joined CDH but I've been thinking of masculine clothes as ugly.

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 4023

@jasmine1866 Same thing. 😁

I think most of us here would consider drab clothes to be ugly.

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(@Anonymous 100045)
Joined: 2 months ago

Eminent Member
Posts: 28

@harriette LOL I guess so, stupid comment.

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(@brittney2016)
Joined: 6 years ago

Prominent Member     Cincinnati, Ohio, United States of America
Posts: 907

@jasmine1866; Welcome to CDH, Jasmine.

In most circles of society; "drab" means: unassuming or boring; ugly.

In the circle of the crossdressing world; "drab" means: "dressed as a boy".

So for us crossdressers; masculine clothes are also drab: unassuming, boring, and ugly.

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Posts: 310
Lady
(@brandicd11)
Reputable Member     New York, United States of America
Joined: 1 year ago

Hi Joanna,

For Brand it was aprons, specifically H-back ruffled aprons.  Recall seeing them in TV commericals and at both my grandmother's houses. Snuck into rooms to wear them and have never looked back 

My mom's girdles came next and the in-between articles of clothing came in place to be worn.

Hugs,

Brandi

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Posts: 140
(@gisellereeves)
Estimable Member     Oshawa, Ontario, Canada
Joined: 3 years ago

my mom's open bottom girdle and gartered nylons

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Posts: 28
(@Anonymous 100045)
Eminent Member
Joined: 2 months ago

For me it was some of my mum's stockings she'd left hanging about. Sounds a bit weird wearing your mother's stockings but when I put them on.... She's gone now but I think she would have been horrified if she knew. I used to tell her I liked this skirt/dress etc but she would always push it down with a "don't be silly"

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Posts: 210
Lady
(@lillie)
Reputable Member     South Carolina, United States of America
Joined: 4 years ago

My sister would do my hair and put me into a tight top with a can can, which I loved to wear.  Have to remember this was in the fifties. Years later, it was hair and makeup and that lead into trying on my wife's clothes. 

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