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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!
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.
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.
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.
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.
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.
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
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.
For me it was white girdle with 6 suspender straps and stockings.
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.
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.
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
my mom's open bottom girdle and gartered nylons
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"
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.