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For me, I was about nine or ten. My mother had left a pile of the weekend's completed washing on my bedside chair, for me to put away. In the middle were a pair of my sister's black, cotton, bikini-brief, panties (Knickers). They were so soft, I couldn't help but try them on. They felt so much nicer than my boy's underwear. I was hooked. A few months later I was packing some unwanted boxes into our attic. Rearranging stuff to make it fit, I found a box of my mother's old clothes, including a pretty, suspender belt and stockings. I was sure she hadn't worn them since she had us children. I filched them and wore them, whenever I was alone in the house. I "borrowed" some of my sister's stuff occasionally over the years, then snuck them back into the washing hamper. I tried not too. Then I got old enough and brave enough to buy my own. So, here I am, fifty years later, still wearing pretty and soft lingerie, pretty much full time, and skirts and blouses when I can.
Hi All,
My gateway drug was trying on mom’s strappy heels at 11 years old. The rest of the items started coming together by going to college. Well, why not try panty hose with the heels? Why not panties and bra? Hmm, how about a blouse, skirt, dress? Oh I need a wig too! And make up! And so on…
XOXO
Karensa
For me it was being a very young boy seeing the other girls at my school wearing skirts and dresses. I wanted to wear them too. I would usually stretch out the neck of a t shirt and tie the sleeves together so it looked skirt. Another thing i would do it cut a pillowcase on one side and wear that too. It was until years later that I actually tried on a real skirt and dress. The feeling was euphoric.
My moms Leather boots and cute little flag bra.....I must have fond the old days stash spot!!
For me it all started when I was home alone and decided to sneak into my sisters room and I saw a red sports bra which I tried on and felt so happy and alive instantly 🙂!! Later I tried on her cotton panties and they were so soft and comfortable! I didn’t start wearing skirts and dresses 👗 until years later but I was wearing lingerie every day under my male clothing and still do today
High heels. I can still remember to this day the sound when I wore my mother's heels for the first time. It is a distinctive sound, and I still enjoy that sound every time I wear my heels.
I have always enjoyed wearing tight's (pantihose) mostly against my skin with other underwear over the top, but as a young teen i really wanted a girls gym kit with the pleated wrap over skirt, polo top, gym knicks and long school sock's, these still hold a facination for me and to be able to still wear the kit and class unifom.
My Mom was a nurse , and back in the day a nurse wore a uniform and I have 2 older sisters and back in the day wearing pantyhose or stockings was much more popular. So between the 3 of them, it was almost gaurenteed that every other day there would be my Moms white or tan colored pantyhose hangin on the shower rod in our bathroom along with my sisters. I loved borrowing them and can clearly remeber the first time i slide a a pair up my legs...... OMG!! To this day, pantyhose and stockings are my favorite piece of lingerie. im not dressed unless im wearing one or the other.
It was stockings for me, black and snaffled from my mother's lingerie drawer when I was home alone. I was hooked of course from the moment I slid my toes into into the nylon. I'm struck by how quickly I progressed from there, it was a wonderful feeling but incomplete. So lingerie, led to skirts and dresses and from there it was a short skip to make up.
I'll never forget slipping into that first stocking though. I can recall it so vividly.
My wife had a nightgown that I tried on her as kind of a joke. After the laugh she asked if i liked it. I said no...I lied. I liked it a lot!
After that I had a few skirmishes with her stockings that ultimately proved to be my gateway drug.
When I was a young'un my parents would go out to dinner and my mother had this purple velvet dress with a metallic gold belt that was so soft and lovely that I was always transfixed by it. For some time I resisted the urge to try it on out of respect for my mother. I had some velour sweaters that I would wear as skirts that I would secretly wear in my room. Of course my mother would start wondering why the collars of those sweaters got so stretched out. Eventually I would risk trying on the dress, which sometimes led me to getting caught and punished. But it's many decades later and I now have my own velvet dresses to enjoy, and that's all that matters to me.
It wasn’t technically an item of clothing, but it was toenail polish and toe rings for me. I’d been wearing panties for a while, but that only sort of opened the door a crack. But immediately after my first pedicure/polish, I went to a coffee shop that had outdoor seating, and sat in a sunny spot. I looked down at my feet— rings and polish glistening in the sun, and thought, “Wow. I have pretty feet” It was the first time I ever felt girly. That got the ball rolling.
In my case I would say it was actually the Sears catalog... It piqued my interest and gave me the idea to search through my mother's things
My mothers swim suit. While seeing it hang over the shower curtain to dry. I was just drawn to it and had to know how it felt to put it on. I was hooked on the sensation of a smooth front and the look of having breasts.
When I was 11, I saw girls at school starting to wear bras and I got curious. At home I secretly tried on my sister's bra!
I still love bras to this day, I'm even wearing one right now!
