Whose lingerie have you tried for the first time?

We all would have started started crossdressing somewhere. I was just curious on knowing Whose lingerie have you tried for the first time?

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  • Mom/Step Mom
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    • #406530
      Jenny Thigh High
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      Sister’s while I was a young teen.  Maybe 12 or 13? Not sure.

      Primarily pantyhose 🙂

      She did not know  😉

      Used to read her Cosmo mags too, trying to pick up tips on how to be sexier 😉

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    • #406529
      Stephani Lovelace
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      I’m pretty sure that in my teen years, when I was first learning about Stephani, there weren’t many women in my life that I hadn’t tried on their clothes! I was a regular “panty bandit” lol. I knew from the first Vanity Fair panties of my Grandmothers that I was hooked! My favorite was when I would be wearing the panties of who I was talking to, what a rush!

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    • #405204
      Jin Crocker
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      My  sister loved to put me into her nighties when we were young. Actually, she still does whenever she comes to visit!

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    • #405109
      Rachel Lace
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      I started wearing my mom’s lingerie and panties round age 12. Once I started I couldn’t stop, I would love when I had the house to myself and I could dress in a full teddy with garters and stockings. She had so many panties and sexy lingerie. I’d be able to take a couple pairs for good and hide them in my room in case I couldn’t get a pair from her room.

    • #404029
      Sonia Pink
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      Same as most it seems !! My mums lingerie was my first step , I just couldn’t get enough .whenever I thought I had the house to myself I’d run upstairs and find what I could

      sonia xxx

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    • #403576
      Brenda Stevens
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      As a young boy I recognized that my mom and girls didn’t wear what I had to wear but I so loved pretty girly things and wanted to wear what girls wore. Anyways, being a boy and told girls things were for girls and boys were for boys I resisted the temptation to try on girly things until I was 11 and there was a lovely silky pair of mom’s panties on the clotheshorse and…well…my crossdressing began and I have so enjoyed my girly fem side ever since. From that day on I was constantly looking and feeling into the clothes hamper and mom’s panty drawer and I’m sure she knew but we never chatted about it. I also sneaked into my mom’s sisters panty and slip drawers too years later…my auntie had the most lovely silky slips and panties and the prettiest nighties…I just could not help myself!!! As my crossdressing years passed on I got up the courage to buy my own panties and pretty things, sometimes from department and women’s clothing stores but my favorite place to shop for lingerie and dresses has become Thrift Stores. It just feels so extra girly knowing I’m wearing things a woman wore before me.

    • #403563
      Ria Freichuk
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      I had many pleasurable hours dressed in a former teachers lingerie while babysitting for her.

    • #403075
      Genevïéve
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      Mother’s panties when I was about 5 y/o. She caught me and did I ever get a scolding. In my teens it was her bras.

      Gen… 💋

    • #400248
      Wendy Me
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      My moms from the hamper in the bathroom while I was filling the tub. Never took from my mothers drawer as she would have know because it so neat. On the other hand my older sisters lingerie drawer was a mess and she would never know, I was careful not to dirty them but if it did happen I hand washed them and then air dried them and replaced them the next day, never got caught doing it.

      • #405111
        Genevïéve
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        No sisters… 😥

        Gen… 💋

    • #400234
      KHeart
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      My own. When I was growing up, I wanted to wear skirts more then any other female clothing. It was only when I was in my 20’s that I started to realize that I probably should start looking at other items to complete the look, so I ordered my first panties online and immediately fell in love with them… so then I started to order more and more, and other lingerie.

      …And now I’m hooked! 😜

    • #400233
      Rei Durden
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      My Aunts! She had the most awesome selection of heels, panties, stockings, garters, corsets. Nearly blew my little teenage head off when I found them while babysitting my cousin. And she had silk bed sheets! Some of my fondest memories as a teen.

    • #400225
      Elaine Nightgown
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      From the age of 9/10 it was always mother’s nightdresses and slips when she was out. I always loved the feel of them, still do today 50 years later.

    • #363558
      Emily Lace
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      My first experience was playing dress up with my sister. She put me in a cute little dress, a pair of her panties, and a pair of her sandals. We were having a blast playing sisters until my mother caught us and told us to never do that again. Something stuck with me though and a year or so later I saw a pair of my sister’s baby blue nylon panties in our shared bathroom. I had an incredible urge to try them on. Once I slipped them up my legs, the feeling was unreal. From that point on, I knew that had had to wear nylon panties as often as possible. I quickly added slips, baby doll nighties, and pantyhose to my secret dress-up times as well. I continued to “borrow” my sister’s panties and other lingerie until I was old enough (and brave enough) to purchase my own.

      Such great memories!

      Hugs,

      Emily

    • #363258
      Caroline OBrien
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      I touched and tried on my mum’s bra as a young boy probably around 10 years old. I wasn’t really sure what it for!!

      At 14 I started baby sitting for a lady friend of my parents. I tried on everything in her lingerie drawer over the span of a few months. that was Crossdresser Heaven!!!

      -Caroline

    • #360463
      Kimmie
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      Such sublime memories.

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    • #360427
      Anonymous
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      It was my moms french knickers and pantyhose I was only 10 or 11 and loved the feel of them against my skin.Then it was my sisters we were both the same size in my early teens I used to borrow her bras and panties and now all these years later I have my own collection of lingerie bras panties stockings pantyhose and bodysuits even have french knickers and even now wearing my silk panties.

      Hugs and kisses

      ❤💋❤💋❤💋

       

      Kelly Ann💋

    • #360021
      DaniJ
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      I was around 10 and had a couple hours alone after school and I would wear my mom’s panties and bra.  Loved how it felt.  Taken me over 50 years to recapture that feeling.

       

    • #358811
      Emily Alt
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      My very first time I was 4 or 5 when I tried on a bra in the dressing room of a department store. My aunt caught me and I got a stern lecture.

      The first time I consciously desired to crossdress I was 11. I wore my mother’s pantyhose – which I found hanging in the bathroom. A few days later I wore a bra, panties, pantyhose and slip. I dressed whenever I got a chance. By the time I was 13 her things didn’t fit and I knew she’d catch me if I kept wearing them. So I found “other” nearby sources and built a sizable stash. Not something I’m proud of.

      I moved away from home when I was 20. That’s when I started buying lingerie and discovered how expensive it is.

      Emily

    • #358298
      Sarah C
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      My mother’s black slip. I was 12, and my parents had left for church for the morning. I then put on a pair of her control panties, hose and a black bra. It felt amazing – the tightness of the panties and bra, the softness of the slip, the rub of the nylons. I wore them as often as I could after that. When I had the chance I wore everything possible, and even put makeup and perfume on. I was never caught.

       

    • #356172
      Paula Aguilera
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      Thank you, I was lucky in that sense, at home I was myself, I was totally girly, talk, walk, dress. But on school it was really hard, all the boys and some bigger girl always pick on my, even some teachers would treat me rough. If I had to go to the bathroom, some boys would touch my butt, call me faggot, sissy, little bitch, and stuff like that, that caused me to stay even closer to my sisters, I was just afraid to go to school, it set me up for a lifetime of denial. I want to get out and be the girl I feel I am, but it is so hard

    • #355439
      Daeyton Jayde
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      In my 20s I got involved with a woman who was Bi-curious, and wanted to dress me up and fool around, just to try it out. She started buying me feminine, but really slutty things, (6 inch black patent stilettos) and encouraged me to shave my legs for her, did my nails, etc. She liked it Way More than I did.
      Eventually we did involve other women in our sexuality,(including a professional cheerleader) but then it turned into was one of those relationships which burned out fast.
      Later in life when I was single and missing having a sexy woman around, I took it on myself to be the sexy woman I wanted,… red wig, breast forms, makeup, jewellery, and less slutty, better fitting and looking outfits. The click of heels in my house is very soothing.
      Eventually I bought out a few stores closing and was able to keep a bunch of great clothes, and sell off the rest for profit. One was an adult store full of shoes and lingerie. I made a killing on back then, before online shopping was really big, and CDs/TSs were gobbling up everything I had to sell, as fast as I could list it.

    • #355369
      Janice Fadden
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      I remember playing with my two sisters, and dressing up completly, pantys, dress, wig, makeup, accesories, my sister shoes, and i pretended to had a baby, I fell so happy and free. I did continue to dress all the way until my teens.

      That is the childhood I wish I’d had. Lucky girl.

    • #355368
      Janice Fadden
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      In my teens when I was left home alone I would go to my mom’s underwear drawer and put on a pair of her panties and a bra or sometimes her other lingerie. I felt it was unfair that my clothing was rough while her’s was so soft against my body. I also didn’t understand why my female friends hated bras I loved and still do love wearing them.

      YES YES YES

    • #355043
      Juliet Blisston
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      In my teens when I was left home alone I would go to my mom’s underwear drawer and put on a pair of her panties and a bra or sometimes her other lingerie. I felt it was unfair that my clothing was rough while her’s was so soft against my body. I also didn’t understand why my female friends hated bras I loved and still do love wearing them.

    • #355040
      Paula Aguilera
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      I remember playing with my two sisters, and dressing up completly, pantys, dress, wig, makeup, accesories, my sister shoes, and i pretended to had a baby, I fell so happy and free. I did continue to dress all the way until my teens.

    • #354506
      ChloeC
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      Sometime in my early teen years I got the nerve up to try on something of my mother’s. I can’t totally remember but I think it was either a girdle or all-in-one.  She caught me on maybe around my 10th (or even later)  time.

    • #354499
      Bobbi
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      Mommy’s girdle & garter belt.  (They were enormous on me, as I was 4 or 5 yrs. old!).  LOL

      Grandmother bought me all kinds of girly things.  I miss her.  🙁

    • #354450
      Casey Amber Twitchings
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      To this day I have no idea whose panties they were. Back when my mother still did my laundry a pair of navy blue nylon panties showed up in my laundry. My mother washed and dried my clothes but I folded them and put them away so she didn’t know they were in there. I resisted for a short time, then I put them on. It was equal parts thrill of actually wearing panties and the feeling that it somehow felt right.

      They never got those panties back. That’s one of the biggest regrets of my life, crossdressing or no.

    • #354415
      Kay Anderson
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      My father used to get Fredrick’s of Hollywood catalogs. I used to look at them when no one was home. I wanted to wear lingerie like all the models in the catalog. I found a pair of pantyhose that my mother was throwing away, it had runs in it. I cut it apart and found some elastic, needle and thread. I was trying to build a homemade garter belt and stockings for myself. I am guessing I was probably 13 at the time. Well my project failed miserably! At least I tried! Now I can just buy nice lingerie and wear it without worrying about parents and older brothers catching me!

    • #353942
      Nina Green
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      It was my mom’s bra. I still remember that day and the feeling.

      There were some of her clothes in the bathroom and I was having a shower. Curiosity made me put on her bra and look in the mirror. Strangely exciting!

      But the first real time was a few months after that. I was home alone and was going to be for a while. I picked up a bra from the clothes line and tried. Had it on a for maybe 15 minutes. What an exciting feeling!

    • #353937
      Amanda Huntress
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      I grew up with 3 older sisters and started with their stuff. I didn’t have to steel it or go taking it from their rooms.  Across the hallway from my room was a big storage space and in playing in it one day i found boxes of their old clothes including underwear. First thing i ever got to wear was panties and a training bra, i was instantly attracted to them. And as they say the rest is history.

    • #353580
      Alice Underwire
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      First time wearing was my mom’s bra and panties.

      Alice

    • #353189
      Anonymous
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      Back in the day of latchkey kids, I had some time after school. I got into my moms underwear drawer. At first it was a pair of satin string bikinis. As wonderful as they felt, they quickly can off and replaced with nude, sheer to top pantyhose…thrilling and just as thrilling today.

    • #353184
      Wendy Swift
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      My mom’s panties was the first lingerie I tried on for the first time.

      She would leave her washed panties in the bathroom.  As a small kid I was curious so I felt the material and it was so soft and smooth, compared to the rough burlap tightie whities I was wearing.

      One day after school, I went home and I tried them on.  It felt so good, it was comfy, smooth to the skin, I was hooked.  Of course being small I had no concept of time whatsoever; I sat there watching TV in my mom’s panties when I heard the front door unlock.  I must have made the quickest change in history, as I took off my mom’s panties and put on my tightie whities.  My dad asked why I was sitting there in my underwear, and I remember saying I felt hot.

       

    • #353062
      Kimmie
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      I answered this originally a while ago and, while reading my answer, I remembered — or interpreted the question differently. In any case, here goes. My parents had friends who we called Aunt and Uncle. Once, I tried on a pair of my “aunt’s” panties I found in the laundry hamper in their bathroom. As a kid, I played doctor with a girl down the street and a few times we “traded” underwear. I have general recollections that when I was young and I had the opportunity, meaning the availability of panties and the relative privacy to try then on, I did. In retrospect, I’m not proud of those invasions of their privacy, but the urge was too strong for a young boy to resist.

    • #353046
      Jennifer McCrennaugh
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      Mom bought me my first pair of tights when I was 5. Orange Danskins.  She saw me trying on my sister’s and rather than let me ruin hers she got me my own. It must have worked. I never wore my sister’s things again.

    • #353043
      Christine C
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      hello.
      are you still active on this site.
      have not been on myself for a while

    • #218678
      Caty Ryan
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      Mu mothers when I was about 10. (I’m one of two boys, no no other females in the house).

      This led me to a life long love of things femme, I especially remember the open bottom and closed leg panty girdles. Bras with tennis balls for boobs!! (Very scratchy on the chest).

       

      Caty

       

       

    • #217964
      Kristen James
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      My first time putting on lingerie or my first time crossdressing at all was when I was 12 and found a pair or my older sisters satin bikini panties in the wash. Ever since I felt the smooth soft satin against my skin I’ve been hooked. I was a teenager in the 70s, so my sister who is 5 years older than me had some really fabulous clothes,  panties,  dresses bras, and they all fit me. She also wore Leggs pantyhose which are still my favorite. She had some really hot satin disco dresses and heels, …it was so much fun.

      • #219388
        Christine C
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        Your extremely lucky to have an older sister. Wished that I had one too, although my mother had very sexy lingerie. What got me into this mess. Lol well a good mess.

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    • #207896
      Zoe Strange
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      I started with mums she had some lovely tiny lace bikini knickers in a dark blue I can still remember them now ,then things progressed to my twin sisters fishnet hold ups wow they were sooo sexy.

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    • #198612
      Patty Phose
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      When I was 4 I developed a fascination with women’s legs in nylons. I liked to get close to them and see the mesh and touch them. My parents were naturally not pleased with this.

      My dads methods to stop me were harsh. Mom, not liking that thought if I had my own nylons I could enljoy them without bothering the ladies. She gave me my own stockings and soon after pantyhose.

    • #198491
      Courtney
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      I would wear my mother’s bra and tights at a very young age around 6 year old, I would stuff it with anything just really wanted to feel like I have breasts, she caught me almost straight away then I never touched anything, until I was 13 and found a padded gel bra she had and It obsessed with it. It was just like wearing a pair of breasts and then it came a real obsession even when visiting friends houses if there was a bra I would try it on, and then as I’ve grown up I will try on girlfriends bras etc. Now I have my own collection I keep hidden.
      <p style=”text-align: left;”>Ps this is my first post so go easy.</p>

    • #198471
      Rachel Toni
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      Mom used to leave her bra and panties in the bathroom after she had a bath. I was next in line for the bathroom of an evening as a youngster. And luckily the bathroom was the only room with a lock on it.

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      • #198486
        Anonymous
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        That’s what I call fate or destiny Rachel. Imagine how unfortunate both you and us would have been if you hadn’t been next in line.😉

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        • #198598
          Rachel Toni
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          I was even luckier when she left all her clothes for the day in the bathroom. I was 12 and it was the first time I fully dressed. Alas, she only did that once…so I learnt to improvise… 😉

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          • #198599
            Anonymous
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            I can remember the feelingsthat brought on. School holidays when a teenager is alone in the house. Happy days😃

            Improvise you might have to tell me how that went, privately if it spares your blushes😉

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          • #198602
            Rachel Toni
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            Totally! I was so pleased once I was old enough to be left on my own. Coming home from school to an empty house or those long holidays. I used to enjoy being able to walk around the house (curtains drawn, obviously) in full dress. Alas, it wasn’t that often and I soon outgrew my mum’s (only pair of) stilettos.

            There are plenty of blushes I can bore you with!

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          • #198604
            Anonymous
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            Bore away.

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        • #198567
          suchi R
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          Exactly! Well said Donna.

          I feel very lucky that I got the experience of this cross-dressing. It’s one of the very special feelings in our lives.

          • This reply was modified 1 year ago by suchi R.
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    • #198303
      Ellie87 Pinsk
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      Back when I was a younger lass, I stayed with my great aunt for awhile so I wore her daughters panties and her husbands Yankees Jersey, just because I didnt have Jammies For the night.

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      • #198468
        suchi R
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        Great. Did you get permission to wear those panties? Just curious 🙂

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    • #196695
      K Swim
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      Registered On: July 8, 2019
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      Older sister was the closest to my size when I started.

      5 users thanked author for this post.
    • #196615
      helenmarie
      Participant
      Registered On: August 1, 2018
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      Hello Suchi,       I started with my mothers but they where a little to big. I then wore my cousins [ she was about 4 years older than me ] they where great. I did wear some of my friends daughters clothes for quite awhile, that was a lovely time while it lasted, but have stopped borrowing others peoples clothes as it not the right thing to do. I always by my own now,    love,  Helenmarie

      4 users thanked author for this post.
      • #198469
        suchi R
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        Registered On: February 20, 2018
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        Wow…you got to try from so many closets. Lol 😀.  Great to know that you have setup your own wardrobe.👍

        2 users thanked author for this post.
    • #196111
      Kimmie
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      Registered On: September 27, 2016
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      I started with my mom’s lingerie. This was the early 60s and my mom was about 45, so she had a number of panty girdles and that was how I started. Eventually, I added stockings and later pantyhose, bras, etc. I’ve never lost my love of pantyhose and a firm girdle.

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      • #198470
        suchi R
        Participant
        Registered On: February 20, 2018
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        Rightly said. Pantyhose and girdle are always an epic and elegantly sexy combination. Have you tried any now vintage clothing at that time?

        4 users thanked author for this post.
        • #198472
          Kimmie
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          Registered On: September 27, 2016
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          Not really. My interest in cross dressing is very limited as compared to most of the girls here. I do not feel like a woman in a man’s body, want to be female, or otherwise to pass. (BUT, I fully support all those who do.) So, other than some stiletto heels (because I love how my legs look in them), I don’t really do more than “under dress.”

          • #198569
            suchi R
            Participant
            Registered On: February 20, 2018
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            Cool. That’s perfectly fine. Everyone’s likes are unique and we respect all and each other.

            3 users thanked author for this post.
    • #195262
      Natalia K. Lanvaldear
      Participant
      Registered On: May 16, 2019
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      I started with my cousin’s. Always exciting when she isn’t home, then got the chance to enter her room and explored her lingerie drawer. Her bras were so adorable that I couldn’t resist not to wear. Been doing that for years without getting caught.

      4 users thanked author for this post.
    • #195217
      Paula Pantyhose
      Participant
      Registered On: September 8, 2017
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      I was in jr high and a friend dared me to put on my Mom’s pantyhose.  I did not do it while he was there but later I did and I was hooked, I have been in love with pantyhose since.  Mom never said anything to me but most likely she suspected someone had been in here things, I don’t think I will ever tell her, because it would also require me to tell the rest of the family and my brother would most likely never accept Paula.

      Then and when I found heels they make the perfect pair, Pantyhose and Heels.  They make me feel so fem.

       

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    • #195010
      Anonymous
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      Without a doubt it was my lovely mother’s lingerie when I was young I didn’t need a girdle but I loved it because of the garter straps to hold up my mother’s sheer nylons lol

      4 users thanked author for this post.
    • #194838
      Anonymous
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      I started wearing my sister’s bras, panties and girdle. It was so exciting. When I got older it was my wife’s things and finally started buying my own. It is very empowering to go into a store and when the lingerie department to pick out items and when the same asks who they are for I reply for me…

      5 users thanked author for this post.
    • #194573
      Emily
      Participant
      Registered On: April 30, 2016
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      Easier question would be, whose haven’t I tried. Lol. Until I got my own substantial collection, I was not at all discriminating about finding undergarments to wear. Not proud of it, but I actually stole 2 pairs of bikini panties and a pair of pantyhose off a neighbors clothes line once. Oh but I enjoyed wearing those!

      4 users thanked author for this post.
    • #194569
      Jamie Vegas
      Participant
      Registered On: May 23, 2017
      Topics: 4
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      Ex-wife and I worked different shifts. When I got home at 8AM I would dress up in her clothes and relax before I went to bed.

      3 users thanked author for this post.
    • #194550
      Celeste Starre
      Participant
      Registered On: June 26, 2018
      Topics: 26
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      I was around 12 when I first started and had no sisters so that left my mother. Sadly her tastes were rather plain but it was all that was available.

      6 users thanked author for this post.
    • #194492
      Janine
      Participant
      Registered On: October 25, 2015
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      When I was about 12 years old I would go into my sisters room when she wasn’t home and borrow from her dresser a bra and panties then borrow from her closet 3 petticoats

      I still remember them as being pink blue and white. I’d take everything in my room and put it on then look at myself in the mirror and think how feminine I looked. I never got caught doing this but my sister was suspicious when her thing’s weren’t put back exactly like she thought they should be

      4 users thanked author for this post.
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