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Thread: What was the first time you wore?

  1. #26
    ~ Bondage & Pantyhose ~ cosmolovesph's Avatar
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    I know I was in elementary school and wore Pantyhose under my pants to school ... not sure on the exact age.
    ~~~~~~~~~~~~~~~~~~
    Crissandra
    ~AKA - Cosmo-Loves-PantyHose~
    Don't forget to compliment those wearing pantyhose, as to how nice their legs look!

  2. #27
    Gold Member Sometimes Steffi's Avatar
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    What I don't understand is how a 5 y.o. boy can wear his mom's slip or pantyhose or anything. Aren't they way too big?.
    Last edited by Sometimes Steffi; 08-01-2020 at 09:16 PM.
    Hi, I'm Steffi and I'm a crossdresser... And I accept and celebrate both sides of me. Or, maybe I'm gender fluid.

  3. #28
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    (This same story is in "Heels" thread, elsewhere)

    I was in 7th Grade, home alone, reading a cheap paperback in which one of the characters is described as wearing high heels. Pow. I got a pair of my sister's heels and put them on. Haven't stopped since, except when I was caught.

  4. #29
    Gold Member Lana Mae's Avatar
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    First time I wanted to was at between 5 and 6! A playmate(Lana) threw her dress over her head and I thought that was great and I wanted a dress! Of course,I was a boy and boys don't wear dresses! Early teens was mom's panties! That was the first wearing! Hugs Lana Mae
    Life is worth living!
    "Foxy lady! You look so good!!" Jimi Hendrix

  5. #30
    Senior Member Angela Marie's Avatar
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    I was about 10 years old and tried on a pair of my moms black tights (now called leggings). Hooked immediately.

  6. #31
    Member ClaudineD's Avatar
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    Very early on...but the crowning moment was at 16 when my Aunt took me shopping as Claudine in NYC.....she was a great advocate and instrumental in incorporating my Mother at early age

  7. #32
    Aspiring Member Lacey New's Avatar
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    I don?t remember the exact time but I was a young teenager 13, 14 or maybe as late as 15. But back then girls wore miniskirts to school and by dropping a pencil in class and looking backward, I would be rewarded with a peek of panties. And thinking about what was under those panties was sexually arousing. I also had access to Sears and Penny?s catalogs that showed some lovely lingerie. Well, eventually, I found the laundry hamper where my mother and sister deposited yesterday?s parties. At first, I would just hold and feel the panties as I would take care of business and then the inevitable happened and I put on a pair of nylon briefs. I?ve been hooked ever since.

  8. #33
    Senior Member BrendaPDX's Avatar
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    I was a freshman or sophomore in high school, I was at a thrift store and ran across a dress. I liked it so much, hands shaking I stepped up and bought it. I tried it on that night, it had a side zipper (I hand never seen that before), the dress pulled around me as I zipped it up and fit me perfectly! I looked at myself in the mirror for several minutes, I was hooked!

  9. #34
    Aspiring Shopaholic BTWimRobin's Avatar
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    Growing up we didn't have a cloths dryer so mom would always hang the laundry up in the basement to dry. Since the basement was also my playroom, I had access to bras, girdles, slips .... all hanging there just begging for me to try them on. And try I did and was completely addicted. Mom used to dry her stockings in the bathroom and I would slip them on every chance I got. Absolutely love the feeling.
    - Robin


    Because life is too short not to.

    It's ironic ... I finally found a group of guys I fit in with. Funny how they all enjoy being one of the girls.

    Wife: Why do you fold your panties? Me: I don't like my panties in a wad!

  10. #35
    Member Denice's Avatar
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    I was maybe 10 or 11 when I slipped into a pair of fishnet stockings.
    I'm a man. I like being a man. I also love wearing women's clothing. It's my way to show honor, respect and solidarity with them.

  11. #36
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    My sister dressed me in her ballet tutu when I was about 6. She showed our mother who I remember saying "don't do that - he may want to do it again". Famous last words....

  12. #37
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    I was 13 when I started. Wore a beautiful foral print dress which felt wonderful.

  13. #38
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    At some point during a hot summer evening of my (very) early teen life, when my parents were away, I did something really bold. I wore a complete feminine outfit while bike riding around in my neighbourhood. I had on a cap, bra, panties, denim short shorts, a thin t-shirt, and a flannel button up shirt tied about my waist. On my feet were sneakers. I walked into a convenience store and I purchased candy or a magazine; I forgot which exactly. But I do recall my heart was thundering the whole time!!

  14. #39
    Member Charlotte Haynes's Avatar
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    I was 10. It was during the school Summer break. We usually stayed at my grandparents, but as I was doing some cycling course in the mornings, I stayed home alone. This was a first.
    I was obsessed with tights/pantyhose, and during this time I can recall rummaging through my Mams drawers for some. I liked to touch them. This particular time I pulled them over an arm, then over a leg, then panicked. I put them back and went downstairs. A few minutes later I was back up there, and the urge took over, and there I was standing in front of the mirror wearing my Mams black pantyhose. An electric feel. Over the next few days I repeated this, and also wore a tan pair with heels. I remember wearing a girdle and a slip, but never panties. They seemed a step too far.
    Last edited by Charlotte Haynes; 07-09-2020 at 07:32 AM.

  15. #40
    Member VivianNewkirk's Avatar
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    I vaguely remember playing with my mother's clothes as a child, but that wasn't really formative or influential. I didn't start seriously crossdressing until much later, in my 50s. I started with a set of lace panties that I would wear all day under boy clothes. Things escalated quickly from there! At first it was for kinky sexual arousal (as my pansexuality awakened) but soon I was dressing just because I liked to. I now consider myself gender-fluid and am trying to hone all aspects of my femininity.

  16. #41
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    I started very young. I can't remember exactly when it started. I do know that my sister was born one year after me, and I envied the attention my mother gave her. My mother would tell me that I was very clingy and I was jealous of my sister. I have memories as early as 3 years old when I would rummage through my mother's clothes, and enjoy twirling around in slips, skirts, and just about anything I could find. I remember being scolded for it, and telling my parents that I was playing "mommy". I believed that my mother would love me more if I was born a girl. At one point at age 4 my mother made me a dress. I tried it on and immediately started twirling as my mother laughed. My older brother saw me and laughed hysterically. I started crying. My father came in, and put an end to my dress. After that my parents were very strict and put an end to my early crossdressing.

  17. #42
    Lady in waiting Peggie Lee's Avatar
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    As far back as I can remember around 4 I would play dress up in my mother?s clothes when ever my parents were not around until about 9 then stopped after being caught but at 12 I had a girlfriend that would let me wear her clothes as we were the same size, my happiest memory was dressing in her Girl Scout uniform with her selling Girl Scout cookies door to door. It all ended with my brothers death when one of my dad?s customers after seeing me said To my dad he liked the cookies my sister sold him ( I don?t have a sister).

  18. #43
    Platinum Member Angie G's Avatar
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    I was about 10ish dressed with things stored in the attic of the apartment building. and still dressing 60 years later.
    Angie

  19. #44
    Princess Candice candykowal's Avatar
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    I was a sick baby and slept with my Mother when my Dad was away for work from 2 to 5 yrs old.
    Mom dressed me in a baby girls satin nightgown and plastic pants.
    Mom coddled and pampered me due to my illness of being underdeveloped.
    I was there as she got dressed most days.
    At that age, I often emulated Mom when she was busy, she was my role model.
    I played in her room often with her lingerie, wearing slips, panties, high heels, jewelry, and makeup.
    So I was pretty comfortable around silky garments and nice smelling perfumes...reliving my past is just heavenly!

  20. #45
    Silver Member Maria 60's Avatar
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    The only thing I recall was I would share room with my sister, she was very messing and she would leave for school before me. One morning I was laying in bed and I couldn't help but notice a pair of biege pantyhose on the floor. I remember grabbing them and putting them on under the sheets in bed and POW! what a feeling. That was great and it starting escalating to skirts and bras but the most amazing moment was the feeling of a slip.

  21. #46
    Member mmandy31's Avatar
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    I was around 11 staying at my grans house she was next door and I seen a pair of her yellow silky panties so I picked them up felt so soft as I knew she wouldn't be home for awhile I tried them on just to feel what they felt like and I was hooked been wearing panties for 50 yrs now

  22. #47
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    I remember being very young and fascinated with my mothers bra. I had one hid behind my chest of drawers when a babysitter found it. I told him that she liked for me to keep them there. HA. Then I would try and girlfriends panties and I love all of the different styles of panties. Now, in my 50' I starting to love womens fashion.

  23. #48
    Junior Member Gia's Avatar
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    I think I was 12 or 13.
    It was one of my mum?s old mini skirts.
    It was made of nylon inside and was bright blue outside. I clearly remember it was one or two sizes smaller than mine and that kept my legs really close together. Walking in it was hard but turned me on like nothing else.

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