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  1. #26
    Member kimberly c's Avatar
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    6 or 7 I put on my mom's panties and bra. It just felt so right I always went to bed hoping to wake up as a girl.

  2. #27
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    How old were you when you first wore an item of women's clothing? Around 2 or 13.

    What item of clothing did you wear first? A pair of sheer pantyhose.

    Who did the clothing belong to? A girl at school I had a crush on.

    Why did you wear it She had been wearing them and it was a sexual thing at that time.
    Last edited by Donnaph; 06-12-2020 at 06:59 PM.

  3. #28
    Silver Member Kandi Robbins's Avatar
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    How old were you when you first wore an item of women's clothing? 5 years old

    What item of clothing did you wear first? A dress, I can still imagine how it felt.

    Who did the clothing belong to? A neighbor.

    Why did you wear it? I was five, what did I know?
    Visit Kandi's Land (http://www.kandis-land.com/) daily! Nothing but positive and uplifting posts!
    Pictures and stories of every time out: https://www.flickr.com/photos/131254150@N06/.

  4. #29
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    I was four years old.

    It was a pair of pink girls panties, with little frills around the edge. The only underwear available at the time.

    They were a spare pair belonging to Emma, a fellow classmate.

    I wet myself in class because I was too scared to tell the teacher that I needed the toilet. Teacher took me to the bathroom and cleaned me up. When I stepped into the panties and pulled them up they just felt right. They made me happy.

  5. #30
    Nylons lover GeorgeA's Avatar
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    About 5 and tried my aunt's nylons to see if they fit my legs. They did not. They were too long for my short legs. Now I wear nylons all the time and they fit.
    GeorgeA
    formerly Salerba

    "a miad" Man-in-a-Dress

  6. #31
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    How old? I really cannot remember. I do remember I had to be very young because I had to stand on the edge of the bathtub in order to get my mother's slip down from a drying rack.

    I like the feel of my mother's nylon slips that she hanged in the hallway to dry. I would pass them by on the way to my bedroom. I loved the feel of the nylon. It was like no other clothes I had encountered.

    I had no desire to be a girl. At that time it was purely the feel of the nylon. Later I discovered her floor length nylon nightgowns.

  7. #32
    Always been a GIRL. Michelle1955's Avatar
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    Making me think back 60 years.

    How old were you when you first wore an item of women's clothing?
    Female / girl clothing actually probably 3 years old.
    Panties about 5-6 years old.

    What item of clothing did you wear first?
    Little Girls everyday dresses,etc. and panties.

    Who did the clothing belong to?
    A neighbor girls playmates I played with daily.
    No boys my age on the block I lived on. Only a few girls so grew up playing with girls and girl activities.
    Girls Panties at 5-6 years old while we were in her bedroom playing, she also wore my underwear.
    We were afraid of being caught by her mother when she yelled out from the other room.

    Why did you wear it?
    I grew up with the girls playing together, it just felt right in my head to try the panties on since I had played dress up for a long time already.

  8. #33
    Senior Member TheHiddenMe's Avatar
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    I was 6 or 7 and there was a girl's dress in the shared basement and my aunt and uncle's condo/co-op in Chicago. There were two other units so I don't know who it belonged to. I tried it on, but it didn't fit.

    As to why, I still don't know to this day. But the urge has never gone away.

  9. #34
    Member Chelsea B's Avatar
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    I was 14 and just had to know what it felt like to wear a dress.

    One of my Mother’s dresses. From there it quickly moved to full underthings, as full fem as I could achieve with what I had to work with. I was hooked immediately.
    Not a woman, I just enjoy looking and feeling like one now and then!

  10. #35
    Aspiring Member jacques's Avatar
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    How old were you when you first wore an item of women's clothing? about 8

    What item of clothing did you wear first? tights

    Who did the clothing belong to? sister

    Why did you wear it? I wanted to be Robin Hood

  11. #36
    Silver Member Kay J's Avatar
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    I was 5 or 6 moms nylons i just love the feeling of them on her legs so i had to try them on myself and never have stopped and never will!

  12. #37
    Senior Member SaraLin's Avatar
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    How old were you when you first wore an item of women's clothing?
    4 or 5. I'm not sure which. If I did it earlier than that, I don't remember.

    What item of clothing did you wear first?
    a dress.

    Who did the clothing belong to?
    My sister.

    Why did you wear it?
    Because I wanted to be a girl too.

  13. #38
    Connie Connie D50's Avatar
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    I was 8 my mom would leave all kind of thing laying around in her bathroom Panties first. Felt great added matching teddy (powder blue) remember it like it was yesterday. (still love teddys to this day have a great collection)

  14. #39
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    Hi Jacques , It was my Moms nylons and hi-heels when I was 4yrs. old. >Orchid ..++..
    Having my ears triple pierced is AWESOME, ~~......

    I can explain it to you, But I can't comprehend it for you !

    If at first you don't succeed, Then Skydiving isn't for you.

    Be careful what you wish for, Once you ring a bell , you just can't Un-Ring it !! !!

  15. #40
    Member Katherine L.'s Avatar
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    How old were you when you first wore an item of women's clothing? 11 or 12

    What item of clothing did you wear first? Bra

    Who did the clothing belong to? My mom

    Why did you wear it? Found it in the clothes hamper and just decided to try it on.

  16. #41
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    my age at first remembrance; 5-6

    item;my sisters dress when she was much younger ( she was 10 years my senior)

    why: she wanted a little sister but had to be our secret (I was too effeminate to be a little boy, she told me quite often to hide my feelings from others)

  17. #42
    Silver Member
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    about 5 or so. my sisters panties. My mother had me wear them since I didn't have any clean underwear.

  18. #43
    Struggler with CDing Pixie_94's Avatar
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    1. I was 10 or 11, if I remember well.
    2. They were some panties.
    3. I prefer not to say.
    4. I saw them and felt curiosity. That's when this mess of a story began.

  19. #44
    Member Jeanettew's Avatar
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    How old were you when you first wore an item of women's clothing? 35

    What item of clothing did you wear first? Stockings and high heels

    Who did the clothing belong to? I bought them

    Why did you wear it? I love the feel of nylons when I have touched them and was in a shop one day and saw a display and bought some and I then went on line and bouugh some high heels and waited for them to arrive before putting on stockin, then I started buying other cloths but my favorite is from the waist down Skirt Panties, Stockings and heals would love to be miad every day.

    Mind i do like to wear a bra and a dress, sorry for going on
    Last edited by Jeanettew; 06-14-2020 at 12:38 AM.

  20. #45
    Member helenejo's Avatar
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    About 6, a frilly lacy petticoat of my mums, i think I had an early frisson of sexual excitement wearing it

  21. #46
    Junior Member
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    1. Around 11 years of age
    2. A skirt
    3. My sister?s
    4.Due to an irresistible obsession

  22. #47
    Oh to be an English Rose Jane G's Avatar
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    Such a long time ago. I always used to dream about being a girl long before I tried on any items of clothing. I think I was around 6or7. I used to play with my cousins all girls except little young me. No idea what the first item would have been. About age 8 I started to wear my sister's clothes and then my mums. I soon got busted and my dad went shall we just say, well over the top. Been here hiding in the closet ever since.

  23. #48
    Senior Member kayegirl's Avatar
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    I am the 3rd born of 4 siblings, and whilst I would not say that we were poor, money was tight, so hand down clothing was the normal. Problem was that by the age of 3 I was as big as my older brother, so any hand downs came from my older sister. No skirts or dresses, but plenty of t shirts, jumpers and knitwear, and plain white blouses. Most kept for playtime when it didn't really matter. Also passed down were pj's. I remember them as being much more comfortable than the boy pj's.

  24. #49
    Aspiring Shopaholic BTWimRobin's Avatar
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    My aunt has photos of me dressed to the nines in her clothes. I was probably around 3 or 4 at the time. I'm not sure why. Maybe because I wanted to look like her.
    - 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!

  25. #50
    Connie Johnson connie johnson's Avatar
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    Hi all.

    How old were you when you first wore an item of women's clothing? 8 or 9.

    What item of clothing did you wear first? Pantyhose.

    Who did the clothing belong to? Mother

    Why did you wear it? Liked the way they felt in my hands.

    Connie
    Connie

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