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I Want To Know What Influenced You To Crossdress

What made you say put on the panties ? 1,659 People

    School Halloween Carnival

    My first recollection of being aroused by the idea of crossdressing was when I was in elementary school. Every year, there was a Halloween carnival and you came to school in costume. I recall seeing another student, who was maybe a year older than me dressed up as a girl. He...
    jennyla73 jennyla73 36-40, F 1 Response Oct 12, 2012

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    I did it one time for halloween

    and then it took a few years for me to start back up this guy I knew ask me to do it for him and I have not stopped I love it now it's been two years if a great time
    kelliTxxx kelliTxxx 36-40, T 6 Responses Dec 30, 2015

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    I think its two things

    that did it for me. my mom left my dad when I was 5 months old spent the fist 5 years with just her and my brother and always wanted to be strong like her. secondly my penis never really developed and my testies never came down so I have more of a oversized **** than a ****. so...
    jamie172 jamie172 46-50, T 2 Responses Feb 8, 2015

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    I've responded once to this,

    but will elaborate. Why did I continue? I don't think it was the influence, but it was and x-y genetic thing that did it. The influence started something and my being kept it going. So, after these years, I still wish to wear clothing that is not considered masculine, don...
    1della 1della 46-50, T 2 Responses Oct 12, 2015

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    My Story

    My older stepbrother played with me as a kid while babysitting me. He told me not to tell so didn't. He came back more and more. I tried dressing to be someone else. He caught me and saw how it excited me and he liked it. So he guided me and my dressing. Bad attention was better...
    LadyLycra LadyLycra 18-21, M 15 Responses Oct 26, 2013

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    Michelle41011 Michelle41011 41-45, T 2 Responses Nov 15, 2015

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    The initial answer may sound strange,

    but I'll explain. It was the Sear's catalog. Ok, So here I was a teen age boy in the very early 70's. I can't say I never saw a Playboy or Penthouse but it was very hard to get your hands on them in a small Midwest town as a teen back then. But the Sear's catalog was...
    babybearjean babybearjean 61-65, M 8 Responses Jul 28, 2014

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    Basically the picture above How fit girls are?

    So I was home alone and it wasn't the dress. It was the makeup I love nail polish and on Saturday I went to get a pedicure and got my toenails painted red. I would always wear socks never go swimming because my parents knew From this time I've always wanted to be a girl or...
    EvaMarie1406 EvaMarie1406 22-25, M 5 Responses Nov 15, 2015

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    I Was More Who Than What Influenced Me To Crossdress.

    At an early age, around 8 or so, It was only me and my stepsister living at home with my stepmother.  There were no children our age in the neighborhood so we often took turns playing games with each other.   At times she would sit down to a board-game with me or and other...
    deleted deleted 26-30 12 Responses Oct 11, 2012

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    it stared out as a punishment

    for peeing in the bed, at the time i had a MAJOR dislike of crosadressing and was embarased by it, later years i found panties enticing so i tried them on & fell in love
    BabyCiria BabyCiria 16-17, F 1 Response Dec 28, 2015

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    When I was four years old I took all of my

    sisters pantys, that was in her old draw in my closet. I remember being so excited to have them for some reason. And remember my mom finding them while tucking me into bed. Then when I was 12 I would wear my moms bras and bed time sleep wear when no one was home. Last summer I...
    Pantylova Pantylova 18-21, M 3 Responses Jan 20, 2014

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    Why I Started

    When I was younger I always loved playing with my neighbor who was a girl and she would always put makeup on her older brother and one day I told her I wanted to try. So she put make up on me and I absoutly loved it! I now wanted to be a girl really badley when I turend 10 my mom...
    lime277 lime277 22-25 10 Responses Jul 22, 2012

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    Women's underwear! I tried a pair on

    when I was younger and just fell in ahh with the idea
    deleted deleted 26-30 Sep 26, 2015

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    I don't know why I picked up

    that pair of my Mum's panties out of the laundry hamper when I was about 12 but wow they felt incredible on. Just blew my mind. I think it was wearing something so intimate and feminine. I had my favorites and would look for them each time - especially the black stretch nylon...
    BrightLight750 BrightLight750 46-50, M 15 Responses Feb 21, 2015

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    the first I knew I loved to cross dress was

    when I was 13 and my sister had her very hot friend over for the night and they dressed me up in slutty clothes and heels and makeup, painted my nails, everything. than my sister went in the shower and her friend had a vibrator and asked if I wanted to have fun so I agreed and...
    Sexygurl221992 Sexygurl221992 22-25, T 6 Responses Sep 17, 2015

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    I have two older sisters,

    and each year in the spring and autumn we'd go through the hand me down ritual. I'd get any tee shirts or non gender specific clothes, though I wasn't allowed anything that was deemed too girly for me. I clearly remember my sisters having matching mini kilts, they had a huge...
    jo1966 jo1966 46-50, M 4 Responses Sep 13, 2015

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    How I Was Influenced To Crossdress.

    I started crossdressing at the age of ninteen while in college. I became involved with a couple and was asked to wear lingerie as part of our playtime by the wife. Her husband enjoyed dressing. After some initial misgigvings, I found that I enjoyed how I looked when dressed. I...
    mspenny mspenny 56-60, M 11 Responses Feb 27, 2012

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    For me it was when I was about 10 swapping

    socks with my cousin of same age. She had on a pair of green knee socks and I remember how they felt so much softer than my own socks. It was only when I had to swap back that I realised I didn't want to. At a sleepover at her house I got a chance to try on a pair of her white...
    Kneesocks39 Kneesocks39 46-50, M 1 Response Sep 25, 2015

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    when i was 12 i was influenced by my neighbor.

    we where playing a truth or dare game at a sleep over and she dared me to wear her power puff girl panties. so i did and i found them so comfertable. she went an said that i look good im them and to keep em on. so i did. after that night she gave them to me. still have them and...
    razgrizizzy razgrizizzy 26-30, M 4 Responses Mar 30, 2015

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    Woke up after sleeping with a girl,

    saw her underwear on the floor, went for it.
    Foxanne Foxanne 22-25, T 4 Responses Sep 25, 2015

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    Being Pampered

    I grew up with 2 older sisters that would dress me as their little sister all the time. My mother thought it was harmless play and later she started to take part. To me the clothing was just so natural and I thought all boys did this. Later in life I found out that this was a...
    femboy4u femboy4u 22-25 10 Responses Aug 13, 2011

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    Long Ago

    I actually started when I was very young! 4 sisters and all those pretty clothes! I unfortunately kept it buried deep and other then the short intervals of alone time i kept it secret! 2 years ago I confessed to my wife and the needs are no longer hid!
    Candicegirl Candicegirl 51-55, T 8 Responses Sep 5, 2012

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    Its hard for me to remember exactly what

    started it, but at a very young age I became fascinated with girls shoes. It could have started when in grade school and the girls I used to play with would wear their Black Patent Mary Jane's and tights. I do know that I always really liked those shoes and still do to this day...
    jamie50 jamie50 51-55 5 Responses May 23, 2015

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    First Compulsion.

    I was brought up on a rough estate, with my Mother and two sisters who were aged either side of me. I cannot remember my father ever being around. Even though I used to enjoy soccer and boxing I used to take sneaky previews of my sisters' girlie comics from a very early age. When...
    chloesiobhan chloesiobhan 56-60, T 14 Responses Oct 30, 2013

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    After my parents got divorced

    when I was ten, I was living with my Dad. He was bisexual and had a boyfriend that stayed with us. On some weekends I would stay at his boyfriends parents house with his sister, she was my age. We would share a bed and we both would only wear t-shirts and underwear to sleep in...
    Michelle1976 Michelle1976 36-40, T 4 Responses Aug 16, 2014

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    I was maybe 14 (not really sure of the age)

    and my friends who were girls were texting me. Well I got some random text from a guy who thought I was his girlfriend (wrong number). I told my friends and they thought it was funny and started calling me their sister and treating me like I was a girl. Well the idea made me...
    KayleeCD KayleeCD 18-21, M 7 Responses Nov 28, 2015

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    My First Time

    I was 11 , home alone and bored. I have an older sister who was 14 at the time so i went into her room to look for some books to read and i saw her underwear everywhere. I picked up if i remember a pair of pink panties with lil blue flowers on them and had the urge to take off...
    brentteenboy69 brentteenboy69 18-21, M 11 Responses Aug 5, 2012

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    I have always fantasized a lot about my wife,

    so eventually (LOL, less than a year married) I put on a pair of her panties and pretended I was her dancing, and it just kind of took off from there.
    ridel ridel 61-65, M 8 Responses Mar 9, 2015

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    Led Into It By Two Older Girls "modeling"

    i was younger and they were in highschool. it started inocently enough. Amber wanted was a girl who moved onto my block and i met her the day the moveing trucks came to her house. soon i was over twice three times aweek and another girl she met at school started hanging out too...
    laurielovecock laurielovecock 31-35 4 Responses Jul 1, 2012

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    It started after my wife asked me to put a pair

    of her panties on during sex. After that i was curious and started to try stockings, bra's and skirts. I'd spend my days off, dressed in her things, while she was at work.
    deleted deleted 26-30 6 Responses Sep 23, 2015

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    I was 5, & my best friend was the Girl next

    door. I watched all the children's shows then--I fell in Love with Shelly Fabres from the Donna Reed show, she wore the cutest dresses. I was always envious of all the pretty things Girls were able to wear-------------I still am & really want, even at my age, to have a Girl help...
    carolannP carolannP 51-55, M 5 Responses Jan 5

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    I'm not 100% sure about this

    but I think part of it had something to do with my sister and I sharing the closet in my room when we were little. I clearly remember seeing her dresses and jackets hanging there. I remember trying a pink jacket on. At some point her clothes were moved into her closet and I...
    cracklewalk cracklewalk 46-50, M 3 Responses Sep 29, 2015

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    it all started with my older sisters cloths.

    .. we use to have a lot of teen age baysitters when we were young and my sister always wanted to play dress up. I think the baby sitter had more fun with me then my sister I loved it! I have found old pics of me dressed in girly dresses pantyhose make up as a young child I only...
    crossdresserfun crossdresserfun 22-25, T 2 Responses 5 days ago

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    Crossdressers have always facinated me.

    So I enjoyed seekng them out in chat rooms hoping to find one showing off on a webcam. One particular night the chat room was dead. No crossdressers just a bunch of men. I saw my wife's nail polish sitting on the desk I decided I to paint my toenails on my webcam and see if I...
    chrissyk48 chrissyk48 46-50, M 6 Responses Jan 27

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    I was home alone one day

    and I saw it on some cartoon shows so I started wearing my moms panties and then her bras the all of her clothes and I never stopes yet
    People1313 People1313 13-15, M Nov 4, 2015

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    CDjan CDjan 51-55, M Jan 5

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    experience that I had,

    started when I was in my teens,wearing panty hose,& then early 20's panties,and other lingerie.
    Jacen101 Jacen101 41-45, T 2 Responses Sep 19, 2015

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    Adolescence in the early '70s,

    the fantastic days of pantyhose and miniskirts. Overstimulated by the beauty surrounding me, yet no girlfriend or sister. I wanted so badly to explore the feminine half of the world, so alluring. Peeking up dresses was thrilling, but risky. It made sense to me to experience...
    barbarainside barbarainside 51-55, M 1 Response Jan 10, 2015

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    How does a healthy young boy

    who likes playing football or riding his bike with other boys of his age suddenly develop a desire to want to wear girl’s clothing? That’s a question I used to ask myself when I was younger. I grew up as an only child, and despite this, my childhood was very happy. I had...
    lisaneetim lisaneetim 51-55, M 7 Responses Oct 1, 2015

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    When I was a kid, at around Halloween time,

    my older sister took me into her room and shut the door. She sat me down and told me to close my eyes and open my mouth. I complied, thinking she was gonna give me candy. Instead she put red lipstick on me. When she was finished she told me to look in the mirror and when I did I...
    shredhead5 shredhead5 22-25, M 7 Responses Jul 21, 2014

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    For me i was 12. I had a poster of a female pro

    wrestler on my wall wearing a red sun dress. One day i saw the poster and thought it would be sexy if i put on the dress. When i built up the courage to put a dress on i was immediately hooked. I loved how soft everything felt. Ever since then I've always felt more comfortable...
    tgheather tgheather 26-30, T 11 Responses Sep 25, 2015

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    When I was around 9 or 10 my mom has these

    black glossy boots with 2-3inch heels. I was really curious and when I woke up, which was early that morning, I went into my parents bathroom, where the boots were. About halfway through the first boot my dad walked in and just looked at me. He was half asleep and just told me...
    hasadesire hasadesire 13-15, M 1 Response Jan 4

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    another early experience I had

    when I was in grade 9, this girl who was new to the school asked me if I wanted to over to her house and I obviously said yes but liitle did I know her plans where different than mine. she dressed me up in tight jeans bra and makeup and then we had sex. she caught me by surprise...
    Sexygurl221992 Sexygurl221992 22-25, T 11 Responses Jan 2

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    hello!! for me was a far aunt

    who spent her weekends at our house because of her work. i voyeur her everytime i could. one night i was alone and went to her room. there i grab some of her clothes and dressed them. that was the day lima born.
    imlimacd imlimacd 36-40, T 2 Responses Oct 14, 2015

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