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I Want To Know What Influenced You To Crossdress

What made you say put on the panties ? 1,449 People

    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 7 Responses Mar 9

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    I just wanted to look like

    and be my sister. I thot if I wore her clothes that I would turn into a girl. I soon was hooked on the feel of her silky clothes never to be a boy again.
    bobbylee111 bobbylee111 41-45, T 9 Responses Nov 8, 2014

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    When I Started Dressing

    I was around 8 my first time. My child hood friend and I would spend a lot of time exploring each others parts. One day while playing I found a pair of my sisters panties in the laundry room so I figured I could play the girl and wow to my surprise I never felt anything as...
    pntylvr2003 pntylvr2003 41-45, T 8 Responses Nov 3, 2010

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    Only really did a full cross dressing twice.

    Once on a dare with my friends and once for Halloween.
    pardax pardax 13-15, M 1 Response Jun 6

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    I.was.young a saw a silky pair of leopard print

    VS thong panties on my moms bed. I.wore them and the feel of the silk and.fit.of the thong was what made me continue and eventually devolop in thongs and silk stocking wearing all my.life
    jamiecd85 jamiecd85 22-25, M 2 Responses Mar 29

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    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 2 Responses Oct 12, 2012

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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

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    Even after the first time with my mom's

    pantyhose, I felt like a hole inside was being closed. I had a very abusive father. I am the oldest of 3 and he made me the example. Belittling me in front of my siblings and wouldn't take interest in my activities. The more he was ugly, the more withdrawn I became.
    JamieWH68 JamieWH68 41-45, M 2 Responses Jul 16

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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, M 14 Responses Oct 30, 2013

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    Crossdressing? Is a relative word.

    For me I the meaning chances last year, I was teaching borne male. So growing up I and would wear girls or women's clothing I thought I was crossdressing, But since I have learned I'm transgender, I was and am crossdressing when I am dressed as a male. So I crossdress(as a male...
    DawnR59 DawnR59 56-60, T 5 Responses May 20

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    I lost a bet 3-1/2 years ago,

    for which I had to paint my toes neon pink for a week, show them in public and post public photos on my Face book and dating sites. Prior to that, I was always so embarrassed by my feet that I wore old sneakers to the beach to go in the lake - nobody saw my feet for 10 years! (I...
    steve66oh steve66oh 46-50, M 4 Responses Dec 20, 2014

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    I have no idea but I'll guess.

    I never had a dad. I have five sisters. Zero brothers. I was raised by my mother until she went to prison then I was taken in by my aunt. I bounced all around from my aunt to another aunt to another aunt to my granny to my great granny then finally back to my mom. I've been...
    BoyNbraNpanties BoyNbraNpanties 26-30, M 3 Responses Aug 3

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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 2 Responses Jul 1, 2012

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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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    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 3 Responses Feb 8

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    well I've been found of girls clothes

    since forever so when I tried some on it just felt natural to me and I've been crossdressing ever since
    crossdresser1065 crossdresser1065 13-15, M 1 Response May 12

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    Saw another cross dresser online once

    and after telling my wife about it, I mentioned that I didn't understand the fascination but it did turn me on. She then tossed me some black mesh panties and told me to put them on. I did and we both liked how I looked so she found a few other items for me to wear as well. I...
    free2bme469 free2bme469 46-50, T 8 Responses Jan 6

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    For me was ballet. Mom was a teacher

    and my sister took lessons. My sister and I played in her room. My first item was ballet tights.
    cristyfontana cristyfontana 18-21, T 5 Responses Jun 11

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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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    I'd say that having two sisters was a huge part

    of it because I loved their panties more than my boring underwear. I loved the look, and feel of them and everything about them. A strong second or other major reason is playing around with my best friend and daring me to wear our sisters panties and pretend to be his girl...
    confusedguyhere confusedguyhere 36-40, M 3 Responses Jun 30

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    I've only ever worn ladies underwear.

    I'm straight but I wasn't satisfied with men's underwear so I decided to just try ladies underwear and loved the fabric. It was more comfortable And there are more designs and colors. Plus I was just curious too.
    deleted deleted 26-30 2 Responses Jul 4

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    I just always loved how pretty

    and comfortable dresses looked on the girls, and they seemed to enjoy and have so much fun wearing them. The fabrics were often so soft and silky to the touch also. I wanted to be able to wear such pretty clothes. The idea that dresses were gender specific didn't really occur...
    BabyLee001 BabyLee001 66-70 6 Responses May 20

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    I was influenced after the first time I put on

    a pair of my mom's pantyhose. I knew right then and there, I was missing out on feel and enjoyment of wearing female clothing. It helped that at the same time, I was about the same size as my mom. Woohoo!. Made it very convenient with all of the panties, bras, pantyhose...
    JamieWH68 JamieWH68 41-45, M 4 Responses Jul 16

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    IT'S JUST SO FRCKN CUTE GAAAAAAHHHH also Comfy.

    A bit embarassing though so I don't like telling people. BUT I LOVE LOOKING CUTE OMFG
    jacepierson jacepierson 18-21, M 1 Response May 12

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    feedeeforyou feedeeforyou 18-21, F 2 Responses Jul 17

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    I remember being around 3 years old,

    I would ask my nanny to play "girl". That meant, me wearing my superman cape tied to the waist as a skirt LOL. I would ask my nanny to say "here comes the girl". That is a distant memory and I am pretty sure that my "situation" goes as far back. I was around 5 or maybe 4 the...
    deleted deleted 26-30 1 Response Mar 28

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    For me it was first time I tried on pair of

    pantyhose as a teen. I was hooked what a great feeling soon I found a tight mini skirt at a good will store and a dress and omg what an amazing feeling pantyhose and a tight little skirt !!!!!!
    Brandybondage Brandybondage 36-40 Jul 27

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    I am disabled and when I was young money was

    tight. When I had no clean pyjamas sometimes my Mum put me into one of my sisters. My brother was bigger than me but my sisters were more my size.
    comfi comfi 51-55, M 2 Responses Jul 22

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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 22-25, M 4 Responses Mar 30

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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

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    I've asked myself that very question over the

    years and can come up with nothing. I've always had the interest, from a small boy to adulthood. I dress often and have a supportive wife. :-)
    MnPantyBoy MnPantyBoy 51-55, M 5 Responses Aug 19

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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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    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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    I have asked myself this this question

    so many times, why do I love to CD. Firstly my style of CD is lingerie and pantyhose under male clothing, I dont have the desire to dress fully femm, nor live femm, I am a straight male (no criticism to those who do intended, and although I express my male side in the post I...
    Tambtie Tambtie 46-50, M 9 Responses Feb 22

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    The Girl Next Door. I was five

    or six, the same age as the girl next door. We were in her basement playroom, where there was a closet with her mother's formal gowns. We got them out and pulled them on, enveloping us. There were multiple layers and something just clicked. I still had my pants on, but that...
    Kim1girl Kim1girl 56-60, T 22 Responses Feb 8

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    I did not start until I was 16 years old

    but I realize when I was 8 I would look at the girls and they would were tights and dresses and long heir w/bows in too I was always curious of what it felt like to be dressed in her clothes..that year my mom dressed me up as a girl for Halloween it was great I did not dress...
    Shelly6395 Shelly6395 36-40 3 Responses Aug 19

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    I grew up with 6 women.

    . always panties, bras,stockings,slips every kind of lingerie imaginable was around me. when I wad 12 yrs old something came over me. I guess it was puberty. I put on my moms panties and bra. the feeling wad incredible. . everyday since then ive been dressing.
    pantyboy1488 pantyboy1488 41-45, M 3 Responses Dec 19, 2014

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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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    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 14 Responses Oct 26, 2013

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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 10 Responses Feb 27, 2012

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    My wife lays out panties

    for me to wear daily. I go with it. Usually horny all day.
    casey132 casey132 22-25, M 3 Responses Jul 11

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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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    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 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 14 Responses Feb 21

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    I don't remember what specifically made me want

    to crossdress. I remember it started when I was very young. In fact, I don't have a memory of a time when I didn't do it. I have a very vague memory of hearing about a boy somewhere in our neighborhood that was wearing a dress and I vaguely remember seeing him. I don't know if...
    princessaliciacd princessaliciacd 36-40, M 3 Responses 6 days ago

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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...