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I Started Crossdressing By Wearing My Moms and Sisters Clothin

Personal Stories, Advice, and Support 2,786 People

    Every chance I got I would wear my oldest

    sisters nightie or other clothing from my other sisters. But it started when I was about 5 when I reached for my mothers orange cardigan but was caught.
    comfi comfi
    56-60, M
    3 Responses Jul 22, 2015

    First Time Caught

    The first time I was “caught” was when I was fifteen, shortly after my sophomore year of high school ended. My parents had divorced the previous year. I lived with Dad most of the time, but I would visit Mom on weekends, and stay at her apartment across town. She would take...
    Sferin Sferin
    2 Responses Aug 5, 2013

    First Time Caught II: Ten Years Later

    Ten years later, my mom had remarried and moved to another city 90 minutes away. I was living in the dorms at college. The combination of distance and the fact that mom no longer lived alone had pretty much ended my cding opportunities after my junior year of high school. I...
    Sferin Sferin
    1 Response Aug 6, 2013

    My First Pair of Nylons

    when i was around four or five years i put on a pair of my mothers nylonstockings,the thrill i got from them on my little legs was the best feeling i ever felt.from then on i started to try on her shoes and then i put on her girdle and that was it .i knew that i liked wearing her...
    phylisanne phylisanne
    70+, F
    5 Responses May 13, 2008

    Truth Or Dare

    It all started when i was 13 or 14. i never had a sister but i have a cousin the same age as me. she lives in Houston but stays with us when she is in town. We would always play games together. We loved to play truth or dare. One time when we were playing she dared me to let her...
    brittneybaby02 brittneybaby02
    18-21, M
    9 Responses Jan 8, 2013

    Cousins Clothes

    once I was in charge of looking after my aunties dog when they went on holiday. I was home alone in the house and I went to my cousins bedroom and opened her panty drawer, it was full of panties and thongs all shapes and colours (she was 17 and so was I ) I nearly gave a yelp of...
    Elincd Elincd
    22-25, M
    3 Responses May 10, 2013

    I started by wearing my Mother's Pink Silky

    Knickers at age 7, I loved the feeling of the silk next to my skin although it did nothing to excite my sexual aspects. Once I was 14 wearing Knickers made me erect and excited me sexually and I started w*nking in knickers and loved it.
    timothy1994 timothy1994
    22-25, M
    4 Responses Oct 8, 2015

    I started by wearing my mother's silky slips.

    They were my first love and still make me weak with desire a half century later.
    Lori234 Lori234
    51-55, M
    5 Responses Dec 5, 2014

    Do we really "start" crossdressing?

    Don't we really just follow our natural attraction to the same feminine things that some girls have the freedom and joy to experience. But because we were boys told, we mustn't even consider being pretty or attracted to those things. And if we are then we are crossdressers. I'm...
    JoanieNewHampshire JoanieNewHampshire
    61-65, T
    6 Responses Oct 31, 2014

    It Started With My Sisters Bikini...

    It started when I was around 10 years old, my sis had left her bikini to dry in the bathroom. It was purple with little flowers on it, so naturally my curosity got the best of me. I made some sock boobs and It actually fit my slender body pretty good. I was hooked. Any free...
    sarabeth327 sarabeth327
    26-30, T
    7 Responses Sep 15, 2012

    Sister Catching Me

    I have been secretly wearing my sister 's clothes since my early teens, and have always had the thought of what a thrill it would be to get caught! Well a recent summer saw my parents go away for a couple of weeks on holiday. Me and my sister stayed at home, however she was dog...
    20nik 20nik
    18-21, M
    3 Responses May 7, 2012

    My Sister's Tight Dress

    I got started with crossdressing because I was drawn to how nice my mom's silk slips felt. Then one day, I found this bag of clothes my sister had left behind in the garage. She didn't live with us so that bag was there for quite a while. I would sneak into the garage when no one...
    cddude75 cddude75
    4 Responses Jul 14, 2013

    Getting Started

    I can remember being like 9 and 10 my mom worked so I was home alone often. Mom had sensed that I was having problems with my identity she was so very understanding. She even bought me some panties just said she picked up the wrong package so as to not embarrass. She just put...
    Terriwish Terriwish
    36-40, T
    5 Responses Apr 18, 2013

    i started cd by wearing my moms slip.

    I got attracted towards it bcoz it was flowery and very soft to wear. so i used to be alone at my home during the day. 1st time 1 weared it and went to the balcony and while sitting i slept der for few minutes and the girl in opposite bldg noticed me wearing this. i was scared...
    crank1000 crank1000
    26-30, M
    1 Response Apr 4, 2015

    Wearing Mom's

    I moved back in with Mom in the 90s. She was in her early 70s at the time. I lived with her for about 3 years and often made visits to her apartment regularly after that, often to raid her panty drawer. Given that this was my one last chance I decided to move things along and...
    vf15012 vf15012
    46-50, M
    4 Responses Aug 18, 2013

    I'm not sure how old I was

    but I'm going to guess 10 or 11 my mother would take her soiled girdle off after wearing it and leaving it in the bathroom. I remember trying it on and giving my pp a woody hard enough to hit the door. after one time of wearing a girdle I was hooked and have always wore...
    deleted deleted
    4 Responses Jan 14, 2015

    Why We Started

    This story was inspired by a conversation I heard between my daughter who has a 1 year old boy and a friend of hers who has 3 little boys and is now pregnant with a girl. Her friend is very excited about having a girl, finally! They both agree they love their boys, but having a...
    silkydrawers silkydrawers
    2 Responses Aug 28, 2013

    I was the 4 th child with 3 older sisters I

    went from diapers to my sisters panties, slips, blouses and jeans with a side zipper. I never had boys clothes until I out grew my sisters. After hi school I went to nylon panties and slips! Thanks mom!!
    JohnBoy43 JohnBoy43
    70+, M
    Apr 4, 2016

    Closer to Mummy

    When I first started crossdressing I was about 11 or 12 and I begun with my mummy's panties. My mum had a 9-5 job and didn't get home till around 6 at night so I didn't get to see her very much. So one day I decided to get closer to my mummy. I was home alone during school...
    littlegirlmadison littlegirlmadison
    18-21, M
    7 Responses Aug 22, 2008

    Wearing Mothers Lingerie

    I like most of the stories i have read hear i started out wearing my mothers lingerie and clothing. I was around 8 and the draw of my mothers wardrobe and lingerie draw was starting to get rather unbearable. Before i dared to go into my mothers wardrobe i started to wear her...
    littlereggie1971 littlereggie1971
    41-45, M
    3 Responses Oct 19, 2012

    When I was very young,

    my father wasn't around very much, if at all, so I spent most of my time with my sisters and mother. It just seemed natural to wear what they were wearing. The fact that I wanted to be just like them, wasn't really accepted, so it kept happening in secret. I wonder how...
    lauratdc lauratdc
    46-50, T
    2 Responses Apr 15, 2016

    Once my family apart from my dad

    and brother knew about my cross dressing I got lots of help especially from my sisters,aunt and my mother . I was always wearing girls clothes and had lots of my own. At school people just assumed I was gay so it did not bother me about been seen wearing a dress and I looked...
    deleted deleted
    4 Responses Apr 16, 2016

    How I Got Started

        Well like most of you I got my start at a the ripe age 5 to 6 years old and the main influence I had was. Flip Wilson and my Grandmother see back then Flip Wilson's controversial character was a woman named Geraldine.Some of you might remember that .Well anyhow...
    CarlySmith CarlySmith
    41-45, T
    10 Responses Jul 18, 2008

    I Miss My Sister

    This month, I was informed that my sister was found dead at the age of 50. That was a great shock for me as she was the only other remaining member of my parents' family, the last link with my childhood after my parents are gone and only some distant relatives remain outside my...
    tightsvirus tightsvirus
    46-50, M
    4 Responses Oct 23, 2013

    Roleplay/Chat Wth Mom's Pantyboys

    Anyone like to get off talking about sneaking their Mom's panties and slips as a boy? I'd love to share stories while we are both dressed in Mom's silky underwear. Let's message thru here or email and maybe chat on Yahoo messenger.
    vf15012 vf15012
    46-50, M
    1 Response Oct 19, 2013

    it all started with my mother

    and sisters bras and panties when i was 10 i was playing in my sister room i found her panty drawer and put on her panties i have the whole house to myself i would go to my mom room and put onher bras and wearing her dresses walk around the house dressed as a female i love it...
    deleted deleted
    5 Responses Aug 10, 2014

    I was age 10 when I started wearing my Mother's

    big silky knickers and thought the feeling was sensational, I really liked it but was to young to know about er*ctions, that came later when I was 14 and started wearing my Sister's silky knickers and dresses, nighties etc.
    silkgirl8 silkgirl8
    66-70, M
    3 Responses May 20, 2014

    Why do I remember wearing my first bra ...but can't remember playing as a boy?

    I am only 20, so I am not sure why many of my early memories have faded, particularly those times before I turned 8 when my father was alive.  I don't remember much of playing with other boys, or the first time I rode a bike, or the exact details of playing catch with my dad...
    deleted deleted
    6 Responses Apr 18, 2012

    It started with a sexy pair of my sister's

    panties she left in the bathroom, at first I used them to play with myself.then I got curious and tried them on. They were to tight that's when I got the idea to try on my mom's. while searching through her drawers I found her stash of sexy lingerie. She had all sorts of...
    CrossdressedforSucess CrossdressedforSucess
    36-40, M
    2 Responses Jul 9, 2015

    Sneaking Mom's Panties From The Bathroom

    Age 12-14 You know, the first 6-7 years of my fetish seem downright normal compared to some of the other things I’ve done as an offshoot of my fetish. Starting with puberty at age 12 I went wild. I began wearing Mom's panties for longer periods, under my jeans to tease myself...
    vf15012 vf15012
    46-50, M
    2 Responses Nov 29, 2013

    Like Mommy Like Son

    I was very close to my mummy and she is my inspiration. daddy was never around so i grew up with mummy's influence, i spent my weekends with her instead of playing with the boys, my afternoons. we had a very intimate relationship very affectionate and loving. i started wearing...
    sonialexis sonialexis
    31-35, M
    6 Responses Jun 8, 2012

    I started cross Dressing

    when I was 10 I use to wear my sister clothes and sometimes my mom once I started I couldn't stop I am 56 year old right now I dress female most of the time I don't want to stop I am a woman and always will be I date men and I love it
    deleted deleted
    1 Response Jul 30, 2015

    Fully dressed as a girl with my sister's my

    aunt walked in the house. She sat us down and asked me how often we played dress up so I admitted that I felt more like a girl. She told my mother who was cool and suggested I could dress whenever I wanted except when my father and brother were at home as they were both in the...
    deleted deleted
    6 Responses Jul 24, 2015

    My Clothes Where Fine But My Baby Clothes Where Too Casual..

    I wanted to dress my baby with fine clothes, but everything cost too much My solution is in this new website: I recommand it, fine clothes, great quality, all price up to $19.99 !!!!!
    markberk66 markberk66
    36-40, F
    1 Response Nov 19, 2013
    oblivion1000 oblivion1000
    18-21, T
    3 Responses Aug 17, 2015

    I saw **** at a very young age

    and was pretty jealous of vaginas. I didn't want one, but I wasn't ten years old before i started playing with myself. Living with my mother and sister and having dad out of the picture left me to my own devices. It started with them, and turned into a crazy panty theft thing i...
    isittracey isittracey
    31-35, M
    3 Responses Jan 5, 2014

    After being caught by my aunt

    who told my mother I was fully dressed in my sisters clothes we all sat down and decided I could dress any time when my Father was away which was often. I was teased at school for being femme and once went to a fancy dress disco there dressed like Britany Spears so people were...
    deleted deleted
    13 Responses Sep 13, 2015

    Wearing Mom's

    I am just re-reading some things I typed years ago when I moved back in with Mom. There are all sorts of schemes and plans for wearing lingerie openly in front of her, accounts of doing just that, fantasies involving her lingerie.... Oh my! I was such a naughty pantyboy back then...
    vf15012 vf15012
    46-50, M
    2 Responses Nov 17, 2013

    I started as a pre adolescent,

    an aunt was my "legal guardian", she worked as a barmaid for a" retro bar ",workers attired ala Hugh Hefner-esque Aunt Linda was exceedingly lovely,gypsy like dark features. I became attracted to many of her cloths,fishnets,stilettos,seamed stockings,even her everyday dresses and...
    deleted deleted
    2 Responses Aug 7, 2015

    I Was About 9 Years Old...

    ...when I got into my Mother's panties & stockings drawer. I had been in the drawer before...just looking and taking in the smell...her perfume and nylon smells...! Finally, the satin panties seemed to lift into my hands, cold, slimy, and so erotic. They slithered in my small...
    deleted deleted
    3 Responses Nov 27, 2012

    It All Began With Lipstick

    I can remember when I was young, say 7 or 8 years old, my mother would play around with me and put lipstick on me. Not sure what it was all about, but I enjoyed and often asked her to do it. Probably seeking her attention. It was only natural to see what other feminine stuff was...
    Mustanglisa54 Mustanglisa54
    56-60, M
    1 Response Sep 29, 2012

    Just Like Most Of Us

    I to started by wearing my Moms clothing. My mother was very fashionable and always dressed nicely. I would wear her things when I was alone in the house. At first it was just occasionally slipping on a pair of her panties from the hamper when I was around twelve and just...
    glorialamuse glorialamuse
    9 Responses Jan 31, 2011

    I started by trying on my Mothers used full

    length nylon nighties which she kept in a box in the loo before they were washed. She had two main ones, one blue and one pink. I so enjoyed the feel and the softness of these that I soon progressed to wearing her used panties as well. I would put the clothes on and then tie...
    Scarfbound Scarfbound
    70+, M
    2 Responses May 16, 2015

    Caught Rockin That Dress

    Growing up, I had a fairly normal family life. Mom, dad, older sister and I living in the berbs. I believe I was 12 when I started to put on my sisters clothes. She was a senior in high school who worked after school to afford the finer things in life. In her world that was...
    pantyhose4ever pantyhose4ever
    31-35, M
    1 Response Sep 12, 2013

    I started when my sisters dressed me up fully

    as they said I looked more like a girl than a boy. They got me to ***** and gave me some knickers to put on and Sarah fastened a bra on me. I must have tried on every item of clothes they owned and I loved it. This went on for ages until I was caught by my aunt and she told my...
    deleted deleted
    6 Responses Jul 23, 2015

    Moms Maids Outfit

    I was 20 and had come home for the weekend from college. Mom was going to a Halloween costume party and had chosen to wear a French maids costume. I was so turned on by the costume because I had wanted to wear one for so long. Those outfits are so fem and sexy. On the night of...
    Officestyle Officestyle
    36-40, T
    5 Responses Aug 12, 2013

    The First Time Made Me Tremble

    The first cross-dressing experience that I remember was when I was about 11. I had played sick one day and stayed home from school. For some reason I was drawn to the hose and garters in my mother's drawer. I pulled on the support garter belt and attached the tan hose. The...
    CarieDean CarieDean
    70+, M
    3 Responses Aug 23, 2013

    i love to crossdress it make me feel

    so submissive wwould love to be a sissy maid to someone
    joedoe888 joedoe888
    46-50, T
    3 Responses Aug 22, 2015
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