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I Started Crossdressing By Wearing My Moms and Sisters Clothin

Personal Stories, Advice, and Support 2,807 People

    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 41-45, M 2 Responses Oct 23, 2013

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    I Got Caught By My Best Friend

    i was dressed up about a year ago im now 18 and he walked in my house i was in my room all dressed up in a corset dress high heeleed boots bra thong and make up he walked in and said i am going to **** you after he saw me and said if i didn't he will tell my mum what i do and...
    georgiexdress georgiexdress 18-21, T 2 Responses Apr 18, 2013

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    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 4 Responses Nov 29, 2013

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    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

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    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 51-55 2 Responses Jul 14, 2013

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    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

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    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 46-50 2 Responses Aug 28, 2013

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    Doing My Chores.......

    I grew up in a house full of women. Four older sisters and a father who worked all the time.(I think he just didn't like my mom and my sisters). My mom was very (for lack of a better word) "controlling" And felt a boy can do his share of household chores. I did the laundry one...
    Tammy59 Tammy59 51-55, T 12 Responses Oct 27, 2012

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    How It Started

    I started wearing my nans mink tights wen i stayed over then i startedwearing other items of clothing like skirts dresses and i found a wig i asked my nan if it was ok for me to wear her clothes and she said it was fine i was bout 7 at the time
    andypantyhoselover andypantyhoselover 31-35, M 1 Response Apr 13, 2013

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    My Aunt Punished Me By Dressing Me In Girls Clothes Once.

      My fem name is Loni and I have been dressing in feminine clothes since 5 or 6. I was at my aunt’s house for the weekend and I was picking on my brother who was a year younger than me. Aunty got mad about the fighting and said that since I was older and was picking on...
    LoniCD LoniCD 46-50 3 Responses Jun 3, 2010

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    Little Boy

    When I was very young my best friend who lived across the street we used to put on our mothers underwear and spend time together never knowing what or why but as time went on it came very important for us to do. His mom came home one day and caught us. She wasn't alone didn't...
    lookiinforluv lookiinforluv 56-60, M 3 Responses May 12, 2013

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    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

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    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 18-21, M 5 Responses May 10, 2013

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    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 8 Responses Aug 12, 2013

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    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 13 Responses Sep 15, 2012

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    I Started Dressing At Age 13 In My Moms Clothes

    When i was 13 my parents worked til 7 and i was left home after school by myself.  i remember riding the bus home and seeing the girls on the bus wearing nylons and wondered what it would fedel like.  i ran off the bus that and up to my moms dresser pulling off my pants as i...
    mcatt81 mcatt81 36-40, M 4 Responses Jan 28, 2012

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    Love the Feeling

    My sister would dress me in her clothes she always thought i was to girlie for a boy she loved to do my makeup and hair then put me in sexy lingerie and cute little dresses,i just loved it and i still do .
    deleted deleted 26-30 10 Responses May 8, 2008

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    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 10 Responses Jan 8, 2013

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    The Magical Black Bag

    I know the title must seem ridiculous, but the huge bag of my sister's old clothing was magical. I found it one day, when I was just being nosey. Curiousity got the better of me, and soon I found my sixteen year old self dressed in silk panties, stockings and suspenders and a...
    mrmagoo2013 mrmagoo2013 31-35, M Feb 28, 2013

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    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: www.tinystylists.com/ I recommand it, fine clothes, great quality, all price up to $19.99 !!!!!
    markberk66 markberk66 31-35, F 1 Response Nov 19, 2013

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    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 11 Responses Jun 8, 2012

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    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

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    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 5 Responses Aug 18, 2013

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    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 26-30, M 3 Responses Jan 5

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    Hey

    I have started crossdressing with my mom clothes.But they are really old now.. I really don't like.
    deleted deleted 26-30 1 Response Aug 14, 2013

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    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 51-55 4 Responses Aug 5, 2013

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    Mom's Pantyhose, Panties, Bra, High Heels...all Worn By Me (Way Too Often)!

      I started crossdressing by wearing my moms and sisters clothing. I began at about age 8. Mom used to hang her pantyhose on the shower curtain rod in the bathroom to dry them. In the evening when I got a bath, I would admire them. One night I decided to put them on. Wow...
    1trj 1trj 41-45, M 11 Responses Oct 8, 2009

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    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 66-70, F 5 Responses May 13, 2008

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    Started In A Family Of All Boys

    My cross-dressing began around 4 years old. I grew up in a large Irish Catholic family of 7 children, 6 of which were boys! I was #6 and my one sister was 12 years older. My parents were wealthy and I rarely saw them. Most of the time we were cared for by a nanny who didnt like...
    genivieveleduc genivieveleduc 46-50, T 5 Responses Nov 2, 2012

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    Pantyhose Rules

    I wore moms hose early. Every day when she was at work. Looking in the mirror dancing. Rubbing my legs then later ******* in them
    steverocco187 steverocco187 41-45, M 1 Response May 20, 2013

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    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

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    My Sisters Stockings

    I can't remember how old I was, maybe 11 it was the early 60's. One day i thought I would have a look in my sisters bedroom and came across a pair of stockings under the cushion of the chair. I took them and hid them in my room to try on later. That night when I went up to bed I...
    cindy1964 cindy1964 41-45, T 3 Responses Apr 21, 2012

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    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...
    AliciaSissy AliciaSissy 51-55, T 5 Responses Aug 10

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    Costume Party

    When I was an early teenager, there was a fancy dress ball in our club for young people. I didn't know in every to change. We decided with mum that I would dress up as the woman. She gave for me one's long flowery dress and the wig. Later she did the making up for me. Examining...
    npcol66 npcol66 46-50, M 4 Responses May 7, 2013

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    How I Started Crossdressing

    I remeber back when i lived at home with my parents i would try my moms and sisters clothes. oh my i had no idea womens and or girls clothing could be so comfortable. 
    marshfieldjman marshfieldjman 31-35, M 11 Responses Feb 25, 2008

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    ******* In Mom's Panties

    I began wearing and ************ in Mom's silky panties when I was 6. I didn't begin *******, of course, until I was around 12 or so and was extremely careful not to *** in them, pulling Mom's panties away at the very last second so I would not stain them. I always put Mom's...
    vf15012 vf15012 46-50, M 4 Responses Jul 20, 2013

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    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 66-70, M 1 Response Aug 23, 2013

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    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 61-65, M 5 Responses May 20

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    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 56-60 11 Responses Jan 31, 2011

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    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 51-55 1 Response Aug 6, 2013

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    Me In My Sisters Prom Dress!

    So a couple of weeks ago I was alone at home for a couple of days... So I went nuts, I recorded alot of crossdressing videos and have been uploading them when ever I get the time and internet is not being used! One of the videos was me in my sisters prom dress!! And yes it felt...
    AmandaJosefine AmandaJosefine 18-21, M 1 Response Aug 14, 2013

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    Im A Femanine Boy Want To Know How I Know

    ever since i was young i always knew my body was diffrent from the other boysthe other boys weighed more and wer more manly but sice i was very young i noticed i had a nice round *** and a tyiny **** plus my body had practically no muscles and i was very skinny witha small...
    ltltlt ltltlt 18-21 5 Responses Jan 10, 2013

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    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 26-30, M 2 Responses Sep 12, 2013

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    Moms Panties

    when i was about 8 i would always take moms panties and try them on. they were all silky feeling and felt nice. i would also wear hers bras i would stuff them with socks and i would just stare at the mirror. later i would put make up on and it would always make me feel great.
    cclaire cclaire 22-25 3 Responses Jul 23, 2012

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    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 9 Responses Aug 22, 2008

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    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

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    My Sister Used To Dress Me Up When We Were Small----

    When i was about 10 I had to wear a pretty ballet dress as I was playing a fairy godmother in a 'gang show' .It was a lovely thing I wish I had it now! I had my first sexual feeling wearing it, Mom also gave a pink frilly pair of knickers they were my sisters,to wear underneath.I...
    ferny121 ferny121 51-55, T 1 Response Aug 2, 2013

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    Vary Young Pantyboy.

    My interest in panties began very young, I think about 5 or 6. I used to have to wear sis's panties which were nylon at age 5 when I didn't have any clean ones. I couldn't believe how smooth and silky they felt. I began to realize that I was having erections at this young age and...
    deleted deleted 26-30 1 Response Jun 3, 2013

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    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...
    kayleew2000 kayleew2000 18-21 7 Responses Apr 18, 2012

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    Ok Kik Me Coolman123456789t

    Ok I stated when I whs in grad 7 I'm going in to grad 10 I'm 15 Ok when I stated I toke my mom cloth and ya the cut out a jean skirt out of my jean then u fond my cut out jeans and sed do u what a skirt a first I sed no then wen't in her room and sed yes on the same day and she...
    coolman2013 coolman2013 16-17, M 1 Response Jul 14, 2013

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    Cuming In Public - I'm Getting More Daring

    I like to dress in womens clothes, high heels , nyolns , bras, etc. Yeah one of those guys, according to my GF... Been doing it for most of my life in various stages and forms. As a guy - I love watching , but nothing beats being there to see a woman / girl working /doing...
    sd4expro sd4expro 46-50 9 Responses Jan 17, 2012

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    Lovely Feeling

    i started by wearing panties. they were silky and white when i rubbed them over my body i got a erection.it felt so good when i put them to my **** and rubbed it felt so good .i came into them. i was hooked after that i wanted to dress in full. so the next time i put on...
    alexa1237 alexa1237 51-55, M 14 Responses Dec 8, 2010

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    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...