Post
Experience Project iOS Android Apps | Download EP for your Mobile Device
This experience may contain mature content, as flagged by the community.
Please click away if you do not want to see this content.
To report inappropriate content, please email us.

I Started Crossdressing By Wearing My Moms and Sisters Clothin

Personal Stories, Advice, and Support 2,857 People

    Nylon Flirt At Heart

    I've always, from a young 12 or 13 year old, had secretly been wearing Mommy's and Sister's Taupe Stockings, and full "Big Girl Panties". Those wonderfully stretchy, sheer, envelopes of electricity, held tightly, high on my thighs, with pretty garterbelts under my sister's short...
    Joyce1951 Joyce1951 56-60, T 11 Responses Sep 16, 2010

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 3 Responses Aug 5, 2013

    Your Response

    Cancel

    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 8 Responses Nov 2, 2012

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 3 Responses Aug 23, 2013

    Your Response

    Cancel

    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...
    Nel1966 Nel1966 66-70, T 4 Responses Nov 27, 2012

    Your Response

    Cancel

    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 4 Responses Jul 14, 2013

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 22-25, M Apr 4

    Your Response

    Cancel

    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 31-35, M 3 Responses Jul 9

    Your Response

    Cancel

    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 6 Responses Nov 29, 2013

    Your Response

    Cancel

    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 13 Responses Jul 18, 2008

    Your Response

    Cancel

    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 11 Responses Sep 15, 2012

    Your Response

    Cancel

    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...
    denise51 denise51 61-65, M 5 Responses Jan 14

    Your Response

    Cancel

    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...
    girlynicole girlynicole 36-40, F 7 Responses Jul 23

    Your Response

    Cancel

    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 51-55, M 2 Responses Jul 22

    Your Response

    Cancel

    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 1 Response Sep 12, 2013

    Your Response

    Cancel

    I had a older sister she found me in my mom's,

    black lacy panties, she kept my secret. I thought, one day I discovered some of my sistes panties in my drawer, I told mom She said there yours now, your sister has outgrown them. I knew then she knew, As I got older I purchased my own, when I was about 12 my sister started...
    stoflicken stoflicken 66-70, T 2 Responses Jul 4

    Your Response

    Cancel

    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 66-70, M 2 Responses May 16

    Your Response

    Cancel

    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 6 Responses Aug 18, 2013

    Your Response

    Cancel

    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 36-40, F 1 Response Nov 19, 2013

    Your Response

    Cancel

    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...
    girlynicole girlynicole 36-40, F 4 Responses Jul 24

    Your Response

    Cancel

    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

    Your Response

    Cancel

    ******* 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

    Your Response

    Cancel

    I started by wearing my sisters satin lingerie

    first her panties then moved on to her lingerie
    satinbitch58 satinbitch58 56-60, M 1 Response Jun 9

    Your Response

    Cancel

    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, 2014

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 3 Responses Nov 17, 2013

    Your Response

    Cancel

    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 2 Responses Jul 23, 2012

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 6 Responses Apr 18, 2012

    Your Response

    Cancel

    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 6 Responses Aug 12, 2013

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 4 Responses May 10, 2013

    Your Response

    Cancel

    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
    aliciafox55 aliciafox55 56-60, T 1 Response 2 days ago

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 6 Responses Dec 5, 2014

    Your Response

    Cancel

    I stared wear my moms bra

    and panties that was in the bathroom in the dirty laundry basket try them and like how it felt then started wearing my sisters and over time started buying my own.
    hotlicker68 hotlicker68 56-60, M 7 Responses Jun 9

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 26-30 5 Responses Aug 10, 2014

    Your Response

    Cancel

    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 5 Responses May 20, 2014

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 3 Responses Oct 23, 2013

    Your Response

    Cancel

    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 10 Responses Jan 31, 2011

    Your Response

    Cancel

    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

    Your Response

    Cancel