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I Remember Wearing My Sisters Clothes When I Was A Teenager

Personal Stories, Advice, and Support 778 People

    Sister's Clothes

    I started wearing my sister's clothes at around 13 years old. I was often home from school before everyone else, so I would rummage through her stuff for lacy, frilly panties, hose, bra, blouse, and skirt. Her shoes didn't fit me, but everthing else fit perfectly. My hair was...
    deleted deleted
    26-30
    1 Response Feb 23, 2011

    Merry Xmas

    It all started as a bit of fun. I had been dressing in my sisters clothes on and off for a few years, but when i was 14, well that's when it became a bit more serious. My friend Steve who was 15 came round one day on the Christmas holidays, and as it was a rainy day, we didn't...
    louisetv louisetv
    41-45
    3 Responses Apr 16, 2011

    1978

    For some people the 1970's was the decade that fashion forgot, but for me it was amazing because it was the first time I ventured out as a girl in my sister's clothes. I loved wearing those long flowing skirts with tights and knee high leather platform boots, a frilly blouse or...
    wetrev wetrev
    46-50, M
    2 Responses Apr 24, 2012

    I Could Not Stop...

    I had spent a large part of my pre and early teens dressing up with my Sister in hers and my mum's clothes, and then when caught I was forced by my Mother to wear girls clothes for a while. This led to a number of adventures that I will talk about elsewhere but eventually my...
    SusanMarina SusanMarina
    26-30
    1 Response Jul 12, 2012

    I always got into my sister clothes she hated

    it. Wish now that I would have just got my own clothes and maybe things would have been different.
    olsentrisha olsentrisha
    41-45, T
    1 Response Apr 23, 2014

    Wearing My Sister's Clothes

    The area where I lived had few children and anyone my age happened to be female and if I played with anyone it was always a group of girls all older than I. My parents both worked and were gone all day and I was left in my sister’s care. She and I were the same size and...
    deleted deleted
    26-30
    1 Response Feb 20, 2011

    Started When 11

    I started wearing my sisters underwear when I was 11. She was 15...I did this all through my teen years. I use to get dressed up when I was home alone...and play with my self...it was so wonderful!!
    ppaulllmmm511 ppaulllmmm511
    41-45, M
    1 Response Feb 18, 2011

    Wearing Sisters Clothing

    I was almost caught wearing one of my sisters tight mini skirts when growing up. My sister had lots of these stretchy spandex mini skirts, she would sometimes wear leggings under them or pantyhose, and sometimes just panties. She had them laying on the floor in her room often and...
    pantiescouple pantiescouple
    26-30
    Mar 7, 2013

    Me Two

    yes i was made to wear my sisters school uniform as a kid up to i was 19 teen punshment for wetting the bed.and my dad would cane me in it in frot of my brothers and sisters in the liviroom
    nappi nappi
    46-50, M
    Sep 22, 2011

    First Night Out With The Girls

    By the time I was 15 years old both my sisters had accepted that I wore their clothes and that I would rather be dressed as a girl than a boy. It had been a long road which I will tell the story of sometime. They were 17 and 18 years old, an age when they had already discovered...
    wetrev wetrev
    46-50, M
    1 Response Apr 6, 2012

    First Time In Panties

    The first time I cross dressed I was about 6. I was in a garden shed with a girl the same age'ish across the street. We had locked the door. We then ******** and looked at each other. watched each other pee in a pan. and put each others clothes on. After an hour or so our parents...
    spaceman100 spaceman100
    46-50, M
    Aug 31, 2011

    Part Of My Style Now...

    Rianna, she always had an interesting style of dress. I was fascinated by it. Being cloaked in black clothing, allowing me to sneak through the shadows of night, was so fascinating, and I was good with it, and good in it too. The whole depressed style of dress has been a part...
    troikabeauty troikabeauty
    26-30, F
    1 Response Jul 20, 2013

    Three Things That Helped Make Me A Cross Dresser

    The title is misleading. I am convinced that my being a cross dresser is inherently something that is a part of me and that I would be one not matter what. What I relate are three things that helped develop what I am today. First, there was my sister - three years older, blond...
    deleted deleted
    26-30
    2 Responses Dec 31, 2010

    Younger Sisters

    my sisters are both younger than me, and physically smaller, although when i was about 14 and they were 11 and 12, the size difference was not great. i liked to try on their clothes and then pose in front of the mirror. any of their clothing would do. shorts and t-shirts were...
    deleted deleted
    26-30
    Oct 17, 2012

    My Sister

    My sister was three years younger than me (and still is). She was smaller too in stature.  I remember a n outfit my mom made for her.  It was a sleeveless dress with matching panties.  It was a red and white print pattern. The panties got mixed up in the laundry with some of...
    jml2000 jml2000
    61-65, M
    1 Response Sep 29, 2012

    Aught Caught Fully Dressed Up By My Sisters

    They didn't like for me to dress up. They. Actually got mad at me for doing it but I loved it I still wore them anyways and I kept doing it sexy thongs panties ect then got into their makeup andbeing really feminine
    sofie35 sofie35
    31-35, T
    2 Responses Dec 15, 2012

    Sister

    When i was 8 my sister and her friends made me put on a pair of nylons and walk around in front of them. I remember getting hard and trying to hide under the bed but they pulled me out and made me walk around in front of them as they laughed and giggled bout my lil weiner all...
    wilddog342000 wilddog342000
    36-40
    Feb 11, 2013

    How My Baby Boy Became A Cuckold

    was engaged to a girl in the early 90's, for about 2 years, and I loved her overbearing attitude. She was a virgin, and she had always told me that she will remain a virgin until her wedding night and I agreed but still played the game. It took 9 months for her to even let touch...
    SubCoupleTN SubCoupleTN
    36-40, F
    Feb 9, 2012

    Her 2nd Hand Clothes

    sheryl had me dressed around 4 and mom went along with it cuz it was cheaper i wore sisters used stuff except panties and bras which mom always got us matching sets from childhood thru teen years til i was able to start my own shopping at thrift stores
    sissykrisb sissykrisb
    51-55, T
    Mar 7, 2013

    Sisters Clothes

    I was lucky enough to have two older sisters and they were both cheerleaders. I loved putting on thier uniforms and fantasize about being a High School Cheerleader. I pretended to be a **** while fantasizing about being gang raped by the football team. They took me and had their...
    deleted deleted
    26-30
    1 Response Jun 18, 2012

    I Was So Lucky

    I have both a younger and older sister, and just 3 years between us. I was quite thin as a child so I had no problem fitting into my sisters' clothes. I remember starting off with their panties. One sister even at a young age had this fantastic sexy pair of chiffon like panties...
    deleted deleted
    26-30
    4 Responses May 2, 2011

    5 Sisters

    growing up with 5 sisters i had so many clothes to choose from it was unreal , also combined with trash bags and their nightgowns was incredible and since i would steal the trash bags from the high school made it even better
    plasticwearingtrash plasticwearingtrash
    41-45, M
    Mar 10, 2012

    Guilty Here Too.

    But I usually wore my Mom's clothes. And got caught a couple of times.
    KenzieTS KenzieTS
    46-50, T
    Apr 25, 2011

    Sometimes.......

    Sometimes, whenever I had the chance and was home all alone. I would sneak into my teenage sisters room and try on their pretty, sexy panties and lingerie. I would get so excited and aroused with that lovely, smooth, nylon feeling! I would then tease my boy clitty, and have to be...
    chrisg03 chrisg03
    56-60, M
    11 Responses Jan 15, 2011

    All The Time.

    I used to wear my sisters clothing all the time when I was in my teens and early twenties. I started wearing her dresses and school skirts and blouses when I was home alone. When I was around 15 I ventured out of the house fully dressed in her school uniform and took a long...
    teather teather
    46-50
    8 Responses Dec 20, 2010

    Summer Of '69.....

    I remember getting caught by my Father while trying on a blue and white floral patterned sundress of my older sister's, during the summer of '69 at age 13. Oddly enough my father had little reaction to it in spite of the fact that he was till the day he died a conservatively...
    leachera leachera
    51-55, T
    4 Responses Apr 30, 2011

    Started When I Moved To basement

    I had worn my mom's things a few times: robe, slip, but no panties and only in my room looking at myself in a mirror. When I was 15 I moved into a bedroom in the basement next to the laundry room. Well I soon found myself picking through my sister's stuff: first the panties...
    deleted deleted
    26-30
    2 Responses Jan 22, 2012

    Guilty As Charged ,i Did It !

    I know some of you like a sexy story,well this isn't one , just so you know. I don't want to waste anybodies time. Well it's Connie once again! I started out wearing my mothers and sisters clothes. My mom was old school girdles longline bras and stockings. My sister was...
    deleted deleted
    26-30
    2 Responses Apr 19, 2011

    Like everyone with a sister,

    I too experimented wearing my older sister's clothing. It started with a pair of her panties. It was a purple satiny brief pair with a tiny cute bow in front. I so loved that pair. She had different pairs but that one always caught my attention.I would steal that particular pair...
    deleted deleted
    26-30
    1 Response Sep 27, 2015

    When I Was A Child

     I hated being mistaken for a girl. Sometimes my mother made dresses for my cousin, as I had the same size, used me as a dummy for testing the garments. I felt myself confused and I was ashamed. When I was 12 years old, I discovered that I really envied the...
    Xatu Xatu
    51-55, M
    Aug 26, 2011

    Bra And Panties With My Friends

    I wrote this originally as an anonymous confession, but I have since decided to take ownership of my experience. I have been wearing my mom's, older sister and younger sisters bra's and panties since i was 6 or 7. Over the years I have become limited to what I can wear from them...
    sailorjerry11 sailorjerry11
    22-25, M
    May 25, 2012

    First Time In Panties

    The first time I cross dressed I was about 6. I was in a garden shed with a girl the same age'ish across the street. We had locked the door. We then ******** and looked at each other. watched each other pee in a pan. and put each others clothes on. After an hour or so our...
    spaceman100 spaceman100
    46-50, M
    Aug 31, 2011

    Still Do :)

    Haha, I know this wasn't the point of the group... but I always wear my sisters' clothes! I have two older half-sisters and every so often they will bring a huge bag of old clothes round to my house. One of my sisters is a bit of a compulsive shopper so she'll buy some really...
    LittleMissLucky LittleMissLucky
    18-21, F
    2 Responses Feb 13, 2011

    I Wish.

    I wish I had a sister when I was growing up. If I had had a sister you can bet the bank that I would have been stealing her clothes. I would have had her help me dress and show me how to do everything.
    sherrynpantyhose2k4 sherrynpantyhose2k4
    51-55, T
    Aug 13, 2011

    A particular favourite was her toy nurses

    outfit. I also used to wear her ballroom dance dresses. Ahhhhhh ............memories............
    debbiesucks debbiesucks
    46-50, T
    2 Responses Jan 8, 2014

    First Time

    When I first started crossdressing (13 years old) I wore my mom's clothes but they were a bit loose fitting, my sister is a bit younger so I never thought of wearing my sisters but one day I saw one of her school uniforms hanging in her closet and some pink panties . I knew it...
    mazzz77 mazzz77
    18-21, M
    3 Responses May 23, 2011

    " Sis's Stuff"

    My sister is older than me, but as teenagers we were about the same size, so I was able to wear her clothes. She was small busted, but I didn't care, I still liked to wear her little bras. I often wondered if she knew. I kind of think she did, but never said anything to me !!!
    davis36a davis36a
    61-65
    1 Response Jan 23, 2012
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