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I Was Caught Wearing My Sisters Clothes

cross dressing 825 People

    My Sister And Her Friends Dress Me Up

    About a year after that,my sister wanted to dress me up again.This is the most girly thing i have ever wore.she took me up to her room whil the house was empty and invited a few of her friends around.they were asked if they could bring a few items of clothing to dress me up in...
    deleted deleted 26-30 2 Responses May 15, 2012

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    When my sisters and parents left

    for LA. I was studying for my test. Then I had a feeling to put on my sister Amy's clothes. I put on a satin red thong, black bra and a panty hose. I didn't hear the door open and my mom came in. She didn't say anything about it but she said you look cute she came out of her...
    Hazelnut1234 Hazelnut1234 18-21, T 16 hrs ago

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    Mom And Sister Caught Me In Their Clothes

    i was home alone after school my sister had softball pratice and mom had to work late.  So i decided to go to my sisters room t try on her clothes i mean panties a bra  a skirt blouse high heels panty hoes make up.  Till one day i got all gussied up i must have fell asleep on...
    deleted deleted 26-30 9 Responses Mar 23, 2011

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    Caught

    My name is Zachariah yeatts and this is my storyi started by wearing my sisters high heel boots I loved wearing them then I wondored how do girls jeans feel so I tried them on and felt right the I wondered how I would look in high heels so I put on one of my sisters dresses and I...
    Dresslover100 Dresslover100 26-30 Jul 19, 2013

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    Bobby'S Summer Beach Clothes

    Below is some great clothe for the more conservative sissy or cross dressers. Jenny got this swim suit for me to wear to the beach for spring break and summer too. It has shorts for the bottom and I wear a white see thru cover up over the top. I walked down the beach the other...
    bobbylee111 bobbylee111 36-40, T Mar 14, 2013

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    The Best But Worst Might Ever

    When I was 13 about to turn 14 I made a stupid *** mistake ever. One night during summer I decided to go into the house next store to my because they had a hot *** daughter that lived there. Anyways they had gone outta town for 3 day and there house was mine because they had left...
    Obyea Obyea 51-55, M Feb 25, 2013

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    Surprised After School

    i was never interested in or any good at sports but both of my sisters were excellent athletes. i was often home alone after school while they were playing whatever sport was in season and my mother was still at work. when i was 12 or 13 i quite suddenly got the urge to put on...
    deleted deleted 26-30 1 Response Nov 25, 2012

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    Thought I Was Caught And Still Don't Know!

    I was 19 and home alone from college, while my parents were working and my sisters were in school. Whenever they were gone like this I alway took the opportunity to dress up and be little Lisa Rene for the day. On this particular day, I showered and cleaned up, using my mom's...
    Lisagurlll Lisagurlll 36-40, T 4 Responses Jan 15, 2012

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    Caught Wearing Sisters Clothes

    Me and my sister wear 11 years old when she caught me. My parents had left for the day to go on a date and my sister was at her friend's house. I was sitting watching tv when I decided to go to my room and get my baseball cards, I was so into that back then it would have scared...
    great12345678910 great12345678910 22-25, M 1 Response Jul 11, 2013

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    The Whole Week

    When I was 13 my family went out of town and did not want to go so I stayed home my family was going to be gone for a week and so they called my sister inlaw to watch me she was 16 she always wore sexy bra and panties. The first night I went to find some of her panties. When I...
    Obyea Obyea 51-55, M 2 Responses Jun 29, 2012

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    My Day In My Sisters Clothes

    6 monthes after the last story i was crossdressing at any chance i could.One day my sister asked me to go into her room.I did and laying on the bed was a leopard print teddy,a pair of black panties and a matching bra.She asked me if id like to try them on.I agreed straight away...
    deleted deleted 26-30 6 Responses May 16, 2012

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    Caught Trying On A Skirt By My Sister

    I did cross dressing for a few years now, but never understood how girls wear the stuff. I was curious how girls wore those mini skirts, dresses, blouses, and whatever else. So I figured to try it when nobody was home. So, my mom had to bring my sister to a softball game...
    FishExplosion FishExplosion 18-21, M 18 Responses Oct 21, 2010

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    My Sister Caught Me In Her Pantyhose......Again

    So it was a Saturday normal old saturday my sister had gone out with her friends but I was bored so I stayed in mum and my dad had gone to work so they wouldn't be back for another 5 hours so when I got the idea I went into my sisters room and slid on her pantyhose I wasn't meant...
    Tommycooper Tommycooper 41-45, M 4 Responses Aug 15, 2013

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    Caught In Sister Dress

    When I came home from school and no one was there I would go into my sister room and put on her bras,panties and dress and wear them around the house. One day I came home there was a note on the counter that read she was at the hospital with a friend will be home late and your...
    Ryan1kc Ryan1kc 31-35, M 1 Response Feb 2, 2013

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    Surprised After School - Part 2

    the day after i was caught wearing my sisters' clothes was Saturday. i woke up early, hungry and having to pee, but afraid to get out of bed after the events of the previous day. my bedroom was in the basement and i would have had to go upstairs to pee so i just laid still and...
    deleted deleted 26-30 1 Response Nov 26, 2012

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    My Heart Is Racing

    so i am sitting at the computer looking at ne panties and bras to buy and all of a sudden i get a phone call from a friend saying she is at my apartment and will be up in like two mins and i had to think fast because i am sitting here in heels womens jeans panties bra that is...
    adenbo adenbo 22-25, M 2 Responses Jun 7, 2013

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    I Was Caught By My Best Friend (a Girl).

    I was 15 and my sister was in college. She left about 40% of her stuff here for when she came home. It was right after christmas break for my sister, and My mom and dad went on a cruise. They said that my neighbor, who was my best girl friend, and her mom would check in on me...
    nicknac113 nicknac113 18-21 3 Responses Dec 19, 2010

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    Caught In My Girlfriend's Clothes. Fun Times

    One day, I went to my girlfriend's house and she didn't now I enjoy wearing girl's tights, socks, and various hosiery and clothing items. Before I drove over, she told me she was doing laundry and that she had alot of clothes on the top of her dresser. I didn't think anything of...
    boyloveshosiery18 boyloveshosiery18 18-21, M 1 Response Dec 6, 2012

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    When I Was 15

    I thought i had the house to mysef for a few hours so i decided to raid my sisters wardrobe. i was wearing her white bra and panties black tights and a cream coloured dress. i was sat at her dresser putting some lipstick on when the bedroom door opened and she was stood there...
    vicky71x vicky71x 36-40, T 5 Responses Sep 28, 2009

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    Caught By Her And Her Friend...

    I was about 14 and my older sis came home unexpectdly with her very hot friend, my sis was pretty hot, but her friend had a rock'n body, (reminds me of Mila Kunis only around 5'10"!). Well, long story short, they caught me in her room, in her ballet tights!
    Fluidsoul Fluidsoul 46-50 12 Responses Jun 24, 2012

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    Bobby Caught By Sister

    Bobby was caught several times by his sister and she finally made him dress as a complete girl. She put him in some of her panties and matching bra, nylons and garter belt, then added a long full petticoat slip with a lace hem and then a pretty yellow dress with white polka dots...
    jennylee911 jennylee911 36-40, F Feb 24, 2013

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    My Step Sister Caught Me

    When I was 12 my father remarried and I gained a step sister. After a year or 2 I had to try on her underwear I was very careful just to use dirty stuff from the wash basket at first. Eventually the desire to try on clean bras overcame me and I started to regularly...
    sugerbear sugerbear 61-65, M 14 Responses Nov 14, 2008

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    How It All Began For Me.

    I have been crossdressing since I was 8 years old. It all started innocently enough. I only have one sibling, my sister who is older than I am by two years. My dad passed away before I ever got to know him so my mother raised us alone. Since my mom was the sole bread winner...
    spikeheels69 spikeheels69 51-55, T 3 Responses Nov 12, 2012

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    Busted By Sister

    I think I was 10 or 11 when this happened.  My older sister snuck up from behind me and ran her finger down the middle of my back to surprise me.  She's the one who got the surprise!  I was wearing one of the racer-back sports bras she was donating to goodwill because they...
    SDC92374 SDC92374 51-55, M 15 Responses Feb 3, 2012

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    Haven'T Yet But Want To Lol

    I have this thing that almost every night I go into the bathroom after my sister has a shower and have a **** and *** into her undies she's left in the washing basket. Like I know it's bad lol but I love it! For ages but I've gone in saying to myself I'm gonna do it and leave...
    teencd184u teencd184u 18-21, M 3 Responses May 9, 2013

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    Caught Again 2

    After I was caught by my sister jessy in her clothes.  And was lucky she didn't tell.  I figured I was blessed.  Well a month went by and I had the chance to dress again.  So I went into my mom's room and got some of her heels, bra, pantyhose.  Went into...
    pantyhoseslut pantyhoseslut 22-25, M 11 Responses Oct 10, 2009

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    Sisters Pink Baby Doll Nighie and Panties

    I  was  ten years old,  my sisters would often leave their  dirty cothes in the bathroom.  My older sister had left her pink baby doll nightie with amtching pink "bloomer" panties on the bathoom floor.  I had to try them on,  I ha...
    chicagosissy chicagosissy 51-55 6 Responses Aug 9, 2009

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    Caught By Sister By Kind Of Trying To Be

    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 9 Responses May 1, 2012

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    I Did It

    Omg I did it! I'm still hard lol. I had her bra on and just had the undies on the bed next to me and wanked till I was close and heard her come home which is when I started freaking out lol but just lay there till I heard her coming upstairs and then just as she was getting to...
    teencd184u teencd184u 18-21, M 7 Responses May 15, 2013

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    Both My Mother and My Sister...

    Shortly after beginning to experiment with my sister's clothes, I was caught by both my mother and sister. A girl down the street had a dress for school that was made of some polyester fabric that caught the breeze and moved in ways that boys' clothes simply don't.  When my...
    Joe438 Joe438 41-45, M 7 Responses Aug 23, 2009

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    By Mom

    i waited till everyone had left went into my sisters room and got my faverat bra and pantie set with hose and heels. found a dress she was getting rid of got all dolled up and didnt hear my mom come back she got a good look and freacked
    spaz2692 spaz2692 46-50 8 Responses Sep 3, 2011

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    The Russian

    A few weeks after being caught by my sister.We fell out.We both said some nasty things to each other and we didnt speak to each other for ages.One day she came down the stairs and i was looking at some russian women on the internet.She said to me that since she could tell me to...
    deleted deleted 26-30 May 15, 2012

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    I was wearing her best skirt

    have four sisters, all older. They knew that I used to wear their things from a very early age - five or so. Initially it was knickers which they would spot when I leaned forward and not a great deal was said. A few years later the collectively dressed me in old dress that they...
    Iamsue Iamsue 41-45 2 Responses Feb 19, 2011

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    Caught In The Act

    It seems that many of us started wearing our sisters' clothes when we were around 12-14 years of age, I was no exception, and would try on various items belonging to my two older sisters. At first it was just a pair of knickers and tights but I wanted more than that, I wanted to...
    wetrev wetrev 46-50, M 4 Responses Jul 4, 2012

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    The Sleepover

    The next day,my sister was going to have a sleepover with all of her friends.I thought of this as the perfect opppurtunnity to dress as a girl.That morning,while eating breakfast,i asked my sister if i could talk to her for a few minutes in private.When i was in privacy,i asked...
    deleted deleted 26-30 4 Responses May 17, 2012

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    Caught By My Aunt.

    I remeber getting caught by my aunty in my sis's clothes.  I was up in my sis's room as she wasn't there.  She was just starting college and my mom was gone.  I took some biege pantyhose from my mom's drawer.  I put them on along with my sis's white bra she...
    silkiehosewearer silkiehosewearer 31-35, M 2 Responses Jun 14, 2009

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    I Was Caught Wearing My Sisters Pyjamas

    When i was 13 i was all into wearing girls clothes without my family finding out.One day everyone went out for dinner but i said i wanted mcdonalds for dinner.I was given enough cash to get it and was dropped off at the local resturaunt.I got it and rushed home so i could get...
    deleted deleted 26-30 May 15, 2012

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    Almost Caught!

    I was always prepared when the family left the home to go some place, and I was left home alone. That meant a day of play in my sister's clothing, dresses, panties, swim wear, hosiery and heels. I would stage my own clothing in close by restrooms or bed rooms for a quick change...
    wjk1849 wjk1849 46-50, M 2 Responses Dec 30, 2012

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    Caught Wearing My Siters Clothes

    When I was 10 yrs old my sister knew I liked to wear her dresses and lingerie. She let me wear some of her older dresses and gave me some panties to wear and slips to wear with them. She thot by giving me my own clothes that I would not wear any of hers. I came home from school...
    bobbylee111 bobbylee111 36-40, T 7 Responses Sep 27, 2013

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    My Twin Sister Caught Me Wearing Her Clothes

    Me and my sister wear 11 years old when she caught me. My parents had left for the day to go on a date and my sister was at her friend's house. I was sitting watching tv when I decided to go to my room and get my baseball cards, I was so into that back then it would have scared...
    MrB24 MrB24 18-21, M 3 Responses Nov 25, 2012

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    Caught By My Father

    I was caught by my father when he came home unexpected. When I was growing up I would often dress in my sisters clothes when I was home alone and then I would wander around the house, making my self a cup of tea and sit around pretending to be a girl. This one time I was sitting...
    wetrev wetrev 46-50, M 5 Responses Apr 3, 2012

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    Caught Wearing My Sister's Clothes... In A Very Compromising Position!!

    One day when I came home from school I did my usual. I went to my room and took off my clothes. Then I walked into my sister's room. I grabbed a pair of her silky panties from her drawer and put them on. They felt divine! Then I picked a pair of her sheer to waist suntan...
    1trj 1trj 41-45, M 10 Responses Jul 21, 2011

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    Caught By My Aunt

    I remeber getting caught by my aunty in my sis's clothes. I was up in my sis's room as she wasn't there. She was just starting college and my mom was gone. I took some biege pantyhose from my mom's drawer. I put them on along with my sis's white bra she had in her drawer...
    great12345678910 great12345678910 22-25, M 1 Response Jul 12, 2013

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    Caught In A Dress By My Sister

    I was 13.  My sister was 16.  I had the house to myself - or so I thought.  I took off all my boy clothes and walked down the long hallway into my sister's room.  I got all dressed up in a short yellow dress, panties and a bra. The zipper in back was not...
    karigirl karigirl 26-30, M 13 Responses Oct 23, 2009

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    Caught Again

    After being caught by my older sister kristen who is older than my other older sister jessy.  My sister kristen caught me in her pantyhose.  She didn't say anything but, it scared me good enough to be more caughtious.  I kind of tried to put my hose wearing on hold...
    pantyhoseslut pantyhoseslut 22-25, M 4 Responses Oct 10, 2009

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    Caught By Sister In Law

    True story, I lived with my brother and his wife. one day I went up to the third floor to my sister in laws walk in closet while they were at work, or so I thought. I started looking through all her things, I looked at her heels, then felt all the silky soft lingerie in the...
    flexnmeat flexnmeat 46-50, M 12 Responses Mar 2, 2013

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