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I Was Caught Wearing Girls Clothes

Personal Stories, Advice, and Support 1,599 People

    I Thought Id Share This

    I am sure most of us have been caught wearing girls clothes as i have on numerous occasions the first being when i was 8 by my mother who freaked out and told me little boys dont wear heels. Anyway i thought i would tell you about the time i was caught by a friends wife. It was...
    louisetv louisetv 41-45 15 Responses Mar 5, 2009

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    Caught Wearing Stockings And A Skirt

    I used to go to my best friends house and always wore my stockings we were sat in his lounge drinking and after a while I had to go to the loo so I went out in the hallway just wearing my stockings and high heels and went to the loo. I played with myself while I was in there and...
    lucy1000 lucy1000 56-60, M 4 Responses Sep 11, 2012

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    Sisters Catches Me Dressed

    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 35 Responses May 9, 2012

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    Caught With Mom's Panty Girdle

    I remember I had a train set in the basement.  It was right next to the washer & dryer.  I somehow found my mom's lace panties and pantygirdles there.  I must have been excited by the feminine site, so I put them on.  OMG - how soft and lovely, they were...
    girlydreams girlydreams 46-50 5 Responses Jun 22, 2009

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    Mom Figured It Out

    I was10 years old and I was a shy kid did'nt have many friends so me and my mom spent alot of time together.My dad was always out of town working and my brother was older then me and already moved out.It was the mid 80's and my mom had a few clothing catalogs and one day I was...
    AL38DD AL38DD 31-35, M 4 Responses Feb 24, 2012

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    Everyday

    Well, I could be caught every day, if the guys in the gym locker room were paying attention that is. I am a confirmed panty wearer. I prefer Vanity Fair Body Caress Hi-Cut panties. I have several colors, from boring beige and black to magenta, bright red and leopard print. I...
    TBurke99 TBurke99 51-55, M 2 Responses Jun 12, 2012

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    HOW IT STARTED--When I was around 6

    or 7 my dad split and left my mom in bad shape. After a while mom and me had to move in with moms aunt sherry. Sherry was a classy lady she owned a beauty salon and told my mom she would teach her and give her a job there. By the time I was 12 and being around women dressing and...
    samanth38 samanth38 36-40 Oct 28

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    I was at my sisters room trying on her dress

    and skirt when she walked in and said hi sis. I said dont tell anyone. She said on one condition let me and my friends dress u up andu have to hang with us wearing those clothes sometimes
    dalonelyone dalonelyone 22-25 4 Responses Jun 30

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    Oops Payback

    I was about 6 or 7 when my mom saw me putting on peds (nylon socks) and said I looked cute. So I didn't think any thing about it until my dad saw me in them. Then commented if he sees me wearing them again he would dress me like a girl from head to toe and even my hair, and go to...
    boomer58 boomer58 46-50 7 Responses Jan 20, 2013

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    I Caught Wearing Girls Clothes.

    When i was a boy 10 years old i started wearing girls clothes then in my bedroom my brother seen my in a dress, wig, patyhose, and high heels i was so excited to try dresses, panties, pantyhose they fit me perfectly so i hesitated to take them off so i continued to wear them i...
    Princess1137 Princess1137 61-65 1 Response Jan 18, 2013

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    Almost!

    I was alone at home dressing up, when i was putting up my make-up.. i heared the door bell ring, and knocking on the window next to my door, i checked really quick, it was my grandmother who was standing there looking to see anyone in the house, she didnt see anything so she...
    GirlyBoyy GirlyBoyy 18-21, F Nov 24, 2012

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    I Let Aunt Patty Know

    I was 13 and my mom got a job working 3rd shift on the weekends. I was not happy about it because I knew I could'nt dress up and spend time with my mom anymore. My mom had a half sister and her name was patty. She was younger and more out going then my mom and she was'nt thrilled...
    AL38DD AL38DD 31-35, M 3 Responses Mar 2, 2012

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    Getting Caught

    I was caught a few times growing up and it was so embarrassing. I can remember being caught by my mother and dragged out in front of my parents friends and laughed at. At the time I hated being caught, but afterwards these were my best memories. I always wished that I would be...
    Karentg Karentg 46-50, M 5 Responses Aug 12, 2012

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    The Mail Lady

    When I was 13 I had gone out on halloween as a girl. My mother and girlfriend Cheryl had bought me several dresses to wear. I had alot of fun dressingup and being one of the girls with my mother and Cheryl. It became a routine for me, not on a daily basis. One day in the spring I...
    RobinLeade RobinLeade 22-25 5 Responses Aug 19, 2011

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    The Land Lady And Me

    I was in my 20’s and living with an older woman as a lodger. She was a nurse with a two bedroom flat and I had the tiny “box” room. When she was away for weekends etc it was great as I had the run of the place and it was the first time that I didn’t have...
    SusanMarina SusanMarina 26-30 10 Responses Feb 13, 2010

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    Caught By Mom's Friends

    This is a hard story to tell never shared it with anyone!! I was about 13yrs old. My mom had a couple of her friends over. I went to my room to "play" always dressed from head to toe! To be safe I closed my bedroom door tight. The first time I had done that. My hair was long so...
    christypvcsissy christypvcsissy 36-40, T 11 Responses Mar 28, 2011

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    Caught By Czn And Pay F0r It !!

    when i was 13 i was n0t get permission from my mother to crossdress fully i used t0 dress secretly.. one day my mother and sisters were not at home they g0 for shopping and i was alone at home my mother said to my czn to look after me that she was g0ing... it was great chance f...
    lesban lesban 18-21, M 2 Responses Oct 2, 2012

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    Caught..

    I remeber i was 12 years old and had put on the tights of my momwhen she wasnt home, so i felt so great that i went to her closet again and put on a mini skirt and a bra and her blouse, i felt soo amazing.. but an half an hour later my mom came home, i started to hide cus i was...
    GirlyBoyy GirlyBoyy 18-21, F 1 Response Nov 23, 2012

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    Holiday Dressing

    I was caught by my next door neighbor while putting on my stepmoms wedding dress. I was 14 and spending the summer with my dad and step mom when she came over to check on me while my parents were working (per my parents request) , I never heard her...
    MarciasX MarciasX 36-40 9 Responses Jul 5, 2009

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    Uh Oh

    One day when I was 16 my parents left home to go drop my sister off at college in Georgia. I saw this as the perfect opportunity to crossdress since the baby sitter only came a few times a day. So the minute they left I went to my stash of my sisters clothes I put on a sexy black...
    Loverb0y Loverb0y 22-25, M Nov 20, 2012

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    Caught By My Friends Sister And Her Friends

    I started crossdressing when i was little and loved it from the start. The rush of the frilly dresses and makeup and everything just always felt so right to me. One day i was at my friends house and was spending the night. He went to sleep and as his sister was out with friends...
    girlyboy9710 girlyboy9710 18-21, M 16 Responses Jun 6, 2012

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    Walmart.

    My wife and I just returned from Walmart where the sales girl noticed my pantyhose, thong and then my bra. My wife was in the grocery department, while I was shopping in the women's wear department. I had just come out of the bath room and my outer shirt was caught up, it wasn...
    sherrynpantyhose2k4 sherrynpantyhose2k4 51-55, T 29 Responses Aug 10, 2011

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    Birthday Supprise

    It was my birthday and i only had to work half a day. my wife new that i would be be home around noon. when i got home my wife met me at the door and told me to shower and shave as she had supprise for me. i took my shower and shaved my entire body. when i got out she had some...
    DeeDee1966 DeeDee1966 41-45, T 19 Responses Nov 14, 2009

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    Caught In The Woods

    I was caught when I was out in the woods by my house when I was 15. I went back there wearing a pair of pantyhose under a pair of tight silky pink running shorts. I also had on a pink spaghetti strap tank top on with a bra underneth the shirt with two nerf like baseballs to fill...
    der12333 der12333 36-40, M 25 Responses Aug 6, 2010

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    I returned some pajama bottoms

    that were too big to Walmart. No problem at the service desk so I went and got a smaller size of really cute Capri bottoms. When I went to pay fort other items I had to explain that the bottoms were an exchange and I also showed her the receipt. She smiled and told me she had...
    LibbyLee LibbyLee 56-60, T 2 Responses Sep 3

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    Caught

    i was in Junior high school (13 years old) and was home after school alone. It was a spring day, so i ******** down and was running around the house naked with a huge hard on. Back then, I was probably 5'6" and weighed 110 pounds. i found myself up in my mom's bureau...
    Slimbidude Slimbidude 46-50, M 3 Responses Apr 22, 2013

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    Caught Again

    It was a nice pleasant evening so I went up the hill in my car and as it was quite dark I picked up Ken and we went for a drive up the hill.I was just wearing stockings heels suspender belt bra with a mini skirt and no knickers as I like to feel the ***** running down my legs...
    lucy1000 lucy1000 56-60, M 12 Responses Oct 30, 2012

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    Mom Caught Me In Her Bra And Panties

    When I was about 7 years old, I became fascinated by my mom’s sexy underwear. While she was doing chores or getting ready to go out or to work she often wore just a robe over her bra and panties and sometimes when it was warm in the house just her bra and panties all around the...
    barbarascampbell barbarascampbell 41-45, T 7 Responses Jun 11, 2011

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    My Sisters School Uniform

     i was about 9 and i thought my sisters uniform was the hottest thing i had ever seen i had been borrowing her panties from time to time but i could not let go of the thought of wearing her uniform. finally my chance arrived my mum had to go away for four days and would not...
    jarviscooper jarviscooper 36-40, M 24 Responses May 9, 2009

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    High Heels and Hot Pants

    It happened when I was still living at my parents. They went away for the weekend so I dressed myself up. on the saturday morning I came down stairs wearing my high heeled knee high boots, hot pants and tight strappy top. To my suprise when I opened the bathroom door there was my...
    Heellover Heellover 36-40, M 9 Responses Aug 3, 2009

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    Caught By My Neighbor Part 2

    She then walked up behind me and reached around the front of the dress and grabbed the bulge that my **** was making in the front my dress and said that we would have to get rid of that somehow if you where to really look like a woman. She then brought me over and sat me on the...
    allwrappedupinit allwrappedupinit 51-55, M 15 Responses May 2, 2011

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    Caught In Terror

    I will start out telling that this is a true story, happened yesterday morning. It was about 9am and I was still in my sleepwear lounging around without a care in the world. I was wearing a nice but conservative floor length chocolate brown nite gown ,white bra and honey color...
    squeekers2 squeekers2 56-60, M Apr 30, 2013

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    First Few Times

    1st time caught , I wasn't dressed. My parents found my stash hidden in my closet. After they blew up, they took everything and locked it in their closet till I moved out on my own. They never really accepted that part of me and it was never mentioned. 2nd time I was dressed...
    ve5wil ve5wil 36-40, M 1 Response Oct 9, 2013

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    Caught By Mom

    One day when everyone was gone I went into my moms room and put on her bra and thong. Then I went into my sisters room and put on her yoga pants. Right when I was taking them off my mom walked in. She asked what I was doing and I just said I like wearing girl clothes. She then...
    deleted deleted 26-30 7 Responses Oct 20, 2012

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    Caught, But Not Caught

    My wife was at her parents last week, so I went for it big style. I thought I had cleared up all evidence but she found a thong in the bed sheets and a necklace down the sofa. She didn't scream or shout at me. She was perfectly calm, when she asked me "have I had a ***** in while...
    Heellover Heellover 36-40, M 3 Responses Aug 6, 2012

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    Caught Wearing Girl'S Clothes

    I was dressed in girls clothes and went shopping at J C Penneys. I don't pass but I was having too much fun. I walked by the intimate apparel department and decided I wanted a bra fit. I asked one of the sales associates and she agreeded. She was fitting a young teenage girl...
    jml2000 jml2000 56-60, M 6 Responses May 16, 2013

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    Laid By The Carpet layers

    I have just moved into a new house and things are pretty chaotic at the moment with boxes everywhere as we wait for various tradesmen to deliver and/or install all kinds of stuff. The result of this has meant that I haven't had the chance to dress in my wife's lingerie for ages...
    fardon fardon 46-50 Jul 19, 2012

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    By My Friends Wife

    She always suspected that i fancied her husband and that he was bi as well but nothing prepared her for this. We had been seeing each other for a while and i had told him i liked to be girlie. He loved it when i dressed up for him and sucked his big ****. This time as just a...
    vicky71x vicky71x 36-40, T 8 Responses Sep 29, 2009

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    Caught By My Neighbor Part 1

    Before I left my Moms house to live on my own I used to watch our neighbors house for them when they went away on vacation. My Mom would send me over to the house to make sure that everything was alright inside, and that the heat was on, and so fourth. One day as my Mom was going...
    allwrappedupinit allwrappedupinit 51-55, M 11 Responses May 2, 2011

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    Cristina's Sissy-*****

    My step sisster had tons of clothes laying around her room, and me I just loving stealing some and sleeping in them. I love wearing her tight panties all the time. She wasn't dumb though she knew for days that I've been taking her clothes because they were always misplace and she...
    girlydimpale girlydimpale 18-21, M 13 Responses Aug 18, 2012

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    She Finally Caught Me.

    During this time was when I was getting alot of my cding done.  As my mom was spending alot of time with her new boyfriend.  So I got alot of dressing time in.  Which was nice as I was going next door to our neighbors every now and then and having my fem fantasys...
    pantyhoseslut pantyhoseslut 22-25, M 48 Responses Nov 29, 2009

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    Petticoated Paradise Lost

    After all the close calls growing up, wearing a half slip in bed and mom wanting to pull the covers down, and so forth, I finally was caught. And it really wasn't my fault., as you will see. I was traveling on business in Durham, North Carolina and had some down time, so I went...
    Kim1girl Kim1girl 56-60, T 25 Responses Mar 10, 2013

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    My Cousins Outfits

    ever since i can remember i've always liked to wear girls clothes. one day when i was 15, i was at my aunts house to help do some chores and the family left to go to the county fair. i said i didn't want to go and wanted to finish what i was doing. that was fine with them so they...
    valtv valtv 22-25, T 5 Responses May 21, 2009

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    Asked To Baby Sit For Neighbour

    I was 17 and my neighbour wanted to go out with the girls. She was a single mum of one so I said I would do it for her. My neighbour was really fit she was 6th tall slim build very good looking for 32. Her kid was put to bed before I got there I knocked on the door and was...
    Reddevils56 Reddevils56 31-35, M 3 Responses Jun 12, 2012

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    Caught Wearing Thong

    I've been wearing womens underwear for about 7 years and I'm straight, I just think their comfyer than boxers One my best friends of my best friends knew I wore girls underwear and we where sitting in her living room one day talking. I was lying on the floor and she was sitting...
    Luisgarcia10 Luisgarcia10 18-21, M Jul 16, 2012

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    My Two Step Sisters.

    They love dressing me up and playing with me, their both really sexy. The only time I get to see them naked is when their wearing stapons ready to play with me lol.
    girlydimpale girlydimpale 18-21, M 4 Responses Sep 30, 2012

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    Nails

    I wasnt caught wear clothes but one day wen i was younger, I was just painting my nail. I really love to paint my toes mostly because only I can have them painted in public without anyone seeing. Well any way i was just doing my normal routine waiting until my family went to...
    Dyboy44 Dyboy44 26-30, M Sep 11, 2013

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    It was a day where no one was home

    but me. My mom dad and sister were all away. My cousin at work. I decided that I had to go try on some girl clothes I went into my cousins room picked out a pair of panties and a skirt then went to my sisters room to change. After changing it was one of the best feelings ever...
    Kens214 Kens214 31-35, M 1 Response Jul 15

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    First Time Caught

    I started wearing panties at a very young age, my mother neither approved or disapproved, however panties always seemed to find their way into my drawers.  I also learned ************ very young, although I had no idea what is all about, just that it felt really good. I had...
    billiepa billiepa 51-55, M 15 Responses Jun 20, 2010

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    Panties = Penis

    It all started at school I was wearing panties and little did I know we were going swimming today and I had to change with another boy, when we got there we were sent to the changing rooms and I was so scared of what was going to happen we got in the changing room and the other...
    jamiecarter jamiecarter 18-21 Sep 23, 2012

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