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I Was Caught Crossdressing

Personal Stories, Advice, and Support 1,758 People

    My Mum And Sister

    My Sister found some of my pantyhose but i was able to say they were my girlfriends and i thought i had gotten away with it. But the next day she must have gone through my laptop and found pictures of what they first thought was a girl (massive compliment to me :P) but realised...
    lucyxcd lucyxcd 18-21, M 10 Responses Apr 3, 2013

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    This is a famous joke.

    Not true, but fun to repeat. Sam walked into the locker room to change into his softball uniform. The guys spotted the bra he was wearing and shouted "What the hell Sam? How long have you been wearing a bra?" Sam replied "Ever since my wife found it under the back seat of...
    Robertredlips Robertredlips 56-60, M Aug 22

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    I have always wanted to get caught

    cross-dressing and be horribly humiliated. This story you are now reading is not true, but I am sharing it as if it was true: Last Friday night I was fantasizing about being caught cross-dressing. Saturday morning I decided a pair of handcuffs would be just the thing so I went...
    Robertredlips Robertredlips 56-60, M 3 Responses Aug 27

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    Hi there! I am a 17 year old sissy cross

    dresser and I have been dressing as a girl since I was little. I was recently found out by my sister. I was home alone at the time and I saw that as an opportunity to dress as a girl. I went into my sister's room and put on a pair of pink panties, bra, pink dress, pink heels...
    ThatSissyBoy ThatSissyBoy 22-25, M 11 Responses Oct 1

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    I started crossdressing in my mother's clothes

    when I was 10 and became addicted to it almost immediately. A few years later, my little sister caught me at it. I became submissive to her in return for her silence. As far as I know she never said anything to anyone about it. Now, many years later, she will not acknowledge it...
    cdchrystal cdchrystal 51-55, M 6 Responses Sep 29

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    Teenage Days

    My older sister and I always got on well together. There was not much of secrets between each other. Whilst growing up I had seen her develop and used to ask the usual questions and she had never shied away from showing me her body. She was older to me by a year and half. It was...
    DilXXX1982 DilXXX1982 31-35, M 8 Responses Aug 9, 2012

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    I started collage again yesterday

    and wore me pretty green panties and a lot of people saw and this guy was cute told me to follow him so i did and we dressed up toghter and i tide him forever and my reacher saw and i dresssed with him to and he banged the **** out of me
    AZCROSSDRESSER AZCROSSDRESSER 18-21, M 5 Responses Aug 29

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    This morning as I was sending my wife off to

    work, I walked out to check the mail, then walked over to the garbage can to throw the junk mail away. As I was standing there, my neighbor walked by. She just said hi. I was dressed in my leopard print kaftan with purple painted toenails. I didn't make eye contact but just...
    Sharon03 Sharon03 56-60 5 Responses Oct 16

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    Caught By Aunt

    I have secret desire of wearing lingerie and pretty girly stuff which I used to do alone. I have a taste of classy lingerie which I developed by observing my Aunt, who has some pretty and cute lingerie which were always in my wish list. How come I know about it? Well whenever I...
    shania0adorable shania0adorable 26-30 9 Responses Dec 24, 2012

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    It was late and I was alone with my mom in the

    house, she was watching tv and eating in her room, so why not? I went over and got out all my clothes and slipped into a nice pair of orange panties, a bra with cute flowers on it, black yoga pants a long vneck and a sweatshirt and went to my bed to text my friends, before I...
    Diamondcdx16 Diamondcdx16 16-17, M 16 Responses Jan 10

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    I was caught by my mum a few months ago.

    I was wearing some of her lingerie black tights and black heels strutting around the house. I didnt hear her come in and i turned around she was just standing there shocked . She asked why i did it and i told her it tuned me on . Eventually she told me not to wear her clothes...
    tomcd95 tomcd95 18-21 7 Responses Aug 29

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    i think on some level i used to set myself up

    to get caught. the first couple of times were truly candid without much thought going into it. after learning the extremes of reactions i decided to put a little research into the process which helped reduce the possibility of bad outcomes. the riskiest was getting caught by...
    trailsonrails trailsonrails 51-55, M 2 Responses Nov 23

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    Talk about embarrassing.

    Wow! This afternoon I was nicely dressed in a tight red sweater over my 38D bra and breast forms, grey skirt and red heels with red lipstick to match my sweater. Just for the heck of it, while I looked so cute I decided to drive around town and if nobody was on the sidewalk...
    Robertredlips Robertredlips 56-60, M 7 Responses Nov 1

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    When I go out dressed

    as a woman I usually go at night because I don't want my neighbors to see me, However several years ago I went on an afternoon shopping trip as I wanted to buy some lingerie. I wore a black business suit with matching skirt and a white blouse. The trip was uneventful until I...
    Stephaniegirl226 Stephaniegirl226 36-40, M 10 Responses Oct 3

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    OMG I sure gave some people something to talk

    about this morning. I was at home after the wife left for work so I slipped on a bra, a skirt and a blouse then I put some lipstick on. I walked around the house doing chores when I remembered I had to go give blood today. So I put on my black microfiber panties, took off the...
    Sharon03 Sharon03 56-60 7 Responses Oct 30

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    Cuffed and detained during the holiday season.

    I wasn't really caught in the act of crossdressing but I was caught with the clothes for crossdressing. I actually had told this story on my old profile but I ended up deleting it along with the story. I was trying to stop crossdressing and figured that if I deleted my profile...
    banannasplitz09 banannasplitz09 22-25, M 3 Responses Jul 31

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    Caught by neighbor today.

    It is very cold here today. As normal I sleep in some sort of lingerie. Last night I fell asleep in my black satin cami and thigh highs. I wasnt thinking to much of it this am. It was around 3 below zero i wanted to run out and start my car so it could warm up as i got ready...
    guyinsatinlingerie guyinsatinlingerie 36-40, M 12 Responses Jan 6

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    Caught Big Time So after being on this social

    site, I was definitely feeling like I had to get into femme. My desires were raging. So I got all dolled up in some clothes that someone on EP had requested to see me in. I had tucked and put all my foundations on and made several clothing changes for the pictures she wanted...
    JessAngel JessAngel 22-25 11 Responses Dec 8, 2013

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    The Lady Down The Street

    That lady whose house I would cut the grass who left her shoes outside. One afternoon I had gotten my hands on a Bikini a few yards down from hers and was wearing it when I went into her yard; she had high bushes which concealed the yard. I was working my way around the edge to...
    francescavera francescavera 56-60, T 11 Responses May 23, 2012

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    My friend came over to my house

    and he went to my room I forgot to put my pink thong away and he asked if I wear it I told him yes and he asked if I fully dressed I once again said yes he told me to dress for him when I was finished he said he would make me feel like a real girl and he definently did about 3...
    Pantyhoseboy1 Pantyhoseboy1 18-21, T 7 Responses Aug 23

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    I swiped my first pair of panties from a

    friends sister when I was 9. By the time I was 11, I had collected quite a few pairs from her and my cousins. I kept them in a shoe box in the back of my closet. I would wash them when my mom was at work. One day I forgot to take them out of the drier before mom got home...
    Bobbie1952 Bobbie1952 61-65, M 4 Responses Aug 7

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    I dress up when I travel

    for work. Sometimes I step out into the hall way, I guess for the thrill of being seen. I've even gone to get ice...nothing. But on my last trip I took another walk down the hall, looked out the window, turned around, walked back my room. Inserted the card...nothing, the...
    Nyssa59 Nyssa59 51-55, T 3 Responses 1 day ago

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    I was caught cross-dressing.

    I sometimes travel to different cities for work. In nice cities (San Francisco) I rent a motorcycle on my days off and ride to the nice places. In SF it was Yosemite Park. Part of my fun is wearing red lipstick behind the windscreen of my helmet. The bad thing happened in...
    Robertredlips Robertredlips 56-60, M 1 Response Aug 27

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    A night out as Rhonda had me visiting a local

    establishment where a band was playing that I follow. I was with a friend, and she is very acceptable of my crossdressing. I was beautifully dressed in a blue blouse and a red skirt and 2" blue pumps. I had just had a facial and had my arms, legs, chest and back waxed. I had...
    SweetRhonda SweetRhonda 51-55, T 5 Responses Apr 8

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    Surprise surprise. ..

    . I had a meeting to attend yesterday in Des Moines IA. It was just in the afternoon so I drove up and back the same day.  I got dressed in my man clothes but put on panties and thigh highs. The plan was to wear a pair of heels to drive to and from the meeting.  I left the...
    cdjo cdjo 41-45, M 15 Responses Apr 15

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    When I was 14 I started crossdressing.

    My Mother and older Sister were gone quite a bit. One day after school I went home and started putting on my sisters clothes. Bra, panties, wig, skirt, sweater and high heels. I was applying lipstick and admiring myself in the mirror. My Mother came home early and walked in on...
    Stephaniegirl226 Stephaniegirl226 36-40, M 9 Responses Sep 13

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    Caught By Brain Integrator

    Yesterday morning I had just about finished my normal "Pegg" chores and was about finished peeling a 5 pound bag of carrots for work tonight when I heard a light knock on the front door. I turned to look and this fellow who had done brain integration on both me and my wife was...
    Pegg Pegg 51-55, M 10 Responses Apr 17, 2012

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    I think we've all been caught a lot more often

    than we realize. We just don't know about it because the other person never said anything. Anyway, something I saw earlier this morning made me remember an incident at the LAX airport. I was waiting for a connecting flight for a trip overseas and of course had me laptop with me...
    AlbertSAT AlbertSAT 66-70, M 7 Responses Nov 22

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    My future sister-in-law stayed with us one

    summer. I would have been about 13 or 14. Once I was home alone and, for some unknown reason, found myself drawn to her room. I went through the chest of drawers and found where she kept her panties. I figured out later they were brief style panties. The nylon material felt...
    Niqqi Niqqi 46-50, M 3 Responses 6 days ago

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    Caught By My Sister

    I was 14 and just started crossdressing. I snuck into my sisters(she was 18) room while i was home alone. My sister was out witu her friends and my parents were at work. I stole some panties a bra a couple of her dance outfits (very colorful with dimonds and sparkles) and a...
    ttttt56789 ttttt56789 22-25, M 6 Responses Jan 4, 2013

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    I once fell asleep (druged) wearing a bra,

    top,panties, skirt, high heals, and panty hoes. And woke up on my stomach with my *** hanging of the side of my bed, my as* hole screaming in pain. with my top and bra around my stomach along with my skirt. Panties and pantyhose ripped off with *** on my face. Only people home...
    Bifun101 Bifun101 18-21, M 5 Responses Aug 4

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    I was at my sisters house at the time

    and I forgot to take off my green with pink dotted thong and she saw it over my jeans waist and she took all my underwear away and said if I want to wear things then that's the only underwear I need she also made me put on one of her outfits before her boyfriend got home and...
    Pantyhoseboy1 Pantyhoseboy1 18-21, T 3 Responses Jul 28

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    By my wife and asked how long have I have been

    wearing her bra and panties?i said since we 1st met b4 we got married and I saw u had tons of sexy panties..she then asked if that's why I always bought her new panties weekly .. About 3 to 6 pairs a week.. Her never kept them just always shared them with out her knowledge till...
    kysatinman kysatinman 41-45, T 7 Responses Dec 31, 2013

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    Caught By My Mother

    I was 16 at the time and had been crossdressing in my mother's clothes since I was 6. I thought I was clever about it, but more on that later. A friend of mine had 3 sisters who were 15, 14 and 12 at that time. I remember we had been out after midnight one saturday night and...
    MelissaStewart MelissaStewart 22-25, M 12 Responses Apr 18, 2013

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    Caught

    When I was 13 I had been crossdressing for 3 years now and was never caught. I started telling a few girls I always talked to about how I crossdress and they told me I should tell my parents but I knew I didn't have the guts to tell them at all. Well one day when my mom left for...
    lime277 lime277 22-25 11 Responses Jul 22, 2012

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    I was home alone my GF was gone

    for the weekend so I took the opportunity to dress. I went and got a sports bra and suntan panty hose I put on a nice dress and some high heels, a pair of knee length boots with 4 inch heels. I stayed like that all day which was Friday. That night I slept in a babydoll nighty...
    pmgurl pmgurl 51-55 5 Responses Aug 16

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    Ooh la la..... ....a very close call

    for a very French maid: 100% True Story: When I was 21 and at university I shared a flat with one male friend. He had no idea that I was a crossdresser. Anyway he had gone away for the weekend....I had done all my prep....legs and body shaved...moisturised....and my chosen...
    chloetrans1117 chloetrans1117 26-30, M 15 Responses Dec 27, 2013

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    I Wasn't Caught, She Alreay Knew

    If you read my first story, you know that I was raised as a girl for the first 51/2 years of my life. My moms sister was only 15 when I was "returned" to being a boy, and she seemed to be angry that I had to change. Even though I had been made to change to a boy, I continued to...
    Ddsmen Ddsmen 31-35, F 8 Responses Sep 29, 2012

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    The last time..? Maybe?

    So it's been a while since my last post (December) and I was thinking about coming out. Well, things took a hold of itself in it's own way and so much has changed for me. Around Christmas time, I decided to was some clothes since I was on break. My mom was on break too...
    elliecarr elliecarr 18-21, T 11 Responses Aug 22

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    I was 16 when she caught me wearing her panties

    and bra. I was in my room dressing up didn't know she came home and caught me she said you look cute let's go buy more
    AZCROSSDRESSER AZCROSSDRESSER 18-21, M 14 Responses Jul 20

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    Yay, i know I've been seen now.

    I had been out to visit a friend. On the way home I stopped and put on my bra, blouse, and skirt. Then I stopped beside a quiet road to check in with EP friends. The wind was blowing hard so I decided to step out of my car to let the wind blow my skirt around. As I did so a...
    Sharon03 Sharon03 56-60 6 Responses Nov 1

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    Caught By Mom

    I Have been a cd since 9.I was never caught until i was 17. Its my first story over here so it may seem boring but anyway.I used to steal my sister bra panties an all that stuff &wore secretly.One day mom dad an my sis went to my aunt's for weekend.I refused coz i had planned...
    katiegorgeouss katiegorgeouss 18-21, M 19 Responses Sep 3, 2012

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    I was caught when I was 14.

    My parents were at work and I had the urge to put on one of my mums dresses and a pair of her knickers. I had been dressing for a year or so in secret and always loved my time alone. I was in the dress and i didn't hear my mum come in the house. She didn't shout I just heard her...
    SissyLisaTG SissyLisaTG 26-30, T 14 Responses Jun 11

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    I thought that I was alone in the building

    and decided it was a good time to try on some new knee boots with a black bra, cami, panties, and nylons. I had accidentally trigger the alarm earlier when entering the building and had already called ATD to get it straightened out. Well, apparently they had already initiated...
    JessicaDale JessicaDale 51-55 2 Responses Sep 13

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    My First Time

    I first started crossdressing when I was thirteen, I was at home by myself because my mom had gone out shopping with her friend Naomi. As I walked past my moms room i saw a pair of black pvc thigh high boots with a 6 inch heel and a platform on the bed. I wasnt sure at first...
    touchmythigh touchmythigh 26-30, T 24 Responses Dec 8, 2011

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    Last night I was wearing my sisters clothes I

    had on her blue bra with matching getting on silky pantyhose black mini skirt pink crop top and 5 icnh pink heels on and I went to the park just to walk around when I got back home I finished my day riding my biggest *****
    Pantyhoseboy1 Pantyhoseboy1 18-21, T 3 Responses Aug 31

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    My Mother In Law Busted Me And More

    Her mother caught me wearing her panties, bra, and a nightgown. Back about the time my first wife found out about my wearing women's clothes, I had a real strange experience with my mother in-law. She had a habit of taking naps in the afternoon between 1pm and 4pm in the nude. On...
    francescavera francescavera 56-60, T 13 Responses May 23, 2012

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    Caught Again.

    I went to the doctors last week, to get some pre-surgery things done. While there, the nurse told me that I needed a tetnes shot. I sat there horrified, and tried to get her to look past he shot, I knew where the shot had to be administered to, my ***! I had been running late...
    kattie2121 kattie2121 51-55, M 13 Responses Jul 3, 2013

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    A long time ago now I lived on my own

    and would dress up all the time I got so used to it and it was perfectly normal for me. One day someone knocked at the door and I went to open it completely forgetting that I was wearing pink tights and a really short black skirt. I opened the door and one of my friends was...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 7 Responses Aug 20

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    I had to get something from the grocery store.

    I was wearing jeans and a t-shirt and decided to wear a pair of sandals with a 5" heel. My jeans sort of covered them, but not very well. I was walking down an aisle and suddenly discovered a friend walking toward me with her husband. When they passed me the girl said "Cute...
    Robertredlips Robertredlips 56-60, M 4 Responses Sep 7

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    I've become rather open to my family

    and friends about my crossdressing. Labor day weekend I was attending a family reunion. I was bent over and my panties were showing, when my one and only male cousin put his hand on my back and said" I think I have those same panties!". After an awkward snicker. We discovered...
    Phxpaulena Phxpaulena 61-65, M 12 Responses Oct 10

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