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I Was Caught Crossdressing

Personal Stories, Advice, and Support 1,676 People

    When I was about 16 I found my Mom's red

    lipstick and decided to put it on, thought I would only leave it on for a few min. I had it on and was doing some things in my room when a friend called and said they were going to get a ball game up and to come on over. I said ok be right there when I rode up on my bike his...
    pmgurl pmgurl 51-55 Jul 9

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    My First Time Out

    One day when my parents and sisters were out I got an incredible urge to dress up. My sister was kind of a ***** so I went into her room and grabbed a thong, sexy mini skirt and fishnets along with a cute bra and top. I did my make up so I look just like my sister exactly like a...
    deboss98 deboss98 41-45, T 5 Responses Apr 20, 2013

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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 8 Responses Dec 24, 2012

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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 12 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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    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 15 Responses May 23, 2012

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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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    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 1 Response Aug 27

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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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    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 9 Responses Oct 10

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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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    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 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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    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 19 Responses Jan 10

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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 25 Responses Dec 8, 2011

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    HOW i told my parents

    and the results if u have not told ur parents and are thinking bout it read this NOW!!!!!!!!!!!!!!!!!!!!!so this is what happened i had written a note and left it in an obvious place, i then waited.(check out other story for more description on the beginning)(skipping part in...
    zoey764 zoey764 18-21, T 10 Responses Jul 19

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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 16 Responses Jul 20

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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 14 Responses May 23, 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...
    LisaTG LisaTG 26-30, T 14 Responses Jun 11

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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 4 Responses Aug 16

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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 9 Responses Apr 17, 2012

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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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    I was 15 and had been wearing panties

    and hose and whatever lingerie I had available to me..my moms or my sisters things for the most part...till I spent one weekend at an aunts house as my parents were attending a wedding and thought it best I stay with my moms sister for the weekend...my aunt was out at a co...
    Girdlesissi Girdlesissi 51-55, M 7 Responses Jan 4

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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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    I missed the mailman

    and needed a letter mailed. So I hopped into my car and drove to the post office. I was wearing a black bra with a oversized tank top and black shorts. It let my bra show real good on the sides, I was planing on just putting the letter in mail box and leaving. But the woman...
    meg1cdforyou meg1cdforyou 61-65, M 4 Responses Jul 13

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    Dress Up With Sister Inlaw

    I split up with my wife last year and was liveing with my bro and sister inlaw 1 day she caught me in her pantie draw she askd me what I was doin. So I had to tell her that I like wearing them so she ask 2 see me in them so I turnd around and said only if u dont say eneything 2...
    pantiesilike pantiesilike 31-35, M 3 Responses Oct 15, 2013

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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 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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    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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    The uncertainty is exciting.

    I will go for drives in a skirt nylons shoes and a blouse with no make up or wig. Then I will go into stores like corner store or a coffee shop or the gas station or a walk through the park etc. One time last summer I came across a check stop that was looking for drunk drivers...
    0hBrandie 0hBrandie 41-45, M 4 Responses Apr 9

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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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    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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    I Told My Bestfriend

    Hey everyone well the other night i decided i was going to come out and say everything to my bestfriend Amber. Her and I have been bestfriends for a year and she is very trustworthy so i thought i would tell her. So i told her i needed to tell her some of my secrets and she...
    AutumnCD AutumnCD 18-21, M 15 Responses Jan 11, 2013

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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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    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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    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 was Caught Crossdressing by my next door

    nebor Guy and Im still doing it to day. I was in my Wifes We are the same size too. Well I was in her 34-C push up Bra, and Bikini Panties. With Her Pink String Cami and Sheer Black Yoga pants. out in by back yard and I seen him and tried to Bend down and not be seen by him he...
    Kellyboy541 Kellyboy541 56-60, F 11 Responses Aug 21

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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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    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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    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 22 Responses Sep 3, 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 6 Responses Aug 23

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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 13 Responses Jul 22, 2012

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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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    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 13 Responses Dec 8, 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 4 Responses Aug 4

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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 10 Responses Jan 6

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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 11 Responses Dec 31, 2013

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    When I was 12 i realised a loved the feel of

    female clothing being a guy myself it was strange I knew my mum would freak if she found my out so in the end i decided to make my own dresses i used my old t shirts and anything i had but one night when i was supposed to be alone i was cross dressing and doing poses around the...
    Crossdresserman Crossdresserman 22-25, M 6 Responses Jul 13

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    My best friend saw the bright blue thong I was

    wearing at his house... He told me to follow him inside we went to his mums room because nobody was home. He made me put on her blue bra, opaque pink tights, very short black skirt, a pink blouse, and her 6 inch heels. He made me walk around his house for a while then we did...
    Pantyhoseboy1 Pantyhoseboy1 18-21, T 5 Responses Jul 27

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    The first time i was caught crossdressing i wad

    16 and wearing high heals, fish net stockings, a short skirt, a small skimpy shirt and makeup on. The worst part is my mom caught me while i was riding my boyfriend and my bestfriend was part way through giving me a facial
    Bifun101 Bifun101 18-21, M 5 Responses Jul 6

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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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    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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