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I Was Caught Crossdressing

Personal Stories, Advice, and Support 1,878 People

    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 4 Responses Nov 23, 2014

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    I can't remember the first time I did get

    caught coz I think I was around 6 or 7 and it was just dismissed by people as I didn't understand what I was really doing. But earliest time I did get caught that I can remember was this. I must have been around 12-13 and I made sure every time I was alone and had at least 2...
    apwnn apwnn 18-21, T 3 Responses Mar 17, 2014

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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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    Part two So my mum came back with bags full of

    shopping and told me to sit down she said I knew you was dressing up in my stuff I just never caught you and I wasn't going to bring it up because I'm guessing you weren't comfortable with it yet but now I know fill free to dress up anytime where at home and then she gave me the...
    missjazzmin missjazzmin 18-21 7 Responses Feb 5

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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, 2014

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    I just got caught. Really caught by my wife!

    This morning my wife had to go out and I arranged to follow on and meet her in an hour. This was a perfect opportunity to put on some girly clothes. So I went and Put on a pair of tight purple panties, Wolford 10 tights, an old bra, some B cup prosthetic breasts, a red bodycon...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 14 Responses Jan 11

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    After a night of drinking n going home i

    decided 2 dress up. So i snuck in 2 my moms room while she was asleep tryn 2 b quiet as possible without waking her(stealth mode) crawling on my knees n belly 2 not b seen n darkness just in case she woke. Got a few or more pairs of heels that i like. Made it back 2 my room with...
    whitwhit86 whitwhit86 26-30, M 4 Responses Feb 5

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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 18-21, M 15 Responses Jan 10, 2014

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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 9 Responses Aug 20, 2014

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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 10 Responses Dec 24, 2012

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    my wife saw some pics I had on my iphone.

    I had on a beautiful dress, makeup, my favorite black shapewear and a nice brown wig. she just looked at the phone then at me, I was expecting anger or at the least the lets talk about it speech but no all I got was laughter. she will never know the damage she did to on thee...
    Stacy1165 Stacy1165 36-40, M 3 Responses 2 days ago

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    I've been caught several times by my wife.

    She's not really cool with it but does tolerate. I've never dresses with wigs, make-up or anything female from the waist up. I Just like skirts, panties, heels and nylons. She's ok if I'm not dressing around her. Almost got caught by my parents a few months ago. I went to...
    shadowplt shadowplt 51-55, M 1 Response Feb 24

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    I think I was caught

    as week ago n the bathroom on the pot thought i locked the door but found out i didnt. i dont think I pulled my pants up quick enough n my boss probably seen my thong panties he took a second 2 come in but there's a mirror when u come in the door for the toilet I was on funny...
    whitwhit86 whitwhit86 26-30, M Feb 16

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    Me and my girlfriend just moved to a new town

    and she ask me if I would like to go shopping with her so I said yes as I had nothing else to do. When we got to the mall she asked me what female underwear looked the cutest so I said pink ones with little harts on and a bow on top,then she pick up a matching bra. Then she took...
    Manudglh96 Manudglh96 18-21, M 4 Responses Jan 6

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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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    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 56-60, M 10 Responses Apr 17, 2012

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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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    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, 2014

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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 8 Responses Nov 1, 2014

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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 12 Responses Jul 22, 2012

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    I was caught crossdressing today it was my fault

    as i got the courage to try a dress on in the changing rooms of a clothing store the store clerk said" i looked good" i enjoyed the rush i shall be doing this again soon
    LucyJarvis LucyJarvis 22-25, T 1 Response Feb 16

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    Last Super Bowl I made a bet with a girl

    who I was seeing at the time named Mary who was a huge Seahawks fan. We decided that the loser had to wear what the winner decided for 1 hour. Of course Seahawks dominated the Broncos which mean I had to wear what she picked. We found a time when Mary's roomate was gone for the...
    wildcard23 wildcard23 22-25, M 6 Responses Dec 24, 2014

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    I got dared by my sister to dress in her clothes

    so she got me a a bra, thong, wig,high heel shoes and the most beautiful dress also she done my make up and I looked like a fairy tale princess in pink. My mum walked in and my sister said that she always wanted a little sister. The next day my mum told me to dress up again and...
    Manudglh96 Manudglh96 18-21, M 7 Responses Jan 7

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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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    Well today I came to my aunts house

    after my break from collage and she doesn't know I wear panties and others and I forgot to make sure I wasn't showing but I sat on the couch and my pink bra and lime green hipster panties were showing she didn't say anything till I got up she pulled my panties she is single and...
    AZCROSSDRESSER AZCROSSDRESSER 18-21, M 8 Responses Dec 30, 2014

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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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    so my wife already knows I dress,

    and I have been doing it openly with her for a few years now. Well a few nights ago my daughter came downstairs and caught me in my wig and no makeup but didn't know it was me lol. tonight though she came down and I was all done up but she only saw me from the back and said...
    Allyson02 Allyson02 31-35 4 Responses 4 days ago

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    I have been caught twice.

    when I was 12, I used to wear my moms pantyhose, heels and dresses...also makeup and her wig. I hid them in the corner of the bathroom behind the tub. my parents found them. later, when I was 33, I had bought a pair od high heels on ebay. I had been wearing them around the...
    dressupgina dressupgina 41-45, M 2 Responses 5 days ago

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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 61-65 6 Responses Nov 1, 2014

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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 61-65 7 Responses Oct 30, 2014

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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 13 Responses Oct 1, 2014

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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 6 Responses Aug 16, 2014

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    Part 2 After cleaning up I remembered my mate

    said I could where his mum stuff so I went in the shower and had a full shave then went straight to the mum room opened the wardrobes doors and had a filed day I took out the black body con tight mini dress with black stocking with the straps and a pink lace thong and bra...
    missjazzmin missjazzmin 18-21 2 Responses Feb 1

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    I first got caught at my gay best mates party.

    My gay mate had like a 3 day bender party and on the 1st night we had like a one to one talk in the mum room because we was high on drugs and I told him how I crossdress and he told he if you wanted to dress up at his I could do it anytime like wear his mum stuff because his mum...
    missjazzmin missjazzmin 18-21 Feb 1

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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'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 14 Responses Oct 10, 2014

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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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    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, 2014

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    I've been caught twice this is the second time

    I got caught I'm the last of my siblings who is still staying at home so it's just me and my mum. It was on a Friday I never had work so I had the house so night before I did a full body shave so my mum leaves for work and I rushed straight up stairs to my mum room and grabbed...
    missjazzmin missjazzmin 18-21 3 Responses Feb 5

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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 Dec 13, 2014

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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, 2014

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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 7 Responses Jan 4, 2013

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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...
    GirlyLisaTG GirlyLisaTG 26-30, T 19 Responses Jun 11, 2014

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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 4 Responses Dec 17, 2014

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    I owned an office cleaning business

    and working when they were closed and no one around. Sometimes I'd take my girl clothes in and change and clean as a woman but I always kept my change of clothes near. That night I had finished one place dressed and figured as no one was around I'd drive to the next place as I...
    Lyndaloves1957 Lyndaloves1957 56-60, T 13 Responses Nov 6, 2014

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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 13 Responses Apr 18, 2013

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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...