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I Was Caught Crossdressing

Personal Stories, Advice, and Support 2,127 People

    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...
    deleted deleted 26-30 13 Responses Jan 11

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    Tonight I took my usual evening walk on the

    city trail system. I've said this many times before, no make-up, wigs, breast forms or anything female above the waist. I was stopped by an elderly couple about half way. The lady looked me up and down and said, "For a young man you look quite pretty." I just stood there and...
    shadowplt shadowplt 51-55, M 4 Responses Jun 28

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    I was always careful

    when crossdressing to not get caught. I was always pretty lucky but not this time. I was home alone one night and just put on some panties and had the urge to wear lipstick. I fell asleep watching TV in bed dressed like that. 6:30 in the morning I was jolted awake by someone...
    strippednakedmale strippednakedmale 41-45, M 8 Responses Jul 9

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    So my parents caught me wearing my sister's

    underwear and got really mad at me and said well if that's what you want to wear then you can ask her if you can wear them. Well I really like wearing hers and don't want to buy my own. Does anyone have any advice on how I can ask her if I can wear her underwear.
    ryan1229 ryan1229 18-21, M 8 Responses Jul 18

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    I am home alone and, of course dressed up.

    Nothing extravagant only a black and white top and black skirt and heels. Just now I looked out the window to see if anyone was around and saw no one. I hopped outside to check the mail and as I did a young lady came along the path. I had missed seeing her coming. She looked at...
    Cherylj1 Cherylj1 66-70, T 3 Responses Jul 14

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    Last Sunday I took a drive to another city with

    the intent of dressing and shopping. Just a little me time. I got to the mall and totally freaked. I chickened out. As I was getting ready to drive home, I stopped at a chad station to get a soda. I was peeved at myself for being a coward and forgot I was dressed. (Just so you...
    shadowplt shadowplt 51-55, M 3 Responses Mar 31

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    I was caught twice the same morning,

    . I went outside dressed to check if garbage man had came. My neighbor also came out to check at the same time, he just said Hi and waved. I went out later and the garbage men were coming, I just said Hi and waited for them. Then put the garbage can away.
    meg1cdforyou meg1cdforyou 66-70, M 1 Response 3 days ago

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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 13 Responses Jan 11, 2013

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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 4 Responses Feb 5

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    What type of dresses do you like to wear

    when ever you wear alone??
    Suhanicrossy Suhanicrossy 22-25, F 13 Responses Jul 10

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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 12 Responses Oct 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 13 Responses Jul 22, 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 18-21, M 16 Responses Jan 10, 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 12 Responses Apr 18, 2013

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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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    She told from today onwards u have to wear

    single strap panties at all times but first you have to be hair free and gave some hair removal creams u have to use it twice a week.in my presence u have to wear only transparent panties and bra. And in our relationship I will be dominant.after our marriage u can wear girly...
    Suhanicrossy Suhanicrossy 22-25, F 8 Responses Jul 6

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    As the new work week started,

    it was time to put Kimberly away for a few hours. As I got up, I looked in the mirror, barely recognizing my male face, I decided to do something entirely out of the ordinary and pretty brazenly. Since my family was out of town, I decided I would wear panties instead of my...
    crosskimmy crosskimmy 26-30 6 Responses Jun 25

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    just right now. I went to my car to grab my

    swimsuit and a few other things and I heard a neighbor with a female voice off in the distance say "look is that a cross dresser?" I was hoping the shaded drive way blocked me from view.
    hankypanty6664 hankypanty6664 31-35, M 2 days ago

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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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    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 11 Responses Feb 5

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    i was caught by the paper lady.

    i don't know her personally. she must have told her husband. he slowed down every time he was on the route after that.i have been a little more careful since then. my wife puts up with my dressing. she doesn't want to see dressed up anymore. so it was kind of exciting.
    sbjj sbjj 51-55, T 3 Responses Jun 28

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    I think I like getting caught

    now when I go out dress up it feels different now because Iam not where I live and no one knows me.
    hotlicker68 hotlicker68 56-60, M 2 Responses Jul 10

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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 11 Responses Jul 3, 2013

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    Black dress, underneath s & s,

    satin panties, my wife walked in, not her shock but mine when she said my dress was better than hers, we have not spoken of it since, but she does like to paint my nails
    deleted deleted 26-30 4 Responses Jul 18

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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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    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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    19 Year old Alex here,

    looking for a mistress to communicate with and obey over email. If anyone is interested please PM me. Thank you!
    alextetra alextetra 18-21 1 Response Jun 29

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    Thinking about it now,

    after all the close calls and 'hiding' of things, deep down I suspect many of us hoped we would be caught. But caught by someone accepting and understanding that might have allowed us to experience that side of ourselves. Without the cruelty and ridicule that too many have dealt...
    Allysoninaz Allysoninaz 46-50 5 Responses Apr 19

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    I think the neighborhood security guard saw me

    in a short jean skirt this morning. He was making his rounds and stopped to watch me for awhile while I was working in my garden
    meg1cdforyou meg1cdforyou 66-70, M 4 Responses 3 days ago

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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...
    57Peggy 57Peggy 56-60, M 10 Responses Apr 17, 2012

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    Mental note. When in bra

    and thong remember to shut back door. Nighbor may stop in and say hi. Trust me very akward.
    Averageguy41011 Averageguy41011 41-45, M 3 Responses Jul 19

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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 17 Responses Oct 10, 2014

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    I was 15 when I was caught by Mr.

    Gunderson, a neighbor who lived down the street. I'd found a summer job and got to stay home alone when everyone else went on vacation. Sixteen days by myself to enjoy dressing during the evenings or at least being able to wear panties and nities to sleep in! Most nights I'd get...
    amandatrane1 amandatrane1 51-55, T 3 Responses Jul 18

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    I was caught today at this guy house I was all

    dress up with everything make-up and my red wig on and his wife came in there bedroom we were going at it what a surprise she was not happy.
    hotlicker68 hotlicker68 56-60, M 4 Responses Jul 10

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    I was with my grandma

    for weekend. I went there wearing my boy clothes and under I wore, garter belt, nylons, thong, girdle and a bra. All my girl clothes u couldn't see. So my grandma was happy I could come since she's been lonely for while. Me and my grandma were watching tv and remote fell off bed...
    CaitlynJennerIsAQueen CaitlynJennerIsAQueen 18-21, M 1 Response Jul 21

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    When ever she stays with me I have to dress in

    a sexy transparent saree without panties underneath it..she goes crazy my seeing me like this and ready to **** me upto her satisfaction
    Suhanicrossy Suhanicrossy 22-25, F 3 Responses Jul 8

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    My family was leaving

    for dinner and I didn't wanna go, right when they left I rushed to my sisters room and I had this all planned out. I put on a thong and sports bra. Put in some bra inserts. Then got her cheerleaders uniform and put it on. I did my makeup. I got my wig and I straightened my wig...
    CaitlynJennerIsAQueen CaitlynJennerIsAQueen 18-21, M 1 Response a week ago

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    Hi guys my 2nd post I think,

    I have a problem, I want to be a girl and wear mini skirts and make up, I want my parents to understand me if I say to them "I want a sex change and move to Turkey and start my life again with nobody knowing who I am. I've not told them I crossdress, this is my dream tho...
    Lucy14CROSSDRSSER Lucy14CROSSDRSSER 13-15, T 2 Responses 6 days ago

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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 10 Responses Sep 13, 2014

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    I was caught once but I didn't care it was two

    girls they look right at me and giggled but that was OK to me.
    hotlicker68 hotlicker68 56-60, M 2 Responses Jul 6

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    I was taking a week off to get moved,

    or so the story went, but really was using the time to enjoy being dressed and meeting some people that I had been chatting with over an adult line. Fully waxed smooth, hair styled and sprayed into place, nails perfectly polished and in very frilly, lacy lingerie I was finishing...
    amandatrane1 amandatrane1 51-55, T 6 Responses Jul 13

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    How are you planning this weekend girls.

    ..I was planning to go for shopping wearing butt length skirts with no panties wearing ..and the whole sunday cleaning the house wearing single strap panty and bra
    Suhanicrossy Suhanicrossy 22-25, F 1 Response 4 days ago

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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...
    deleted deleted 26-30 9 Responses Aug 20, 2014

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    I was 13 and at the weekend my mum

    and sister and brother went out. I stole £10 from my mums purse and went to the drug store. I bought red lipstick and red nail polish. I went home and put on knickers and a dress. Then I painted my toenails red and my nails red. I got a dress and heels and put them on. My mum...
    Sexyrachel1406 Sexyrachel1406 22-25, M 4 Responses Apr 24

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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...
    deleted deleted 26-30 11 Responses Mar 1

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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 17 Responses Apr 15, 2014

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