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I Was Caught Crossdressing

Personal Stories, Advice, and Support 2,052 People

    deleted deleted 26-30 1 Response Jun 14

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    The last time I was "caught" my neighbor lady

    who is in her 70's caught a glimpse of my pumps under my jeans while i was walking to the garage. A couple days later she asked if I could trim her hedges in front of her house, I said sure. When I finished she called me into her house. I sat down at the kitchen table and she...
    Brin41 Brin41 46-50, M 6 Responses 1 day ago

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    The one time I was ever caught crossdressing

    was by my grandmother! I was in my sisters room wearing my favorite bra and panties when I heard someone reach the top of the stairs! In panic I ran to my room, my grandmother was there and got to see me in my crossdressing glory! Luckily weeks earlier I told her about my cross...
    MelissaCDr MelissaCDr 18-21, T 4 Responses May 27

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    i was caught by mom but this was not the first

    time i was dressed we move it to a new trailer and i found this pretty dress so i keep it. onne night i felt like wearing it so i took my moms panties and a bra both white and put them all on i felt really horny so i started jacking off my mom walked in she ask what i was doing...
    eddiepeasley eddiepeasley 46-50, M 5 Responses Jun 2

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    this is bad someone found my stash

    and I don't know who it is
    crossdresser1065 crossdresser1065 13-15, M 4 Responses May 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 11 Responses Jul 3, 2013

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    I was just wearing my kaftan this morning

    before I got dressed. I decided to paint my nails purple for fun. I had just finished painting them and was cleaning up the kitchen when our roommate walked in the front door with a friend. There I am-red toenails, purple fingernails and a kaftan when a strange woman walks in...
    Sharon03 Sharon03 61-65 10 Responses Apr 13

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    I think we all want to get caught

    but why do we hide our things if we wanted we could just show our family dressed and say this is who I am can someone help me answer this question
    crossdresser1065 crossdresser1065 13-15, M 4 Responses May 13

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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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    When I was 16 I had been crossdressing

    for like 5 years. I was always worried about my my parents or my sisters catching me. One day in the summer they were all at my little brothers baseball game. So I decided I was going to dress up a bit. I went into my older sisters room, she was 19 and had a lot of sexy things...
    GregNHL1994 GregNHL1994 18-21, M 3 Responses Apr 19

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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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    I was 5 when my mom walked into her room

    while I was trying on her white very lacy , half slip. I felt the half slip fit better that the full slip and it did. She asked what I was doing, I blushed, laughed took off the slip and put it back, she only smiled then left the room. From on, I always went into her Lingerie...
    carolannP carolannP 61-65, M 2 Responses Apr 13

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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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    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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    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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    I was about 8 and I was wearing my 17 year old

    sisters aqua marine string bikini panties. They were so soft!!! My sister saw them peeping out from the top of my shorts. I don't remember getting into to much trouble. I then started to wear my mothers slips and skirts such joy!
    jfem75 jfem75 46-50 Jun 23

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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 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 4 days ago

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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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    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 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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    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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    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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    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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    when I was 13 yrs old I wore my sisters skirt

    and then my sister and mom saw me they then tied me to a chair done my nail paint make up put a wig on my head shaved my legs then wore me panties and bra then skirt and taken me to a shopping mall they buy bra panty skirt saree and all for me ..in the mall I have to go to...
    ramanfemi ramanfemi 18-21, M 2 Responses Apr 28

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    one night when I was 11 it was like any other

    night but I couldn't my sleep. I saw a pair of panties on my sister's bed earlier that day so that night I went into her room and closed the door I found the panties and put them on I loved them! but then my mom came in lucky my shirt was long enough to cover...
    crossdresser1065 crossdresser1065 13-15, M 4 Responses May 9

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    Was caught by boyfriends girl friend wearing

    bra with tanktop panties (thong) and thigh high socks.
    Zap4you Zap4you 46-50, M 4 Responses May 22

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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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    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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    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 4 days ago

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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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    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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    1st time I was caught I was about 22.

    I lived in texas at the time and had a roommate. we worked different jobs and he worked days and I worked nights. He had gone to work and I decided to dress up for the day. Well I was in a little sexy dress with pantyhose and heels cleaning the apt. and he comes in from work. He...
    tammycd7 tammycd7 56-60 3 Responses Jun 14

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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 3 days ago

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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 20 Responses Jun 11, 2014

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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, T 11 Responses Mar 1

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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 31-35, M 14 Responses Dec 27, 2013

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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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    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 13 Responses Jan 11

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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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    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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    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 4 Responses Jun 25

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    I've been caught several times

    but about 5 years ago my daughter caught me. I was fully dressed,wig,makeup the full thing. I live on my own so I was sat in the front watching TV, when I heard a key in the front door, the only other person with a key is my daughter but she lives in London so I wasn't expecting...
    linnyj linnyj 41-45, T 4 Responses Jun 2

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    I was caught by my wife one morning,

    the kids spent the night at grandmas house and I had the day off. The wife left for work in the morning, I got up right away after she left... Put on some hose and a jean mini skirt with my blk 4.5" pumps and went out the back door to have a cigarette. Just about a minute later...
    Brin41 Brin41 46-50, M 2 Responses 1 day ago

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    Fiction. I will continue

    as as blog if it has positive response. It was late evening when I returned home after spending a couple weeks visiting my Dad, stepmom and half sister and went to to my stepmothers sisters wedding. Another story for later. At any rate Mom greeted me and told me to put my...
    angiecan angiecan 51-55, T 27 Responses Apr 27

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    I got off work early today

    and drove home. Once there, I'd changed into my skirt and boots. There I was all dressed (nothing upstairs, just a skirt and boots...sorry gurls) when the garage door opens and my son starts into the house. BTW, he lives on his own. I certainly wasn't expecting him home. I ran...
    shadowplt shadowplt 51-55, M 3 Responses Apr 23

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