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I Was Caught Crossdressing

Personal Stories, Advice, and Support 2,059 People

    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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    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'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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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 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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    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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    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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    When i was 15 i finally was home alone

    for once for a decent amount of time so i figured it be a perfect time to dress up. I got completley naked went into my moms closet and browsed through all her clothes. I decided on a red sundress, brown sandals, pink panties, a cowboy hat, and this nice pink purse. I had just...
    Zxxvb Zxxvb 22-25, M 2 Responses May 3

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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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    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 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 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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    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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    mskeaton mskeaton 31-35, F 9 Responses May 18

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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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    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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    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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    deleted deleted 26-30 1 Response Jun 14

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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 5 years old when my Mom caught me wearing

    her red lipstick, and posing in the mirror with a cigarette. She didnt freak out. She just wiped my mouth and told me I was very pretty, too bad I was a boy. She told me to stay out of her things, which of course I didnt. I continued to dabble in her make up. When I was around...
    sillytilly2012 sillytilly2012 51-55, T 5 Responses Apr 8

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    My mother-in-law came round unexpectedly

    and caught me wearing a party frock, stockings and high heels. I had nowhere to hide. She played it really cool and just said she assumed my wife was out and left. I was so embarrassed and had to tell the wife when she got back.
    raggeevets raggeevets 56-60, M 2 Responses 1 day ago

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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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    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 a week ago

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    My first experience was in my first foster home.

    Jodi was 19 I was 10. The room smelled ok, just like her perfume & her with perfume. those of us that started cross dressing know that special overpowering smell that is just heaven that you get lost in while cross dressing. I would would do my "Goldilocks" bit. I would put on...
    chaztrisexualnow chaztrisexualnow 46-50, M 4 Responses May 3

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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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    SEX ED WITH MOTHER- Felt like sharing a story.

    This takes place back in the 80's my dad and mom split up. My mom and me had to move in with my grand mother. After that I with drew from the things I liked to do pretty much go to school and come home and do chores. After a year or so things calmed down but I was so confused...
    AL38DD AL38DD 31-35, M 7 Responses May 4

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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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    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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    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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    Journal Entry No: 20 Bikini Lines I had the

    house to myself today finally. I was up all night the night before knowing I would have all day to finally be myself. I got up early, but my parents were both still home. So I faked that I was still sleeping. I waiting about an hour before they finally left. I got up so...
    crosskimmy crosskimmy 26-30 5 Responses Jun 23

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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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    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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