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I Was Caught Crossdressing

Personal Stories, Advice, and Support 2,224 People

    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 2 Responses Jul 25

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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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    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 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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    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 younger I would sneak into my

    sisters room and put on her clothes. I loved being a woman. The feeling of the soft tight clothes around my body. Every time I made a new outfit I would set up my camera and have a photo shoot. I loved modeling my outfit and my feminine self. I never once deleted my pictures...
    clevername11 clevername11 18-21, M 4 Responses 6 days ago

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    AGAIN!!! The FedEx man!

    I think he only delivers when I'm home !?!?
    parttimelisa parttimelisa 51-55, M 5 Responses Aug 11

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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 3 Responses Jul 27

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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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    Today! Me and my girlfriend have been dating

    for 3 years and she usually paints my toes (either red or pink). But today, she caught me in her high heels with red toes putting makeup on, she asked if i like to do this, i took the shoes off and walked into the bathroom and was just about to start washing my face when she...
    FootFetiBoy FootFetiBoy 22-25, M 5 Responses Aug 13

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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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    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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    AlexisRuiz AlexisRuiz 18-21, T 1 Response Aug 11

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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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    when a girl dumps you

    and tells you you're weird cause you dress is a ****** feeling.... ??
    Brittanythain Brittanythain 16-17, M 2 Responses Aug 13

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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 26-30, M 12 Responses Apr 18, 2013

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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 3 Responses May 3

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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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    The last time I was caught was actually by a

    cop lol. I was walking around late at night with a rainbow dress on. I was just about home when I saw him pull up. He saw me in my dress and everything lol. I thought about maybe pulling up my dress a bit so he could see my panties, but thought against it lol. Right now I'm...
    pantyboy94 pantyboy94 18-21, M Aug 19

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    A pretty pink fog has descended upon me.

    Lately, I have become obsessed with the feminine wonders of the world. Everything is setting off the triggers in my head. The way a woman walks down the street, An ad on the internet. Her scent as she passes by me. The clicking of her heels on hard ground. The way her...
    crosskimmy crosskimmy 26-30 2 Responses Aug 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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    when I was 16 I went into my ex girlfriend's

    room when she was gone and I stole her panties. when I turned around to leave she was there and saw a pink thong in my pocket. she told me to put it on Or else..... she then started to take pics and showed her friends. but because of this they started giving me clothes at school...
    AlexisRuiz AlexisRuiz 18-21, T 3 Responses Aug 5

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    Yesterday . it was a gokd day

    for m . when ma parents were not present in home . i rushed to ma sis room and .started to wear ma fav clothes . i was enjoyin the moment of the dress on ma soft skin but all of the sudden only ma mom enterd to home and came to ma sis room to take some things . i was there...
    Shakila20 Shakila20 18-21, M 3 Responses 1 day ago

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    Read my past stories

    before this one. The alarm went off and we all woke up. We had to change into our uniforms them leave. When I changed I went to the bathroom, I told them I was shy. And after we all ready we went to arena kinda place where tournament was. When we got there we had to find out...
    CaitlynJennerIsAQueen CaitlynJennerIsAQueen 18-21, M 2 Responses Aug 11

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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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    I mainly underdress, bra

    and panties mostly depending on the time of year. Although summer is harder because of lighter weight shirts people could see the outline of my bra. However today I felt pretty safe due to the pattern of the shirt and type of bra I was wearing. Until a coworker came up and...
    sissymichelle26 sissymichelle26 46-50, T 6 Responses Aug 4

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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 8 Responses May 4

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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 16 Responses Oct 10, 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...
    deleted deleted 26-30 13 Responses Jan 11

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       This is also posted under "I Got

    Myself Into A Self-bondage Experience I Could Not Get Out Of ".  I started dressing in my mothers clothes when I was ten with her leotards and tights. By the time I was fourteen I was wearing all of her clothes, dressing anytime I was home alone and starting to experiment...
    MichelleTiedup MichelleTiedup 56-60, M 3 Responses 4 days ago

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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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    I am compelled to write

    for advanced cds-ing, anyone going out on regular basis in public to shopping malls to buy tank tops to anything girly? The issue I have almost everytime is there are out 10 people when I come in close contact as paying bill, standing face to face in line up, or just someone...
    cross2play cross2play 31-35 4 Responses Jul 26

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    I really want to be caught by somebody.

    .. I don't know who - I just want to be humiliated! I love thinking about being caught by my little sister in her clothes xo
    subladyboy subladyboy 22-25, M 8 Responses 3 days ago

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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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    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 Jul 25

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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 4 Responses Apr 19

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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...
    deleted deleted 26-30 6 Responses Jan 7

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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 18 Responses Apr 15, 2014

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    when I was fourteen (I'm 17) my mom kicked me

    out of the house. I at the time had no friendsa or FAM that could take me in so I had to go live at a youth homeless shelter. (it was nicer than you'd expect) there was only room for 20 people to live there so I was lucky. anyways, whenever somebody new came in, all their...
    Brittanythain Brittanythain 16-17, M Aug 12

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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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    sat in class today and panties were showing

    and the girl asked if those were panties? and I said no but she said yeah they are I have the same pair ??
    AlexisRuiz AlexisRuiz 18-21, T 4 Responses 1 hr ago

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    Story two, after work i ussualy stop at a place

    i know and switch from me to Serenity. And because it was a cloudy mild little bit of rain i know that no one was going to be walking their dogs or walking the paths so i decide that in my pink bra pink panties and bright hot pink polo and strech pocketless jeans where its like...
    Puddles420 Puddles420 22-25, T 4 Responses Aug 2

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    I need to keep my back door shut,

    Neighbor got me again and we struck up conversation about work ect, I was in heels and gown with bra and thong underneath. Ugh neighbors Ugh Apartments
    Averageguy41011 Averageguy41011 41-45, M 3 Responses Aug 8

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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 10 Responses Mar 1

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    I new to hear but here is a kind of caught

    story, i ussualy drive back from work when im alone en femme and its roughly a 9 hour drive so when I do drive alone im dressed completely just no makeup or wig as i try not to attract to much attention while in a company vehicle, roughly half way through i need to stop for fuel...
    Puddles420 Puddles420 22-25, T 2 Responses Aug 2

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    Read my past two stories

    before this so you understand So last week we had our first cheer tournament. I told my sister I was scared someone eventually find out I'm a boy. My sister told me to trust her and just listen to her. So 2 days before the tournament my sister made me a girl. Before she...
    CaitlynJennerIsAQueen CaitlynJennerIsAQueen 18-21, M 2 Responses