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I Was Caught Crossdressing

Personal Stories, Advice, and Support 2,209 People

    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 4 Responses Jul 21

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    hi i'v never posted before

    so here goas. I am 17 and I am a cross dresser. it all started when I was 11. my parents had just got a divorce and my mom was moving out. while she was moving a few things to the other house I decided to go in her dresser and look around (she always his my toys in there) as I...
    Brittanythain Brittanythain 16-17, M 2 Responses Aug 11

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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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    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 2 Responses Jul 21

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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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    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 10 Responses Jul 3, 2013

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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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    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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    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 25 Responses Dec 8, 2011

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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 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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    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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    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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    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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    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 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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    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 3 Responses Jul 23

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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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    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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    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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    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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    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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    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 Aug 6

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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 was having fun on a day off of school

    crossdressing I had a pink bra and a nice thing on and my sisters old prom dress on and my cousin happend to stop by and he thought that it would be hilarious to take a pair of hand cuffs and handcuff me outside of my house to the basketball hook which is right at the beginning...
    Cdkyle Cdkyle 18-21, T 5 Responses Feb 13

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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 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 was caught by my ex babymama

    while she was pregnant with my second daughter her third child in the cellar trying on heels modeling for myself she tripped on me and my friend found out I crossdress to that day he took it better.
    whitwhit86 whitwhit86 26-30, M 1 Response Aug 9

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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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    I love wearing ladies cardigans.

    I used to wear my wifes cardigans when she was out. She found out and luckily she accepts this and now I wear girlie cardigans all the time. I find it a huge 'turn on'.
    cardiganlover cardiganlover 61-65, M 6 days ago

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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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    So my coworker and I got a chance to sit down

    over a cup of coffee. We discussed what I liked to wear, how often, and how far would I be willing to go fully dressed up. It was a nice conversation, and I didn't feel as if she was going to tell anyone else. She did say she was sorry for telling her friend beside her...
    sissymichelle26 sissymichelle26 46-50, T 5 Responses Aug 12

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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 5 Responses Jun 2

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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 14 Responses May 23, 2012

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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 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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    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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    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 was caught by my ex-wife late one night.

    She was pregnant and I was doing most of the housework. One night while washing clothes I felt how nice her nylon nightgown felt. So after that night every time I would wash it I would sneak into the back bathroom and wear it for a while. One night she came looking for me and...
    happilymarriedguy happilymarriedguy 51-55, M 4 Responses Aug 9

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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 3 Responses 1 day ago

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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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    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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    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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    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 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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    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