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I Was Caught Crossdressing

Personal Stories, Advice, and Support 2,564 People

    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...
    EvaMarie1406 EvaMarie1406 22-25, M 6 Responses Apr 24, 2015

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    just been caught by a delivery driver wearing a

    Simon Jersey black dress and apron. The wife thought it was hilarious there she was in jeans, jumper and trainers and the driver saw both of us. Luckily she went to the door. She's gone out now but wants me to do the washing up and the hoovering while she's out and start tea...
    Bower99 Bower99 56-60 2 Responses Jan 27

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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 20 Responses Sep 3, 2012

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    OMG dear diary!! It started one night I got

    home from work.  I worked the late shift that night so I got home pretty late, early morning really.  I was pretty stressed from work and school responsibilities getting to me, so I jumped in the shower and decided I would use my girly shower products.  I love opening the...
    crosskimmy crosskimmy 26-30 1 Response Jan 21

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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, 2015

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    When I was 13, I showed my parents on purpose

    that I was crossdressing. Not all-female, but a mixture with skirt and makeup. They were furious and made me throw away all the clothes I bought, like 200 dollars worth. My mom even asked my dad if I was demon posessed. Ever since them I've hidden it. But, there are 2 times...
    Soundsrealgood Soundsrealgood 22-25, M 7 Responses Dec 28, 2015

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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, 2015

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    I was about 12 years old.

    It was eraly morning I thought my sister had left. I walked into her room and started digging in her pantyhose draw. I didn't even see she was laying on the bed. She jumped up and said what are you doing. I had on just my shirt. I said I was looking for my socks. I don't think...
    Christymariegirl Christymariegirl 51-55, M 1 Response Dec 30, 2015

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    Well, the thing that caught me was a neighbor's

    dog.... I was wearing panties and a sports bra under my normal close to get the mail just now. My first time with some article of female clothing on in public..., walked past two houses and along a road to our mail box in the rain and the only thing to pay me mind was a dog XD...
    darkcuckoo darkcuckoo 18-21, M 4 Responses Nov 10, 2015

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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, 2015

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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 26 Responses Dec 8, 2011

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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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    well 2 years ago for Halloween right

    before a party I had no costume ideas, with my girlfriend knowing im a crossdressing fanatic her and her friend suggested I dress as a classy women. I think in my head perfect! i agreed in a snap of a finger just like any other crossdresser would do. my girlfriends friend sam...
    crossdresserfun crossdresserfun 22-25, T 3 Responses 4 days ago

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    I had been getting dressed every time I was

    home by myself. I always had a day off during the week and my wife worked a normal work week. So there was all dressed up in my favorite skirt and blouse with black pantyhose and knee high boots, when I heard the garage for open. My heart stopped and I ran I to the bathroom to...
    silknrachel silknrachel 31-35, M 4 Responses a week ago

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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 10 Responses Feb 5, 2015

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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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    This is somewhat of a different way of getting

    caught. I buy my cosmetics at my local drug store. It is nice because they have a self checkout line, and for a closet crossdresser like me, it is a fast and discreet way to get my makeups. So a few days ago I went and resupply my cosmetics. Not only did I resupply...
    andreatcial andreatcial 26-30, M 3 Responses Jan 28

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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...
    Suhanihotty Suhanihotty 22-25, F 8 Responses Jul 6, 2015

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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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    AlexisRuiz AlexisRuiz 18-21, T 1 Response Dec 21, 2015

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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, 2015

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    Well, I wasn't really caught

    but almost was close enough. I was in my sister's room when no one was home. I started to parade around in her bra and panties when I heard the front door open and she was running up the steps. I did the only thing I could think of and jumped into her bed and pulled the covers...
    ReneeTalley ReneeTalley 56-60, M 2 Responses 6 days ago

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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 14 Responses Oct 10, 2014

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    Birthday Surprise Dear diary,

    I don't know where to go with this.. just wow... I'm still in shock girls So the other day, my friend (the girl who saw me after my beauty bath) and I met for a cup of tea at a coffee place in the mall.  She wanted to give me my birthday gift.  I met her in the parking lot...
    crosskimmy crosskimmy 26-30 4 Responses Jan 12

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    Not sure if it's crossdressing

    but got caught wearing red nail polish on my toes I was at school and I thought no one would notice but in pe we were doing gymnastics. And I had to take my socks off I had to suck it up and just show it. I still do my toes and now my nails and get them out at school
    EvaMarie1406 EvaMarie1406 22-25, M 1 Response Jan 23

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    It was was the fist day summer break it was

    just me and my mom home .I was in her room dressing up in her clothes i hear her come up so i tried to hid in her closet but it was to late . She came in i was standing there with no where to go and she stopped and said what are you doing wearing my clothes. I just said i like...
    laura1974 laura1974 41-45, T 4 Responses 5 days ago

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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 10 Responses Sep 3, 2015

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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 am going to try and target 3 caught

    crossdressing stories by the weekend Here's story no1 they do come in parts. The bridesmaids story.... Hi my name Eric I am 17 and this is a story of my day as a bridesmaid. It was 9:00am and my sister was getting married I wanted to go in the bridesmaids dressing room and...
    EvaMarie1406 EvaMarie1406 22-25, M 3 Responses 4 days ago

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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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    My wife busted me sneaking in late one night

    still in a mini skirt with makeup on stockings and heels in my hand. I was returning from the adult theater after working 2nd shift and lost track of time. I usually would pull over and remove the makeup and change back into my men's clothes. But that night I was so freaked out...
    chrissyk48 chrissyk48 46-50, M 2 Responses Nov 18, 2015

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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 17 Responses Jan 10, 2014

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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 5 Responses Jan 7, 2015

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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 31-35, T 20 Responses Jun 11, 2014

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    So I actually like to get caught intentionally

    a lot. I'll wear short dresses or skirts that show off my panties or I'll just pull up the skirt a bit. Sometimes I'll walk into a store with a button up shirt on that I'll leave a couple buttons at the top unbuttoned while I have a bra on and I'll sorta flash people. Its really...
    pantyboy94 pantyboy94 18-21, M 4 Responses Dec 13, 2015

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    Well, I just got caught by the wife.

    She had texted me because she figured that I was and said she had to come home to get something, so she did try to warn me. My phone was plugged in on the dresser and I was in the kitchen when she texted, so I had no idea she was coming. I was sitting on the toilet just after...
    57Peggy 57Peggy 56-60, M 11 Responses Dec 1, 2015

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    Well kinda caught. I was at my grandparents

    house for Christmas and my cousins were there and my cousins grace John Nate Hannah and Elise were staying over night like I was but we had to double up and it was John and Nate, Hannah and Elise, which would leave grace and I so we were going to bed and she told me "I'm a very...
    HeidiJohnson HeidiJohnson 18-21, T 2 Responses Dec 29, 2015

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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, T 7 Responses Sep 13, 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 25 Responses Apr 27, 2015

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    When I go out crossdressing I try to look

    attractive yet fit in. Normally I go grocery shopping on Friday's around 5 pm. I noticed many women wearing business suits most likely shopping after work. As a new experience I decided to do my grocery shopping en femme. Even though I can usually pass I try not to talk too...
    Stephaniegirl226 Stephaniegirl226 36-40, T 6 Responses Jan 22

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    I wasn't, hopefully..

    . I just snuck out to take a walk around the block in my new panties and yoga pants. (I'm of adult age so my mother wouldn't care what I do as long as it's not illegal) I should have worn some flats or something but I also had to sneak back in my house... Hopefully someone might...
    MelissaTheSexyCd MelissaTheSexyCd 18-21 4 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 19 Responses Apr 15, 2014

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    Well, I was caught by my best friend today.

    I was wearing my pink with hearts bra today with my girlfriend and he showed up. Idk but somehow I guess he saw my bra strap. I lied and told him it was a bet between me and my girlfriend. Thank god he didn't know I was wearing neon green lace panties xD
    pantyboy94 pantyboy94 18-21, M 3 Responses 1 day ago

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