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I Was Caught Crossdressing

Personal Stories, Advice, and Support 2,563 People

    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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    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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    Our marriage was just about over

    and we were just going through the motions. I had just been made redundant and so I was at home during the day while my wife worked and the kids were at school. I was feeling pretty lonely and for some reason I started dressing in my wife's clothes when I was alone (I used to...
    chrissyaitch chrissyaitch 61-65, M 10 Responses Jan 1

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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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    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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    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 3 days ago

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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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    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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    one of them had to notice!

    i walk before i go to work in the morning. lately i have been wearing women's shiny leggings with leopard print or fishnet pantyhose underneath. man clothes on my upper half. some hose shows.but this morning i was feeling a little braver. i was wearing leopard print pantyhose...
    sbjj sbjj 56-60, T 1 Response Jan 21

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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 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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    I was 16 years old. I loved getting all fixed up

    as a girl and go to the drive in movie. Usually I have no problem running into anyone I knew. I went to the one that was 20 miles away. This one time I went to the ladies room. And standing pretty close to the door was a guy I worked with and went to school with. We weren't...
    deleted deleted 26-30 5 Responses Nov 10, 2015

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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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    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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    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 15 Responses Dec 27, 2013

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    This happened Sunday.

    Wife and I go to the casino on Sundays it is senior day. We get free play being seniors. I was dressed as a woman like always. I noticed this guy following me around and looking at me. Well I wasn't sure who he was or what he had In mind. I found my wife and sat down next to...
    deleted deleted 26-30 2 Responses Nov 24, 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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    I was at a friends house

    and I was changing into my pjs so I went into her room and took a pair of panties when everyone was in the kitchen. That morning i was changing into my day clothes and forgot about the panties and she saw, and was wearing the same panties and matching sports bra. We spent the...
    wild6464 wild6464 18-21, M 1 Response Jan 26

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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 4 days ago

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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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    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 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 5 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 9 Responses Mar 1, 2015

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    I almost did, my mom found some underwear I

    took from my cousin... I told her it my gf... I don't know if she buy it or not but we have never ever talked about it again
    LauraOCD LauraOCD 22-25, M 4 Responses Dec 26, 2015

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    So I had always been dressing

    whenever my parents would leave and run errands. So every time they left the house I would race into my moms room and immediately throw on a dress. Well this day went a little different, I was left home like usual but also was in charge of babysitting my younger sister who was 5...
    lcd6993 lcd6993 22-25 5 Responses 4 days 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 4 Responses Apr 19, 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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    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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    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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    It may have been just from my truck,

    across the street and up my front porch and inside but I'm very proud I took the risk of wearing leggings and knee high boots in public :) Almost got caught too :D
    MelissaTheSexyCd MelissaTheSexyCd 18-21 2 Responses Dec 15, 2015

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    AlexisRuiz AlexisRuiz 18-21, T 1 Response Dec 21, 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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    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 4 days ago

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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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    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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    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 2 Responses 3 days ago

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    HOLY CRAP!! Was that ever an experience?

    So I had to drive my co-worker home after a nightshift and I thought to my self, "on the way home I will enjoy my drive and wear some leggings or something" so I put on a thong and my black shiny Nike leggings and packed my knee high boots into my bag, put sweat pants on over my...
    MelissaTheSexyCd MelissaTheSexyCd 18-21 2 Responses Jan 4

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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 went to AbilineTx. to go to the ABS I was

    dress up in a red bra and panties and red dress my red wig I stop at a rest stop to put on some make-up and a trucker was watching me and came to my car and asked what I was up to . he asked me if I wanted to check out his rig .I said yes and we stayedin his truck for two hours...
    hotlicker68 hotlicker68 56-60, M 1 Response Jan 13

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    I was married to Debbie

    for 20 years and we had some great times but after working away for long periods we drifted apart and were divorced all of our married life I had hidden the fact or so I thought that I cross dressed. At every opportunity I would where her clothes and buy my own meet people on...
    yorksue yorksue 56-60, M 8 Responses Sep 5, 2015

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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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    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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    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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    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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