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I Was Caught Crossdressing

Personal Stories, Advice, and Support 1,913 People

    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 12 Responses Jul 22, 2012

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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 about 7,8 I found a half petticoat

    of my moms and decided to take it to my room and try it on. I pulled it up under my armpits and it was like a dress that any girl my age would wear. I would twirl around and it was so comfortable that I hid it and would do it again as often as I could. Fast forward to about 12...
    needtodo needtodo 56-60 2 Responses Jan 1

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    YUP. GOT CAUGHT RED HANDED.

    KINDA. ANYONE UP FOR SOME STORY AND PIC SWAPPING TRADING?
    MacksInner MacksInner 31-35 5 days ago

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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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    I dress up when I travel

    for work. Sometimes I step out into the hall way, I guess for the thrill of being seen. I've even gone to get ice...nothing. But on my last trip I took another walk down the hall, looked out the window, turned around, walked back my room. Inserted the card...nothing, the...
    Nyssa59 Nyssa59 56-60, T 4 Responses Dec 17, 2014

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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 9 Responses Feb 5

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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 9 Responses Mar 1

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    Teenage Days

    My older sister and I always got on well together. There was not much of secrets between each other. Whilst growing up I had seen her develop and used to ask the usual questions and she had never shied away from showing me her body. She was older to me by a year and half. It was...
    DilXXX1982 DilXXX1982 31-35, M 8 Responses Aug 9, 2012

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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...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 9 Responses Aug 20, 2014

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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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    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 first got caught at my gay best mates party.

    My gay mate had like a 3 day bender party and on the 1st night we had like a one to one talk in the mum room because we was high on drugs and I told him how I crossdress and he told he if you wanted to dress up at his I could do it anytime like wear his mum stuff because his mum...
    missjazzmin missjazzmin 18-21 Feb 1

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    went on a work trip and a female coworker went

    to the bar and found me there on a "date" with a guy I meant on Craig's list.
    Therealjason Therealjason 31-35, F 2 Responses Jan 16

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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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    My wife found my makeup

    and pictures on my phone. Not a pretty sight. We have not had sex in 20 years, I do not cheat but like to dress up in private. She cannot understand and feels betrayed. I feel stupid and embarrassed, but know I cannot stop. Been wearing panties every day for 5 years, in private...
    jazz2013 jazz2013 56-60, M 4 Responses Feb 8

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    I was caught by my landlord we told him we were

    having problems with the pipes in the bathroom for master bedroom I was home alone so I was crossdressed I did not realize he had come over to check the pipes he had went under the house to check them before he knocked and he's saw me through the bathroom window when he knocked...
    Edwardkarter Edwardkarter 36-40, M 3 Responses Feb 2

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    After a night of drinking n going home i

    decided 2 dress up. So i snuck in 2 my moms room while she was asleep tryn 2 b quiet as possible without waking her(stealth mode) crawling on my knees n belly 2 not b seen n darkness just in case she woke. Got a few or more pairs of heels that i like. Made it back 2 my room with...
    whitwhit86 whitwhit86 26-30, M 5 Responses Feb 5

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    my wife saw some pics I had on my iphone.

    I had on a beautiful dress, makeup, my favorite black shapewear and a nice brown wig. she just looked at the phone then at me, I was expecting anger or at the least the lets talk about it speech but no all I got was laughter. she will never know the damage she did to on thee...
    Stacy1165 Stacy1165 36-40, M 6 Responses Mar 3

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    A night out as Rhonda had me visiting a local

    establishment where a band was playing that I follow. I was with a friend, and she is very acceptable of my crossdressing. I was beautifully dressed in a blue blouse and a red skirt and 2" blue pumps. I had just had a facial and had my arms, legs, chest and back waxed. I had...
    SweetRhonda SweetRhonda 51-55, T 5 Responses Apr 8, 2014

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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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    Last Super Bowl I made a bet with a girl

    who I was seeing at the time named Mary who was a huge Seahawks fan. We decided that the loser had to wear what the winner decided for 1 hour. Of course Seahawks dominated the Broncos which mean I had to wear what she picked. We found a time when Mary's roomate was gone for the...
    wildcard23 wildcard23 22-25, M 6 Responses Dec 24, 2014

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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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    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 16 Responses Apr 15, 2014

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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 was just wearing my kaftan this morning

    before I got dressed. I decided to paint my nails purple for fun. I had just finished painting them and was cleaning up the kitchen when our roommate walked in the front door with a friend. There I am-red toenails, purple fingernails and a kaftan when a strange woman walks in...
    Sharon03 Sharon03 61-65 9 Responses 5 days ago

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    Me and my girlfriend just moved to a new town

    and she ask me if I would like to go shopping with her so I said yes as I had nothing else to do. When we got to the mall she asked me what female underwear looked the cutest so I said pink ones with little harts on and a bow on top,then she pick up a matching bra. Then she took...
    Manudglh96 Manudglh96 18-21, M 4 Responses Jan 6

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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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    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 15 Responses Jan 10, 2014

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    I've been caught several times by my wife.

    She's not really cool with it but does tolerate. I've never dresses with wigs, make-up or anything female from the waist up. I Just like skirts, panties, heels and nylons. She's ok if I'm not dressing around her. Almost got caught by my parents a few months ago. I went to...
    shadowplt shadowplt 51-55, M 1 Response Feb 24

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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 3 Responses Apr 8

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    When I go out dressed

    as a woman I usually go at night because I don't want my neighbors to see me, However several years ago I went on an afternoon shopping trip as I wanted to buy some lingerie. I wore a black business suit with matching skirt and a white blouse. The trip was uneventful until I...
    Stephaniegirl226 Stephaniegirl226 36-40, M 12 Responses Oct 3, 2014

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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 5 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 12 Responses Nov 6, 2014

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    I was home alone my GF was gone

    for the weekend so I took the opportunity to dress. I went and got a sports bra and suntan panty hose I put on a nice dress and some high heels, a pair of knee length boots with 4 inch heels. I stayed like that all day which was Friday. That night I slept in a babydoll nighty...
    pmgurl pmgurl 51-55 8 Responses Aug 16, 2014

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    I kept it from my wife,

    but she guessed i was doing it. I wear men's underwear leaving the house, then change into panties at work. I also wear dresses,skirts & lingerie when staying in hotel's i
    simonsteane simonsteane 46-50, M 4 Responses Apr 7

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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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    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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    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 15 Responses Jan 11, 2013

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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 19 Responses Jun 11, 2014

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    Part 2 After cleaning up I remembered my mate

    said I could where his mum stuff so I went in the shower and had a full shave then went straight to the mum room opened the wardrobes doors and had a filed day I took out the black body con tight mini dress with black stocking with the straps and a pink lace thong and bra...
    missjazzmin missjazzmin 18-21 2 Responses Feb 1

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    Well here's what happen today I'm 16 in high

    school and I was wearing pink polka dot thong and spandex over and red sports bra and over my guy cloths so I went to school and went through my day and during my lunch I didn't feel good and I went to the nurse which sent me home and my parents know I wear panties and...
    AZCROSSDRESSER AZCROSSDRESSER 18-21, M 5 Responses Mar 29

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    I came home early to vacuum

    and mop the house for company that is coming over tonight. I enjoy doing housework simply dressed in a bra and panties, lace of course, sometimes a pretty sundress. I feel very feminine this way and it brings me great joy. My FedEx man usually just leaves packages at my front...
    parttimelisa parttimelisa 51-55, M 4 Responses Feb 13

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    My Mum And Sister

    My Sister found some of my pantyhose but i was able to say they were my girlfriends and i thought i had gotten away with it. But the next day she must have gone through my laptop and found pictures of what they first thought was a girl (massive compliment to me :P) but realised...
    lucyxcd lucyxcd 18-21, M 11 Responses Apr 3, 2013

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