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I Caught Crossdressing

Personal Stories, Advice, and Support 2,557 People

    As I've mentioned in my earlier stories,

    I got into cross-dressing when I was coerced into it at school. This coercion continued into my adult life and allowed for no respite. So, one time just short of my twentieth birthday, when I had a doctor's appointment for a physical, I had to go wearing womens underwear. At...
    deleted deleted 26-30 1 Response Dec 7, 2013

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    Caught On My Day Off

    I was getting really stressed at work so I told the wife that I needed a day off. She agreed. We couldn't get our schedules in sync so I had the day to myself. I was bummed so I decided I would get dressed up. I waited until the kids were on the bus, I would have maybe four hours...
    JoanneF JoanneF 36-40, F 16 Responses Sep 15, 2010

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    Caught By Sister

    I was about 15 years old when I started wearing my sisters clothes. She was older than me by 3 years but had lots of sexy clothes. One day while she was out for the afternoon or so I thought I went into her room and found that she had left her black lace bra and matching panties...
    miata21 miata21 26-30 6 Responses Oct 16, 2013

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    When I was in my teens,

    starting when I was 13, every summer holiday I use to help out at a holiday chalet site for school children events, especially disadvantaged or disabled children. I use to help out a lot and became a favourite of the sweet young woman Claire (probably ~35) who loved all the help...
    imogentranny imogentranny 36-40, F 4 Responses Apr 13, 2014

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    I was 14 when I was caught.

    I had borrowed clothes of my friends Mums dirty linen basket including a pair of pantyhose, lacey maroon knickers, a bra, slip and a light green pleated skirt. I bundled them in my school bag made my excuses and left my pals house. I went in the park where there were no lights...
    Bicd49 Bicd49 56-60, M 2 Responses Dec 19, 2013

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    You were so afraid of being caught.

    Now, with my help, look at you!
    eric2maid eric2maid 31-35, M 5 Responses May 10, 2014

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    Okay, I just read Kim1Girl's caught-dressing

    story (from March of last year, I think), where she got caught in a hotel when they double-booked her room, and it reminded me of my own hotel experience in San Jose. It was a business trip, one that I'd started making semi-regularly, and so I knew a little bit what things I...
    AzabethTV AzabethTV 51-55, T 6 Responses Dec 4, 2014

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    By my parents. Several times already,

    while I was wearing them or when my mom was cleaning my room and stumbled upon my stuff. When I was about ten or something I used to steal my cousin's clothes who's about the same age as me and take them home where I would happily dress late at night. Now that I'm older I buy...
    JustGaby JustGaby 22-25, T 1 Response Feb 6, 2014

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    Hello,my name is jacob

    but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this. i am now seeking help from someone who lives near me. i live in Virginia and am looking for some one I can meet, i love EP...
    zoey764 zoey764 18-21, T 2 Responses Jul 23, 2014

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    By The Neighbor

    This happend around when I was 15 yrs old.  As my sisters were off at college and it was just my mom and I at our apt.  I was home from school as we didn't have any school that day.  But my mom still had work.  So I got myself all dressed up looking pretty...
    pantyhoseslut pantyhoseslut 22-25, M 33 Responses Nov 29, 2009

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    close call, I think! I was home alone

    for a few days during the daytime's so i thought it would be a good idea to start ordering womens clothes to save me wearing my mums. After the last item came (a pink knee length dress) i tried it on while wearing 6 inch platform heels, a wig and makeup. As i was admiring myself...
    jadexxx19 jadexxx19 18-21, M 3 Responses Jan 1, 2014

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    I have been dressing

    since I can remember. I was and still am a skinny guy. I have long hair and I am also blessed with very little body hair (nearly nonexistent) which I do keep completely shaved off and as I mentioned I am quite slim. I weigh 147lbs and stand 5'9" with a really girly butt. I have...
    Danielleknowsall Danielleknowsall 31-35, T 2 Responses Aug 11, 2014

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    Out In The Open

    My wfe found out i like to crossdress about 3ys ago and took it better than i thought. But now iv found out that since then she has told her freind and also her mother. Iv spoken to her mother about about it and she is cool with it and even bought me some nice underwear for...
    jane1976 jane1976 31-35, T 23 Responses Dec 25, 2012

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    Caught Crossdressing In A Store

    One night I was away from home traveling staying in a motel. I had my girlie stuff with me and I got all dressed up and made up and I went out for a drive. I was nervous going out dressed but I like the thrill of it. I decided that I would be really brave and I stopped at a 7...
    bethanngirl bethanngirl 56-60, M 23 Responses Nov 10, 2010

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    Halloween

    my first ever proper dress that my family new about was Halloween my mum told me I could dress up as anything I wanted to my sister was going as a sexy fairy so I said to my sis who knew I dressed I am going as the same as you I don't think mum will let you but go on see what...
    sexyshellie sexyshellie 41-45, M 1 Response Nov 21, 2013

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    I was caught the first time by my neighbor

    and he took advantage of catching me.
    alexiswcd alexiswcd 56-60, T 2 Responses Jun 21, 2014

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    My earliest memories are of my painting my

    nails. I was about Four. Later, I would start dressing. I was caught by my mother around age 9. I was dressed all the way. Dress, slip, bra and stockings. She made me get out of bed , and wait for dad to come home. She said I looked better than her in the dress. I have married...
    Wb5mpu Wb5mpu 61-65 Dec 8, 2014

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    Secretary Caught Me!

    Our office is small just 4 people. My secretary and myself are very close, she knew i was an avid crossdresser but had never saw me and had never said she wanted to. One Sunday I was behind on some work, it was a holiday weekend and i thought everyone was out of town. So me being...
    deleted deleted 26-30 27 Responses Oct 16, 2011

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    Caught By Mom

    A couple years ago my family was out for the night so I decided to dress in my sisters clothes. I had on a lacy thong and matching bra with beast enhancers in it, a mini skirt, shaved body, a button up blouse, and high heels. I was putting on makeup when my mom entered into my...
    mariah157 mariah157 18-21, T 42 Responses Apr 3, 2012

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    My Daughter Found Me.

    I had the day off. My wife had to work and my kids were off to school. My oldest daughter, who is 20 yrs old, off to study for a test at the collage library. Great, I have the house to myself probably all day. I changed into my pantyhose, bra and a black and white floral house...
    mat2Robin43 mat2Robin43 51-55, M 10 Responses Sep 17, 2013

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    Caught By My Girlfriend

    After my first wife and I divorced, I thought I would be single forever. I would never meet another girl, mistress, like her who wanted me dressed most of the time; a girl who totally believed in feminization and domination and gave me hormones, clothing and men. Of course she...
    cdlifer1955 cdlifer1955 51-55 11 Responses Apr 20, 2011

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    Mom Finally Accepts

    I was raised by my mother and as she had to work I had plenty of free time. She had caught me several times from the age of about 9 but finally shortly after my 11th birthday she caught me yet again. This time was to be different. It was a Thursday night she had caught me and she...
    LaceyLisa LaceyLisa 61-65, T 11 Responses Jun 24, 2012

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    Well almost. I had gone dress shopping

    and was in the changing room trying a dress on when my cell phone rang. It was my mom. She almost never calls my cell phone so thought it might be something important so I answered it. As I was standing there in my bra and panties talking to her the sales lady walked up and said...
    mat2Robin43 mat2Robin43 51-55, M 3 Responses Jul 3, 2014

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    It Wasn't My Fault- Really

    After all the close calls growing up, wearing a half slip in bed and mom wanting to pull the covers down, and so forth, I finally was caught. And it really wasn't my fault., as you will see. I was traveling on business in Durham, North Carolina and had some down time, so I went...
    Kim1girl Kim1girl 56-60, T 13 Responses Mar 10, 2013

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    Please allow me to tell my story about how am I

    caught by my Facebook friend. About 2-3 years ago I found a very nice girl's profil in Facebook. She lived neer to me therefore I signed her to my friend. She confirmet the relation. Unfortunately I was really shy and I don't dare write to her. Recently I found a web portal...
    Leotard1988 Leotard1988 22-25, M 2 Responses Jan 11, 2014

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    mrman77 mrman77 22-25, T 1 Response Mar 3, 2014

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    It Happened To A Friend Of Mine

    This is a true story, but it's not about me. My mother may have suspected I had dressed up in her clothes, but she never caught me at it. Someone I know, a friend of mine shared a story with me about getting caught, and I would like to share it with you. My friend Carrie is a...
    BizSuitStacy BizSuitStacy 46-50, T 18 Responses Dec 5, 2010

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    My Sister's Boyfriend

    I remember when I was staying at my aunt's house.  She new of my cding so I new I was always safe to dress there.  Well as I was staying there.  My aunts house was located in the same city as where my  sis was going to college at.  Which was also kewl as she was the one...
    silkiehosewearer silkiehosewearer 31-35, M 26 Responses Sep 20, 2009

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    Caught Stealing From Friend 2

    So i got the call today, she said i was to come over to take my punishment, and i better be wearing panties. I waited till wife went o work then got showered and went over. She was waiting for me in her kitchen i tried to apoligize but she said keep quite and *****. Well i didnt...
    gilman123 gilman123 46-50, M 19 Responses Apr 15, 2012

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    The First Person To Find Out...

    was a younger cousin of mine. Quick background. I was bullied at school and, at the start of the school year when I was just 14, I was forced by some boys in my class to put on a panty girdle and start wearing it every school day. By the middle of that term, I was wearing panties...
    deleted deleted 26-30 Nov 16, 2013

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    my first time being caught was around the age

    of 12 I was so thrilled by wearing panties or lingerie...I was trying to get caught...my older brother was home and I would put my clothes in my dads bathroom and I would ***** down to panties and bras and would walk down hall to bathroom forth when I heard him walking in...
    forbidyn forbidyn 41-45 3 Responses Mar 23

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    In My Panties & Bra

    One hot summer afternoo. It was a Sunday and I was home alone. I decided to go up on the pool deck and relaxe in the screen house wearing just panties bra and half slip. I did have my clothes with me incase anyone came home. While sitting there in my lingerie enjoying the hot...
    silkydrawers silkydrawers 46-50 3 Responses Feb 5, 2012

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    Paula Caught Dressed

    well it during one summer my long ago,my parents had gone on vaction and be gone for a week so i had my secert hidden place of clothing i had got by selling firewood for money.I went in and shaved my body completely. I got short black mini dress out red lace bra and panties,red...
    cdpaula cdpaula 41-45, T 9 Responses Jul 5, 2010

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    Caught By My Neighbor Pt. 2

    She then walked up behind me and reached around the front of the dress and grabbed the bulge that my **** was making in the front my dress and said that we would have to get rid of that somehow if you where to really look like a woman. She then brought me over and sat me on the...
    allwrappedupinit allwrappedupinit 51-55, M 7 Responses Sep 26, 2011

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    Sarah Was Naughty In The Hot Tub

    I went down to our complex hot tub late last night. I wore girls’ bikini briefs under my shorts. I could have claimed that they were just regular men's speedos even if a little thin looking, except that men don't wear pink speedos with little lace embroidery around the hems. To...
    SarahCD707 SarahCD707 51-55, M 30 Responses Oct 2, 2012

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    I was dressed up like a sexy woman at a public

    park & it was around 8pm & still daylight. I was wearing a nice fitted navy blue pencil skirt with a longsleeve black cotton top & a sexy long haired auburn redish wig, I looked very sexy & i'm gifted with a big hot sexy woman's butt. When I came out of the woman's restroom, 2...
    samantha1020 samantha1020 31-35, T 2 Responses Sep 7, 2014

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    I was about seven when I started sneaking threw

    my moms closet. One day I really wanted to wear my moms pantyhose, until my brother came home. I didn't know until he was already at the top of the stairs. I wasn't scared or anything cause I didn't know it was not "normal". So he saw me and just froze in place, and just laughed...
    Julius24 Julius24 18-21, M 3 Responses Aug 6, 2014

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    Mom And Sis

    When I wa about 12 my older sister had dressed me a couple of times in one of her dresses. I had long hair and she would put a couple of hair clips in to give me a girls look.And it was always done for fun. We always did this on saturday when my mother went to work. One day she...
    deleted deleted 26-30 6 Responses Feb 10, 2011

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    I broke my dads clock I was

    so afraid he would tell everyone I am a CD I just left for the day wham I got home he was actually in a good mood he doesent know I think but I'm preety sure he suspects I do I felt bad cause I stole my freaind sisters panties and I'm at a point where I don't know what to do...
    death2234 death2234 22-25, F 4 Responses Jun 25, 2014

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    eric2maid eric2maid 31-35, M 6 Responses Jun 7, 2014

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    Caught Dressed As A Woman

    It was a weeknight and I was out cross dressed enjoying dinner. About half way through dinner a fellow from work and his wife came into the restaurant. He immediately recognized me. Well, it happens I said. Since there was no place to go I finished dinner and paid the bill...
    jml2000 jml2000 56-60, M 16 Responses May 9, 2012

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    Oh no! That's my boss over there,

    he can't see me dressed like this! Please let me leave!
    eric2maid eric2maid 31-35, M 3 Responses Jun 7, 2014

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    I Aranged For My Husband To Be "caught"

    I am the dominate wife of my sissy husband who I keep in chastity as punishment for an affair he had last year. I also make him cross-dress frequently to remind him of his submissive status.I love big boobs so he has to wear a 42 G bra with large forms with firm nipples. He is...
    lw85381 lw85381 56-60, F 11 Responses Jan 4, 2013

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    Mother Caugth Me At 18 Teen

    I always loved panties,  and then I started to dress up in all kinds of girls things the experience was setting the stage to look more and more like a girl. i am not a very big person and at the time I was about 119 lbs and 5 foot 5 inch 18 years old, Halloween yes. I...
    susen susen 56-60 15 Responses Nov 23, 2009

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    Cought Him Cross Dressing.

    I should point out that I came home one day and found him cross dressed after he had shown me his clothing. I found out he has been a sissy every since he was a young boy. He is inadequate to have sex with me any more. I have taken on a black stud.
    Mrscuckolder Mrscuckolder 41-45, F 14 Responses Mar 11, 2012

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    Not sure if this counts,

    but I did get caught wearing my ex-wife's nylon nightgown one night. This was before I really started crossdressing. As a teenager I used nylon items to ********** while I was looking at women wearing lingerie. I stopped all this when I got married until one night. It was...
    happilymarriedguy happilymarriedguy 51-55, M 2 Responses Jan 12, 2014

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