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I Caught Crossdressing

Personal Stories, Advice, and Support 2,626 People

    I was off one Friday

    and I thought it be fun to dress up in the lingerie and take some photo's. Being Friday and every one off to work around me I had the drapes pulled open a bit to get some light in. While I was doing my photos I heard the gardener next door and didn't think about it much until I...
    timcdofsd timcdofsd 51-55 6 Responses Nov 25, 2014

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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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    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 25 Responses Dec 25, 2012

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    Caught By A Couple Of College Lads

    I have been a closet cross-dresser since the age of ten and take every opportunity to paint my nails and put my makeup on. With my wife away working overseas, I decided to spend the whole weekend in my feminine attire. Early Saturday morning, I showered, shaved and prepared for...
    mascara247 mascara247 41-45, M 7 Responses Nov 5, 2012

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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 14 Responses Sep 15, 2010

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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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    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 17 Responses Apr 15, 2012

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    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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    Ok my mother worked in a restaurant in New York

    city I KNEW her hrs I thought so one time I got DRESSED thought had hrs to be tiamarie as l came out of bathroom with my makeup on went to living room there was my mom shocked NO WAY MAD NOT AT ALL ALLS SHE SAID R U HAPPY IN THOSE THINGS AND I SAID YES SHE SAID I LOOKED GOOD IN...
    tiamarie512 tiamarie512 56-60, T 5 Responses May 19

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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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    Telling your parents- I've read a few stories

    on here about some of you building up the courage to tell family about your dressing. I think I'm at the point where I either tell them, or stop completely, but I don't know where to go. I have a mother who would probably accept me, but my dad might not. We don't have a very...
    elliecarr elliecarr 18-21, T 3 Responses Dec 24, 2013

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    I have been caught so many time's,

    it is really not funny. If you are like me, please stop trying! You are only fooling yourself ! Because everyone knows, anyway. I don't know how, but somehow they figured it out. While you were busy covering you tracks. They were kind and quiet and let you do it. Your covert...
    royalflush70 royalflush70 41-45, M Jul 17

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    mrman77 mrman77 22-25, T 1 Response Mar 3, 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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    Here is an excerpt of an article I found on

    line. We all have our little secrets that we'd be embarrassed if anyone found out about, but stories of crossdressers being discovered are often some of the best... both humiliating and erotic at the same time, especially in the eyes of the crossdresser. It is often the ultimate...
    wellheeled2 wellheeled2 51-55, M 7 Responses Jun 6, 2014

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    If you read my stories you can see the past two

    nights I have worn my wife's lingerie to bed. We rarely sleep in the same room, much less the same bed. My question is, who thinks I can pull off a third night without getting caught, or should I hope I get caught and finally let my secret out? Please respond with your thoughts...
    toromova toromova 36-40 2 Responses Dec 25, 2013

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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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    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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    mrman77 mrman77 22-25, T 2 Responses Mar 5, 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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    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 39 Responses Apr 3, 2012

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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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    Caught By Neighbor

    At the age of 14 I would mow lawns and do gardening work for people in my town west of Boston in Sudbury Ma.  One client was a newly married couple that had a nice home with an inviting swimming pool.  The wife, Debbie was very good to me when I cut their lawn that summer...
    w1492 w1492 31-35 9 Responses Mar 29, 2011

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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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    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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    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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    Sister In Law.

    I am sitting at my desk minding my own business just a few moments ago when in comes my sister in law. I am wearing pantyhose. 46 L bra and a cat suit. My S I L looks right at me and asks where my wife is. I said she should be in the garden. With out a pause she says that I...
    sherrynpantyhose2k4 sherrynpantyhose2k4 51-55, T 58 Responses Sep 20, 2012

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    This morning actually.

    My neighborhood is extremely quiet in the morning, and my neighbors are old and white. I'm tall black with a feminine shape, especially my chest and my big butt. I don't dress all the time but I had the urge this morning. I walked around my yard, looking at the reflection of my...
    serenasgtballs serenasgtballs 26-30, M 1 Response Jul 24

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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 1 Response Dec 8, 2014

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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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    So this was back in year 8 (which is about 12

    years old). I was over at my best friends house, (we'll call her Amy) we were best friends at that time and still are now. We were casually just playing on her PlayStation in her room when her mum called her for dinner, although I was more than welcome in the house because I...
    leggingslover20 leggingslover20 18-21, T 4 Responses Aug 15

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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 2 Responses Jan 1, 2014

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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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    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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    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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    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 19 Responses Dec 5, 2010

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    I've been dressing since I was a little kid.

    My brother & I would go in our sisters' room & put on their clothes & play like we were them. Later I noticed he was still doing this. I found all kinds of girl's clothes in our bedroom. I saw them & I couldn't resist, I would try them on. I knew he did this & soon he knew I did...
    toromova toromova 36-40 1 Response Dec 24, 2013

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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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    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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    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 56-60, T 6 Responses Dec 4, 2014

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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 14 Responses Nov 23, 2009

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    Recently I was in target to buy some new panties

    and a bra. When I am out dressed I try to blend in. And I usually pass. I had on besides my bra forms and padded panty black jeggings a fluffy long high neck black and white sweater and black knee high boots with three inch heals , my makeup was full foundation powder mascara...
    taracd55 taracd55 56-60, M 4 Responses Apr 29

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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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    My First G/f.

    I was in 8th grade, she was a junior in H S. One day I was dressed in my room but had forgot to close my curtains all the way. She was cutting through our yard and looked up to see if I was home. I had no idea that she had seen me. A short time later she calls and asks me if...
    sherrynpantyhose2k4 sherrynpantyhose2k4 51-55, T 10 Responses May 10, 2011

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    This morning actually.

    My neighborhood is extremely quiet in the morning, and my neighbors are old and white. I'm tall black with a feminine shape, especially my chest and my big butt. I don't dress all the time but I had the urge this morning. I walked around my yard, looking at the reflection of...
    serenasgtballs serenasgtballs 26-30, M Jul 24

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