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I Caught Crossdressing

Personal Stories, Advice, and Support 2,551 People

    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
    61-65, M
    3 Responses Apr 29, 2015

    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
    56-60, T
    16 Responses Dec 5, 2010

    The Next People To Find Out

    I was on a school excursion and, just my luck, so were a couple of the bullies who were forcing me to wear womens' underwear. As I always had a longline bra on, I had to keep a thick school uniform pullover on in order to hide the signs. It was a hot day, and we'd been left to...
    deleted deleted
    Nov 20, 2013

    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
    6 Responses Feb 10, 2011

    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
    8 Responses Mar 29, 2011

    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
    4 Responses Sep 26, 2011

    Of course I was caught; tho it wasn't really a

    surprise to anyone but me! My soon to be second ex wife knew I dressed femininely and even knew I had two small TV based businesses going. I'd told her about my dressing before we got married and she seemed to accept it but after we got married she told me she didn't want to...
    amandatrane1 amandatrane1
    51-55, T
    4 Responses Oct 29, 2015

    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
    1 Response Dec 25, 2013

    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
    56-60, M
    7 Responses Sep 17, 2013

    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
    26-30, T
    1 Response Feb 6, 2014

    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...
    deleted deleted
    8 Responses Apr 20, 2011

    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
    1 Response Dec 7, 2013

    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
    22-25, M
    2 Responses Jan 1, 2014

    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

    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

    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
    10 Responses Mar 11, 2012

    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
    9 Responses May 10, 2011

    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
    14 Responses Apr 15, 2012

    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
    25 Responses Oct 16, 2011

    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...
    deleted deleted
    1 Response Aug 6, 2014


    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...
    deleted deleted
    2 Responses Nov 21, 2013

    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
    61-65, M
    2 Responses Dec 19, 2013

    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

    How i become housewife/bahu part 7 Fir anjali

    muje bathroom mai le gayi aur kaha dekho yeh sab kapade hai balti mai usse dhona hai tumhe aur yeh dusri balti wale kapade ko brush nai lagana samji . Maine kaha ji samaj gayi . Wo has rai thi boli bahit jaldi samaj jati ho sab aurat k kaam . 1 ghante k baad jab mai bathroom se...
    sejalshah484 sejalshah484
    1 Response Mar 24, 2016

    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
    1 Response Jan 11, 2014

    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
    30 Responses Apr 3, 2012

    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
    12 Responses Sep 15, 2010

    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
    7 Responses Oct 16, 2013

    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
    51 Responses Sep 20, 2012

    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

    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
    31 Responses Nov 29, 2009

    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

    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
    3 Responses Feb 5, 2012

    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
    26-30, F
    4 Responses Jun 25, 2014

    In The Hotel Hallway

    Well, I was staying in an older hotel in a nortwest city in the US. There was a wonderful breeze blowing up the stairwell that connected the floors, and I was in the middle of a twenty four hour period all cross dressing. (I'll post something on one of the other crosdressing...
    GirlieSpirit GirlieSpirit
    41-45, T
    9 Responses Aug 8, 2010

    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
    36-40, T
    2 Responses Sep 7, 2014

    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
    19 Responses Nov 10, 2010

    Caught crossdressed,mostly in lingerie.

    Yes,I've been caught so many times I don't even try to hide it anymore The first time by my mother,I was about 12.She didn't actually catch me dressed...she found my panty stash.I've been caught many times from my panties showing.In highschool my GF found out and she told all her...
    MisstressAndi MisstressAndi
    56-60, M
    2 Responses Dec 6, 2015

    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
    6 Responses Nov 5, 2012

    I started wearing my mom's

    and grandmother's nylons as a small kid but stopped until I was a teenager. One day I got the urge to try my mom's nylons. I was 14 when my mom caught me wearing her nylons. My mom was a hairdresser and wore knee highs all the time. She got mad and made me take off the knee...
    stephenjstasiowski stephenjstasiowski
    51-55, M
    3 Responses Jan 24, 2016

    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...
    deleted deleted
    6 Responses Aug 15, 2015

    Never thought I would get caught.

    My mom always left her nylons out especially knee highs. Curiosity got the better of me. My mom was still at work and nobody was at home. I removed my socks and slid the nylons on, I loved how they felt on my legs and I put on my sneakers. She caught me when I bent over to pick...
    stephenjstasiowski stephenjstasiowski
    51-55, M
    5 Responses Jan 28, 2016

    Getting Caught.

    I've been caught a few times.  But this one was at my grandma's house.  My grandma knew of my crossdressing.  She didn't mind it.  She didn't really understand it either.  But, if I wasn't out drinking or doing drugs then it was ok with her.  As I...
    sexyblackpantyhose sexyblackpantyhose
    31-35, M
    18 Responses Sep 15, 2009

    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
    1 Response Dec 24, 2013

    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...
    deleted deleted
    19 Responses Dec 25, 2012

    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

    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

    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
    56-60, M
    2 Responses Jul 3, 2014

    I walked out into my back garden one evening

    only to be greeted by neighbour, I was in the middle on the garden when I heard him and then saw him up a ladder against his house, giving him a clear view of me. I froze with fear when I heard him because of how I was dressed. Clearly visible in a black skirt, black tights and...
    leotardboy62 leotardboy62
    51-55, M
    4 Responses Aug 14, 2015

    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
    14 Responses Nov 23, 2009

    Caught By Babysitter

    im divorced and my x had our son one day when i came home from work i was so tired from working night shift i put on a black leotard and shiny tan tights and taped my penis back so im smooth as a girl i always loved leotard since i was 5 my sister always dressed me up in them...
    loveleotards50 loveleotards50
    46-50, M
    7 Responses Jan 1, 2013

    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
    6 Responses May 19, 2015

    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
    61-65, M
    15 Responses May 9, 2012

    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
    1 Response Dec 8, 2014

    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

    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
    21 Responses Sep 20, 2009
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