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I Caught Crossdressing

Personal Stories, Advice, and Support 2,511 People

    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 Dec 24, 2013

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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 10 Responses Jul 5, 2010

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    How I Become Wife/Bahu Part 5

    ek ghante k baad jab hum hall mai mile toh meri sasuma sofe pe baithe the aur saamne table pe kuch paper pade the. muje dekh k bole chalo sejal iss paper pe sign karo maine paper uthaya aur padh raha tha ki sasuma uthe aur mere kaan pakad k marod diya. aur kaha ki maine kaha...
    sejalshah484 sejalshah484 26-30 Oct 23, 2013

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    Permanent Sissy

    I have been crossdressing for years now not known to my mother (or so I thought). she is the only person I live with at the moment. when she was going to be out for a few hours I went to her underwear drawer and inside was the most sexy, silky, feminine underwear set I had ever...
    silkysissy silkysissy 16-17 26 Responses Feb 6, 2012

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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 15 Responses May 9, 2012

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    Jeff, You Are On Notice

    I am Harley, a part time actress, Recently I found Jeff poking about in the girls wardrobe department of our stage theatre , Jeff was not a very good liar and I easily discovered his desire to cross dress I made a little deal with him, I could get whatever items he wished to...
    MissHarley MissHarley 18-21, F 9 Responses Nov 29, 2013

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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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    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 10 Responses Jan 4, 2013

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    My Sissy Boyfriend!

    hi I was going to a party with 7 or 8 of my friends and my boyfriend was at my house as well, well while we were all doing our makeup downstairs my boyfriend found one of my dresses, some pantyhose and a bra and panties and went into the bathroom and put them on! well he forgot...
    sissyboysgirlfriend sissyboysgirlfriend 13-15 27 Responses Feb 26, 2012

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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 4 Responses Dec 24, 2013

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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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    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 28 Responses Oct 16, 2011

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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

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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 12 Responses Mar 29, 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 45 Responses Apr 3, 2012

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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 1 Response Jun 21

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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 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 7 Responses Feb 10, 2011

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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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    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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    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

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    mrman77 mrman77 22-25, T Mar 3

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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

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    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 21 Responses Sep 15, 2009

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    eric2maid eric2maid 31-35, M 5 Responses Jun 7

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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

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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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    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 36 Responses Nov 29, 2009

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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 27 Responses Sep 20, 2009

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    Caught By Mom At 13

    i used to go into my moms room and take her clothes and hide them in my room and wear them at night. Pretty much what i would do is put them on and sleep in them, then my alarm would wake up and i would then take them off. And one night i put on all white lingerie. panties...
    boyinpanties101 boyinpanties101 18-21, T 18 Responses Dec 16, 2012

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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 16 Responses Nov 23, 2009

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    mrman77 mrman77 22-25, T 2 Responses Mar 5

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    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 26-30 Nov 20, 2013

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    Caught By My Cousin

    I was doing some work, clearing the garden for my Aunt when I was 15. I finished about noon and she told me she was out for the afternoon and my cousin, Jenny, would not be back until 5:00ish. I said OK, maybe I will take a bath and just hang out till you all get home. Jenny...
    DianeN9 DianeN9 26-30 1 Response Oct 23, 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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    Im starting a group chat ANY full time cross

    dressers under the age of 20 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like their outfit of the days or stories of getting caught or telling people or going out in public in clothes. if you want to join. ms me fhnvs86
    lovevspink16 lovevspink16 16-17, T 1 Response Apr 5

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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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    Caught As The Maid

    I was recently honoring a bet to my g/f in which I had to clean her apartment as a French maid. I was dressed to the hilt and even curled my hair, pinned it up and added a cute maid headpiece. While I was cleaning, my g/f left to work out at the gym. She was gone for a few hours...
    eric2maid eric2maid 31-35, M 14 Responses Nov 11, 2012

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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

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    Department Store

    This happened to me recently and was kind of funny. I found a store that has some really cute things and they are located in a dying mall on the edge of town so not a lot of traffic. I wanted to get some new clothes (I don't have a lot) and decided that I could go there and shop...
    Cyndie1 Cyndie1 46-50, T 8 Responses Jul 17, 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

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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

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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 15 Responses Mar 11, 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 17 Responses Sep 15, 2010

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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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    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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    How I Become Wife/Bahu Part 6

    mansi ne muje kaha ki aaj se tum koi decision nahi le sakte ho. aur pura din saaree aur sab jwellary pahene rahogi aur sab se main cheez h ghunghat jo pura din dal k rakhna h samji. maine kaha ji samaj gayi waha doorbell baji sasuma ne kaha ki jao sejal darwaja kholo.? main...
    sejalshah484 sejalshah484 26-30 1 Response Oct 25, 2013

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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 4 Responses Aug 6

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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

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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

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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 20 Responses Dec 5, 2010

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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 21 Responses Nov 10, 2010

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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 1 Response Jan 11

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