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I Caught Crossdressing

Personal Stories, Advice, and Support 2,459 People

    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...
    silkiehosewearer silkiehosewearer 31-35, M 26 Responses Sep 20, 2009

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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...
    silkysissy silkysissy 16-17 25 Responses Feb 6, 2012

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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...
    deleted deleted 26-30 28 Responses Oct 16, 2011

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    How I Become Wife Part 2 - mansi ne muje kaha ki aaj k baad tu hamesha hamare naam k piche 'ji ' laga kar baat karegi samji maine apna sir hilaya aur kaha samaj gayi ji wo dono...
    sejalshah484 sejalshah484 26-30 Oct 22, 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...
    susen susen 56-60 16 Responses Nov 23, 2009

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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...
    deleted deleted 26-30 Nov 16, 2013

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    Girlfriends Brother - it all came about when I was 17 with my girlfriend who helped me dress she loved it and the great sex.1 night we both felt like we where being watched from...
    sexyshellie sexyshellie 41-45, M 2 Responses Sep 22, 2013

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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...
    happilymarriedguy happilymarriedguy 51-55, M 3 Responses Jan 12

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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...
    silkydrawers silkydrawers 46-50 4 Responses Feb 5, 2012

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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...
    LaceyLisa LaceyLisa 61-65, T 11 Responses Jun 24, 2012

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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...
    jane1976 jane1976 31-35, T 20 Responses Dec 25, 2012

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    Caught By My Neighbour. - Well this was the first time I was caught by someone who was younger than me. It happened when very quickly but it seemed like it was ages. It all...
    2468metallicarule 2468metallicarule 18-21, M 25 Responses Jun 6, 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...
    w1492 w1492 31-35 12 Responses Mar 29, 2011

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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...
    cdlifer1955 cdlifer1955 51-55 11 Responses Apr 20, 2011

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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...
    JustGaby JustGaby 22-25, T 1 Response Feb 6

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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...
    allwrappedupinit allwrappedupinit 51-55, M 7 Responses Sep 26, 2011

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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...
    toromova toromova 36-40 2 Responses Dec 25, 2013

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    Close Calls - Well ever since i could remember I've always loved to dress up in women's clothing .I don't know what it is about but i love sliping on some panties and wearing some...
    joseluceroxxx joseluceroxxx 22-25 Oct 10, 2013

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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...
    gilman123 gilman123 46-50, M 19 Responses Apr 15, 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...
    lovevspink16 lovevspink16 18-21 1 Response Apr 5

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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...
    MissHarley MissHarley 18-21, F 8 Responses Nov 29, 2013

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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...
    sherrynpantyhose2k4 sherrynpantyhose2k4 51-55, T 58 Responses Sep 20, 2012

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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...
    mariah157 mariah157 18-21, T 43 Responses Apr 3, 2012

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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...
    Mrscuckolder Mrscuckolder 41-45, F 15 Responses Mar 11, 2012

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    How I Become Wife Part 3 - training for becoming BAHU mansi ne apni dost ko bulaya jo beauty parlour mai kaam karti h aur usse kaha ki isski waxing kar de. usne mere pure body ki...
    sejalshah484 sejalshah484 26-30 Oct 23, 2013

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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...
    boyinpanties101 boyinpanties101 18-21, T 13 Responses Dec 16, 2012

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    Want To Dress Up For My Aunt, Need Your Thoughts----part 2. - Hello All! About a year ago I wrote describing how my Aunt Lorraine was to come visit and how I wanted to dress up as...
    hotgarters hotgarters 46-50, M 4 Responses Oct 7, 2013

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    How I Become Wife Part 1 - this is my dream story. mera naam raj hai aur mai married hu. meri wife ka naam mansi hai. mai aur mansi college se saath mai h. hamari love marraige hui...
    sejalshah484 sejalshah484 26-30 1 Response Oct 22, 2013

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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...
    sexyshellie sexyshellie 41-45, M 1 Response Nov 21, 2013

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    Visitors - One Saturday my wife was feeling adventurers that we dress in matching outfits (my crossdressing is a real turn on for her) I readily agreed. Laid out our appeal which...
    wellheeled2 wellheeled2 51-55, M 1 Response Oct 5, 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...
    cdpaula cdpaula 41-45, T 8 Responses Jul 5, 2010

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    Just uploaded a couple of pics check them out!
    mrman77 mrman77 22-25, M Mar 3

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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...
    Leotard1988 Leotard1988 22-25, M 1 Response Jan 11

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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...
    sejalshah484 sejalshah484 26-30 Oct 23, 2013

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    Uploaded more pics go check them out!
    mrman77 mrman77 22-25, M 2 Responses Mar 5

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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...
    Bicd49 Bicd49 56-60, M 2 Responses Dec 19, 2013

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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...
    jml2000 jml2000 56-60, M 15 Responses May 9, 2012

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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...
    jadexxx19 jadexxx19 18-21, M 3 Responses Jan 1

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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...
    BizSuitStacy BizSuitStacy 46-50, T 20 Responses Dec 5, 2010

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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...
    lw85381 lw85381 56-60, F 8 Responses Jan 4, 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...
    sejalshah484 sejalshah484 26-30 Oct 25, 2013

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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...
    deleted deleted 26-30 Nov 20, 2013

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    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...
    GirlieSpirit GirlieSpirit 41-45, T 13 Responses Aug 8, 2010

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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...
    sissyboysgirlfriend sissyboysgirlfriend 13-15 25 Responses Feb 26, 2012

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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...
    DianeN9 DianeN9 26-30 1 Response Oct 23, 2013

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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...
    deleted deleted 26-30 7 Responses Feb 10, 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...
    elliecarr elliecarr 18-21, T 3 Responses Dec 24, 2013

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    How I Become Wife/Bahu Part 4 - jab mai room mai gayi toh mansi ne kaha ki yeh lo meri nighty aur pahen kar aao. kal se tum apni pahenana mai change karne chali gayi. wig k...
    sejalshah484 sejalshah484 26-30 Oct 23, 2013

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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...
    SarahCD707 SarahCD707 51-55, M 30 Responses Oct 2, 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...
    deleted deleted 26-30 1 Response Dec 7, 2013

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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...
    eric2maid eric2maid 31-35, M 13 Responses Nov 11, 2012