I Was Caught Crossdressing

Personal Stories, Advice, and Support 2,497 People

    Fiction. I will continue

    as as blog if it has positive response. It was late evening when I returned home after spending a couple weeks visiting my Dad, stepmom and half sister and went to to my stepmothers sisters wedding. Another story for later. At any rate Mom greeted me and told me to put my...
    angiecan angiecan
    51-55, T
    22 Responses Apr 27, 2015

    One afternoon, I was walking from my car to my

    house when the a neighbor girl, who was probably 13 or 14, riding her pretty pink bike (I would have killed for her bike when I was her age).  She stopped in front my my house. "Hi" she said "Hello" I said back. "Have you ever worn lipstick?" !!!!!!!!!!!!!!!! Oh my gosh...
    crosskimmy crosskimmy
    31-35
    3 Responses Apr 6

    just been caught by a delivery driver wearing a

    Simon Jersey black dress and apron. The wife thought it was hilarious there she was in jeans, jumper and trainers and the driver saw both of us. Luckily she went to the door. She's gone out now but wants me to do the washing up and the hoovering while she's out and start tea...
    Bower99 Bower99
    56-60
    2 Responses Jan 27

    Well, I wasn't really caught

    but almost was close enough. I was in my sister's room when no one was home. I started to parade around in her bra and panties when I heard the front door open and she was running up the steps. I did the only thing I could think of and jumped into her bed and pulled the covers...
    ReneeTalley ReneeTalley
    61-65, M
    2 Responses Feb 3

    I owned an office cleaning business

    and working when they were closed and no one around. Sometimes I'd take my girl clothes in and change and clean as a woman but I always kept my change of clothes near. That night I had finished one place dressed and figured as no one was around I'd drive to the next place as I...
    Lyndaloves1957 Lyndaloves1957
    56-60, T
    11 Responses Nov 6, 2014

    I was caught by my teacher.

    I had worn panties for a while and when i was a junior in high school i stayed after school to get help from my teacher. I asked him to come over and help me with a question, he came over and helped then went and sat back down. About 5 mins or so went by, and he called me over...
    Pantieboythong Pantieboythong
    18-21, M
    3 Responses Mar 14

    Thinking about it now,

    after all the close calls and 'hiding' of things, deep down I suspect many of us hoped we would be caught. But caught by someone accepting and understanding that might have allowed us to experience that side of ourselves. Without the cruelty and ridicule that too many have dealt...
    Allysoninaz Allysoninaz
    46-50
    4 Responses Apr 19, 2015

    Caught

    When I was 13 I had been crossdressing for 3 years now and was never caught. I started telling a few girls I always talked to about how I crossdress and they told me I should tell my parents but I knew I didn't have the guts to tell them at all. Well one day when my mom left for...
    lime277 lime277
    22-25
    12 Responses Jul 22, 2012

    I was 13 and at the weekend my mum

    and sister and brother went out. I stole £10 from my mums purse and went to the drug store. I bought red lipstick and red nail polish. I went home and put on knickers and a dress. Then I painted my toenails red and my nails red. I got a dress and heels and put them on. My mum...
    EvaMarie1406 EvaMarie1406
    22-25, F
    5 Responses Apr 24, 2015

    This is embarrassing My name is Damien I am a

    male teen crossdresser It was a school day and I forgot that I had painted my nails last night red so it was no problem really. I went downstairs to look for the nail polish remover there wasn't any LEFT!! So I say to mum I can't go into school today because my shoes don't...
    EvaMarie1406 EvaMarie1406
    22-25, F
    3 Responses Apr 11

    It was late and I was alone with my mom in the

    house, she was watching tv and eating in her room, so why not? I went over and got out all my clothes and slipped into a nice pair of orange panties, a bra with cute flowers on it, black yoga pants a long vneck and a sweatshirt and went to my bed to text my friends, before I...
    Diamondcdx16 Diamondcdx16
    18-21, M
    16 Responses Jan 10, 2014

    I got dared by my sister to dress in her clothes

    so she got me a a bra, thong, wig,high heel shoes and the most beautiful dress also she done my make up and I looked like a fairy tale princess in pink. My mum walked in and my sister said that she always wanted a little sister. The next day my mum told me to dress up again and...
    deleted deleted
    26-30
    5 Responses Jan 7, 2015

    I was at a friends house

    and I was changing into my pjs so I went into her room and took a pair of panties when everyone was in the kitchen. That morning i was changing into my day clothes and forgot about the panties and she saw, and was wearing the same panties and matching sports bra. We spent the...
    wild6464 wild6464
    18-21, M
    1 Response Jan 26

    When I go out dressed

    as a woman I usually go at night because I don't want my neighbors to see me, However several years ago I went on an afternoon shopping trip as I wanted to buy some lingerie. I wore a black business suit with matching skirt and a white blouse. The trip was uneventful until I...
    Stephaniegirl226 Stephaniegirl226
    41-45, T
    11 Responses Oct 3, 2014

    I am going to try and target 3 caught

    crossdressing stories by the weekend Here's story no1 they do come in parts. The bridesmaids story.... Hi my name Eric I am 17 and this is a story of my day as a bridesmaid. It was 9:00am and my sister was getting married I wanted to go in the bridesmaids dressing room and...
    EvaMarie1406 EvaMarie1406
    22-25, F
    3 Responses Feb 5

    I was caught when I was 14.

    My parents were at work and I had the urge to put on one of my mums dresses and a pair of her knickers. I had been dressing for a year or so in secret and always loved my time alone. I was in the dress and i didn't hear my mum come in the house. She didn't shout I just heard her...
    deleted deleted
    26-30
    15 Responses Jun 11, 2014

    When I was 14 I started crossdressing.

    My Mother and older Sister were gone quite a bit. One day after school I went home and started putting on my sisters clothes. Bra, panties, wig, skirt, sweater and high heels. I was applying lipstick and admiring myself in the mirror. My Mother came home early and walked in on...
    Stephaniegirl226 Stephaniegirl226
    41-45, T
    7 Responses Sep 13, 2014

    sat in class today and panties were showing

    and the girl asked if those were panties? and I said no but she said yeah they are I have the same pair ??
    deleted deleted
    26-30
    10 Responses Sep 3, 2015

    Caught By My Mother

    I was 16 at the time and had been crossdressing in my mother's clothes since I was 6. I thought I was clever about it, but more on that later. A friend of mine had 3 sisters who were 15, 14 and 12 at that time. I remember we had been out after midnight one saturday night and...
    MelissaStewart MelissaStewart
    26-30, M
    12 Responses Apr 18, 2013

    It was was the fist day summer break it was

    just me and my mom home .I was in her room dressing up in her clothes i hear her come up so i tried to hid in her closet but it was to late . She came in i was standing there with no where to go and she stopped and said what are you doing wearing my clothes. I just said i like...
    laura1974 laura1974
    41-45, T
    5 Responses Feb 4

    today my mom lift home

    for work after she lift I put a pair of panties on than my jeans a bra than my shirt I went to are apartment to check are mail I get back and that when I realized I didn't get the key as I lift so I bend down showing my *** and the thong panties I was wearing to get the...
    gueenemma418 gueenemma418
    22-25, T
    1 Response Apr 14

    A long time ago now I lived on my own

    and would dress up all the time I got so used to it and it was perfectly normal for me. One day someone knocked at the door and I went to open it completely forgetting that I was wearing pink tights and a really short black skirt. I opened the door and one of my friends was...
    deleted deleted
    26-30
    9 Responses Aug 20, 2014

    So I was 16 when I first got caught

    crossdressing in my sisters clothes. I was wearing my older sisters backless dress and her floral balcony bra, she was 19 at the time but was the same height and size as me and her clothes fit me well. She wasn't the one who caught me though, it was my other older sister, she...
    anonimousguy anonimousguy
    16-17, M
    2 Responses Mar 3

    My First Time

    I first started crossdressing when I was thirteen, I was at home by myself because my mom had gone out shopping with her friend Naomi. As I walked past my moms room i saw a pair of black pvc thigh high boots with a 6 inch heel and a platform on the bed. I wasnt sure at first...
    touchmythigh touchmythigh
    26-30, T
    21 Responses Dec 8, 2011

    I Told My Bestfriend

    Hey everyone well the other night i decided i was going to come out and say everything to my bestfriend Amber. Her and I have been bestfriends for a year and she is very trustworthy so i thought i would tell her. So i told her i needed to tell her some of my secrets and she...
    AutumnCD AutumnCD
    18-21, M
    12 Responses Jan 11, 2013

    The Lady Down The Street

    That lady whose house I would cut the grass who left her shoes outside. One afternoon I had gotten my hands on a Bikini a few yards down from hers and was wearing it when I went into her yard; she had high bushes which concealed the yard. I was working my way around the edge to...
    deleted deleted
    26-30
    11 Responses May 23, 2012

    this happened when I was 10 years old my mom

    and sister went out to the store and she said she would be back in like 2hrs so I went into my sister's room to get some close to dress in while they were gone so I got a thong matching bra a dress heels and a blouse and put them on and apparently my sister changed her mind and...
    heaven2211 heaven2211
    36-40, T
    6 Responses Mar 5

    My Mother In Law Busted Me And More

    Her mother caught me wearing her panties, bra, and a nightgown. Back about the time my first wife found out about my wearing women's clothes, I had a real strange experience with my mother in-law. She had a habit of taking naps in the afternoon between 1pm and 4pm in the nude. On...
    deleted deleted
    26-30
    13 Responses May 23, 2012

    Part two So my mum came back with bags full of

    shopping and told me to sit down she said I knew you was dressing up in my stuff I just never caught you and I wasn't going to bring it up because I'm guessing you weren't comfortable with it yet but now I know fill free to dress up anytime where at home and then she gave me the...
    missjazzmin missjazzmin
    18-21
    9 Responses Feb 5, 2015

    Well, I was caught by my best friend today.

    I was wearing my pink with hearts bra today with my girlfriend and he showed up. Idk but somehow I guess he saw my bra strap. I lied and told him it was a bet between me and my girlfriend. Thank god he didn't know I was wearing neon green lace panties xD
    pantyboy94 pantyboy94
    22-25, M
    3 Responses Feb 8

    She told from today onwards u have to wear

    single strap panties at all times but first you have to be hair free and gave some hair removal creams u have to use it twice a week.in my presence u have to wear only transparent panties and bra. And in our relationship I will be dominant.after our marriage u can wear girly...
    Suhanihotty Suhanihotty
    22-25, F
    7 Responses Jul 6, 2015

    Caught By My Sister

    I was 14 and just started crossdressing. I snuck into my sisters(she was 18) room while i was home alone. My sister was out witu her friends and my parents were at work. I stole some panties a bra a couple of her dance outfits (very colorful with dimonds and sparkles) and a...
    ttttt56789 ttttt56789
    22-25, M
    7 Responses Jan 4, 2013

    Great day out to the shops,

    walking round in my clothes and trying on dresses was great :)
    anonimousguy anonimousguy
    16-17, M
    1 Response Apr 5

    When i was in 9th standard at

    that time first time i was attracted to my mothers clothes. My mom is working woman so all day she was out for her job. In this i saw my mothers kurti and legging lying on bed i like it. White kurta and red leggings. She used to ask me that this will look good on her or else she...
    ravipar ravipar
    26-30, T
    1 Response Apr 7

    one of them had to notice!

    i walk before i go to work in the morning. lately i have been wearing women's shiny leggings with leopard print or fishnet pantyhose underneath. man clothes on my upper half. some hose shows.but this morning i was feeling a little braver. i was wearing leopard print pantyhose...
    sbjj sbjj
    56-60, T
    1 Response Jan 21

    I've become rather open to my family

    and friends about my crossdressing. Labor day weekend I was attending a family reunion. I was bent over and my panties were showing, when my one and only male cousin put his hand on my back and said" I think I have those same panties!". After an awkward snicker. We discovered...
    Phxpaulena Phxpaulena
    61-65, M
    14 Responses Oct 10, 2014

    well 2 years ago for Halloween right

    before a party I had no costume ideas, with my girlfriend knowing im a crossdressing fanatic her and her friend suggested I dress as a classy women. I think in my head perfect! i agreed in a snap of a finger just like any other crossdresser would do. my girlfriends friend sam...
    crossdresserfun crossdresserfun
    22-25, T
    2 Responses Feb 5

    So I had always been dressing

    whenever my parents would leave and run errands. So every time they left the house I would race into my moms room and immediately throw on a dress. Well this day went a little different, I was left home like usual but also was in charge of babysitting my younger sister who was 5...
    lcd6993 lcd6993
    22-25
    4 Responses Feb 4

    Caught By Mom

    I Have been a cd since 9.I was never caught until i was 17. Its my first story over here so it may seem boring but anyway.I used to steal my sister bra panties an all that stuff &wore secretly.One day mom dad an my sis went to my aunt's for weekend.I refused coz i had planned...
    katiegorgeouss katiegorgeouss
    18-21, M
    20 Responses Sep 3, 2012

    Ooh la la..... ....a very close call

    for a very French maid: 100% True Story: When I was 21 and at university I shared a flat with one male friend. He had no idea that I was a crossdresser. Anyway he had gone away for the weekend....I had done all my prep....legs and body shaved...moisturised....and my chosen...
    chloetrans1117 chloetrans1117
    31-35, M
    13 Responses Dec 27, 2013

    my exwife came home one evening from her

    sister's house and caught me wearing her satin night gown, and her workout tights. i stood up, and turned around, she kicked me so hard in the balls i thought she ruptured me. she left for the night, and i think she went to her b/f house. i was layed out for a half hour or so...
    deleted deleted
    26-30
    5 Responses Mar 5

    I had always had a strange feeling

    that I wanted to dress the same way as my sister, I longed to wear a dress like hers, but didn't dare say anything. One day I found myself alone in the house, mum was working late and wasn't expected to be home for several hours, and my sister was away on a school holiday, so...
    02hamster02 02hamster02
    18-21, F
    7 Responses Oct 7, 2015

    I was married to Debbie

    for 20 years and we had some great times but after working away for long periods we drifted apart and were divorced all of our married life I had hidden the fact or so I thought that I cross dressed. At every opportunity I would where her clothes and buy my own meet people on...
    deleted deleted
    26-30
    7 Responses Sep 5, 2015

    so you know the story of the new guy next door

    ok so today I come out to get the newspaper in a white t-shirt and panties to tease him because he getting back from his run and he tells me hey sexy let me hit the shower than why don't you come over in about a hour or two to have lunch I giggle and blushes cutely ok...
    gueenemma418 gueenemma418
    22-25, T
    2 Responses Apr 14

    When I go out crossdressing I try to look

    attractive yet fit in. Normally I go grocery shopping on Friday's around 5 pm. I noticed many women wearing business suits most likely shopping after work. As a new experience I decided to do my grocery shopping en femme. Even though I can usually pass I try not to talk too...
    Stephaniegirl226 Stephaniegirl226
    41-45, T
    4 Responses Jan 22

    I just got caught. Really caught by my wife!

    This morning my wife had to go out and I arranged to follow on and meet her in an hour. This was a perfect opportunity to put on some girly clothes. So I went and Put on a pair of tight purple panties, Wolford 10 tights, an old bra, some B cup prosthetic breasts, a red bodycon...
    deleted deleted
    26-30
    10 Responses Jan 11, 2015

    so my wife already knows I dress,

    and I have been doing it openly with her for a few years now. Well a few nights ago my daughter came downstairs and caught me in my wig and no makeup but didn't know it was me lol. tonight though she came down and I was all done up but she only saw me from the back and said...
    deleted deleted
    26-30
    9 Responses Mar 1, 2015

    The one time I was ever caught crossdressing

    was by my grandmother! I was in my sisters room wearing my favorite bra and panties when I heard someone reach the top of the stairs! In panic I ran to my room, my grandmother was there and got to see me in my crossdressing glory! Luckily weeks earlier I told her about my cross...
    MelissaCDr MelissaCDr
    18-21, T
    4 Responses May 27, 2015

    One time I was caught by my dad

    when I was crossdressed. I had been laid off the day before from my job. I spent the morning in the macho mood. I had gotten up early to put in job applications and to get the word out that I was looking for employment. I put in several applications and spent hours talking to...
    Thejannettearmet Thejannettearmet
    51-55, T
    2 Responses Apr 3

    Was caught this morning by my 70year old

    neighbor he come around the house I was sitting in the patio he coughed I looked up reading paper and drinking coffee .i was wearing a light gray skirt nude pantyhose black sweater top his look was some disguised and awkwardness. He wanted to use some tools in my workshop he...
    lvrofhose lvrofhose
    56-60, M
    2 Responses Apr 19

    I had been getting dressed every time I was

    home by myself. I always had a day off during the week and my wife worked a normal work week. So there was all dressed up in my favorite skirt and blouse with black pantyhose and knee high boots, when I heard the garage for open. My heart stopped and I ran I to the bathroom to...
    silknrachel silknrachel
    31-35, M
    3 Responses Feb 2

    This is somewhat of a different way of getting

    caught. I buy my cosmetics at my local drug store. It is nice because they have a self checkout line, and for a closet crossdresser like me, it is a fast and discreet way to get my makeups. So a few days ago I went and resupply my cosmetics. Not only did I resupply...
    andreatcial andreatcial
    26-30, M
    3 Responses Jan 28

    Hi all I don't know

    if anyone notice. A few days ago I dressed as I do often. I fell asleep with eye shadow on the next morning I looked in the mirror. Oops I still had it on. I talked to a few people but I had sunglasses on. Don't think anyone knows
    Christymariegirl Christymariegirl
    51-55, M
    5 Responses Mar 16

    When I was eleven I went outside to pick up the

    newspaper for my mom. It was early in the morning and I went out wearing my baby doll pjs. Even though it was barely dawn, the neighbor lady next door was out in her house coat and the neighbor across the street was fetching his paper in his pajamas. We all just smiled at...
    Bobbie1952 Bobbie1952
    61-65, M
    2 Responses Apr 6

    A doctor of mine and me finally went out on a

    date. I knew she was bisexual and she had broken up with her girlfriend of several years. She knew that I often wore panties if not more. I am incontinent of the bladder too. I had flashed her my panties during many appointments. She commented positively about a couple of pairs...
    Thejannettearmet Thejannettearmet
    51-55, T
    Apr 6

    As the new work week started,

    it was time to put Kimberly away for a few hours. As I got up, I looked in the mirror, barely recognizing my male face, I decided to do something entirely out of the ordinary and pretty brazenly. Since my family was out of town, I decided I would wear panties instead of my...
    crosskimmy crosskimmy
    31-35
    6 Responses Jun 25, 2015

    Not sure if it's crossdressing

    but got caught wearing red nail polish on my toes I was at school and I thought no one would notice but in pe we were doing gymnastics. And I had to take my socks off I had to suck it up and just show it. I still do my toes and now my nails and get them out at school
    EvaMarie1406 EvaMarie1406
    22-25, F
    Jan 23

    Thanks E P. As long as you are remembered you

    will never ever be forgotten. 😇
    isacallandra isacallandra
    26-30, T
    Apr 20

    My fiance and I have moved to a place out in

    the undeveloped countryside of Florida. We were sitting in our living room drinking coffee and reading, with the curtains open, when our neighbor walked by. It was a little chilly, so, I was wearing silk women's pj bottoms, a short slip that I has slept in, and a lacy white...
    feelsogd feelsogd
    66-70, M
    3 Responses Apr 12

    Surprise surprise. ..

    . I had a meeting to attend yesterday in Des Moines IA. It was just in the afternoon so I drove up and back the same day.  I got dressed in my man clothes but put on panties and thigh highs. The plan was to wear a pair of heels to drive to and from the meeting.  I left the...
    cdjo cdjo
    41-45, M
    18 Responses Apr 15, 2014
More Stories