I Almost Caught Crossdressing

Personal Stories, Advice, and Support 861 People

    Today I went to the thrift store to find some

    shoes and clothes underdressed with panties and pantyhose. It's becoming one of my favorite things to do. Anyway. I saw my coworker walking in with her boyfriend just in time for me to evade her and duck out so I could wait in my car until she left. And to think I she could have...
    CDMichelle16 CDMichelle16
    2 Responses Apr 12, 2016

    I want to get caught cross dressing should I

    wear a bra and pink panties to my next massage and let her see my bra line and feel my sissy panties?
    Cdpantygurl Cdpantygurl
    26-30, T
    5 Responses Feb 14, 2016

    I have been caught a couple times.

    My wife caught me sneaking in the house one night. I worked nights at the time but it was hours after my shift had ended. When I got done working I changed, put on make up went to an ABS where I misbehaved. She was surprised and then not to happy. She then questioned me about...
    chrissyk48 chrissyk48
    46-50, M
    1 Response Aug 31, 2015

    I was almost caught many times

    but then I DID get caught and she was ok with it and now I wear panties only
    Mmorris352003 Mmorris352003
    1 Response Jan 8, 2015

    Yesterday the sister in law came around 2 pick

    summit up she left so I went and put my leggings on and knew nothing more then she came bk in 2 get her glasses I just sat and watched telly moved so she didn't see the leggings then she left didn't even look at me so glad her glasses where on the table. God knows what she would...
    24chris24 24chris24
    26-30, T
    1 Response Aug 29, 2014

    Right now I am sitting in my office wearing

    only my nightie as I do every morning. My office is detached from the house and I thought I just heard a car door close. I walk out the door and to my shock my son just stopped by for whatever reason. ****! I just locked the door and I hope he leaves without wanting to talk...
    silkydrawers silkydrawers
    2 Responses Aug 9, 2014


    At 12, my mom allowed me to dress at home. Every after school, I always hurry to went home to shower and change from my schoolboy uniform into my girl clothes. I alternately wear dress or a blouse and skirt at home. One Friday afternoon before we went home, our teacher told us...
    sharinep sharinep
    26-30, T
    9 Responses Jul 11, 2013

    I was a my friend's place

    and were playing in the pool with his younger sister. We may had 14 and her 12 at the time. I got into the bathroom after she went to change and the swimsuit was there hanging soaking wet. It was a vintage one piece front zipper body glove like on the picture and I had this urge...
    Uphilthis Uphilthis
    41-45, M
    1 Response Aug 5, 2015

    I worked as an electronics tech at a company

    that serviced industrial equipment. The shop was closed weekends but one of the techs was assigned to be at the shop to handle emergencies. The entire building normally was deserted. Usually! My turn came up to be the weekend tech. I was well into cross-dressing and I got the...
    ronna2 ronna2
    70+, T
    1 Response Nov 14, 2015

    when i was 15 i had the house to myself

    for most of a day so i went into my sisters room and got my faverite skirt and blouse with a matching bra and pantie set. graped a pair of 4 inch heels then got the pantie hose i had baught for myself. with all this in hand i went into the bathroom and showerd and shaved what...
    spaz1177 spaz1177
    46-50, T
    1 Response Dec 19, 2013

    Just some background information; I am a 14

    year old boy, I'm quite tall and I have a slight build. I also do karate and have pretty quick reactions, also tonight we had some friends over for tea/dinner/whatever other people call tea. Boys underpants are awful and uncomfortable and stupid so I decided to wear some black...
    Shadowknightt Shadowknightt
    16-17, M
    1 Response Nov 28, 2015

    As I was literally hitting post telling about

    my first experience wearing ladies jeans in public. I didn't have courage to wear more than that. Though I did have black heels and a cute top in the car IF I felt brave enough. I didn't. So I get home feeling exhilarated from my experience. I throw on my heels and top. I...
    CDpantyman CDpantyman
    31-35, M
    2 Responses Feb 16, 2015

    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
    4 Responses Dec 27, 2013

    The cleaning lady (Charlotte) comes to the

    house weekly, and irons my shirts that I leave out, normally 5 shirts for the week ahead. However, today there were only 4 shirts, so Charlotte went to my wardrobe to see if any more shirts were in the cupboard. In my wardrobe are ~5 skirts, ~4 dresses, in one corner of the rack...
    imogentranny imogentranny
    36-40, F
    1 Response Feb 6, 2014

    I was at home alone and I decided to dress up

    like everyday. So I was wearing some black and pink lingerie and a golden fishnet garterbelt, and a pair of sexy black 4 inches heels boots, when I heared my mother's car. I didn't expect that because it was too early. I didn't know what to do so I locked the main door and I ran...
    ImasexyCD ImasexyCD
    16-17, M
    3 Responses Jun 28, 2015

    i was wearing a bra with stuffing in the cups,

    under my loose fitting rugby shirt, when i had to answer the door to the mail lady, (i had to sign for the package,) i didn't think of what i had on, i just opened the door and signed, the young lady looked at me then my chest then bashfully looked down, i at the time had...
    cee174 cee174
    56-60, M
    2 Responses Dec 12, 2015

    I have been caught or almost caught many,

    many times in my life and yesterday Jan. 9 2015 was the first time for this year. I wasn't exactly caught but nun the less an embarrassing moment. It was 6:00am and as usual I was in my office on EP and wearing a negligee with multi layers. I was shocked when I heard a...
    silkydrawers silkydrawers
    10 Responses Jan 10, 2015

    This was a very close call by seconds.

    I remember one night that my sister was out with friends till really late. It was my chance to raid her dresser. I would frequently make trips into her room and since her room was right across from mine. Except it was in the front of the house so I could see if anyone was...
    banannasplitz09 banannasplitz09
    26-30, M
    1 Response Jul 31, 2014

    I was a teen. My sister was at a friends

    and my parents went out for the night. Or so I thought. When they left I didy run through my sister drawers and closet and dressed up sexy. My hair was long as was the fashion and I just brushed it out into a girls style. I put on a pair of my others heels and went downstairs to...
    Lyndaloves1957 Lyndaloves1957
    56-60, T
    8 Responses Nov 5, 2014

    My heart is still pumping.

    I was so scared and still am to be honest. I was also very lucky. My Mum and Dad go to work and my bro goes to my dads office. I get to stay at home and it's great. I get to stay at home and do what ever I want. Earlier today I went into town to get some makeup (I can't...
    deleted deleted
    1 Response Aug 25, 2015

    The first time I was caught by my wife

    when I was sneaking in the house late one night after enjoying myself at the adult theater. She was quite surprised but releived as well as she thought I was having an affair with another woman. I was horrified when I was pulled over by the police not once but twice. The second...
    chrissyk48 chrissyk48
    46-50, M
    2 Responses Feb 14, 2016

    Almost Caught

    when inwas younger i always sneek into moms drawers and find some sexy lingiere and grab them and go back to my room and get dressed. i remember how exciting it felt to be dressed in such silky items. well this one day i snuck into her room grabbed a sexy black teddy and matching...
    deleted deleted
    2 Responses Jan 24, 2013

    Grocery Shopping Close Call

    My parents had went to the grocery store so I was home alone free to crossdress. I got dressed in all of my moms dresses taking pictures. About 45 min. later I had on stockings, a pair of pink panties, a red lacey bra, a floral skirt, and a red top. I felt so great in my clothes...
    tripperCD2 tripperCD2
    18-21, M
    Aug 12, 2013

    So this is how I got my leather corset I was in

    the middle of gathering up my fresh clean regular every day man clothes my clothes are in a net hamper and I see a small package and my first thought oh no they're on to me so I rushed upstairs to my bedroom and locked the door I'm a private crossdresser so I only feel safe in...
    deleted deleted
    2 Responses Jun 2, 2015

    I started with my sister's panties,

    nylons and such. One day, when I was about 16, I had on a bikini and nylons. I was in my bedroom enjoying it all, lying on the bed, when my sister walked in. I rolled off the bed. She asked "what are you doing." I replied I was getting dressed. She turned and walked out...
    1della 1della
    51-55, T
    2 Responses Oct 31, 2015

    hmm don't want to retype.

    posted my naughty life in I love getting caught will update there as stuff happens
    deleted deleted
    Mar 21, 2016

    Sometimes is difficult to be a crossdresser

    if you don't want family to think the opposite of who you really are underneath the average regular guy clothes
    deleted deleted
    1 Response Jun 2, 2015

    There have been more then a few times

    where my mom has found my panties or other pieces of my girl clothing lying around my room and has asked me about it.
    deleted deleted
    1 Response Nov 7, 2015

    It was a couple months ago.

    I was in my room wearing woman's jeans and my sister walked in. Luckily, I jumped right into my bed and pulled my blanket over me, and she thought she just scared me.
    LanelJaento LanelJaento
    16-17, T
    Dec 13, 2015

    Today my mom had to work till late

    so I decided to dress up I put on my moms bra and dress and some chunky heeled flip flops and a blond wig I was in the bathroom trying to decide on wether or not to put on makeup then I heard the front door open it was dad coming home I shut the door and locked it luckily he...
    Flash123456 Flash123456
    18-21, T
    1 Response Oct 1, 2015

    When I was a young boy my grandmother used to

    read me books at bedtime, one night I had decided I was going to put a bra on, I had the panties hidden between the mattress I was laying on. I had thought that was an expert hiding spot, no so much as I was soon going to find out. I was laying in bed having the story read to me...
    Cdpantygurl Cdpantygurl
    26-30, T
    3 Responses Mar 14, 2014

    I've almost been caught once

    and it was really a close call. Had I been thinking more clearly that day I probably would have done things differently. Here's the story. My parents had been staying with me for about a month when it happened. They had sold their house and was in the process of buying another...
    deadpool7 deadpool7
    31-35, M
    2 Responses Jan 3, 2014

    I'll share my second experience.

    I was sitting at the table, reading the paper, nobody is supposed to be home, so I was wearing a sports bra (nothing more) and my jeans, simply reading the paper when I heard a key in the door, and the door open. My roommate is home. Crap. He went to the left of the closet...
    1della 1della
    51-55, T
    Nov 5, 2015

    I have to share this story of something

    that just happened to me.It's a very hot summer night and I couldn't sleep. I ventured out and sat by the pool wearing my nightie. The moon was bright and just overhead. Just for fun I decided to climb the ladder of the pool slide and sit on top of the slide. A wonderful feeling...
    silkydrawers silkydrawers
    2 Responses Sep 6, 2015

    Almost Caught My Mother

    I still live at home, and my wonderful mother does my washing, so i am very careful abut what i put in obviously, on this day though i just grabbed a pile of clothes and chucked them in the wash with out checking. The next day when i woke up my mum asked me if i knew anything...
    CDSabrinaSwann CDSabrinaSwann
    26-30, M
    3 Responses Apr 27, 2013

    well this happened about a year ago,

    it was about 11 pm and the rest of my family was asleep, so I decide to crack open my "hidden stash" some light brown heels with suede socks and laces, a corset/suspender set and a black mini dress and went down stairs. I started walking up and down the kitchen and living room...
    deleted deleted
    5 Responses Apr 7, 2015
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