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I Was Caught Wearing Girls Clothes

Personal Stories, Advice, and Support 1,682 People

    When I was about 14, my mom caught me dressed

    in her bra and panties. She didn't take it very well. She was very upset, but never said any thing else about it. She had found my stash before, so I don't think it really surprised her, just having her suspicions confirmed upset her.
    mandywantsit mandywantsit
    56-60, M
    4 Responses Feb 19, 2015

    Began Looking Like Mother And Aunt.

    My crossdressing began like so many other's at a very young age and by wearing my mother's clothes. I was caught many times and after a while she simply looked the other way and that amounted to tacit approval. Seeing her things were a bit too big for me, once I realized how...
    josilv josilv
    3 Responses Oct 3, 2011

    In the summer of 1946,

    when i was 5 or 6 my mom decided to put girls panties on me, and short pants. I told her someone may see the panties, she said that will probably not happen, she sent me outside to play with my friends, i was wrestling around with another boy and he happened to look up my shorts...
    gwhizzers2 gwhizzers2
    70+, T
    1 Response Apr 14, 2016

    The Mail Lady

    When I was 13 I had gone out on halloween as a girl. My mother and girlfriend Cheryl had bought me several dresses to wear. I had alot of fun dressingup and being one of the girls with my mother and Cheryl. It became a routine for me, not on a daily basis. One day in the spring I...
    RobinLeade RobinLeade
    5 Responses Aug 19, 2011

    Caught Again

    It was a nice pleasant evening so I went up the hill in my car and as it was quite dark I picked up Ken and we went for a drive up the hill.I was just wearing stockings heels suspender belt bra with a mini skirt and no knickers as I like to feel the ***** running down my legs...
    lucy1000 lucy1000
    56-60, M
    12 Responses Oct 30, 2012

    Uh Oh

    One day when I was 16 my parents left home to go drop my sister off at college in Georgia. I saw this as the perfect opportunity to crossdress since the baby sitter only came a few times a day. So the minute they left I went to my stash of my sisters clothes I put on a sexy black...
    Loverb0y Loverb0y
    22-25, M
    Nov 20, 2012

    Mom Caught Me In Her Bra And Panties

    When I was about 7 years old, I became fascinated by my mom’s sexy underwear. While she was doing chores or getting ready to go out or to work she often wore just a robe over her bra and panties and sometimes when it was warm in the house just her bra and panties all around the...
    barbarascampbell barbarascampbell
    41-45, T
    6 Responses Jun 11, 2011

    Well I never got caught yet

    but I started when I was like 8 when I saw girls underwear just laying on the floor so I got them and tryed them on they felt good and today I still wear girls underwear just off and on and I wear them at night time always
    Masontaylor167 Masontaylor167
    22-25, M
    Apr 28, 2015

    My Two Step Sisters.

    They love dressing me up and playing with me, their both really sexy. The only time I get to see them naked is when their wearing stapons ready to play with me lol.
    girlydimpale girlydimpale
    18-21, M
    3 Responses Sep 30, 2012

    Panties = Penis

    It all started at school I was wearing panties and little did I know we were going swimming today and I had to change with another boy, when we got there we were sent to the changing rooms and I was so scared of what was going to happen we got in the changing room and the other...
    jamiecarter jamiecarter
    Sep 23, 2012


    I remeber i was 12 years old and had put on the tights of my momwhen she wasnt home, so i felt so great that i went to her closet again and put on a mini skirt and a bra and her blouse, i felt soo amazing.. but an half an hour later my mom came home, i started to hide cus i was...
    GirlyBoyy GirlyBoyy
    18-21, F
    1 Response Nov 23, 2012

    Sisters Catches Me Dressed

    I have been secretly wearing my sister 's clothes since my early teens, and have always had the thought of what a thrill it would be to get caught! Well a recent summer saw my parents go away for a couple of weeks on holiday. Me and my sister stayed at home, however she was dog...
    20nik 20nik
    18-21, M
    29 Responses May 9, 2012


    i was in Junior high school (13 years old) and was home after school alone. It was a spring day, so i ******** down and was running around the house naked with a huge hard on. Back then, I was probably 5'6" and weighed 110 pounds. i found myself up in my mom's bureau...
    Slimbidude Slimbidude
    46-50, M
    3 Responses Apr 22, 2013

    Caught Wearing Girl'S Clothes

    I was dressed in girls clothes and went shopping at J C Penneys. I don't pass but I was having too much fun. I walked by the intimate apparel department and decided I wanted a bra fit. I asked one of the sales associates and she agreeded. She was fitting a young teenage girl...
    jml2000 jml2000
    61-65, M
    5 Responses May 16, 2013

    Caught At School By Gym/science Teacher Part 1

    it all started when my 15 year old sister caught me wearing her panties. It was a friday after school i was home and my sister was at cheerleading practice well i went to do what i usally do on a friday wear my sisters clothes. so i went to her room and put on a pink sports bra...
    jonathan2323 jonathan2323
    22-25, T
    3 Responses Dec 10, 2011

    She Finally Caught Me.

    During this time was when I was getting alot of my cding done.  As my mom was spending alot of time with her new boyfriend.  So I got alot of dressing time in.  Which was nice as I was going next door to our neighbors every now and then and having my fem fantasys...
    pantyhoseslut pantyhoseslut
    22-25, M
    44 Responses Nov 29, 2009

    First Few Times

    1st time caught , I wasn't dressed. My parents found my stash hidden in my closet. After they blew up, they took everything and locked it in their closet till I moved out on my own. They never really accepted that part of me and it was never mentioned. 2nd time I was dressed...
    ve5wil ve5wil
    36-40, M
    2 Responses Oct 9, 2013

    By My Friends Wife

    She always suspected that i fancied her husband and that he was bi as well but nothing prepared her for this. We had been seeing each other for a while and i had told him i liked to be girlie. He loved it when i dressed up for him and sucked his big ****. This time as just a...
    vicky71x vicky71x
    36-40, T
    6 Responses Sep 29, 2009

    I'm still in highschool (senior)

    and I was coming back from visiting my sister in college. halfway back to my house I changed into some yoga pants. an hour later I pulled off on a diet road to go to the bathroom... and locked my keys in the car. I had to call my mom and have bring her say of keys. when she saw...
    OoljeeAtsa OoljeeAtsa
    26-30, M
    Aug 25, 2015

    Asked To Baby Sit For Neighbour

    I was 17 and my neighbour wanted to go out with the girls. She was a single mum of one so I said I would do it for her. My neighbour was really fit she was 6th tall slim build very good looking for 32. Her kid was put to bed before I got there I knocked on the door and was...
    Reddevils56 Reddevils56
    31-35, M
    2 Responses Jun 12, 2012

    HOW IT STARTED--When I was around 6

    or 7 my dad split and left my mom in bad shape. After a while mom and me had to move in with moms aunt sherry. Sherry was a classy lady she owned a beauty salon and told my mom she would teach her and give her a job there. By the time I was 12 and being around women dressing and...
    samanth38 samanth38
    Oct 28, 2014

    High Heels and Hot Pants

    It happened when I was still living at my parents. They went away for the weekend so I dressed myself up. on the saturday morning I came down stairs wearing my high heeled knee high boots, hot pants and tight strappy top. To my suprise when I opened the bathroom door there was my...
    Heellover Heellover
    36-40, M
    8 Responses Aug 3, 2009

    Caught Wearing Stockings And A Skirt

    I used to go to my best friends house and always wore my stockings we were sat in his lounge drinking and after a while I had to go to the loo so I went out in the hallway just wearing my stockings and high heels and went to the loo. I played with myself while I was in there and...
    lucy1000 lucy1000
    56-60, M
    3 Responses Sep 11, 2012

    Cristina's Sissy-*****

    My step sisster had tons of clothes laying around her room, and me I just loving stealing some and sleeping in them. I love wearing her tight panties all the time. She wasn't dumb though she knew for days that I've been taking her clothes because they were always misplace and she...
    girlydimpale girlydimpale
    18-21, M
    14 Responses Aug 18, 2012

    There I was fully dressed,

    made up, hair styled and sprayed in place, nails polished brightly, and enticingly perfumed when I heard the door open. The maid was here to straighten the room up. She looked at me and smirked a bit but never said a word as she asked if I needed anything and that she'd be back...
    amandatrane1 amandatrane1
    51-55, T
    Dec 12, 2015

    Caught By Mom's Friends

    This is a hard story to tell never shared it with anyone!! I was about 13yrs old. My mom had a couple of her friends over. I went to my room to "play" always dressed from head to toe! To be safe I closed my bedroom door tight. The first time I had done that. My hair was long so...
    christypvcsissy christypvcsissy
    36-40, T
    9 Responses Mar 28, 2011

    Petticoated Paradise Lost

    After all the close calls growing up, wearing a half slip in bed and mom wanting to pull the covers down, and so forth, I finally was caught. And it really wasn't my fault., as you will see. I was traveling on business in Durham, North Carolina and had some down time, so I went...
    Kim1girl Kim1girl
    61-65, T
    21 Responses Mar 10, 2013

    I Caught Wearing Girls Clothes.

    When i was a boy 10 years old i started wearing girls clothes then in my bedroom my brother seen my in a dress, wig, patyhose, and high heels i was so excited to try dresses, panties, pantyhose they fit me perfectly so i hesitated to take them off so i continued to wear them i...
    Princess1137 Princess1137
    1 Response Jan 18, 2013
    michellewpantys michellewpantys
    Nov 14, 2015

    Oops Payback

    I was about 6 or 7 when my mom saw me putting on peds (nylon socks) and said I looked cute. So I didn't think any thing about it until my dad saw me in them. Then commented if he sees me wearing them again he would dress me like a girl from head to toe and even my hair, and go to...
    boomer58 boomer58
    7 Responses Jan 20, 2013

    Caught In The Woods

    I was caught when I was out in the woods by my house when I was 15. I went back there wearing a pair of pantyhose under a pair of tight silky pink running shorts. I also had on a pink spaghetti strap tank top on with a bra underneth the shirt with two nerf like baseballs to fill...
    der12333 der12333
    36-40, M
    26 Responses Aug 6, 2010

    Caught By Mom

    One day when everyone was gone I went into my moms room and put on her bra and thong. Then I went into my sisters room and put on her yoga pants. Right when I was taking them off my mom walked in. She asked what I was doing and I just said I like wearing girl clothes. She then...
    deleted deleted
    6 Responses Oct 20, 2012

    When I was 13 My friends sister was wearing

    these really cute short shorts all day and I was looking at here cute ***, and later that night him and his sister came over to swim and when they left I was bringing the towels in and I found her shorts. I ran inside, went up to my room and started sniffing them while...
    Lucas530 Lucas530
    Apr 1, 2016

    Caught In Terror

    I will start out telling that this is a true story, happened yesterday morning. It was about 9am and I was still in my sleepwear lounging around without a care in the world. I was wearing a nice but conservative floor length chocolate brown nite gown ,white bra and honey color...
    squeekers2 squeekers2
    61-65, M
    Apr 30, 2013

    Caught By My Neighbor Part 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
    14 Responses May 2, 2011


    When I was twelve, and at the same school as my sister, she asked me to take home her uniform as she intended to go out with her friends. As it was a two mile hike home I took a shortcut through the woods. Whilst there, I thought that as I have my sisters clothes with me I could...
    moragh moragh
    51-55, M
    2 Responses Mar 9, 2012


    My wife and I just returned from Walmart where the sales girl noticed my pantyhose, thong and then my bra. My wife was in the grocery department, while I was shopping in the women's wear department. I had just come out of the bath room and my outer shirt was caught up, it wasn...
    sherrynpantyhose2k4 sherrynpantyhose2k4
    51-55, T
    25 Responses Aug 10, 2011

    I was caught at school

    when I was in the 3rd grade, 9 or 10 years old. I had a few panties that my Mom bought me when I was 7 so I would stop wearing hers. I happened to be wearing just plain pink panties this particular day. And I am sure all you remember when you were inn school at that age that the...
    Michelle1976 Michelle1976
    41-45, T
    1 Response Mar 28, 2015

    My Cousins Outfits

    ever since i can remember i've always liked to wear girls clothes. one day when i was 15, i was at my aunts house to help do some chores and the family left to go to the county fair. i said i didn't want to go and wanted to finish what i was doing. that was fine with them so they...
    valtv valtv
    22-25, T
    4 Responses May 21, 2009


    I was alone at home dressing up, when i was putting up my make-up.. i heared the door bell ring, and knocking on the window next to my door, i checked really quick, it was my grandmother who was standing there looking to see anyone in the house, she didnt see anything so she...
    GirlyBoyy GirlyBoyy
    18-21, F
    Nov 24, 2012

    I was at my sisters room trying on her dress

    and skirt when she walked in and said hi sis. I said dont tell anyone. She said on one condition let me and my friends dress u up andu have to hang with us wearing those clothes sometimes
    dalonelyone dalonelyone
    5 Responses Jun 30, 2014

    Caught By My Neighbor Part 1

    Before I left my Moms house to live on my own I used to watch our neighbors house for them when they went away on vacation. My Mom would send me over to the house to make sure that everything was alright inside, and that the heat was on, and so fourth. One day as my Mom was going...
    allwrappedupinit allwrappedupinit
    51-55, M
    10 Responses May 2, 2011


    I wasnt caught wear clothes but one day wen i was younger, I was just painting my nail. I really love to paint my toes mostly because only I can have them painted in public without anyone seeing. Well any way i was just doing my normal routine waiting until my family went to...
    Dyboy44 Dyboy44
    31-35, M
    Sep 11, 2013

    Birthday Supprise

    It was my birthday and i only had to work half a day. my wife new that i would be be home around noon. when i got home my wife met me at the door and told me to shower and shave as she had supprise for me. i took my shower and shaved my entire body. when i got out she had some...
    DeeDee1966 DeeDee1966
    41-45, T
    15 Responses Nov 14, 2009

    It was a day where no one was home

    but me. My mom dad and sister were all away. My cousin at work. I decided that I had to go try on some girl clothes I went into my cousins room picked out a pair of panties and a skirt then went to my sisters room to change. After changing it was one of the best feelings ever...
    Kens214 Kens214
    31-35, M
    Jul 15, 2014

    Caught By Czn And Pay F0r It !!

    when i was 13 i was n0t get permission from my mother to crossdress fully i used t0 dress secretly.. one day my mother and sisters were not at home they g0 for shopping and i was alone at home my mother said to my czn to look after me that she was g0ing... it was great chance f...
    lesban lesban
    18-21, M
    1 Response Oct 2, 2012

    The Land Lady And Me

    I was in my 20’s and living with an older woman as a lodger. She was a nurse with a two bedroom flat and I had the tiny “box” room. When she was away for weekends etc it was great as I had the run of the place and it was the first time that I didn’t have...
    SusanMarina SusanMarina
    9 Responses Feb 13, 2010

    I had a girl roommate

    and I would sneak her clothing. I used to like to wear her panties while she was having sex. Anyways, I thought she was spending the night with some dude. Well she didn't spend all night and caught me in skirt. She walked in the house and I was watching TV.
    Therealjason Therealjason
    31-35, F
    Jan 6, 2015

    I Thought Id Share This

    I am sure most of us have been caught wearing girls clothes as i have on numerous occasions the first being when i was 8 by my mother who freaked out and told me little boys dont wear heels. Anyway i thought i would tell you about the time i was caught by a friends wife. It was...
    louisetv louisetv
    12 Responses Mar 5, 2009
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