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I Was Caught Wearing A Bra

Personal Stories, Advice, and Support 170 People

    The Next Time

    My son 40 years old was doing some remodeling in our house. My wife was away on vacation. Iwas sitting in front of my laptop just surfing. I had the door to our bedroom closed but not locked. All of the sudden the door pops open and in comes my son. I am sitting here in...
    gneena gneena 70+, F 3 Responses Apr 15, 2010

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    Almost Caught Wearing Breast Pumps In Public

    Today, I was almost caught in the street wearing breast pumps under a bra! This must rate as one of the kinkier cross-dressing stories, but here it is. I love to wear a bra, but even more, I love to have my nipples sucked. To encourage “sissy suckers” and make myself bigger...
    vastsea vastsea 31-35, T 3 Responses May 12, 2013

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    Andy Caught Wearing A Bra

    Hi my name is andy s. I have been a cross dresser since I was 6. I hid this passion for womens clothes till I was caught wearing a bra by a girl.who had a crush on me in high school. Her name was Melissa , and she taunted me for years till I had a nervous breakdown . Melissa w...
    Seggie18 Seggie18 31-35 Jun 9, 2012

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    Caught

    I was in a Lane Bryant store close to my house. I had on a lacy 44 D bra. I was looking to see if there were any that I did not have or want. When I am shopping I am like a hubcap. I go everywhere but see nothing. So I finished ad I had not chosen anything. I was about to leave...
    gneena gneena 70+, F 2 Responses Nov 24, 2009

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    I Was Caught At Work Wearing A Bra

    I wear a bra, panties and tights under my suit everyday for the past 5 years maybe longer. I was working on a big project at work and have been working closely with a female co worker for about 2 months now. We were good friends and started work at this company the same day...
    Keliegh Keliegh 41-45, M 1 Response Oct 8, 2012

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    I Have Worn Some Pretty Bras To Work, Previously Un-noticed.

    I have worn some pretty bras to work for the past ten years. Of course no one else ever noticed (well except for one middle aged woman about eight years ago, but that is another fun story). Well about three weeks ago I was working late in our construction trailer and was...
    dustywhitney dustywhitney 51-55, T 3 Responses Nov 24, 2012

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    Want To Be Caught In Bra

    The bigger my moobs get the more I love them! They feel so good in my tight bras and I love the feel to rub my nipples till they're hard and stand out in the bra. I too love the feeling to squeeze and cup my moobs and think how great it feels to have my nipples sucked till they...
    robbi95 robbi95 46-50, M Jul 16, 2011

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    Seen Wearing A Bra And Using Two Breast Pumps

    I have slowly been getting into cross-dressing, and until I found this site I thought it was actually quite daring merely to wear a bra and stockings in bed. Now, I don't just like to wear bras, I want to fill them with my own boobs and to be seen with the results in public. And...
    vastsea vastsea 31-35, T Apr 19, 2013

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    Related Experiences

    I was 15 and had been wearing pantyhose regularly by that time. My wearing was usually limited to the 45 minutes I had home alone between getting home from school and when my...
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    This is about the embarrassing moment I had during this weekend, visiting my girlfriend at her parents' house. But a little background info first. I have been with my girlfriend...
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    Cuffed and detained during the holiday season. I wasn't really caught in the act of crossdressing but I was caught with the clothes for crossdressing. I actually had told this...
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    I geuss first it was the cutest little white cotton and lace nighty about mid thigh length well i wasnt actually wearing it at the time, I used to keep it in the back of one of my...
    sadei sadei 31-35, F Aug 16

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    I was Caught Crossdressing by my next door nebor Guy and Im still doing it to day. I was in my Wifes We are the same size too. Well I was in her 34-C push up Bra, and Bikini...
    Kellyboy541 Kellyboy541 56-60, F 6 Responses 6 days ago

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    One time some friends of mine were over and we decided to play truth or dare. I was dared to ***** naked, jump the fence into my neighbors yard and stand on her back porch for 2...
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    I was caught by my auntie in her swimsuit in the bath when I was 14 I thought she was at work allday so I found one of her onepiece swimsuits slipped it on and got in the bath I...
    markwet markwet 46-50, M 2 days ago

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    This is a famous joke. Not true, but fun to repeat. Sam walked into the locker room to change into his softball uniform. The guys spotted the bra he was wearing and shouted "What...
    Robertredlips Robertredlips 56-60, M 4 days ago

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    I was home alone my GF was gone for the weekend so I took the opportunity to dress. I went and got a sports bra and suntan panty hose I put on a nice dress and some high heels, a...
    pmgurl pmgurl 51-55 1 Response Aug 16

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    I once fell asleep (druged) wearing a bra, top,panties, skirt, high heals, and panty hoes. And woke up on my stomach with my *** hanging of the side of my bed, my as* hole...
    bottomslut1 bottomslut1 18-21, M 2 Responses Aug 4

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    My best friend saw the bright blue thong I was wearing at his house... He told me to follow him inside we went to his mums room because nobody was home. He made me put on her blue...
    Pantyhoseboy1 Pantyhoseboy1 18-21, M 4 Responses Jul 27

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    I have just been caught with a nappy on by my 8 year old son and I don't how to explain to him that i like wearing nappies and him keeping my secret
    bigbabymark bigbabymark 41-45, M 4 Responses Jul 31

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    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...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 7 Responses a week ago

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    I have always wanted to get caught cross-dressing and be horribly humiliated. This story you are now reading is not true, but I am sharing it as if it was true: Last Friday night...
    Robertredlips Robertredlips 56-60, M 1 Response 12 hrs ago

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    I swiped my first pair of panties from a friends sister when I was 9. By the time I was 11, I had collected quite a few pairs from her and my cousins. I kept them in a shoe box...
    Bobbie1952 Bobbie1952 61-65, M 4 Responses Aug 7

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    Not many people know I wear woman's underwear. I got caught in a thong by a sales assistant at ann summers. Yesterday I went into ann summers and seen a white thong with...
    nikolas444 nikolas444 18-21, M 2 Responses 3 days ago

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    lacypantyboy lacypantyboy 26-30, M Aug 4

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    Relent34 Relent34 26-30, M Aug 6

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    The last time..? Maybe? So it's been a while since my last post (December) and I was thinking about coming out. Well, things took a hold of itself in it's own way and so much has...
    elliecarr elliecarr 18-21, T 6 Responses 4 days ago

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    When I was 17 my grandma caught me ************. And I was fully naked with nothing to cover up with. I've never shared this with anyone before.
    Lookingforadvice44 Lookingforadvice44 26-30, M 1 Response 6 days ago

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    I was staying the night with one of my friends in high school. He was down the hall in the bathroom and I was in his bedroom changing into pajamas. I was in my shorts just...
    Bobbie1952 Bobbie1952 61-65, M 1 Response Jul 30

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    When I bought the house I am in now. It needed some work before I moved in. I told the HOA that I would be moving in a month after I closed on the house. They told me the...
    deavesl708 deavesl708 51-55, M Jul 31

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    We had the wife of the couple we are best friends with, coming to stay with us for a few days while she was in town. We used to live a few miles from each other, but now we live...
    nytro44 nytro44 51-55, M 2 Responses Aug 5

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    This morning when my bro went to work he told me to stay home (cause I was at his house today) After he left my BFF called me and asked if I wanted to hangout. So I said yes cuz...
    Fifidog Fifidog 16-17, F Aug 7

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    Bobbie1952 Bobbie1952 61-65, M Aug 10

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    Bartimaues Bartimaues 31-35, M 1 Response Aug 11

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    I just had a very embarrassing moment. I was babysitting two little boys and their baby brother. The other boys were about 10. I was taking care of the baby when it threw up all...
    Becky7171 Becky7171 18-21, F 18 Responses 4 days ago

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    I'm 18 I was with my friends house for a swim. After we swim we go take shower one by one, I go for shower first after I shower I go into my friends room I didn't realize that you...
    kentlim00 kentlim00 13-15, M 1 Response Jul 27

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    I was at my sisters house at the time and I forgot to take off my green with pink dotted thong and she saw it over my jeans waist and she took all my underwear away and said if I...
    Pantyhoseboy1 Pantyhoseboy1 18-21, M 3 Responses Jul 28

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    My friend came over to my house and he went to my room I forgot to put my pink thong away and he asked if I wear it I told him yes and he asked if I fully dressed I once again said...
    Pantyhoseboy1 Pantyhoseboy1 18-21, M 3 Responses 3 days ago

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    I love dressing up on webcam and showing off or swapping pics with sexy girls
    69morninglory69 69morninglory69 26-30, M Jul 28

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    I like watch you rub your self daughter
    Daddylicksyou Daddylicksyou 61-65, M 1 Response Jul 29

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    My first time wearing pantyhose, was also the first time I got caught. Luckily, I was caught by my sister, as they were her hose I was wearing. I was 13 years old and had just put...
    pantyhoseguy7572 pantyhoseguy7572 41-45, M 4 Responses Aug 2

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    I have been crossdressing for a while now but the first time I was caught was when i was 10. I have a older sister that washed cloths with mine one morning, and she had her pink...
    Fogle3 Fogle3 16-17, M 4 Responses Jul 31

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    Back in elementary school, I used to steal many things.. minor things, but many lol. I'm talking people's pencils, gummy erasers, pencil grippers, pencil sharpners, etc. I had a...
    secretgal2 secretgal2 16-17, F 2 Responses Aug 17

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    I was caught and still get caught, at least I try. He peeps pretty often. i pretend I dont know. I since have moved my bed in front of the window, I keep the blinds adjusted so he...
    TheBeastsPenetratingBlade TheBeastsPenetratingBlade 18-21, F 14 Responses Aug 12

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    There was one time when I was home alone and I was caught naked by my neighbor. I was tanning in my backyard in my bikini and I decided I wanted to get rid of some tan lines so I...
    Kenzie123 Kenzie123 18-21, F 2 Responses 5 days ago

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    One time I was on the beach at a resort boogie boarding. The resort was laid out so that the hotel and pool were about a quarter of a mile away from the beach with the only access...
    deleted deleted 26-30 1 Response Jul 29

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    Many times. My brother was born in Branson and my dad was raised in the nearby town of Hollister.
    OzarksTrucker OzarksTrucker 36-40, M Aug 17