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I Was Caught Wearing A Bra

Personal Stories, Advice, and Support 170 People

    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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    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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    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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    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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    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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    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 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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    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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    Related Experiences

    I missed the mailman and needed a letter mailed. So I hopped into my car and drove to the post office. I was wearing a black bra with a oversized tank top and black shorts. It...
    meg1cdforyou meg1cdforyou 61-65, M 2 Responses Jul 13

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    The first time i was caught crossdressing i wad 16 and wearing high heals, fish net stockings, a short skirt, a small skimpy shirt and makeup on. The worst part is my mom caught me...
    bottomslut1 bottomslut1 18-21, M 2 Responses Jul 6

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    During the times I was walking around naked, I was caught and almost caught being naked. Couple times I was outside being naked and my dad would come home from work and I was dash...
    thisguyrocks thisguyrocks 22-25, M Jul 18

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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...
    Soccer127 Soccer127 18-21, M 10 hrs ago

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    I was caught by my Mom it was when I was about 8 we were having some friends over for a party. I snuck off and found my Mom's high heels and put them on and was admiring myself in...
    pmgurl pmgurl 51-55 4 Responses Jul 9

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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 2 hrs ago

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    I was 16 when she caught me wearing her panties and bra. I was in my room dressing up didn't know she came home and caught me she said you look cute let's go buy more
    LOVERPANTIES LOVERPANTIES 18-21, M 7 Responses Jul 20

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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 3 Responses 3 days ago

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    We'll this one time I was riding dirt bikes with with a friend of mine (girl) and we ened up at this river so we decide we would stop and chill for a min we got the bright idea to...
    ddavis21 ddavis21 18-21, M 3 Responses Jul 15

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    When I was about 16 I found my Mom's red lipstick and decided to put it on, thought I would only leave it on for a few min. I had it on and was doing some things in my room when a...
    pmgurl pmgurl 51-55 Jul 9

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    I went out being the guy i am i was wearing my sexy black dress and heels when i was in a shop i saw my friend who noticed me i ran like hell and he followed i hid but he told my...
    conankoller conankoller 22-25, M 3 Responses Jul 13

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    When I was 12 i realised a loved the feel of female clothing being a guy myself it was strange I knew my mum would freak if she found my out so in the end i decided to make my own...
    Crossdresserman Crossdresserman 22-25, M 4 Responses Jul 13

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    I was repeatedly caught skinny dipping as a child. It was in the local pool and being crazy as I am I just took off my bikini under water and swam nude. But the lifeguards didn't...
    Sanvis Sanvis 18-21, F 2 Responses Jul 12

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    This happen on June 10th 2014, my parents force me to brake up with my girlfriend (me and her don't consider are selfs broke. up) but my parents told me it was because "it was for...
    ECrierie ECrierie 16-17, M 1 Response Jul 10

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    Today my mum was at work and my brother and sister were asleep (for the whole day) so i decided to go through my mums cloths and i found the most beautiful see through silk dress...
    conankoller conankoller 22-25, M 4 Responses Jul 13

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    Last year my family were out from around 6pm to 7pm each Friday, so I thought I'd have some fun. I'd ***** naked, walk into my back garden and round the side of my house to the...
    Bartimaues Bartimaues 31-35, M 2 Responses Jul 14

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    HOW i told my parents and the results if u have not told ur parents and are thinking bout it read this NOW!!!!!!!!!!!!!!!!!!!!!so this is what happened i had written a note and...
    zoey764 zoey764 18-21 6 Responses Jul 19

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    Was decorating on a hot day so was home alone and could not be seen so decided to do it naked didnt realise my wife had given her mum a key and that she was calling round heard the...
    danglybits danglybits 46-50, M 5 Responses Jul 5

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    I was at a motel for an interview. I got there two days early and got to know the area and the people on the desk. I let them know I wore very little as often as i could. The...
    beret beret 51-55, M 3 Responses a week ago

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    When I was 14 I had a weekend alone at home. Our house was pretty secluded but there was one house nearby on a shared driveway. I went outside naked 'cause I could, until I saw...
    drune77 drune77 36-40, M 5 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 3 days ago

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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 2 Responses 3 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 day ago

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    Went for my massage like this :) my masseuse loved it, said she liked me in this one
    naughtychef naughtychef 26-30, M 3 Responses Jul 2

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    I love dressing up on webcam and showing off or swapping pics with sexy girls
    69morninglory69 69morninglory69 26-30, M 2 days ago

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    Hello,my name is jacob but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this...
    zoey764 zoey764 18-21 3 Responses a week ago

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    I like watch you rub your self daughter
    Daddylicksyou Daddylicksyou 61-65, M 1 Response 2 days ago

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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 18-21 17 mins ago

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    So I love dressing up in my/and my wifes dresses. I love trying on her dresses. Wished I could do it with her knowing I would love to be fully out of the closet, I hate having to...
    Laurie1960 Laurie1960 51-55 8 Responses Jul 14

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    It was in high school I was walking changing in the changing room and 3 girls cornerd me and hung me in my underwear and I was wearing bra and panties and took all my clothes and...
    Jennifer1221 Jennifer1221 18-21, F Jul 16

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    Well, a lot of people are probably curious about my life. Well, I have been through a lot in the past, but this one was the worst I've ever went through. Though I was only down for...
    kamishiro kamishiro 26-30, M 2 Responses Jul 19

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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...
    K9Luvr K9Luvr 18-21, F 11 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...
    Soccer127 Soccer127 18-21, M 1 day ago

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    Last year, on August 23rd, my house was robbed while and my friend were in it! I had come home from the gym, and, as my parents were away for the week, I invited my friend,Callum...
    Userno243 Userno243 13-15, M Jul 9

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    Yup.. not worried at all, since I am all sexy *feels cocky* :P No, actually it is not about being sexy, I just think that I look younger than my age anyway, so it will take longer...
    MissGaga MissGaga 22-25, F 1 Response Jul 4

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    I really miss the library I went to. It was the largest branch and since things have gotten a bit busier in my life I can't go there as freely like I used to. Every chance I get I...
    FunnyandNerdy FunnyandNerdy 16-17, F Jul 19

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    I was always envious of those kids whose parents could sit down and help them with homework, especially algebra, trigonometry, geometry, calculus and stuff..... oh crikey, how I...
    Moonpenny Moonpenny 46-50, F 1 Response 6 hrs ago

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    When I was young the miniskirt was all the rage and we loved wearing them. We used to get into trouble at school if our skirts were too short but mum was very good about our desire...
    Jilly53 Jilly53 56-60, F 7 hrs ago

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    So I've liked wearing panties for awhile now but my girlfriend doesn't like it so I do it in secret. Here resently I got curious about thongs so I went and bought a few. One day my...
    Wedge796 Wedge796 22-25, M a week ago

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