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I Was Caught Wearing A Bra

Personal Stories, Advice, and Support 171 People

    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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    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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    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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    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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    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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    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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    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 6 days 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 3 Responses Jul 9

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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 4 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 2 Responses Jul 15

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    he was my dads friend and i went their with some kinda math problem ...his wife was at work ...i guess i was wearing a to short of skirt with out any panties...lol
    lilkimmie lilkimmie 18-21, F 5 Responses Jun 29

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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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    After underdressing in bra and panties for several years, I decided to venture out fully dressed to a distant city to do some shopping. So, I left home fully dressed and madeup...
    DonnaSue10 DonnaSue10 66-70, M 2 Responses Jun 30

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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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    He lives next door. I spied on him through the window and he caught me looking at him. I immediately turned away. Now he thinks I'm a creep. We've never met because I only come...
    Inezb Inezb 18-21, F Jun 24

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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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    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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    In my late teens, I worked and lived in a hotel. I was toned with quite large breasts back then and was at the beginning of my sexual adventures. A habit I had back then which...
    vitalised vitalised 31-35, F 3 Responses Jun 30

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    I go to a few steam rallies with my dad and brother as we own a traction engine to take there. Once, it was my turn to light it, at 5:30am, so I had to be up at 5am to get it ready...
    HayWalker HayWalker 22-25, F 3 Responses Jun 30

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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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    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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    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...
    jmallon764 jmallon764 18-21, M 5 Responses 4 days ago

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    I ws 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 15 hrs 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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    They make breasts look and feel less like breasts and are sometimes uncomfortable. But there are certain occasions when I have to wear them.
    HannibalQ HannibalQ 16-17, F 3 Responses Jun 24

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    Every day. At school, at the mall, at home, and his family reunion, everywhere.
    pardax pardax 13-15, M Jun 25

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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...
    jmallon764 jmallon764 18-21, M 3 Responses 1 day 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 7 Responses Jul 14

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    My boyfriend had my Brand New Car impounded after he was caught street racing! I will find his OFF switch once and for all! I hate him!
    BeadyBlack BeadyBlack 18-21, F 1 Response Jun 26

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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 1 Response 4 days 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 2 Responses 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 4 days ago

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    I've been wearing panties for about a year now. My first time wearing panties happened was when I was at the store finding some new clothes.When I went to changing rooms to size, I...
    Sahawks18 Sahawks18 16-17, M 4 Responses 4 hrs ago

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    I don't know if writing about it is going to make me feel better or not, but here goes nothing anyways. Just a few days ago, summer school ended. We were amazingly happy about...
    KatieRosess KatieRosess 16-17, F 4 hrs ago

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    I was drawing Tuesday night.. And I was listening to music I do that so I don't get scared. I used to be afraid to go in my own room. me and Jake used to sleep with dad every...
    KovusShame KovusShame 13-15, F 4 hrs ago

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    Thursday, July 24, 2014....Today I'm wearing white Dockers briefs. These are some of the most comfortable fly-front briefs I've ever worn.
    UndieGuy UndieGuy 36-40, M 1 Response 8 hrs ago

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    Today i am wearing white boyshor panties with lace trim
    oneperson93 oneperson93 18-21, M 2 Responses 2 hrs ago

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    I am a man just under 50 years old, lost some weight and am thinking about wearing a thong at the Salt River Recreation near Phoenix. This is an area where tubing is popular. I...
    saltriverrat saltriverrat 46-50, M 40 mins 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 1 day ago

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    It's weird but I just feel pretty I guess when I wear them. When I go ago shopping I usually try on some high heeled shoe. This pic was obviously to small though :) lol
    thatgirlluvsred thatgirlluvsred 13-15, F 1 hr ago