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I Was Caught Having Sex While Crossdressed

Personal Stories, Advice, and Support 17 People

    My husband was having a good day at work so he came home early. Our children where at school except one who was sick. I thought she was asleep so me and him started to fool around...
    deleted deleted 26-30 4 Responses Jul 12

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    i'd be sleeping in my bedroom and he would sneak over and touch me while i was sleeping
    nautimickey nautimickey 41-45, F 1 day ago

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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...
    banannasplitz09 banannasplitz09 22-25, M 1 Response 1 day ago

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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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    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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    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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    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 1 Response Jul 18

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    Man, living sexually frustrated is hard. The culligan man came in to work to bring the water and i wanted to ask him to go in the back with me. I picture having sex with people...
    marleyjane marleyjane 22-25, F 3 Responses Jul 24

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    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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    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 5 Responses Jul 13

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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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    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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    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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    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 4 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 2 days ago

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    Its weird but i want to have the most sex i can (:
    cyndyarcia1 cyndyarcia1 18-21, F 3 Responses Jul 15

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    In another imaginary paralel dimension...I would be totally independant and rich,with another totally independant and rich girl...we both would be important artists developing and...
    4biandu 4biandu 26-30, F Jul 15

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    I get really wet when I get sexy or dirty photos!! Anyone care to share any with me?
    69dirtygirl69 69dirtygirl69 16-17, F 3 Responses Jul 20

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    Would love to have Sex with a pregnant woman would be a great turn on
    Hazza8989 Hazza8989 22-25, M a week ago

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    It was weird, me and my best friend were watching those types of videos and we were touching each other, then all of a sudden he grabbed me, made out with me...I think you can tell...
    bisexuwhale bisexuwhale 13-15, M 1 Response 4 days ago

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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 6 Responses Jul 5

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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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    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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    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 4 Responses Jul 24

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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 6 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 5 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 4 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...
    Soccer127 Soccer127 18-21, M 1 day ago

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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 1 day ago

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    It just feels so good to have it done
    honey2828 honey2828 26-30, F 2 Responses Jul 22

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    i cant stop cheating on my wife,she is the best in every way.and that is what makes it more ****** up.
    anarchdote anarchdote 26-30, M 1 Response Jul 20

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    I hate and love this curse, it's a free drug that ruins my life, it relieves my stress and causes it at the same time, I control it but it controls me. How can I quit something...
    VenusIncarnate VenusIncarnate 26-30, F 5 Responses Jul 22

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    Surprised females want this aswell haha
    ryanmona ryanmona 18-21, M 1 Response Jul 22

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    I want to be taken in front of my parents. They can see how corrupted their perfect little girl is.
    libertinette libertinette 22-25, F 17 Responses 1 day 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 Jul 23

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    I like watch you rub your self daughter
    Daddylicksyou Daddylicksyou 61-65, M 1 Response 3 days ago

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    I have had morphea since 1965 at the age of 14. Back then it was extremely rare to find a doctor who even knew what morphea was. My morphea started as a round spot on my wrist...
    Muffygirl Muffygirl 61-65, F 1 Response 18 hrs ago

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    Okay I live in Michigan I was 17 now 18 at the time and the age to consent to sex is 16 I'm guessing that's with any age but below 16. Anyways this 42 year old police officer who...
    cupcakes38 cupcakes38 18-21, F 3 Responses Jul 19

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    Okay I live in Michigan and the age to consent to sex is 16 I'm guessing that's with any age but below 16. Anyways this 42 year old police officer who lives in Canada came over the...
    cupcakes38 cupcakes38 18-21, F 4 Responses Jul 19

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    Sex has always been difficult for me. It started with my first girlfriend. She came and I didn't. And thus it didn't feed my "reward system" the way it did hers. It continued on...
    cracklewalk cracklewalk 46-50, M 7 Responses Jul 20

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    From Psychology Today "Contrary to conventional wisdom, married couples—and their cohabiting counterparts—have more sex than the nonmarried, a fact confirmed in a 2010 survey...
    Mettamomma Mettamomma 61-65, F 8 Responses Jul 7

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    I’m finally out. Hi everyone. I joined this group two days ago to get support to leave forever my MM. After reading everyone’s stories, I feel compelled to write mine. I am...
    nycgrrrl nycgrrrl 41-45, F 2 Responses Jul 4

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    Sexless Marriage is a Biblical Reason for Divorce This is a re-post of a comment I wrote to someone that TheWendigo suggested I post as a story, in case it helps anyone. I am...
    UndefinedValue UndefinedValue 31-35, F 13 Responses Jul 21

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    Sexually frustrated husband uses spreadsheet to show wife what's wrong with their sexlife. I have empathy for the husband. Obviously, however, his spreadsheet didn't inspire his...
    Mettamomma Mettamomma 61-65, F 15 Responses Jul 21

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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 1 Response 1 day ago

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    For many years everything was great - including the sex. Then menopause and hormones kicked in and she has zero - I mean ZERO interest in having sex or pleasuring me. We're still...
    amaturegent amaturegent 56-60, M 9 Responses Jul 2