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I Enjoy Doing Crossdress Dares

Personal Stories, Advice, and Support 2,111 People

    Dares From Others - Well these are some dares that I was given once by a CD who chatted with me a few years ago and liked it when I showed pictures of myself as I did them, never...
    timcdofsd timcdofsd 51-55 Sep 7, 2013

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    Film Dare. - A long time ago an ex girlfriend of mine dared me to go out while fully dressed with her and when we were out she wanted to film me walking through the park from a...
    FAIRLANE1 FAIRLANE1 41-45 4 Responses Jan 22, 2013

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    Nightie Night Out - It was delicious!!! I bought some new outfits today, and one I really like is a sheer bodice that comes just down to my genital area. It came with blue and...
    Muriele Muriele 51-55, T 2 Responses Jun 15, 2013

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    Want To Get My First Dare - I am a at home crossdresser who only wears satin and silk as a I love the feel of it on my skin. I was young when I had my first experience dressing in...
    satinpantiesr4me satinpantiesr4me 41-45, M 1 Response Jul 3, 2013

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    Instructions From Gf While She Is Out Of Town - My girlfriend is on her way back but won't be home until late morning so she gave me a few tasks to perform, all with pics expected...
    Mirandarenee26 Mirandarenee26 41-45, M 8 Responses Aug 16, 2012

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    Fancy Dress Parties - Now that my real life friends are starting to find out about my cross dressing, they keep organising fancy dress parties. Events where I can dress in...
    Heellover Heellover 36-40, M 1 Response Mar 8, 2013

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    7 Days Dressed "normal". - In a few months when the evenings start to get dark again i a planning a weeks holiday just for kimberly;) 7 days and nights of been a woman. I would...
    Kimberlyfoster Kimberlyfoster 36-40 2 Responses Jul 22, 2013

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    A Visit To My Brother In Law - Not long after we were married, my wife dared me to visit her brother dressed as a woman. Her brother is a rather stuffy accountant with no sense of...
    wetrev wetrev 46-50, M 5 Responses Apr 8, 2012

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    Crossdressed At Work - Not really a dare but quite daring One time I was working on a refurb of a plush office block that had full length mirrors on the back of the toilet...
    debbiesucks debbiesucks 46-50, T 10 Responses Jan 3, 2013

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    Wife'S First Dare - This happened about 4 years ago when my wife found out I enjoyed dressing. She liked how I looked when I was fully transformed.  She enjoyed us dressing then...
    RunAroundSusan RunAroundSusan 22-25 Mar 16, 2013

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    Has anyone got any good dares?
    krissy79 krissy79 31-35, T 2 Responses Dec 18, 2013

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    Late Night And Locked Out - I've spent many years trying to carry out sissy dares, with modest success. Without a partner though, it's easy to chicken out with no one to make me...
    DanielleMarieParis DanielleMarieParis 46-50, M 2 Responses Jun 16, 2013

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    Lingerie Dept Dare - My wife likes to dress me in lingerie and make me go to the mall shopping. She knows it excites me so much. She likes to embarrasse me by playing hide and...
    Sissy916 Sissy916 41-45, M 3 Responses Jan 29, 2011

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    I Was At The Local Cafe Today. - I went to the local cafe and had lunch.
    ryenmatt ryenmatt 36-40, M 1 Response Aug 31, 2013

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    I Will Do Anything I Am Dared To Do. - I would love doing crossdress dares! Please, people, dare me to anything crossdressed, I will do it I promise. Your imaginations are...
    1trj 1trj 41-45, M 18 Responses May 16, 2010

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    I Dare You To ... - Dress up in a short little skirt and go to an adult bookstore. For any closet CD who wishes she was brave enough to go out in public, here's your opportunity...
    ForcedSissyGurl ForcedSissyGurl 31-35, M 10 Responses Feb 7, 2012

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    Webcam Dares! - I love doing webcam stuff but dares are great to.  I love to be a slave to another's desires on webcam.  I love the feeling of being watched andd love the...
    thighhighjerker thighhighjerker 26-30, M 8 Responses Oct 23, 2009

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    How A Dare Changed My Life. - I crossdressed in secret for many years of my life, never venturing from my house, never telling a soul. Before the age of the internet (it seems...
    AZgirlMichelle AZgirlMichelle 46-50, M 11 Responses Nov 20, 2011

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    Double Dared - I was 15 the summer of 1950 when I was persuaded to perform a dare. It was embarrassing at first but it was fun at the same time. Several of my friends, all about 15...
    ison ison 70+, M 1 Response Feb 2, 2012

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    She Dared Me To Wear Her Stockings - While we were in bed one night after having sex, myself and an ex were chatting about dressing up for sex. She commented that her legs got very...
    SaskiaIreland SaskiaIreland 31-35, M 7 Responses May 8, 2011

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    My First Dare As Carrie - I had been dressing for a while but I got to know this friend and he was into high heels and pantyhose. He asked me to put on panties, pantyhose and buy...
    deleted deleted 26-30 1 Response May 29, 2013

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    A Couple Of Questions For You. - What would you have me wear, could be everyday clothes or a kinky uniform? Where would you take me dressed in said clothing? What would you make me...
    FAIRLANE1 FAIRLANE1 41-45 Apr 12, 2013

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    I Need To Be Pushed - Hi all I love to dress up but as with many of us I am married to a disapproving wife. This means that my opportunities are much more limited than I would...
    tvalex tvalex 46-50, M 3 Responses Jul 2, 2013

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    In My Past... - I remember back in my early days around (13 or 14 yrs) of dressing one summer a friend spent the night and he did not know that I like to dress up. The parents had...
    timcdofsd timcdofsd 51-55 1 Response Aug 17, 2013

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    Lost Bet - My wife and I made a bet on our old high school football teams game. The bet was that if I won, she would go nude at home the whole weekend and be my servant.  If I...
    kek0849 kek0849 56-60, M 4 Responses Oct 15, 2010

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    Dress Up Fun - This is really a continuation of my my 'Film dare', experiance. Where i was filmed by my ex-girlfriend sucking a guy in the local park. Well this time i was out...
    FAIRLANE1 FAIRLANE1 41-45 2 Responses Apr 12, 2013

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    Cross Dressing Dare - I have been given a dare... or rather a challege. My girlfriend is a Titan Fan and I am a Cardinal Fan. Tonight they are playing and looser must wear the...
    deleted deleted 26-30 6 Responses Aug 23, 2010

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    Go Ahead Dare Me - Go ahead and dare me. Let's see if I can do what you dare me to do. I have never done a dare but it sounds interesting and exciting. So what is your dare?
    Adam59 Adam59 56-60, M 1 Response Mar 13, 2013

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    2nd Dare - Well since I proved I could do it as told now the dares started. Next dare was to dress up in panties, pantyhose, femme jeans and go out and purchase femme hygiene...
    deleted deleted 26-30 1 Response May 31, 2013

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    Film Dare. - (I have put this on another page.) A long time ago an ex girlfriend of mine dared me to go out while fully dressed with her and when we were out she wanted to film me...
    FAIRLANE1 FAIRLANE1 41-45 2 Responses Apr 26, 2013

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    Dare ME - On a dare from my wife one night a while back,I wore pantyhose(Hers) and a pair of panties(Hers) under my clothes out to dinner.THEY FELT TOO TIGHT YET SOMEHOW WONDERFUL...
    sameboat2 sameboat2 56-60, M 2 Responses Jun 26, 2013

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    My Teenage Experience - When I was in my teens and exploring my sexuality, I used to get very aroused by women’s underwear – what teenage boy doesn’t? It took a new twist...
    glasgownaughty glasgownaughty 46-50, F 7 Responses Aug 21, 2011

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    Driving Dare - Here is a crossdressing driving based dare. A health warning: 1. This should done very late a night - for reasons that will become obvious! 2. This dare (and...
    territgirl territgirl 36-40, T 9 Responses Nov 30, 2012

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    Love Outside Dares While All Dressed Up - My gf sends me out in heels and dresses or skirts to get the mail, walk a lap around my parking lot, even has me stroll bar parking lots...
    Mirandarenee26 Mirandarenee26 41-45, M 9 Responses Apr 7, 2012

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    A Dare For All Of The Daring. - This is something I have done myself. I wouldn't dare you to do anything I, myself would be unwilling to do. First, gather a pair of stockings (stay...
    sissyskoolgurlatgmailcom sissyskoolgurlatgmailcom 46-50 14 Responses Aug 14, 2013

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    First Time Dare - The first time I really got to know someone and they dared me to do something I was scared. Because it was not only doing it out in public but also taking a...
    deleted deleted 26-30 2 Responses May 13, 2013

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    She Made Me Do It - i was over at a friends house over the weekend with some friends to play some truth or dare after 15 min of playing i was dared to go to the bedroom with my...
    sissyslut64 sissyslut64 18-21, M 2 Responses Nov 13, 2013

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    Dare! Go Out In A Short Skirt Super Turned On And Pantyless! - Get dressed and make sure your feeling super horny and very turned on. Choose your shortest sexiest little skirt...
    flirtygirl flirtygirl 31-35, T 6 Responses Oct 10, 2013

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    deleted deleted 26-30 1 Response Apr 11, 2012

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    Dare Me - I want to see what type of dare you guys will give me if its not to extreme I will try to do it and send photos to you off me doing your dare so dare away ;)
    jennytall jennytall 18-21 5 Responses Mar 27, 2013

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    Pushing The Envelope While Shopping - I love going shopping dressed in tights or nylons under a pair of leggings or Capri pants. Depending on nerves I will either were some ballet...
    Prettyboy9999 Prettyboy9999 41-45, T 4 Responses Jul 8, 2013

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    See My Bra? - My story goes back about two years ago. I used to just wear my pretty things around the house. I have always wanted to go out wearing my pretty bras and panties. Just...
    makaila59 makaila59 51-55 11 Responses Aug 21, 2010

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    Who Am I, Whats My Sexuality, What Do I Want. - I have wondered for years, I guess ill start by saying that the facts are as follows: Male, tall, not as small as I once was but in...
    zcrock79 zcrock79 36-40, M 4 Responses Oct 7, 2011

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    Dared To Wear Panties To Work, Then Tights.. - One of the friends i speak a lot about here lives a good distance away, so we keep in touch via text. We had had some great fun over...
    SaskiaIreland SaskiaIreland 31-35, M 10 Responses Jul 5, 2011

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    So Far - So far, I've dared myself on a few things. My wife knows that I crossdress. She prefers that I keep it inside our home. She would kill me to find out some things I've...
    JosetteLaRoc JosetteLaRoc 36-40 1 Response Jun 13, 2013

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    Riding My Bike In A Sports Bra -
    ryenmatt ryenmatt 36-40, M 7 Responses Jul 5, 2013

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    This Sounds Funn - Im Ashley im 20 and i would love to do cross dress dares ; ) Send me dares in a private message and ill do them and show you pictures : )
    ashley2o2 ashley2o2 18-21, F 2 Responses Aug 9, 2013

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    My Sisters Crossdressing Dare. - When I was 16 I would go out with my older sister and friend. There is this small convience store near our house. On monday nights this guy my...
    deleted deleted 26-30 2 Responses Mar 23, 2011

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    Do I Have The Nerve - My car is being picked up from my home this week and I will be here all alone. I have spoken to the man who is picking it up and he's quite cute for a man of...
    deleted deleted 26-30 4 Responses Jun 17, 2013

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    Crossdressing Fun - I have always enjoyed crossdressing, and my wife has always shared my fantasy of me being with a guy while dressed as a woman. I got home from a business trip...
    pantiescouple pantiescouple 26-30 1 Response Jul 19, 2010

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    My Name Is Dana....and I Am A Sissygurl....the Big Bang - Well, I promised to talk about the first time that I had intercourse. So, I guess this is as good a time as there ever...
    danagurl danagurl 26-30, T 72 Responses Nov 16, 2011

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    Cross Dressing Dares - Well as I have said in my profile. I have been cross dressing since I was 11 borrowing my sister's clothes. Well my now ex wife enjoyed me dressing and we...
    suelip suelip 46-50, M 3 Responses Jun 6, 2012