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I Enjoy Doing Crossdress Dares

Personal Stories, Advice, and Support 2,126 People

    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 shape. After that it becomes subject to situations. Ive been strong, weak, aggressive, passive, I've also been manly and slightly feminine.  I want...
    zcrock79 zcrock79 36-40, M 4 Responses Oct 7, 2011

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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 1 Response Aug 9, 2013

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    Buisness Cards

    I was out walking one evening dressed up and I stopped and looked inside a phone booth. Inside there were a handful of cards, you know the type Sexy Susan and Juicy Lucy that sort of thing. Anyway, it turned out that one of the cards was for a cross dresser who was basically an...
    FAIRLANE1 FAIRLANE1 46-50, M 2 Responses Feb 25, 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 lost I would be here servant and have to wear nothing but a tiny red apron, which barely covered privates...
    kek0849 kek0849 56-60, M 4 Responses Oct 15, 2010

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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 distance. We did this a few times but then I saw her talking to a guy. As I walked over to them the guy walked away...
    FAIRLANE1 FAIRLANE1 46-50, M 4 Responses Jan 22, 2013

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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 warm when she wore stockings during intercourse and even warmer when we lay in each others arms afterwards. I started to roll one...
    SaskiaIreland SaskiaIreland 31-35, M 7 Responses May 8, 2011

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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 girlfriend and my girlfriend had to choose some cloths for me to wear i knew this would not be good but i did it anyway...
    sissyslut64 sissyslut64 18-21, M 2 Responses Nov 13, 2013

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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 the time we know each other and it's only going to get better! One night she asked me to wear panties (her phrase, i say knickers) to work the next...
    SaskiaIreland SaskiaIreland 31-35, M 10 Responses Jul 5, 2011

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    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 met up with him but some nice dares to start with: 1. wear pantyhose with no socks for the day and go out where you can...
    timcdofsd timcdofsd 51-55 Sep 7, 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 black patterned pants, but I cut the pants off to make daisy duke shorts. They show full butt cheeks. I just got back in...
    Muriele Muriele 51-55, T 2 Responses Jun 15, 2013

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    when the wife dare's me,

    i don't wan't complet strangers to dare me into anything, and i sertantly won't do it if i don't wan't too, but i like too push my limits and the wife knows that, so from time to time she will dare me
    bodylower bodylower 31-35, M 1 Response Mar 23

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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. 4 different outfits, 4 different locations. First, a local apartment complex that has a pool and fitness center. i am to wear fencenet hose, a red...
    Mirandarenee26 Mirandarenee26 41-45, M 8 Responses Aug 16, 2012

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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 products. I was going to start having a period every month. I had to go to a drug store and purchase a box of...
    deleted deleted 26-30 1 Response May 31, 2013

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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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    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!!!!!!!!!!!! Little did my wife know how much I wanted this to happen.I played it cool for that evening,but...
    sameboat2 sameboat2 56-60, M 2 Responses Jun 26, 2013

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    Ftrwejtrstgw45ued

    Wdfgdtyukioy89t76543wefrghjkuio9pu0-9876r8t9oiukj hgftrsyrtyo8i765432wswq3245t76uioil yuiop9089iyujru7yujtdyjurtiyo097876u5terghtyrtearw oh98got7fl897ftrd646r32qszxfewqwertsertyuyrterwsdfd gfhgjiuo908768oipikjmklp897654ertgfhhjyiuytr ewr3423qwsaqw12wefdcxvbgty453edsvbgjhyutrew...
    deleted deleted 26-30 1 Response Apr 11, 2012

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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 thinking about it, excited me. I do it all the time now, but the first time I will never forget. I was hoping...
    makaila59 makaila59 51-55 11 Responses Aug 21, 2010

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    My Part Time Job

    I was asked to help a friend of a friend who needed help with is accounts,and I visited this middle age man who thanked me for calling at his house to do his accounts . I was dressed in my male gear and he asked me to work in a spare bedroom that was now a part time office...
    pleatedgirly pleatedgirly 36-40 8 Responses Jul 23, 2012

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    Pick an outfit for me

    and tell me where to go :) Will post pics ;)
    LisaTG LisaTG 26-30, T 6 Responses Jun 12

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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 though when a girlfriend at the time had said she would “let me go further” if I carried out a few dares for her amusement...
    glasgownaughty glasgownaughty 46-50, F 7 Responses Aug 21, 2011

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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 gone to bed but we were doing the typical playing around which led to truth or dare but slowly led to dares only...
    timcdofsd timcdofsd 51-55 1 Response Aug 17, 2013

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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. She often has me wear my stiletto hooker boots so I can't easily remove my heels and has added that I cannot avoid cars or people walking...
    Mirandarenee26 Mirandarenee26 41-45, M 9 Responses Apr 7, 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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    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 do to you, while out and while dressed in said clothing? You can be as conservative or as outragous as you like. Katy X
    FAIRLANE1 FAIRLANE1 46-50, M Apr 12, 2013

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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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    ryenmatt ryenmatt 36-40, M 7 Responses Jul 5, 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 Satin Lingerie. My dad's girlfriend at the time was a smoking hot blonde with 38dd's and she only wore satin underthings and...
    satinpantiesr4me satinpantiesr4me 41-45, M 1 Response Jul 3, 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 walking through the park from a distance. We did this a few times but then I saw her talking to a guy. As I...
    FAIRLANE1 FAIRLANE1 46-50, M 2 Responses Apr 26, 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 seek in the lingerie dept.  Her favorite is to hide a diaper pin in a bra or panty in a lingerie dept without me looking...
    Sissy916 Sissy916 41-45, M 3 Responses Jan 29, 2011

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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 early on a friday afternoon. My wife had left a note on the kitchen counter to go into the bedroom and follow the...
    pantiescouple pantiescouple 26-30 1 Response Jul 19, 2010

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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 love some ideas/dares for this long week. Public/day trips/shopping etc etc. Will look forward to reading replys, thank you xx
    Kimberlyfoster Kimberlyfoster 36-40 2 Responses Jul 22, 2013

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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-ups or thigh highs), a garter belt (if needed for your thigh highs), a pair of panties (your choice) and a toy, vibrator, ***** or...
    sissyskoolgurlatgmailcom sissyskoolgurlatgmailcom 46-50 15 Responses Aug 14, 2013

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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 high heels with nice femme slacks on and go out for a walk and drive to a special place and take a picture and send it too him...
    deleted deleted 26-30 1 Response May 29, 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 sisters friends knows works there. He's a real nerdy type of guy and sometimes the girls will flirt with him and he doesn't get it. I...
    deleted deleted 26-30 2 Responses Mar 23, 2011

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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 going to clubs, then one night she  added a twist.We were both dressed in little black dresses, with lots of leg...
    RunAroundSusan RunAroundSusan 22-25 Mar 16, 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 like them to be. This means however that I really should make the most of them when they come along. The problem I have...
    tvalex tvalex 46-50, M 3 Responses Jul 2, 2013

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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 such a short time ago) crossdressers like myself hid in shame and fear of being found out, though for many the desire to be...
    AZgirlMichelle AZgirlMichelle 46-50, M 11 Responses Nov 20, 2011

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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 humour,who lives in the suburbs with his straight laced wife. We agreed on a suitable outfit which was not too exciting - a...
    wetrev wetrev 46-50, M 5 Responses Apr 8, 2012

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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 go through with them. That changed last December thanks to EP. I found a link here to a sissy dare site where I connected with...
    DanielleMarieParis DanielleMarieParis 51-55, M 2 Responses Jun 16, 2013

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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 done. The first few times were at our old apartment complex at night onto our patio late at night, then onto...
    JosetteLaRoc JosetteLaRoc 36-40 1 Response Jun 13, 2013

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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 suggested additions) is high risk (which of course is the thrill) so please be aware of the consequences of something...
    territgirl territgirl 51-55, T 9 Responses Nov 30, 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 entrance doors. I had gone to work with all my finery on under my clothes. Stockings, suspenders, silky panties and a full length...
    debbiesucks debbiesucks 46-50, T 12 Responses Jan 3, 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 picture of me doing it as well. Well I had meet this person and began chatting with them and we hit it off. She was a dom...
    deleted deleted 26-30 1 Response May 13, 2013

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    Clarissetv Clarissetv 26-30, T 3 Responses May 12

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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. Probably one of the few places you can do go without a lot of negative reaction. Take a picture of yourself in a booth as...
    ForcedSissyGurl ForcedSissyGurl 31-35, M 10 Responses Feb 7, 2012

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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 walking through the park on my own, wearing all female clothes, a wig and all the right make-up. As i approached this...
    FAIRLANE1 FAIRLANE1 46-50, M 2 Responses Apr 12, 2013

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    Ok dare me. It will be fun I love crossdressing

    but never been out in public. So dare away
    alexjordan alexjordan 18-21 2 Responses Mar 26

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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 experimented often. She would buy books on cross dressing, sissy play, bondage and obedience's/spankings. I was willing to do...
    suelip suelip 46-50, M 3 Responses Jun 6, 2012

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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 will be to share that first time. I will start by saying this....it was prearranged by Mistress Pamela. And it was not something that I was looking forward to...
    danagurl danagurl 26-30, T 70 Responses Nov 16, 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 our age, so I'd like a plan. I really really would like to have the nerve to dress for the pick up so this man could see...
    deleted deleted 26-30 3 Responses Jun 17, 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 (or dress). It should be a maximum of 1 inch below the bottom curve of your but cheeks, straight denim or floaty chiffon is preferred. Stand in front of a full...
    flirtygirl flirtygirl 31-35, T 8 Responses Oct 10, 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 limitless to the possibilities of ultra cool dares you all can surely come up with and I will do them. I don't care how risky, silly or whatever...
    1trj 1trj 41-45, M 17 Responses May 16, 2010

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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 flats or girls loafers. To complete the ensemble I throw on a cute sweater set. I spray myself with flower bomb (so pretty and girly...
    Prettyboy9999 Prettyboy9999 41-45, T 4 Responses Jul 8, 2013

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