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I Enjoy Doing Crossdress Dares

Personal Stories, Advice, and Support 2,183 People

    Does anyone want to give me some dares to do?

    :) I will do pretty much anything
    GirlyLisaTG GirlyLisaTG 26-30, T 2 Responses Mar 29

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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...
    deleted deleted 26-30 1 Response Nov 13, 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 56-60, T 2 Responses Jun 15, 2013

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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 9 Responses Jul 23, 2012

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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 1 Response Sep 7, 2013

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    Ftrwejtrstgw45ued

    Wdfgdtyukioy89t76543wefrghjkuio9pu0-9876r8t9oiukj hgftrsyrtyo8i765432wswq3245t76uioil yuiop9089iyujru7yujtdyjurtiyo097876u5terghtyrtearw oh98got7fl897ftrd646r32qszxfewqwertsertyuyrterwsdfd gfhgjiuo908768oipikjmklp897654ertgfhhjyiuytr ewr3423qwsaqw12wefdcxvbgty453edsvbgjhyutrew...
    deleted deleted 26-30 Apr 11, 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 11 Responses Jan 3, 2013

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    CoryCD CoryCD 18-21, M Sep 23, 2014

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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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    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 9 Responses Oct 10, 2013

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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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    I have been cross dressing

    for some years now. But still very closeted. Would someone care to dare me to do anything to try and get me more out there into the cross dressing world? X
    Pjstuart Pjstuart 26-30, T 3 Responses Nov 12, 2014

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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 3 Responses Jan 22, 2013

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    chloerosecd chloerosecd 18-21, M 1 Response Jun 12

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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 1 Response Jul 2, 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 1 Response Apr 26, 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 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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    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 6 Responses Aug 16, 2012

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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 5 Responses Jul 8, 2013

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    Holloween

    This dare started on a paper route before my dads gf knew i crossdressed. Well any way we were deliverying to some boxes, there were 2 boxes and each box got 2 papers. So i said 2 2. Then we got back in the truck and i said haha tutu.i then said we should dress up for holloween...
    Girlsoon2b Girlsoon2b 18-21, M 2 Responses Oct 7, 2012

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    In Public Crossdressed In Male Mode.

    I find it very exciting to challenge myself to do darring things when I'm in a crossdressing mood. I went for a drive one day all dressed up but in male mode. I was getting so aroused looking at myself I felt the urge to get out of the car and take a short walk.  I did it in a...
    silkydrawers silkydrawers 46-50 6 Responses Jan 5, 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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    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 22-25, F 1 Response Aug 9, 2013

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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 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 3 Responses Oct 7, 2011

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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 36-40, M Mar 23, 2014

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    I'm 18 in LA and will do cross dressing

    and sissy dares and take pics of them. Dare me below
    tgirlgabi tgirlgabi 18-21, T 2 Responses Jul 16

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    I went outdoors on the coldest night of the

    winter wearing just a mini dress and heels talk about cold effecting you body - if you know my drift?
    sweetpeaDeby sweetpeaDeby 18-21, M 4 Responses Feb 24

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    Anyone give me some crossdress dares ill do

    anything ;) and ill show proof of dare if requested
    deleted deleted 26-30 4 Responses Feb 19

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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 3 Responses Feb 25, 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 1 Response Jun 26, 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 8 Responses Apr 7, 2012

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    I want to go out to a local gay friendly bar

    wearing a corset mini skirt hose and heels I will have a dress shirt Over the corset. I went there last week with a red corset under my dress shirt. The bartender noticed and made a comment I showed him and he though it was ok. I should also mention that I am at the bar often...
    jerbare jerbare 61-65, M Feb 28

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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 12 Responses Aug 14, 2013

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    I love doing crossdressing dares.

    I live in Virginia, USA msg me if ur close. Msg me if have a date for me I will send u the pic of me doing it
    CDerforlife CDerforlife 18-21, M 3 Responses Aug 13

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    My wife dared me to dance

    and twirl in front of our picture windows that can be seen from our neighbors houses across the lawns. Both neighbors houses lights were on and shades open. Our lights I was dared to turn on leaving the blinds up. I could see one set of neighbors watching tv facing us. She...
    Chares184 Chares184 51-55, M 3 Responses Jul 18

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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 66-70, M 4 Responses Oct 15, 2010

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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 3 Responses Apr 8, 2012

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    Pick an outfit for me

    and tell me where to go :) Will post pics ;)
    GirlyLisaTG GirlyLisaTG 26-30, T 5 Responses Jun 12, 2014

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    The latest thing I dared myself to do was take

    a walk out my driveway wearing just my lingerie. I can't tell you how exciting it was to go through with this dare.
    silkydrawers silkydrawers 46-50 3 days ago

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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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    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 1 Response Jun 16, 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 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 Aug 17, 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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    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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    Ok dare me. It will be fun I love crossdressing

    but never been out in public. So dare away
    alexjordan alexjordan 22-25 1 Response Mar 26, 2014

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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 8 Responses Nov 20, 2011