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I Enjoy Doing Crossdress Dares

Personal Stories, Advice, and Support 2,112 People

    Pick an outfit for me

    and tell me where to go :) Will post pics ;)
    deleted deleted
    5 Responses Jun 12, 2014

    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 feeling that I am doing exactly what the other person wants/
    thighhighjerker thighhighjerker
    26-30, M
    5 Responses Oct 23, 2009

    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
    Mar 16, 2013

    Anyone give me some crossdress dares ill do

    anything ;) and ill show proof of dare if requested
    deleted deleted
    3 Responses Feb 19, 2015

    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
    Jun 16, 2013

    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

    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

    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
    1 Response Apr 8, 2012

    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

    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

    Teal Toes

    The Dare is at the very end. "That's an ... ummm ... interesting color." "Yes, isn't it! It's called, 'Don't Teal My Heart Away'." "That color is a bit unusual to use for toe nail polish isn't it?" "Maybe, but that's the whole point. Besides, it's doing double duty." "OK...
    Rowena68 Rowena68
    41-45, F
    6 Responses Aug 15, 2011

    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...
    51-55, M
    3 Responses Jan 22, 2013

    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
    9 Responses Jan 3, 2013


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    deleted deleted
    Apr 11, 2012

    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
    1 Response Mar 23, 2011

    Ok, so I fully dress,

    high heels, panties, lingerie, outfits...I have all my own stuff...anyone have a good date for me...btw nothing illegal or nasty other then that im pretty much game
    chase6069 chase6069
    41-45, T
    2 Responses Mar 3, 2015

    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
    1 Response Jul 19, 2010

    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
    4 Responses Jan 5, 2013

    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
    8 Responses Jul 5, 2011

    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
    7 Responses Apr 7, 2012

    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 years old, met a neighbors house for a cook-out one evening. When I arrived Adele said she really liked my shirt...
    deleted deleted
    1 Response Feb 2, 2012

    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
    6 Responses May 8, 2011

    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
    46-50, M
    1 Response Jul 3, 2013

    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
    10 Responses Aug 21, 2010

    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
    3 Responses Jul 16, 2015

    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
    deleted deleted
    1 Response Aug 13, 2015

    ok looking for someone to dare me i dont want

    anything to extreme because it would be my first one
    JadeChoceur JadeChoceur
    26-30, M
    1 Response Jan 17, 2016

    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

    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

    Ok dare me. It will be fun I love crossdressing

    but never been out in public. So dare away
    alexjordan alexjordan
    1 Response Mar 26, 2014
    chloerosecd chloerosecd
    18-21, M
    1 Response Jun 12, 2015

    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
    12 Responses Aug 14, 2013

    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
    1 Response Aug 28, 2015

    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
    51-55, M
    1 Response Jul 2, 2013

    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

    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
    1 Response May 31, 2013

    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
    2 Responses Jul 22, 2013

    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
    1 Response Nov 13, 2013


    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

    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
    1 Response Jun 13, 2013

    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

    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
    1 Response May 29, 2013

    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
    CoryCD CoryCD
    18-21, M
    Sep 23, 2014

    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

    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
    GirlyPyjamaLover GirlyPyjamaLover
    26-30, T
    3 Responses Nov 12, 2014

    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
    3 Responses Jun 17, 2013

    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, 2015

    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
    9 Responses Jul 23, 2012

    I would love a women to dare me to put on a one

    piece swimsuit and swim in it with her in a one piece suit too!. I would tell her, It's about time!
    w1piece w1piece
    56-60, M
    Feb 24, 2016

    Does anyone want to give me some dares to do?

    :) I will do pretty much anything
    deleted deleted
    2 Responses Mar 29, 2015

    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
    5 Responses Feb 24, 2015

    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...
    51-55, M
    1 Response Apr 26, 2013
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