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I Would Love 2 B Crossdressed In A Room Full Of Women

Personal Stories, Advice, and Support 1,059 People

    The Nearest I Have Been

    The nearest I have been to this is when I went to a brothel a few years ago. I dressed as a **** in pink satin corset, pink satin panties, black stockings, high heels and a maids outfit. The lady played with me on my own for a while and then made me suck off a guy she had in...
    satinslutlouise satinslutlouise 41-45, M 1 Response Apr 12, 2010

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    Make A Day Of It!

    Apparently 21st June is the day for all of us boys to throw away our trousers and put on a skirt! You could use it to fundraise too, as a dare, 'If I raise over £100 I'll wear a skirt for the day!' Anyone interested in getting men into skirts, join this group on Yahoo! http...
    deleted deleted 26-30 1 Response Apr 21, 2011

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    Did It! (Follow Up To: Tonight’S The Big Night)

    The deed is done. I did it. WE did it. First my wife shaved every body hair I had from the neck down not including my arms. Shower and then perfume she picked out. Next was the see through g-string and fishnet pantyhose. Then the cute little lady bug costume. Finally I put on...
    2muchexp 2muchexp 51-55, M Oct 28, 2013

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    It Would Be Great!

    I would love to have them all dress me up and pamper me. and then take me to the bedroom and let me orally service them all as they take turns ******* my ***!
    allwrappedupinit allwrappedupinit 51-55, M 1 Response Jul 14, 2011

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    Maid

    my Mistress dressed me up as a pink sissybitch in a short pink sissy dress with a stiff petticoat pushing it up pink bra,panties and garter belt with pink stockings and 4" heels on then she invited her girlfriends over. i had to service their wishes all evening...
    mandiejune mandiejune 51-55, M 2 Responses Mar 27, 2010

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    Used

    I dream about the day when a group of women will take me under their wing and transform me into the most feminine girl that I could possibly be. Dressing me in sexy lingerie,stockings ,skirt and heels. Helping me out with my makeup and ready to party with them. We all go to a bar...
    kathyr61 kathyr61 56-60, M Jan 11, 2013

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    I Have Done This

    I have dressed up in the company of females and it was so much fun. Lots of woman are cool with this, I have found.
    RobynTheBeautiful RobynTheBeautiful 41-45 1 Response Jan 1, 2012

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    Tonight's The Big Night!

    OK tonight is the big night. Tonight I’m going out with my wife to a huge party in Houston. I’ll be in my panties, stockings, petticoat, heels and this cute little lady bug costume. I’ll have in my fake ****. The world will finally see me as the sissy boy I really am...
    2muchexp 2muchexp 51-55, M Oct 26, 2013

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    Unfortunate? Experience

    my earliest sexual experience was when I went over to my friends and to my surprise when she left the room and came back, she was undressed. She then told me that if I dd not undress as well that she would say I forced her to undress. After I undressed, she made me put on her...
    asmethious asmethious 36-40, M 1 Response Sep 18, 2010

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    I guess this counts. Dressed completely

    as Debbie with wig, full makeup, jewelry and perfume, I scheduled an appointment today to have my underarms waxed. I love getting all my ugly gross male body hair waxed.
    debbienc debbienc 61-65, T 1 Response Oct 7

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    Sissy Model Wanted ( The Offer, I Did Not Declinde ) (fantasy)

    The week after my interview with Mary, she called me early in the morning before work!  She wanted to know, if I wanted the job, and if, I could start training right away!  I was unsure what kind of training was involved, and she explained that every night after work...
    haileeTV haileeTV 41-45, T 2 Responses Apr 8, 2010

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    Not Sure A Room Full

    I would love to be crossdressed in a room with a couple women, just not a room full.I would love for them to pamper me, and show me lots of attention.
    happilymarriedguy happilymarriedguy 51-55, M 1 Response May 23, 2012

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    Not long ago this was a goal

    but in the last several months I have actually had the pleasure of being fully crossdressed in a room full of women. I suppose it counts that this was accomplished when I dressed fully as Debbie with appropriate lingerie and feminine outer clothes and went to a salon to have my...
    debbienc debbienc 61-65, T 2 Responses Feb 28

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    Crossdressing With Wife

    I’m a male who likes to crossdress and my wife knows about this and gets so turned on seeing me dressed. My wife loves to use toys on me and we have a *******, she also helps me go shopping and picks out women’s clothes that will look good on me. I love wearing sexy undies...
    pantiescouple pantiescouple 26-30 Jul 19, 2010

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    Going To A All Girl Event

    I wanted to go to this Devonshire tea event that was in aid of breast cancer research. So I rang my friend who new that I was a cross dresser . H er name is Lisa. She found out through my stupidity with a computer and I invited her to be friends on face book as Abigail .any way...
    Abigail590 Abigail590 41-45, T Aug 14, 2010

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    Really

    This is my greatest fantasy I really want to go into a room as a guy and come out a gurl letting them femm me up and make me just like them
    mazzz77 mazzz77 18-21, M Nov 10, 2010

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    Would Be So Much Fun

    I've often fantasized about being so nicely dressed that I'd fit in with a room full of women, girls who would accept me as one of them, so we could talk about guys (I'm gay, so that would be easy), about girly things. We'd go shopping, go out to eat, and I wouldn't be treated as...
    NathanielPantied NathanielPantied 46-50, M Nov 14, 2011

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    Embarrased When Caught

    I love wearing girls dresses and when dressed I often imagine being caught and dragged out infront of group of girls and women who would laugh and make fun of me. The thought of being caught is very scarry and I do what I can not to be caught but wish it would happen so that I...
    Karentg Karentg 46-50, M 4 Responses Aug 26, 2012

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    I Was!

    I used to belong to a group of guys who would cross dress. One time we orginized a formal dress ball. in attenance was life partners ,ladies who were involved in providing necessary items to us,cosmetics,clothes,wigs shoes and even emotional support. We rented a banquet hall at a...
    connie2much4me connie2much4me 56-60, T 5 Responses Feb 15, 2011

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    Were Talking About Heaven Here!

    New neighbors moved in next door, 2 middle aged women. One is a great baker and came over to borrow a cup of sugar. Well, I was downstairs "dressing up" and didn't hear someone was at the door. "Hello?!?!"    I freaked because I am in the closet! OMG, no one knows I crossdress...
    CandyKowal CandyKowal 46-50, T 6 Responses Sep 18, 2011

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    Not A Room But A Patio ??

    I have crossdressed for years and am now sub to my Mistress J. We only ever play at work after hours or on business trips ( I`m the boss, she is my P.A.) Please note this is merely a sex thing & not lifestyle. A few months ago, on one of the few hot days this summer, I had a...
    ronkey02 ronkey02 56-60, M 1 Response May 4, 2011

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    Exciting Thoughts About Being In Front Of Women

    Just the thought of being dressed in front of a room full of women is such a turn on. To realize that they look at you in a different way because you are dressed like a sissy. That you probably will never be able to satisfy them like a real man. That you want to pleasure a...
    Cristine3030 Cristine3030 41-45, T 1 Response Jul 1, 2012

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    Lovely Soft, Silky Gown

    I would like to be wearing a long, silky, lacy nightgown in a room full of beautiful girls also dressed in pretty nighties. They would caress me and tell me how pretty my gown was, and as a climax (pun intended) one of the them would give me a blow job while we were both wearing...
    gown1000 gown1000 66-70, M Sep 21, 2013

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    Prissy Sissy Coming Out Party

    Until recently this sissy thought she was a transgendered person who loved being extremely feminine. However after being on the net for some time I came to the conclusion that I was in fact a sissy. I showed what I had found to Mother and she totaly agrees. She has made me take...
    janetkotex janetkotex 22-25, T 6 Responses Apr 19, 2011

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    Oh Yes- Girdles

    I love wearing a good fitting longleg panty girdle with sleek full fashioned nylons..Same story-discovered that "cared for" feeling during early adolescence and have loved it ever since. It's wonderful to be held like that. That's all for now. Don't get me started!
    blart blart 66-70, M 2 Responses Jul 11, 2011

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    The Nurses Party!

    So when I was about 20, shortly after leaving college and starting work, I lived in a shared house. Two of the residents were student nurses (both female), and 1 was a female architect. So it was a bit of heaven being amongst these lovely young ladies all the time. It was common...
    sissifyme sissifyme 46-50, M 5 Responses Dec 12, 2012

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    Sissy Model Wanted (the Interview) (fantasy)

    The add in the local paper read: Sissy Model Wanted!   I was intrigued by the add so I called the number to see what it was all about!  The phone was answered by the local adult book store!  I was kind of stumbling on about the add, when the girl said oh...
    haileeTV haileeTV 41-45, T 10 Responses Mar 27, 2010

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    What A Fantasy Come True

    Imagine being in a room full of women to cross dress you? It would be a dream come true. It hasn't happened. I did have a few opportunities to dress as a woman with only one woman present so so many years ago. The adrenaline really kicks in. It is lots of fun to dress and...
    jml2000 jml2000 56-60, M 1 Response Mar 16, 2013

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    Id Love To

    I think I'd love to be dressed in my prettiest things and then be fussed over by a room full of women Kisses Dennis / Denise
    deleted deleted 26-30 2 Responses Nov 18, 2010

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    I Am Very Tempted To Go Out With A Group Of Women, Dressed "en Femme"

    Here, in Christchurch, New Zealand, we have a major event each year........The New Zealand Trotting Cup.  Trotting is Harness Horse Racing, for you people who don't understand.      It has become quite an event, where men would go along all dressed...
    redbow25 redbow25 56-60, M 1 Response May 19, 2010

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    Oh My, , I Wish X

    That has to be an all time fantasy. To be dressed by a room full of hot sexy seductively dressed females all wanting to touch and stroke your silk and lace clad body, all wanting a taste of your clitty. I'd certainly need milking then !!!! oooooooo
    silkysissyprincess silkysissyprincess 41-45 1 Response Mar 28, 2012

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    Was Crossdressed By Two Women

        The year was 1988, it was nearly halloween.  My brothers children wanted to go out trick or treating but couldn't take them due to work commitments I volunteered to take them.   My Sister-in-law was ecstatic, finally the three kids would get to...
    bobbie13 bobbie13 56-60, T 7 Responses Aug 3, 2010

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    3 Little Wishes!!!! If Only Dreams Came True! I Have Posted This In Another Group But Think It Fits Here Perfectly Also.

    I was feeling very low i had lost my job, my wife was very angry and was not holding back with her humiliating comments, normally i would be in heaven being belittled by her since she had discovered my overwhelming need to wear wonderful female clothing but losing my job just...
    carolesweetie carolesweetie 36-40, T 1 Response Jan 6, 2012

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    Washing Dishes

    Last night while my wife was out with the girls I had the house all to myself and decided it was time to let Jessica out to play a little bit. I had a sink full of dishes to do and figured why not bring Jessica out to do them, it would make it more enjoyable. So I went upstairs...
    JESSICAKNIGHT JESSICAKNIGHT 51-55, T 2 Responses Jul 15, 2010

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    Related Experiences

    I would love to have a women just take advantage of me. Tie me up slap me play with me ;)
    madisonjackson24 madisonjackson24 18-21, F 1 Response Sep 26

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    I think it's more "I feel anxious in a room full of people." I don't know why, but I just do. Whenever there's a gathering, or even that I have to be in a crowd, I feel all...
    lonelydinosaur lonelydinosaur 26-30, F 3 Responses Sep 27

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    I just love looking at beautiful women. I'm bi-sexual, and I love both genders equally, but I love women a tad bit more.
    SluttyGirlJane SluttyGirlJane 13-15, F Oct 16

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    I just love looking at beautiful women. I'm bi-sexual, and I love both genders equally, but I love women a tad bit more.
    SluttyGirlJane SluttyGirlJane 13-15, F Oct 16

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    This girl tho:) she is such a babe:) love my roommate so much:D
    BlondyRae BlondyRae 16-17, F 3 Responses Oct 7

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    you are know the thing I would love to do is go to the shop clothing if I have free time I always looking and noticed somewhere there is shop clothing when I was past and me...
    genteel genteel 46-50, M 1 Response Sep 27

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    so I could boss her around and we could get into shenanigans together, and then cover for each other and be on each other's teams. I would lover to have a little sister! I think...
    Theworldisminenow Theworldisminenow 18-21, F 1 Response Oct 12

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    weekend I stay home all day in pajamas until evening I shower and then replace another clean pair else I don't want only a pair for whole day even in the end of the day then during...
    genteel genteel 46-50, M 1 Response Oct 15

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    I'm a uk nappy lover and love wearing outside. I don't have any camping equiptment but would love to go camping with boys into nappies and sissy things .I'm from West Sussex...
    SEANYBABYNAPPY SEANYBABYNAPPY 51-55 3 Responses 2 days ago

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    I would LOVE to be put otk and spanked long and hard by a mistress
    Naughtykay14 Naughtykay14 22-25, F 4 Responses Sep 24

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    I would love to write to someone about random stupid things in life. A pen pal where can write our own stories to each other and share our life experiences with. Please message me...
    strawberriful strawberriful 18-21, M 2 Responses Oct 1

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    I would love a pen pal! Someone who also suffers with CFS/ME.. If that could be you, please comment :')
    MrsKAura MrsKAura 18-21, F Oct 1

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    So, I'm not all that social, but I would love to have some new friends! I am a teen mother and when I got pregnant, all my previous friends were no where to be found.. And now, as...
    KaylaSilva2 KaylaSilva2 16-17, F 1 Response Oct 1

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    I would love to hear the wild taboo stories yall have experienced 😜
    mikew4358 mikew4358 22-25, M Oct 14

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    This week was a spirit week and everyone dressed up for themes. We had a blast taking pictures with each other. The thing is... I would take pictures FOR them, not WITH them. I...
    LonelyUsagi LonelyUsagi 13-15, F Sep 26

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    I just bought a Blue SecondSkin Full Body Spandex/Lycra Suit. This is my second full body spandex suit from SecondSkin Suits. I am currently wearing my red full body spandex suit...
    ILoveSpandex ILoveSpandex 18-21, M Oct 4

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    Have you ever talked to someone and for the first time starting thinking, wow he/she's so beautiful.How didn't I see that before? Well thats how I feel about women with dark brown...
    goodgoliath goodgoliath 31-35, M 1 Response 5 days ago