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I Love To Dress As A Woman In High Heels Dresses And Makeup

Personal Stories, Advice, and Support 3,652 People

    I love dressing up but I always save makeup

    for last and it seems to be my favorite part. I love makeup! Especially liquid eyeliner, eye shadows and lipstick! I even love shopping for makeup, although online only because I'm still a little too shy to buy in public.
    jessicavamp jessicavamp 41-45, M 4 Responses Apr 16, 2015

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    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels and definetly make up and I also secretly am attracted to masculine tough and hairy men
    deleted deleted 26-30 1 Response Nov 24, 2015

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    Not as much as I use to,

    but Iwould venture out fully dressed 2-3 times a month.
    TVTVTVTV TVTVTVTV 51-55, M 4 Responses Apr 1, 2014

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    I to love to dress as a woman

    and wear high heels with a 7 inch high heel and makeup and go out in public
    wissers wissers 66-70 2 Responses Apr 16, 2015

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    Part Of Feeling Feminine

    I love dresses and high heels. Today I indulged myself and bought three dresses and three pair of high heels. Even though I wasnt going anywhere, I did my hair, curled it up, and feel very happy just with it :D.
    Calipri Calipri 22-25, F 7 Responses Jun 23, 2012

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    Dont know what it is,

    but I feel so at peace and so fulfilled when dressed. Right now I have on a black knee length skirt with a white and black knit top. Nails are Revlon Red, have matching lipstick. Wearing black pumps with beige stockings and garter. Hoop earings and silver bracelets with red...
    ta61 ta61 51-55, T 10 Responses Jan 28, 2015

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    I got a pair of clip on 4.

    5 inch chandelier earrings in the mail today. I tried them on. Before I knew it, I was standing in the mirror, applying a dark coat of lipstick. I was already wearing panties, a bra, falsies, patterned black tights, foundation, eyeshadow, eyeliner, mascara and blush. It was like...
    jessicavamp jessicavamp 41-45, M 7 Responses Apr 17, 2015

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    I Am Right Now!

    I love doing the whole thing: tucking away the problem, slicking on the hose, pulling up the panties, hooking up the bra, lacing up the corset (especially this!), pulling on the skirt, buttoning up the blouse, slipping on the heels (as high as I can get), and then the make-up...
    jessicatv99 jessicatv99 41-45, M 10 Responses Jun 18, 2013

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    TheTrollinator TheTrollinator 13-15, M Aug 7, 2014

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    harnnes harnnes 31-35, M Apr 16, 2015

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    Second Day Out

    I started by painting my toes a bright purple then put on panties Sandles hoses a black bra stuffing it with water balloons. I put on make up for the second time in my life. It really takes a knack to do perfect make up. I then proceeded to put on a dark blue turtle neck a beige...
    gdmidd gdmidd 41-45 25 Responses Feb 13, 2012

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    I dress as often as I can get away with it.

    Yes I can pass but everyone knows who belongs where in RV park. Have had to leave a park once where I was seen by neighbors. I was fully dressed not drawing extra atten. Just the same neighbor complained to mgr and our stay there was over. Now I dress before Wife and I check in...
    tvcandi tvcandi 46-50 4 Responses Jan 24, 2014

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    I Like It To!

    I am 15 years old at the moment. From time to time (when my parents are gone) im putting on my moms lingerie and dresses, it makes me feel verry comfy. one day my mom caught ne wearing one of her tights under my pants, she didnt mind but the doesnt want me to tell dad about that...
    GirlyBoyy GirlyBoyy 18-21, F 1 Response Mar 11, 2013

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    In The Last 2 Years..

    In the last 2 years... I started exploring the Savannah side of me. First I met a woman as things developed between us i decided i would tell her about my feelings. and desire to show the feminine side of me. I figured if she wasn't receptive it would be she would run away...
    Savannah907 Savannah907 46-50 6 Responses Feb 8, 2012

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    I want a relationship with a crossdresser,

    sissyboy, ladyboy, shenail or just a girl that would go shopping with me dress me and just love me for me. If there is anyone that would want that message me.
    Ryan050606 Ryan050606 13-15, M Jan 26

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    I love the confidence I carry in femininity,

    the smiles I receive and the respect along the way and how I get to have my way easier. it is certainly a thing, to admire. The power of a woman.
    FierceFox FierceFox 22-25, F 5 Responses Jan 2

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    i looking for a big hard ****

    for suck it and ****.me all day :)
    laplay420 laplay420 18-21, T 1 Response Oct 20, 2015

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    So In Love With My Baby

    My boyfriend recently shared his secret that he likes to dress up as a woman... I was shocked at first but open to the idea, after a little experimentation I have realized that this woman has opened my eyes to the fact that no matter what kinda freak I was and all the things I've...
    DevotedSlave DevotedSlave 31-35, F 10 Responses Jul 9, 2013

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    Masterlicks Masterlicks 31-35, M Oct 14, 2014

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    Is der any kind open minded ladies/ girls dat

    are throwing away clothes in dublin. Wud be interested in takin them of ur hands. Iv began to dress up in ladies clothes. Especially sexy lingerie nd night dress. Love the feel of them. 0858430347
    neary2016 neary2016 26-30, T Nov 12, 2015

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    Now Mum Knows

    Last night I showed my mother my female side(Joanne). First I dressed in my French maids outfit, black and white very mini skirt and petticoat, black fishnets, black patent heels, auburn wig and full make up. Very nice ,was her first comment, you have lovely legs...
    JoanneTV2 JoanneTV2 56-60, M 12 Responses Sep 29, 2013

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    I'm dressed up right now.

    I have on bra,panties,pantyhose,a zip in back skirt,a string strap top,and high heels. I put on lipstick,eye liner,eye shadow,and I'm looking for the mascara. glitter nail polish.
    deleted deleted 26-30 3 Responses Jul 15, 2015

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    SeanaO SeanaO 22-25, F 2 Responses Mar 14, 2014

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    Oh, What A Nite

    this is the followup of my first nite out as Michele. I met my c/d friend at a motel that was close to the bar we were going to. we had plenty of time to get ready as we did not want to get there till around 8;00pm I arrived underdressed , then proceeded to get ready with...
    michelecd michelecd 56-60, M 8 Responses Sep 2, 2012

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    How It All Started

    It all started with a pair of mums stilettos, i was 9 at the time, i found them in the bottom of the wardrobe, i felt so good parading up and down the landing in them, over the following years i used to rummage in old clothes in mum n dads bedroom, dresses, swimsuits, knickers...
    jaquilinerose jaquilinerose 41-45, M 12 Responses Sep 8, 2010

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    As a real woman or lady,

    I love dressing up in a nice short dress or in a skirt with a nice looking blouse, appropriate and matching underwear, hose, and in my 4 inch high heels.
    businesswomanathome businesswomanathome 36-40, F 2 Responses Feb 15, 2015

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    I to love to dress like a female away from work

    in a short pencil skirt sexy blouse high heels with a 7 inch heel full makeup and ecrtto me this is a real thrillfor me
    wissers wissers 66-70 Apr 16, 2015

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    Dresses And Heels

    My favorite outfit to wear, a pretty dress and heels. I love to wear dresses, I feel more femme in one and myself think dresses are sexy. I wear dresses most of the time, I find them comfortable and fashionable. Add a nice pair of heels, a little makeup, and a girl is dressed...
    Raeka Raeka 36-40, T 15 Responses Oct 15, 2010

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    What A Feminine Experience

    When I was 13, a year after I started crossdressing, my mom decided to dress me elegantly as a girl. She let me wear a black cocktail dress with all feminine underwear underneath. She applied my make up and she let me wear a garter belt for the first time. She gave me a black...
    sharinep sharinep 22-25, T 13 Responses Jul 26, 2013

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    I really love dressing

    as a woman so far it's just been in the privacy of my home and a occasional hotel room but here is my dilemma I am engaged and she doesn't know how or what is the best way to tell her cause I would really love to have a girls night out with her
    Peggy491 Peggy491 46-50, T 3 Responses Nov 10, 2015

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    I don't wear makeup every day,

    but I do wear feminine clothing everyday, and have since I was about 16 years old.
    femininityforme femininityforme 41-45, T 1 Response Feb 27, 2014

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    Dressed For The Day!

    I went on a shopping spree this morning and got new heels, stockings, garter belt, bra and a dress. Been in them all day and finding it real hard to take them off. I feel so comfortable and so sexy that I can hardly stand it.
    LuvHighHeels LuvHighHeels 61-65, M 7 Responses Aug 3, 2013

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    deleted deleted 26-30 1 Response May 25, 2015

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    Caught By My Mum

    I was 17 years old and had been dressing up a few years in my mums clothes. I'd got a job and finally had money to by some of my own clothes. I used to work the early shift and was home from work regulary by midday. My mum never slept well and would always have a sleep around...
    Suziecrouts Suziecrouts 36-40, M 17 Responses Jan 14, 2012

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    There is nothing more exciting

    as getting all dressed up and just prancing around the house. I love being being girly in all ways.
    Jessica76 Jessica76 31-35, T 5 Responses May 17, 2015

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    I'm not real proficient at it yet

    and I haven't ventured out in public but I sure would like to
    CDKristiK CDKristiK 56-60, M 8 Responses Nov 25, 2014

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    There has always been something wonderful about

    not only crossdressing but being completely crossdressed. Hair styled perfectly, nails polished, body hair shaved off so I am smooth, make up done and of course frilly lingerie and a short dress with at least four inch heels. When I am dressed like that I feel so special and...
    amandatrane1 amandatrane1 51-55, T 6 Responses Jul 17, 2015

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    So today, do I wear my bridal gown,

    maids outfit or become little red riding hood? The voting is now open!!
    deleted deleted 26-30 11 Responses Jan 22

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    My favourite summer outfit Love Summer time

    here in Australia! Thinking of wearing my bikini by the pool when I get home but I do need someone to put on suntan lotion on my back?
    deleted deleted 26-30 2 Responses Jan 26

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    love to dress in women's clothing

    and under wear it is so existing for me and such a turn on I have not tried make up yet but love to try it it would be fantastic to share this experience with someone else I'm in Cambridgeshire uk
    janetjanet janetjanet 51-55, T 3 Responses Jan 22

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    this is all new to me I been hidden from every

    one I no I have been dressing in womaning clothing for about 15 year and yes it fantastic feeling ever hand up i love playing with my self when I'm dress up and I do think about someone else tuch me but I have not got that fare that not saying I would go for it . I have not try...
    deleted deleted 26-30 4 Responses Jun 7, 2015

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    Working Girl

    Because of where I work, I'm required to wear a skirt suitor pant suit everyday. The menhave to wear suits and ties. This was the greatest day of my life when they offered me a job. The owner of the galleries was well aware of my being a transexual, so when he said I would have...
    rachelbgoodman rachelbgoodman 41-45, T 17 Responses Apr 26, 2011

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    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels and definetly make up and I also secretly am attracted to masculine tough and hairy men
    deleted deleted 26-30 Nov 17, 2015

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    I want a girl to dress me

    and do all my makeup
    duprey101 duprey101 18-21, M 2 Responses Feb 8, 2015

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    I need 2 hold a couple breasts of a female 2

    set free the stress I’m not have. If I wasn’t that lazy I’ll get 2 the green bench on Bloodmountain by the Fleshhouse 2 make my needs of holding a couple femal breasts real. I know many places like the Green bench on Bloodmountain here in the heart of the most beautiful...
    Egolikeme69 Egolikeme69 46-50, M Nov 30, 2015

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