Post
Experience Project iOS Android Apps | Download EP for your Mobile Device

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

Personal Stories, Advice, and Support 3,256 People

    Dressing Is What I Do ,i Am A Normal Straight Male

    I love dressing as a woman. I have dressed since i was 9 or 10 yrs old in secret. I came out when i was 18 to my girlfriend who is now my wife. We have been together for 38yrs , married for 36yrs. I am 56yrs old. I told others acouple years later. I started going in puplic...
    cindyloulove cindyloulove 56-60, M 7 Responses Jan 4, 2011

    Your Response

    Cancel

    I'd like to hear what you like about it

    and see some pictures. Message me for my email.
    ar29605 ar29605 22-25 1 Response Feb 9

    Your Response

    Cancel

    Since Then. Part 1

    The first time in my life that I've ever let anybody see me dressed as a woman in person, was just a couple of weeks ago. I've tried to play it out in my mind before, and never thought I would be able to go through with it. When my girlfriend asked me if I wanted her to do my...
    free2bFreya free2bFreya 31-35, M 1 Response Jul 18, 2013

    Your Response

    Cancel
    Maxxymo Maxxymo 22-25, M 2 Responses Jan 2

    Your Response

    Cancel

    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 9 Responses Sep 2, 2012

    Your Response

    Cancel

    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 14 Responses Sep 29, 2013

    Your Response

    Cancel

    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 10 Responses Jul 26, 2013

    Your Response

    Cancel

    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

    Your Response

    Cancel

    I can feel sexy in other clothes too.

    :p But I do like wearing dresses, heels, skirts and other fun stuff.
    StockholmblondiE StockholmblondiE 22-25, F 2 Responses Oct 14

    Your Response

    Cancel

    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 26 Responses Feb 13, 2012

    Your Response

    Cancel

    Friday

    Home from work, can't wait to shed my boring clothes and go through the process of becoming someone sexy and exciting! Looking forward to getting smooth, padding around in my stockings, putting on some boots, zipping up into a tight dress, pulling out my makeup and brushes and...
    Allisonvamp Allisonvamp 36-40, M 6 Responses Nov 2, 2012

    Your Response

    Cancel

    Acidmix Has Been Launched For Halloween : Shoutout Party Lovers

    AcidMix has been launched for Halloween : Shoutout Party Lovers Hi all, just thought to let everyone know, for Halloween occasion I have created a new conceptual way of looking at cross dressing as regular activity every weekend for either gender being bi sexual, please also...
    cross2play cross2play 31-35 Oct 17, 2013

    Your Response

    Cancel

    Who's The Wife? I Think It Might Be Me.....

    Today my wife left again. It was only a matter of time. I am certain she went to meet her new boyfriend. She didn't have to say it I saw it in her eyes, she wanted a man not gurl wanna be. A part of me didn't want her to go but there is nothing I can do. She knows as soon as she...
    marcycd12 marcycd12 41-45 10 Responses Sep 1, 2013

    Your Response

    Cancel

    Dandia Nite Masti

    This year Dandia night i feel an amazing experience with my friends. It was Thursday, My friends planed to go for dandia night. one of my friends call me and ask me to go with them. they all are girls. On that afternoon they all reach my home. They say me i have to go with them...
    lizaranid lizaranid 22-25, T 4 Responses Oct 28, 2012

    Your Response

    Cancel
    TheTrollinator TheTrollinator 13-15, M Aug 7

    Your Response

    Cancel

    Not as much as I use to,

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

    Your Response

    Cancel
    sexhot31 sexhot31 18-21, M 6 Responses Apr 26

    Your Response

    Cancel

    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

    Your Response

    Cancel

    My Dressup Story.

    I am a boy, i wear girls dresses at home. no one knows about it. one day my aunt come to my home and see me with a skirt and top with earring and bangels. she asked me what is this? i feel shy and say her that i wear dresses at home. then my aunt ask me to come with her. we both...
    lizaranid lizaranid 22-25, T 41 Responses Jan 8, 2012

    Your Response

    Cancel

    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 41-45 2 Responses Jan 24

    Your Response

    Cancel

    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

    Your Response

    Cancel

    My Older Sister Cautgh Me In Her Dress

    This happened years ago,  I was 13 at the time my older sis was 17, i had stayed home from school sick I had the house all to my self Mom and Dad had gone to work my younger and older sister went to school. I would sometimes sneak a pair of my sisters panties out of the hamper...
    eyesofblue77 eyesofblue77 61-65 1 Response Jan 11, 2012

    Your Response

    Cancel

    My biggest question is

    why would you want where High Heels, its probably most redundant designed article, and many reaserch show it can easily destory your feet http://www.medicalnewstoday.com/articles/265411.ph and just to ruin your fun further, they were not designed originally for women, but men...
    gypa gypa 26-30, M 1 Response Aug 7

    Your Response

    Cancel

    Dress At My Girlfriend's Home

    1 year ago, one day my mom tell me to bring some potato from nearest shop. in that time i was in a pink frock. My mom do my hair a ponytail. and wear me some kajal in my eyes and give me a pink ladies sandals to wear. when i was about to reach at that shop, my girl friend saw me...
    lizaranid lizaranid 22-25, T 7 Responses Jan 15, 2012

    Your Response

    Cancel

    I Luv Being Dressed In Girl Clothes

    Self as Individuals Living in Cosmopolitian city away from home  Link http://youtu.be/xYEO0Z0IL3I This topic is interesting but another angle for cross dressing or being a trans gender person is living and surviving if "all else fails" for individuals or from point of "no return...
    cross2play cross2play 31-35 Mar 14, 2013

    Your Response

    Cancel

    Since retiring I have done private tutoring to

    a small group of individual students. Since retiring also, I have been living full time as a woman so it follows that I am seen by students and parents as a woman. None have ever intimated that I am anything else and I love it. I dress as any city girl of a certain age would...
    josilver josilver 56-60 5 Responses Aug 16

    Your Response

    Cancel

    Her And I

    My experience starts with a confession to the one I love. My apprehension to approach the subject burned at my consciousness for weeks until I finally could take it no more. Sometime around 3 am my restlessness had awoken her, softly she asked" what's going on baby?" I hesitated...
    free2bFreya free2bFreya 31-35, M 2 Responses Jul 9, 2013

    Your Response

    Cancel

    My New Conceptual Information Of Cross Dressers OUT OF BOX

    My new Conceptual Information of Cross Dressers OUT OF BOX Conceptual Videos Playlist Sequence http://www.youtube.com/playlist?list=PL2Hm9UCVzJC-kKPtB5pJQZClwBVAlrGu9 I thought I produce a innovative school of thought besides from changing clothes to dress up as women basics...
    cross2play cross2play 31-35 1 Response Aug 27, 2013

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    Just Simply

    I love to dress as a woman because it is me, the higher the heels and the more feminine the dress the better :) also a lovely foofy petticoat and bullet bra to match :)
    dressprincess dressprincess 41-45, M 2 Responses Jul 25, 2013

    Your Response

    Cancel

    Crossdressing

    I am a 13 year old boy. I am not gay but i like to cross-dress as much as possible. Nobody knows about me cross-dressing. I would like people to know but i am afraid people will not understand. Today my mum is at work and i am alone in the house. I have been in my mums dresses...
    joshuajoanne joshuajoanne 13-15, M 6 Responses Oct 22, 2013

    Your Response

    Cancel

    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

    Your Response

    Cancel

    I'm not real proficient at it yet

    and I haven't ventured out in public but I sure would like to
    CDKristiK CDKristiK 51-55, M 9 Responses Nov 25

    Your Response

    Cancel

    My year of wearing / dressing up

    as girl in 2013 review After on & off living as a girl I thought to start uploads once again. The year was very mixed with several different activites but feel I did move forward in cross dressing field yet retaining my original state of gender. At this point it is getting...
    cross2play cross2play 31-35 1 Response Jan 6

    Your Response

    Cancel
    SeanaO SeanaO 18-21, F 2 Responses Mar 14

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 16 Responses Oct 15, 2010

    Your Response

    Cancel

    Look Little Girly In Public

    I am a boy love to dress and makeup as a girl. Sometimes i dress fully girly at house. i enjoy the feelings of girls dress. sometimes i experiment new things on me like new dresses, new makeups. I found some dressup and makeup for boys on public without very much attention of...
    lizaranid lizaranid 22-25, T 3 Responses Apr 8, 2013

    Your Response

    Cancel
    Masterlicks Masterlicks 31-35, M Oct 14

    Your Response

    Cancel

    I don't wear makeup every day,

    but I do wear feminine clothing everyday, and have since I was about 16 years old.
    cdbttm4top cdbttm4top 41-45, T Feb 27

    Your Response

    Cancel

    Volunteer Day This past Saturday was probably

    the most feminine day of my life. I was wearing my favorite brown plaid jumper with a black turtle neck, black patterned tights and black wedges. This particular jumper is a bit shorter than usual and ties in back . It feels so pretty. My hair and makeup came out very nice, and...
    1SarahAnn 1SarahAnn 46-50, M 3 Responses Feb 19

    Your Response

    Cancel

    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 56-60 7 Responses Aug 3, 2013

    Your Response

    Cancel

    Dress Up

    Im a crossdresser but got no stuff to wear looking 4 help plz if u can olz help by giving money of sendin old high heels
    crossdresskatie crossdresskatie 22-25, M Aug 11, 2013

    Your Response

    Cancel

    Related Experiences

    So many years ago, I had one of my first experiences wearing women's high heels. My family had gone away for a holiday, and because of clubs I was in, it was decided that I could...
    wistfulmiles wistfulmiles 51-55, T 3 Responses Dec 3

    Your Response

    Cancel
    I love nothing more than the feeling of slipping into a pair of sexy 5-6 inch high heels and touching myself. My ******* are mindblowing.
    hhfetish hhfetish 22-25, M 1 Response 3 days ago

    Your Response

    Cancel
    I only wear corsets on special occasions. They make me feel very sexy and feminine especially with nylons and high heels. I find they are too restrictive for everyday wear but I...
    kirsten29 kirsten29 26-30, F 1 Response 1 day ago

    Your Response

    Cancel
    I too am a straight guy and I have about 9 pairs of heels. I've been wearing them for years in private. One of my ex girlfriends used to let me crossdress fully and I loved it, we...
    Luvnheels Luvnheels 51-55, M 6 Responses Dec 6

    Your Response

    Cancel
    Ok, I've brought some boots this past few months, and I'm very much a sucker for nice looking and sexy boots. I love how they feel, and how they alter the way I walk depending on...
    blindfoldstacy blindfoldstacy 41-45, T 2 Responses Dec 8

    Your Response

    Cancel
    Didn't think I would actually ever share this but yes I do. I keep it low key and only wear them outside when no one else is around. I have no interest in wearing any other form...
    jambo33 jambo33 51-55, M 1 Response