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I Went Out In Womans Clothes

Personal Stories, Advice, and Support 563 People

    Dressed In A Skirt

    I was very excited the other day because I knew that I would be out and about in a skirt. I first laid out my outfit on the bed a nice all black above the knee skirt, my shiny gray leggings,got into my wifes closet and pulled out a very nice black zip up sweater. I slipped into...
    skirt12 skirt12 51-55, M 2 Responses Dec 16, 2012

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    Today I'm going out wearing women's underwear.

    I've got my diaper(nappy). Plastic panties with a pair of pink flowered cotton panties. I also have a pink flowered bra on aswell. But unfortunately I have to wear ugly men's bland clothes on top.
    babyannie57 babyannie57 56-60, M 1 Response Aug 21

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    sexyaime sexyaime 26-30, M Mar 21

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    A Nice Little Treat..

    .Yesterday my wife & I went shopping. I wore ladies jeans, a pretty pink striped blouse, loafers, jewelry, and light makeup with lipstick, and carried a nice shoulder bag. We left home mid-morning to avoid large crowds. Upon entering an upscale jewelry store, an attractive 40...
    janusatv janusatv 61-65, T 3 Responses Dec 4, 2013

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    It Is So Much Fun.

    I have lost count of the times I have been out in public dressed as a woman in the last few years doing lots of stuff from shopping to nightclubbing.I am almost 'owning it' and what a feeling that is.
    RobynTheBeautiful RobynTheBeautiful 41-45 Aug 30, 2013

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    Women'S Oxford Shirts

    I consider myself a casual crossdresser, so any women's clothing that looks androgynous interests me. One of those are Oxford shirts. They look like men's shirts, except with a feminine cut at the waist. I just bought myself a light blue shirt online. When it arrived, I was...
    val83 val83 26-30, T 3 Responses Mar 18, 2013

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    Out In Womens Clothes

    I wear womens clothing every day. 97% of my wardrobe is womens clothing, including 7 pairs of shoes. Along with my Plunge Bra, panty, cami, and hosery, a nice feminine top and jeans or womens dress pants.I don't try to pass, but be comfortable in clothing I like to wear. I like...
    serinalynn serinalynn 61-65, M 1 Response Sep 24, 2012

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    The New Me

    I am transgender and for the past six months I have been living happily as a woman named Teri. I put all his things in storage and would consider it crossdressing if I ever have to wear them again. I just love my new life and plan to live the rest of my life as Teri. I have...
    PinksWoman PinksWoman 61-65, T 11 Responses Mar 7, 2013

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    let me start by saying,

    I am NOT passable!!! well this morning, I had to go to the clinic, nothing bad!!! just blood for my cholesterol check, nothing wrong! lol! so I got up, shaved my face and legs, put on some Suave cherry blossom anti-perspirant (I just LUV the soft girly scent) a tight bra...
    JessicaMann JessicaMann 41-45, T 4 Responses Jun 14

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    Going Out With Other Crossdressers...

    When I first discovered the internet, I was happy to discover that there were many guys like me -- guys that liked to dress in women's clothes. I met a cd'er on line who told me that he and a bunch of friends rented an apartment that they used for dressing in private and for...
    driver88 driver88 46-50, M 2 Responses Nov 1, 2012

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    Went Out In Everything Female

    last weekend i was home by myself doing some work around the house as usual i was dressed in my cute pink shorts with pink leggings underneath and a cute little low cut skin tight tshirt underneath i had on a sexy see through white bra. anyway it was late afternoon and i decided...
    jarviscooper jarviscooper 36-40, M 4 Responses Jul 7, 2012

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    Camden Lock

    I had not long acknowledged to myself that I was CD and I wanted to see what it was like wearing a skirt out. For my trip I chose a black shirt and jacket, long charcoal grey socks and back brogue shoes. In my black rucksack I had my knee-length dark grey merino wool skirt to...
    meganb1 meganb1 36-40, T 4 Responses Jul 29, 2013

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    Beverly Hills 90210

    The other day I had an appointment with a plastic surgeon in Beverly Hills. It was to discuss options for facial feminization, so I decided to go as Genivieve. I shaved and showered did my make-up tastefully light and picked out a simple black bra and panty set. This bra...
    genivieveleduc genivieveleduc 46-50, T 6 Responses May 25, 2013

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    I Wore A Skirt And Sweater Out The Other Day

    I wore a skirt and cute sweater to the bike shop. A very nice black above the knee with panties. A very nice v neck sweater with a scarf. The folks at the bike shopm handled me with respect and I made a purchase for my wife. From there I drove to Wisconsin to buy some New Glarus...
    skirt12 skirt12 51-55, M 2 Responses Dec 6, 2012

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    Walking In A Public Park

    I've dressed in a wig, makeup, bra, girdle, tight-short gym shorts and nylons and walked in a public park for hours. I stuffed my bra with water filled balloons and bounced up and down for walkers to see. It was so exciting! Satisfying
    satisfying satisfying 70+, M 4 Responses Nov 24, 2013

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    Out In A Skirt

    I finally wore a very colorful mid thigh skirt out the day, until now I have only worn mid thigh all black conservative looking skirts well this one has beautiful paisely shaped flowers 7 bright it colors in all including pink, coral , yellow and magenta. I did get a nice comment...
    skirt12 skirt12 51-55, M 3 Responses Dec 18, 2012

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    This Morning

    When I walked out to my patio, it was covered with leaves from the rain and wind storm we had last night. I swept it off and then thought "I bet the carport is covered too" I walked to the carport and it wS so I dressed on nightgown swept off my carport in full view of my...
    deleted deleted 26-30 3 Responses Jul 22, 2012

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    Related Experiences

    I love seeing my belly grow bigger both from my baby growing and all the delicious food I've been eating turning to soft, jiggly fat :) Most of my clothes no longer fit me, and...
    bombsarenotmusic bombsarenotmusic 18-21, F 3 Responses Dec 14

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    I am officials having to wear size 38s now so much more room for now. The 34s are going out.
    Chubbyhubby230 Chubbyhubby230 31-35, M 1 Response 3 days ago

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    Noticed my tshirts are starting to ride up and letting my belly hang out a little now wow growing bigger
    Chubbyhubby230 Chubbyhubby230 31-35, M 2 days ago

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    Haha first dates are always awkward for most but I'm always calm for some reason. It wasn't my first date ever but it was fun, we went ice skating and ate crêpes. X) What have...
    Allyyoop Allyyoop 16-17, F Dec 6

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    I made a bet with a girl. I won't go into what the best was about, but things escalated. I ended up losing the bet, so I had to go outside naked and take a picture of myself as...
    SerSean SerSean 18-21, M 1 Response 2 days ago

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    Back in my day we used to do all sorts of silly crap outside. I miss those nights playing manhunt or riding around the neighborhood on our bikes with water guns pretending we were...
    DerelictThought DerelictThought 22-25, M 1 Response 13 hrs ago

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    I live alone and cannot pass as female. At home I wear skirts or dresses, stockings and heels and sleep in a nightgown.
    cdchrystal cdchrystal 51-55, M 4 Responses Dec 6

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    I have dressed up all my life in one way or another, for *** long as I can remember. Back in school I loved dressing in my panties and shorts never minded the comments, some wear...
    mattie23 mattie23 51-55, T 1 Response Dec 8

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    I wear n love wareing womens brief nylon panties
    howard1945 howard1945 51-55, M 1 Response Dec 9

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    I really love wearing womens brief nylon panties since i was in my early teens i really love n enjoy wearing them to this day im 55 yrs old but the is a true conversational...
    howard1945 howard1945 51-55, M 1 Response Dec 9

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    I was hoping to get some sun on my naked body but the combination of a cool temperature and a stiff breeze quickly discouraged me and I didn't last long. I love days I can tan in...
    xxxtop xxxtop 36-40, M 4 days ago

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    I am wearing womans clothes. My pantys can be seen through my tights tommorrow i will buy some kinky clothes so my boyfriend can be shocked by how hot I am
    Sophiejordan1 Sophiejordan1 18-21, T 3 days ago

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    I work from home and my wife also works, but with a company I don't particularly care for, and my step-daughter goes to high school. She likes me and it's actually like she's my...
    ThomasLuuk ThomasLuuk 18-21, M 1 Response Dec 14

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    Sooo.. How did it happen? well so far I have only come out of the closet with my wife. But that began about 4 years ago. It should be noted that i have dresses off and on in...
    MsMarcy MsMarcy 41-45 4 Responses Nov 30

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    It is a beautiful sunny day....with a few flurries in the air. I was just outside to hang some laundry on the clothes line. It is so nice to have this opportunity, as I live in...
    sunnycaramelo sunnycaramelo 46-50, F 1 Response Dec 20

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    I'm a 14 year old boy and in 8th grade. I'm really small for my age, and people often mistake me for a 4th grader because I'm only 4'-7" and weigh around 80 pounds. Mommy gets my...
    littlebobby6 littlebobby6 13-15, M 3 Responses Dec 4

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    I do this at least once every year, where I go to school barefoot.In my kindergarten year it was fun. We had a pajama day, and that's the day I chose to go barefoot. So, that...
    Barefoot1999 Barefoot1999 13-15, M 5 days ago

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    It was yet another thunder night on 15/12/2014 and my sister came to sleep in my room and kindly requested for more tickling. I agreed like i always do and will. I tied her hands...
    Delphi111 Delphi111 13-15 3 hrs ago

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    When I was in middle school, I used to always get jealous of the kids who could go hang out with their friends freely. It didn't affect me so much then but it really does affect me...
    uh2behonest uh2behonest 16-17, F 6 days ago

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    This is a photograph of me in a London hotel room a few minutes before I went out for a walk around Charing Cross Road and Leicester Square, including a visit to a bar in Lisle...
    clairemeredith clairemeredith 46-50, T 3 Responses 5 days ago

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    I love to go out as a normal woman of my age, I went out Thursday night to the supermarket shopping, after many years of practice no reaction from anyone......such a frill
    amber8642 amber8642 51-55 3 Responses Dec 13

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    When I was a freshman in middle school I was a straight A's student. At the end of the second term, the principal came to my class to talk to me and she announced that I had won...
    nowherewego nowherewego 16-17, F Nov 29

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    Went out back on deck last week. Pulled down pants and stroked in the crisp air.
    SebastianoftheRealm SebastianoftheRealm 41-45, M 1 Response Dec 12

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    Swimming fully clothes is always something I had wanted to try growing up, but i just never had the right moment to do so. One day home from college, I went over to see one of my...
    Ravenboy90 Ravenboy90 22-25, M 1 Response Dec 10

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    Its a bit further than Stancombe wood from where i use to live in Winchcombe an the other direction buh on a nice warm day in the summer hols i didnt mind the walk :D So one day i...
    XXmelanieeXX XXmelanieeXX 18-21, F Dec 15

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    My friend said I could come over since her parents were out of town for the whole week. I went home with her and she asked me if I wanted to swim. I loved to swim so I said yes...
    ForcedToDress ForcedToDress 22-25, M 1 Response Dec 11

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    So more childhood life stories- So it was a basic day like any other but it was very very strange. It was a summer vacation weekend and Amanda hadn't said or done anything girl...
    Timelord47 Timelord47 18-21 3 Responses Dec 12

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    I read **** on the internet and so I have made for you a fake story that is not real in any way possible. It's a very peculiar story so I hope you enjoy it. And remember I am only...
    Timelord47 Timelord47 18-21 a week ago

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    Im a 18 year old boy who has just finished high school. Ive always loved the idea of wearing girly clothes as they are often really cute and nice.. im always checking girls out but...
    Giles2142 Giles2142 16-17, M 1 Response 4 days ago

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    I spent the whole day crossdressed in public today. Well not the whole day since I didn't leave the house till 1:30. I started out by going and playing bingo, which I do every...
    Michelle1976 Michelle1976 36-40, T 2 Responses a week ago

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