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I Go Out Crossdressed

Personal Stories, Advice, and Support 3,172 People

    I had to pop on and write this quickly.

    As you may know I came out to my parents about my dressing and desire to be a woman full time. We were opening gifts this morning and I received a beautiful back dress from my Mum, it's absolutely stunning. I actually cried and Mum said for me to try it on. It fits wonderfully...
    GirlyLisaTG GirlyLisaTG 31-35, T 9 Responses Dec 25, 2014

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    I had the most wonderful day today!

    I got up this morning did my normal beauty routine, and got dressed for the mornings errands. I had to get fuel for my vehicle, stopped at Starbucks, then picked up some other supplies for Christmas and went to Target. I was dressed fully en femme and love being the girly sissy...
    Bellringer2c Bellringer2c 56-60, T 10 Responses Dec 3, 2014

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    This Friday I am so excited.

    The wife and I will be going out for a full day of shopping and dining this Friday. Of course, I’ll be SarahAnn for the day. What makes it so exciting will be the outfit that I’ll be wearing. It’s probably my most feminine and most humiliating to wear. I have worn it...
    1SarahAnn 1SarahAnn 46-50, M 5 Responses Nov 4, 2015

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    I had such a brilliant night out

    as Lisa last night, had a lot of fun with my girlfriends. We did a lot dancing and quite a bit of drinking :) It was fantastic being out as Lisa and having such great friends who accept me as I am. A few girls came along who I have never met before and they were very curious and...
    GirlyLisaTG GirlyLisaTG 31-35, T 12 Responses May 10, 2015

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    lets have fun together.

    who's up for some cam play?
    mindcontroller mindcontroller 26-30, M 1 Response Dec 24, 2015

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    Last night I went to a gay bar

    which has a t girl night regularly. I had a fantastic night, I wore a black dress with black tights and heels. It felt wonderful being out. There was a lot of men interested in Crossdressers and I had a lovely chat with a man called James. We talked for a while and had a dance...
    GirlyLisaTG GirlyLisaTG 31-35, T 12 Responses Jun 26, 2014

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    Enjoying Being Dressed

    After my separation from my wife I started to live my life as I wanted to. I wanted to be a women and so I would dress my self up and go to Toronto even if I just wanted to go window shopping it was just so much fun. The best time I ever had going out dressed was when a Friend of...
    Samanthalynn101365 Samanthalynn101365 66-70, T 20 Responses Oct 6, 2009

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    In the beginning I guess I could have called it

    crossdressing but with the life lessons my wife has drilled into me my actions, movements, gestures, and appearance is now routine, nothing comes second nature I just do it without having to think how would a female act. It is no longer crossdressing it is my life.
    CdKimmi CdKimmi 66-70, M 5 Responses Nov 2, 2015

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    I finally did it! Tonight was the first time I

    went out dressed. It was just a small step but I felt like my heart was going to beat right out of my chest the whole time. So I am driving home from a business trip and happened to be passing through Atlanta right during the SCC. I got a room at the same hotel and immediately...
    Freja14 Freja14 36-40, T 17 Responses Sep 5, 2014

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    Last weekend I had to travel from one city to

    another. Before I ventured onto the train for a 2 hour journey, I plucked up the courage to change en-femme in the station toilets. I was really nervous, especially when I boarded the train & found there was no spare seats. I went to the buffet car for some dutch courage & was...
    chloesiobhan chloesiobhan 56-60, T 12 Responses Sep 4, 2014

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    last weekend I got pounded 4 times

    and sucked 9. I love the sex clubs in LA & LV.
    JackieCoxx JackieCoxx 51-55, M 1 Response Dec 20, 2015

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    Victorias Secret

    yesterday i went to the mall and ventured into victorias secret for the first time and was overwhelmed when all 4 sales girls dropped what they were doing to assist me. even a few of the customers wanted to help me look around for something i might like. the manager explained to...
    Mizsuzy Mizsuzy 46-50, T 5 Responses Dec 2, 2011

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    New Years Eve 2014 My wife

    and I have spent the three previous New Year’s Eve nights out of town at small hotels. Each of these hotels had a small lounge and a party to bring in the New Year. All of these were small affairs, and each one helped me gain confidence to go out in public dressed as a woman...
    1SarahAnn 1SarahAnn 46-50, M 9 Responses Jan 6, 2015

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    Trapped In Womens Clothes

    A few years ago I had the pleasure of having a female friend that helped me with my crossdressing. She would help me with makeup and getting dressed. The best thing is, she would also house my wardrobe in a closet in her house. Thus limiting my chances of being discovered. One...
    ka851 ka851 51-55, T 10 Responses Dec 1, 2012

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    These pictures are some of the latest ones of

    me out crossdressed and doing a show in front of a crowd.
    RobynTheBeautiful RobynTheBeautiful 41-45 6 Responses Sep 26, 2015

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    Wife out & child free.

    Going go 4 a walk legging and a top. Witch leggings tartan or just plan black
    deleted deleted 26-30 4 Responses Oct 23, 2015

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    I Finally Did It!

    Not that I lacked courage, I just had always thought it would be best if I did it with a friend who knew my secret that I crossdress. Of course I still think it would be more fun with someone but for whatever reason I not only worked up the amount of courage I lacked and just...
    STLCD STLCD 22-25, M 27 Responses Jul 17, 2012

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    Jman112299 Jman112299 16-17, M Sep 13, 2015

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    I've been out dressed a few times

    but the best was one night I was feeling very confident. So I went out to an 24 hour shop and went clothes shopping. I was wearing a nice top, matching bra and panties, short denim skirt, stockings, high heel boots, my wig and makeup and jewellery I looked fantastic ( well I...
    xdsophie xdsophie 36-40, T 15 Responses Sep 23, 2015

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    I decided to do sort of a crossdress dare to go

    in public without the possibility to chicken out. If you've read my previous story, I explained how I got caught and had to dress up as a girl to school. Al though I felt really embarassed, I just loved the feeling so much. I stopped crossdressing for a bit because my obviously...
    DCYDDON DCYDDON 18-21 8 Responses Aug 23, 2015

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    Happy New Year everyone :) I had a fantastic

    New Years Eve, I went to a party as Lisa which was just fabulous. The women were so accepting and asked so many questions which I enjoyed answering and it was nice to have some girly chats. Some of the men gave me some funny looks but nothing I couldn't handle, was expecting a...
    GirlyLisaTG GirlyLisaTG 31-35, T 9 Responses Jan 1, 2015

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    MacroCaptain MacroCaptain 22-25, M 2 Responses Dec 31, 2015

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    I'm going out tonight

    as Lisa with some girlfriends, I'm so excited. I will be wearing a royal blue dress with nude tights and nude heels. It's going to be a great night :) It is so much more fun getting dressed to go out as a woman than just throwing on a t shirt and jeans. I love being Lisa :)
    GirlyLisaTG GirlyLisaTG 31-35, T 11 Responses May 9, 2015

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    When I go to work I wear my leggings till I get

    2 work and put my pants on in the car on top of them... last 2 morning s I've been going in earlier and not putting my pants on strut away I'd been walking 2 thr smoking hut in leggings having a tab and walking bk to the car.. yesterday a lass I work with said.. I thought u had...
    deleted deleted 26-30 Sep 24, 2015

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    I Have A Boyfriend that goest Out Crossdressed

    Ok! Iam Female by birth, and i have a boyfriend that loved to go out in public crossdressed, I found out by accident and admit at the time I didnt take it to well, I felt betrayed and threatened, not to mention angry as i felt he didn't trust me enough to express his feelings...
    pashon8 pashon8 41-45, F 20 Responses Oct 29, 2012

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    Yesterday, while driving,

    I took off all my clothes on my way to a rest stop outside of the city. I parked at the rest stop, since there was no one else, I sat at a table with my clothes in hand. I put on black high heels with peep toe, tan thigh high pantyhose, and a short black dress. As I walked...
    lascruces1971 lascruces1971 41-45, M 4 Responses Oct 21, 2015

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    I'v been dressed up all day.

    .but did not get a chance to go out..:( sill I feel good.
    Shelly6395 Shelly6395 36-40 2 Responses Oct 25, 2015

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    I had a great night out on Saturday in Lisa

    mode :) it felt so natural and right to be out as the person I should be full time. I was dressed in a little black dress with nude tights and black heels, I felt wonderful :) This may sound small but the biggest buzz came at the end of the night when me and a few...
    GirlyLisaTG GirlyLisaTG 31-35, T 11 Responses Jun 16, 2015

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    can't whate for Holloween I'm going to dress up

    for the day:) In my costume like the one in my pic..but one step ferther I'll put on fake nails I'v always wanted to were those and fake eye lashes all the make up too..I love Holloween :)
    Shelly6395 Shelly6395 36-40 7 Responses Oct 24, 2015

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    I long for the day when i can post in this group

    that i have gone out dressed. But im still in the closet, i have even tried to come out.. but just nothing has worked. Im far too afraid to tell any of my friends, as i dont really have any friends who are girls, all mostly boys and they wouldnt understand. I have even tried...
    Sarah147 Sarah147 18-21 5 Responses Oct 26, 2015

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    My First Time Out As Annie

    I found a crossdresser group that meets once a month thats not too far from me. Its run by a woman who has a web site for CD's & i went to a makeup class she does. I was with 8 other CD's we changed at her house & spent 2hrs learning makeup, I learned alot. I ageed to go to the...
    meflash meflash 51-55, M 28 Responses Nov 30, 2010

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    sometimes,at night, i put one short dress on,

    my heels. do some make up and my long black wig and get into my car for a night drive. where i live there are some roads that are not very used and i get out and smoke a cigarrete by the car. every now and then a truck will pass. is in that moments that i really enjoy beeing...
    imlimacd imlimacd 36-40, T 10 Responses Oct 21, 2015

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    One summer while at the beach in SC

    when I was early in my cross dressing experience and very horny looking at at all of the girls in their bikinis. I had been wearing my sisters panties for years. I had also been flash the girls next door acting like I was drying off from my shower. One night I decided to go for...
    rachaelbalenger rachaelbalenger 46-50, T 2 Responses Sep 18, 2015

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    deleted deleted 26-30 1 Response Nov 2, 2015

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    Walking from my mam and dads it's about a mile

    and I walking it in leggings and I live in the town center.. its going be the longest I've walked in leggings b4... way out of my comfort zone
    deleted deleted 26-30 5 Responses Oct 3, 2015

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    My First Time Crossdressing In Public

    Note: I already wrote about this experience in a different story, BUT I didn't go into detail about being outside in public. So I wanted to write this to cover that part of my amazing night. I'm copying the first paragraph so you can understand the context but then I'll go into...
    iheartdressing iheartdressing 26-30, M 22 Responses Jun 8, 2013

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    So I wore my mini Goth skirt

    and a tight jacket with a push up bra just to take out the trash :D
    Burstangelxxx Burstangelxxx 26-30, M 1 Response Sep 16, 2015

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    So in my last experience I asked people on what

    I should wear and there was an overwhelming response for choice number 2!! So today I wore just that, but without the white skirt, just a red polka.. Weather was a little windy and I managed to get a little shopping done before retuning home for some tea hehe :) Thanks for...
    maddylim maddylim 18-21, M 6 Responses Jan 24

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    two nights this week I went out.

    Both times in shiny wetlook leggings and 4" heels. It was so much fun!
    bethluvshose bethluvshose 31-35 8 Responses Oct 10, 2015

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    let's have fun together!

    add me and write me you are a crossdresser
    mindcontroller mindcontroller 26-30, M 1 Response Dec 20, 2015

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    My first time out dressed was a number of years

    ago. Prior to this my dressing was at home, both in the closet. and when I finally came out to my wife. After a period of dressing at home in my wifes presence the desire to go out dressed increased, and after discussion I decided to make my first visit to a local trans...
    MandytgAndy MandytgAndy 70+, T 8 Responses Feb 11, 2015

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    I had my second appointment at the gender

    clinic yesterday, I was finally put on hormones and will be starting my real life experience over the coming months. I went as Lisa as I wanted to portray the real me, I wore a red maxi dress and sandals :) It was a very intense appointment and a lot of emotions and tears. It...
    GirlyLisaTG GirlyLisaTG 31-35, T 8 Responses Jul 17, 2015

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    I Shaved My Legs Today For The First Time!!! <3

    I am really happy and excited to tell you guys that for the first time in my life, i have shaved my legs :). I am wearing nude tights, with a denim skirt and heels and my legs have never felt so good in my life! I really do not know why i waited so long to try this but i regret...
    TorquedStudios TorquedStudios 18-21, M 29 Responses Dec 12, 2011

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    Been thinking this one through

    for a few weeks, maybe months actually and have shared the thoughts with other CDs on EP...last night my wife had a meeting that would going late into the evening and would not be home until well after 9 pm....after rush hour passed, I put on one of her short skirts, white long...
    Nikkihughes46 Nikkihughes46 56-60, M 13 Responses Sep 19, 2014

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    The ladies at Monica’s Flowers store

    treated me so nicely! They referred to me as “she” and “her” so naturally, and I felt much better about myself again. Then I saw myself on one of their security cameras and felt some disillusionment reappear. I am just way too muscular around my upper...
    chrissymendelssohn chrissymendelssohn 31-35, M 5 Responses Nov 13, 2015

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