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I Go Out Crossdressed

Personal Stories, Advice, and Support 2,850 People

    A dream come true..An actual encounter with a

    woman that lead to an exciting and fun evening.
    Cassiegurl Cassiegurl 36-40 3 Responses Oct 23, 2014

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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 26 Responses Nov 30, 2010

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    Dressed up as a slutty maid (lots of pictures

    ;P)i only recently started wearing lingerie but yesterday i was able to go into a fantasy of mine: being turned into a maid.with a thong-back onepiece and net pantyhose. I'd love to be forced to wear this and come to clean someones house while my master or mistress watches. As...
    leotardi leotardi 22-25, M 7 Responses Dec 2, 2014

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    Out For Lunch

    OMG I'm so excited! I just went out fully cross-dressed!I wanted to go out without my car for an extra thrill: it was too easy to just jump in the driving seat and dash off somewhere "safe", so this time I walked out the door.Now let's get this straight - I was trying to look...
    jessicatv99 jessicatv99 41-45, M 22 Responses Sep 18, 2012

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    You don't have to like me.

    You just have to want me.
    stamfordfan stamfordfan 41-45, M Nov 1, 2014

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    Finally did it! Went to my friends house

    and try did my makeup and then we went to the mall were I bought some cute panties at Victoria's Secret. :3
    Kimmandra6918 Kimmandra6918 18-21, T 8 Responses Jul 28, 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, M 9 Responses Sep 4, 2014

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    Need Some New Shoes!

    I've just been out for another lunchtime en femme. This time I went to a local town which has a small mall, so I wore my killer heels. I strolled around the mall very slowly, trying to look natural and feminine. Those heels are 5½ inches high, so after a while I was working...
    jessicatv99 jessicatv99 41-45, M 9 Responses Dec 18, 2012

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    Sorry if I misspell something,

    this is new for me. Okay... So a few weeks ago I was going to get dressed in the morning but I had no shorts to wear that day. I went to the dryer and got the clothes from there and placed them on the bed. Since our clothes are washed together I saw a few of her bras. It was...
    ErickHernandez ErickHernandez 13-15, M 6 Responses Oct 7, 2014

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    I haven't gone out fully dressed in years.

    Went through a big purge and haven't had the money to buy new clothes. The last time I did went to the mall and no one ever suspected. I even got complemented on the blouse I was wearing.
    AmandaM02 AmandaM02 36-40, T 4 Responses Jul 31, 2014

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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 23 Responses Jun 8, 2013

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    PART 2 of 2 When she arrived I was on the couch.

    .. Waiting. She sat down next to me and told me that she had found my growing pile of feminine underwear in the back left corner of my closet. She then went on about how she read some of my text messages to my girl-friends thanking them for the clothing and how they feel. She...
    ErickHernandez ErickHernandez 13-15, M 2 Responses Nov 23, 2014

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    I always wear short skirts

    when I go out. I usually wear them with a bra and a blouse. I prefer thigh high stockings but sometimes wear pantyhose. My heels are usually 4-5 inches. Strappy heels are my favourite but I haven't found any sexy ones in my size. I always go out with a girlfriend. We'll be in...
    stamfordfan stamfordfan 41-45, M 1 Response Oct 29, 2014

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    I love thigh high stockings

    that come all the way up to my crotch.
    stamfordfan stamfordfan 41-45, M 2 Responses Nov 1, 2014

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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 14 Responses Sep 19, 2014

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    Laundry Mat

    So it was Saturday morning and I needed to do my laundry. The washer was out of order in my building so I decided to gather up all my dirty clothes and take them to the laundry mat. Since I'm crossdressed daily a lot of my laundry is fem:panties, leggings, bras, etc. I decided...
    StevieTV StevieTV 46-50, T 3 Responses Oct 29, 2011

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    I was in a restaurant with my girlfriend.

    Some man came over to flirt with us at the table. I told my girlfriend I was going to the bathroom. We usually go there together. As I walked away I heard the man comment on how I looked so nice. I was wearing a jacket and skirt. My bra was visible in the jacket. My skirt was...
    stamfordfan stamfordfan 41-45, M 2 Responses Oct 29, 2014

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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 32 Responses Dec 12, 2011

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    I Love to go out dressed

    as a tart. All black. Panties, open girdle (with suspenders), panties(usually a thong), bra (silicon implants), t-shirt, fishnet stockings, and mini-skirt, black leather coat if cold, patent shoes. Have met several men, would love to meet a lady. Hugs Debbiestockings
    debbiestockings debbiestockings 56-60, M 3 Responses Sep 8, 2014

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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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    Out With The Girls!

    I was sitting with my wife , she is very open minded ., and the neighbor lady came over . we were chatting when I desided to tell her about Connie . She couldn't wait to see me crossdressed so I told her to come bye on saterday afternoon to meet her. She came over and couldn't...
    connie2much4me connie2much4me 56-60, T 4 Responses Dec 17, 2011

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    Running Errands

    While I'm a regular out and about crossdresser. i don't always crossdress. But when I have to run certain errands I get dressed and out she comes. I go to the drive-up window at the bank, Do the self service gas and as we all know you have to pay first. I go to my insurance...
    femboy4u femboy4u 22-25 5 Responses Apr 28, 2011

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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 5 Responses Dec 13, 2014

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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 19 Responses Oct 29, 2012

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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 5 Responses Jan 6

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    As of Tuesday I have finally admitted

    that I want to wear womens clothes whenever possible. My mom is very excited, actually it was a bit too much, and starting Monday she has decided that I will wearing entire outfits to school, this includes shapewear. I'm not as excited as you may think because I'm going to be...
    ErickHernandez ErickHernandez 13-15, M 1 Response Nov 30, 2014

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    Interesting Holiday Story My wife

    and I were able to get out for a couple of weekends of Holiday fun recently, and had some very interesting experiences while I was dressed as Sarah. The first one was at a Holiday comedy play that was produced by an amateur theater company in a small town about an hour north of...
    1SarahAnn 1SarahAnn 46-50, M 3 Responses Jan 4

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    2014 Review 2014 was a year of firsts in my

    crossdressing adventures, as I was able to go out dressed for a new record number of hours. Some of those extra hours were those that I spent working as a female volunteer. This was probably the most exciting development for me in 2014. The acceptance and freedom that I felt is...
    1SarahAnn 1SarahAnn 46-50, M Jan 4

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    This story will probably bore people,

    but it was a fun night for me. I went to my first movie as Julie Ann. It was great. I started the day by having a makeover from a MAC store up in Boulder. The lady that does it is very nice and helpful. I left there and it was starting to get dark, which is a good thing. I...
    julieann3 julieann3 51-55 4 Responses Dec 1, 2014

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    stamfordfan stamfordfan 41-45, M 1 Response Nov 1, 2014

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    I like to sit in hotel lobbies wearing a tight,

    short dress, black thigh highs and heels. I'd pretend I was busy reading while crossing and in tossing my legs. Sometime I'd let a passerby glimpse as I uncrossed them. I'm straight but I love the attention I get from men. Women look longer than men. They often comment on how...
    stamfordfan stamfordfan 41-45, M 3 Responses Oct 29, 2014

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    Crossdressed In A Mainstream Restaurant

    I decided one day that I wanted to go out for dinner in a mainstream restaurant while crossdressed. I persuaded a TS friend of mine to accompany me, so on the day in question, I went over to her place and changed into low key clothing so as to not attract attention and did my...
    KimBuffySummers KimBuffySummers 46-50, T 10 Responses Jan 9, 2012

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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 26-30, T 12 Responses Jan 1

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    My Best Time Out

    I've enjoyed crossdressing since I was 12.  There's always been something very special about slipping into a pair of high heels and a cute dress.My best time out was several years ago.  I knew that a crossdressers' group met at a local bar on Wednesday nights.  I really had...
    lindamariedaniels lindamariedaniels 56-60, M 9 Responses Apr 15, 2012

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    I have a fab night on Monday.

    ...The Theatre, is one of the best places that I feel total cool being Amber I wore a black bodycon dress (Midi with sleaves) a denim jacket and small black boots and black opaque stockings, in the theatre or in the bar I feel total ok, with the average theatre crowd being 70...
    amber8642 amber8642 51-55 3 Responses Sep 21, 2014

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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 26-30, T 13 Responses Jun 26, 2014

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    stamfordfan stamfordfan 41-45, M Nov 1, 2014

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    PART 1 of 2 So like before I wore womens

    underwear but became more clever about how and wear I wore it. Starting a week after my punishment was up, I slowly and secretely took some panites and spandex girdles from my mom and asked for some from my friends. The panties are bikini, thong, and boy short, and the girdles...
    ErickHernandez ErickHernandez 13-15, M 2 Responses Nov 23, 2014

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    NEW TWITTER follow @lifeasacd

    for relatible girly crossdressing tweets. no dirty stuff just girly posts us guys can relate to.
    Lovevspink Lovevspink 18-21, T Dec 26, 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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    I Like To Pose When Dressed

    Finally I got a chance to shoot a few photos for my new high heels and stocking. I'd like to share them with my EP friends. They are in the new folder "photography getting better". I will add more when I have time. Thanks for viewing and commenting.
    FannyCD FannyCD 46-50, M 15 Responses Mar 11, 2012

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    Nice Interaction!

    Last night my wife and two other couples went out to dinner together. We had to wait for a table and while we were waiting a woman that was also waiting, came over to me to tell me how very nice i was dressed and that she has noticed that whenever she is out and notices a cross...
    lindabo99 lindabo99 56-60, T 5 Responses Dec 31, 2012

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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 4 Responses Dec 2, 2011

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    Great time last night.

    Seemed to take ages getting ready and a big thanks to my sister who done my hair and make up.I met a man yesterday who i went for a coffee with and he asked me out so i thought what the hell he's nice .I wore a scalloped necked blue dress that showed just a hint of cleavage which...
    girlynicole girlynicole 36-40, F 12 Responses Aug 21, 2014

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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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    Would you like me to dress up just

    for you? Would you help me zip my skirt? Would you help roll my thigh highs up my legs?
    stamfordfan stamfordfan 41-45, M 2 Responses Oct 29, 2014

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    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 26-30, T 12 Responses Dec 25, 2014

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    On Monday I put on a pair of black jean jeggings

    and a fushia colored peasant top. Underneath I wore matching black panties and a bralette. I completed the look with a black sweater and pink running shoes. I then headed over to a friends for a morning coffee. She liked my outfit and after coffee I said I needed to go to town...
    0hBrandie 0hBrandie 41-45, M 7 Responses Apr 17, 2014

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    One Of My Last Times Out Dressed Up.

    I have written a few adventures here before and its been a while now since I have. It would be about 25 times I have gone in public dressed up since the beginning of last October. I have lost count because I have been having so much fun. This time was a few times ago out dressed...
    RobynTheBeautiful RobynTheBeautiful 41-45 13 Responses Mar 8, 2012

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    I decided today to take my flight

    while dressed as a girl. I am wearing a cute maxi dress, sandals with nice pedicured toes, pink panties, and a matching bra... Not to mention my new breast forms. I just cleared TSA and am in the bar waiting for my flight to board. This is so much fun.
    RandiHill RandiHill 51-55, M 9 Responses Sep 24, 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 21 Responses Oct 6, 2009

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