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I Would Love to Go to Work Crossdressed

Personal Stories, Advice, and Support 464 People

    Work As Yourself Is A Fulfilment

    In every other aspect of work, employment of otherwise, we regard the most meaningful and fulfilling aspects as being those that express ourselves. Whether caring roles, or analytical thinking, strong, skilful or whatever makes the work most suited to ourselves and making the...
    Fullcircle Fullcircle 51-55, F 2 Responses Mar 27, 2011

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    I'm working on it. Planning on 3 informal

    interviews for internships - unpaid. I am just going to turn up perfect;ly femme and see what happens, For me - this is the 'final hurdle'' and can do anything after this!
    NicoleTS NicoleTS 41-45, T 3 Responses Mar 21

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    Working Crossdressed

    I work for my father and after I came out a few years ago he told me that I could not come to work crossdressed under any circumstances which I accepted at the time. His attitude has softened over the past few months however as I am getting closer to becoming the woman I have...
    Jennianne Jennianne 41-45, T 14 Responses Feb 16, 2010

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    Well, I did manage this due to a Red Cross

    charity event, held once per year and entitled "Crossdress for Red Cross". One middle aged woman knew of my predilection. I had trusted her for years and we confided with each other on a range of issues, trusting each other implicitly. We saw this ad for the upcoming...
    Hdumpty Hdumpty 46-50, M Feb 18

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    Another Day In Paradise

    Went to work again today wearing a bra under my blazer, complete with falsies. Modest 38B cup, seam free under a dark shirt. Blazer was chequered so it masked the adjusters in the back. Even had an hours feedback from my boss sat two feet way. Someone even put their hand on my...
    Deuteronomy58 Deuteronomy58 46-50 Sep 21, 2012

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    I Have Been Fully Crossdressed At Work! Part II

    I used to work for a company where I had the chance to crossdress on occasion. You can read about this in an earlier story in this group. I would fully crossdress other than make up in case someone would show up and I had to do a quick change and this is why I have my face...
    jamie50 jamie50 51-55 1 Response Jan 12, 2013

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    Going One Step Further!

    I have always had a fantasy of becoming a Manager of one of the large scale shoe stores like Shoe Carnival, Payless etc. I make a great living in what I do today, but the fringe benefits of being a manager of one of these stores would be great. Locking the doors after closing...
    jamie50 jamie50 51-55 2 Responses Dec 3, 2013

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    Crossdressed At Work

    Before I was laid off and working I would Cross dressed on the weekends. As there were so many things going on at the same time I'd go into work to do a little catch up. I love to wear dresses so I went into the office in women's clothes, shoes, watch and jewelry. There were a...
    jml2000 jml2000 56-60, M 3 Responses Mar 20, 2013

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    Working Girl

    I think every one of us had had this thought at one time or another, whether as a fantasy or actually doing it. I know I would love to go to work as a woman. That would really help to complete me being in the womans role. When I was self-employeed, I could go to work...
    fayeanneleigh fayeanneleigh 51-55, T Nov 30, 2009

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    Oh, To Be One Of The "Girls At Work!"

    I want to turn up at the office one morning clad in a smart, stylishly-cut suit of navy jacket and skirt. The skirt is a tight pencil, shrink-wrapped to my hips, thighs and bottom. It restricts my thighs and gives me a sexy hobbling gait, as do my black patent high heels that...
    Silkendreams Silkendreams 46-50, M 7 Responses Apr 24, 2013

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    At Work and At Play

    Yes, I surely would! At work: At play:   Special times:   I would absolutely love it!!!!! Ahhh, the freedom!
    Josie06 Josie06 56-60, F 2 Responses Jul 27, 2009

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    Wearing Pantyhose to Work

    I have gone to work in Panties also.  I use to call it Panties Friday, no possibility of panty lines with typical male jeans.  Pantyhose are another item all together, it's no real problem to wear them to work if you wear regular socks.  The only thing which I was...
    rickinskirt rickinskirt 41-45, M 4 Responses Feb 11, 2009

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    I Would Love To Go To Work Crossdressed

    I would so love to do this! I think I would have to find a job in a sex shop to do this though. Dressed in a tight blouse and short skirt, I would mince around in high heels straightening the shelves and serving customers. I would be fully made up and perfumed. Long nails would...
    phantomime phantomime 46-50 1 Response Oct 8, 2013

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    I Like To Go To Work Crazy Dressed But Need To Be Careful

    I am a big man and I never try to pass as woman, and never would, but I have a passion for tight and body hugging sports clothing and one-piece clothing from swimsuits to snowsuits, be it labeled mens, unisex, or most often, female. It started from curiosity when I was about 13...
    tightsvirus tightsvirus 41-45, M Oct 24, 2012

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    More Pictures Of Being Crossdressed At Work

    I loved to crossdress at work on the weekends when no one was there. Here is a couple more pic's. This particular day I decided to really work comfortable in my White Babydoll, pantyhose and gold T-strap Jolene Mary Janes.
    jamie50 jamie50 51-55 2 Responses Mar 30, 2013

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    Yes Indeed

    Yes I would and would not hesitate. From the panties and bra out to a dress and high heels. Some jewelry and a dab of perfume. Only I guess for me it's not crossdressing as this is how I see myself all the time. As a woman. Call it crossdressing, call it natural ... I just want...
    Josie06 Josie06 56-60, F 7 Responses Jul 24, 2008

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    Walking To Work

    i only live 10 minutes walk from work and i walk with a friend every day and just looking at her wearing a skirt i always keep saying to my self i wish i could wear a skirt to work .
    georgiacd georgiacd 41-45 6 Responses Sep 10, 2011

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    New Wig

    I was determined to buy a wig today. Difficult for a crossdresser. I went shopping in male mode and walked past two shops I targeted plucking up courage to go in. One had a hairdressers attached to it with a couple of women serving. The other just a wig shop but with a man behind...
    Deuteronomy58 Deuteronomy58 46-50 Jul 17, 2013

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    I've been to work dressed on Halloween twice

    before in an office environment. Now I work on the weekends at my friends lingerie store. On Halloween I wear a costume like French maid, nurse and even a bride.
    Daniellew51 Daniellew51 51-55, T 3 Responses May 28

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    Easy To Do If You Work From Home

    Thanks to an understanding wife and a job where I can telecommute, I go to work in my favorite dress every day!  When I do have to go to the office I at least wear a comfortable slip and pantyhose under my "man suit" :-)
    CDralph2010 CDralph2010 46-50, M 2 Responses Sep 14, 2011

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    I Have Been Fully Crossdressed At Work!

    The company I worked for 3 years ago, carried highly classified materials and was somewhat like a fortress. Very few people had access to this building during non working hours and once inside you could deadbolt the main access and no one could enter. If somebody should want in...
    jamie50 jamie50 51-55 5 Responses Dec 26, 2010

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    One Can Only Hope

    I would love to go to work crossdressed. Women do it all the time. If I went to work in a skirt I would get fired. But I can hope that one day that will change.
    Adam59 Adam59 56-60, M 1 Response Mar 30, 2013

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    Jenni My Pa

    I know that women often complain about having fewer job opportunities, etc especially now with the recession. My solution was to start my own business with a women only policy. I now have three women and another T-girl working for me. The T-girl actually came to her first...
    sammi11 sammi11 41-45, T 6 Responses Dec 10, 2010

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    Related Experiences

    I love working out, it has transformed me from a depressed scrony, not confident boy, to a totally new person who loves working out and values life now. I enjoy waking up in the...
    VishalM92 VishalM92 18-21, M Jul 1

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    It is my favorite thing to do. It gets me through cravings of all sorts, it improves my body, and it clears my mind. I love to run, but not crazy distances. I love to lift, but not...
    DakotaBelle DakotaBelle 31-35, F 6 Responses Jul 16

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    Oh how I would love this so much. I have the perfect guy who could make it romantic. As well as I've told him that I would love to be kissed in the rain...so we shall see....
    jlhhlj123 jlhhlj123 22-25, F Jun 30

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    I would love to meet a female or maybe even a male (UK) who dress me up & teach me how to be more feminine. I love lingerie & have a wide range, but need help on the next step to...
    susspender susspender 41-45, M 1 Response Jul 12

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    Anyone who would like to talk to me to help me come out of my shell about tickling i would love too talk too you :) Females preferably please :)
    DeanGrimes DeanGrimes 18-21, M 2 days ago

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    I am in York. I would love a massage by a sensual man who truly knows how to massage, I'm willing to pay a tenner lol ; )
    cheekyhen cheekyhen 36-40, F 4 Responses Jul 6

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    I would love to write a story about my whole life so far. Young nd scar-ed. Young nd reckless
    ashley486 ashley486 13-15, F Jul 11

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    I would love an email penpal someone to just talk to about life and vent and have someone to relate to. If there are any takers just message me!
    PrincessAbigail89 PrincessAbigail89 22-25, F 1 Response 4 days ago

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    I've started working out now that I am less busy with uni work and I got to say, I actually enjoy it. Loads of people hate the thought of exercising and going to the gym but I had...
    BeautyOfSuffering BeautyOfSuffering 22-25, F Jul 12

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    im pretty fit and I love it just wish I had a workout buddy. Im starting weight training for my arms shoulders and back. I love women at the gym better than at the club.
    Jamila94 Jamila94 18-21, F 1 Response Jun 29

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    I'm tired of looking chubby so I've been working out. It feels so great to work out and know I'm gonna look good in the future
    Jteen15 Jteen15 18-21, M 1 Response Jun 29

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    This is not an experince just couldn't fit all of it in a question sooo I'm playing football for a private school this year starting highschool and I was going to tryout for...
    eliaszavaleta eliaszavaleta 13-15, M 1 Response Jul 16

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    I am soo sore for working out yesterday! I need to be down 15 pounds before my birthday next month! I stopped eating meat & I work out everyday! Not to mention I drink laxative...
    Sweetie899 Sweetie899 22-25, F 3 Responses Jul 16

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    Thats actually one of my dreams so long that i cant remember since when. In a wood house, two floors with a big porch on front. I have always wanted to adopt many children etc. Now...
    LeahNl LeahNl 31-35, F 1 Response Jul 18

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    I love the feeling I get from working out...I crave the gym and cardio...it is the best antidepressant on the planet...I'm about to kick it up a notch...I want this body in beast...
    brightbabyblues4u brightbabyblues4u 36-40, F 4 Responses Jun 29

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    I play football so of course I have to workout ha
    dre07 dre07 18-21, M 1 Response Jul 3

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    Working out is awesome so is football I'm trying out for te this year te stands for tightend if u didn't no I've been accept to play football for a private school it's so amazing...
    eliaszavaleta eliaszavaleta 13-15, M Jul 13

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    It was Hot So I Got Naked & started Working On My Brakes Out Back Of My House What a Man To Do Living In A Three Bedroom House All By Myself LoL
    NakedHiker51 NakedHiker51 51-55, M Jul 15

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    I do know that it sucks but the work pays off in the end with more confidence
    xJamix xJamix 18-21, F Jul 18

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    A lot of people hate exercising because its tiring and it hurts and all that. But I love it! I go for a run everyday with my dog. I do a lot of different exercises but usually push...
    HappensForAReason HappensForAReason 13-15, M Jul 1

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    I would actually love to have someone I can be me around on a daily basis and just having that click. Being able to go shopping (Which even for a guy, I love doing) and just...
    Zestyginge Zestyginge 18-21, M 1 Response Jul 3

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    Advice anyone?—So I am a 17 year old male in high school (I'm basically the biggest loser ever, so most everybody hates/dislikes me anyways), and I will be going into the Air...
    Phoenix259 Phoenix259 16-17, M Jul 6

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    Maybe this would be good to try with my husband since he cannot have sex with me till late September but maybe it would lead to it which would be bad lol
    wheelsxoxo wheelsxoxo 22-25, F 2 Responses Jul 2

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    I was on a train he other day looking out at the fields pass by. I wished that I could be dropped, completely naked, into one of them and have to make it back home. I started...
    Bartimaues Bartimaues 31-35, M Jul 16

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    I want to have a relationship with a girl where she is naked all the time .this would be fun
    ballboy24 ballboy24 18-21, M 1 Response Jul 1

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    Hey, im new to this site and would luv to answer any question, or if you want to just talk, im just a teenager myself so would luv to talk to someone x
    jademariexx jademariexx 13-15, F 2 Responses Jul 4

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    well yes I would like to get to know somebody from the State of Adelaide, South Australia someone who I can get along with and understands my situation