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I Would Love to Go to Work Crossdressed

Personal Stories, Advice, and Support 532 People

    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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    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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    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 13 Responses Feb 16, 2010

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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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    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 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 2 Responses Oct 8, 2013

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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 1 Response Sep 14, 2011

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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 6 Responses Apr 24, 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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    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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    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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    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.
    DanielleW51CD DanielleW51CD 51-55, T 2 Responses May 28, 2014

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    It is a long time ago now,

    but I did go into work at the weekend and got changed in my room into black tights, heels and a black dress. I sat and did my work for an hour or so, then I needed to go to the toilet. So I ventured out into the corridor and walked along to the loo. I decided to go into the...
    deleted deleted 26-30 3 Responses Nov 29, 2014

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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 9 Responses Dec 26, 2010

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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 3 Responses Feb 11, 2009

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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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    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 1 Response Dec 3, 2013

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    I would love to go to work in a tight skirt

    and heels, maybe working in a shoe store and taken to the stock room and be seduced.
    carsheelsandwomen carsheelsandwomen 36-40 1 Response Mar 18

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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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    Related Experiences

    I have been there once and would love to go back. I had a wonderful time and would love to see other places as well ( such as Scotland or Ireland).
    asert12345678 asert12345678 31-35, M 28 mins ago

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    I'm looking for a daughter that wants to make a baby together. Might that be you?
    BlueSkiesNoVa BlueSkiesNoVa 51-55, M 2 hrs ago

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    I just want to go because I'm phan trash.
    killjoy122 killjoy122 13-15, F 2 hrs ago

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    I would like to meet people who are from the UK
    bloodycrimson8 bloodycrimson8 16-17, F 18 hrs ago

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    Getting a workout in is the best part of my day, after hanging with my family... I love the feeling of knowing I'm doing my body good. I look around at overweight people and...
    MsInvis MsInvis 46-50, F 3 Responses 1 day ago

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    Some day..Id love to wake up and one of the first things i see (other than the person im in love with)be me looking out the window and see the ocean :) I'd love to be able to walk...
    simpleandpossible simpleandpossible 22-25, F 1 day ago

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    This is Megs. I'm excited to be her roommate again when I go back to school for sophomore year in a few weeks. Now, she lovessss sex. Sometimes, we even had it work out where if...
    haleystar haleystar 18-21, F 11 Responses 1 day ago

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    I have a dream of living in a house or an apartment with other people, who would actually care about each other. Everyone would have their private space, but whenever you come to...
    thundrstorms thundrstorms 18-21, F 1 Response 1 day ago

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    ..just love opening txts or email from someone who is flirting with me.
    Ourorborus Ourorborus 36-40, M 2 days ago

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    Didn't do the greatest work out in the world but still worked it out
    Notyourprincesa1124 Notyourprincesa1124 31-35, F 2 days ago

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    My fur would be blue. Also cosplaying is great too.
    KindredKings KindredKings 13-15, M 1 Response 3 days ago

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    Any thoughts on this? Love my woman and do not want to change my life. I do want to try it sometime,she will never go for it she says.It has been a fantasy of mine for a long time...
    qrqqqqq qrqqqqq 51-55 1 Response 4 days ago

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    pizza is the love of my life although that ***** called fat is trying to stop me seeing pizza very often :'(
    s3xyPsyc0 s3xyPsyc0 18-21, M 1 Response 5 days ago

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    Or maybe the whole box. Pizza is love !
    Gill1998 Gill1998 16-17, F 1 Response 6 days ago

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    I'd love a hot slice of pizza with lots of cheese, pepperoni, sausage, green peppers, mushrooms, and garlic crust.
    imveryboring imveryboring 13-15, F 2 Responses 6 days ago

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    I feel like just opening up and talking. Is there anything you would ask me? Could be serious, could be completely irrelevant.
    DaffodilDeary95 DaffodilDeary95 18-21, F 1 Response 6 days ago

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    So I was at my friends house just hanging out. So my parents call me and said that it was time to come home. So when I got home my parents where waiting for me. So I asked them why...
    Altickler Altickler 13-15, M a week ago

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    I’m trying to decide if I want to change my gender from male to female. I’ve been trying to find a woman who will love me as I am for a very long time. I’ve dated three women...
    JohnL2015 JohnL2015 36-40, M a week ago

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    Nothing ever is better than Blake, Adam and Anders. Get weird and stay fresh
    Indicudsarah Indicudsarah 18-21, F Jul 22

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    Especially the feeling you get when it causes you to lose your breath and frantically gasp for air while your heart feels like it's beating out of your chest while beads of sweat...
    UnderDarkClouds UnderDarkClouds 18-21, M Jul 21

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    Not exactly there yet but in beginning to really enjoy it. Trying my best to be consistent and get a good routine going. When I leave the gym I feel like a winner. Like nobody can...
    hiddenjem hiddenjem 22-25, F 2 Responses Jul 20

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    It was leg day, Tabata style. Over 300 reps focused on glutes, quads, hamstrings and calves! Men can work on their booty too! #thongbackside
    deleted deleted 26-30 2 Responses Jul 20