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I Would Love to Go to Work Crossdressed

Personal Stories, Advice, and Support 544 People

    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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    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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    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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    I told one of people on the Equality

    and Diversity committee at work that I wanted to come in wearing dresses and skirts. This was part of the reply. "I fully support your decision to come in what makes you feel most comfortable. I applaud your decision to be true to yourself and would anticipate that others will...
    jeffreyrichards2015 jeffreyrichards2015 56-60, T 3 Responses Aug 17

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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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    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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    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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    this is getting real now.

    I have told two of my co-workers that I want to come in to work wearing a skirt or dress. I am very nearly at the point where I going to talk to my boss about it. I really really want to do this. its driving me mad.
    jeffreyrichards2015 jeffreyrichards2015 56-60, T 1 Response Aug 15

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    I am telling more people at work

    that when I return from holiday I will be wearing skirts. I thought I would share with you the latest response from one of the girls in the restaurant. "It's great that you feel you can be yourself, it's a shame I'm not smaller, you could have borrowed my skirts ha ha! I really...
    jeffreyrichards2015 jeffreyrichards2015 56-60, T 4 Responses 4 days ago

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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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    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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    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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    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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    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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    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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    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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    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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    Big step forward!! I got this message from the

    HR department at work after telling them that I want to come to work wearing skirts and dresses. "You are fully protected by the legislation and (company name) would 'fully support' you." Furthermore "the Equality Statement and the Bullying and Harassment Policy would be...
    jeffreyrichards2015 jeffreyrichards2015 56-60, T 3 Responses Aug 21

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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 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 1 Response Oct 24, 2012

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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 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, T 2 Responses Oct 8, 2013

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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 8 Responses Dec 26, 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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    Another step forward today!

    I spoke to my boss, my immediate line manager, told him I want to come to work in a skirt, this is the bit I was dreading. His reply: "That is absolutely fine with me, I have no issues" I am on holiday at the moment, but in a couple of weeks I will return to work and complete my...
    jeffreyrichards2015 jeffreyrichards2015 56-60, T 2 Responses Aug 24

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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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    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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    Related Experiences

    hey if any girl would like to talk about haircutting /hairshaving or just hair in general pm me ,Lets talk:P
    Liveyourway1 Liveyourway1 16-17, M 11 hrs ago

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    Hooters has so many different colored waitress uniforms. I think they all look so lovely :) The tight shorts and top with large breasts spilling out of their bras makes the...
    satnlacy satnlacy 22-25, T 7 Responses 16 hrs ago

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    I have been thinking of something to write about, topic for today. I really don’t have one. So, I am going to make one. I am going to write about three things that crossed my...
    bujji14 bujji14 22-25, F 21 hrs ago

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    I'd love to join a gum where clothing was optional. It would be awesome to be seen naked by every one while lifting weights!
    deleted deleted 26-30 1 Response 22 hrs ago

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    Another weekend passed by, so fast. Everyone shares this sentiment, weekends pass by quick. Starting Monday we wait and wait for the elusive weekend, the short spell of peace on...
    bujji14 bujji14 22-25, F 1 day ago

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    Please tell us why you would love to shave your head and what is stopping/preventing you from having it shaven?
    snpclpshv2 snpclpshv2 51-55, M 2 days ago

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    I almost didn’t write anything today. I got lazy, then I realised, that that’s what has been holding me back. Stunting my movements and growth, since past few years. So I...
    bujji14 bujji14 22-25, F 2 days ago

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    I really would.... Extremely nervous about it though. I don't like my hair on my ears, neck or in my eyes. This would be one way to remedy that situation..... Now, just finding the...
    KwenB KwenB 41-45, F 8 Responses 2 days ago

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    I want a workout partner or buddy
    kristinellis18 kristinellis18 18-21, F 1 Response 3 days ago

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    Morning working done! Ready to enjoy the rest of my Saturday. Thanks to Avenged sevenfold for providing me with good workout tunes
    Salsaconqueso1124 Salsaconqueso1124 31-35, F 3 days ago

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    if you're a female with a big belly I would enjoy covering it with body lotions and fragrant oils and rub it over and over hours upon end..I love enjoying a bigger woman so much...
    thebustierthebetter thebustierthebetter 46-50, M 3 days ago

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    I am going to write about a tale from history. I have been thinking about it from a while now. I love history, fables, tales. specially if you are in country whose past was...
    bujji14 bujji14 22-25, F 1 Response 4 days ago

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    Bring it on big girl....push me down and make me tap out as I do it smiling ....do be smothered by your big massive chest would always have me losing to you why we playfully...
    thebustierthebetter thebustierthebetter 46-50, M 5 days ago

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    So I have decided to start writing something, anything, everyday. Maybe one day I might pen down a story. I have realized when I write about my feelings or share some anecdote, I...
    bujji14 bujji14 22-25, F 5 days ago

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    i was a difficult kid and my mother says she used to had the toughest time to putting me to sleep. slightest shift of her body would make me got up and all in panic.....i still...
    snuffal snuffal 26-30, F 3 Responses 5 days ago

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    I think you are super sexy and would love to have you control and dominate me anyway you want
    michelleplus1 michelleplus1 56-60, M 6 days ago

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