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I Would Love to Go to Work Crossdressed

Personal Stories, Advice, and Support 502 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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    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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    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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    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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    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 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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    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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    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 Mar 18

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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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    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 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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    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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    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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    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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    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 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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    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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    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...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 3 Responses Nov 29, 2014

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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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    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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    Related Experiences

    I would love to nurse, I'm in new York near mass! :)
    iluvhugetits9568 iluvhugetits9568 31-35, M Feb 28

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    I would love know why people get close to you and then ignore you? are people that shallow that they expect people to just follow them around? Do you think its abusive in a way to...
    giggles78758 giggles78758 36-40, F 3 Responses Mar 5

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    I have done research for years and secretly believe I am mated with someone. Honestly I would love to be a werewolf and not only because of the physical transformation but the...
    YoungPup101 YoungPup101 13-15, F Mar 7

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    Would Love To Be Strapped Down and have teeth pulled
    goodnites25 goodnites25 22-25, M 1 Response 6 days ago

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    Would love To Be Strapped Down And Tickled
    MaxtheSuperhero MaxtheSuperhero 13-15, M 1 Response 6 days ago

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    I Would Love To Be Strapped Down and sedated
    goodnites25 goodnites25 22-25, M 6 days ago

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    Would Love To Be Strapped Down And Tickled
    goodnites25 goodnites25 22-25, M 6 days ago

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    Would Love a Delicious Slice of Pizza
    goodnites25 goodnites25 22-25, M 1 Response 3 days ago

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    So like there was a period of my life where I was like in good shape... Looked good and felt good about my body. The catch is I was in shape because I had seen a pic of myself and...
    Sezom Sezom 36-40, M Mar 9

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    It's the best way to get the day started. It motivates you to do more throughout the day and you can end your day early and still feel accomplished. I would be pudding in any woman...
    TrailrunnerMN TrailrunnerMN 31-35, M 1 Response 6 days ago

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    I love exercise. It allows me to push my body to the limit, and there is nothing better than seeing the transformation your body can make. Consistently taking your workout to the...
    amberBNYC amberBNYC 31-35, F 1 Response Mar 1

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    I'm a Trans woman.. but I'm super far from passing... I'm ur "macho looking male"... it kills me not being able to have big breasts and being myself.... I want to grow them... but...
    readypink13 readypink13 26-30, T 1 Response Mar 16

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    Worked out for five hours today. Don't even have the energy to shower. I need a foot massage
    lindatheworkoutmom lindatheworkoutmom 51-55, F 4 Responses 6 days ago

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    I really love being a preschool teacher. I run a half day preschool program and it's so full filling. The only draw back is no adult interaction! I miss working with adults. Lol.
    recycledknowledge recycledknowledge 41-45, F Mar 5

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    Time to workout again. 85 squats down 50 more to go.
    mstv1112 mstv1112 16-17, F Feb 28

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    Intense workout time.. Florida beach in a couple of days.
    mstv1112 mstv1112 16-17, F 1 Response Mar 5

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    I work pout 6 days a week and Monday's are always the the tuffest to have motivation!
    ayelex20 ayelex20 22-25, M 1 Response Mar 9

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    The after workout smoothie, nothing tastes better.
    JohnSpartan JohnSpartan 41-45, M Mar 12

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    Boys, im just trying to work out, build a healthy body, keeping in shape. So please, STOP bothering me while im running on the treadmill and you'll be like, Guy : " Whoa, chill...
    annaambrose annaambrose 16-17 6 days ago

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    Is there anyone here who would like to meet up? :)
    AntonyLovesLongHairAndSilk AntonyLovesLongHairAndSilk 18-21, M Feb 28

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    I think that before there can be world peace there must be more respect for our fellow man. In traffic today I was driving down the street and I saw this guy cut two guys off. This...
    CalabrianCarlos CalabrianCarlos 41-45, M Mar 12

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    Lately I often sleep after school, then learn and go back to sleep. It would be awesome just to have someone who lies down beside me, cuddle with me and be by my side. It feels...
    CeMi1706 CeMi1706 18-21, F 3 Responses a week ago

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