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I Would Love to Go to Work Crossdressed

Personal Stories, Advice, and Support 467 People

    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'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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    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 14 Responses Feb 16, 2010

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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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    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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    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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    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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    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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    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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    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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    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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    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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    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'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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    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 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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    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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    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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    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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    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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    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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    Related Experiences

    I been single for almost a year now .. I been getting those urges you know .:/ Feeling really lonely at times but , I'm able to last a year .. Don't get me wrong I'm able to get a...
    veenuss veenuss 18-21, F 20 hrs ago

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    Work out time!!! I love working out
    carmencyr43 carmencyr43 13-15, F 3 Responses Jul 29

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    I love working out i cant go a day with out it. Its in my dna
    sneer95 sneer95 18-21, M Aug 8

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    You can additionally desires within the game by keywords to look for your organization. Players club is account binding, within the club can solely show your userid and your each...
    mmogoogle mmogoogle 22-25, M Aug 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 Jul 24

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    I would love to be in a relationship where we exercise together like go running outside or lift weights at the gym. I've always thought that'd be a definite bonus in a relationship...
    BeautifulCatastr0phe BeautifulCatastr0phe 16-17, F 2 Responses Jul 29

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    I would love to go into the abyss.
    kamachulu kamachulu 22-25, M Jul 29

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    being 1/32 Irish (small I know but traced through the mothers, mothers, mothers, mothers line - it's got to count for something) I would love to find my Irish roots! ;-) Lucky...
    queerinthehead queerinthehead 41-45, M 6 days ago

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    being 1/32 French born British Subject (as per 1851 census) I would love to find out where in France the birth took place, the mystery of this ancestor and her connections to the...
    queerinthehead queerinthehead 41-45, M 6 days ago

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    I would love to live by the ocean that's one of my dreams😊
    phillips0430 phillips0430 13-15, F 3 Responses 2 days ago

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    I think being a model would be so cool
    PrototypeBri PrototypeBri 18-21, F 1 Response 9 hrs ago

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    I work with 2 year olds and I love it! They can be a challenge but I love teaching them and seeing them grow and learn.
    ButterflyGirl83 ButterflyGirl83 31-35, F Aug 3

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    Even on my rest days, Im thinking about training or Im writing out a workout to do at some point. Working out is my drug, and damn it feels.
    animal47 animal47 22-25, M Aug 5

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    I'm 32 from Ontario 6ft 200lbs brown hair and eyes looking for an anr. I work hard and am a pretty decent person. Send me a,msg :)
    mike1100 mike1100 31-35, M 1 Response Aug 11

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    It makes me feel happy. Every time after a good workout, I am hyper active, happy, cheerful, full of life.... I dont workout a couple of days, my life is ordinary like others.
    meaningful2216 meaningful2216 26-30, F 1 Response Aug 13

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    I'm very sick. High fever, congestion, runny nose, cough, allergies, and period cramps yet I'm still working out! That's what I call motivation but then again that's what I get for...
    XxbixtchybellaxX XxbixtchybellaxX 13-15, F 1 Response 5 days ago

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    I work at a veterinary hospital. I'm 16, but I still see a ton of cool stuff. I love it!
    hdial043 hdial043 16-17, F Aug 1

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    Working out right now!!!!!!
    thatonegirl156 thatonegirl156 16-17, F Aug 2

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    I'm ready to kill my work out right now! :D Sore morning here I come! ;)
    mcatH2O mcatH2O 22-25, F 1 Response Aug 3

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    Making the most of your time with a nice intense workout is a great way to stay in shape.
    Workoutguy720 Workoutguy720 26-30, M 1 Response Aug 5

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    Mainly elementary-aged children. I admire their innocence of the world around them. I used to work at my aunt's daycare during the summer and there was this little girl who...
    EllaAfter EllaAfter 22-25, F 3 Responses 5 days ago

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    Buy he tells me he doesn't know why. I love him so much, and I know he loves me, but there must be some reason for his affair, he even cries, and tells me he doesn't know why he...
    Mylifesover Mylifesover 46-50 5 Responses Aug 8

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    I would do anything to be in Hawaii....I'm dying to get away and just forget about all my trouble in life. Even if it's just for a few days.
    VivirLaVida VivirLaVida 16-17, F Aug 6

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    Well i dont need to say would because i am a dj and its amazing playing for 13 hours straight mixing tracks up and everyone enjoying them selfs :)
    callumjames18 callumjames18 18-21, M 1 Response Aug 9

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    I'm afraid, but also excited by the idea my mistress would feminized me.
    Epic99 Epic99 46-50, M Aug 11

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    I love being humiliated, degraded, abused, forced, commanded. Please feel free to message me filthy things ;P
    kinkykittyxoxo kinkykittyxoxo 22-25, F 2 Responses Aug 11

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    Yes I like to have inteeligent conversation with people.But I would like to know more about you to be more comfortable with you? Is that wrong on my part?I like to be totally...
    restored87 restored87 46-50, F 3 Responses a week ago

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