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I Would Love to Go to Work Crossdressed

Personal Stories, Advice, and Support 469 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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    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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    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'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 6 Responses Mar 21

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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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    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 12 Responses Feb 16, 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 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 6 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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    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 recently came out to a former fashion srylisr

    I know. She loves it we have similar tastes and like she's a hoarder. When she saw my entire wardrobe she said 'babe' I know you make light of wanting to try a day job as Nicole; but honey....you have a stunning wardrobe of what. ..30 smart tailored dresses...I mean you could...
    NicoleTS NicoleTS 41-45, T 5 Responses Nov 2

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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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    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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    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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    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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    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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    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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    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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    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 2 Responses May 28

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    Related Experiences

    I would love to go slow dancing with my wife, but she don't like to dance. And I LOVE to dance. I don't become pushy, I just turn in a slow song every now and then and ask her when...
    Sheismybestfriend Sheismybestfriend 31-35, M 1 Response 3 days ago

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    I have been working out for a whole month and I'm already getting results. My stomach is more toned and my *** is lifted more because of squats. I don't go to the gym so I do...
    teresastarr teresastarr 18-21, F 7 Responses Nov 5

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    Went back to work after a couple of days off and it felt great! I love working! Work is inspiring and fun and challenging! Much better than sitting in my *** feeling sick and doing...
    Hard2Beat Hard2Beat 36-40, M 1 Response 1 day ago

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    I'm always messaging women, and some reply, but most don't. I see a lot of women who have the same experiences as me (mature ones) but I think they aren't telling the truth. I...
    dcisme dcisme 41-45, M Oct 30

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    I would love to slow dance with a man but I would love to go dancing with a guy dancing to country music fast and slow and also dancing to oldies rock and roll /swing dance music...
    Mtay222 Mtay222 22-25, F 3 days ago

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    I'm a uk nappy lover and love wearing outside. I don't have any camping equiptment but would love to go camping with boys into nappies and sissy things .I'm from West Sussex...
    SEANYBABYNAPPY SEANYBABYNAPPY 51-55 2 Responses Oct 22

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    i would love the idea of being dressed up as a girl in nice frilly dresses and be in a womanless beauty pageant
    GirlyAndrea1987 GirlyAndrea1987 26-30, M 1 Response Oct 28

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    I would love to.. Message me :)
    dashuria dashuria 13-15, F Nov 2

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    I would love to be friends with benefits with someone, girls mainly but I might be open to being one with a guy. I don't really know, I'm bicurious but don't know if I could do it
    biventure biventure 22-25, M 1 Response a week ago

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    I'll tell you, there are few things I love more on this earth than working from home. I kind of fell into the work-at-home model while in another career field, but now that I'm...
    amorousvoyager amorousvoyager 46-50, M 1 Response Nov 2

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    I just joined the gym this month. i went an entire 2 weeks with my cousin as he was showing me around and spotting and helping me.. he stopped going due to health issues and that...
    doubtful09 doubtful09 18-21, F 3 Responses 23 hrs ago

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    I would too but my interests are being on my own and having no friends, how's that gonna work :-0
    vince808 vince808 41-45, M 2 Responses Nov 2

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    BokwaI have worked out at the gym for years....up to 6 plus hours per week. Unfortunately, the last 3 gyms I have belonged to have closed within the past 2 years. My current gym...
    akindheart akindheart 56-60, F 5 Responses Nov 5

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    Been there 4 times this week , am almost 50 years. body is in good shape and firm and hard am stronger than most women. Training very hard very intensive and much is not like...
    whitebow whitebow 46-50, F 1 Response Nov 6

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    Technology has replaced so many people and put us all in offices; I just don't feel at home in an office I need to be moving and physically working. I work on bicycles; there is...
    TryingToLoveLifeNow TryingToLoveLifeNow 18-21, F 1 Response 2 days ago

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    I love the feeling when I've given everything at the gym, and the body aches in a good way. Working out is an addiction I can definitely live with! ;)
    Sardintroll Sardintroll 18-21, F 1 Response Nov 8

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    Does anyone here do this? How does it work? Where do you park overnight?
    squirrelbounce squirrelbounce 41-45, F 1 Response Nov 9

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    On good days I work out.. On bad days I work HARDERRRRR! It's a bad day! Not a bad life :)
    Anngeleyes Anngeleyes 26-30, F 1 Response 1 day ago

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    Im having a day off today I feel crap and im so tired but I feel guilty as ive got loads to do at work and its my business
    wheels1972 wheels1972 41-45, M 3 Responses 1 day ago

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    Tense beach pump sand run workout can esthetics 👍👌👊😜
    CHEEKY7615 CHEEKY7615 36-40, M 6 days ago

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    I worked out for an hour today at the gym. Feels great
    armstrong7984 armstrong7984 26-30, F 1 Response 5 days ago

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    It's my favorite thing to do. I don't think my day is complete without me lifting weights or just running at the gym, especially after this new workout I've been doing for bout a...
    SoBeCurious SoBeCurious 18-21, M 1 day ago

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    I know I gotta love myself before a man loves me but its hard to love myself. I even shudder at the thought of it. I realise that I would never be loved cuz i don't love myself...
    Myalee Myalee 41-45, F 1 Response Oct 22

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    Once again on the gym this time doing 90 mins cardio. will be going nearly everyday during the run up to Christmas with cardio one day then weights the next. its a great buzz and...
    Thonglover6969 Thonglover6969 41-45, M 4 days ago

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