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I Would Love to Go to Work Crossdressed

Personal Stories, Advice, and Support 484 People

    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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    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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    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 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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    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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    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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    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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    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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    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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    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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    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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    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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    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 7 Responses Dec 26, 2010

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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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    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 4 Responses Nov 2

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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

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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'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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    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 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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    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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    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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    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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    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

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    Related Experiences

    Hi mel here would love some tributes from anyone. Please see comment below.
    couplemelkevin couplemelkevin 41-45 3 Responses 19 hrs ago

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    I like female legs and feet so much! I like girls in beautiful footwear but most of all, I like barefoot girls. In summer, when I go to seaside towns and see girls going barefoot...
    NocturnalCreature NocturnalCreature 26-30, M 1 Response 10 hrs ago

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    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 Nov 18

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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 Nov 19

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    We would love to know if there is any our stories you would like to hear as a confession. As we can put more longer detailed xra..d version in there. Please comment below, to let...
    couplemelkevin couplemelkevin 41-45 3 Responses a week ago

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    I have someone special in my life that I would love to spend the day with in bed. She is sweet, kind, beautiful, and loves to cuddle. She's in bed right now, and I wish I were...
    LifeinWoodinville LifeinWoodinville 41-45, M 2 Responses Nov 22

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    I would love to sleep In bed with a sexy lingerie without no underwear Sleeping with someone special.
    lorrena19 lorrena19 18-21, F 1 Response Nov 23

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    I would love to have a family of my own some day.
    kellywedgieknickers kellywedgieknickers 18-21, F Nov 28

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    I would love to get a massage from someone right now. Just laying on the bed totally letting go to whoever is giving me a massage.
    deleted deleted 26-30 Nov 28

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    one day i would love to be put through corset training. have a woman put a black steelboned corset on me and give me a feminine shaped body. like this: 
    GirlyAndrea1987 GirlyAndrea1987 26-30, M 5 Responses Nov 29

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    I would love to live on a island
    Bpack Bpack 31-35 Dec 1

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    Hi all you naughty men/couples mel would love some naughty stories sent to her by message through here only. Please see comment below
    couplemelkevin couplemelkevin 41-45 2 Responses 6 days ago

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    I'm afraid I've never had a proper hug all night in bed...I would love to have that just once. Or for a week.
    Sinjintiger Sinjintiger 41-45, M 1 Response 4 days ago

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    i would love to have girls give me a complete girly makeover. let them put makeup on me such as lipstick, lip gloss, lip liner, eyeliner, eye shadow, foundation, mascara and blush...
    GirlyAndrea1987 GirlyAndrea1987 26-30, M 2 Responses 2 days ago

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    i would love to spend the day in bed with my wife but unfortunately she does not feel the same
    needtobloved needtobloved 41-45, M 2 Responses 2 days ago

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    I love going to the gym and lifting weights. it is my church, my form of therapy. it truly is one of the few places that I can take refuge from my own mind. feeling the burn, the...
    exiled11 exiled11 31-35, M 4 Responses Nov 22

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    Anyone who is looking to supplement their income or live a more natural healthier life. Would you like to make some extra money not only for the holidays coming up but maybe to...
    CassieBennett CassieBennett 26-30, F 1 Response Dec 9

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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 Nov 20

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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 Nov 18

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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 Nov 19

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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 Nov 20

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    So I may not be the fittest person in the world but I plan on becoming a fit person. It sucks when you're a heavy person with a fit person mind set. I want to run for miles and...
    laneicemusic laneicemusic 18-21, F 3 Responses Nov 28

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    Okay. I love to work out. It's a part of my day. Recently I haven't been able to find the motivation to get to the gym or eat well like usual. It's been hard not going to the gym...
    imsoradalecki imsoradalecki 18-21, F 1 Response 4 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 Nov 19

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