I Would Love to Go to Work Crossdressed

Personal Stories, Advice, and Support 630 People

    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
    10 Responses Feb 16, 2010

    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, M
    3 Responses Aug 17, 2015

    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
    1 Response Jul 17, 2013

    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, M
    3 Responses Aug 24, 2015

    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

    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

    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
    5 Responses Apr 24, 2013

    One of my biggest dreams is to be able to go to

    work dressed in a skirt or dress. I would never have the need for men's clothes again.
    deleted deleted
    4 Responses Sep 21, 2015

    Having worked in environment

    that is predominately female I always dreamed about going to work dressed as a female. Many times at work I fantasized that I was also dressed like my co-workers. Wearing either a nice pantsuit or dressed in the comfortable dress that my co-workers did. However it was...
    deleted deleted
    1 Response Oct 9, 2015

    The closest I can get in my line of work is to

    wear my bra, breast forms, and panties under my work clothes. I would love to go full Jena mode. I am a highway construction engineer.
    Jena1976 Jena1976
    41-45, T
    2 Responses Dec 31, 2015

    I have been fortunate enough to go to work

    once fully dressed. It was Halloween and I dressed as Alice in Wonderland and it was awesome. My fellow coworker cross dressed too. She was the mad hatter. I'm looking for ideas for next Halloween. Any suggestions?
    sexyalyssagurl sexyalyssagurl
    41-45, T
    2 Responses Feb 21, 2016

    Nice miniskirt, fishnet stalking

    and high heels. drive all those redneck boys crazy.
    SweetSarahSawyer SweetSarahSawyer
    51-55, T
    6 Responses Feb 21, 2016

    Just thought I would give you an update in this

    post as requested. I am now in my fourth week of going to work wearing skirts and tights. I have put a pic above if me at work in a black skirt and grey tights. I have been to two management meetings like this. I have walked about the site, been seen by hundreds of people...
    jeffreyrichards2015 jeffreyrichards2015
    56-60, M
    2 Responses Oct 13, 2015

    I've gone to work at various jobs dressed

    and enjoyed it a lot. Currently I am driving a taxi and would love to be able to but am sure the company would have to fire me after any complaint or objection from passengers. Just to try it last Halloween I tried it and sure enough even tho no one should have several males...
    amandatrane1 amandatrane1
    51-55, T
    1 Response Jan 31, 2016

    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
    5 Responses Sep 10, 2011

    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

    To wear a dress and hose

    and heels to work every day. The feeling of the a.c. blowing on my legs and under my dress. Most of all to be able to complain at night how my heels hurt my feet. Total heaven.
    jennloves55 jennloves55
    61-65, M
    2 Responses Dec 30, 2015

    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
    Sep 21, 2012

    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, M
    1 Response Aug 15, 2015

    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
    3 Responses Nov 29, 2014

    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, M
    3 Responses Aug 21, 2015

    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

    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

    Well the cat is well

    and truly out of the bag now. I have sent an all staff email to let everyone in the company know that I will be returning to work next week with a different gender expression. All positive replies so far!!
    jeffreyrichards2015 jeffreyrichards2015
    56-60, M
    3 Responses Sep 17, 2015

    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
    61-65, M
    2 Responses Mar 20, 2013

    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
    51-55, T
    2 Responses Oct 8, 2013

    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
    46-50, M
    1 Response Oct 24, 2012

    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
    1 Response Mar 18, 2015

    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, M
    4 Responses Aug 28, 2015

    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

    I suppose that I should not post in this

    category any longer because the title is I Would Love To Go To Work Crossdressed. And today I did. So from now on I will be going to work not wearing trousers ever again. I chose a brown skirt, plum tights and trainers. Pic above is me at my desk. So I have been seen by hundreds...
    jeffreyrichards2015 jeffreyrichards2015
    56-60, M
    4 Responses Sep 21, 2015
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