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I Would Love to Go to Work Crossdressed

Personal Stories, Advice, and Support 529 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 13 Responses Feb 16, 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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    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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    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 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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    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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    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 6 Responses Apr 24, 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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    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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    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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    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 3 Responses Feb 11, 2009

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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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    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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    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 9 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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    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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    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'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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    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 1 Response Mar 18

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    Related Experiences

    I have a 16 year old sister. I get aroused when I look at her. She is hot in a bikini. I bet she would want me in her. How would you guys out there get into her pants
    Etaube2015 Etaube2015 22-25, M 1 Response 23 hrs ago

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    Makes me feel like I accomplished something in a day lol
    AustraliaGuy AustraliaGuy 18-21, M 1 day ago

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    I'm not even gay (this one, I admit, does makes me question that though, I have it mapped out IN MY MIND but I would like to see it in reality) I'd like to see the gayest fantasy...
    PorkythePig PorkythePig 18-21, M 1 day ago

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    I love a friends like that it would be the best thing ever
    dresscross dresscross 51-55, M 1 day ago

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    Well maybe not love it but don,t mind it but i,m having my kitchen redone and this guys have it a mess...Ill be all night cleaning after they leave...But i know they have to make a...
    MARRIEDBUTBI MARRIEDBUTBI 26-30, F 1 day ago

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    Tomorrow is my birthday :) all i want is to find the girl of my dreams that loves everything that i love. a girl that would cuddle up to me all day and push her tummy out as far as...
    garrett1990 garrett1990 22-25, M 2 days ago

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    I want to taste a girl. Would love to feel my **** rubbing against hers
    deleted deleted 26-30 2 days ago

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    Nothing like sleeping in and heading to the gym to work out your frustration!!
    HarleyQuinn251 HarleyQuinn251 31-35, F 1 Response 4 days ago

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    If someone would love me then definitely I'd love her back more than my life but it must be real love not just attraction or lie..,
    saysorry saysorry 22-25, M 5 days ago

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    I'm so lazy.... 😣😑 But I guess it's alright 😂😆
    DoorMattress DoorMattress 13-15, M 6 days ago

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    I've been doing a lot of writing, hoping to write & publish a book & would love to get some outside opinions. (Because with friends/family, you're never sure if they're saying it's...
    deleted deleted 26-30 6 days ago

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    Does anyone else get a little horny when they work out or is just me...
    deleted deleted 26-30 4 Responses a week ago

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    This is strange...I feel very attracted to men sexually and romantically and it used to be more guys sexually...but now I feel like women turn me on more than men. I guess I would...
    niahhydra niahhydra 16-17, F 1 Response a week ago

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    Yeah... and I wonder what her feet would smell like?
    FeetHunter FeetHunter 22-25, M 1 Response a week ago

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    I'm a weak boy curious about what you would do to me if I was there? How would you humiliate or bully me?
    deleted deleted 26-30 Jun 23

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    I love it when I see a woman who is thirty or early 40's and is a little heavier, working out. It is sexy when a woman is trying to get more fit. The baseball cap and pony tail is...
    existiantiallycertain existiantiallycertain 46-50, M 1 Response Jun 22

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    I'd like to wake up in the morning and have a huge belly as someone force fed me so much food the night before I'd wake up and my belly would be so huge I wouldn't be able o move I...
    DemonLugia DemonLugia 18-21, M 2 Responses Jun 22

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    please I would love to go on a date. With someone older , intelligent, and brains really turn me on and then we see what happens . or just a coffee date
    Akinyim Akinyim 41-45, F Jun 21

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    I have a travel blog that accepts guest posts. Does anyone would like to share your travel tips and story on my blog?
    ldrmiracle ldrmiracle 22-25, M Jun 21

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    My version of a FWB would be the right woman with whom I could swap erotic massage.
    MarylandGent MarylandGent 56-60, M Jun 20

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    So I just had a date with a guy, and he's happened to be white. (I'm sorry for all the Asian men out there who feel like all girls are desperate for white man, but things happen...
    vi491042 vi491042 18-21, F Jun 20

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    I enjoy a woman with a big belly....I love kissing and massging it with baby oil...
    AfanOfbigNaturals AfanOfbigNaturals 46-50, M Jun 18