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I Would Love to Go to Work Crossdressed

Personal Stories, Advice, and Support 492 People

    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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, 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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    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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    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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    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 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 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, 2014

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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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    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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    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 love working out, but food is too good.
    cnguyen138 cnguyen138 18-21, M Jan 8

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    Yes, I would so love to be the woman that I was meant to be. As I've come to learn that really am a woman, and always have been, at least in mind and spirit, but not in body (yet...
    DawnR59 DawnR59 51-55, T 4 Responses Dec 28, 2014

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    I would love to and have done before. Sometimes I just like to take a day off from the world and spend it in bed with my partner. Reconnecting, chatting, laughing, loving! Only...
    ultimatehacker ultimatehacker 26-30, M Dec 28, 2014

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    I think I will faint if I actually meet this hunk of a man! Like, seriously. I'm crushing on him harder than I have EVER crushed on any man. Well, it's not so much Stephen...
    OlicityShipper OlicityShipper 70+, F Jan 11

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    I love dancing and would love to dance with him. He doesn't really dance but I am hoping one day that we will be able to dance together and have fun. Until then, I shall just wait...
    iwillfly iwillfly 18-21, F 6 days ago

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    I would love to have a platonic female friend someone to spend time with naked doing things like sunbathing, gardening and talking about things no sex just friendship.
    nudiepeople nudiepeople 56-60, M 16 hrs ago

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    Honestly, I am so glad I have supportive friends. In the earlier years of high school, I would work out so much, that people said I was trying to look better and be skinnier. I...
    sammy267 sammy267 18-21, F 1 Response Dec 27, 2014

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    My wife and I had discussed this before we got married. So, the day we got back from our honeymoon I sat down on the couch and told her to "*****". From the look on her face I was...
    Redradioflyer Redradioflyer 26-30, M 4 Responses Jan 3

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    I'm bored today, off work and home alone. Wish I had a man here to lay behind me up against my body and kissing my neck! I'll find him soon. OOooOhhhh yessssssss. ;P
    jerzshorecoll21 jerzshorecoll21 22-25, F 14 Responses Dec 28, 2014

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    I have worked out since my early teenage years. But, life got a little busy and I stopped. Still stayed active, playing soccer, the occasional run. Always thought I was still in...
    Confusedjoe Confusedjoe 31-35, M 2 Responses Jan 10

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    I workout almost everyday go to the gym burn about 1000 each day is that too much or to little? After my workout I also try to watch the things I eat to not have more calories than...
    blessedandproudgirl blessedandproudgirl 16-17, F 2 Responses a week ago

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    I am working on doubling my weight.... 150 to 300....I'm 215 now ?? looking for people to gain with.
    Jumpflood Jumpflood 22-25 23 hrs ago

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    I am a big kid at heart (so much so that I have a trip to Disney World with some friends at the end of the year) so I love that working with 0-5's means I get to spend the day...
    RachiiM RachiiM 22-25, F 5 days ago

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    Day two of working out after taking a two week break. My body is sore and my hip hurts for some reason. That's what I get.
    Jenner43 Jenner43 41-45, F 5 Responses Jan 4

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    After shifting to vegetarian diet I feel so much energy. As I eat in a healthy way my body becomes purer and I feel so good when I work out.
    nataliawww nataliawww 26-30, F 3 Responses Jan 7

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    I workout in the morning and evening too. Good results don't come easy.
    deleted deleted 26-30 1 Response Jan 13

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    its been a constant thing lately.. instead of worrying about stupid ****, i can just work out and listen to music. it takes a lot of things off my mind
    Ebolaa Ebolaa 16-17, M a week ago

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    Just did a little traps workout today because I was feeling out but still wanted to get something in.
    mattywheels25 mattywheels25 26-30, M 5 days ago

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    I don't think I'll ever be able to truly put into word what I feel ... There is a power, maturity, sexiness to a woman over 40. Older doesn't mean old, it just means not a child...
    Theworldisminenow Theworldisminenow 18-21, F 4 Responses Jan 8

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    That would be so comfortable and cuddly, the cute little pals enjoy a human within them and feel safe, and I would certainly love them to be around me too, but first, the husky...
    iTetra iTetra 13-15, F 3 days ago

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    My love affair with India is over. It's quite sad really, another of those facts of life that you wake up to. When the dream or illusion of how you imagine something to be meets...
    Carissimi Carissimi 56-60, F 3 Responses Dec 31, 2014

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    Its not that im a perv, well, no more than any other guy, but yea, i cant think of many guys who wouldn't love this.
    MrWinstonSmith MrWinstonSmith 22-25, M 2 Responses Jan 2

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    I know it may sound crazy to some, but I would seriously love to move to Japan..even if it is just for a brief amount of time..the scenery there is just so very beautiful...the...
    alb1114 alb1114 36-40, F Jan 8

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    My wife of 32 years died then a month later her mother. I met a child friend and married 6 months later. I kicked my 26 yo son out of the house so we could be newly weds them sol...
    lostokie lostokie 56-60, M Jan 16

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