Viewing 38 reply threads
New Forums
  • Author
    • #717015

      Hi Everyone and i hope you are all having a super week.

      Now the question for today is have you told anyone at work about your crossdressing? It is a hard subject to broach and you have to be pretty certain that who you tell is open minded and can be descrete.

      I have a good relationship at work with my collegues and a select few have been told and even been shown pictures. I get the usual comment such as ‘oh! you scrub up well!’ and i find it raises more questions from them as they are curious to know why rather than poking fun. On the whole, its been a positive experience but what about you? Has it been positive or a total disaster?

      Fiona xx

    • #717026
      AnnaBeth Black
      Duchess - Annual

      I work in a very testosterone drenched environment where the guys talk very negatively about transgender people.  There is little chance I would ever share anything with my coworkers.

    • #717030

      No I haven’t.  There was a person who I was going to tell, as she is open minded and understanding.   But she turned out to be a jekyll/hide personality, so thank god i didn’t tell her anything.

    • #717032
      Caty Ryan

      I’ve been retired for decades, but worked with my male cousin for many years in our family business. I used to keep all Caty’s stuff, (securely)  in my office and dress after everyone had gone home for the night.

      I once took a late after hours phone call and then forgot I’d left a black body suit “out”….

      We had a chat about it next day. I returned it to its “hidey hole” and from then on nothing was said. Tho he was at least smart enough to call ahead of time if he knew I was working weekends, as I frequently used those days as a chance to dress as well.

      Operating complex machinery in a dress and heels was quite a contrast…….




    • #717033
      Kelly Lee
      Duchess - Annual

      While I work from home most of the time we often do videocalls. I used to be dressed waist down but then I got tired of hiding it. I have a wife that’s sick (parkinsons and dementia) and using that as excuse I just told everyone about Kelly. No one have said anything even remotely bad, only “go for it” and so on.
      Our company then merged with another one and we have had several videocalls across the (former) two companies and I just show up as Kelly, no one seems to even notice.


    • #717036

      The group I work with is really small… I mean, I work in a very large warehouse with a lot of people but in terms of my position I’m fairly isolated in an office most of the day, and there are only 5 other people with the same job as me, and only 2 I see on a regular basis. I’m sure there’s a lot of my personal life I’d never share with my co-workers and this is one of them I just wouldn’t do. I’m very friendly with the 2 people I see on a regular basis, but I wouldn’t say that we’re friends… so I guess I wouldn’t really have anything to gain by telling them.

    • #717048

      I have not only told everyone at work and shown photos of Marianne but also daily openly dress to some extent and some days go in full female presentation supported by colleagues and management alike. I  have held the same position since 1995 and came out to everyone at once in 2018. As late as today a male colleague asked me about my upcoming participation in the Keystone conference and seemed impressed when  l showed him a photo of my gala dress.

      Ellen MARIANNE Tornander

    • #717050
      Angela Booth

      Yes I did it. I worked in a large organisation in a team of about 20. We were a good team and I got to know some quite well. The nature of the work involved some to work in sub teams and a lot of chat was exchanged about things not necessarily work related. I gained a lot of insight into lives and we even did a bit of socialising too. It was a mixed sex group and after a time I felt I could come out to one of the girls as she had some issues that I helped talk through with her. I decided that I would meet up for a coffee and show her  a few pictures of myself. When the day came I had a ‘what the heck’ moment and got dressed and went. She was waiting outside the coffee shop and I walked up to and stood by her. She was looking around and I said ‘Hi’ and she did a double take and then gave me a huge hug. I was spot on with her reaction and it went really well and she asked if she could tell a couple of others and my social circle increased and everyone kept it confidential. After leaving the job a few male colleagues contacted through social media and I told them too. Life got so much better for me after telling that one person.

    • #717058

      Actually yes I have , as my counsellor suggested I tell as many people as I’m comfortable with  about Ashley. So after I came out to closer family members I thought about going outside the family. A year ago now I let my female boss know all about my crossdressing as we were fairly close and figured she would be understanding. Turned out I was right, she is very supportive and thanked me for sharing such a huge secret with her. She asked a bunch of questions and asked if I had any photos of me dressed. We sat in her office for almost a hour looking at a ton of photos. She loved them and still now she will ask every now and then to see any new ones.  She said I have nicer legs than her and a way nicer wardrobe.  Lol. She did ask if if I may be transgender and if I was to ever come out she would support me through it.

    • #717060

      I work in an office environment and several years ago it was decided we would all dress for Halloween. I procrastinated on purpose so I had little chance to come up with a costume and could convince my wife to let me dress as a woman. We decided I could go as Ragetty Ann. I underdressed in bra, panties, and pantyhose. My wife said she never saw a Ragetty Ann with breasts but I convinced her to let me pad my bra. I wore a semi-sheet white blouse underneath a navy blue jumper I borrowed from my wife. I wore white knee socks and black Mary Jane heels. My wife helped me style a wig with pigtails and she advised me on my makeup. She said I looked cute for a last minute costume. I was one of three men in the office and the youngest. There were about a dozen women in the office with three of them about my age. When I arrived at work they couldn’t believe I would dress up like a girl. Everyone paid me compliments and I was soon invited to join the three younger women for lunch. I had such a good time that day. At lunch the other girls asked me lots of questions. They were so curious. They never came out and asked if I was a cross dresser and I never told them I was. But I never told them I wasn’t and I’m sure if they used their female intuition and read between the lines they had a pretty good idea I enjoy dressing as a female. A couple of years later I dressed as Little Bo Peep and by then I’m sure they had no doubt but I never confirmed their suspicions.

    • #717066

      In short no. My previous job that I had and where I worked for 23 years was in an aerospace / defense company, which was dominated by macho culture (or as AnnaBeth says testosterone drenched environment). Any “alternative” lifestyle was put down on a regular basis in conversations when those came up. It was very conservative politically as well. It’s one that everyone would recognize and hasn’t been doing so well lately. Luckily, I left there and have now been in an IT services company which a 180 as far as culture and I feel I fit in better. While there are certainly team members on the LGBTQ+ spectrum I haven’t found an opportunity to connect with anyone to address my dressing. Since COVID it’s 95% work from home, travel to visit clients and occassional work meetings. When at home, I regularly dress up on days when I don’t have to be on zoom calls.


    • #717097

      Hi girls,

      As many of you here on CDH may be aware, I am transgender. When I knew I had to transition and would be doing it where I work at a government building, I announced it to the entire staff of over 500 people, 95% women. Quite a number of the ladies said they weren’t surprised at all as they had already “figured me out as being “just one of the girls.” That was over a year ago and now, I am just “one of the girls.”


      Ms. Lauren M

    • #717099
      Cassie Jayson

      As a matter of fact I have. I am a mail man at the Post Office and this past summer I went in and told our post master. This past Columbus Day I went in ( the Post Office is closed, but they run some of the behind the scenes tasks) to put in a request for a day off the following month. I was wearing one of my favorite dresses. Saw our Post Master a supervisor and a couple of clerks. I have also told a few others, but I am sure most know or suspect.

      . Cassie

    • #717113

      Yes, I have come out to quite a few co-workers in the relatively recent past…maybe a dozen or so. In all cases, the individuals were kind and expressed support. Of course, I am no mind reader, so who knows what they really were thinking. I have maintained contact with most of them, so I guess thats a positive indicator.

    • #717121

      No. Although my company has policies about gender and gender expression, I don’t plan to go in wearing obvious women’s clothing. It doesn’t change human nature for people I know (and have known for years) to ask why I am wearing a skirt or a dress, and for people I don’t know to look at me even if out of curiosity. Company policies also don’t apply if I have to make a stop along the way home.

      I am usually dressed up on days I work from home, but it is rare that we do video calls.

      In short, my dressing is private, it is for me, and it doesn’t impact what I do, so it isn’t anyone’s business.

    • #717169

      Short answer is no but it reminds me of a story.  A few years ago I was in a car with a few people from different companies that I’ve known and done business with for many year going to a industry meeting.  I don’t know how the topic came up but one of them started talking about an old friend that retired some time ago.  After he retired he came out to his old friends and even sent them videos of him on some of the old show like Donahue and such.  He explained in a letter that he was a straight cd and had been forever.  Why he did this I’m not sure exactly but thought wouldn’t it be great if we all did that and people realized how many of us there really are.  The person telling the story is a bit of a self described southern redneck who had no issue with it at all.

    • #717170
      Samantha R

      I have seen the way my co workers have reacted to others that have come out in my work place, so no. I don’t want to deal with all that.

    • #717226

      Yes, I have many folks at work that know I dress. In the past year I have started underdressing everyday at work. In the last few months I have been wearing some makeup and it is obvious. The strange thing about this is that my family doesn’t know but I am sure they suspect and don’t talk about it. My oldest daughter actually works at the same hospital I do.

      My work friends are some of my biggest supporters of my dressing. I often ask their opinions on outfits, talk about fashion and shopping. One thing for sure I have this life laid out backwards from most.








    • #717239
      J J

      No, at least not intentionally. I once left my office laptop with a page of thumbnails open. I know my office manager was in my office but whether she saw them or not, I don’t know. She never said anything and no offer staff members let on if she told them. I am retired now, so it really doesn’t matter. Plus, I have underdressed at work for years, so I imagine somebody noticed something at some point, but again, they never let on if they did. I had a great staff, so it likely would’t have mattered anyway.

    • #717248

      I have told a couple of people at work and they were receptive. They asked me a few questions and they told me that they had suspected that I dressed and were supportive

    • #717251
      Eva B

      That would be a hard no.  I have been in public education my whole career.  That option would never fly teaching kids in public schools here in the US.

      • #717265

        It is interesting how public education supports children coming out, but not its educators.  I taught for over 20 years, and never imagine coming out until I left education for the private sector.

        MacKenzie Alexandra

      • #717578

        I work in public education and for the last year and a half we’ve had a transwoman on our teaching staff and it was totally fine. No staff drama, no parent drama, and the kids in my school adore her. I think it really just depends on the community, and in Washington you can’t be discriminated against on the basis of gender identity or expression. That said my professional life is wrapped up male me, and I don’t plan to transition so I won’t be sharing my gender identity with coworkers, it would just be to much of a distraction to my work.

    • #717263

      Where I use to work (retired now) they were fine if you came out as gay or as a lesbian. But anything else was not accepted. Very conservative family operation. Thank god my boss was the sensible one in the family. But I trusted a friend at work I had know for 12 years. Discussed Lisa in confidence, in turned he told others about me and it wasn’t long before the whole building knew, rumors started. . . You know the drill. I hate that I have never been able to trust anyone. Unfortunately, my wife, well the woman can’t keep a secret. She talks without thinking, so I have learned never to discuss anything I don’t want others to know. This is the only place I know where I can speak openly and not worry about others.

    • #717267

      Do not see any reason to share that information about me unless I woudl plan coming to work dressed up, which I do not plan to do  So no to sharing with anyone at work

    • #717558

      I have told two people at work.

      The first was before Christmas,  she was a temp working reception.  We started talking and to was telling me about her wife and their son.  I talked to her about her nails.  I showed her a picture of my painted nails.  She then told me about her Transgender Borther Sister, and how she loved her. She gave me her number to chat if I needed to.

      This past week I was working with a production team member who have beautiful fake nails great makeup and hair. One of her nails broke.  We talked about her nails, and how great they were.  When she saw my long nails she asked me why.  So I showed her pics of my nails. She was really cool.  We talked about nails.  The next day I talked about going to a drag show next week.  She asked if I was going dressed. I showed her a pick of me in a dress I want to wear.  She responded with I want to do your hair.

      Working in a factory as a part of leadership, I am not sure how it will go over if they find out I would rather be there dressed as a woman.


    • #717700

      [postquote quote=717026]
      It could be a great opportunity for you to slowly start wearing some feminine items to work and to teach them  You could start slowly by wearing just nail polish for women’s shoes. This is exactly what women did when they started wearing men’s clothing and that is how they earned their fashion freedom. The only way to effect change is to be different from the herd.



    • #717820
      Kirra W

      I’m working in an open-mind, LGBTQ+ 🏳️‍🌈🏳️‍⚧️ friendly company, and I’m still balanced on the fact that I should share it with my teammates and management.

      But I’m strongly thinking to “invite in” at least one of my colleagues.
      We have some really good moments, we meet often outside of the office hours, for drinks 🍹 and/or dinner with his partner. He knows me well so far, and I think this may be the right person to start to introduce Kirra in my work environment.

      And so far, it will be more easier that doing it with my family 😉


    • #720734

      It’s not that I “dared”, it’s that an opportunity was presented to me; so I told a co-worker about “Brittney”.

      I work industrial security at a chemical plant; not a “glamorous” place and with a dull uniform. My co-worker was a cis-woman and one night she was running a little late and didn’t have time to apply her make-up at home. We had a “slow” night, so she started doing her make-up at her desk. Her and I had developed a “work place” friendship and she started explaining why she was doing her make-up. In a casual remark; she said “that since I was a guy, I wouldn’t understand”. I replied back saying, “You would be surprised. Do you mind if I show you something?” I showed her “Brittney’s” “Make-up, close up” photo that’s on my Public Photo Page; I have it stored on my cell phone. She said I looked amazing and it was the most she had ever seen me smile. I told her everything about “Brittney” and answered whatever questions she asked. She thanked me for trusting her in revealing my inner “gurl” to her and that she would accept me for who I was and that she would keep my “secret”, since I didn’t present as “Brittney” at work.

      So it was a discussion about make-up that allowed me to tell a co-worker about my “crossdressing”.

    • #720796

      Hi Fiona
      Not exactly work as I have been retired a few years now but I continue to sit on
      a Committee related to my former work responsibilities where most of my Committee colleagues are retired people that held senior roles in the industry in which I worked. As I am still in the closet at home I decided that Rachel needed some exposure to real interaction with others so last year I advised my fellow Committee members that I was a Crossdresser and that I would be attending future meetings as Rachel. Whilst not as bold as telling someone at a regular workplace these are people that in some cases I have jointly sat on the Committee with for up to 29 years. I have experienced no staring or difficult comments and even the Administrators that support the Committee have got used to addressing me as Rachel in emails.

    • #720814
      Amy Oxley

      No way. I work in construction, and although my younger colleagues probably would not care, there are too many old timers in senior positions that would make life a misery.

    • #720827
      Stevie Steiner
      Managing Ambassador

      Yes, I have!  I am lucky to have a couple of co-workers that are part of the “LGTB” community at work.  They opened up to me ( I am super approachable ), and I happily did the same to them.  It is truly liberating doing so.

      And, I will also stand up and defend these co workers if any phobic comments surface!  ( damn straight I will! )


    • #722019

      I never actually told anyone at work but, it did come out. I had to fix a computer station one day, and when bending down and getting under the desk my panties were showing. When I stood up the lady told me my panties were showing and I should tuck my shirt in. I was a bit shocked and told her thank you. Later on she came to my office and apologized. I asked her for what. She said putting me on the spot like that. I told her its ok I wear them willingly. She laughed. Them said that she had known for a while and so did some of the other people. I asked how. She told me they can see my panty lines and she had seen them poke out before. So pretty much the whole office knows I wears panties.

      • #728473
        J J

        I have always wondered just how common this sort of thing was. I have little doubt people notice things if just at a glance, but in a work place environment with daily interactions it seems it would be noticeable.  I wore panties exclusively for years, and a bra often, so I would think somebody would notice. If the did, so what?

    • #728280

      I applied and interviewed as Dani. When I came in for an application I was wearing shorts and a tank top but nothing over the top. When I interviewed I wore slacks, a blouse, and heels. No problems. I work in the office at a distribution center. Management has been very supportive and there has been little friction. Some of the girls like to wear short skirts and some pretty revealing tops and like to flirt with the guys. Work is about the only place I keep things pretty boring. I get along well with the other girls and it seems the guys don’t really care, but I am sure I have been and may still be a topic of jokes or other conversation but it hasn’t reached my ears yet.

    • #728288

      I come into the office dressed up sometimes. Last year I was able to come in once or twice a week, but this year it hasn’t worked out. I work in a pretty accepting place, and I appreciate how unusual that is. The biggest surprise coming in was how few people really even cared. I thought there might be questions or conversations about it (I was actually kind of hoping) but most people didn’t seem that interested. Usually it was, “why are you dressed like that?” and I would say, “It’s just for fun, it’s something I like to do.” And that was it. Some of the women compliment me on my clothes sometimes, but I always feel it’s just because they’re trying to be nice. On the whole, nobody really cares.

      • #729159

        My experience also, I would wear my girl things to the office several times a week. Never had any problem.

    • #728294

      So the technical answer is ‘no’, but also there is a bit more to it. I have an OKCupid account up as Jenny and I have matched with no less than 2 of my coworkers on there where we have chatted about other stuff. They have never let on that they knew it was me, but it has always had me wondering if they knew.

    • #728404


    • #728895
      Sarah Lee

      Yes, every chance I get. Everything I  wear with the exception of my  socks and work shirt is from the woman’s  department. Sometimes  I’ll wear some lipstick. Usually black or coffee color. I had to ask my boss a question about  a part on the shop floor. He answered  me  then on the way out I hear him mumble,  I can’t believe  he comes in here like that. I later told one of the office ladies what happened.  She threw the stuff in her hands down and was ready to go to HR. I told her it was OK. That was the worst that’s happened.  The policy where I work is not to discriminate  because of  race,  color, religion, sexual orientation or preference. I’m about to talk with the plant manager and  HR. I’m ready to start going in on weekends en femme. There are a few people (all guys) who won’t talk to me now. Whatever,  your loss. I’ll be over here, doing my job looking fabulous  the whole time.

      • This reply was modified 11 months ago by Sarah Lee. Reason: Misspelling
    • #729038

      One of my work mates has been a close friend for 15 years or more. He knows.
      For a shor while we had a young (21) trans girl joined us on a 6 month contract. She lived near me, and was suffering transphobia from a group of teenagers. This was making her unwell. This girl worked closely with my friend mentioned above. My friend told me of this girls problems and I offered to help. I took her aside and gave her my phone number so if she got hassled again (windows being smashed etc) she could phone me and I could be there in minutes. It was during this conversation that I told her of Cerys. Thankfully, the harassment stopped, and the young girl could go on and live her life in peace.

      A few of my close friends from a previous job know of Cerys, but they only found out some years after we all departed the company. One has met Cerys.


    • #729039

      One of my work mates has been a close friend for 15 years or more. He knows.
      For a shor while we had a young (21) trans girl joined us on a 6 month contract. She lived near me, and was suffering transphobia from a group of teenagers. This was making her unwell. This girl worked closely with my friend mentioned above. My friend told me of this girls problems and I offered to help. I took her aside and gave her my phone number so if she got hassled again (windows being smashed etc) she could phone me and I could be there in minutes. It was during this conversation that I told her of Cerys. Thankfully, the harassment stopped, and the young girl could go on and live her life in peace.

      A few of my close friends from a previous job know of Cerys, but they only found out some years after we all departed the company. One has met Cerys.


    • #729205

      I had commented earlier that I came put to one person at work.  As of last week it seems that people at work know and are talking about it.  See my story “Called into the  Bosses Office”

      After my panic calmed  I am ok with this development.

      Durring this mornings meditation my wife picked one about Gnish. The Hindu God of remover of obstacles.  The though came to me that the obstacle of not being out at work has now been removed. I am  now free to be me whenever I want now.


Viewing 38 reply threads
  • The forum ‘General Chat “Life as it Goes On”’ is closed to new topics and replies.
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials

Forgot your details?