Jessie’s first days at work

A diary of my adventures of going to work for the first time as woman.

Last Thursday

I came out as bigender to the boss, which went very well and her only concern was flipping back and forth with customers. But I do most of my work email or phone aside from 3 months a year where I’m a very public face. So I can be a man then easily. But we agreed to meet for drinks so she could meet her newest female employee after she gets back from a week long trip.


This week I tell my other co-worker. Well there is a fourth but she is leaving in a few weeks so I can push it off with her right now. Anyway my other co-worker is at the other end of the millennial generation from me, I’m the very beginning and she is the tail end. On Monday she comes into my office and we talk then I say I have something I need to talk about but I need you to keep it on the down low. I stammer, then just take out my tablet and show her pictures. Now saying she was understanding and supportive would be a massive understatement. After the usual questions on names pronouns etc, we talk about the good places to buy jeans. Then I mention that I am planning on Jessie coming to work but need to plan it out with the boss. Then a discussion comes about where it is determined that since it’s only her and I for two days this week Jessie can come in earlier than planned as I have to be able to be me. So the date is set and in just two days Jessie will be going to the office. And she says she is excited to meet the other half of her coworker. Feeling anxious, excited, and happy. A bit like a kid on Christmas Eve.


Tomorrow is the day. I’m ready for this? I’m anxious but ready. I’ll have to get up early and get a good shave and get my makeup just right. Does my outfit look good? Is it appropriate? I put it on and check, take a couple pictures. Yes it looks good and is appropriate for the workplace. Ok you can do this. Try to sleep through the anxious excitement. Don’t need bags under my eyes on the first day.

I’m surprisingly calm and content. I packed my tote bag and purse. Double checked everything leaving nothing to chance. I’m am more at ease with it with each passing moment. But Some problems falling asleep, kid on Christmas Eve.


I’m up! Final few hours.

I expected to have to talk myself up and look myself in the mirror and tell myself to get my big girl panties on. It actually feels like a normal day, which is suppose is good. Shaved, moisturiser, makeup, clothes, earrings, necklace, bracelet, and finally the wig. Check in the mirror and it seems everything is in order, not obvious bulge, check with spouse she gives ok and off I go.

Not my greatest picture, but feeling pretty good.

The drive to work was reasonably uneventful. Pulled up and parked at work and walked in. I was a few minutes early just so I could acclimate myself a bit. It all feels very normal.

The only other co-worker comes in and says today’s the day. She is just outside my office and I say good morning, she says good morning and today is the day. I asked if she was ready and she said I was. I come out, she gives me a few compliments and pointers. Then we go about our day. It is all very normal.

I sit at my desk and work on my computer, the long synthetic hair of my wig brushes on my shoulders. A reminder of who I am but it again feels just normal. I go and talk about work my breasts sitting proudly on my chest face framed with my red locks of hair with no difference to workflow.

The half day for me is coming to and end, we talk for a bit about how it went. I suggested maybe the next day. She says yup, I go home and just feel normal as I choose my outfit for the next day.


So another day at the office, but it’s only Jessie’s second day. Different outfit today, the day before I had selected some skinny jeans and a longer shirt so I would not have to worry about down there sticking out. Today it is a white top and black dress pants, very office appropriate but no room for error. While the day before my loose top did not highlight my breasts this one brought them right out and I even had cleavage going on. But I am feeling confident so I go for it.

Make up is a little off but I think I’m looking just about as good as I feel

I am in a few minutes before her again but that’s fine I just do my normal morning things. She comes in and she says she likes the top on me, I say thanks, she then said I’ll now be able to participate in the women telling each other their outfits look good thing. Yet another adjustment as before had I mentioned an article of women’s clothing looking good it may have just gotten me in trouble. So much to learn and adjust to. We go about our work for the day and it all feels normal, though I am pretty sure she was also making sure not to draw any attention to it so I would not feel out of place. When I did bring it up she was happy and engaged.


I am actually really happy with how it all went down, obviously. And in case anyone is wondering what the boss will say when she finds out, likely will be more insulted she wasn’t there for my first day than anything, I mean we have known each other for nearly 20 years.

So what about going forward. I think I’ll make a deal where I keep a change of clothes and make up remover around in case I need to be man mode since I am publicly professionally a man. And then plan much more time for Jessie to be in the office, a few days a week maybe to start. After all I have a lot of clothes to buy to fill out my wardrobe.

One thought on “Jessie’s first days at work

  1. This is the one that I thought really merited a comment primarily as a compliment to you and to the understanding and acceptance that you have received from your wife and from your co-workers. I suppose your work environment is somewhat under your control and that it is not all that large or constantly in the public eye. That really gives you the ability to express your bigender nature. Now, even if you are presenting as a male, you will be granted some of the female priviledges that no one ever discusses. I suspect that there will be some days when you just do not have the time to properly dress or your lack the energy to do a proper shave and you will go in as a guy. You can wear hose under slacks without socks, you can keep your nails done, etc. I am so proud (and partially jealous) of where you have been able to bring your dressing. You give us big guys hope and encouragement.

I love to hear from people who read my blog, even if your not in agreement with me. Your comments may spur me on to write something else so please comment.

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