What’s being transgender at work like? Update!

Hi Everyone, Welcome or welcome back! If you’re new here, my name’s Andy and I’m a trans woman sharing my journey here on YT!

Some of you might recall I came out at work a little while ago and I figured it’s a good time for an update to all of that.

The good news it’s generally good news. Although things haven’t been all sunshine and roses.

If you would like to support my channel you can buy me a coffee here: https://buymeacoffee.com/transgenderpositivity

For those of you who do, I’ll send you an extra thing I’ve created as a small gift! Otherwise have a great week and see you same time next Sunday

Trans people are not defined by their transitions.

@gloria_swansong #stitch with @mags_a_million Let’s clear the air on what Transgender means and what the movement is all about. #trans #transnonbinary #transhistory #lgbtqeducation ♬ original sound – Gloria_Swansong

Let’s clear the air on what Transgender means and what the movement is all about.

Transgender is about transversing genders, spanning the space between male and female. It is a broad term and doesn’t specifically define one gender expression.

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Do you remember the first time?

Hi, I was chatting with some of my members online the other  night and we got to talking about our first time. I don’t think any of us really knew what we were doing at that time. I was about 5 when I first tried on a pair of black panties. My cousin had been over, and they’d been left.

I think my mother must have washed them and put them in my draw by mistake.  Either way I found them, and realised they weren’t mine.  I tried them on all the same, and I can remember thinking it was naughty. I can also remember getting an erection – which was definitely a little strange.

For some of us, it was our sister that played ‘dress up’ with us. For others it’s some other situation completely. 

We all have a different path into this – and for each unusual start there’s an unusual outcome.  I know so many men who crossdress, and hide it from their wives, only to find later (when their guilty secret is discovered) that their spouse really likes the fact that they like to dress up. And of course there are the ones that go the other way.
Of course we all have a different path into this – and for each unusual start there’s an unusual outcome.  I know so many men who crossdress, and hide it from their wives, only to fnd later (when their guilty secret is discovered) that their spouse really likes the fact that they like to dress up. And of course there are the ones that go the other way.

In the end, we all know we just have to be the person we’re meant to be – and find ways to accomodate that. There’s good ways and bad ways to do that.

I’ve just added a new page to my site that will help people understand a little about this. On my site you can tell your own story in the comments section of the following page – https://fionadobson.com/my-first-time/.  You might find your own story is not so unusual. It’s a good thing to share.  Don’t forget to register on the site. That way you’re sure to get a lot more out of it.

If you are interested there’s a little about my own journey here: https://fionadobson.com/the-three-reasons-i-couldnt-stop-myself-from-crossdressing/

Ironically, it’s often not until later in life that many people embrace this behaviour. Perhaps it’s just when we feel more comfortable with it.

Now, Sylvester, my mechanic has just pulled into the drive.  He wants me to take a ride with him on his chopper. Have a lovely evening!

🙂

Fiona

The Apartment – a ghost story.

When Jeff returns to his old apartment he finds more than he bargained for. This ghost story was written for http://Fionadobson.com – the transgender blog you’ll love even if you’ve never tried on your sisters panties.

Fiona

PS – If you haven’t signed up for my basic program you can do so absolutely free below.

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CONSPIRACY | Contrapoints

Context note: This video discusses misinformation for the purpose of pointing out that it is misinformation. [captions in progress] Support this channel: https://www.patreon.com/contrapoints

Sylvester couldn’t get his chopper out!

What a busy week it’s been. Poor Sylvester has barely even got his chopper out. He’s looking most frustrated.

I’ve told him, there are times when circumstances just don’t allow a good ride, and it’s times like that we have to do the preventative maintenance. He usually looks despondent when I say such things, and then goes off to grease his nipples, or something. I have no idea what that is, by the way. Anyway, perhaps the weather will improve and he’ll be able to get out on his bike.

We are living at a strange and dystopian time. The US is not what it once was – we might as well accept the fact. Al l that said, this is not a time to give up. It is the time to be the hope that seems so absent for most people. We can do that by being kind, considerate and by being ourselves. Our existence is resistance.

So, what can we do? Right away you can familiarise yourself with this – https://fionadobson.com/the-three-things-you-can-do-right-now-to-advance-transgender-rights/ – which is a good starting point. If you live in an area which has no pathway to support for a candidate that could get themselves elected, then I would strongly suggest backing a candidate in a location they may be able to get elected, even if this is far from you. Elections, contrary to popular belief, do not take place on one day. They take years. Supporting political movers and shakers who align themselves with out values does not have to happen just during an election year. The pressure needs to be constant, and our support of our people should be, too. If you live in the middle of a right wing enclave, you can donate to Zooey Zephyr, in Montana and lend her your support. Those of us outside the USA can’t donate to support US candidates, there are rules against that, but we can look to people who are advancing trans rights in our own country and lend them whatever support we can. Sometimes this is monetary, sometimes by volunteering, and sometimes simply by expressing support for their message.

We are definitely living at a strange time in history. However, we’ve always been here, and we will always be here. Supporting our sisters in any way we can is more important than ever.  This week I was travelling in the foothills of the rocky mountains, and in a small town hardly big enough to swing a cat in I stopped to buy a coffee on a very long drive.  To my surprise a trans girl came in as I was ordering my coffee. I would guess she was 20 years old. She looked lovely and I turned to her, complimented her on her lovely hair, and then told her how those of us who are older are so very proud of our young sisters. I said to her, ‘you carry a flag that we were unable to, and we admire you for that. When we are gone, you will carry that flag onward.’

She was so grateful. Many of us face a very solitary journey.  When we are able to express our support for one another it really helps.

With this in mind I am offering the first five people who email me at fdobson@zoho.com with the email subject line ‘I support my sisters’ free membership of my Whatsapp Group.  This is usually $10 a month, so it’s a substantial saving. Remember to check out the guidelines for the group chat.  It’s been running very well for years and is a supportive place for many members unable to find community elsewhere. If you’d like another opportunity to chat with others, you can do so by choosing one of the options on my Patreon and using the community chat there. Just remember to keep it respectful and clean. It’s about supporting one another.

You can get into my Patreon for as little as a dollar a month, and I could really use some new members there. Jump in and use ‘my back door’ if you want to be supportive.

Have a glorious week.

🙂

Fiona.

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If the bra and panties match…

Sylvester was already at my breakfast table as I hurried by to the laundry room. He’s doing some work caulking the tiles in my kitchen. I let him let himself in when he drops by early, as long as he puts the coffee on.

“Morning,” I said as I rushed by, late for a morning meeting at the office. In the laundry I grabbed a polka dot bra, and a pair of panties, then hurried back upstairs to dress properly. This happens to be one of my favorite bras. The HRT has helped my breast development nicely, and I like to feel comfortable.

When I came down to breakfast a few minutes later wearing a nice blouse and skirt, I noticed Sylvester looking at me disapprovingly.

“Well,” I asked.  “What’s the matter with you?”

“I couldn’t help noticing,” he said, “that your bra and panties don’t match.”

As I poured some milk onto my muesli I gave Sylvester a disapproving look.

“If I want you to look at my underwear I’ll tell you so!” I said. I think you can see the kind of thing I have to put up with.

“I couldn’t help but notice,” he replied. At least he had the decency to look a little awkward.

“Anyway, so what if they don’t match?” I asked.

“It’s just that I always think of you being better organised than that. Besides I happen to know you spend a small fortune on lingerie,” he carried on. “And, I mean – it’s nice if it all goes together.”

“Sylvester,” I said patiently as I sipped my coffee, “there’s something you need to understand. And I say this as one who knows, if your girlfriends, misguided as they may be, are wearing matching bra and panties, then they’ve already decided you’re having sex that night.”

Sylvester looked blankly at me as the realisation that he wasn’t the one making the decisions slowly dawned on him. 

“You mean, they decide before we even go out?” he asked.

“Yes.” I replied.

“But if that’s true, why do I have to do all the hard work, buying dinner and trying to get them in the mood?” he mumbled.

“Because we like that sort of thing.  We like you to work for it,” I said and put my empty cup in the sink.

“You’re saying, I don’t get to make the decision? She’s already decided what we’re going to do?”

“Bingo!” I said.

As I hurried to the door and picked up my back-pack, Sylvester smirked and said, “So I guess you’re not getting anything tonight.”

You know, Sylvester really can be quite coarse.

As I hurried out the door I said, “So, now you know what I carry in my back-pack!”

But that’s not the main reason I’m writing tonight. I thought I would just remind my friends and members, with all the troubling developments we see around us today, we cannot change the things people expose us to, the terrible news, the erosion of rights, however we can change the way we respond to them.

As hard as it sometimes is, choosing not let ourselves feel despair or anger can help us. Choosing to calmly observe, keep our powder dry, and pick fights we can win is a wise path. Of course, the news organisations want you to respond to news stories. It’s their job to present news in a way that gets a reaction. Take a breath, step back and try not to respond. Yes, that does mean dumping some social media. It also means being very selective with your news sources. I always use Associated Press and BBC, their coverage of most news being relatively balanced. Don’t forget, our existence is resistance.

Have a wonderful week,

Fiona

Dogwood Monarchist Society — Coronation, 2025. Drag show highlights.

This is a celebration put on by The Dogwood Monarchist Society, established in 1972 as a registered non-profit society to run the Imperial Court of Vancouver to support the LGBTQIA+ community. The DMS was recognized as the Mother Court of Canada in 1976, and is now part of over 70 courts across Canada, the United States and Mexico. Since its inceptions, the DMS has raised over $2M for deserving LGBTQ charities, and continues to thrive as an organization and as leaders within the Vancouver community. This is not only a wonderful event, Lenni (our very own) and her wife, Crem, are major drivers of the event and the organisation.

 If you want to support an organisation that gives to deserving LGBTQ charities you should consider even a small one off donation to the DMS. I know how much good their work does and can vouch for their integrity. Donate Here – https://www.paypal.com/donate/?hosted_button_id=3LZ29C5UQ795Q

It’s Coronation tonight.

Sylvester took the lovely Brazilian coffee I’d made and tried to look sensible as he sat at my kitchen table. It’s not easy to get him to understand the complexities of the transgender world, but I do my best. It’s rather like trying to teach a monkey to use a calculator. I eyed the bunch of bananas on the windowsill.

“Ok,” I said, ever patient. “I’ll try to explain it again. Think of it like this. I am going through changes.”

“I’ve seen your boobs!” said Sylvester.

“Shut up,” I replied. You know Sylvester really can be quite coarse. “There are shifts in my body, but also in the way I think and process things.  Whether or not it’s the hormones, or just that I have become more sensitive, more kindly, more thoughtful, I don’t know.”

At this point Sylvester opened his mouth to speak and I gave him a sharp kick under the table.

“And with all these changes has come a different view of things. A different way of looking at the world,” I said. “But – and this is the complicated bit, Sylvester, concentrate now… But the world at which I am looking is also changing.  It’s changing a lot. So, it’s like there’s two moving targets.”

“Oh, I get it,” he said, his brow knotted like an ancient oak tree’s roots clinging to the earth.

“So, as I look at the insanity going on in the world to day, I am looking at it with new eyes. It’s almost impossible to think of things the way I used to before I accepted this part of who I am – and those very same things are now all so different.  It’s very confusing. And even sometimes frightening.  I mean, there are people who would rather see a dead trans person than have a friendly trans person in their life. And they’re running the country! We used to be the good guys – and now we’re painted as a bunch of freaks!”

“That must be very difficult,” sympathised Sylvester.

“You can think of it like this.  It’s like two trains, both moving at different speeds but going in the same direction. One is going a little faster than the other, but if you’re standing on one, the other might only seem to be moving a little faster than the other, but they’re both moving at great speed.”

“Like the two Pride floats on highway one that time?” said Sylvester.

“What?” I said thinking I’d lost him.

“You remember, when we were on Highway one, and we saw that float from First Bank, and we had to race it to get a better place in the Pride procession. Remember, I raced past them and cut them off before the slip road.”

I cringed at the memory.

“I remember the girls hanging on the back of the float as you screamed past, yes.  Jenny is still having counselling over that.”

In my mind I saw Sylvester hunched over the steering wheel in the cab of the Kenworth Tractor, pulling on the horns and shouting for all the queens on the flat bed to hold on. As we raced past the other float, the driver flipping Sylvester the bird as we roared past, and taffeta, sequins and crowns flying everywhere as he pulled out and overtook the slower truck, and all just to get a better place in the Pride Parade.

“For the life of me I will never know how Alexa made the jump between the two vehicles,” I muttered. “And in those heels!”

“But we did get a better place in the Pride Parade,” said Sylvester.

“Well,” I replied, “Yes, it’s sort of like that. There’s a lot of moving parts, and at times like this it can be very confusing. And, I mean, we don’t all want to end up like Jenny, do we?”

“I suppose not,” agreed Sylvester.

But that is not the main reason I am writing to you today. Tonight I am going to an event called ‘Coronation’. This is a celebration put on by The Dogwood Monarchist Society, established in 1972 as a registered non-profit society to run the Imperial Court of Vancouver to support the LGBTQIA+ community. The DMS was recognized as the Mother Court of Canada in 1976, and is now part of over 70 courts across Canada, the United States and Mexico. Since its inceptions, the DMS has raised over $2M for deserving LGBTQ charities, and continues to thrive as an organization and as leaders within the Vancouver community. This is not only a wonderful event, Lenni (our very own) and her wife, Crem, are major drivers of the event and the organisation. You may know Lenni from our ‘Lenni And Jules’ discussions – https://fionadobson.com/tag/lenni-and-jules/.

Now, and here’s the important part, in this changing world, if you want to support an organisation that gives to deserving LGBTQ charities you should consider even a small one off donation to the DMS. I know how much good their work does and can vouch for their integrity. Donate Here – https://www.paypal.com/donate/?hosted_button_id=3LZ29C5UQ795Q

I know Jules will be down there as well, and I expect they’ll be posting pics to our support group and Whatsapp Elite Group. I am sure some will end up on our Patreon page as well. It’s happening tonight and if you jump into the Whatsapp Group you’ll see content going up as it happens.

Anyway, I have to go now and get my hair done for the event.  Have a lovely weekend!

Fiona.

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Clothes Maketh The Man – Part 75 is out!

I don’t know how long I slept. When I finally drifted back from that blissful sleep Annabel was beside me in the bed fast asleep, her hair tumbled over her gently rounded shoulders.

I watched her for a few minutes as the early light of dawn filtered in through the half drawn curtains. How perfect that shoulder was, the warm brown of her skin, the lift of her breast, half uncovered by the sheet. It seemed inconceivable that this could have been the shoulder once of a boy, or a man. No, I was looking at a woman, regardless of what incongruity may be below that perfect flowing waist and flat tummy. How meaningless the label of this or that was, when what I was witnessing was beauty. 

Does beauty demand a label, I asked myself. Male, female, young or old? No, what was before me was beauty – regardless of categorization or analysis.

READ ON – https://fionadobson.com/cmtm/clothes-maketh-the-man-part-75/

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Amanda’s got her finger stuck in the pasta maker.

As the New Year kicks into gear I am pleased to see Ali getting to grips with my garden. As you know, Ali is my Syrian gardener, and a recent immigrant to Canada. He is a diligent worker and has thrown himself into the task of managing my garden in preparation for spring.

A university professor of botany in his home country, he has come to build a new life here in our country, along with his lovely wife and two delightful daughters. Here in Canada we welcome new friends from around the world, and embrace the chance to add to the deep culture of this diverse and remarkable country.

“We don’t have an equivalent of your ‘Santa Claus’,” he recently explained while we were working at preparing the greenhouse for this years plants.

“Besides, anything flying over our airspace at low altitude stands a good chance of being shot down. And… well, reindeer meat… I think he’s well advised to respect the no-fly zone.”

“Be that as it may, Ali,” I said. “I’m most concerned about Amanda and Marjory. All through winter I’ve barely seen them.”

“Fiona, they’ve been very busy. Amanda’s been there all week. And you know what they’re like,” replied Ali.

I don’t think Ali really approves of the nature of Amanda’s relationship with Marjory. Same sex partnerships are not exactly common place in Syria, on account of people not wanting to be stoned to death in the public square.

“All the noise and fuss they make,” said Ali. “It’s very disruptive.”

“Don’t worry,” I assured him. “You’ll get used to it. Besides, it must be nice to be in love.”

“They were making an Italian dish yesterday with the left over turkey,” he mused, while cleaning one of the planting beds in the greenhouse.

“That sounds lovely. One of the things I enjoy about home cooking is getting creative with all those meals using left overs. I had turkey curry yesterday, myself.”

“If I over heard it correctly, Amanda got her finger stuck in the pasta maker. It was quite disturbing,” said Ali.

“Oh,” I said surprised. “I thought Marjory made the pasta.”

“Yes,” replied Ali. “She does.”

But that’s not the main reason I am writing to you today, as we go into what I think we are all hoping is a more hopeful year than last. I understand many of us are finding it harder to dress during the lockdowns that we must inevitably endure. I also realise that this increases the stress for all of us, and I want to make a suggestion that I find has helped many of my members.

While it would be wonderful to be able to dress everyday, all day, many of my members are simply unable to do this. When it is impossible to dress, for whatever reason, there’s still the middle ground, of becoming more androgynous. This is a way to start shifting what you wear to something somewhat more feminine, though without being entirely crossdressed. If you get creative you’ll find ways to do this, and enjoy that middle ground in the gender spectrum.

It could be as simple as shifting the colors you wear. Pastel colors and moving away from hard contrast color patterns is somewhat more feminine and gentle. Equally, going for the lambswool sweater and softer fabrics is always more enjoyable.

For others it will be engaging a more feminine clothing style, without crossing the line. Nice jeans can bring out the shape of your legs, and if all you need to do is add heels to shift over the line, then you’re always just moments from being able to express yourself in a gently feminine manner. Sometimes the only difference between dressing straight or crossdressed is the presence of eye makeup.

It’s always important to remember though, the clothing is really only the aesthetic. How you feel and how you think will always be more important. Check out my Patreon for more ideas.

Be sure to enjoy the video below.

Fiona

Poison! Part 1.

The soft sensation of nylon against my skin is almost the perfect form of foreplay. Pulling on the nylon stockings, and smoothing them up my leg, unhurried and luxuriously before a date is always enough to make me wet.

Perhaps it’s a response to my desire for something to happen, or maybe it’s just a learned response. After all, most times I do go out dressed in this manner I get what I’m looking for, so it’s only a matter of time before my body, hungry for the lecherous and desperate touch of a lover, is served to my satisfaction. You’ll note that I said ‘my satisfaction’. I point this out as I do like to play a little game.

It’s been about five years now that I’ve followed a rather particular dating practice.  I usually use one of the more popular apps, Tinder or some such, and there I will select a – now what should I call them – a project. Yes. I select a project. You know if you go to some of the apps you can even find me. Of course, I’m not going to make that too easy for you, as I really don’t want to give away all my secrets.

Continue reading “Poison! Part 1.”

My father thought he had three boys.

As I think you know, I am a fairly modest individual. I don’t take any pleasure in blowing my own trumpet. I need hardly tell you that on mentioning that to Sylvester he trotted out some trite comment. He really can be quite coarse at times.

With the small amount of celebrity that I have garnered over the years there are naturally moments when I am recognised and photographed, when out in public. I don’t resent this.  I accept that it comes with the territory of being a transgendered account executive at Canada’s seventeenth most awarded advertising company. Apparently, with great power comes great responsibility, to quote Maya Angelou.

It was during the Pride Parade in Vancouver recently that a flock of paparazzi recognized me and descended upon me flashes flashing and video videoing. I must say, in the centre of this light storm I found myself very lightheaded. Perhaps it was the hot weather, or maybe the noise of the parade, but quite suddenly I felt very feint. A moment later the world seemed to tilt on its axis and I was suddenly falling, falling, falling.

 When I opened my eyes I found myself in an unfamiliar place. I was surrounded by mist, and there seemed to be no horizon. There was a soft white light, no walls and no floor. A gentle fog rolled about the place, a little like when Sylvester had that smoke machine in the car and couldn’t turn it off and we got pulled over by the police. Sorry, a story for another day.

From out of this monochromatic landscape a figure emerged with a long white beard and a scroll. Now, I know what you’re thinking. They always have a scroll, right? Why no Ipad? I know – I’ve asked the very same question.

Continue reading “My father thought he had three boys.”