10 Questions You Always Wanted To Ask A Gender Fluid Person.

It’s Playtime With Fiona

Join me for another episode of Playtime with Fiona. I can hardly believe how creative Sylvester has become.

Here’s a handy crossdressing tip. Sports bras often come with a pocket for inserts. Even when they don’t they are a useful thing to have, as you can increase your feminine shape very subtly, giving yourself a small but apparent breast mass.

This not only looks great, it helps you feel very feminine. If you don’t have one or two, maybe this is a great time to consider buying one. Remember to choose sizing conservatively. They are usually made of a somewhat stretchy material, but avoid making the mistake of buying something too small. It will never be comfortable, and won’t feel so good.



Jen’s Guide To Cuckolding.

Jen is a hardworking librarian at the local library. She’s a popular lady in the community and likes to get out and about. However, her weekends are a whole other story.

Get the full story HERE.


Many times it has been said that Sylvester is the living proof that homo sapiens interbred with their Neanderthal cousins. One can’t look into that low forehead, that heavy brow, or those dark eyes without wondering if you should give him a bannana.

Indeed, if his brooding look of general confusion – not an uncommon sight – leaves one thinking there’s not much going on inside that head, it is his gait that seals the deal. In fact, the way we walk says so much about us. I’m including Lisa’s video for that reason. She really is very good.

It is fair to say Sylvester’s chosen style of walking is more of a lurch than a stride. It has been said that he moves with all the grace of a horse falling out of a tree.

He really is the limit at times. I took him as a ‘plus one’ to a work function last week, and can only describe it as a disaster. I am usually more careful about who I take to work functions.

I should also say that there are thankfully many fewer work events that involve game playing, alcohol and a senior partner of the advertising company I work for playfully bouncing me on his knee at 11.30 pm. It was however to one such event that I found myself invited to and attending earlier this week.

Now, I’ve never much liked the game Charades. This is the one where you are given the name of a film, a book or a play, and you have to mime the title to the other players until one guesses what it is. I was paired up with Sylvester, which was just as well, all things considered. We play in teams of two because some of the younger staff need things explained to them. Like what a book is.

I revealed to Sylvester what we had to mime, a he immediately burst into a display I can only describe as being distasteful. The gyrating hips, the thrusting motions, and that zombie like gait. It shocked not only me, but also most of the senior staff. I think the head of HR, Brenda, is still quite damaged by the incident.

I won’t go into the details. Needless to say being unfamiliar with the book, Sylvester thought I said ‘Angela’s Rashes’ instead of ‘Angela’s Ashes’. An easy mistake to make, i suppose. It was most disturbing.

By the way, you can learn more about my workplace by reading THE CROSSDRESSER’S WORKPLACE PHRASEBOOK – which is part of the Premium Program.

Have a lovely week.



By the way I am migrating from Twitter. The place has become just too toxic. My Twitter will go dark soon. I can be found now at Mastadon here – @FionaDobson@mastodon.online

The magnificence of dreams.

I stepped out of the warm stream of the shower knowing Sebastian and Sylvester were downstairs waiting for me in the breakfast room. After pulling on some panties, a robe and my pink fluffy slippers I hurried down the stairs.

Sebastian and Sylvester were at the table. I’d completed a particularly rigorous dawn yoga session with Sebastian. If my hips were any more open you could have driven a train up there. As luck would have it Sylvester had offered to make us breakfast. While usually a coarse oaf, Sylvester has the capacity to be quite sweet at times.

As I glided into the kitchen Sylvester was serving up a delightful grilled breakfast, the sausages sizzling fresh off the skillet. A good start to the day is a lot easier with a breakfast like this. And breakfast is really the most important meal of the day. The bacon was glistening with flavor and the tomatoes came from Ali’s own garden. Quite lovely.

“It’s the damndest thing,” I said staring at the plate.

Sylvester looked at my plate and said “what’s wrong with it?”

“No, not the food. It’s just I had the weirdest dream last night.”

Sebastian asked, “What did you dream?”

I closed my eyes and tried to remember how it all went.

“There were a few of us downtown. And there was this guy who had died.”

“Who was he?” asked Sylvester.

“I don’t know. It’s not important. Just some stiff,” I replied.

“Anyway they wouldn’t let him in the graveyard because the church said they didn’t have room. But everyone knew it was because he was queer. So, there was this drag queen. She was lovely. Let’s call her ‘Carlotta’.., and I. And we stole the body and buried her up in the church yard anyway.”

“You know they don’t let you do that,” said Sylvester.

“It was a dream,” I protested. “And we went up there and buried this guy. And then we did other stuff. Loads of stuff… And I had this lovely long velvet riding dress,  like in that English serial.  And Carlotta had these sequins on her pants and a gold cowboy hat and these huge guns with pearl inlays and a smoked blue gunmetal finish. A pair of 44s. Matching nails. Did I say we were on horses?”

“I know all about Carlotta’s 44s. How many of you were there,” asked Sylvester, a canny look in his eye.

“I believe it was seven. Seven trannies and drag queens. And one was bald. I’m not quite sure what her deal was. Yes, that sounds about right. You have no idea how much glitter that is.” I replied.

“Yes, you just dreamed The Magnificent Seven. That’s one of the best movies ever made,” said Sylvester.

“I thought it was a fantasy about masculinity and white privilege wrapped up in a self righteous superior message, all avoiding the whole gun thing, and how it’s a penis substitute and actually they’d all rather be playing with their wieners. Except Yul Brynner. No, If he was coming after me with that huge weapon of his. Well, let’s just say I wouldn’t be running away all that fast.” I replied. “Can you imagine,” I said my thoughts drifting off. “…falling, and Yul leaning over you and reaching down and pulling you to your feet, and grabbing a great handful of ass and ripping….” My voice tailed off.  Sometimes I do forget not to speak my thoughts.

I continued, “But, yes, still one of the best movies ever made.”

Bringing a note of levity to the conversation Sebastian chimed in, “They’re all gone now…”

And what a time it would be to have a magnificent seven. With trans rights, and democracy itself on the ropes, we see so many hard won advances in decline. Things will turn around again soon. And in the meantime I think we have to support our trans sisters, regardless of what stage they are at, wherever we find them. Remember, you’re not alone. There are many of us here.

Enjoy the video clip below.



Are you ready for Halloween?

It’s soon going to be Halloween, and Auntie Kittie is suggesting all her girls embrace their powers this year by dressing as Wonder Woman. You can find your costume right here: https://amzn.to/3elizio

If you love cheesy special effects and great outfits, check the clip below. It might inspire you to get ready for a wonderful Halloween. Now, who are you going to ask to do your makeup?

Just to make it interesting you can win a $100 membership to our Seahorse group for one year by sending your Halloween pics in to fdobson@zoho.com – Auntie will make a pile of your emails and then pull one member off at random from that pile of emails (yes, she actually prints them!) to select a winner. Perhaps it’s just a selfie of you in costume, or maybe it’s a photo essay of your friends dressing you up and putting the right makeup on… send it in and we will post all we reasonably can!

Your pics will appear on the site, so be sure you’re ok with me using them. No, you don’t need to be a member already to enter this competition.

Don’t forget there’s plenty of Halloween content on the site. You can find some HERE. Oh, and by the way, the results are in for this week’s ‘Shit Of The Week‘ Award.



What Superhero are you for Halloween?

“So, wait a minute,” I said, scratching my head. “You want me to dress up as a sexy cowboy who is actually a woman impersonating a man?”

“Yes!” said Sylvester enthusiastically.

“Sylvester, you have met me, haven’t you? Do you know nothing of my journey?”

Like a typical man Sylvester then tried to claim that this was ok, because it’s all about inclusivity and a woman doing a man’s job. And how if I was a man I would know this. And then he went quiet and realised he was speaking aloud.

Sometimes there’s so much wrong with what comes out of the coarse oick’s mouths I just don’t know where to begin.

I looked at the advertisement again, and said, “You can really be quite coarse at times, Sylvester.”

And then quietly added, “I could just bite that ass though.”

You can buy the outfit the pervert had in mind here – https://amzn.to/3CtNh0S

I handed Sylvester a large bowl of Brazil nuts, and some pliers.

“Make yourself useful, won’t you?” I said. “I need you to shell these, with those big strong manly hands of yours.”

Sylvester sat at the kitchen table and started removing the shells of the beautiful nuts.

It was at that very moment that Auntie Kittie burst through the kitchen door, handkerchief in hands touching it to her eyes.

“What on earth’s the matter, dear,” I asked as I helped her to a chair. I expected it would be something to do with her naughty nephews and nieces, but decided I’d hear her out.

“It’s those beastly Russians, doing all this heavy shelling near Kiev. The children, Fiona. The children!”

“I know,” I said. “You just sit there next to Sylvester. He’s doing some heavy shelling of his own, as it happens.”

Auntie Kittie looked confused and sat beside Sylvester while I went to find her a glass of something to strengthen her resolve.

“What are we to do?” Sobbed Auntie. “I feel so helpless. Surely, Fiona, you must have some idea?”

“Of coarse, I have, Kittie. You don’t think we’d have this happen and not have something in mind. If you use THIS LINK you can make a donation to Unicef’s fund for the protection of the children of Ukraine.

With 5.5 million children at risk donating directly to this targeted fund is the most effective way to see your money makes a difference on the ground in Ukraine quickly. I can say this having worked for Unicef in one of their emergency operations for 2 years. They really do incredible work.

I believe there’s an empathetic side of us, in this particular corner of the world, that understands the terrible nature of suffering some people are exposed to, and through no fault of their own. And I believe we must all do what we can to help. You really can be a hero this Halloween.

If you’re able to help please do so. I will not be alone in thanking you for your kindness.



I’m keeping abreast of things.

“Tits like coconuts,” said Ali as I pondered his idea. He was, of course, quite correct. If we wanted to attract more wildlife to the garden we should hang out something to induce them to come. Apparently, the blue tit loves to play with a coconut hung from a branch.

“Well, then,” I said. “You’d better get out there and buy some coconuts.”

It’s so good to have someone looking after my garden who knows what they are doing.  And that brings me to my very next point. For all my lovely American members I want to remind you that soon it will be time to vote once more, and it’s very important for our trans sisters to try to stem the gradual erosion of trans rights that we’ve seen in so many Republican states.  Please be sure you are registered and familiarise yourself with the issues at stake. With gerrymandering and the assaults on voting rights we’ve witnessed in the last few months it’s more important than ever to make sure your vote counts. Plan ahead so that you can be sure to get your vote in, either by advanced voting where it’s available, or by showing up on the day.

Don’t forget you can win a $100 membership to our Seahorse group for one year by sending your Halloween pics in to fdobson@zoho.com – Auntie Kittie will make a pile of your emails and then pull one member off at random from that pile of emails (yes, she actually prints them!) to select a winner. Perhaps it’s just a selfie of you in costume, or maybe it’s a photo essay of your friends dressing you up and putting the right makeup on… send it in and we will post all we reasonably can! Who knows, you may be the one that Auntie Kittie pulls off!

Your pics will appear on the site, so be sure you’re ok with me using them. No, you don’t need to be a member already to enter this competition.

Enjoy the story below as you get ready for Halloween, and don’t forget there’s plenty of Halloween content on the site. You can find some HERE. Oh, and by the way, the results are in for this week’s ‘Shit Of The Week‘ Award.


Can you help Auntie Kittie with a special job?

As you probably know Auntie Kittie does like to keep a close hand on her nieces and nephews. And what a naughty little group they are. Always up to some mischief or another.

As you likely know, Auntie Kittie splits her time between here in Huckleberry Close, and travelling to South Africa, where she is a school governor. What a responsibility it is, forming those malleable young minds into sensible adults.

And of course, now and then someone comes along that Auntie needs to discipline and remind them that they can be so much more than their poor behavior might suggest. For that very reason she does apply her own very special brand of discipline.

She does so love to share her diary with all of my Good Gurls. Think of it as her setting a good example for you to follow.

So many sissies need Auntie’s guidance. Perhaps you feel the need too. And Auntie is always keen to hear from new ‘nephews’. All you need to do to help her out is explore some of her posts here and see what tweaks your interest. If something does, then be sure to join my Good Gurls, and get special access to Auntie Kittie’s diary.


There’s never a dull moment in the advertising business.

As you likely know, I work for a well known advertising agency in an active office in this delightful city. It is often said that for each job in some industries, several other people are supported. So, for example while a car plant may employ 4,000 people a further 6,000 jobs are created servicing the 4,000 people employed with things like transport, employment services and catering. In much the same way, my work supports not just myself, but also Sylvester my mechanic, Sebastian my personal trainer, Ali my gardener, young Max who helps with technology on my blog and several other assorted hangers on and peripheral individuals.  

I was talking on this very subject with Bernard, my photographer, when we were out on agency business just the other day. Ali, who so lovingly tends my garden, spends more time there than I ever do. Instead, while he enjoys my delightful champaign colored roses in my garden I am out driving with Bernard on a task for the advertising agency. And I’m paying Ali! It all seems rather obtuse. That said, I do love Ali, and his daughters are sweetness itself. They arrived in Canada just a couple of years ago, refugees from the war in Syria.

Continue reading “There’s never a dull moment in the advertising business.”