Category: Sylvester

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A little something to help you through the daily grind.

“You know,” I said to Sylvester as he got ready with some lube, “I feel I need to give my gurls a little bit of a hand from time to time.”

Sylvester looked up at me, applying the shiny liquid to his shaft.

“You’re so thoughtful, Fiona.”

You will remember that Sylvester is a mechanic. He’s restoring an old engine at present. He knows the value of making sure all the parts are well lubricated.

“Are you sure it’s going to fit,” I asked as he slid the shaft into a tight fitting sleeve.

“You’d be amazed what a good amount of lubrication can do,” he said concentrating on the job in hand.

The shaft slid home with a satisfying metallic sigh.

“Goodness,” I said with a slight gasp. “You’re really very good at this.”

“Yes,” he said with a look of studied concentration. “Lubrication is the key to so many things.”

“You know you’re right!” I replied. “I just feel I want to help my members feel a sense of satisfaction. So many of them put up with so much.”

It was as I thought about this that I decided to post a few pictures that might elevate your mood. You know, if you’re on this site then I am like a sister to you. And any good sister would be prepared to bend over backwards to help you feel good about yourself.

Do you think I should bend over backwards for you? Well, register and see what I have as you slip inside the website. You know the deeper and deeper you go into it the more satisfying it can be. Come on. Register here, and go really deep. Just the way I like it.

🙂

Fiona

PS – be sure to sign up for one of my programs to experience the deep satisfaction we both crave.

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Poor Rainbow! I can’t think what got into her last night.

Rainbow sat clutching her gentle brow at my kitchen table, pale and effete as ever. That girl could well be a vampire.

“No, Rainbow. I don’t think anyone rufied your kombucha,” I said.  “I think you drank half a bottle of gin on your own. And that’s what it does.”

“But, my head,” she moaned.

Sylvester shifted awkwardly. Like most men, the delivery of unearned sympathy is something he struggles with. Instead he sensibly kept his mouth shut.

“You need a nice cleanse,” I said as I fried an egg in a heavy iron frying pan. “A sauna, perhaps and then a seaweed wrap.”

“Sushi?” she said, turning a little green.

“No, a seaweed wrap, where they wrap your body into the healing energy of seaweed. It’s lovely. I had one with Sebastian last week at the spa.”

“You realise I am basically an unemployed student?” retorted Rainbow.

“Well, I’m just saying, with all that yoga and healthy living…” I adopted my most forgiving manner.

“Are you saying I can’t go out and drink till I can’t feel my face from time to time?” she replied.

Rainbow seemed to be a little tense, as well as being in the midst of a severe hangover.

“Where on earth were you?” asked Sylvester.

“Some of the girls from the yoga studio and I went out to celebrate at Trannie Annies,” replied Rainbow.

“They don’t let me in that place anymore,” grumbled Sylvester.

“Shut up, Sylvester,” I said. “May I ask what you were celebrating last night, Rainbow. And, I mean, darling… was it really worth it?” I asked in an attempt to mollify her.

There was a long sigh, and then as I handed a high electrolyte orange drink to Rainbow she shared her latest news.

“and then … Yadayadayada, so now I realise I’m poly,” she concluded.

I stared at her.

I pride myself in being a crossdresser of taste and style, even if I do hang around with coarse oafs like Sylvester from time to time, but this was shocking news to me.

“Really,” I said stifling my bewildered emotions. “You’re into polyester?”

I couldn’t sanction such perversion.

“Don’t be ridiculous,” said Sylvester. “It means she’s got a thing for parrots.”

“You two are the limit,” said the poor suffering girl as I placed a perfectly fried egg on wholegrain toast before her.

“Really, Rainbow, darling, I can prepare a nice cleanse for you. An elixir of dandelion root, sage, kayle and Labrador tea leaves. I think of it as a very healthy cleanse.”

Sylvester piped up, “Sort of an ‘ethnic cleanse’. You’ll feel like an entirely new person. I always say “When you feel like the bottoms fallen out of your world, Fiona can make a cleanse that will make the world fall out of…”

“Sylvester, belt up!” I interjected.

Sylvester really can be quite coarse you know. I sometimes wonder why I let him in. Still he does like to come and join me for breakfast after driving the Zamboni to prepare the ice for our hockey players for their early morning practice.

Now, I’m sure you know this, but if you want to drill down and learn more about some of my people you’ll see that the first mention of them is generally highlighted and a hot link. Through the wonders of technology, if you click on that you’ll get a list of all the stories in which they feature. So you can drill down on any of the people and get more of their story. After 7 years of writing you’ll find the well is indeed quite deep. It can keep you uselessly employed for hours!

Have a wonderful day.

🙂

Fiona

PS. I recently rebuilt my Patreon presence. They’d kicked me off before but have let me back now on the condition that I keep my panties pulled up. If you’re enjoying these messages be sure to join me at any level on Patreon to build up my presence there. I include some fun content there. I am always grateful to my members. xxx

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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.

😊

Fiona

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I’m getting off.

I had just got off the phone with Sylvester. I called him because, being a quarter Italian, I thought he’d be able to tell me which was better, the Heinz ravioli or the Chef Boyardee one.

Really, it’s so easy to yank some people’s chain. Don’t worry, I only do it because I love him!

It’s all that, “Mamma used to make pasta by hand,” and “It’s not real cheese if it’s not from Italy.”

Honestly, they think they are the only people who know anything about culinary expertise. Why, I was making a lemming meringue pie just this week, but it fell of the table. Make of that what you will.

All that said I can’t deny that the Italians really do know how to seduce you through your mouth. The sensuality of linguine and the rugged honesty of meat balls, I mean really. What kind of pervert do you have to be not to love that?

All of which has nothing to do with the real reason I’m writing to you.  Part 61 of Clothes Maketh The Man is out. So many people have been waiting with baited breath to see what disaster is about to befall poor Andy next. All I can tell you is, ‘you really wouldn’t want to be Andy!’.

Have a lovely week.

🙂

Fiona.

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You are my Valentine.

What a wonderful day to remember our lovers and our past lovers. On a lovely day like this such thoughts are top of mind.

I have always taken a keen interest in medical and biological research. For example, when in 2010 UCLA researchers announced that they had proof that Neanderthals mated with homo sapiens it came as no surprise to me. But then it wouldn’t. As anyone who has met Sylvester, my mechanic, would realise, the evidence has always been there right before our eyes. 

But that’s not the main reason I’m writing today. It’s Valentine’s Day, and the time we celebrate our relationships. Max, my neighbors son, attempted to deliver a Valentine card secretly, but was picked up on my security cameras. He has no idea I know it was from him. Poor boy is only a breath over twenty years old. I’ll probably have some fun with that.

Sadly my wife is travelling at present. However, although I may have to battle the sadness of solitude and isolation, I wouldn’t want my members to suffer. With this in mind you might be interested in checking out My Little Black Book. It’s a pretty cool system, in which you contact three people a day until you build up a network of crossdressing friends and admirers. Anyway, you can read all about it here. It’s one of the benefits in my Unicorn Tier on Patreon, though you can by it as a stand alone product for as little as $2.95 if you wish.

So, sign up for My Little Black Book today and you can be sure you’ll not die alone, as Sylvester put it. Quite a few members have formed long and meaningful relationships in My Little Black Book. If you’d like to connect with other crossdressers it’s a great way to do so.

Have a lovely Valentine’s Day.

😊

Fiona 

– http://FionaDobson.com

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Let’s help Sylvester get it up.

As you likely know, I am a very busy gurl.  I like to involve myself in so many activities and hobbies, from pitching a tent to kite flying – I do love to get it up in a high wind – to support all my athletic friends, of course.

Recently my friend Sylvester was bemoaning the fact I am so busy.

“I have so much on,” I said. “So many appointments.”

“But surely you could drop them, just for me.” That’s not the first time I’ve heard that line spill from his lips, I assure you.

Sylvester is being a little insistent as he wants me to be one of his supporters in the up coming local Highland Games and Scottish Festival. I am unsure if you’ve heard of this, but I will explain it to you. A number of events such as the Caber Toss and Hammer Throw are offered and competitors test their skills. Sylvester has done quite well over the years.

He’s been asking me to come down and help polish his caber up for practice a number of times recently. As I work away at the great shaft, polishing for all I am worth I often find myself humming the little song of the highlands my grandmother used to sing.

“Come where the hands are clapping
Come where the toes are tapping
Come where the jocks are strapping
Down in the glen.

Land of inclement weather
Land of the prickly heather
So keep your knees together
Scotland the brave!”

Well, I thought, if I’m going to support Sylvester in his highland fling I have to find something suitable to wear.  My first thought was a kilt, but as every gurl knows, you just can’t show up in something that everyone else is wearing. That’s when I turned to my friends at The Drag Queen Closet. I have to tell you about them, because they are so good at what they do. Firstly, their clothes are properly sized. I know that when I order the XL size it will fit me like a glove – and I don’t mean a floppy old gardening glove. I mean a sheer perfect latex sleeve that fits perfectly. Second I know it will be delivered discretely and swiftly. And finally, it will be a good quality Item I can be proud to be seen in.

Find it HERE.

Naturally they had exactly what I was looking for. So much more fun than a simple kilt, a little steampunky and at the same time elegant. The quality of this type of garment is far greater than you generally expect of CD clothes. I know it will last and I can feel good about wearing this lovely design. When it arrived a few days ago I was thrilled and I have struggled not to wear it every time I go out, because it’s meant to be a surprise for Sylvester when he’s at the competition. After all I want him to do his very best tossing his caber and get a high score.  Being there to be supportive and get it up – among the leaders – will mean the world to him.

You should seriously think about using The Drag Queen Closet for your supplies, and sooner or later you’ll be getting it up too!

Have a wonderful week,

Fiona

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Bounce your way to freedom.

I walked into Sylvester’s slightly messy workshop along with Ali, who had given me a ride down to the auto repair shop in his Smart Car. I must say it’s a tight squeeze, even though we’re neither of us very large.

I wore a light cotton summer dress and some deck shoes. I offset the look with a necklace of white oversized beads and a matching bangle.

You probably know that Sylvester is something of an inventor. He’s always got one new thing on the go or another. That morning I glanced around at the busy workspace at shafts of metal, Sylvester feverishly fitting sleeves and flanges together, and what looked surprisingly like a disassembled pogo stick on the workbench.

“Dare I ask,” I said.

“It’s a device that will revolutionize the life of anyone needing a prosthetic leg,” replied Sylvester without looking up from what he was doing. “It combines the length of stride of a tall man, with the spring action of a pogo stick. It will make speed walking easier,” he paused and then added uncertainly, “and more exciting.”

“Are you quite sure this is a good idea?” I asked looking at the dubious collection of parts.

Ali looked about the place and then said, “I think I know this thing. It’s a monobouncyunipod.”

Sylvester looked up at him in surprise and said, “I had no idea you were versed in the ways of advanced neo-prosthetic engineering.” He seemed to suddenly have a new respect for Ali, my Syrian gardener.

“What,” said Ali, a little affronted. “You think we didn’t have pogo sticks in Syria before the war? We had many things. We had wonderful things,” he continued, his eyes glazing over as he looked into the distance. 

Ali continued, “My next door neighbour, Sara, had one. Bounced around on it all day.” He smiled to himself and then continued, “Her sister hurt herself and had to have part of her nose stitched back on.”

“Well, I don’t think you can call it a ‘Monobouncyunipod’. It doesn’t exactly trip off the tongue. No one will buy it,” I said.

Sylvester looked up from the workbench.

“No, you’re right,” he replied thoughtfully. “I shall call it ‘The Unitard’!”

“Oh, yes,” I said a little sardonically. “I can see it now. ‘Bounce your way to one-legged freedom with The Unitard!’. What could possibly go wrong?”

And that brings me to this weeks exciting suggestions to help you crossdressing.  The Unitard is a vastly under rated piece of clothing. And yet, for a crossdresser it’s surprisingly adaptable.

Ideally you want something that covers the arms and legs, so any unshaved areas become a non-issue. Additionally it should be easy to wear, wash and combine with other clothes. Score, score and score.

A nice unitard, combined with a plain wrap around skirt is simple and striking. Whether you just want to lounge about or be more active, check out the unitards on my Pinterest and think about dialling them into your crossdressing wardrobe.

I am traveling a lot at the moment, so expect to see me popping up at unusual hours on the site.

I am working on some special content on my Patreon at present. There’s a level there called ‘Behind The Scenes With Fiona‘. This is a personal set of posts that reflect some of the unusual things I deal with on a day to day basis. It will be of interest to others who are also in a gender fluid place and dealing with the day to day challenges of life. Be sure to join my Patreon to enjoy some special exclusive content.  It will start appearing toward the end of this week. I’d also love to see you join my Patreon as I am trying to build my numbers up there.

Have a wonderful week,

😊

Fiona

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Do you ever feel like playing with yourself?

Hi,

Of all the busy bees in my life these days chief among them is my good friend and mechanic, Sylvester. I came into the living room just yesterday to find him on the floor with Sebastian, my personal trainer, saying “Colonel Mustard, in the library with a ten-inch dildo.”

“I beg your pardon,” I said a little shocked.

“Oh hello,” said Sylvester. “We’re playing Adult Clue (or Cludo if you are from The United Kingdom). It’s something I’ve adapted from the board game.”

Sylvester can be quite a disturbing individual, and he really can be quite coarse at times.

“Well,” I said, trying to be encouraging although I felt a little awkward, “I’m glad to see you’re not letting your God given talents go to waste, Sylvester.”

After a moment’s thought I added, “Perhaps you could think up some way to murder a new character – you could call her, oh, I don’t know… ‘Amanda’. Death by impaling, in the neighbors house, by the crossdresser.”

For those of you who don’t know, Amanda is my wife’s childhood friend, who has started a relationship with my next door neighbour, Marjory. This is a source of some annoyance, particularly as my wife is travelling at present.

I should tell you I enjoy competitive games enormously. I also play some role playing games. So many times I feel like I’m getting ahead and suddenly someone’s coming up behind me and a breathless struggle ensues. It’s all very exciting. Perhaps you know the feeling. Sometimes I get so excited, I just don’t know what comes over me! I guess it’s the cut and thrust – mostly the thrust – of putting oneself up against a fellow player.

I should also say that this week one of my friends who is a regular player got on a plane to work in New York for a couple of weeks, leaving me with no alternative but to play with myself.

That, however, is not the main reason I’m writing to you. I thought I’d write and tell you about the delightful Mollie Blake. She’s a talented writer who has recently had a piece featured on my website, and we’re expecting to see some interesting new episodes from soon. If you’ve not already read “The Dating Game“, this weekend is a great time to do so. 

I should also draw special attention to Katia Thornwood’s writing, which is mostly in my Seahorse level which has been growing into a favorite among my members. Slipping into bed, and putting Katia on to read as you fall asleep is one sure way to end the night on a high note.  Katia’s style is quite unique, and if you enjoy her rather strange view of the world.

For the many members who are asking about the Clothes Maketh The Man chapter list it can be found HERE. Well, you can see that the office here has been pretty busy bringing you the best of all things to do with Crossdressing. Have a wonderful week.

😊

Fiona

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I’m not feeling myself this morning!

Hi,

So, today I’m writing to talk about how to find great ideas to help you crossdress. We all need a little inspiration and time to do some planning from time to time. One of the simplest and most fun ways to spend a pleasant evening with a glass of wine and a pair of nylons, is to browse Pinterest looking for looks to emulate.

Many of you have heard me suggesting you do something other than looking at lingerie as your only crossdressing option.  Especially if you’re over 45, trying to look like a teenage bimbo is a goal you’re unlikely to reach. We’re not all as naturally lovely as Nikki Buxton, who I was very happy to chat with a while ago. As I’ve said before, a pig in a lingerie is still a pig. Not a phrase Amanda would appreciate. Better to aim for an attainable goal.

Personally I love steampunk styles. It speaks of fun, adventure, culture and sophistication. Check out my Pinterest for what turns my crank!

Looking like a great 45 year old woman is a viable option for a 45 year old crossdresser. Anyway, I have literally just started a Pinterest site where I post a few of my own ideas for dressing. If you follow me you may get to post to the Members Ideas Board. These may inspire you, or you may browse other looks and style. Either way, jump in there and look for a style that works for you. It’s fun and once you have a bit of an idea, you can go put and shop the entire outfit.

Once you’ve done that, crank up the volume and listen to today’s music video (below) and have a dance around the living room. What better way is there to indulge your feminine side?

If you’re in the north, I hope you are enjoying this lovely snowy weather. If not, have a great week anyway.

😊

Fiona
ZZ Top - Sharp Dressed Man (OFFICIAL MUSIC VIDEO)
It’s always wise to dress for success!
Chastity Devices – Breast Forms – Wigs – Corsets
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Back to the rain.

I am back from Mexico. If you want more details, I have three words for you; ‘Behind The Scenes’. Yes, you can learn the details if you’re a member of my ‘Behind the Scenes’ tier on Patreon.

So, with my freshly tanned shoulders wrapped up and standing beneath an umbrella held by Sylvester in one of his ham sized paws, you find me standing beside something that’s appeared in my back garden.

“But what is it,” I said to Ali, my gardener.

“Your Christmas present, and it’s beautiful,” he replied. “It’s a sundial. My people have been using sundials to tell the time for 3000 years.”

“Your people?” I said.

“Gardeners?” asked Sylvester, looking confused.

“Those of us who come from the middle east,” replied Ali. “Persians, Syrians. Us lot.”

I sometimes feel that Ali’s skills are wasted. He used to be a botany professor at Damascus University. And now he tends my garden. He seems happy though. Talking to Sylvester is a little like petting a monkey, for Ali.

“Thank you, Ali,” I said. “That’s a very kind thought.”

I looked skyward and I could see Ali was reading my mind.  I’ve just got back from a land of apparently endless sunshine, but the sky over Vancouver between the months of October to April resembles nothing so much as being inside Tupperware.

“I don’t think I’m getting rid of the kitchen clock, at least not before spring,” I said. “But it is beautiful. You’re very kind.”

“Three thousand years, you’ve been using these?” said Sylvester.

“We should probably ask Amanda how it works,” I said. “She probably remembers the product launch party.”

At this Sylvester gave me a sour look.

Ali looked at the cloud covered sky and then examined the numbers around it’s base, and then said “I think it was 2.30, in September…”

I’m sure that when the sun comes out it will be a lovely centre piece to the East garden. Ali is so thoughtful. And I’m not one to look a gift camel in the mouth.

🙂

Fiona

We now offer remote counseling and hypnotherapy for people struggling with gender issues. Learn more HERE.

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I woke up today to a terrific banging.

I awoke this morning to a terrific banging. Now, I know what you’re thinking, but it wasn’t like that at all.


I pulled on a lovely apricot silk gown, and fluffy slippers, and hurried down to the front door, where I was confronted by Sylvester and Sebastian chatting away, framed by snow in the doorway.

“I had a huge curry, last night,” said Sylvester, “and I woke up to find we’d had a terrific dump!”

“Good morning, Sylvester,” I said as the two of them stood on my snowy doorstep. “I assume you’re talking about this heavy snowfall.”

“It’s about 9 inches and I couldn’t get up the drive at all.”

“Can we use your rear entrance, Fiona?” said Sebastian.  If I had a nickel for everytime…

“Why don’t you boys slip around the back of the house. Ali’s very kindly cleared the lane. You should be able to park there without difficulty,” I said.

And with that the two boys disappeared and left me to put on the hot chocolate, and warm some croissants. My friends are joining me for breakfast today as we’re working on some new ideas for the premium program. If you’re a member of this wonderful program you’ll know how much fun we have with it. If you’re not, then think about jumping in!

Have a lovely day.

🙂

Fiona

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Are you ready for your massage ;) ?

Are you ready for your massage 😉

Hi,

It’s the night before Christmas eve here in Huckleberry Close, and I have had the most extraordinary text message from Bernard. As you may know, Bernard’s health has not been good recently. Between being tazered and shot in the chest with a carrot, he’s had quite a year.

With this in mind he traveled to England for Christmas, where he has some family, and checked himself into a rather eccentric sounding health farm near something called ‘Newmarket’. He’s being treated at “The Devil’s Dyke Centre for Alternative Health.” This immediately had me thinking of a friend of mine who recently divorced her lesbian wife. As you might have guessed the divorce is not going well.

Bernard’s text read: “Hope all is well. Love to the crew. Just waiting for the nurse to give me my evening massage.   😉 “

Now, I don’t mean to be pedantic, but that smiley winkey face at the conclusion of the message did give me pause for thought. At the time Sylvester, Ali and I were enjoying a few glasses of eggnog while I modeled a new gown I recently treated myself to, and Ali showed us a traditional arab jalabiyyah. Needless to say, Sylvester wore his Carhartt pants, and frankly I think Ali and I looked considerably more presentable than our swarthy friend.

Amanda had joined us, ‘popping in’ as she does, not unlike a visit from the plague. We all sat around the log fire in my living room and enjoyed the winter evening.

Making conversation, Sylvester said, “I see Bernard’s started using emoji’s. I don’t think he’s quite got the hang of it yet.”

“I couldn’t agree more,” I said, showing them both the recent text. “I mean, really. What is one to make of that?”

The eggnog was fortified with substantial amounts of brandy, which neutralizes the sweetness a little, though does not reduce the calories, to Amanda’s disappointment. I’ve been making this recipe for years, and it was given to me by my grandmother.

Ali passed on the eggnog, but Amanda drank it deeply. I could tell she’d had more than is wise from her slightly slurred speech.

“Where on earth do you get this,” asked Amanda looking at her glass. “It’s so smooth!”

“Oh,” I replied modestly, “it’s just something I knocked up.”

“Rather like your first wife,” I heard her mutter under her breath.

Just then Sylvester got to his feet to refill his glass, nudged the table and Amanda’s glass toppled into her lap covering her with eggnog. She yelped like a… Well, like a startled pig, and got to her feet.

“Oh, I’m so sorry,” Sylvester gushed.

“Don’t worry, Amanda. I’ll find you something.” I said and trotted off upstairs to get her a skirt. Perhaps I could find a discarded garden tent upstairs. No, that’s a little unkind, I suppose. I looked among the clothes, and returned with something suitable.

I handed the skirt to Amanda and she disappeared to change, leaving us all enjoying the warmth of the fire.

I turned to find Sylvester texting Bernard. “Just covered Amanda’s pants with eggnog. 😊”

A text came back from Bernard a moment later – “Can’t chat, going in for colonic irrigation! 😉”

“Wow,” said Sylvester. “They really know how to have fun in England.”

With that Sylvester disappeared upstairs to the bathroom, leaving Ali and I to talk about how he and his family were enjoying their second Christmas in Canada. He told me how well his daughter had settled in at school, and how his wife had managed to find a good job in the bank. It wasn’t until ten minutes or so had passed that I realized both Sylvester and Amanda were still absent.

I glanced at the carriage clock on the mantelpiece.

“How very odd,” I said to Ali. “I wonder what could have happened to Sylvester?”

Ali turned his eyes toward the heavens, or one of the bedrooms upstairs, depending on your point of view. He had an ominous look on his face as our eyes met.

“Just how much brandy is in that stuff,” asked Ali.

“Enough.” I said. Sylvester is Italian.

I hope you are enjoying the run up to Christmas. We will be here through the holiday looking after all our friends and members. I’m thrilled to say we’ve been getting a lot of new members in to My Little Black Book. If by chance you are alone this Christmas it’s a great idea to get into My Little Black Book and message some of our other members. They’re all keen to hear from others and make new connections, and we all love to connect, however distant, at this time of year.

Merry Christmas,

😊

Fiona

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Elegance.

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.

🙂

Fiona

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

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Fiona’s Shopping List – Eye Shadow.

Since I had Sylvester do some work on my electrical wiring I have been having trouble with my fuses. Periodically I find myself bathed in darkness as the electricity goes out. I’ve had several electricians come to check the system, and another is coming to check the fuses shortly. Currently I blow three or four a week under the stairs. Frankly, I’ve had about as much as I can swallow. I think I should just replace the entire wiring system.

That, however is not the main reason I am writing today. I thought I’d include a little tip for all those crossdressers who are yet to master their make up, and let’s be honest, there’s a few!

Auntie Kittie’s nieces and nephews get into so much trouble. Don’t forget, you can enjoy Auntie Kittie’s Diary on my Patreon for just $1.99 a month. Join today for Clothes Maketh The Man, Auntie Kittie and a wealth of crossdressing content.

Generally a girl starts playing with make up when they’re nine or ten years old. These are often forrays into mum’s handbag or make up draw and at first they are disastrous. However, particularly after playing with friends, they gradually improve. As they get older their makeup often becomes bolder and they learn various subtleties in their choices of color and their techniques.

Many crossdressers struggle, and get upset with themselves for not getting great results from the very start of their makeup use. This can be disheartening. I understand, and you should be aware that it doesn’t have to be that way. Be patient and practice.

While I don’t generally give specific make up tips – there’s many others out there who do amazing makeup tutorials on Youtube – I will offer this. If you choose subtle colors, using minimal amounts, you can gradually incorporate a few colors into your everyday regime without putting yourself into a position where you’re exposing yourself unnecessarily. A subtle amount of eye makeup to sharpen your look is a great way to feel feminine and to gradually improve your makeup skills.

The palette above is a good example of what you may want to start using. Nothing too garish, unless you are really ready to go full Ru Paul on the world. If you’re just starting out, applying a nice blend of shades now and then will be satisfying and even if you’re not completely ‘out’, can really help you enjoy your look.

After using make up for years I can firmly attest that less is generally more. Don’t be afraid to go for ‘subtle’. It will build up your confidence and if you can integrate it into your daily life. Then as you do gain proficiency you will find that experimenting with a greater range of tones is easy.

The other tip I’d add for anyone using eyeshadows for the first time is to be sure you have a selection of brushes. Applying the shades with a nice brush gives you even coverage and makes merging one color with another much easier. Using a little foundation on the eyelid will provide a smooth start point, though sometimes when you just need to grab and go, it’s not entirely necessary.

Enjoy the video tutorial below, but be sure to explore the Amazon link below for color palettes that might work well for you. In the end be sure to remember that practice makes perfect.

Don’t forget, you can join my Elite Whatsapp Group to enjoy chatting with new friends about your adventures with makeup. Check out the Elite Whatsapp Group here.

Fiona.

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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.

🙂

FD

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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.”
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Sylvester’s been polishing his nob again.

As you probably know in my work as a busy crossdressing advertising account executive I lead a busy life. In the company I work for there I several boards and committees, with a lot of new faces recently. And I have to say I have been asked to sit on many of them. I like to avoid any of the contentious ones of course. This week however I did chair a couple of meetings to decide who we would award company scholarships to. The committee met at my house and we went over the details of the candidates.

I must say, I am probably not making myself popular but I tend to favor the under-achievers. I am a firm believer that the way schools measure performance is meaningless. Besides, over achievers always make it. It’s those of us that don’t come first in the class that need the help, don’t you think? Rewarding excellence is alright, as far as it goes, but it’s not a bad idea to celebrate those of us who didn’t come home to a wall full of trophies, too.

After the meeting and my guests left I decided to cycle over to Sylvester’s place, where I found him in his garage pulling out bits of old equipment. He has all sorts of things in there. Old parts of motorcycles, a theodolite (whatever that is), and other items picked up in estate sales and auctions. He seems to gather these things in the hopes that one day they will once more be useful. Quite what anyone would do with four Eight Track cassettes of Captain and Tennille I really don’t know. All the same, he always seems happy out here rummaging about in the junk.

“Isn’t this beautiful,” said Sylvester, a piece of electrical equipment in his hand. “It’s a brass light switch. It just needs a good polish.”

As Sylvester put some brass polish on a cloth and started polishing his nob I cast my eyes over the piles of assorted junk in the garage. I supposed it brought Sylvester some joy, and as one who does like to invent things from time to time I supposed there was some practical purpose to it all. He seemed quite content playing with his equipment. A very male trait, I supposed.

I poked about in a couple of the boxes, eventually finding a lovely old motorcycle headlamp, wires sprouting from it like colorful vines looking for something to creep up, a little like some of the junior execs at the advertising agency. I idly decided to polish the metal surround of the lamp, as Sylvester retreated into the house to make us both a coffee.

As I polished the metal, and I know this seems surprising but then such things happen to me all the time, a strange pink mist seemed to form before me. At first I thought I’d open the garage door to let the mist dissipate, clearly an environmental hazard. As I rose to my feet to open the door a form appeared and emerged from the clouds of pink mist, a beautiful woman wearing a sparkling dress and carrying a rainbow colored wand.

“Can I help you?” I asked, taking in the long dress and tiara worn by the beautiful figure before me.

“No, Fiona. I’m here to help you,” replied the beautiful woman before me. “I am the Lady of The Lamp – your fairy god milf, and I am here to grant you three wishes.”

“Well, that seems a little random,” I replied, surprised at her appearance in Sylvester’s garage. I mean, you sort of expect these things to happen in sacred places, not in a hoarder’s garage.

“You summoned me,” came the reply as she waved her hand in front of her face and gave a little cough. “Sorry about the mist.  It’s always like this. Ozone. Something like that.”

“Well, it’s a good job I found you. Poor old Sylvester is out here polishing his knob and things all the time, and he’s never said he found a Lady Of The Lamp,” I replied.

The lady looked a little embarrassed and said, “You should tell him to take it easy on that. He could go blind.”

“That’s exactly what I told him, but what can you do,” I replied. “Boys will be boys. So what are you doing hanging out in an old motorcycle lamp?”

“What sort of question’s that? Old oil lamps, that’s what everyone seems to expect but we haven’t been doing that in years. I’ve got a sister who’s just moved into a Tesla’s LED system. I’ve been stuck in this thing for the last eighty years, but here I am. So, three wishes. Let’s do it so I can be free once more.”

“Well, I suppose I should go with ‘world peace, personal health and wealth.’” I replied.

“Oh, come on, Fiona. You know that’s like the ‘lunch box A’ of wish making. You can do better than that,” she responded.

“Well, it would be nice if Rainbow wasn’t so lonely up there in the light house. Something to make her life better might be nice,” I said.

The lady closed her eyes and snapped her fingers.

“Oh, and someone stole my boobs last fall. They took a bag from my car and it had a pair of 44 DD’s in it. I’d like those back,” I said and a moment later I felt my sweater tighten and a wonderful pair of breasts emerged.

“There you are,” said the lady of the lamp. “Fresh from Glamour Boutique – https://www.glamourboutique.com/buy/breast-forms/affordable-crossdresser-breast-plate – you can’t go wrong. Now, what’s your final wish?”

I’m not going to share that with you, I’m afraid. It’s a little personal. With that the lady gave me a final smile and vanished to roam free.

By the time Sylvester returned with the coffees I did find that I was feeling much more at peace with the world. And so to the moral of the story… These are not easy times, but with a little creativity we can find ways to move forward with a smile, great make up and a pair of 44 DD’s on our chest.

Have a lovely week.

Fiona

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Marjorie has an infestation!

Hi,

Sitting in my kitchen, enjoying a quiet cup of tea, wearing my favorite kimono, I was surprised to see Ali hurrying through the gate in the fence between my garden and my neighbors. Ali, you’ll remember is my wonderful gardener. He’s a Syrian refugee, and the nicest man you can imagine.

He bustled into the kitchen looking flustered. 

“It’s Marjorie,” he said looking worried.  “She has the most terrible infestation!”

“She has?” I said, a little puzzled.

“Yes, in her bush. It’s very distressing.”

“Well, it would be,” I replied.

Ali is a gardener, but he was a professor at Damascus University prior to the war.  He is very knowledgeable about botany. When it comes to making my garden bloom, he’s sure to be all over it. 

“If her problem spreads to our garden it’s going to be horrible. Aphids are little monsters! I think I should take care of it. If I don’t everyone in Huckleberry Close is going to get it.”

“That’s a wonderful idea,” I said.

Sure enough, later that evening, when Sylvester and Bernard were over enjoying a drink with me at the end of the day, Ali came back happily convinced he’d resolved the issue. He had used some sprays, a little trimming and Marjorie’s bush was looking very thoroughly groomed.

Well, done, Ali,” I said. “After rooting around in Marjory’s bush all afternoon, I think you deserve a little clap.”

As you can see, my life is never dull. .

🙂

Fiona 

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Fall is a great time to adjust your look.

As we kiss goodbye to a hot summer it’s time to start adjusting your look. Just think of all those lovely russet hues that you can lean into!

I was just saying to Sylvester this morning, “It’s a time to start adjusting into the warm colors of the fall.”

Sylvester is very touchy these days, what with Amanda travelling the competitive eating circuit with Marjory, my next door neighbor. He does get quite jealous. She’s been gone for weeks. It’s a wonder that Pig and Pig Farmer Weekly hasn’t gone into terminal decline. I understand she edits the trade publication even while on the road.

For Sylvester, putting together a fall wardrobe consists of switching the denim blues to the Carhartt browns, though I have to admit Carhartt does have some functional women’s workwear these days – https://www.carhartt.com/c/womens

It’s rather hard for Sylvester to compete with Marjory, for that beating lump of gristle that passes for a heart inside Amanda’s breast. Marjory is even more down to earth than Sylvester, and she just blunders forth. It’s quite remarkable to me that she ever gave birth to such a sensitive boy as Max, who as you likely know, looks after the technology things for me. Marjory is the kind of person that announces her pregnancy by switching to menthols. She even has a sticker on the back of her truck that says, “My other car is also a truck.”

A gold star dyed in the wool lesbian if ever you saw one! You just have to love her!

Sylvester can’t really compete, although he does turn a few heads down at the hockey rink when driving the Zamboni. Some women are just impressed by the wheels. Honestly! Men! It’s all rather infantile if you ask me. A little like the time he tried to help his friend Roland with his circus act. Roland is a talented spoon thrower. Yes, I know – it’s all to do with the terms of his parole. But you get the idea.

You can find some nice ideas for fall outfits HERE – on my Pinterest page. You may also want to check some of the offerings from Amazon below.

Fiona

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What are you driving?

I could not help noticing, whilst driving home from the advertising agency the other day, the names on the back of vehicles. The model names of vehicles are of interest to me, from both the branding perspective and what it tells me about the drivers.

Have you been reading ‘Clothes Maketh The Man‘? Enjoy the ongoing serial now in its third year.

A therapist member of mine recently pointed out to me that several of their erectile dysfunction clients did indeed drive muscle cars, in more than one instance a Hummer. Frankly I feel anyone driving a Hummer should be on their knees begging forgiveness from their children as they pump heat into an increasingly fragile environment. On the other hand, given the erectile dysfunction issues associate with Hummer ownership theirs a good chance that having children is one complication these thoughtless tools will not have to concern themselves with.

Sylvester, on the other hand has shunned the muscles cars and even removed the photo on his office wall of him posing with his Dodge Penetrator 3000. I am pleased to see him mellowing. I do remember the day he pulled up outside my house, on his phone calling me to tell me he was there.

“I’m just pulling into your garage,” he said. “No wait, I’m reversing.  Pulling in again… backing up, and going in again now. Perhaps I should go in the laneway round the back. I can get the back way, but it’s a bit tight.”

You know, I may have said this before, but Sylvester can be quite coarse at times.

Personally I like to drive a Buick Vagina. It’s the limited Silhouette edition. So much more my style. Both feminine and powerful, with the twin turbo V6 with the cuddle seats option.

Vehicle names and designs do tell us a lot about their drivers. I noticed a Kia Soul in the traffic as I was driving home, and I can only speculate that some Korean designer sat down and thought hard about what a car designed for Spongebob Squarepants might look like, and then took up the challenge to build it. Ironically the driver of this particular vehicle did look like a cartoon character.

Sebastian, my vegetarian personal trainer, drives a Kia Hymen when not riding his electric bicycle. His sister, Rainbow, drives a Nissan Slide with a synchromatic gearbox. Amanda drives a Prius, which is entirely predictable, while of course Ali, my gardener, drives the Smart Car with a rifle rack on the rear window, adapted to carry his gardening tools. He’s proud to declare he always shows up with his hoes.

One of my Vancouver members, Lenni, is originally from Alaska, and proudly tells of her mother having driven a Ford LTD wagon. This vehicle, with a 7.5 litre engine has the dubious distinction of being capable of hitting a moose, killing it, and then being able to transport it back to the trailor park for butchering. I can’t help thinking life in Alaska holds wonders I am pleased not to have either witnessed or shared.

Instead I think I’ll go and get Sylvester to change the fluids in my Buick Vagina.

Have a lovely week.

Fiona