Category: Sylvester

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Finding you in good health.

I put my own success and good health down to my adherence to a strict and healthy diet. In Canada we have a wonderful chain of health food stores, called ‘Tim Hortons’. Where ever you roam in this great land you’re never far from a healthy nutritious snack. In fact, I think it fair to say Tim Hortons has become a Canadian institution as identifiable as our polite nature, love of hockey and insistence that we elect a Prime Minister that doesn’t have a serious personality disorder.

As you may know, my wife, Amanda and our neighbour Marjory, are traveling on an ornithological tour of Western Europe.

Amanda, my wife’s appalling friend, has come down with a severe case of Canestin poisoning,  which I understand is rare but not unknown in menopausal lesbians. I hasten to point out that I do not subscribe to Sylvester’s view that when lesbians are exposed to large amounts of oestrogen they run a severe risk of having their ovaries explode. Sylvester somehow equates this to the idea that ‘males have to masturbate at least once a day, or else their testicles burst into flame.’

In my kitchen with Sylvester, Bernard and Max, my neighbours son, I poured the tea.

“Whoever told you that nonsense,” I snapped at Sylvester.

“My mother,” he said.

“Sylvester,” I said in mock protest, “that’s complete nonsense! We all know that Max has to masturbate at least four times a day to prevent such a mishap!”

Young Max blushed and pursed his lips. I smiled at him fondly. Since that embarrassing matter of the carrot, poor Max has been very subdued, poor lamb.

I made the mistake of asking Bernard how he was, since he’d only been out of the hospital a few days.

“It’s all these tests,” he said. “They make me feel like a bloody pin cushion.”

“I’m sure the doctors are doing their best,” I reassured him.

“I’ve become a slave to my prostate,” he said sounding downcast.

“Aren’t we all,” I replied a little uncertainly.

“It seems to rule my life,” he continued.

“How very awkward,” I commiserated.

At that moment the kitchen door was flung open, and in staggered Sebastian. He looked terrible, with a weeks growth of facial hair on his chin.

“Good God, Sebastian! You look like you got interrupted halfway through eating a raw porcupine. What on earth happened?”

Sebastian was shaking with energy. “Just got back from Mexico,” he shouted. His words word tumbling over themselves to get out.

“I did the ayahuasca retreat
It was
 It was
” he was stammering his words out, his voice shaking.

“I think you’d better sit down and have a glass of water.” I said.

I decided to call my sister, who works at the local hospital. To cut a long story short, she swung by and using the drug testing kit nurses often carry, she determined that Sebastian’s Ayahuasca retreat could more accurately be described as an LSD retreat. That, and that he’d probably spent the last five days sleeping in a burlap sack. Not bad for a cool $3000.

As my sister was leaving she glanced at Bernard, and said, “Oh, Bernard. I didn’t see you there. I didn’t recognise you from the front.”

My sister does two shifts a week in Proctology.

This week I’d like you to take a good look through my Pinterest for some clothing ideas. As you know, I love my members to experiment. Have a lookand see if there’s anything there that takes your fancy. And before I leave you, I’ve a special request. Help our girlfriends at The Downtown Eastside Women‘s centre. They could use a hand. See the panel below for details.

😊

Fiona

 

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Let’s make a difference this week. We’re appealing to you to help out some friends of ours. The Downtown Eastside Women’s Centre supports vulnerable women on Vancouver’s Eastside. Mostly these are people who have fallen between the cracks of society’s safety net. We’re focusing on this charity today because it’s in a cool city, it’s a cause I know my members will fall in line with, and because the big charities have the big advertising budgets – and the small ones are often overlooked. This is a small charity, and your gift will make a huge difference. You can support this charity by going HERE and giving something, however small, to help.
Nice Legs, Shame About The Face! Wise words from the early 1980’s. The last verse is the best one. You can always enjoy the Fiona Dobson Playlist HERE.
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There’s an intruder in the Queen’s back passage!

I can only say that each time I visit London I find myself captivated by the majesty of the city, and the historic landscape in which I find myself. To think these streets have been trod by several kings, and a multitude of queens is quite overwhelming. I was in the city taking care of some legal business, and took the chance to slip off and do some shopping between meetings.

Sylvester and I were particularly interested in some of the historic slums in a deprived neighborhood called ‘Knightsbridge’. Strangely enough whilst there I saw neither knights nor a bridge, however I came across a cute little corner store named Harrods, which offered a selection of shopping ideas, which is foremost in my mind at the moment. As fall approaches it’s time to start looking for warmer but stylish clothes.  My personal favorite fall look is the sweater dress, and as I had a few minutes to spare I slipped into Harrods to check out what they had on offer. There were some interesting offerings, but ultimately I found myself sidetracked and looking around the lingerie department, as usual. You can see some wonderful examples of what I was after below and the beauty of online shopping is that you need never find yourself sidetracked and perusing lingerie
 Right. Moving on.


The traffic in the tiny streets was unbelievably slow. Deciding to walk back to our hotel, Sylvester approached a London Bobby (what we would call a police officer) and asked if the traffic was generally this slow.

“No, sir,” he replied. “There’s been an security alert. An intruder was seen lurking in the Queen’s back passage.”

Sylvester pointed out that we’d had much the same problem on more than one occasion in Canada, at which point the officer told Sylvester it was time to be moving along.

But that’s not the main reason I’m writing today. We’ve been adding new content to the Premium Program recently looking at issues including the trouble with online stalkers, (Do you have one? Do you want one?) and how to deal with them. We’ve also added material around how to recognise when a woman is interested in crossdressing. The Premium Program is really very developed these days. Be sure to sign up if you’d like to take your crossdressing to the next level.

Have a wonderful week.

😊

Fiona

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“Shut up and eat your squid, you stupid bitch!” – words for a crossdresser to live by.

Hi,

Today I’m sending you a short message today from Puerto Vallarta in Mexico, and will likely send you an update later this week.  I admit this is me being lazy, but it’s something you may enjoy.

Having a few extra airmiles, I decided to bring Sylvester with me on a quick getaway. I thought that the sun might do him good. Poor fellow spends so much time covered in oil under vehicles, with some enormous tool in his hand, although I am sure that’s some people’s idea of heaven (Mildred!). I’m sure it all gets very frustrating for Sylvester. So, in the spirit of kindness I asked him to join me for a short break on the Pacific coast of Mexico.

It’s a delightful place to visit and very liberal. We feel so welcomed on what can best be described as ‘the fun side of the wall’. Our Mexican friends are not only very liberal, they’re also fun loving and accepting. I’d always recommend this area to my members who want somewhere to escape to where they can find an exciting local scene free of judgement.

It has been a glorious few days, however fate played a curious part when Sylvester ended up sitting in the Skybar pool, chatting to a delightful Afro-American lady. Isn’t it funny when a person just gets carried away, before long their brain just seems to shut down to the gentle sizzling sound of their skin being turned to something resembling bacon as the sun feasts on their fair Northern European flesh.

As we walked down the street later that evening, Sylvester as red as a firetruck that had just had a fresh coat of paint, and myself tottering along the cobbled streets on a pair of lovely new heels, I couldn’t help commenting to my swarthy friend, “Well, at least when people see the two of us, they’ll know I’m the sensible one. They’ll marvel at what you’ve done to yourself, and then say ‘Well, I guess the crossdresser is the good looks and the brains in that equation.’”

“Do you really think people will notice?” said Sylvester.

“Well, only if they can stop laughing long enough to register it. I mean, let’s face it, they’ll have to get past the waves of heat rolling from your body. Perhaps they’ll think you’re in a circus or something. You know, some sort of performer. That or that you were involved in some kind of nuclear accident.”

As I voiced the sentiment, Sylvester shifted uneasily in his shirt, which must have felt like a razor against his beet red skin. We’d ordered some delicious seafood, and I ate as elegantly as I could, while admiring my new shoes at the same time. The food was excellent, and the restaurant, overlooking the old cathedral in the city centre, afforded a wonderful view of the night lit city, alive with parties and fun, and a little lightning dancing on the far seaward horizon.

“Look,” I said to Sylvester, “We should focus on the positive. If it gets chilly in the evening, I can just ask you to move a little closer and you’ll keep me nice and toasty! You’re like some energy efficient heater. Although to be fair you’re really screwing up the global warming thing!”

“Shut up and eat your squid, you bitch!” Said Sylvester with a laugh, and for a moment I was lost in the magical warmth of the night. What lovely words to live by. We should all ‘shut up and eat our squid’ at times, I thought reflectively. And that’s so like Sylvester, really. I leaned over and slapped him on the back in gratitude for his worldly wisdom.

Have a lovely week.

😊

Fiona

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What do you think of my dumplings?

Hi,

“If we slip this sausage between these two buns,” I said to Sylvester, “it looks pretty tasty.”

“I think a little cream…” mused Sylvester, thoughtfully. “Oh… Sebastian’s coming…”

“I’m sorry?” I said.

“Sebastian’s coming! He maÄ·es a lovely seafood dip!” continued Sylvester. “Yes, he’s a good man with a welk. But I think it’s your dumplings that are really going to get people excited,” insisted my hairy friend.

“Yes, I’ve noticed they seem to get people going!”

As you can doubtless tell, Sylvester and I are planning the spring picnic. I’m thrilled to say my wife has returned from her travels.

Regrettably I find myself called away on business in England. I’ll be be returning shortly after she leaves on a long planned ornithological holiday touring western Europe with Amanda and Marjory. I understand she’s been blown away by some of the lesser finches and the abundance of tits.

It’s such a busy time of year but I hope you’re not too busy to participate in My Little Black Book, where for just $2.95 a month you can connect with some new friends from around the globe or around the corner. It can be so nice just to share a little time on Skype and chat about your dressing and compare notes. Perhaps you’ll connect with some friends and find yourself organizing an ornithological tour for yourselves. Who knows, you may even find yourself getting to grips with some tits of your own!

😀

Fiona
Whether you’re one of our members in Africa, or in the far hills of India, Julie, Katia, Oakley and I are here to support you. 70% of our members are in North America, by I strive to include content of interest to our global audience of over 1000 unique visitors a day.  🙂  Fiona
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Strip Twister? Huh?

 ‘Imagine,’ Julie said, ‘if our Little Black Book members could post a chat message with a pic of themselves right there.’

I should say that on Julie’s insistence we’ve been playing a very intricate game of Twister with Sylvester and Sebastian. Now, I must admit that while Sebastian is very flexible, Sylvester is about as loose limbed as a fridge. In fact, now that I think about it, I have compared Sylvester to a fridge on several occasions.

Julie, by the way has a very mischievous way of playing Twister. It’s quite simple. She calls it Strip Twister, and one can only touch the floor with one’s hands or feet. Any slip up results in the loss of an article of clothing. Now, imagine that image uploaded to My Little Black Book.

Max was so intrigued by the idea that he got to work on it and now we have exactly what Julie was looking for. You can now log in to My Little Black Bookand chat with others, and upload images of yourself in the middle of a Strip Twister game, or anything else you feel like.

Don’t worry, the images scroll off after a while. You might post what you’re wearing right now, or how you’re doing some eye makeup or even a pic of your cat in drag, if that’s your thing… (Ilena!).

If you’re not already a member of My Little Black Book and would like to join the fun, why not go and sign up tonight.  You never know what’s going to pop up next!

Now, Sylvester is trying to get his leg over Julie. I think I’d better intervene.

😊

Fiona
Chastity Devices – Breast Forms – Wigs – Corsets


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Fire and Furry.

I’m emailing you having just returned from the heart unit, where I am happy to relate that Bernard is in the process of recovery from his rather unfortunate incident with a carrot.  This is much to the relief of Max, who for a moment thought he may have blood (or rather carrot juice) on his hands after shooting Bernard with the aid of Sebastian’s motorcycle. If this is all a bit confusing you may be able to catch up here.

I arrived home to find Sylvester sitting at my kitchen table looking more confused than a Trump supporter who had recently learned that he’d won a months free food at Hooters, only to discover that he had to complete a skill testing question asking him to calculate the area of a square measuring 2 inches by 2 inches, before being eligible to collect his prize. I asked Sylvester what could possibly be wrong.

“It’s this business with North Korea. My dad was out there years ago, and that didn’t go so well,” said Sylvester.

Now, in case you’ve been living under a rock – which might be the safest place to be under the circumstances – then you might be unaware that people are talking about the possibility of nuclear war. At times like this one is forced to ask the big questions. ‘What’s it all for?’, and ‘Isn’t there hope for humanity?’, and ‘What does one really wear for Armageddon?’.

As I looked down at my troubled friend, I was forced to conclude that one should always look on the bright side, and dress up for the occasion. Seeing Sylvester’s legs, also brought something else to mind, and consider that this is a man who looks like a gorilla and a fridge got together and created a baby.
I am of course talking about the need to deal with body hair when one crossdresses. The need to look one’s best supersedes all other considerations as the nuclear clock ticks toward midnight. Sylvester’s legs are very hairy, and if one is to meet one’s end looking fabulous either waxing it off, or at least disguising the body hair is a great place to start.

Not all of my members are able to shave their legs. For those who discretely dress without the knowledge of their partners, suddenly appearing without leg hair may be something of a give away. One member did successfully claim that their new swimming regime required them to remove as much body hair as possible, but this isn’t going to fly for some members.

In the quest to disguise body hair the fishnet pantyhose are your friends. Better still, try a fishnet body stocking. No one should be without one, in my opinion. If you’re unable to find one locally, you can follow this link and order one on my website.

So, the question remains, faced with the unpleasant eventuality of nuclear annihilation, what would your outfit be? Personally, I think nice summer dress and some heels, pretty pink bra and panties. Feel free to let me know.

Now don’t forget, you can now join My Little Black Book for just $2.95 a month by using this link – https://gumroad.com/l/mMgcZ.  Be sure to let me know once you’ve paid and I’ll get you set up.

😊

Fiona

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We’re firming up our members.

First of all, I feel I should address a matter of concern to many of my members. Angela in Arkansas asks, ‘Is it possible that White House spokesperson Sean Spicer and Sarah Huckabee Sanders are the same person? I have never seen them appear on camera together.’

I am so glad you asked me that. Naturally I am a keen commentator on political matters – my views being held in very high regard in some circles. I have several sources close to this matter and let’s just say that you’ll be seeing a lot less of ‘Sean’ in the coming months. I protect the confidentiality of my members very diligently as you know, so I am precluded from saying more. Suffice to say that Sean may be accepting himself as he is, and creating himself as he wishes. I can neither confirm or deny whether he is a member of my programs.

This weekend I have organised a barbeque for my friends. Sadly, my wife is travelling, leaving me to entertain myself. As I slipped into a new bikini and tiny pink skirt today, I found myself considering how very lucky I am.

I have such an eccclectic group of friends. Sylvester with his unusual tattoos and enormous chopper. Bernard, my photographer always wanting to expose himself. Sebastian, my personal trainer, who incidentally has just taken up pole vault. I very unusual choice of sport.

And of course, who could forget Max and Ali – still rummaging about in the arboretum looking for his hoe. This weekend I am also playing host to Katia Thornwood and Julie, who’s been hard at work (literally) stimulating new male members.

Perhaps I should explain that. We had a special promotion last week, for father’s day. This resulted in some wonderful new men joining my Little Black Book as admirers. I am thrilled to see the list of members growing and firming up all the time.

I said to Julie just the other day, “Julie, you need to take the members in hand, firm them up and make them grow!” She’s been breathlessly applying herself.

As my friends started to arrive for the barbecue and Sylvester busied himself at the grill, I joined the boys in conversation.

“But, Sebastian, darling! Why pole vaulting. It seems so… I don’t know, suggestive.”

“Not at all!” He insisted, turning his sausage on the grill. “Personally, I think it shows great self coonfidencel”

“Well, if you say so,” I said. “Mind you, it’s all a little dangerous, if you ask me. Plunging your great pole in a slot and getting up like that. It reeks of over compensation!”

“Its all about keeping it stiff,” said Sylvester, ever helpfull

Sebastian glanced at him, doubtfully.

“We’ve got pills for that,” chimed in Ali, from where he was showing Max the difference between a Chrysanthemum and Chlamydia.

Ali has been doing rather well with his English classes. One would never guess he arrived from Syria just six months ago.

 

“Sebastian ,” he called over toward the grill. “You’re obviously overcompensating, my young friend. I have some friends who can help you with that.”

I sometimes wonder what they teach him at that English class. Nonetheless, his integration seems to be coming along nicely.

I’m watching as Max tries to engage Katia in polite conversation. Now that really is the lamb attempting to lie down with the lion. I think I should go and interpose myself between them before Max ends up being served up on a skewer.

For those of you who don’t know Katia, she is a somewhat stern woman. Statuesque and beautiful, but very commanding. Her wonderful travelogue is being published on my website at http://FionaDobson.com in episodes – look for The Travelogue Of Katia Thornwood. You’ll be hearing more from her. Suffice to say that her holiday entertainments went far beyond looking at temples in Cambodia.

I hope you have a lively weekend and enjoy the summer weather. By the way, as I mentioned, we’ve had an influx of male  members (phrasing) in My Little Black Book. Now’s a great time to join, if you’re not already a member.

We have a major expansion of our website underway. My objective is that there should be something new almost daily for you to check into and occupy yourself with. Check it out and come back whenever you feel a little femme. You’ll love what I’m doing!

😊

Fiona
Imagine if some of your graduating class could see you dressed. What might they think?
Are you reading the exciting adventures of Andy in “Clothes Maketh The Man”?

Manipulated and taken advantage of by the evil Devina, Andy finds himself compromised into dressing. You’ll never believe what follows!
If you haven’t yet dived into the extraordinary serialised feminization adventure you can find it here:

Read the story – Clothes Maketh The Man https://fionadobson.com/clothes-maketh-the-man-part-1/
Not yet signed up for the Premium Program? Take your time, but when you’re ready jump in and join the fun.  You can sign up for full membership – US$ 35 a year – here: https://fionadobson.com/premium-program/
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Sylvester and Max are jacking off in my garden!

Sylvester and Max are jacking off in my garden!

Hi,

+++ A quick explanatory note: Members who sign up for the Free Program, and Premium Program Members, get my messages the moment they are written. They are posted as blog comments about a week later, so belated Merry Christmas. Have a great New Year! +++

My goodness, if you could see what’s going on outside my window. I can hardly believe is! I’m standing here in my Christmas lingerie, and my heels, and quite shocked at what I can see going on out there!

Ali, my gardner has just told me, “It’s ok, Fiona. It’s just Sylvester and Max jacking off in the flower beds.”

Now, I know you can imagine me standing here in my flowing red silk robe, mouth open in surprise. I am staring out at the snowy Montreal scene, and everybody seems to be having a wonderful time! Oh, perhaps you should even be here!

Let me explain. I’m watching Sylvester’s muscle bound arm pumping up and down and Max, my next door neighbours 20 year old son laughing – I think he’s licking his fingers – yes, he’s spilled some Bailey’s Irish Cream on his hand, or at least I think that’s what it is. And Ali is watching, engrossed in the unfolding scene.

They’re laughing and very jolly, Sylvester’s face red with exertion, and he has a look of deep concentration. Apparently, Ali’s Smart Car slid off the drive in the snow as he pulled into the icy driveway. It slid into the flower bed, and onto a rock in the rockery. Max and Sylvester were already at my place enjoying a Christmas eve drink, and now the three of them are working away to lift the little vehicle off the rock and manhandle it back onto the drive. What Christmas excitement!

I should hurry along, Amanda, the queen of tweed will be here soon, and Bernard is coming over. My wife, sadly is travelling. She’s a slave to her job! In the meantime, we are a fun gang, all hoping that Christmas will go with a bang!

I hope yours does, too! Have a wonderful holiday and remember, be careful if you are driving in the snow. Otherwise you too might find yourself licking Irish cream from your fingers after jacking off in someone’s garden!

Merry Christmas,

🙂

Fiona

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Time for a Halloween touch up!

As Halloween approaches and the souls of the dead prepare to walk the earth, any number of my friends are preparing to dress up and wander the streets in the dark. Actually, now that I think about it, most weekends many of my friends spend their evenings doing precisely that regardless of the time of year.

I was conferring with Sylvester in my kitchen, examining a few articles of lingerie, trying to decide what best to wear for my Halloween night party. I finally decided on fishnet, stiletto heels and a bodice, with a steampunk look. Perfect.

I asked Sylvester what he planned to come as.

“I think Donald Trump, if I can find the right costume.”

“At this late stage, I’m not sure you’re going to be able to find a giant dick costume!” I said sympathetically.

At that very moment Amanda, my wife’s unbearable friend, arrived at the door and knocked so hard I felt sure the roof would cave in. She has all the grace and delicacy of a garbage truck.

She barrelled in, coughing and spluttering like a diesel engine that hadn’t been run in a while. Amanda then went on to tell us of the latest disaster to befall her. Amanda was coming by, fresh from her gynecologist. Now, if there was ever a job that requires a strong stomach, being Amanda’s gyny would be the top of that list. Apparently Amanda was in the midst of an exam, had a coughing fit and one way or another the poor man was taken off to hospital with a broken wrist!

I will spare you the details, but it was all rather distasteful. Then, just to make matters worse, Sylvester let slip that he was coming to my party, which so far we’d successfully kept secret from Amanda. She then promptly invited herself to the event!

Reluctantly I asked what she would be coming as.

“Well,” she said, expansively. “I think I’ll come as that CNN broadcaster that looks like me.”

Sylvester and I looked at one another, puzzled. I was thinking, maybe Lou Dobbs, but he’s with Fox now. Maybe Wolf Blitzer?

“You know,” she persisted. “The blonde. Megan whats-her-name
”

“Megan Kelly?”  I asked.

“That’s her,” said Amanda.

“Oh,” I said. “The likeness is uncanny.” Megan Kelly looks about as much like Amanda as a carrot resembles plague.

“Well,” I said. “If you stand next to Sylvester as Donald Trump, all you need do to look like Megan Kelly is wear any form of period costume.”

But, that’s not the main reason I am writing to you. I recently had a delightful email from Brandi, in Yakima, WA in which she enclosed a great face pic which she had touched up using an app called YouCam Makeup- Makeover Studio. I’m sure we all appreciate a good touch up, don’t we? So this week I am offering a free membership of my Little Black Book to the best retouched Halloween pic which uses YouCam or another similar makeup type filter. Keep in mind that any pics you send in may end up on the website – so don’t be surprised if I place them there!

Have a wonderful Halloween, and at this time of year – when so many of us are having so much fun – spare a thought for Amanda’s gynecologist!

🙂

Fiona