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Beautiful Ashley Baron

I do so love swimsuits that have that lovely high waistband. As I looked at mine hanging from the back of a chair in my garden, snow drifting down I slipped into the hot tub.  A light steam seemed to rise into he chill night air, as I sat in the warm water watching the snowflakes and sipping a negroni.

I was fortunate this week to enjoying interviewing Ashley Baron, a familiar face on Tumblr and more recently Twitter. As we sat in the freezing night air, surrounded by hot water and the beautifully manicured bushes Ali, my gardener, has been so busy with, we chatted about her journey and what crossdressing has meant to her.

Ashley started dressing following a breakup with a girlfriend. She’d left some of her things, and one night curiosity overcame Ashley, and suddenly there ‘she’ was. Whilst always a little curious about reaching for a pair of panties, and exploring the idea of gender fluidity, this was her first real foray into crossdressing. At the age of 23 she discovered a world which would be a natural fit.

“I was surprised how natural it was for me,” she tells me. “I think the most unusual thing for me when I started crossdressing was realizing just how feminine I actually looked in those clothes. It really kinda shocked me, and just made me want to see how far I could push it.”

Asley’s weapon means business.


Ashley has always admired strong female characters. For her these were the role model that would steer her values and her life. A principled and genuinely authentic person, Ashley found great joy in cosplay – and emulating the characters that inspired her. Unafraid to take on a challenge she dresses provocatively and challenges herself. The character of Babydoll in Sucker Punch is one of her favorite costumes and one she pulls off with consummate skill.

When there’s a light breeze in the Quebec night, the clouds skid across the sky, and the stars break through from time to time. It’s quite lovely.

Ashley carried on, “At this point I crossdress about 90% of the time in my life, and thankfully, I’ve always had a family who supports me. It’s the same with my job. I bartend at the same place I was bartending as when I didn’t wear a bra to work!”

Ashley laughs as she adds, “My bosses are awesome. I suppose the only thing that has changed is that I make better tips in a push up bra than I ever did as a ‘normal’ bartender.”

I asked her about the way she’s become quite an online personality. She’s so cute when she blushes. Perhaps one of the most endearing aspects of Ashley is her genuine modesty.

“I have never really considered myself an online personality,” she confessed. “But i’m slowly starting to realize I might be and I seem to actually have a fan base and people who love me, and that is the most amazing feeling ever. I love that people are inspired by me! That’s such a cool aspect of what I do, that I can bring joy to other people’s lives. And as far as Tumblr goes I’m sad to see it change. Tumblr was a platform that let me express myself, and now that is being taken from me and others, and that’s disappointing to say the least.”

Now, I have to say that I was a little surprised when I noticed my neighbor Marjory and her girlfriend Amanda (my wife’s appalling friend) next door peering over the fence. Amanda, as you know, is one of the only women I know who wears tweed underwear. I believe it’s specially designed by Carhartt for her. Marjory has recently returned from a competition on the busy competitive eating circuit. Ironically she appears to be leading in the sausage division, which is beyond ironic considering she is a committed lesbian. I hurried the interview along as I knew Marjory and Amanda would be invading the hot tub shortly.

I had thought Ali had discouraged Amanda from infiltrating the garden, but he felt it was unfair to shoot her with the paintball gun so often, so I have tried to adopt a more humanitarian approach, at least over the Christmas period. It’s a little like the Christmas Truce of 1914.

I asked Ashley if she had any suggestions or advice for other crossdressers. Her reply illustrates Ashley’s very generous nature and I am quoting her verbatim.

She said, “I never want to influence too heavily people who have to make their own decisions on these things, however, I will say this: Never feel embarrassed or nervous or ashamed about who you are. We are finally (almost nearly finally) pulling away from a society that has been telling people forever that even considering crossdressing, or transitioning, or even questioning your own sexuality is a “bad/wrong/evil” thing… it’s not. It’s not a bad thing to discover who you are and ask yourself who you want to be. Never be ashamed of trying to find out who you are.”

I could not help but feel that so accurately mirrors the mantra of what we do here, in our tag line – “Accept yourself as you are, create yourself as you desire.”

If you would like tosupport Ashley’s journey she has a Patreon account which you can use to send a little appreciation here: https://www.patreon.com/AlsoAshley

This is a season to be generous, and I’d strongly suggest reaching out to her showing your support.

Finally, as Marjory and Amanda squeezed through the fence defences and came into the garden with their towels, Ashley added “There is nothing sexier than someone who is confident in themselves.”

I glanced at Amanda, wondering if there is such a thing as too much confidence. As editor of Pig and Pig Farmer I suppose it is important to have an opinion about everything, and she certain has that.

Ashley has a healthy diet avoiding fast foods, and focusing on vegetable and chicken. It’s a far cry from Marjory’s red meat based diet. As we relaxed the night become still more beautiful, and I was left thinking how Ashley really is the perfect guest. Be sure to show your appreciation HERE.

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Sylvester has an enormous package.

First of all, in response to the many emails that have flooded in response to last weeks multiple choice competition. The correct answer was, of course, B – ‘He didn’t use enough lubrication.’ Congratulations to Mildred of Colorado Springs for getting the right answer before anyone else on that one.

It’s been an exciting week, not least because Sylvester burst into my kitchen this morning, a giant package in his hand.

“Goodness,” I gasped. “Sylvester, what an enormous package you have!”

“It’s just arrived from Amazon,” he declared proudly. “It’s your Christmas present.”

I hardly knew where to put myself. Instead of opening it, I decided to place it beneath the Christmas tree in my living room along with several others for my friends, as we’ll all be gathering on Christmas morning to open gifts together. I do so love this time of year.

It’s a special time as we celebrate two things. The first is, of course, a season of good will to all. And the second is The Fiona Dobson Crossdressing Man Of The Year. Last year, you may remember Sarah Huckabee Sanders won, baffling medical science. So, if you have any suggestions please email them in, and the most popular ones will be put on the website for members to vote on.

If you’re enjoying the website and emails be sure to register, or commit to The Premium Program. Your $35 subscription not only gets you the great Premium Program, but also helps support our members who are unable to join the Premium Program, by allowing me to offer our free program at no cost. It feels good to support our community.

Till next time,

🙂

Fiona

Don’t forget – you can always find The Fiona Dobson Playlist HERE. Put it on and enjoy a fun day!

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Let’s show our support for Dr. Helen Webberley

Dr. Helen Webberley is one of very few people who have dared to stand up to an establishment that has neglected transgender patients and left them with no support for many years. For so many people, myself included, GenderGP saved my life from a time where my local Health Board wanted to leave me on an endless waiting list. GenderGP provided a wonderful and supportive service and gave me access to treatment that I needed.

On December 3rd 2018 Dr Helen Webberley was found guilty of operating an unregistered clinic for transgender patients. She was fined £12,000.

Click Here To Read Media Article

Dr. Webberley has done nothing wrong other than dare to stand against a system that wasn’t doing enough for its vulnerable patients.

Now is the time for the trans community and trans allies to come together and let Dr. Webberley know how much we support and appreciate the work that she has done for transgender patients.

Look at what the patients have to say about the work of GenderGP; how can we stand back and see this wonderful work threatened! Click Here to Read Words of Patient Support .

We are not seeking to raise funds to cover any legal fees. Simply we are raising money specifically to say “thank you” to Dr Helen Webberley for all the life-saving support she has given the transgender community, and for the personal sacrifices she has made.

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Clothes Maketh The Man – Part 22 is out!

Yes, just when things looked like they can’t possibly go worse for Andy, he finds himself getting in deeper!  Follow the painful progress of the hapless Andy – who would be him!

Put out to work by the evil Devina, Andy finds himself put into service with Chantelle. What could possibly go wrong?

Read Part 22 here: PART 22

Did you know that the quickest way to be sure you’re getting the latest Clothes Maketh The Man is to use The Fiona Dobson Crossdressing App from the Google Playstore?

 

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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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The dangers of yoga pants.

The dangers of yoga pants.

You are catching me at a very inopportune moment, so I’m going to hope you can indulge me a moment. Here I am with my hands covered in a white solution – goodness, it get’s everywhere!

Let me explain. This morning, Sebastian was over getting ready for my daily yoga class, when I got a call from Marjory (Max’s mother) from next door. She asked if perhaps she could come over and join our yoga class.

Now, I think you all know how important I find yoga. It really helps me get in touch with my feminine self. And wearing tight colorful yoga pants is just a bonus.

Naturally I agreed Marjory should join us, however she was not sure if she had quite the right clothes. I wouldn’t want her colors to clash with mine so I sent Sebastian over to her place to have a quick look at what she was going to wear.  This was a big mistake.  To cut a long story short Sebastian now has a virulent rash which he seems to have picked up from Marjory’s pussy.

I had no idea he was allergic. Fortunately he has some homeopathic tinctures in his first aid kit. Let’s hope this does the trick!

Have a great week, and remember, if you develop a nasty little rash it’s a good idea to treat it with plenty of lubrication, vigorously. And often. It’ll either cure it, or you’ll go blind.

😊

Fiona

PS. If you are not a full member think about signing up – HERE . When I see payment go through I will start you on your path. I work though everyone’s messages a couple of times a day and work to get you moving quickly. I know you’ll love it. Email me to let me know you’ve upgraded.

Fiona.
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This music video simply has to be played. There’s a companion on here. Let me explain. In the 80’s we had some great pop bands. We also had some that didn’t quite make the cut. In fact, The Reynolds Girls ‘I’d Rather Jack’ did get into the top ten on the music charts, but more recently rose to some fame as one of the top 100 worst pop records of all time. Personally I loved it. I love the energy and the girls sense of fun. They were so cool that they even did a reunion video in 2007 which is just painfully delightful and has to be watched. If only we could all be so honest and ready to enjoy life. Now, if you really want to elect a celebrity leader, why not one of these two?  For those who have been asking for a playlist of the music videos I use, it can be found here.
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Corsets – The shape of things to come.

There can be little doubt that the single piece of crossdressing equipment that makes the greatest impact on how you look is the corset. Suddenly you have a waist, and look very different!

That dress now hangs a little more naturally. You have curves that make you excited and others wild with desire. Everything is different.

You’re going to love the selection below. Take a good look and then experiment. Keep in mind that buying a little larger than you think you need may be a good idea. You can easily be cinched down a size or two.

Remember, it’s great to experiment with a few ideas. If you can find a girlfriend to help you, you’re going to enjoy this even more.


Don’t be afraid to experiment with corsets. They are fun and give you an instant waistline. Some have a longer body style than others.  They can be worn over or under a blouse, and there’s the tricky question of whether on not you want an underbust line, or one that cradles breast forms, or your natural breast mass.

Eventually you’ll want to spend a substantial amount on a corset. At that point a professional fitting is a great idea. When you’re spending upwards of $300 on a corset, you don’t want to make mistakes. However, you’ll likely find it’s worth every cents. Until then try any of the ones you see on this page and have some fun with them.

One of the most fun aspects of corsetry is the idea of going steampunk.  I love to waer steampunk clothes and the corset is a staple of the style.  Below are a few great corsets that can combine with jeans, or a long skirt, and boots, perfect for a steampunk adventure. I can hardly wait to get out there once more.


 

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What have they ever done for us?

What have they ever done for us?

Good morning and welcome to a wonderful election day in the US. If you’re getting ready to vote, slip into some heels, do your makeup and get out there with plenty of time to make a difference.

Just this very morning I was walking in my garden with Sebastian, my personal trainer, and Amanda, my wife’s appalling friend. She’s heading over the border to the US this afternoon to vote, of course, like all good people should. However, as we were walking Amanda got a call from my wife, who as you may know is currently travelling.

Sebastian and I could not help but overhear Amanda’s comments, and politely listened in to the one sided conversation. Now the important details I will skip over, except to say that I was wearing one of my lovely pleated maxi skirts that I find so very comfortable and a pair of suede boots. However, returning to Amanda, who it should be noted edits Pig and Pig Farmer, the first publication in the US to endorse Mr. Trump in the last elections.

Continue reading “What have they ever done for us?”

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Knock Her Up!

I had a very strange conversation with Ali this morning. We were enjoying a cup of tea at my kitchen table, and the topic fell to politics. Now, as I am sure you know, Ali is my Syrian gardener. He came to Canada as a refugee with his lovely two daughters and wife.

I am so pleased to say his girls are doing to so well. They’re both A grade students now, and are loving high school here in Montreal. Ali himself was a professor at Damascus University in the Biology department. His special interest is, unsurprisingly, botany.

I found it most curious to hear him talk about American politics.

Looking very thoughtful he said in a very considered manner, “it’s really very reminiscent of home.”

He must have seen the look of surprise on my face.

“Really, these rallies Mr. Trump has. They are just like ours back home.”

“I hardly think…”

“It’s just the same. The words are a little different. But other than that, it’s very similar,” Ali insisted

“Ali, it’s completely different,” I protested.

“I’ll admit, our young men were chanting “Death to America”, instead of “Knock her up”, but it’s all the same really.”

I poured a little more tea before pointing out, “I think you’ll find they’re chanting “Lock her up!”

Continue reading “Knock Her Up!”

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Hobbs Island Hotel – A Halloween Ghost Story

Hobbs Island Hotel

By Fiona Dobson

When Elizabeth died my world stopped revolving and it seemed my life ground to a halt.  It was an unexpected death, as so many illnesses are, but mercifully swift.

Merciful, that is, for her. It left me with an empty life before me. How many years? I don’t know. I suppose it doesn’t matter.

So it was months later that I found myself waiting on lonely shore, in a gusty wind looking out at the bleak expanse of water, with Hobbs Island several miles distant, feeling desolate. But that was how each day felt at the time. Completely empty. It had been just six months, and my world had gone from full, exciting and fulfilled, to something as forbidding as that shoreline itself.

I should explain. I’d arrived a few days early for the workshop I was scheduled to give, with the intent to use the time to write. I had a piece to complete about the psychology of addiction, and it had been my intention to use those few days to complete the article in the quiet of the retreat. I suppose I should have checked with the organisers more carefully. I’d just assumed the hotel would be open, even though it was out of season.

After walking from the railway station to the quay, I made the call to my contact only to learn that the hotel on Hobbs Island would be closed. As it happened, the owner had been contacted and gave me permission to stay, even though I’d have to fend for myself in the empty old building.

Continue reading “Hobbs Island Hotel – A Halloween Ghost Story”

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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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You won’t believe what I found on my doorstep.

On the whole I do not approve of large people with too much facial hair looming in my doorway. Even more so at 3 am.

That was the sight that greeted me this morning. I enjoy my beauty sleep, most of all to protect my looks, but also so I am fresh in the morning to write to my members. And last night, as my very understanding wife was once again traveling, this time at a conference in somewhere called Poughkeepsie, I was enjoying a night of calm sleep wearing a burgundy camisole. When I heard the chiming of the door bell, I pulled on a thick robe and went downstairs to find the henge-like form of Amanda, my wife’s appalling friend, blocking the doorway, like a couch abandoned by someone who had been trying to get it through a door that was marginally too small.

Continue reading “You won’t believe what I found on my doorstep.”

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Making the most of summer.

As summer moves toward its gentle close, and the warming glow of the forest fires in the distance thankfully fade, I am forced to remind myself to make the best of the last weeks of this glorious summer.

What better way to celebrate the sun and move toward fall than by enjoying the soft flow and movement of a stylish and comfortable swing dress. I was saying this to myself as Sebastian sat, dejectedly at my table in the kitchen.


 

He was staring intently at his phone, a frown firmly welded to his face.

“What on earth’s the matter?” I said, pouring a glass of organic free range goats milk.

“It’s my sister, Charmaine” he said. “She’s so wonderful. But…”

“But what?” I asked.

“But she’s just posted a picture on her Instagram, and there’s a great big ring on her finger. She’s engaged.”

“What delightful news,” I said with a smile.

“Well, it would be delightful. You see she went to Cuba, a lovely little village, and met this wonderful man she’s fallen in love with.  She flies back every few months and is so in love.”

“But Sebastian, this is wonderful news,” I gushed. “I’m so happy for Charmaine.”

Sebastian’s sister is so sweet. She has been waiting for the right man so long, and finally her prince has come.

“Well, it would be wonderful. Except this last time she flew to Cuba she was supposed to be at her grandmother’s funeral, and cried off saying she was broke.”

“Oh,” I said.

“And since my mother’s now discovered Instagram, it’s only a matter of time till she learns that instead of planting my dear old granny, she was out gallivanting around the place getting herself engaged to a Cuban. I can almost hear the clock ticking.”

I spread the lovely dress out as I sat, and turned to Sebastian to reassure him.

“Darling,” I said, “I’m sure your grandmother wants nothing less than her grand daughter’s happiness. Besides, the old trout will never know. And your mother will get over it. Your sister has found something magical. and that’s really what counts, isn’t it?”

I know my readers well enough to know that you may have a suggestion to help me here. Help me out and use the comments to suggest what Charmaine should tell her mother.

 

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Playtime With Fiona 5 – Come and check out my bush!

Such goings on about the place!

Few sights can be more disturbing than Amanda, my wife’s hideous friend, in a two piece bathing suit. It was this unsettling image that greeted me when I arrived home this afternoon following a photoshoot with Bernard at the advertising agency.

Amanda was in our back garden, trying to tan her body, in much the same way that if you leave a piece of leather in the sun it becomes hardened and cracked. As I let Hannibal, my little black and brown Dachshund, out into the garden to my surprise he sprang across the grass and made a leap to bite Amanda’s bikini bottoms. As you can imagine, Amanda’s scream was so shrill you’d think someone were cutting through concrete with a rotary saw.

“Get him away! Get him away,” she screamed. Never before has so much flesh been restrained by so little fabric.

I sipped on my margarita as I watched Hannibal trying to pull the bikini from her. Then said, “Calm down,Amanda. He’s just being affectionate.”

In response Amanda started to run round the garden, arms flailing, with a dachshund hanging from her bum.

“Hannibal,” I mumbled, as I took another sip of my margarita.

“He’s gone rogue!” screamed Amanda.

The last I saw of her she was flapping away down the street, hotly pursued by Hannibal, who doubtless thought it a great game. I suspect I’ll be hearing more about this incident later.

That however, is not the main reason I am writing to you. Tonight is a warm Montreal evening, and it’s the perfect time to listen to the latest Youtube version of Playtime With Fiona. This weekends offering is a special one, and a little unusual. I know you’ll love it. This weekend is also the perfect weekend to experiment with some lighter summer shades of lipstick, a summer shade of eye shadow, and of course some new outfits for the beach or lake.

Feel free to share some pics. Don’t forget you can always submit a photo for me to share on the website here: https://fionadobson.com/your-pics/

Have a wonderful weekend.

Fiona