Category: playtime With Fiona

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Sylvester needs some help polishing his chopper.

I couldn’t help thinking, as I clutched my banana, that Sylvester really could use a better diet. He seems to exist on burgers, and grilled cheese.

I was standing in his workshop, having dropped off a fruit basket, thinking it would add some welcome vitamin C to his diet. So many of my friends succumb to the cold during the winter, and I’m sure a fruit basket staves of the flu for many of us,and personally,  I find a good banana a lifesaver at times, don’t you?

I happened to have arrived at Sylvester’s workshop on a slow day at his business, and he was busying himself polishing his chopper. He was breathlessly working away at it, wanting it to be in great shape before the first days of spring.

Quite suddenly, I felt I simply had to help, so I found myself leaning over his great machine, polishing away as only a good gurl knows how. I must say, my tight leggings and my slim hands working away on the surface of the rich round pipe raised a few beads of sweat on my brow!

Sylvester becomes full of anticipation, during these final days of winter. He seems to become agitated at the promise of the excitement of the spring sunshine when he and all his big hairy friends can get together and show each other their choppers. It’s such a male ritual, that I feel quite intimidated by it all. It fairly takes my breath away.

Having said that, climbing astride a throbbing beast and feeling it thrust itself down the highway has always been a secret desire of mine. As a young thing my mother once caught me on a friends ride, and I can only say my cheeks were burning red with shame as she chastised me for my foolishness.

Yes, I’ve often inserted myself into the leather clad world of the kings of the road. And the queens for that matter.

That is not, however, the main reason I am writing to you tonight. I have recently put up a new episode of Playtime With Fiona. This one helps you get into a little shaving that will make you feel great. These are fun activities you can enjoy between tasks in the Premium Program, or even just when you feel like a little adventure. The video below is the most recent, however you can always find some here: https://fionadobson.com/tag/playtime-with-fiona/

Have a wonderful weekend, and if your excited about the onset of Spring be sure to polish up your equipment!

🙂

Fiona
Playtime With Fiona - Get out your razor and slip into something silky!
Don’t forget, I’ve got many free videos for you on Youtube.
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Bernard Gets A Shock.

Well, I hardly know where to start! This week was eventful, to say the very least. On Friday night last week, Bernard my photographer called me very urgently to tell me he needed me to get ready to fly to Hawaii to do a shoot.

Usually I have a little time to prepare, but we ended up flying out on Saturday morning to the spectacular Pacific island I love so very much. Poor little Bernard. He has been under a lot of pressure lately. What with all that travel, and deadlines, and goodness knows what. Anyway, by the time we headed back to Chicago, where we had a meeting on Tuesday, I had noticed he was not looking well.

Bernard has been very odd lately. As you likely know he’s about 48, I would guess. He’s like a sort of uncle to me, I suppose. However, of late he’s been very curious about me, and has been even a little amorous. It’s flattering, but I must say, when I play I usually like to play a little below my age.  I think you know what I mean.

Now, I often love to travel in yoga pants, as they are just so comfortable, and show off my legs nicely. I had noticed Bernard looking at me in a somewhat hungry way. I think you know, I do like to tease him a little, but – well, I really don’t think what happened was my fault. Really.

So, we arrived at O’Hare airport and were waiting for our bags  in the arrival area. What happened was rather extraordinary. I slipped off to the ladies, noticing how Bernard was watching my bum as I walked to the bathroom, and freshened my make up and swapped my travel tee shirt for a fresh one. I always do this, as I like to arrive feeling clean and fresh. I slipped on my heels, which I’d been carrying in my shoulder bag, and brushed my hair. I must say I did look very exciting.

When I stepped out of the bathroom some excitement was going on in the terminal, and I walked back to wear Bernard was. There was some sort of security people running about. Bernard was watching me as I walked, very poised in my heels, toward him. I could tell his excitement was all about me. He was sitting, clutching his Starbucks coffee in his lap.

Now, I have a pretty good idea when a guy looks at me and gets ‘excited’. Bernards baggy cargo shorts were, how should I phrase this, ‘a little disarranged’ by his excitement. His eyes were practically popping out of his head as I walked over to him, turned and sat beside him.

Now, that’s when things began to go wrong. One of those handsome police officers and his friend came running our way, and getting people to move to the far end of the arrivals hall. He shouted at us to stand up, and carry our bags to the far end of the hall. I stood up, but as I glanced at Bernard, I could see he was hesitating. I quickly realised that in his state of excitement it would be very embarrassing for poor little Bernard.

I  leaned over him, and his eyes dropped to my cleavage. I said, “Bernard, we really should go!”

He looked worried, and said, “Wait, errr… errr…”

And then this police officer was suddenly shouting for Bernard to stand up, and the poor dear was white as a sheet. Next thing I know Bernard is being Tazered and twitching like a freshly landed trout.

Later, when I got home and was telling Ali, who was working in my front garden, his first comment to me was, “No, they can’t do that!”

“Well, he did!” I explained.

“But he’s not even black!” said Ali.

“You can’t say that,” I admonished Ali. “In America every one is equally unequal under the law. You need to remember that!”

Silly old Ali! Anyway, Bernard ends up rushed off to hospital. It was terrible, although I must say the nurses had very nice little uniforms. I was quite taken with them. As I say, I can’t bring myself to feel responsible, but theren is a moral to this story. If a policeman asks you to move, even if you have an erection, it may be a good idea to comply!

I shall be sure to keep you informed about Bernard’s progress. He’s currently in the hospital. I am most concerned. I shall put together a nice outfit and go back to visit him after the weekend.

Now, that was not the main reason I am writing to you. I have a lovely new sound file for you.

I know you will want me to keep you informed of Bernard’s progress, so I shall be sure to let you know how he is.

Have a lovely weekend!

🙂

Fiona

PS – If you’re reading this on my blog, you can jump to here to find out what happened next.
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Breasts And How To Get Your Hands On Them.

An essential guide for crossdressers.

It’s Playtime With Fiona and today we’re look at breasts.

So many of us look at drag queens and wonder just what that is beneath their lovely fabrics and designs. And as a crossdresser wanting to look their best, of course we want to get our hands on them!  Well, here’s the short story on what’s going on.  Enjoy this offering and be sure to explore the website thoroughly. Here’s a good place to start – https://fionadobson.com/site-guide

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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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The Only Thing That Looks Good On Me…

Here are a few Christmas ideas.

The Only Thing That Looks Good On Me… from Fiona Dobson on Vimeo.

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Playtime With Fiona – Get out your razor and slip into something silky!

You’ll love the feeling of sexy excitement that a close shave gives you!

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Playtime with Fiona – Crossdressing in a pandemic.

How you think about yourself is as important as the aesthetic of dressing. Here’s a great exercise to help you think in ways that will allow your feminine self to emerge. Give it a try.

You can find more of my content at http://Patreon.com/fionadobson​

Should you wish to find some great ideas for androgynous clothing check out my Pinterest here – https://www.pinterest.ca/fionadobson2…​

Be sure to subscribe!

🙂

Fiona

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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