Sylvester needs some help polishing his chopper.

If you haven’t done so already, Email me to upgrade to the Premium Program.

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: http://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, and soundfiles on Soundcloud.

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.

Bernard gets an injection of energy.

All I am going to say is that “Accidents happen”. Unfortunately sometimes they happen in disturbing ways.

tumblr_o7duvzEzrK1udir1co1_500This month we have a great competition for you for “Playtime with Fiona”. The competition is very simple and there are two $35 Premium Program memberships up for grabs. The first will go to the person with the best photo and funny story about crossdressing. Bernard, my photographer, will do the judging – so blame him, not me! The second of the two Premium Programs will be awarded to an entry selected at random. If you don’t pass in the photo don’t worry. We’re looking for a fun pic, and that may outweigh the glamour quality.

Be sure to send in your enties to my email – fdobson@zoho.com – before midnight on August 31st. I will see Bernard does the draw soon after that.

I have to say, Bernard is a great photographer but can be a little jumpy at times. This is a condition that was definitely not helped by a rather unfortunate situation that developed recently. Amanda, my wife’s appalling friend, had been chatting with her on the phone looking for beauty tips. For those of you who know anything about Amanda, the queen of tweed, you’ll understand this would have to be a very wide ranging conversation. Not so much a discussion about a make over, and more about complete reconstruction.

As Amanda went bleating on, my wife idly made a note on a Post It note in front of her. “Coffee Enema.” The conversation went on and on, and eventually, when it was over, the note got left on the kitchen counter.

I would have forgotten about it, except that it somehow got attached to a notebook I often use, and just stayed stuck to the back of it for a while.

Some days later I was at Bernard’s studio doing a shoot, and when we’d finished he asked me how I manage to keep my skin so clear. I was about to answer him when his phone rang and he had to take a call. As I finished dressing I jotted down a couple of things on a Post It note. I wrote, “Facial exercises, sauna and moisturize.” Then, as I was leaving, I mouthed to Bernard “3 times a day!”

I had left my notebook on his desk, and I just slaped the Post It note onto his desk and made for the door and headed back to work at the agency.

Two weeks later I was back at the studio, and Bernard was glowing with good health and bouncing about the place.

“I am loving this beauty regime,” he ranted. “It’s amazing. I’ve never felt so energized.”

“Oh,” I said as I changed into another dress for the shoot. “I am glad to be of help.”

As I stepped out of the changing room Bernard was setting the lighting up, and taking light readings. I glanced at his desk as he busied himself with his equipment. On his desk was my note, and next to it my wife’s, saying “Coffee enema.” The notes had a big red circle around them and in Bernard’s beautiful German script beside them, the words “Three times daily.”

I thought I should let sleeping dogs lie. With that much caffeine in his system I couldn’t help wondering how Bernard was still alive, never mind sleeping.

That, however, is not the main reason I am writing. Obviously I’d love to hear your stories and see your pics. The best will likely end up on my website, so please remember not to use any real names or details that might identify anyone.

Did you know you can probe my Inbox by listening to one of my Youtube videos here: https://youtu.be/Nrkq0UAf4QU

Have a great weekend.

🙂

Fiona

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: http://fionadobson.com/your-pics/

Have a wonderful weekend.

Fiona

Time to put some color in your cheeks.

Well, I feel quite awkward about sending you this message. As you may know, Max – my neighbors son – has been job shadowing at my work for a little while. The advertising agency is very good for this, but what happened today was quite beyond my experience. I feel I have to share.

tumblr_o4ob3nCqmr1ukdxiso1_500Max had his young friend Micheal drop by the office. Rather than hanging around like a great goon, while Max finished off what he was doing, Micheal worked on something on his computer in my office. As it turned out, Max was tied up and had to work a little longer than anticipated, so his friend sat at the table in my office working away at an assignment for college. He was doing some sort of graphics training.

I was wearing a very thin pale blue blouse, my navy blue bra visible through it. My skirt was also rather shorter than strictly necessary, though no one had ever complained. Either way, what transpired was probably predictable.

I remember clearly freshening up my eye makeup, and glancing in the mirror of the compact as I applied a little more golden glow, noticing the way Micheal was staring at my behind. The only word that comes to mind is ‘drooling.’ One does get used to this.

Throughout the afternoon, now and then I would look up from my work and several times I caught Michael looking at me in a way that can only be described as salacious and lustful. Now, Max has way too many hormones dancing around inside his pants, but manages to control himself, even if I do tease him from time to time. I enjoy giving him the wrong end of the stick now and then and metaphorically giving him a good poke with it. After all, we all love a good poke. However, his friend Michael seemed positively entranced by my figure and unable to take his eyes off me.

I could see his furtive glances were drinking in my shape each time he secretly glanced at me. I could see him getting increasingly uneasy, and shifting awkwardly in his seat. I shot him a smile, as I worked and he blushed. This was all rather cute, until he got up unsteadily and walked over to my desk.

“Fiona,” he said nervously. I could see he was terribly anxious.

“Micheal, darling, what can I do for you,” I said as gently as I could.

“I…I…” He couldn’t get the words out.

“It’s ok, Micheal. You can say anything you want to me.”

He leaned into me and with the greatest of efforts spoke slowly and said, “I want to use your mouth.”

I was more than a little taken aback. I have been approached in many situations, and actually enjoy be propositioned, but this seemed a little odd.

I collected my thoughts and then said, being careful not to offend, “Just hold that thought for a moment.”

I slowly got to my feet and walked quickly out of my office to the coffee room, where I found Max loitering.

“Max,” I said firmly. “Come here! Now!”

He looked at me quizzically and said “Yes?”

“Micheal,” I said slowly, “Is he… Urm… He seems a little,” I didn’t have the chance to finish my sentence.

“Oh, I know,” Max said. “He’s a little odd. Tightly wound. Especially his lisp, and everything. Takes a lot to understand him sometimes.”

“Yes.” I said. “Exactly,” and slowly walked back to my office. As though the fog was clearing, suddenly all became clear, and I realized he must have been asking for a mouse for his computer.

‘Yes,’ I thought. ‘That must be it.’ I knew he’d been working on some graphics and a good mouse would make that a lot easier.

I walked in with renewed certainty and a sense of clarification, a crisis easily averted. Sitting at the table, Michael still looked nervous and awkward. ‘Silly boy,’ I thought, giggling to myself.

“Don’t worry, Michael,” I said. “I’m sure I can help you with that,” and I gave him a smile.

He blushed, and stood up, closed the door of my office and then to my surprise excitedly said, “I altho want your puthy…”

Now, I must get on with this email because there’s so much mounting on my desk, and I am getting a little behind (…phrasing…).

I meant to chat with you as most of my members are in USA and Europe. As we move into the glories of summer a wonderful opportunity comes, as we can apply a little blush, and blame the sun should anyone notice. If you are going out and dressing in public already this may seem a little redundant, of course.

I like as many as possible of my members to integrate a little of their femme self into every day. Using subtle amounts of make up does this wonderfully.

In summer most women actually use a little less make up, though using a bronzer is an exception. There’s no reason in the world why you shouldn’t do the same. Just as secretly wearing panties to work is liberating, using a little additional color on your cheeks has the same effect.

Now, as for Max, I can think of a good way to put some color in his cheeks. Where’s my office ruler?

Fiona

A little something extra.

A little something extra.

Sylvester, my mechanic, throws the most enjoyable parties, though sometimes they really do get quite out of hand. On one evening recently he had a rather fun night during which one of his friends decided they were intent on cornering me and plying me with drink, in the hopes that they might do unspeakable, but delightful things to my body.

“If you think you are going to get that in me,” I said to his friend, “you’re very much mistaken,” as he tried to press yet another drink on me.

“But, darling…” He oozed.

“Don’t ‘Darling’ me. If you think I’m swallowing your…” I was at a loss for words. “… your nonsense, then you must think I was born yesterday!”

Well, this evening I have something very special for you. This weekend I am starting a little thing I call Playtime With Fiona. So, if you’d like to play along have a listen HERE. It’s a fun little exercise for those of you who are a little concerned about dressing in public, or who are just starting out in their crossdressing journey.

So, have a listen and let me know if you enjoy it. The best way to show you liked it is to share it or post comments on Soundcloud.

By the way, I still have about 40 places available in Fiona’s Little Black Book. Currently these are free, but as soon as it goes over 200 entries it will become part of the paid program, so if you want to get into it while it’s still freeemail me saying you’d like to be listed in my Little Black Book. If you’d like to read about it, you can do so here: http://yes-sadie100.tumblr.com/flbb

Thinking about upgrading to the Premium Program? Email me and I’ll get it organised for you!

Fiona