Let me grab a towel.

Here I am getting this post ready for you in the hotel, on a hot evening here in Chicago. I hardly know where to start, so much has been going on. I suppose I should start by telling you all about Sylvester and the other night.

I wiped my chin and said to Sylvester, “Oh, my goodness!”

It took me a moment to catch my breath. “It wasn’t as salty as I expected. I can hardly believe the quantity!”

“My tool is almost worn out!” Said Sylvester. He held the pliers, and dabbed his face with the napkin. Eating east coast lobster at a fish restaurant in Chicago is a great pleasure, but a very messy one. What did you think we were doing?

Sylvester was wrestling the last bit of lobster meat from within the claw. What a character he his. Always with a tool in his hand! As I am sure you know, he’s my mechanic and friend. We flew down together to visit Bernard in the hospital who was recovering in hospital..

I should explain. If you followed last weeks email you’ll know that Bernard managed to get himself Tazered in the arrivals lounge of O’Hare airport. That is far from where the drama ended.

He was rushed through to the hospital, and there – to my horror – they found that Bernard, who had become so excited by certain aspects of my physique, was in the middle of a heart attack. I had thought he looked rather like a freshly landed trout as he convulsed following his Tazering, but not being familiar with how one generally responds to a Tazer, I thought this quite normal.

Fiona’s Crossdressing Blog

Even the police officer who gave Bernard the jolt looked quite concerned. He even showed up in the hospital as Sylvester and I were visiting. Bernard was still unconscious, and here we were three days later.

The police officer walked into the private room I arranged for Bernard, and held out his hand. “Officer Speltman,” he said. “You can call me Sparky.”

“Sparky,” said Sylvester. “Are you serious?”

“Yeah… They gave me that nickname at the academy. It kinda stuck…”

“Well, Sparky,” I said, “I’m Bernard’s friend. I’m sure he would be grateful you came and visited. If he were, you  know… conscious.”

“I’m sorry he got the jolt.  I didn’t really have a choice in the circumstances.”

I took the business card Officer Speltman offered and said I would call him when we had further news. Then Sylvester and I went and found a hotel, and a fish restaurant at which to have some dinner.

“I still don’t quite understand why Bernard didn’t get up when the cop told him to,” said Sylvester.

“I think he was concerned about his clothing being… disarranged. He was in a state of some excitement.” I felt awkward telling Sylvester that Bernard had a prominent erection and was concerned about embarrassing himself when he stood up. “Let’s just say he was hard at work, when it happened.”

The following morning I had a call from the hospital with the worrying news that Bernard was extremely ill and that the hospital was doing it’s best to locate a heart for a transplant. I am, of course, quite shocked – as I am sure you are. I will keep you informed. (See what happened next by going here: https://fionadobson.com/bernard/zipper-job/)

In the meantime, I have a very special self hypnosis file for you tonight.

This file is all about taking it to the next level, so join me in a lovely relaxing self hypnosis exercise and have a listen. And of course, I will be sure to let you know about developments with Bernard.



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?


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.



The Gender Spectrum And Your Box.

The Gender Spectrum And Your Box.

At last, the weekend. It was very busy this week at the advertising agency, and Max, my next door neighbors 19 year old son, joined me to ‘job shadow’. He’s been following me around (no change there!) to see what I get up to and see if perhaps after he finishes college he should consider a career in the world of advertising.

Unfortunately, he chose to job shadow the week we are moving offices. All the same he made himself very useful, his muscly arms being put to good use helping pack up my office.  I have some lovely plants in the office, and made sure they were all packed nicely in a big chest, so they would survive the move.

“Would you like me to drill your box?” Asked Max, as I was stretching over the desk, reaching to unplug a phone.

“I’m sorry?” I said, a little perplexed. Max has always had what might be described as a healthy curiosity about my body, but this seemed uncharacteristically forward.

“Drill your box? Holes,” he said.

I looked very puzzled at him.

“You know, so the plants get more air.”

I realised he was talking about the big box I was using to move the plants. Better air flow would indeed help them.

“Max, you are such a good boy. You go right ahead and drill what ever you need to,” I told him.

That, however is not the main reason I decided to send this message. I decided to send a quick note to tell you about a great BBC radio broadcast I think you may enjoy. It’s an investigation into the idea of gender. I think you may find it every bit as fascinating as I did. It touches on the idea of gender not only being more complex but actually completely fluid.

You can listen to it here: Do We Have Enough Genders? http://bbc.in/23v0LRz

Let me know what you think of it.


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.”