Clothes Maketh The Man – Part 1.

It was one of those crazy situations that you just never believe can happen. I was visiting my sister in San Francisco and arrived at the airport only to find my luggage was in Albuquerque – which was not part of the plan at all.

I’d flown out of Chicago just hours before having been called to come in and interview for a position with an advertising agency, and I was excited about the possibility of a great career move. I’d packed my best suit, a shirt and some shoes, and that was about it. I could be in and out of San Francisco in a coupe of days, and I’d stay over with Jennifer, my sister.

Jennifer is one of those people others look at and think is the perfect sister. However, behind closed doors she could be a little harsh, to say the very least. I think growing up I’d seen a mean streak no one else had been exposed to. Either way, I always knew there was something a little dark about her.

I wouldn’t say I am exactly ‘sensitive’ to these things, but there was definitely something about the way she would tease me as a child. You just never knew how far it would go. And there was always the possibility it would go to far.

Continue reading “Clothes Maketh The Man – Part 1.”

A little something extra.

I realise I may be out of step with some of my members when I say this, and this is really just my own opinion, but I do feel quite comfortable limiting some of my social interactions as we go through the whole Corona thing.  I’ve taken the opportunity to trim out some of the less positive people in my life, and do more of the things I enjoy.

It’s a little bit like having the opportunity to fine tune one’s life a little. Reducing the negative people in my life, and engaging in the things I enjoy has become something of a goal. Sadly, Sylvester is having a more difficult time of it, being so outgoing and social.

Sylvester, for example, throws enjoyable parties, though sometimes they really do get quite out of hand. On one evening last year he had a rather unusual 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.

Continue reading “A little something extra.”

Do you remember the first time?

Hi, I was chatting with some of my members online the other  night and we got to talking about our first time. I don’t think any of us really knew what we were doing at that time. I was about 5 when I first tried on a pair of black panties. My cousin had been over, and they’d been left.

 

I think my mother must have washed them and put them in my draw by mistake.  Either way I found them, and realised they weren’t mine.  I tried them on all the same, and I can remember thinking it was naughty. I can also remember getting an erection – which was definitely a little strange.

For some of us, it was our sister that played ‘dress up’ with us. For others it’s some other situation completely. 

Of course we all have a different path into this – and for each unusual start there’s an unusual outcome.  I know so many men who crossdress, and hide it from their wives, only to fnd later (when their guilty secret is discovered) that their spouse really likes the fact that they like to dress up. And of course there are the ones that go the other way.
 
Of course we all have a different path into this – and for each unusual start there’s an unusual outcome.  I know so many men who crossdress, and hide it from their wives, only to fnd later (when their guilty secret is discovered) that their spouse really likes the fact that they like to dress up. And of course there are the ones that go the other way.

 

In the end, we all know we just have to be the person we’re meant to be – and find ways to accomodate that. There’s good ways and bad ways to do that.

I’ve just added a new page to my site that will help people understand a little about this. On my site you can tell your own story in the comments section of the following page – https://fionadobson.com/my-first-time/.  You might find your own story is not so unusual. It’s a good thing to share.  Don’t forget to register on the site. That way you’re sure to get a lot more out of it.

If you are interested there’s a little about my own journey here: https://fionadobson.com/the-three-reasons-i-couldnt-stop-myself-from-crossdressing/

Ironically, it’s often not until later in life that many people embrace this behaviour. Perhaps it’s just when we feeel more comfortable with it.

Now, Sylvester, my mechanic has just pulled into the drive.  He wants me to take a ride with him on his chopper. Have a lovely evening!

🙂

Fiona

The top ten things you need to know to stop being a complete sissy bitch.

I have to say that I always try to be positive, and with the exception of when speaking about Amanda, I exercise my mother’s good advice. If you have nothing positive to say, then say nothing. Wise words.

You will understand how writing this piece has been a challenge, and yet one I feel I have to complete. However, after considerable deliberation and talking with both Sylvester and Auntie Kittie, I have put pen  to paper. Auntie Kittie pointed out that sometimes you have to grasp the nettle and say that which needs to be said.

“It’s like that time in South Africa,” said Auntie Kittie, “when I had to tell a trans friend, who was staying at the school out there where I am a school governor, not to sun bathe naked. The grade 9 biology students a confused enough already!”

“No, Kittie,” I replied. “It’s not like that at all, but I still have to write it. There are some members that might need to hear it.”

Continue reading “The top ten things you need to know to stop being a complete sissy bitch.”

I don’t know what came over me!

 

My photographer, Bernard, had a session with me this week. He’s a very nervous little man. So many times he gets so close, and his excitement overwhelms him. He starts getting so excited as he points his longest lens at me and says for me to relax, while he is just panting with anticipation. It’s a good job I like him so much.

“That’s it, darling,” he whimpers. “Keep it going.”

And I am working away so hard in front of him, which I have to say I love. Sessions in the studio are so much fun. I become a different gurl. Sometimes I just don’t know what comes over me!

Afterwards I have to slip back to the office, and the IT manager looks at me strangely. He said to one of the partners in the firm, “Some times I just just don’t know what gets into that one, I really don’t.”

I’d like to say how happy I am this week, as I’m getting into the office once a week. There’s really no need for me to be there more, as I love working from home, and I am able to cover my responsibilities easily from home. I hope you to are able to adjust to these new practices. Be sure to let me know how you are going.

Chat soon.

Fiona

I am surrounded by idiots.

I sat in my garden this afternoon, socially distanced from my two expectant looking guests seated nearby, beside the gentle shape of a bouganvillia, off-setting the colours of the smokey pink and soft grey of my summer dress. Sylvester and Rainbow, Sebastian’s sister, looked on hopefully.

“So, let me get this straight,” I said. “You’re asking me – and Sylvester I think I am quoting you correctly – which is better:

                A: Sylvester’s idea, a facial scrub which is made by simply driving along behind a gravel truck while sticking your head out of the car window.”

At this point Sylvester was nodding and grinning like a chimpanzee that has just found the key to a kitchen cupboard full of banannas.

I continued, “Or B: Rainbow’s idea, a facial scrub made of vanilla extract, cream, vegetable oil, oatmeal and aloe, which is then smoothed on the skin and allowed to dry, before driving along behind a gravel truck while sticking your head out of the car window.”

Rainbow smiled at me vacantly and nodded.

Sometimes, I feel like I am surrounded by idiots. It may seem a harsh thing to say, but it’s true. I considered the question for a moment.

“Obviously,” I said at length, “the answer is ‘B’.”

Sylvester looked crestfallen. Before he could ask why I continued.

“The answer is ‘B’ because you could charge more for it and therefore make more profit. This might mean that in time you could afford to hire the team of psychiatrists that would provide the help that you both so obviously need.”

In these trying times of Covid-19 and failing businesses I am finding many of my friends are searching for new business ideas and as such my marketing expertise is in great demand. Perhaps you, too are surrounded by similar challenges.  If you are, you have my sympathy. Such is the lot of those of us who serve.

Be sure to join my Patreon if you’d like to lend a hand to myself and the sadly challenged people with which I surround myself.

Have lovely weekend, and stay safe.

Fiona.

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Stacy’s New Job – Mistress Meg.

As I fastened the final leather cuffs to Mr. Barton’s forearms, I turned to Stacy and said, “Correct me if I’m wrong, Stacy, but if I’m not mistaken I can’t help thinking Mr. Barton is not a completely happy man.”
 
For those of you who have been reading my emails to you regularly, you will know I am a very perceptive and sensitive person. I’m very generous by nature and I pick up on these things.
 
“What makes you think that?” said Stacy, as she selected a pair of shiny heavy steel nipple clamps.
 
“Mostly it’s the sobbing. The whimpering, too. The squirming is also something that does give him away a little.” I paused for a moment and then, addressing Mr. Barton, added, “What on earth is the matter?”

Continue reading “Stacy’s New Job – Mistress Meg.”

OK, boomer.

As I was saying to Sylvester just the other day, to have another language is to possess another soul.  The reason I say this is quite simple. For those of us older than millennials, we are in the process of learning a new language.

No longer can we talk about chairmen, manning the ship, or even manhandling the sails. Today we have chairpersons, we staff the ship and we manage the sails. The way we speak has rightly come to a point that change is not merely become a desirable goal; failure to change identifies us as dinosaurs.  As uncomfortable as that sentence makes me, I realise it is true.

The term ‘OK, boomer’ comes to mind. It encapsulates tolerance of a dinosaur that grazes idly in the village, but that everyone realises is going to die out sooner or later, leaving the world a better place for their eventual departure. So society changes.

Continue reading “OK, boomer.”

The Pastor Comes To Tea – Mistress Meg.

I looked at the young pastor and offered him another cup of tea. He sat in my room with a look of hopeful expectation.

“I would love to contribute to your fund, and I must say that, in principle I am of course an avid supporter of anything that helps disadvantaged inner youth,” and with that I paused and leaned a little closer, my cleavage spilling into his eyeline.

I continued, “But, I wonder, Pastor. What can you do for me?”

The young man looked a little surprised, then replied, “Naturally, I’d like to help my benefactor in any way I can.” I couldn’t help noticing the struggle he was having averting his eyes from my breasts.

I smiled at him, placed my hand on his knee, at which he nearly jumped out of his skin, and then I said, “Don’t worry, I’m sure there will come a day when you can do some sort of service for me.”

“Y,yes… Of course. I’ll be happy to…”

“Good! And that day is today!” I replied quickly.

Continue reading “The Pastor Comes To Tea – Mistress Meg.”

BREAKING: Vaccine Found! Trump to announce cure.

Trump to announce vaccine has been found for bisexuality.

“We believe there’s only a few cases, maybe 15. Soon they’ll magically disappear. Our non science based approach gets a thumbs up from the electorate. And our thumbs really are way up!”

Speaking from the Rose Garden Trump talked casually with reporters after the announcement.

“You know I am a stable genius,” he added. “I don’t get why everyone thinks this administration is a laughing stock. Bleach anyone?”

The Grin And Bare It Nudist Colony.

I was relaxing in my garden this afternoon when I got a distraught call from Rainbow, Sebastian’s sister, asking to come round immediately. Of course, I said yes, always supportive of my friends. Besides, Sylvester had just left, having got my asphalt. He’s doing some work resurfacing the driveway.

“You’d better drop by, now I’ve got my asphalt,” I said down the phone.

Rainbow has just got back from a few days at what she calls a ‘retreat’. She does this once in a while, escaping to the Grin And Bare It Nudist Colony on a nearby island, in the southern Gulf Islands in British Columbia. It’s a rather strange sort of escape, involving naturists engaged in yoga and improv comedy. I suspect there’s a certain number of them that also become engaged in open sea swimming in an attempt to escape, or at least they would be if I found myself confined on an island in such circumstances.

One of the regulars at this particular location is a man who has turned to unusual street performance for his living.  Rainbow, who sometimes teaches yoga on the island, has been encouraging this gentleman, assuring him that street performance could be a great way to gain a small income for the rest of his life.

Continue reading “The Grin And Bare It Nudist Colony.”

My hand on your flies.

My good friend Sylvester was looking very concerned.

“I really think I ought to get my junk out,” he said, sounding very distracted.

“Well,” I replied. “If you must!”

We were standing around a table in the greenhouse, in my garden. The smell of ripening tomatoes filled the summer evening air.  On the table was a neat little pine box, containing some beautiful lures which Sylvester has made, as he is such a keen fisherman.

I inspected his flies, and i must say it did make me think I should keep my hand in. You may not think this to look at me, but I really do love outdoor sports, including hunting and fishing. I find the gentle rhythm of fly fishing very calming. Helping Sylvester sort out his fly fishing lures, and discarding those that are damaged or ineffective, is a periodic task I help my friend with.

That however is not the main reason I am writing tonight. I wanted to thank the many readers who have messaged me and commented on the series I put out recently about women who love to feminize their partners. In answer to the many requests, yes there will be further episodes added. In the meantime, feel free to use this link to enjoy the episodes that are already posted.

I shall be writing before the end of the weekend. Now, let me help Sylvester sort out his flies. I’m sure he’ll appreciate my attention.

Fiona

Kathia Thornwood on online dating and recumbent cycles.

Most of Katia’s writing is carried on my Patreon at the Seahorse level, however I felt compelled to include this on here. Be sure to check out my Patreon for more of Katia.

I am always interested in the private lives of my clients.  While not wishing to be a part of them, I am interested in the process of observing them.  Understanding what makes them tick makes it so much easier to help them.

I see myself as something of a therapist, albeit in an unusual manner. As I was tightening a nipple clamp on Ian’s chest, I remarked that I am here to help him, after all. A couple more turns, after the whimpering and the wincing has subsided, when observed closely I can enjoy the process and help my client simultaneously.

Dressed in a suspender belt, stockings, and heels I do deliver considerable help – relief even – to my clients. I suppose at some level that does make me a therapist.

“So, Ian,” I asked while adding a further turn to the clamp, “why is it you’re looking so down in the mouth today?”

Continue reading “Kathia Thornwood on online dating and recumbent cycles.”

Date some of my new crossdressing members.

Crossdressing success starts with a desire to create a certain look. What’s your look?

“I can see his nuts from here!” said Bernard, looking through his long lens as he photographed one of the squirrels in my garden. As summer brings my garden into bloom and the wildlife welcomes this warm weather I delighted to see such a profusion of life here.

Regrettably Ali is still locked in mortal combat with several snails he thinks are eating some of my flowers. He’s decalred a jihad on them and is engaged in hunting them down.

In the meantime I thought you’d be interested in the new members joining My Little Black Book. We have so many new members this month, I can barely keep up.

You can now sign up for just $2.95 a month here: https://gumroad.com/products/mMgcZ

Be sure to email me after you’ve signed up, so I can get you set up nice and swiftly.

Sylvester is checking out Amanda’s cans.

What a strange day it’s turning out to be. Our members are all out doing wonderful things. Julia in Holland, one of my favorite members in our Whatsapp Group, has been out and bought some beautiful summery things, and nearby I know Lenni is having a garage sale.

Julia has been doing so well. She, like many of my members in the Whatsapp Group, shares some of her experiences and activities with other members of the group. It makes it a very supportive community.

This afternoon a few friends will be stopping by as the isolation period begins to lift. Lockdown here in Canada has been well observed and the results mean we are now able to begin very gradually restarting 2020. I, like most of my friends, feel that having a glass of wine in the garden with one or two friends is much more comfortable than going out to a restaurant, for the time being at least. It also gives us the chance to have a bit of a barbecue in the garden. Sebastian is hoping to treat us to his sausage later on. I am wearing a denim skirt, tee shirt and a lovely floral mask, and keeping things very simple.

Sylvester and Sebastian arrived a little while ago astride his enormous chopper.

Taking off his helmet he said excitedly, “Amanda’s going to drop by later. She wants me to check out her cans.”

“I’m sorry?” I replied a little surprised.

“Her headphones,” he said. “She says they crackle. She wants me to see if I can sort them out. It’s probably just a loose connection. They were very expensive apparently. Mind you that was in 1993. Still, I said I’d check them out.”

“Oh,” I said doubtfully. “I see.”

I have told Sylvester on more than one occasion that Amanda is in a relationship with my neighbour, Marjory the competitive lesbian eater. Or should that be ‘the competitive eating lesbian’. Well, as I’ve mentioned before Marjory is apparently quite a big noise in the world of competitive eating, although like so many sporting disciplines they are experiencing something of a famine this season.

“You should be a little careful,” I said to Sylvester. “Marjory and Amanda are together, as inexplicable as it may be. I’m not sure that you should be hunting in that particular briar patch. You might get pricked.”

“I don’t mean to be pedantic,” said Sebastian cutting in. “But, I’m not sure you can hunt in a brier patch.”

In the interests of contextual accuracy I rephrased my doubts to Sylvester, saying “I’m really not sure you want that bird in your hand. Better to leave it in the bush.”

Sebastian mumbled something about Sylvester having big hands and added that there are plenty more fish in the bush. I decided I should let it slip past. Instead I shot them both a look of disapproval.

“OK,” I said. “Let’s try this again. I don’t think, Sylvester, that you should have your snout in that particular trough.”

I think I may have to go in a moment. Sebastian has just got a call on his cell and let everyone know that Rainbow will be dropping by shortly and wants to show us her jugs.

“She’s only just got them out of the kiln,” he said helpfully. “She want’s to show us her pottery. It’s come on so well recently.”

Have a delightful weekend and if you’re one of my American members have the very best of Independence Days. To all my members, keep it real and stay distanced and masked if you can. 

Fiona

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