Preparing yourself for your next adventure.

There’s a temptation to think of crossdressing as something people only do in the privacy of an intimate environment. In many cases that is true, though most of us would like to take it further, but stifle this desire.

Breaking out of this mold and dressing outdoors is a major step for many of us and leads to a better understanding of the fluid nature of our gender. Once the initial trepidation is over come – and, yes, I could write a book on that alone – then a new world emerges. It feels wonderful to find this, and for many it’s the first time they feel entirely comfortable and can be themselves.

As one enjoys the freedom to wear what we want, and be who we are, it starts to feel increasingly comfortable. I often point people toward this article to get a better basic understanding of crossdressing, and what it means to you. It’s the experience in the end that is our best teacher, though. It takes courage to make those first steps. You might think of it as the price you have to pay to be your true self.

Continue reading “Preparing yourself for your next adventure.”

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 city 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.

Continue reading “The Pastor comes to tea. Mistress Meg.”

Seeing Past Your Penis.

It’s a sad fact that as people enter the world of crossdressing, and gender explorations, they do so armed with such tragically unhelpful baggage.  I often find myself having to explain to people that just because they want to crossdress, it doesn’t mean they are gay.  In fact only a small percentage of crossdressers are gay. Approximately the same percentage as in the population in general, in fact.

Some time ago we surveyed over 2300 members, and the results were very telling. They can be found HERE.

While being gay is great, it’s pretty obvious that it’s not really got much to do with whether you want to feel more feminine or not. So, now that’s out of the way, their next misconception is that women don’t like crossdressers.

Continue reading “Seeing Past Your Penis.”

Sylvester has entered me!

As summer gently shimmys toward the exit door, and fall gets in the queue to get into the club of the passing year, we’re slowly seeing the weather change. Even Auntie Kittie has started wearing a sweater now and then, a matter of considerable relief to Max, who types up her material.

Auntie Kittie is often surprised how quickly Max gets it up.

“Max is such a dear,” she said the other day. “I’m so grateful he’s so good at putting it in. He’s so thorough.” and then added as an after thought,”… and so quick.”

The poor 20 year old lamb goes the color of a beetroot when he’s embarrassed, and Auntie Kittie will say such things in front of Sylvester and Mistress Meg. And it was Sylvester and Meg who were sitting at my kitchen table this very morning. Sylvester was telling us how in these troubled times we should all be finding ways to lift our spirits. Instead of worrying about the Corona Virus we should be reaching deeply within ourselves and fostering our creativity. Meg was a little skeptical.

I’ve been doing that very thing myself. I’ve been doing a little embroidery, making some of my jeans look a little more feminine by adding a few little designs. It’s really very simple and gives even the most masculine of trousers a nice feminine touch. If you’d like to change your favorite dungarees from the farm yard, or even the ones you wear when cleaning out the slag from the iron foundry this will do just the trick. Even your most stylish denim pants can be personalised and uplifted – and we could all use a personalised uplifting of our denim clad butts, I’m sure you’ll agree.

I leaned over the kitchen table and turned to Sylvester and said, “What do you think of this?”

Sylvester looked at my jeans as I did so, and said, “That’s really very impressive.  I think I should enter you.”

“Sylvester, I…” but before I could speak he went on, as Meg looked on, arms folded and unimpressed.

“I should enter you in the embroidery competition. It’s part of the end of summer cultural fair at the recreation center.”

“Oh, really I don’t think so,” I said. “Most of the people entering are really rather older than I am. They’re quite a conservative lot. I’m really not sure what they’d make of me. I can imagine it would be like that poor South African athlete who they didn’t believe was a woman.”

Sexy jeans – just add heels.

Sylvester looked a little doubtful. “No, I don’t think it would be like that.”

Anyway that’s what I’m doing. Sylvester tells me he’s working on a book. The Complete Idiot’s Guide To Being A Complete Idiot. A catchy title.

“Are you writing it or reading it?” muttered Meg, ever the acerbic wit.

It turns out that half the people in this competition I’m now entered in are young arts students. I thought they’d all be doddery old buffers like Auntie Kittie’s father, who’s staying with her rather than going into a care home. These days that seems a rather good idea. The old fellow is about 150 years old and sits smiling looking into the far horizon. He seems a kindly old fellow, though the dementia is quite complete and he has little idea of what’s going on. He seems cheerful, though.

I said to Auntie Kittie, the other day when I was round there, “He looks like he’s fondly remembering the things he used to do when he was a young man.”

She frowned and agreed.

“Yes, you’re probably right. He’s remembering flying aeroplanes and bombing Germany. He’s always been a belligerent old bugger.”

I suppose we all have our own journeys.

Have a safe, socially distanced week. The Republican convention should provide a few laughs this week… urgh, I can hardly wait.

Fiona

Walking with heels.

One of my members is trying on some new heels.

We talk about everything in the Whatsapp Group.  Here’s one of my favorite members, Julia, with some rather extreme heels. Julia’s come on a long way since they joined.

Join my Whatsapp Group to join the fun.

🙂

Fiona

I’m surrounded by Dicks and covered in Seamen!

Do you know that feeling?  You know, when you can’t swallow fast enough and it starts to dribble down your chin?  I should tell you what happened the other day.

I know you were probably wondering what happened to me last week. Well, yada yada yada, and I end up having my stomach pumped at the local hospital. Perhaps I should explain a little better.

Continue reading “I’m surrounded by Dicks and covered in Seamen!”

Jensen And The Lady Of The Manor – Part 2.

The second part of this series finds Jensen slipping deeper into Mrs Sinclair’s intrigue. Jensen’s unusual punishment becomes evident. Ms. Katia Thornwood’s list is available in it’s entirety here: https://www.patreon.com/posts/ten-tasks-for-of-37281389

You can find the first episode here – https://fionadobson.com/jensen-and-the-lady-of-the-manor/

The Stories Your Mother Never Told You.

There are stories which we choose not to share, for one reason or another. Perhaps it is related to shame or embarrassment. Or maybe we just hold them so dear, that in sharing them they would become devalued.

A friend of mine recently acquired a rather unusual collection of note books which I feel sure you will be delighted to read. He was an elderly man, I will not give very many details, as I would not wish to identify him in any way.

Wrapped in brown paper, of the sort people used for parcels many years ago, these note books were dusty hand written relics. I can well imagine them being tossed out with the trash when someone moved house, or recycled along with old copies of magazines when clearing out a loft or basement.

My friend explained that they had been among some personal papers found in a house that was being sold. The contents of these papers were at first a mystery, then quite surprising – and ultimately quite shocking.

I am thrilled to release these notes in their original sordid and salacious form. They are available to all my Seahorse members – through my Patreon Pages. Be sure to sign up to my Patrion and enjoy these extraordinary documents.

Today is likely to be one of the hottest days of summer.

Isn’t it wonderful to enjoy the sun on a day like this. Just remember that while you get into that mini skirt, you should also be very careful not to get too much sun.

It’s a great idea to carry a bottle of water, some sunscreen and at the start and end of your crossdressing day be sure to use some aloe based mopisturizer. There’s a few listed below.

Also, be smart – don’t go to restaurants or crowded public places. There’s a lot of Covidiots out there. Being in the great outdoors and socially distanced is how we’re going to get through this.

🙂

Fiona

Max’s Premature Ejaculation.

There was a steady stream of water falling between Ali, my Syrian gardener’s legs.

“Ali,” I said. “Would you mind telling me what you’re doing?”

“Ah, madam. I’m watching Max’s premature ejaculation. He did it for his mother…”

I paused. I’ve learned that’s a good idea with Ali. I’m never quite sure if he’s serious, or just confused.

“His water hose… He’s got it hooked up to Google – that online house thing. It waters the flowers. Well, drowns them actually. It’s coming on prematurely and the water pressure’s too high.”

“I see,” I said. I decided I had better talk to that English teacher of his.

Continue reading “Max’s Premature Ejaculation.”

Being non-binary isn’t just about gender.

I think it fair to say that one of my favorite occupations after I run screaming from my office at the end of the week, is to relax and settle down for a quiet weekend on the water. This is the time when, after the gnashing of teeth and sobbing generally has subsided that I can put my feet up, watch one or two friends trying to look masculine and impressive, and lament the absence of my wife, still unaccountably travelling in Europe.

If there was a week that would drive one to a gnashing of teeth, and generally pulling one’s hair out in frustration, it was indeed the week that has just ended.  On the whole my clients at the advertising agency are a sweet and very receptive group of people. They accept my somewhat unusual approach to life, in exchange for some very sound advertising and marketing guidance for which I am grateful as it does provide me with a satisfactory income. Having said that, I despair at some of the clients. 

Continue reading “Being non-binary isn’t just about gender.”

Auntie Kittie is at it again.

As Gerald comes to camp in her back garden, dating sites sheffield is up to her old tricks. Will he manage to figure out where to sleep? Is he going to be ok in his tent, and will Auntie Kittie help him get it up?

You can find out in the latest edition of Auntie Kittie’s Diary on my Patreon today.

Become a Patron!