Let’s go back to basics.

So many of my members have spent years suppressing their desire to dress, and only once it is indulged do they find a sense of joyfulness. Sometimes this is accompanied by feelings of shame and guilt, and it all seems very confusing.

Suppressing these feeling can result in feelings of frustration and depression. Often members report that they never understood why they felt so lost, until they began to allow this side of themselves to emerge.  Prior to embracing their gender fluidity they report feeling lost and fail to understand ‘why is this happening to me’?

For the vast majority of my members it’s about easing into a more comfortable place on the gender spectrum. For some it may be as simple as becoming just a little more androgynous in the way you dress and think. Others will of course find they do want to allow themselves to become far more feminine. I’ve certainly found that many people now go as far as using HRT (Hormone Replacement Therapy), either herbal or pharmaceutical, without any desire to go for full surgery.

In the end my Premium Program is created to help you find the appropriate place on the gender spectrum that will work for you and fits with your lifestyle. There’s an expression in the LGBTQ community, which originated in the gay and lesbian world, but is very applicable to those of us who consider ourselves to be gender fluid.

“We don’t raise our young. Instead they have to find us.”

Some of us take quite a while to find our tribe. This can take the form of people in your own community or even systems like my Elite Whatsapp Group – where many people find support and friendship. Hopefully we get there in the end. That’s when things start to make a little more sense.


Shove it in my trunk!

“Shove that shaft in my trunk,” I said to Sylvester, who’d asked me to give him a ride home after work.

He’s a wonderful mechanic, always with a tool in his hand. But I digress. I felt I would write and tell you about the wonderful things we’ve got planned for Mexico.

So many of my members struggle to find a way to dress discretely and safely. I am thrilled to be offering the escape to Mexico we have planned for January.

I hear so many stories of members unable to dress and relax. Many of my members are not comfortable going out of the house dressed. Others fear they may not pass as well as they’d like.  Now, imagine a situation where you could dress. You could ask someone for some help and advice. You could even learn about make up, and enjoy a night out without the worry of someone bumping into you. That sounds like a pretty good day.

Well, our team at the Fiona Dobson Crossdressing Conference can help you do exactly that – but for four days and in the spectacular Miramar Hotel in Puerto Vallarta. Join us on this escape and take that giant step that every crossdresser wants. This trip will help you feel confident crossdressing. In unpressured and non judgemental surroundings enjoy the feeling of wearing what you wish, and doing what you want.

You’ll be with a small group of people, likely just like you, in a private setting.  If you’ve ever had to hide your dressing, this retreat will be relaxing and rejuvenating. Get more information HERE.

By the way, if you’ve never read it, you may enjoy my ongoing series Clothes Maketh The Man. It’s in it’s 37th episode at present.

Have a great week.


What if… A look at the idea of transition.

I received a very touching email from one of my valued members this morning. I feel I should share it for several reasons.  I will quote it, and then talk a little more about it.

“Hi Fiona,

From the first time I felt the urge to express my feminine side as a teenager I have often wondered if it was an escape route for stress, though for me I believed it was a sign of something deeper. From the age of 5 I can remember admiring female clothes particularly the tight waist full skirted dresses of the sixties. This urge was looked upon with disgust by my family, now I have lost both my parents I am free to dress when ever I wanted however I realised I wanted to take it further to see how I felt about it.

During those years I came to realise that for me sex had to be lesbian based to get any personal pleasure, I preferred to please my partner in preference to getting pleasure. Looking back to when I was 5 i can remember hoping our neighbour, a lovely lady would, invite me to go under her skirts to adjust her suspenders to keep her stockings taught, so you see I always wanted to give pleasure to women – of course it never happened.

Continue reading “What if… A look at the idea of transition.”

The Stories Your Mother Never Told You. Part 6.

In a tattered journal given to me by one of my clients, I came across the following account which you may find of special interest. It was clearly written describing a time when my visitor was little more than an infant. You will see that we’ve named him Billy junior, to help keep things straight. I would guess that the diary entries are from the late 1950’s, judging by the content and condition of the journal.

July 26th.

I drove across town this evening to Vince Miller’s place. Funny being there after all these years. I remember his 6th birthday party. The swing on the lawn. But tonight was something different. He asked me to do a little favor a few weeks ago. I’ll tell you about it.

Continue reading “The Stories Your Mother Never Told You. Part 6.”

Broom Broom Bitches!

What a surprise Lenni and Jules had when they fell over these strapping curling team members earlier today. As you likely know our Vancouver members are often getting into trouble in one form or another.

“I just came down here hoping to score,” said Lenni, a keen athlete, in her own way. “I love to help out the team. Keeping score is just one small way I can provide a supportive hand.”

Jules spotted the team name and couldn’t resist. The team plays at The Hillcrest Centre, an Olympic venue in Vancouver.

“I was impressed by their strength, and the length of the shaft,” said Jules, admiring one of the brooms.

We wish the Broom Broom Bitches a great season curling and look forward to enjoying more of the Whister Brewing Company’s Chestnut Ale.


Your hairdresser may be your new best friend.

While so many crossdressing members love to wear lingerie and sometimes costumes, such as a fetching schoolgirl outfit, these clothes can sometimes prove an impediment in the workplace. In fact, for many of us, finding a way of expressing the feminine side of who we are on a day to day basis is a source of some frustration.

However, there is a way to incorporate a slightly more subtle expression of femininity that can be both stylish and fun, while not being so extreme that those around you might take issue with it. I am of course referring to how you arrange your hair. With this in mind I decided to have a chat with Vidal, my hair dresser. He’s a very strange man, I have to say.

He has a shop on Rue De Jenna, or the ‘main drag’, as Sylvester calls it.  With his heavy German accent and smoldering looks, having Vidal behind me running his fingers through my hair is a treat I always enjoy. Funnily enough, his name is Vidal Dresser. Now, I know you won’t believe this but in Berlin, where he’s from that really would make him Herr Dresser. Actually it would be ‘die Friseuse’ but you get the idea.

I have to be a little careful, with Vidal. He’s made more than one inappropriate suggestion about getting me in his chair late at night. Naturally I told him to shut his schnitzel hole and get on with the job! I do just love Berliners. 

To be fair, he does take time to work on my hair in a way that keeps me happy. Most men’s barbers hack at hair not unlike Ali using a weed whacker in the arboretum. Since Ali declared a jihad on the weeds recently and he’s cleared most of the underbrush. Unfortunately that’s what most hair dressers seem focused on.

Vidal assures me that finding a hairstyle that is a blend of androgynous and feminine style is not as difficult as one might have thought. This has the advantage of making a wig unnecessary. It’s very liberating to find a style that works, and then to adapt it so that you can wear it dressed, or when not dressing at all.

So, this week I’m going to suggest you check out my Pinterest board with a few hairstyles here –

https://www.pinterest.ca/fionadobson22/hair/  – and ask you to start thinking about the idea of working toward a more feminine hair style. Eventually you’ll want a lady’s hair stylist to start working on your hair. Have an image in mind, preferably so you can show the hairdresser. Yes, it’s going to be a woman in the image, but don’t worry, most hairdressers are quite used to being asked for this sort of thing. Many look forward to the challenge of working on a man’s hair, with a more feminine style.

Vidal assures me that men usually have a hair cut, and that’s it. It’s done. In the case of feminine hair styles the process is rather different. It can take a few months to develop precisely the right style. Given about a month between appointments, it can take three months to develop the style you’re looking for. In my case, Vidal uses a razor cut to style my hair in a manner that could be either masculine or feminine. It takes three or four months, with a cut every month, to create the look I am going for. This has the advantage of allowing you to adopt a slow change, which people around you will find easier to accept than just appearing one day with a massively changed look. Gradual change is always a better idea.

These are styles that can easily be switched, and won’t betray you if you’re really not very open about your dressing. Have some fun with it. After all, that’s what it’s really all about.



How crossdressing can change the world.

I was sitting in my kitchen this morning, a skillet sizzling on the hob spilling delightful aromas out into the garden, when I heard the sound of Sylvester’s chopper drawing into my driveway. Sensing the presence of sausage he often unaccountably appears. Now, the same could be said of some of my gurlfriends, but that really is another story.

Arriving just as I was about to pour the coffee, Sylvester showed up with his niece, a glorious young creature of thirteen.

“Fiona, this is Anastasia,” he said as he entered. “She’s heard so much about you, she said she’d like to join

Continue reading “How crossdressing can change the world.”

Clothes Maketh The Man – Part 37

I pulled into the evening gridlock, the smell of Devina still in my head.  The way she’d towered above me, so controlled, her big eyes inspecting me had left me feeling both more unsettled about her motives and yet compelled by the undeniable feelings growing within me.

I couldn’t help but feel desire for Devina. The woman who was the architect of my own destruction and this unchained slavery which she had so skillfully imposed upon me.  I knew that, despite her releasing me from the abominable chastity device, after I had done as she had told me, I would return and lock myself up as she had instructed.

I would drive to Mandy, my girlfriend. There I would, as Devina had instructed me, ‘do my duty’ by Mandy and then I would return. Like a slave returning to their master. And I would be grateful.

Now, for those of you who have experienced neither chastity nor the powerful draw of a dominant partner this may all seem rather strange. However, there’s no doubt there is a peculiar motivation that forces us to do things that seem counter intuitive to the uninitiated. It has to be said though, the wife who returns to the husband that abuses her, the person that day after day goes to a job they despise, these are equally baffling, though psychologists will offer plausible explanations. Yet here I found myself, consciously considering that I was so firmly bound by these chains of desire that I had absolutely no choice but to do as Devina instructed.  Could this be something like a case of Stockholm syndrome? 

The image of Devina, tall and strong toying with me came back to my mind. It was intoxicating. Her laugh, her power and her control. I find it confusing and yet compelling. I wanted to obey.

The traffic was static.  My instructions were clear. Go and satisfy Mandy. How Devina knew this what was needed I did not know, nor did I much care. My instructions were clear.  I tapped out a text message in the frozen traffic and told Mandy I would be there as soon as traffic allowed. I guessed this would come as a surprise to her, but a reply came moments later.

Continue reading “Clothes Maketh The Man – Part 37”

A Nightingale Sang In Berkeley Square.

Now that summer is marching down the garden path toward my back gate and fall is introducing herself at the front door  I turn to ideas about putting together a new wardrobe. I was pondering this, and putting a few thoughts together on Pinterest (  https://www.pinterest.ca/fionadobson22/  ) just this morning. As I did so Sebastian came into my kitchen looking quite disturbed.

As you know, I like to think of myself as a caring soul, a sort of Florence Nightingale in yoga pants. Sacrifice and humility are my two middle names. Yes, that seems a very fitting description. I applied a little lipstick and asked Sebastian to share his deepest concerns with me.

“My sister, Rainbow, has taken off,” he said, sounding quite disturbed.

Continue reading “A Nightingale Sang In Berkeley Square.”