Breaking the cycle of buying and throwing out clothes.

I remember pulling into a remote gas station on an empty road and thinking I was probably the only customer they had seen that day. In a plastic bag beside me was a pair of tights, some cheap panties and a bra that didn’t really fit.

I knew they had to go. I had been wearing the items, hurriedly bought as I’d made my way across the state on a business trip, when I was in my hotel room. After all, no one could possibly find out about this little pecadillo of mine, and what could be nicer than indulging this desire on a business trip in the middle of nowhere. But now that trip was over and it was time to dump out the evidence. This place looked safe enough, remote and overlooked by all but those who had to be here.

The gas station attendant was inside their little shop, watching something on the TV. I got out of the car and filled the tank, glancing at the trash can on the forecourt. If I dumped the clothes here they would likely go unnoticed. After all, who sorts through their trash at a gas station. No one would know I was disposing of the clothes I’d been wearing just a few hours ago. No one would guess that I was a crossdresser. After checking both ways up and down the lonely highway, I reached into the car and hurriedly tossed the plastic bag into the half full trash.

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Crossdressing, divorce and death.

Crossdressing, divorce and death.

I was remarking to Bernard, my photographer, recently that there seems to be a curious link between crossdressing, divorce and death. We were returning from a photoshoot for a client with a well known fashion business, having photographed the new Spring Collection in anticipation of next years marketing.

“I’ve never been divorced,” said Bernard. “Marriage is one institution I have not had the pleasure of enjoying.”

I glanced at him as we moved slowly through the city traffic. I tried to see if he was being sarcastic.

“Well, the term ‘enjoyed’ is not the first that springs to mind,” I said.

“Is your wife back from her trip yet? Where was it, again?”

“Kalamazoo. Or Katmandu. One of those places.” I replied a little testily. “There really are a remarkable number of my members who seem to return to their love of crossdressing following divorce.  I wonder why that is,” I said.

“Well,” said Bernard, “I suppose following divorce in middle age one is forced to re-evaluate things. You know, be a little introspective.”

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Let’s talk about breasts.

There’s not much doubt that the idea of having breasts is hugely appealing to any crossdresser. The question of whether or not we want them 24/7 is something very different. However, there are doubtless moments where a great rack would be very appealing.

So what really is the benefit? It’s tempting to think it is purely aesthetic. Well, it’s not.  As I sat in The Junction in Vancouver recently with some friends, 36 D’s pointing proudly at Jake behind the bar, I couldn’t help noticing that a large part of why I was enjoying myself so much that night was to do with not how I looked, but how I felt. The presence of a full chest, even below an Aran sweater, felt absolutely correct.

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Sailing on a gender fluid sea.

I enjoy sailing. More than that, I love sailing. Sometimes I will take Sebastian out and we’ll race 16 footers at a local club, and we do pretty well. Other times I just want to mess about on the water, just being me. And that means probably dressing in something mildly effeminate which, when viewed from a distance, you’d never know what gender I might be.

There’s something fundamentally genuine about the elemental connection with wind and water, and this strangely indeterminate person between the two. Regardless of gender, how one acts with sail and rudder will result in something beautiful. The wind has no gender bias. The wider world, however is not so generously democratic.

I have noticed from many of my members that there are definitely days in which they are more inclined to be feminine than masculine. For many, it’s not even a question of ‘days’. It’s a matter of situations.

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The Pink Escort

I lived in Johannesburg in South Africa for years. It was toward the end of the apartheid era, and was still a very conservative society.

Nearby there was a mechanics workshop. One of the mechanics working there was a quiet young man who, it transpired was gay. I didn’t know when first I met him, but when he showed up at work one day in a tricked out pink Ford Escort with nitrous and wide wheels it was pretty clear he was making a statement you couldn’t miss. The Escort was so overtly ‘flamboyant’ that the community rapidly realised this particular mechanic was as queer as a 9 bob note, to borrow a British expression.

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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.

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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.

😊

Fiona

The French Engineer

I remember a hot morning in Johannesburg, at Jan Smut’s Airport (now renamed to O. R. Tambo International Airport). A small group of reporters and photographers were out on the apron, in front of one of the hangers.

The Highveldt air was still and heavy. Not a blade of the dry grass stirred on that windless morning. The sky was so blue it would make you almost sing just to look at it.

A new aircraft autopilot landing system was being demonstrated by Airbus. This was a hands off landing system, and fully automated the final approach prior to landing until it came to a halt on the runway. It was a pretty advanced piece of technology for the time.

The press boys were all grumbling about the early hour and sipping coffee. There was no smoking on the tarmac either. Some of the engineers from Airbus were meeting with us to talk about their innovative system and were chatting away in French in a small cluster a few yards off.

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Crossdressing – Do I have to be submissive?

I was asked a curious question by a member this week. I’d just got back from a dance class with Sylvester, my mechanic.  Admittedly going to a dance class with Sylvester is a little like taking a gorilla for tea with the Queen, but it is nothing if not entertaining.

“If I am a crossdresser, does that mean I have to be submissive?” wrote my member in an email.

“What do you think,” I asked Sylvester.

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Seasoning your corset.


Many of my members love to wear corsets.  Let’s face it, anything that helps us look 15 lbs lighter is probably a good thing. Usually the only thing that can do that is either a very unusual mirror or a large amount of alcohol.

Neither of the above options help when it comes to having a balanced view of the world. So, in the interests of good health and clarity, I am the first to encourage my members to reach for a nice corset and slip into it. 

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Crossdressing – where’s my compass?

When one first realises that there’s a little more to crossdressing than simply putting on a pair of panties, most of us start a journey without a compass. Almost inevitably we do so alone.

For many of us finding out that there is a world of gender fluidity is a revelation in itself. As we explore it further, either through online discovery or tentatively exploring alternative lifestyle in our community the first steps are laden with challenges. When something is as simple as a fetish it is easily contained and managed.  The suppression of a side of ourselves that has been trying to find expression throughout our life is likely the cause of unhappiness and probably depression. As it begins to grow stronger and we move to a point where it is no longer suppressed we start to find joy and fulfillment. However, for many of us there is no yardstick and no guideline to follow that steers us in the right direction.

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One small step for man — one giant leap for personkind.

I was chatting with a friend of mine the other day. We were discussing how hard it is to take those first few steps outside as a crossdresser.

The circumstances of these first few steps are always daunting. Regardless of whether these are taken in the confines of a drag club or stepping out into an unfamiliar environment they are likely to be a few steps that are never forgotten. But is there any way we can make it easier? And should we?

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Gender Reassignment? Maybe… but then again…

Let’s do a little exercise.  I want you just to play along with this and we’ll see where it goes.  For a moment I want you to think about a person born female, who in middle age finally qualifies for gender reassignment. They’re going to fulfill their dream of becoming male in the physiological sense. Up until this stage they’ve lived as a lesbian, with several lesbian partners.

Their work environment is quite masculine. They like that, yet they’ve struggled to find acceptance from their male colleagues.

As the date of their reassignment surgery becomes closer they excited, though they begin to notice a few things. Some of their lesbian friends, who up until this time in their life have been very supportive, begin to distance themselves.

There’s something else that starts to happen as well.  Their partner is now faced with a new type of relationship. A lesbian finding herself faced with the prospect of being in a straight relationship for the first time in her life may not respond very positively to the prospect. The partner doesn’t even find men attractive or very pleasant to be around.

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Help, I can’t find anyone to dress with.

It’s a common problem. You have a healthy desire to explore gender alternatives but neither the experience nor confidence in the process to do it alone.

In this situation instead of the joy of the journey many people find themselves feeling guilty and ashamed. Where’s the fun in that? A part of them which should be celebrated is instead suppressed.

It doesn’t have to be that way.

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