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.
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.
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?”
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.
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.”
At the time of writing we are in the midst of a Corona Virus
lockdown. We’re 8 weeks into it, here in
Vancouver, and most of us have not seen many people throughout this period. For some it’s been a period of reflection,
and a chance to rethink many of the things we have formerly taken for granted.
Many of us have struggled with the idea of how we identify
with genders. This is nothing new and is a confusing and troubling subject that
is often hard to discuss. I’ve said many times that we shouldn’t concern ourselves
with gender labels, or for that matter sexuality labels. My experience is that
they’re confusing, mean different things to different people, and really don’t
serve us well. They may serve those who wish to judge us, or shove us into a pigeon
hole – a prospect that doesn’t seem either appealing or comfortable – but exactly
how does that serve us?
Yet there is always that question, “what am I?” Am I ‘trans’, or ‘gender fluid’ or some other
label that helps me understand myself. What are the boundaries here and where
do I fit?
My constant mantra here is not to judge others, nor allow
their judgement to hurt you. Placing a label is doubtless a form of judgement. While
dropping judgement is a lofty goal it’s a very solid one to have in mind. I try
to practice it, but I could probably try a little harder at times. When someone
cuts me off as I cycle to the store, I may pass judgement and express it with
my middle finger, and I am the first to acknowledge this doesn’t really further
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.
I am often asked by my members how they can hope to find a
woman who will dress them. Many times, I tell them, they’ve probably already
done so. They just don’t really know how
to identify them, or how to talk to them.
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
“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,”
“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.”
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.
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.
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.
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.
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.
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.
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.
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.