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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Do you know your eyeliner from your lip liner?

When you first grab your lip liner and use it as an eyebrow pencil you are doing nothing more than most 11 year old girls have been doing for the last forty years. Many of my members experience feelings of disappointment and failure the first time they get up close and personal with make up. As a result they feel disappointed and often quite upset. Continue reading “Do you know your eyeliner from your lip liner?”

Does this nail gun make my hands look fat?

Just the other day I was helping my friend Sylvester do some alterations in a friend’s apartment. I’d just got out of the nail salon, and as I looked at the claret polish on my nails I couldn’t help feeling it clashed with the De Walt yellow of the nail gun.

This put me in mind of something I’d been meaning to write for a while. Those of us who love to crossdress often don’t feel quite at home with our designated gender. Just because we’re walking around with nine inches (give me a break: ed) of male genitalia between our legs, doesn’t mean we have to like the color blue, chewing tobacco and driving a truck which has been ‘lifted’. More likely we feel confused by these ideas and find them uncomfortable, realizing we’re not quite the same as our brother, the jock.

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Crossdressing in plain sight.

Many of my lovely members are unable to dress as frequently as they would wish, nor as overtly as some of us do. As a result I sat down with Bernard my photographer, and went back through my photo albums to look at ideas that were likely to succeed for those whose family life prevents them from indulging the way I so often do.

“Oh Fiona,” he mused as we looked at images from across the years, “you really do like to do it at every opportunity, don’t you!”

“I’m sorry, Bernard?” I said reproachfully.

“Oh, I’m sorry, I didn’t mean…”

“I should hope you didn’t!” Bernard needs to be chided from time to time. It keeps him in his place, and makes sure he remains attentive.

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Fitting crossdressing into a committed marriage.

Many of my crossdressing friends tell me that they feel confused and often afraid about continuing to crossdress within their marriage. In many cases they feel uncomfortable about where it may lead and guilty about these desires.

There’s a struggle that takes place trying to justify the idea of dressing, and the guilt of doing so and hiding the fact. On the one hand there’s a desire to be open and honest with a spouse, on the other the fear of misunderstanding, or even the thought that simply crossdressing may lead to infidelity. Well, before we go much further let’s dispel a few myths.

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Understanding Crossdressing

Many people feel awkward about crossdressing. They find it hard to share the experience, or tell a partner. And yet, they still derive great pleasure from the process. Today we’re going to look at that more closely.

Like most people, when we do things we need to do, we feel the way we need to feel. We are satisfying a basic need. When one thinks of it like this, its much easier to release any ideas of shame or awkwardness. It’s not something we need to do every day or all day – but something we enjoy at a moment of our choice.

Once we’ve got to that point it becomes a matter of finding a way to satisfy this harmless and basic need, in a way that doesn’t upset others. Like many things in life it’s a choice how we do this – very publicly or in a discrete and private setting.

We all compartmentalise our lives to some degree. We don’t necessarily choose to share our family life with colleagues and friends at work. Going on a family holiday and finding yourself in a resort one room from your boss and her alcoholic husband, may not be your ideal view of how to enjoy a vacation. In much the same way, compartmentalising that part of your life when you choose to slip into a sexy little black dress and enjoy a glass of wine is a perfectly reasonable thing to do.

Choosing who is part of this aspect of your life is a challenge. Just as some people may never understand your spiritual views, some will simply never understand that you enjoy dressing. That’s actually ok. You simply need not invite them to that part of who you are, in much the same way as they don’t invite you to their church.

In the end, choosing not to judge others and not giving them the opportunity to judge you, is a calm and safe path. Careful management of your CD life is a skill you will learn the easy way or the hard way. You simply cannot expect everyone to understand it. There’s no problem with that if you carefully compartmentalise your life, and allow yourself to discretely develop your abilities in safe and joyful ways. It’s likely you cannot suppress this part of who you are any more than you can change the color of your skin, or your blood type. So, you might as well get used to handling it carefully, thoughtfully, and allow yourself to find happiness in this aspect of who you are.

It’s nothing to be ashamed of, and it can bring you great happiness. Much of your experience crossdressing is dictated by how you do it. One way or another, you’ll find a way.


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Exploring Identity – Part 1

Identity is something that’s always fascinated me. When I was a child I would often play games which involved some aspect of role play. These are not only formative experiences, but also experiments in finding out exactly who we are.

When Sebastian, my personal trainer selects his ludicrous spandex shorts from his closet he is making a statement about who he is. The same can be said for Sylvester, pulling on his leather biker pants. In Sylvester’s case he has a series of tattoos, so even without them he looks hard and is making a statement even with his skin. In his youth Sylvester had been a roadie with a band, and was pretty wild. His whole approach to life reflects his identity. I think that’s true of most of us.

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Step by step guide to bringing a friend into your crossdressing.

Many women love the idea of being with a crossdresser, but how do you approach the subject and introduce a friend to the idea of helping you crossdress? In this part of The Premium Program we look at strategies for engaging our friends or acquaintances in a safe and discrete manner.

I look at the idea of crossdressing services, and the use of a mistress, and the advantages of connecting with a friend, and techniques for doing so. Many crossdressers end up being surprised by how many women love to be with a person who is secure enough to move across gender lines and enjoy crossdressing. And some find it simply irresistable!

Go to the Premium Content piece HERE.