Remembering that this is all about timing, we’re going to move a conversation into the area of fantasies. This should not seem forced, so pick you time carefully. Don’t just say “The weather’s nice for the time of year, and by the way, what do you fantasise about?”
Wait for your moment. Approach the subject with sensitivity, and be gentle. Tell her you would love to know what she fantasises about, because you want to make her happier and to serve her sexually as well as you can.
At this stage you’re beginning to move your partner toward acting in a specific manner with you. She’s been primed, sees herself as a liberal thinking and open to intimate suggestions (after all, everybody sees her that way), and she sees herself as being in control in a liberated and powerful way.
The next step is once again a subtle progression in the direction you’re trying to go. When you’re out with your wife and she’s buying cosmetics take an interest. Ask why she likes one brand of make up over another. Be sure to have a sincere interest.
The first thing to remember here is that your going into this with a plan. You’re not just going to spring it on her, and hope for the best. Far from it. By the time the issue comes up you’re going to have laid the groundwork for this to work beautifully.
I received a lovely message this morning from one of my members, Leticia. They wrote a lovely description that I feel I should include below.
“It’s always a treat to hear from you, your stories are so clever and sexy. I am fortunate to live on the outskirts of a small town, and the road out front leads into open country, through farmland all the way to the state line, and across a river. I try to take a long walk every day, and it’s a perfect chance to practice my feminine walk, flowing with a graceful sway. I am wearing running shoes, but I don’t need high heels to swing my hips. It helps me feel like a woman.”
This reminded me of an incident many years ago. I felt it worth recounting, as sometimes we give ourselves away without even knowing it. You can see my reply below.
What a lovely picture you paint. I am so lucky to have so many wonderful members. You remind me that once, years ago, I had a friend who was studying kinesiology. They watched me walking down the street one day, before I’d really emerged as being so very gender fluid and came running along after me very excited.
“Do you know,” they said, “that you walk exactly like a woman. I can see your hips swinging and the motion you use in your gait – it’s so very feminine. I’ve not seen that so pronounced before… in a man. I mean, it’s sort of unusual.”
My acquaintance was suddenly aware that their enthusiasm for their study and their observation were a little inappropriate, and a moment later they felt quite awkward. I don’t think they realised that they’d seen something that was developing and growing within me and that it would become quite impossible to suppress. It was most enlightening, though I don’t think they really realised just how very deeply ingrained that characteristic was.
Sometimes who and what we are emerges in ways we least expect. I have learned not to fight it, but to just allow it to happen. I hope you do too.
You’ll see that throughout my website and the contents of my Patreon I talk about accepting yourself as you are, and creating yourself as you desire. Sometimes we can’t really help it.
Have you experienced similar moments of revelation? Be sure to tell me about them in the comments below.
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.”
So many of my friends privately confide in me that they’ve always wanted to crossdress, but just never really knew where to start. It’s not the clothes that were the problem, it was how to think about gender.
I generally suggest they listen to this talk to help get their heads in the right place. After all, crossdressing is more about what’s between your ears than what’s between your legs.
Like many of us, I never got to talk to my parents about things like sexuality and transgender topics. Both of my parents would have been mortified to have the subject raised over the Sunday roast. And then they died.
To be fair, I don’t think either of them were quite ready to talk about such topics. They were born in the 1930’s and these are subjects that simply weren’t on the agenda during their lifetime. That is not to say that they don’t have a contribution to make on the subject of ‘Pronouns’.
My mother, a girdle wearing statuesque woman of conservative English values, held one thing above all others. Politeness to others. Had I told her that a guest in our house identified as a punk rock hamster, then out of deference to the wishes of a guest we would have had to refer to the hamster at the table with unquestionable politeness and respect. I suspect that had Stalin or Mao showed up in our English parlour for tea, we would be expected to hold out the chair, sit after they had taken their place and make polite conversation about the intemperate weather and the promising outlook for the turnip crop this year.
Raising the subject of genocide, persecution of minorities or (God forbid) the forced labor camp deaths of homosexual prisoners would have been considered bad form and may have resulted in a reluctance to return for tea another time. Admittedly this exact scenario never played out in our home counties home, but I think you can see where I am going with this.
Equally, it can come as no surprise that when my father watched a documentary about German prisoners of war – a small number of which escaped from a prison camp in Northern England in 1944 – he stared at the television screen with visible disdain. For the Waffen SS officers to have dug a tunnel out of the confines of a prison with a desert spoon merited their being sentenced to hang immediately, if for no better reason than to do so using a desert spoon, before the use of main course cutlery, was practically a crime against humanity. Well, English humanity, at least.
So, I can say with absolute certainty that had someone come to the house and mentioned that their chosen pronoun was ‘they’, then the matter was settled. They would be a ‘they’ from that moment on.
As archaic as it may seem, this concept holds true as well today as it did in their lives. Whether straight, gay or any shade between, their principal object was to be polite and treat people with respect. To date I have yet to come across a system that improves on this simple behaviour. After all, when we do behave in this manner people do generally treat us with respect in return.
Now, I have to put the tea on. I’m expecting Kim Jong-un any moment. The supreme leader wouldn’t like it if I failed to warm the pot before he arrives.
When I started My Little Black Book four years ago I was surprised by how many of my members immediately joined the system. It’s a very simple method of connecting with other crossdressers and admirers, and to be honest it’s a pretty bare bones type of tool.
I help many people get in touch with their feminine side, and many of them want to reach out to others, both for support and friendship. I often hear that people struggle to connect with crossdressers, and that crossdressers struggle to meet admirers – both male and female. It seems to me this is a problem in search of a simple solution. So I built one.
I was a little concerned that the simplicity of the system would not appeal to people used to online dating apps that are pretty sophisticated. My intention was to keep costs minimal, but more importantly put the members in control. The idea was that people set up an email that they felt safely put all correspondence in one place, and then list themselves in My Little Black Book. Members could then use that email to reach out to others, and to have others connect with them.
Very soon it turned out that people loved the fact that it was so very simple, which has become the single most important part of the system. Now we have members from all over the world talking to each other, and enjoying correspondence from near and far. It’s proved a great success. People were even connecting and sharing group holidays.
What happens when someone is outed? Lenni and Jules discuss the challenges of being ‘outed’ as a crossdresser, or transgender – intentionally or otherwise. Be sure to participate with the continuing discussion via Whatsapp here: https://fionadobson.com/join-our-elit…