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!
My goodness, if you could see what’s going on outside my window. I can hardly believe is! I’m standing here in my Christmas lingerie, and my heels, and quite shocked at what I can see going on out there!
Ali, my gardner has just told me, “It’s ok, Fiona. It’s just Sylvester and Max jacking off in the flower beds.”
Now, I know you can imagine me standing here in my flowing red silk robe, mouth open in surprise. I am staring out at the snowy Montreal scene, and everybody seems to be having a wonderful time! Oh, perhaps you should even be here!
Let me explain. I’m watching Sylvester’s muscle bound arm pumping up and down and Max, my next door neighbours 20 year old son laughing – I think he’s licking his fingers – yes, he’s spilled some Bailey’s Irish Cream on his hand, or at least I think that’s what it is. And Ali is watching, engrossed in the unfolding scene.
They’re laughing and very jolly, Sylvester’s face red with exertion, and he has a look of deep concentration. Apparently, Ali’s Smart Car slid off the drive in the snow as he pulled into the icy driveway. It slid into the flower bed, and onto a rock in the rockery. Max and Sylvester were already at my place enjoying a Christmas eve drink, and now the three of them are working away to lift the little vehicle off the rock and manhandle it back onto the drive. What Christmas excitement!
I should hurry along! Amanda, the queen of tweed will be here soon, and Bernard is coming over. My wife, sadly is travelling. She’s a slave to her job! In the meantime, we are a fun gang, all hoping that Christmas will go with a bang!
I know Sebastian wants to show me his mince pies and sausage. He has been making so many delightful treats lately.
I hope you have a lovely Christmas! Have a wonderful holiday and remember, be careful if you are driving in the snow. Otherwise you too might find yourself licking Irish cream from your fingers after jacking off in someone’s garden!
In this gentle and poignant piece of Christmas writing Mollie Blake demonstrates how well she understands the world of the crossdresser and gender fluid members of this site. I hope you enjoy it as much as I did. Incidentally, she passes on the very best fo seasons greetings to all our members. Feel free to write to her care of myself – firstname.lastname@example.org. Fiona.
“So you’re in the car now?”
“Yes,” David replied, keeping his eyes straight on the road in front of him. “The traffic’s crap even though I waited until after the rush hour.”
“Every hour’s rush hour these days. Wait until Brexit. It’ll be quiet then with no lorries delivering stuff from Europe. How will you survive without that German shampoo?” Lucy started chuckling.
“Yeah, well, I wish they’d all fuck off the damn roads right now.”
“I don’t know why you’re so impatient to get to somewhere you don’t want to be!”
“I know. Stupid, hey? I’d rather spend Christmas with you. But…well, he’ll be on his own, and I’ll feel bad about it.”
“Stop whining. You’ll be back before you know it, and we’ve got New Year’s Eve to look forward to.”
As you start talking more freely with your partner about the changed that you’re experiencing, there’s going to come a moment when you decide to move the conversation from talk to action. The best way to do this is to have a goal in mind that your partner is invested in.
When I think how often I entertain guests at my house, I am quite surprised. It seems hardly a week goes by without some sort of event or dinner here in Huckleberry Close.
Just the other day I had Ashley Baron in the hot tub. Calm down, Amber. Anyway, I’ve long felt Sylvester could help by building me an extension to my dining table, and finally he has. Now it’s so long I can get 12 people around it. One can end up losing control of the condiments and vegetables though.
“Are the carrots up your end?” I asked Bernard. I’ve had to ask Bernard, who often sits at the far end of the table if he can pass the carrots back my way on more than one occasion. Strange how those words stay in one’s head. But that’s not the main reason for this post.
When it comes to broaching the subject of how you are changing, the way we speak about our shifts is every bit as important as what we say. It’s important to address this calmly and in a well-chosen moment.
I do so love swimsuits that have that lovely high waistband. As I looked at mine hanging from the back of a chair in my garden, snow drifting down I slipped into the hot tub. A light steam seemed to rise into he chill night air, as I sat in the warm water watching the snowflakes and sipping a negroni.
I was fortunate this week to enjoying interviewing Ashley Baron, a familiar face on Tumblr and more recently Twitter. As we sat in the freezing night air, surrounded by hot water and the beautifully manicured bushes Ali, my gardener, has been so busy with, we chatted about her journey and what crossdressing has meant to her.
Ashley started dressing following a breakup with a girlfriend. She’d left some of her things, and one night curiosity overcame Ashley, and suddenly there ‘she’ was. Whilst always a little curious about reaching for a pair of panties, and exploring the idea of gender fluidity, this was her first real foray into crossdressing. At the age of 23 she discovered a world which would be a natural fit.
“I was surprised how natural it was for me,” she tells me. “I think the most unusual thing for me when I started crossdressing was realizing just how feminine I actually looked in those clothes. It really kinda shocked me, and just made me want to see how far I could push it.”
Ashley has always admired strong female characters. For her these were the role model that would steer her values and her life. A principled and genuinely authentic person, Ashley found great joy in cosplay – and emulating the characters that inspired her. Unafraid to take on a challenge she dresses provocatively and challenges herself. The character of Babydoll in Sucker Punch is one of her favorite costumes and one she pulls off with consummate skill.
When there’s a light breeze in the Quebec night, the clouds skid across the sky, and the stars break through from time to time. It’s quite lovely.
Ashley carried on, “At this point I crossdress about 90% of the time in my life, and thankfully, I’ve always had a family who supports me. It’s the same with my job. I bartend at the same place I was bartending as when I didn’t wear a bra to work!”
Ashley laughs as she adds, “My bosses are awesome. I suppose the only thing that has changed is that I make better tips in a push up bra than I ever did as a ‘normal’ bartender.”
I asked her about the way she’s become quite an online personality. She’s so cute when she blushes. Perhaps one of the most endearing aspects of Ashley is her genuine modesty.
“I have never really considered myself an online personality,” she confessed. “But i’m slowly starting to realize I might be and I seem to actually have a fan base and people who love me, and that is the most amazing feeling ever. I love that people are inspired by me! That’s such a cool aspect of what I do, that I can bring joy to other people’s lives. And as far as Tumblr goes I’m sad to see it change. Tumblr was a platform that let me express myself, and now that is being taken from me and others, and that’s disappointing to say the least.”
Now, I have to say that I was a little surprised when I noticed my neighbor Marjory and her girlfriend Amanda (my wife’s appalling friend) next door peering over the fence. Amanda, as you know, is one of the only women I know who wears tweed underwear. I believe it’s specially designed by Carhartt for her. Marjory has recently returned from a competition on the busy competitive eating circuit. Ironically she appears to be leading in the sausage division, which is beyond ironic considering she is a committed lesbian. I hurried the interview along as I knew Marjory and Amanda would be invading the hot tub shortly.
I had thought Ali had discouraged Amanda from infiltrating the garden, but he felt it was unfair to shoot her with the paintball gun so often, so I have tried to adopt a more humanitarian approach, at least over the Christmas period. It’s a little like the Christmas Truce of 1914.
I asked Ashley if she had any suggestions or advice for other crossdressers. Her reply illustrates Ashley’s very generous nature and I am quoting her verbatim.
She said, “I never want to influence too heavily people who have to make their own decisions on these things, however, I will say this: Never feel embarrassed or nervous or ashamed about who you are. We are finally (almost nearly finally) pulling away from a society that has been telling people forever that even considering crossdressing, or transitioning, or even questioning your own sexuality is a “bad/wrong/evil” thing… it’s not. It’s not a bad thing to discover who you are and ask yourself who you want to be. Never be ashamed of trying to find out who you are.”
I could not help but feel that so accurately mirrors the mantra of what we do here, in our tag line – “Accept yourself as you are, create yourself as you desire.”
This is a season to be generous, and I’d strongly suggest reaching out to her showing your support.
Finally, as Marjory and Amanda squeezed through the fence defences and came into the garden with their towels, Ashley added “There is nothing sexier than someone who is confident in themselves.”
I glanced at Amanda, wondering if there is such a thing as too much confidence. As editor of Pig and Pig Farmer I suppose it is important to have an opinion about everything, and she certain has that.
Ashley has a healthy diet avoiding fast foods, and focusing on vegetable and chicken. It’s a far cry from Marjory’s red meat based diet. As we relaxed the night become still more beautiful, and I was left thinking how Ashley really is the perfect guest. Be sure to show your appreciation HERE.
First of all, in response to the many emails that have flooded in response to last weeks multiple choice competition. The correct answer was, of course, B – ‘He didn’t use enough lubrication.’ Congratulations to Mildred of Colorado Springs for getting the right answer before anyone else on that one.
It’s been an exciting week, not least because Sylvester burst into my kitchen this morning, a giant package in his hand.
“Goodness,” I gasped. “Sylvester, what an enormous package you have!”
“It’s just arrived from Amazon,” he declared proudly. “It’s your Christmas present.”
I hardly knew where to put myself. Instead of opening it, I decided to place it beneath the Christmas tree in my living room along with several others for my friends, as we’ll all be gathering on Christmas morning to open gifts together. I do so love this time of year.
It’s a special time as we celebrate two things. The first is, of course, a season of good will to all. And the second is The Fiona Dobson Crossdressing Man Of The Year. Last year, you may remember Sarah Huckabee Sanders won, baffling medical science. So, if you have any suggestions please email them in, and the most popular ones will be put on the website for members to vote on.
If you’re enjoying the website and emails be sure to register, or commit to The Premium Program. Your $35 subscription not only gets you the great Premium Program, but also helps support our members who are unable to join the Premium Program, by allowing me to offer our free program at no cost. It feels good to support our community.
Till next time,
Don’t forget – you can always find The Fiona Dobson Playlist HERE. Put it on and enjoy a fun day!
Dr. Helen Webberley is one of very few people who have dared to stand up to an establishment that has neglected transgender patients and left them with no support for many years. For so many people, myself included, GenderGP saved my life from a time where my local Health Board wanted to leave me on an endless waiting list. GenderGP provided a wonderful and supportive service and gave me access to treatment that I needed.
On December 3rd 2018 Dr Helen Webberley was found guilty of operating an unregistered clinic for transgender patients. She was fined £12,000.
Click Here To Read Media Article
Dr. Webberley has done nothing wrong other than dare to stand against a system that wasn’t doing enough for its vulnerable patients.
Now is the time for the trans community and trans allies to come together and let Dr. Webberley know how much we support and appreciate the work that she has done for transgender patients.
We are not seeking to raise funds to cover any legal fees. Simply we are raising money specifically to say “thank you” to Dr Helen Webberley for all the life-saving support she has given the transgender community, and for the personal sacrifices she has made.
I was very suprised this week when I was visited by Sebastian’s cousin, who is visiting Montreal, from Trondheim in Norway. Arvid is a little short, bespectacled blonde young man, who is a genetic scientist and researcher.
I am always curious about such technologies and scientific developments. I remember reading a maginificent book some years ago, called The Seven Daughters of Eve, which piqued my interest.
As we chatted, I leaned over and poured Arvid’s tea. I couldn’t help noticing the way his glanced slipped to my chest, and hovered there. Now, as you likely know, I love to crossdress in a low cut sweater, and figure hugging clothes. It did seem that Arvid’s research interests may extend beyond the highly theoretical.
“Oh, Arvid,” I said. “I do love the idea of you delving into my genes. I’d so love to learn a little more about my genetic background.”
Arvid turned a deeper shade of red.
“Besides,” I simpered. “Who know’s,” I said as I leaned over and poured a little milk into his tea. “Perhaps there could be a little viking in me!”
However, that’s not the main reason I’m writing today. I did want to tell you more about the wonderful things going on at http://FionaDobson.com. We’ve got some wonderful new members in My Little Black Book. Such a great group of members looking to connect and chat.
I should also give a quick mention to my correspondent Mildred, from Colorado Springs. I just want to clarify something, Mildred. No, you do not need a password to operate a wireless bra.