How crossdressing can change the world.

Fiona Dobson
3 min readJul 4, 2022

I was sitting in my kitchen this morning, a skillet sizzling on the hob spilling delightful aromas out into the garden, when I heard the sound of Sylvester’s chopper drawing into my driveway. Sensing the presence of sausage he often unaccountably appears. Now, the same could be said of some of my gurlfriends, but that really is another story.

Arriving just as I was about to pour the coffee, Sylvester showed up with his niece, a glorious young creature of thirteen.

“Fiona, this is Anastasia,” he said as he entered. “She’s heard so much about you, she said she’d like to join

me on my morning ride and drop by and say hello.”

“Well, hello Anastasia,” I said, and at that point I’m going to ask you to imagine pressing the pause button. Yes, freeze reality for a moment and ask yourself what would likely come next in this dialogue.

Typically I would say something about how pretty Sylvester’s niece is. Or possibly, something about how it must be fun to ride on a man’s chopper — and right now I’ll ask you to get your mind out of the gutter.

But today, I’d like to ask you to do something very special for me — and yes, it has everything to do with crossdressing. I’d like you to imagine how the conversation might go if it were to avoid gender preconceptions, and prejudices. In other words, instead of saying ‘what a pretty name’, for a girl, why don’t we choose to admire the person — free of gender.

You’re likely going to find it’s not easy to do so. If you’re like me (and I have sympathy for anyone in that boat), you’ve been brought up with preconceptions about gender drummed into you. And at this point many people will be groaning and wondering if they should continue reading. But just bare with me a moment.

The only reason you have reservations about wandering down the street in a skirt is because you’ve been taught to have those reservations. They are (sadly) societal norms. And with each generation we perpetuate them. They’ve worked for the last 5000 years, after all. Sure, there’s been a few hiccoughs, along the way (no votes for women, pay inequality and sexual and emotional abuse) but apart from that… Oh yes, and the fact that it makes us feel ashamed of wearing make up and panties.

Fiona Dobson

The crossdressing blog you’ll love even if you’ve never tried your sister’s panties.