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Trying on a dress as a cross dresser or transgender woman

Do Maidens like to shop?
Oh yes!
And it must be a maiden thing, because Boy-me has no interest in clothes shopping at all. Zero.
But Girl-me, I actually dream about shopping for clothes. Well, lingerie mainly, but pretty clothes too.
In the real world though, it’s not so easy.
To the outside world, I’m Boy-me and do feel a bit conspicuous browsing the displays of skirts and dresses. I’m always scared people are staring at me and jumping to conclusions: “oh look a cross dresser, or do you think he’s one of those trans people?” I once overheard two girls whispering “gay”.
So shopping in the real world is mixed emotions. It’s exciting to think of buying something pretty and feminine for my inner Maiden. But scary too.
It gives me butterflies.
Over the years, I’ve bought myself various things. The pattern is: spend some time around shops trying to get the courage to go in; browse a bit; get brave enough to touch some things, look for sizes, maybe pick something off the rack to look at better; go to pay, make some lie about shopping for my girlfriend and then pretty much run away!
This is not the best way of shopping.

This trip was a bit different though.

Choosing a dress

I had decided that it would be nice to have a dress to wear. Boy-me was traveling for work and I could go to a shopping centre far from home where there was no danger of anyone I know seeing me.
Still scary though.
Butterflies.
I spent a while wandering around the shopping centre seeing what the options were. I went into five or six shops, checking out the range of dresses. Of the stores, Next had a few dresses that I thought I might like, so I went back to there.
On one wall, there was a blue, stretchy knee-length dress. As I was considering it, a woman with a daughter in her late teens/early twenties takes one from the rail to show the girl. I’m too conspicuous so I move through the shop a bit. There’s a similar style, tight and stretchy with long sleeves, stripy in red blue and black. Just above the knee I would guess. It’s roll neck and there are buttons on the cuffs. The material is ribbed and on the hanger it looks like it gathers in at the waist. It’s nice, and stretchy pull on garments are easy, you don’t have to worry about getting the wrong size like you do with something that you have to zip up. It’s certainly a contender.
Nearby is a section of kind of office wear. It’s mix and match suit jackets, skirt, trouser or shift dress. All in black or navy.
Boy-me works in an office and admires the female staff, all of whom seem to favour a shift dress like it’s the uniform of the professional girl. So I’m drawn to them. They’re plain, to the knee and right up to the neck, with a little notch at the neck line (in fact on the website it is called a notch-mech shift dress).  Only problem is the zip up the back, which means getting the right size and I really don’t know what I am.
And it’s not like I can go and try it on to find out, can I?
Can I?
I never have.
I’ve bought things in the past and been scared of facing the lady at the till.
And although I’ve dreamed of being a girl since forever, no one else has ever seen me. I am very much not “out”. I am “in”!
I’d like the dress though.

Asking to try on women’s clothing in a shop when you’re a man

The store is not busy. The mother and daughter have moved on and there are no other customers in this area. Nearby, there is a member of staff tidying a display. She’s young, pretty, wavy dark hair down to her shoulders. She’s wearing a black top and a heavily pleated bottle green skirt that is like the one on a mannequin in the window. It’s a slightly odd length, mid-calf, but I like the way it moves with all the pleats, it’s cute. She looks kind.
I go over to her.
“Excuse me” I say, nervously “would you be able to help me with sizes?”
“Of course” she smiles, and her voice is soft and kind “what is it you’re looking at?”
I lead the way back to the shift dresses.
In books when they say that my heart was pounding out of my chest, it sounds like a cliche.  Mine absolutely was!
Speaking in a low voice so no one else might overhear: “Erm, this is a little bit awkward but actually I’m shopping for myself...”. Bravest and scariest thing Maiden me has ever said!
How would she react? Gasp? Laugh in my face?
“That’s ok, do you know what size you think you are?”
Wow, she didn’t immediately hate me! She was being kind.
“Not sure,” I said, heart still racing, “I think maybe 12 or 14.”
And now in for a penny, in for a pound...
“I don’t suppose, would it be ok to try one on?”
Still expecting to be laughed at and asked to leave...
“Yes, of course. I’ll bring the dresses and I’ll walk over with you”
There are other people around the fitting rooms.
“I’ll put you in the one right down the end so you are safe on your own and I’ll wait right outside in case you need anything.”
So suddenly there I was, safely behind a door, in a fitting room with two dresses.
I removed my male clothes and held the dress against me on the hanger and looked in the mirror. I wished I’d brought girl’ underwear with me, but this hadn’t been planned, so I’d have to make do.
I unzipped the dress and took it off the hanger. Before trying something new, the moment of anticipation.
I stepped into the open dress.
One of the things that I find so enjoyable about wearing girl’s clothing is how different it feels. Pulling it up, it floats around my legs which feels nice. The other thing, is the stages of dressing. Boy clothes, you simply put on. Girl clothes have stages. Having stepped into a dress and pulling it up, you need to get the narrower waist over your hips and bottom. Then, you cover your chest and put you arms through the shoulders. This dress has small sleeves. Still not done. The final stage is to close the zip. And oh my gosh, how hard is that?! It’s nice, the feeling of the dress closing around your body, but doing it up all the way requires some kind of flexibility that I seem to lack. Are real girls able to twist their arms backwards or something?
I manage to get the 14 on. I’m sadly not a 12. Not in this anyway.
I look at myself in the mirror and I can’t quite believe it. I’m trying on a dress in a shop!
The assistant is waiting for me when I come out (back in boy clothes) and I buy the dress.
Before I leave, I take the time to thank her. To explain that I’m at the start of a journey and have never done anything like that before but that her being so kind has made it so much easier.
What a lovely kind person.
Maybe whatever sort of gender journey I’m on, it isn’t as scary as I feared.

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