New skirt/New life

Charlotte bought me a new skirt one the weekend. I adore the skirt. It was the manner in which it was bought which was so humiliating.

Here it is...

We were in Selfridges (London) browsing for clothes. Charlotte often asks me my opinion on clothes, usually for her.

This time she lifted the skirt on the hanger, and held it up to my waist.

Then she said, in a normal speaker voice, but chuckling, "What does my sissy think of this?"

I just turned bright red, and Charlotte said, "It's your length. It'd look cute on you. Why don't you try it on?"

At the same time a shop assistant approached, looked at us both (Charlotte was still holding the skirt up against my waist) and asked if she could help.

She looked at me, looked at Charlotte, and you could see the light bulb switch on in her head by the change in expression. Now I've never seen a shop assistant with a bigger grin on her face. Ever.

And instead of saying no, Charlotte simply replies, deadpan "What do you think of this skirt on her?"

At this point I'm practically dying of embarrassment. Her?

The assistant replied, with an enormous smile and a giggle, "It's obviously her length. Add a pair of heels and a pink turtle-neck and she'd be ready to go! Do you know her size?"

At this point the assistant took the skirt from Charlotte, and held it up against my waist herself. This was all in the middle of the shop (although it was quiet).

"Yes", Charlotte replied. "She's a 10 in skirts, and we'll take it. Thank you".

"Cute", the assistant said, as she removed the skirt from my waist and looked at me, smiling. "Follow me".

We followed her to the checkout, Charlotte paid, and the sales assistant handed my the skirt, grinning from ear to ear. "Enjoy honey!"

With that we made a sharp exit, Charlotte with a massive grin on her face, me red as a beetroot.

So, what happened was humiliating enough, right? But what was even worse is what this means for my future, and how feminine I must look to everyone else now.

I mean, the sales assistant was clearly amused. But she hardly questioned whether Charlotte was joking. She took one look at me, and assumed Charlotte was completely serious, even if the situation was funny to her.

And I can only summarize..to the sales assistant, I look like the kind of guy/girl who would look good in that skirt. I look like the kind of guy/girl who would enjoy wearing that skirt. When she looked at me, she didn't see 'guy'.

She saw 'sissy'. She saw 'girl'.

My life is changing beyond recognition.

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The post-script to this story of humiliation, is that I spent the rest of the day in my new skirt, a pink turtle-neck (borrowed from Charlotte), and a black pair of mules (low heeled).

And the truth is...I like the skirt so much, it was worth the humiliation.

That's how much of a sissy girl I've become.

Which leads me to think...if I'm such a sissy, where does this leave Charlotte and her future...? While she actively pushes my transition to sissy/girl, I can no longer help thinking I'm no longer the man of her dreams.

What if, while I slowly turn into a beautiful, attractive, pretty woman, like this...

Charlotte realizes what she really wants is a real guy, like this...

And as I become more feminine...moving deeper into womanhood, which will I need? Which will I want?

Thoughts?