Tuesday, August 6, 2019

Skylar's Diary - Day 10

Dear Diary, today I had to conquer another obstacle, but first things first. As I promised, today I will show you the outfit I bought yesterday. I wore it when Riley came. I chose a black outfit, which I think is the coolest color. I wore a simple cotton t-shirt with long sleeves and a wide V-neck. The t-shirt was on the short side. The skirt was the coolest thing, even if it was a skirt, but it had a black leather belt with metal rings all the way around, and also a metal chain. Underneath I wore black boyshorts panties (at Riley’s suggestion yesterday). I admit it, it's girl's underwear, but that's hardly noticeable. Besides, it was a logical combination. This outfit is probably not really my style, but I did feel comfortable in it. I just have to keep getting used to wearing a skirt.


Riley saw that I felt reasonably at ease, and she was happy about that. After half an hour she asked me to make some tea. "Of course," I said.

I went to the kitchen, and suddenly I hear:
"Hey, Skylar."

My mom. My mom is home. I just hadn't thought of that. And there I am in my cool girl's outfit. I didn't know what to do.

"What a cool skirt that is."

Think fast. What did Riley say yesterday? "Act normal. Be nice. Show confidence."

"Oh thank you. I chose that myself."

Yes, that's the best I could think of. As if it's all my choice. I may have seemed relaxed, but there was a lot going on in my head. Now my mom has also seen me in a girl's skirt. On the other hand, she knows about it, of course, but still...

In the meantime, Riley had also come to the kitchen.

"You know what, shall we have tea together?"

No, I thought, no way, but before I could say anything, mom said "I'd love to."

"Shall we sit here at the table?", I said quickly. Because if we were sitting at the table, I thought, I could hide my legs underneath it.

"Oh no, let's go to the living room. It's much more comfortable in the couch," said mom.

"And then we'll see your outfit better, Skylar." That was Riley. She did this on purpose, for she could not suppress her smile. She loves to tease me.

The first few minutes in the couch were very uncomfortable. Sitting with a short skirt in a low couch is a challenge. You have to be careful how you sit. Either I had to keep my legs together or I had to cross them. And pulling up my legs was not an option. The freedom offered by a skirt seems to come with a few restrictions. This is probably what Riley also meant by body awareness.

But after a while I wasn't concerned about it anymore, and I was involved in the conversation… which was very relaxed. We actually talked about very common things. And not about my problems, not about my program, not about my clothes. At one point I was no longer aware that I was wearing a skirt.

That's what I told Riley afterwards. "You see," she said, "after a while you get used to it."

"That may be," I said, "but I'm not going out in a skirt."

"Not if you don't want to."

Well, that's clearly settled then.

"Oh yes, then there's something else," said Riley.

"What then?"

"I also have a present for you."

"Really? For me?"

"Yes, here it is."

She gave me a package, and I opened it. It was a nightie. Pink. What did you expect?


"Come on, put it on."

Of course I had hoped for something else, but Riley is Riley. Because I like her, I didn't want to disappoint her. I put it on. What immediately struck me was how soft and light it was. It was a simple pink nightgown. The real girlish thing about it are the frills at the bottom. And again I felt that conflict: the discomfort because it's girl's clothing, as opposed to the wonderful feeling you have when you're wearing it.

"Put it on tonight. And tell me tomorrow if you've slept well."

"OK," I said.

Afterwards I made a new list: who has seen me in a skirt or dress? In other words: Who knows my secret?


6 comments:

  1. i so eagerly anticipate the appearance of each in the unfolding sequence of these marvelous stories in which Skylar is encouraged and welcomed into his budding femininity by his loving mother and by his gentle and wonderfully talented guide Riley. These "fictions" give me hope that the day will come sooner than later when young boys are properly supported in exploring and claiming their natural femininity and can rejoice in becoming the sweet and lovely companions and helpmates to the women in their lives. So many of us dream of this !!! Some few of us have already realized it !!! Skylar has every natural right to her happiness in becoming an exquisitely feminine girl !!! i simply ADORE these sweet stories and can hardly wait for each new installment !!! Gratefully O O x x Laurianna Payot

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    1. You're welcome, Laurianna. However, it's not sure yet in what direction Skylar will proceed...

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  2. i know. i mean i understand that i have my own point of view and shouldn't impose it on Skylar. Still, i have finally found my own greatest happiness in embracing femininity. "Masculinity" never made any sense to me. i was simply carried along in the structures of social expectation and suppressed my innate femininity for decades. What i LOVE is that Skylar is being given a choice and that s(he) has women around him / her who are supportive of this CHOICE. Anyway, i have to dance off for the moment. Thank you !!! O O x x Laurianna

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    1. Choice is what this is all about. The choice has to be offered, and any decision will be supported.

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  3. Hello. I have been told about this blog by my friend Laurianna and I have up to now read the first ten chapters and I have enjoyed every single one very much. So thanks to Shylar for sharing his diary and to Laurianna for pointing me here.

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    1. Ooh, what a pleasant surprise to see a comment after some time. You may have noticed that I discontinued this blog after finishing Skylar's story. It's a thing on its own, and I want to keep it that way. Thanks for sending your appreciation. I hope you will enjoy the other chapters as well.

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