Monday, July 29, 2019

Skylar's Diary - Day 3

Dear Diary. Today's session was fun, but tomorrow will be the worst day of my life. More about that later. When Riley came in she asked me where my shorts and blouse from yesterday were. Apparently I am supposed to put those clothes on before she arrives. No problem so far.


Today we experimented with nail polish. Riley had at least 10 bottles with all different colors. She said there was even one jar that was meant for men, but she didn't say which one. She asked if I had ever applied nail polish before. No, but I had no reservations about it. Riley explained to me very carefully how to do this, and I was allowed to choose the color myself.  In the end I opted for deep blue. That was not too girlish. She did my right hand (because I'm right-handed), and I did the left one. And she also suggested that I paint my toes.


It got even funnier. I saw that her nails were not painted, and then I asked if I could paint hers. She was obviously surprised, but she liked the idea. "Can I also choose the color?", I asked. "Sure," she said. And then I did each nail in a different color. LOL! She took it in a sporty way, and even promised she wouldn't remove the nail polish. Nice girl (so far).

Then she gave me an assignment, and I'm starting to understand why. "Write down at least 10 things you find typical for girls. But write them down in the first person, as if you were that girl.", she said. "Fine," I said. It was kind of weird. While writing, I saw the nail polish all the time, and I couldn't stop thinking about it. I think that was her intention. When Riley saw that my hair was hanging in my eyes (maybe I should have my hair cut again), she put a pin in my hair. At first I thought, "What are you doing now?", but I have to admit that it was easier to write.

Here's the list I made:

We just went over this list, but Riley said we'd come back to it later. But then it happened. She wanted to play one more game, "truth or dare". I was allowed to start. Well, I told her to wear sandals tomorrow, and walk around the city like that, with her 10-colored toes. "No problem," she said. Darn it, I really thought she wouldn't dare. And then it was her turn.

"And you're coming with me, with your painted nails, and wearing the clothes you're wearing now."

"No way."

"Well, then you lose the game."

"Don't I get a second chance?"

"OK, we're going somewhere where no one will know you anyway, and I'll be with you all the time."

I pondered for a moment. I hate losing games, and I'd find a way to look respectable after all. So eventually I agreed. "Fine," she said, "I'll see you tomorrow."

She left, and more and more I realized that I'm in trouble. I still don't know how to get out of this. I think I'm not going to sleep well this night.

To: Skylar's Diary - Day 4

3 comments:

  1. Dear ukkiezorro, i feel that it is so wonderful that it is Skylar's mother who has sent Riley as a femininity coach to coax him into the natural pleasures of femininity . . . i adored Skylar's list of girly qualities and am so looking forward to Skylar exploring this list as a map into her future as a delightful girl. We do so need the love of our mothers and the guidance of women and girls to become our exquisitely feminine selves. ukkiezorro's writings are such a beautiful and important affirmation of femininity that is truly natural for boys. i believe that such writing is a significant contribution to a beautiful feminine future for so many of us !!! With my warmest heart's warmest gratitude O O x x Laurianna Payot

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    1. Thanks again, Laurianna, for your very very kind words. It's so encouraging to read that these stories give support to many. And I'm a bit jealous of the rich vocabulary you adopt in your posts and comments.
      Tomorrow you'll learn how the outing to the city went.

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  2. Oh Ukkiezorro, Laurianna is so right on how you have Skylar so deftly out thought and firmly handled on the sweetie's proper transformation from once false boisterous 'manhood' into demure and yielding ladylike behavior so more befitting what males actually are beneath their false 'masculinity'

    Adore the quote of Skylar's demaling assignment: "Write down at least 10 things you find typical for girls. But write them down in the first person, as if you were that girl.", She said.

    Oh how clever in that Riley was well aware future members of Her Superior Sex are at some time NEVER going to hav to make such sissified self-admission as tomorrow's 'boyetttes' shall do in identifying themselves.

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