Skylar's Diary - Day 12

Today things have been better than expected, Dear Diary. Yesterday Riley had proposed a new challenge to me: wear something feminine to school. It had to be a piece of clothing, a jewel, nail polish, or a hairpiece..., and I was allowed to keep it small and not too prominent. Of course I felt resistance in my head, but this program is precisely about overcoming that. Riley always manages to push me a little further, in a pleasant way even. How is she doing that?

In the end I chose a bracelet. There are other boys who are wearing a bracelet, I thought, although I also realized that Riley would make me wear a girly bracelet. Before school began she came home with a few bracelets, from which I could choose. Indeed all very feminine, but very beautiful bracelets. I chose a black bracelet with a large black gemstone, which is connected to a ring by a small chain. Very special. The black gave it something cool.

"But how am I going to explain this to my friends?" I asked.

"I'll leave that up to you, Skylar, but just be honest. That's the most important thing. If you start making excuses or telling lies, you're going to get in trouble."

"I'm afraid of the reactions though."

"I understand that, but that's what it's all about. You have to learn to deal with those reactions. Show self-confidence, and you'll notice that it won't be so bad."

So I went to school with a girly bracelet. For the first time in my life. Of course, at first I couldn't focus my thoughts on anything else.

The first thing I noticed is that most people just don't react at all. Either they haven't seen anything, or they find other things more interesting to talk about. Two times I even got a compliment, both from a girl "Beautiful bracelet, Skylar." "Thank you." That's all I could say of course. Also Mrs. Liang had seen it in class. "That's a beautiful bracelet, Skylar." and she continued with the lesson. The only one who really asked questions was my friend Devon.

"Isn't that a girl's bracelet?", he asked.

"Yes, that is possible."

"Then why are you wearing it?"

"I got it from someone who means a lot to me. It may be a girl's bracelet, but I like this person very much."

"Cool." That's what he said, that's all.

Later I told this to Riley.

"Really? Did you say that? And you were sincere?" she asked. "I think that's very, very sweet of you. I really appreciate that. You've been honest, and you've shown self-confidence. What's more, you showed others your appreciation for me. I'm a little touched now, really." Wow, she was really happy. 

She also told me what the plans were for the coming days. Tomorrow she wants to go 'all the way' with me. She wants to turn me into a pretty girl. "I want to know how well this can work, and I want to go to the limit with you. Then you've also explored that area."

If someone had asked me this two weeks ago, I would declare him or her crazy, but now that resistance is gone. I see it as a game, in this case a dress-up game, and Riley is the fun leader of the game.

However, what will happen the day after tomorrow, I am not quite sure about that. Riley announced it like this.

"The day after tomorrow I won't be there, but someone else is coming."

"Also a kind of trainer like you?"

"Not really, but she knows very well what this program is about. She is a girl of your age, a cousin of mine, and you can choose whatever you want to do. In this way you will learn to interact with girls in a different way, as peers."

"OK, but what am I supposed to wear?" 

I already had a hunch of course.

"I'd like you to wear a nice dress."

"I was afraid you'd say that, but I don't like the idea."

"I do understand, but my cousin already knows about it. She is expecting you in girl's clothes. And I'll ask her to wear a nice dress too."

"Do I know her?"

"That would be a big coincidence, but don't worry. She is a very nice girl with an open mind, and I have prepared her well."

It's a good thing that Riley is telling me this already. Then I can prepare myself for this in my mind, and I there won't be any surprises. The idea that another girl will see me in a dress remains very uncomfortable. On the other hand, Riley’s cousin knows about it. The plan is that we just do some things together. At home. I trust Riley.  We will see.

To: Skylar's Diary - Day 13