Skylar's Diary - Day 13

I wasn't worried about today beforehand. I knew what Riley was up to, and I knew we'd stay home. And yet something has changed in me.

As Riley had announced, I would dress up as a girl. Extreme femininity, she called it. I would fit really fancy clothes, and go all the way. It would be innocent, and I would just give it a try.

She had a whole pile of clothes with her again, and I was allowed to try them on. They were all very girly things, and I still felt the reluctance of the first few days.

"I understand that, Skylar, but just let go. Think of it as a game."

I already considered the first outfit very special. It was a white wide summer dress a little over the knee. The shoulder straps were dark blue, and there was even an underskirt in the same color. Riley also had brought shoes in the same blue, and these had fairly high heels, so I found it difficult to walk with them. Also special were the bow at chest height and the many ribbons around the neck, the wrists and the feet, all in a light blue color. It took a while before I had that outfit on. I looked in the mirror, and walked around a bit, as always.

"How does it feel to be wearing this, Skylar?"

"Girly. Very girly."

"And what does that mean, girly?"

"The dress feels exceptionally soft. It is actually very beautiful too. If I were to see a girl wearing this dress, I would look at her a little longer."

"That's a sign that you like beautiful clothes."

"...if someone else is wearing them."

"And not if you're wearing them?"

"Well, the dress will still be beautiful of course."

"I know one more nice thing, a graceful bow. Grab the dress carefully with your hands, and pull the dress outward. Put one leg in front of the other leg, and make a bow. Oh, that's so cute. Do you want to keep the dress on for a while?"

"Yes, actually I do." I had to admit that it was nice to wear that dress. Especially the way it moved when I stepped or spun around, I found very pleasant. Riley watched it with a smile.

A little later I had a new outfit on. The most striking thing was the floral skirt, which also fell out very wide because of the petticoat. The top was black and was tight around my body. For fun Riley had put a filling in it, so it looked like I had breasts. She found that very pleasant, but I also found it funny. Riley added a few finishing touches: a pearl necklace, black gloves, a purse that matched with my skirt, and pink ribbons on top, shoes and gloves.

"What's that petticoat for anyway, Riley?"

"To make the skirt fall wide. That accentuates the female figure: a narrow waist, and wider hips."

"This outfit feels quite different."

"Really? Tell me about it."

"It is more exquisite. The previous dress was playful, and I felt like a young girl. This outfit is more delicate, and I feel more dignified in it."

"I can understand that. It's also more expensive clothing."

"Riley, I have a confession to make."

"What then?"

"I actually enjoy wearing these clothes. It's a nice feeling, and I feel pretty."

"You are a very handsome boy, Skylar, you know that?"

"But I also feel guilty."

"Why?"

"I am a boy. Boys aren't supposed to like having girls' clothes on. If my friends were to see me, they would make fun of me. I'm doing something here that has to be kept absolutely secret."

"I understand very well what you're feeling, Skylar, but you shouldn't feel guilty at all. There's nothing wrong with liking this. By the way, there are a lot of boys like you, you're not alone."

"Really?"

"Yes, I'll tell you more about it later. And as for that secret, rest assured, my lips are sealed. I won't tell anyone you like it. As a matter of fact, I'm already very happy that today you are freely enjoying what you're wearing. It's also a sign that you trust me, and I appreciate that."

It's still unclear to me where this program will lead. I've explored that extremity now, but am I ever going to do anything with it? I don't see myself walking down the street in clothes like that, no matter how beautiful they are. I said something about that to Riley, and she answered:

"To be honest, I don't know where we'll end up either, but what I can tell you is that in the end you'll feel like a different person, very well in balance, with more self-confidence, and an open mind."

Well, we'll see, I thought. We also talked about all sorts of other things and played some games. At the end of the session we chose an outfit for tomorrow, when Riley’s cousin is coming. It's a slightly simpler outfit than today's, and I'll show it to you tomorrow, Dear Diary.

"And what should we do tomorrow, if you're not around?"

"That's up to you, Skylar. Get to know each other, and do things you like."

"Can I know her name?"

"No, you're supposed to introduce yourselves to each other. My cousin doesn't know your name either, nor does she know where you live. I'll drop her off here tomorrow, but then I'll drive on."

It remains exciting..., tomorrow, but I know now that I can trust Riley. It will be fine.

To: Skylar's Diary - Day 14