Skylar's Diary - Day 8

Dear diary, today I have been through some embarrassing moments again, but this time it is really my own fault. I came back from school, had a quick bite to eat, and worked a bit for school. This time Riley had left a bag of clothes in advance. I was allowed to go through everything myself and then choose what to wear. It was mainly shorts and tops again, and also a couple of blouses. I tried them on, looked in the mirror, tried another combination, and so on through the pile. At the very bottom of the bag was a school uniform, for girls. Probably Riley’s old uniform. It was such a typical dark blue uniform with a pleated skirt.

Well, I won't wear that... but I could try it. So I put on that skirt, with the matching top. And that was a very strange feeling, but actually a nice feeling. So light. There is fabric around your legs, but not between your legs. Very strange to feel your own bare legs against each other. And when you move, it seems as if that fabric caresses your legs. I thought that was very sensual. And just like yesterday I started twirling. I couldn't suppress a smile.

I looked in the mirror, and had to get used to what I saw. I saw a cute girl, but with my head. And then I started taking crazy poses. Legs far apart, tongue sticking out, a pirouette (ideal with that skirt),... and then I also made some funny girlish movements.

I saw that it was almost time, Riley would be there soon. I wanted to take off the uniform soon, but it didn't work out. The zipper of the skirt was stuck. At first I tried it quietly, maybe you had to use the right technique, but that didn't work. I also pulled that zipper as hard as I could, but it didn't move. I also tried to take off the skirt with the zipper closed, but that was impossible. Damn it, and Riley will be right here. I really didn't want her to see me like this. 
Eventually I accepted it. It didn't work out. I would explain it.

Riley came in.

"Well, well, look who's wearing my old school uniform? Were you curious? Did you want to know what it felt like to wear a skirt like that?"

"Erm, yes, but I actually wanted to take it off again. But the zipper is broken."

"And did you want to take it off immediately?"

"Erm, no."

"Did you look in the mirror?"

"Erm, yes." I turned crimson.

"And did you like what you saw?"

"I've been doing a little crazy."

"Have you twirled?"

"Erm, yes." How could she foresee all that?

"So you liked it."

"Erm, yes."

"And how does it feel to have a skirt on?"

"Right now? Embarrassing, because you're here."

"Oh, you really shouldn't feel ashamed. There's nothing wrong with enjoying wearing a skirt. Actually, I'm really glad you tried this. Most guys take much longer."

"Most guys?"

"Yes, I've had other customers, you know. You know what? We're not going anywhere today. Keep my uniform on. You'll get used to it. I'll help you with that zipper later." She had me again. Would she have known about the zipper?

Today we talked a lot. Most of the time I wasn't aware of what I was wearing. At a certain moment Riley took my list again, and it said "Sometimes I think boys are stupid."

"Why do you sometimes think boys are stupid, Skylar?"

"I don't think so, that's what I think girls often think. That's what I gather from their reactions."

"But can you give an example of that?"

"Yes, girls don't like it when we act tough. That we do all kinds of things to impress others."

"And do you ever act tough?"

"Yes, sometimes I try to behave like a cool guy."

"...says the boy in the pleated skirt"

"Riley, that's not fair."

"Sorry, Skylar, I couldn't resist." She laughed, but I could appreciate the joke.

"But do you really like that, having to be tough?"

"Actually not. Boys can be rough on each other."

"And do you think girls like the bad guys the most?"

"When I think about it, most likely not."

In the end I came to the conclusion that doing tough is nothing good for anything. It's stupid. I could already tick that on my list.

As far as the uniform is concerned, hmm. It can be fun to wear something like that. When it's hot in the summer, many boys would be happy with a pleated skirt (instead of long pants). And it might look cute and playful, but I'd rather die than go outside in a skirt.

To: Skylar's Diary - Day 9