Skylar's Diary - Day 5

After that exciting day yesterday, we took it easy today. We simply stayed at home. Shortly before Riley arrived, I quickly put on the shorts and the pink t-shirt, as well as the black flats.

"So, I thought you would never put them on again?" said Riley when she came in.

"I have to admit they're comfortable, and above all, they're very easy to put on and take off."

Riley smiled. A little too triumphant, I figured.

She had a bag of clothes with her (where does she keep getting them from?), but quite common things actually. I went through the heap, and eventually chose to wear simple black shorts (without pockets, so I couldn't be fooled), and a simple black top that was actually a bit too short, so you could see a piece of my belly. I tried to pull it down. "Don't bother," said Riley. There were some longer tops, but they were too girly. There was also a cardigan in the bag, and it was comfortable. 

"What are you wearing?" Riley asked. 

"You can see that, can't you? A cardigan."

"Can you describe it in words?"

"Erm, a knitted cardigan, light gray, slightly oversized, so loosely fitting."

"Fine." 

Why does she ask that now, I thought, but I had a more urgent question "Riley, why do you want me to put on those girls' clothes?"

"Oh, I could talk about that for hours, and I promised to be honest with you. Let's sit in the living room in the couch. With a cup of tea or so?"

A little later we were sitting on the couch with a cup of tea, and cookies. Pretty cozy. 

"About the clothes, Skylar. It's not really about the clothes themselves, but about the impact they have. Do you remember how aware you were of your body when you got out of the car yesterday?"

"I really didn't feel comfortable."

"Indeed. You could say, they're just clothes, pieces of fabric that cover your body, but that's not how it works. Clothes do have an impact on what you think, how you feel. And I want to show you that there are other ways of thinking and feeling."

"I still understand, but then I might as well put on some crazy boys' clothes."

"That may be true, but we'd have to do really crazy things, and you'd look too eye-catching. Then maybe you'll do things that really don't suit you.  And to be honest, I also want you to explore your feminine side."

"What's that good for? I'm a boy after all."

"I know that, and I also think that you are actually a very cool boy. But everyone has both male and female traits, but boys tend to suppress the latter. We don't think that's good for their development. Look, women started exploring their masculine side a long time ago. They used to all be at home as housewives, but in the meantime they have started to study and work, and some of them run large companies or even countries. Their clothing has followed that trend. Girls used to have many restrictions, but now they wear anything. I say it: what you wear also determines who you are".

"But I don't want to be a girl!"

"That's really not the plan, Skylar. The goal is to explore. Out of your comfort zone. To wear other things, and consequently to think and feel differently. There are still so many options..."

"I guess I don't like it anyway."

"I understand that. These are internal barriers and taboos imposed by society. I want to help you to lift these barriers. And I want to break those taboos together with you. You will notice how liberating that is. Compare it with a roller coaster. Before you get in, you're a bit scared. But once you're in it, that fear turns out to be unfounded. Think of yesterday."

"I know what you mean. Afterwards, I found it exciting and actually also funny."

"I really appreciate you saying that. And then there's a second advantage. By doing this, you can better empathize with the lives of girls. Someone who can do that well, will benefit a lot from it. Wait, you'll see."

"Hmm, I doubt that."

We talked a bit more, also about very everyday things. About my school, about her work and her studies (she's in college, major psychology). Then she asked if I wanted to watch a movie. She had brought a DVD, "My Girl". Typical Riley. At first I thought I wouldn't like that, one of those old girl movies (made more than a decade before I was born). But it was actually a beautiful movie. It was a sad story. I tried to hold back, but at a certain point I started to snivel. But Riley was crying too. 

"Yes, that's number 7 on your list."

OK, there she had me. She also gave me a paper tissue. She had set them up beforehand, so sweet.

"And that's number 12", she said.

I took my list again, and numbered the items. So I can already check number 7. Number 12 is actually for Riley. I think I should mark number 11 for myself instead.

To: Skylar's Diary - Day 6

Skylar's Diary - Day 4

Dear Diary, so I didn't sleep well last night. I constantly imagined people staring at me because I would look so ridiculous in short girls' shorts and a pink t-shirt. Now, in the worst case, if it's necessary, I'll just say that it's a game, so they might understand.

Riley arrived home in the early afternoon, with the shorts and the pink t-shirt. She had taken these for a wash, she said. I put them on, we got in the car. We drove all the way to the other side of town, as she had promised. I hadn't actually been there before. We parked near a big shopping mall, and we walked to that place.

Then I suddenly became very nervous. I became very aware of how short my shorts were, and how uncovered my legs were. I felt very exposed. The pink t-shirt didn't help me to feel at ease either. Riley realized this, and reassured me. "Watch out," she said. "You may be very conscious of what you look like, but most people are dealing with other things, and will ignore you." That was true, actually.

Anyway, we're going into the shopping center, and I thought I'd put my hands in my trouser pockets. Then no one would see my painted nails.

"What's wrong with these pockets? I can't get my hands in it."

"Why do you want to put away your beautiful hands?"

"Because my nails are painted!"

"I was afraid of that. That's why I sewed up the pockets."

"Oh you, prankster!" 

"Forgive me, Skylar, but look at my hands and toes. I also walk around like a clown, thanks to you."

She had a point there, but man, that was so annoying. I realized that I always walk with my hands in my pockets, and suddenly it was no longer possible. What the heck should you do with your hands? I didn't know what to do.

"Just keep them quiet next to your body, and walk. Your hands will automatically swing slightly."

Well, that took some time to get used to, you know. And again I thought everyone would see my hands, but Riley was right. Most people don't even see you at all.

We just walked around and stopped by a shop window once in a while. Riley went into a shop every now and then to look at clothes (for her!), and sometimes she asked me what I thought of it, but actually I rarely had an opinion. "The time will come," she said. Well, I don't think so. 

And just when I thought the whole trip wasn't too bad, the next embarrassing moment came. Riley wanted to buy me shoes. "What's wrong with my sneakers?" I asked. 

"Nothing, but I want to expand your shoe collection. I can bring a bag of clothes to the sessions, but shoes are more difficult, you better buy them new."

"But that's a waste of money, Riley. I'm never going to put those shoes on." 

"That's up to you, Skylar, but don't worry, it's not the intention to buy very girly shoes. Let's just try it, please."

We went into a shoe store. Only girls' shoes. I was the only boy in there. But Riley kept her word. She selected very simple flat shoes. She had found black ones, but not in my size. She asked the saleswoman if they also had my size. "Yes, sure," she said, "I'll get them."

I already sat down, and when the saleswoman came with the shoes, I would try them on.

"You also have to take off your socks," said Riley, "you wear these flats without socks."

I became crimson. My toes! I whispered as loud as I could.

"Riley, I can't, my toes are painted."

"Don't worry, your fingernails too." And while she was saying it, she took off my socks. I thought, "Oh no, what's that saleswoman going to say now?" And do you know what she said?

"Wow, you have really beautiful feet, nice color by the way."

Didn't she realize that I'm a boy? Maybe I really need a haircut, although... In this case my too long hair has worked for me. But it didn't stop there.

"With such beautiful toes, you have to wear sandals. Wait a minute, I'll get a nice pair."

Before I could say anything, the saleswoman went to get them. Meanwhile, Riley helped me to try on the flats. That was not so bad. I tried to walk with them for a while, and they were quite comfortable. "Good, we'll buy these already," said Riley.

The saleswoman came back with a pair of sandals. White, with ribbons. Definitely girls' shoes.

"Come on, try them on," said the saleswoman. 

Dilemma. Think fast. If I refuse now, she's going to expect a reason, and I can't say I'm a boy. When I tell her that I don't like them, she will look for other ones. When I say I don't want sandals, Riley will probably intervene. OK, just fit, and pretend like there is nothing up. I tried on the sandals, and these too were comfortable. I walked back and forth for a while.

"Beautiful," said Riley and the saleswoman, almost simultaneously.

Just let it pass, I thought. Riley confirmed that we would take both the flats and the sandals.

Okay, so now I'm a boy and owner of a couple of flats, and a couple of sandals. At home they will die a quiet death in the closet.

"Are you hungry?" Riley asked.

"Yes, actually I am."

"Okay, here's the deal. If you keep the sandals on, you can choose where and what we eat. If you put on your sneakers again, I'll choose."

So that's how it works. I couldn't call it blackmail, because I had a real choice. But I really wanted pizza, and Riley would probably go for a healthy salad.

"Okay, I'll keep the sandals on, and we'll eat pizza."

"Perfect. That was my idea, too."

Darn it, fooled again.

The rest of the day was quite routine. We went to eat pizza, we walked around a bit, and Riley brought me home. "I had a nice afternoon," she said. 

"Things were not so bad," I said.

"Didn't you like it, then?" 

"Well, actually I did enjoy it. It was exciting, and that made it fun."

"I'm glad you enjoyed it. See you tomorrow, Skylar."

"See you tomorrow, Riley."

To: Skylar's Diary - Day 5

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

Skylar's Diary - Day 2

Today Riley dropped by again. So, she had a whole bag of clothes with her, and we had agreed that I would fit a few things. They were all girls' clothes, but Riley had promised that we would keep it simple. Dresses and skirts were not included. I'm not ready for that yet (if that ever would happen).

Today's plan was that I would just give it a try. Riley asked me to try things on all the time, and then I had to say what I thought of it. We had put the big mirror in my room. Riley was certainly well prepared. Almost everything she had with her fitted me, never too big or too small. Some things were really too girlish for me. Shorts that were so wide that they looked like skirts, tops with all kinds of frills, or tops with flowers or hearts. They didn't suit me. Eventually I chose a denim short and a pink blouse.

"Great choice, Skylar, it looks good on you."

"Do you think so? I still find it very strange. Aren't these shorts too slim?"

"No, that's how it should be. Roll up your sleeves a bit, that looks better. Do you think it's OK if I take a picture?" 

"Oh no, not at all, who knows what you'll do with it."

"Oh, but I don't mean with my camera, but with yours. So you always decide what happens to it."

"OK then."

"OK, then stand up and look at me. You know what? We're going to do it a bit girly already. Keep your arms stretched out next to your body, but slightly away from your body, that's it. And keep your hands parallel to the floor. That's right, that's so cute. And now a little smile. Awesome!"

"Why do you want to take that picture, Riley?"

"That's just for you. If you write in your diary, you can add that picture to it. That's a good thing to look back at later."

In a way, I thought it wasn't too bad. Riley was very supportive, and quite sweet to me. She made it very playful, so I joined in. Actually I liked it a lot, but it doesn't have to go any further than this for me.

To: Skylar's Diary - Day 3

Skylar's Diary - Day 1

Hello, Diary. So today Riley came by. So she is going to teach me all kinds of things. At first sight she looked pretty nice (below I paste a picture from her profile page), and she was also friendly, but the conversation... Man, man, what's in store for me! I don't think I will go along with this. Anyway, I promised again to do my best, but I also said that I don't think this will work.

Do you know what I have to do? Wear girl's clothes! Yes, really! 
Wait, I'll try to replay the conversation. First I asked, "But what are we going to do then?"

" Fun things, but things you haven't done yet. So, girl things."

"And why should we do that?"

"It's important to experiment at your age. The more experiences you get, the happier you will be later on. That has been proven. It also has something to do with gender, but I'll tell you more about that later. And you shouldn't worry. If you really don't want to do something, we won't do it."

"But what are we going to do? Tomorrow, for example."

"The first sessions will take place at home. Tomorrow I'll take a whole bag of my clothes with me to put on..."

"Why do you want to try on clothes here tomorrow?"

"Not me, silly, you!"

"What, should I try on girl's clothes? Well, that's not going to happen. I'm not a sissy."

"Skylar, I might go a bit fast, but I don't want to mislead you either. By the way, I think the word sissy is inappropriate and I'll never use it."

"But do you want me to become a girl?"

"No, certainly not, really. You will be the person you want to be. I sincerely promise you that. Trust me. Again, we are not doing anything that you really oppose."

I still don't understand what that's good for, wearing girls' clothes, but it can't hurt. When I'm at home wearing those clothes, no one will know. I finally promised Riley that I would do it, and then we'll see. I think I won't like it.

To: Skylar's Diary - Day 2

Skylar's Diary - Day 0

"Dear Diary". That's what all diaries start with, right? I'm going to be honest with you, Diary. This is not my idea, but I promised to do it. Because my mother and I have been in a lot of trouble lately, she has decided to do things differently. 

From tomorrow on, someone will come to see me and take care of me. And not just with anything, no, she's going to teach me how to explore the world of girls. Phew, as if I wanted to.

Why, you might wonder, dear Diary? (Of course not, you're a diary, you don't wonder about things.) Well, because apparently I have no respect for girls. Of course I do have respect for girls, but mother doesn't think so.

Well, I'm curious. Mother says that I will follow a program that according to science has already yielded many good results. As if I care about that. 

Well, I made a promise anyway, because I didn't like the alternatives at all. And besides, if I follow the program well, and behave myself, then I can continue to play games as much as before. And that is important. Gaming is fun.

So someone will come tomorrow. I'll let you know how it went.

I'm Skylar, by the way.

I'm a boy.

To: Skylar's Diary - Day 1

My journey

So, here I am. I get off the train and say goodbye to my family. Here starts my journey. A journey along a path to femininity.

A good start, I think, is a playful dress, borrowed from my sister. Not too fancy, but girly enough. I am not sure how people will respond. Perhaps they frown upon it, or they might give rude comments. Perhaps some will say they understand. Most likely, people will ignore me.

Anyway, we'll see where we get from here. This blog will contain the stories I come up with during my journey. I'll explore how femininity translates in young boys.

Enjoy, and feel free to comment.