Skylar's Diary - Day 37

Let's say, Dear Diary, that today consisted of two parts. A more business-like part, and a... well, I’ll leave it up to you to label it. 

Today I had an appointment with Mrs. Liang, during the lunch break. I was quite nervous to say the least, because I would admit to her that I like to dress like a girl. Although she seems to be the type of person who will probably understand.

We sat down in a quiet room, opposite to each other.

"What would you like to talk about, Skylar?"

"It's a long story."

"I'm listening."

And I told my story from beginning to end. About Riley. About the sessions with Riley. What we did there. How I experienced all that. I told her about the wedding, and how happy I was then. I told about Riley's party. I also mentioned Raven once in a while, but I didn't want to say too much about her.

Mrs. Liang listened carefully, with a mild and empathetic smile. She looked at me all the time. Once in a while she asked me a question about a detail, and I answered it honestly. At the end of my story, I said openly that I like to dress and behave like a girl.

"I had already noticed, Skylar, that you were indeed experimenting. And also things you have been saying lately, pointed in that direction. Maybe the first thing I want to tell you is that I appreciate you being so open and honest with me. And that you show trust in me. Can I ask you something?"

"Sure."

"Do you think you'd like to be a girl?"

I thought of Meagan, who wanted to be a girl already as a child. And her situation was not the same as mine.

"Actually not, but I know why you're asking. Of course it would be easier for me, but right now I'm not really concerned with my body. When I try a little bit, people think I'm a girl."

"And do you like that, when people think that?"

"I think that's rather funny, but I don't intend to fool them."

"Did you want to talk to me about this, Skylar? So I could understand the picture that Raven showed me?"

"Yes, but there's more."

"What then?"

"I have another wish. I also want to be able to be who I am at school. I want school time to be girl time as well."

I didn't want to say more than that for a while. I first wanted to know how she would react. I looked at her. She saw that I was waiting for her reaction. She didn't react immediately, but then she said:

"I understand you, Skylar, but you probably also know that you could get into trouble. I think it's a wise thing to come and talk to me first. There are a few things you need to know. First of all, we think it's extremely important that every pupil can grow and develop further here at this school. That everyone can find out who they are, and who they want to be. So, as a school, we want to support your quest as much as possible. Secondly, our school pays attention to diversity and inclusion. Students who are different also have their place here, and we want this school to be a safe environment for them. For these reasons, I think we should help you as a school with your wish."

I was so happy when she said that. The tension I had before we started the conversation was turned into hope. A lot of hope. She continued.

"I suggest the following, Skylar, and then you just have to say what you think of it. I suggest that I discuss your wish with the teachers' team. I think it's important that everyone is informed. But that also means that they will all know."

"I don't mind, I don't want to keep anything secret anymore. It's uncomfortable to keep something hidden."

"So that's all right then. But the hardest part will be the reactions of the fellow students. Some will support you, for many it won't matter, but there are also going to be some who are going to complicate things for you."

"I'm aware of that, and I admit that I'm afraid of it."

"But let's work step by step. In a few days' time, we have a meeting with the team. By the end of the week, you and I will sit together again. Is that good for you?"

"That's perfect."

"I also know that you are with Raven. Does she know about it?"

"About my wish? Actually not yet, I haven't discussed it with many people."

"I think it's important that you talk to her about this as well."

"I understand that. I will do it."

And at the end, she said: "Skylar, you are a special boy. I'm glad you're in my class."

"Thank you, Mrs. Liang."

We said goodbye, and I went out again with a euphoric feeling. I didn't talk to anyone about the conversation, except with Raven, although I haven't told her everything yet. I don't know if Raven would like me to go to school in a skirt. Then she is confronted with her own challenge, so even if the school would allow it, I want Raven to like it too. I did tell Raven that I had explained everything about the wedding, very honestly. And that I would probably wear more girly things at school, but not that I would go very far in that. Maybe that's something to discuss on the train tomorrow.

So that was part one of the day, Dear Diary. Now here’s part two.

After school I went with Raven to her home. We were there alone. We ate something, together, relaxed, and effectively worked on a task for school. At least ten minutes anyway. Then she took out a package. 

"That's for you," she said.

"Another present? Aren't you almost broke?"

"Oh, this didn't cost me anything, it's mine, and you can have it."

"Thank you," I said, and I opened the package. It was a white baby-doll nightgown. It had a high waist and a cute red bow on the front. I smiled.

"I'm going to sleep well in this," I said. I was really looking forward to sleeping in this, in Raven’s nightie.

"Come on, put it on."

That was to be expected, but I held off for a while. 

"May I ask you something first, Raven?"

"Of course, what is it?"

"You know that I love you, and I also know that you love me, but I keep finding our situation a little weird. Sometimes I wonder if you don't want a real boy as a boyfriend." So, it was out. But Raven didn't have to think long though.

"Are you really wondering?"

"A little bit. Sometimes." She looked at me, and smiled.

"Oh, Skylar. Look, you know I'm always very honest. You should know that you are a boy to me. A real boy. And an incredibly cute boy, like I don't know anyone else. No, you're not an ordinary boy, there’s a lot of girl in you, and you let her out, and that's what I like about you. I really wouldn't want it any other way."

I was very happy with what she said.

"I'm sorry I had a little doubt."

"You don't have to say sorry. I understand."

I didn't want to talk about the party or about my wish yet. It was fine for the moment.

"Do you want me to put on your nightie?"

"Yes, but be careful. Maybe I'll find you too cute."

"We'll try it out." I walked to the bathroom to change my clothes. I wasn't ready yet to change in her presence. With the nightie on I went back to her room, and when I went inside I saw her sitting on the bed, also wearing a nightie. The one she also wore during our 'lingerie' session.

"Come on, get on the bed," she said.

I sat next to her on the bed, on my knees, and she looked at me. I looked at her.

"Yes, it’s true," she said.

"What is?"

"I think you're too cute."

She came closer, and kissed me on the mouth. I closed my eyes, and I think she did too. We kissed, and that was the only contact we had. We did nothing with our hands, but that made the kissing very intense. I got excited, and so did she.

"Come on, sit on the edge of the bed, with your feet on the ground," she said. I did what she asked.

And then she came and sat on my lap. With one leg on each side of me. This was very intense. I felt her skin on my skin. Her soft warm smooth skin on mine. And she kissed me again. And I got very excited, if you know what I mean, Dear Diary. I found it a bit embarrassing, but Raven just found it enjoyable. As if she got flattered.

"Oh, now I can feel that you are a real boy," she whispered. And we kissed again. Very sweet. Very quietly.

She took my hand, and put it on her breast. That was the first time in my life that I felt this. A feeling I could never have imagined. I stroked her breast. Very gently. Our breathing became more restless. We kissed more intensely. We rocked up and down slowly and gently. The bed was soft.

And suddenly I felt her hand, there, under my nightie. She caressed me, there. I even got a bit dizzy, I found it a bit embarrassing, but I didn't want it to stop. I felt a bit trapped between her thighs. Our breathing became louder, and we rocked a little faster. The excitement became ecstasy. It didn't take that long. I exploded, if you know what I mean, Dear Diary. An intense feeling of a few seconds, but an incredibly wonderful feeling.

Raven knew what had happened, and she started giggling a bit. The kissing and rocking had stopped. I had absolutely no idea what to say, and suddenly realized what an embarrassing situation I had ended up in.

"You are definitely a boy to me," she whispered, and kissed me a few more times in my neck.

"I'm... I'm sorry." That's what I said.

"It's okay, dreamgirl, it's okay." She grabbed me tightly again.

"I love you," she said.

"I love you too."

We stayed on the bed for a while, but then I said I wanted to go to the bathroom. She understood, of course. I undressed myself completely, and washed myself. I also washed my underwear, but of course it was too wet to put on again.

She asked at the door: "Do you need anything else?”

"Erm, yes, I don't have any underwear."

"Do you want something from me, or from my father?"

Both options were embarrassing, but the latter I found even more embarrassing.

"From you. But please just keep it simple."

She giggled.

A minute later she was back, she knocked on the door, I opened it a little bit, and put my hand out. You can't get the details of what I got from her, Dear Diary, but I'm still wearing it while I'm writing this.

Anyway, I quickly put on my own clothes again, and that was necessary, because suddenly I heard Raven say: "My parents, they're home."

"What should I do?" I whispered.

"Everything is fine. Come and say hello."

I checked in the mirror, I looked fine. I went with Raven to her parents, who were in the living room. They indeed seemed very friendly, as Riley said.

"Father, mother, this is Skylar."

"Skylar, this is my father and mother."

"Nice to meet you," said her mother. Her father nodded. We shook hands.

"So, did you guys work well for school?" asked her mother.

"Yes, it’s all done," said Raven. That wasn't a lie.

"Do you still have to go home walking?" asked her father. "Otherwise I'll take you there."

"Oh, that's not necessary," I said.

"Please allow us," said her mother, "it's already late, and dark outside. It's really no trouble at all."

I checked with Raven. She nodded that it was fine. She had quickly put her nightie in my bag, and gave it to me.

And so it happened that her father brought me home.  I was sitting next to him in his car, wearing his daughter's undies. If he would know what had happened… In the meantime he tried to start a conversation, but it went well. He asked some routine questions about school and other stuff. He also asked what my father was doing, which is still difficult to talk about.

While I was in the car, I suddenly thought of something else. I had to send a message to Raven immediately. In order not to seem rude, I asked if it was okay. "Go ahead," said her father.

"my underwear. it's still in the bathroom", I sent.

Fortunately, the reaction came pretty quickly.

"i’ll look for it"

The two minutes after that message seemed to take hours.

"it's ok. got it."

Whew, I thought. Her father dropped me off at home.

What a day, what a day, I keep thinking. But I do think I'm going to sleep well, in Raven's nightie.

To: Skylar's Diary - Day 38