Skylar's Diary - Day 42

Yesterday I was cheerful and relaxed, but this morning I was a bit nervous. I was looking forward to the brunch, but I realized that it could be an intense experience, with all those women who mean so much to me.

I was also a bit indecisive about what I would wear. Would I really put on that lingerie set Riley gave me? At the time I just wanted to give it a try, and I liked it, but I found it very sensual as well. It was something for home, not to go outside with.

And I would wear false breasts. Would I really go that far? Do I want that? What does that mean? Does that mean I don't have the body I want? Do I want the body of a girl? I don't know the answer to these questions, and it's just one of the things I wanted to discuss with Meagan. I don't think anyone I know is more qualified than her to talk about this.

Raven also asked me to wear those things. I could say that I'm wearing this for her, but shouldn’t I do it for myself too? I decided to try it first, in my room, and then I could still change my mind.

I went to my room, and there I already laid everything out nicely on my bed. I took a shower, because now too I wanted to be very clean first. I put on the panties and the bra, very carefully, stepped into my dress, and closed the zipper on the side. It fitted perfectly on my body including breasts, even better than yesterday. I put on the shoes Raven gave me yesterday, and I carefully tied the big red bow.

Before I looked in the mirror, I already felt very delicate. It all felt so perfect. All the materials on my body were as light and soft as silk. I moved around very carefully, and closed my eyes to feel more intensely. I stroked the dress with my hands. So soft. I patted my falsies, and was very conscious of the shape they created. I had never felt so special.

I stood in front of the mirror. Oh no, my shoulder straps were visible. I tried to push them under the dress, but they kept bouncing back. I realized that everyone would see those shoulder straps, so they would know that I was wearing a bra. Maybe that didn't matter either, because my breasts stood out anyway. They were even more accentuated by the bow that made my waist narrower. My figure was now very girlish. I started to doubt again. The same questions came back. Do I want to go that far? Do I want the body of a girl? What would everyone think?

An answer to that last question came quite quickly, because suddenly my mother entered my room. I was startled, and felt caught. I blushed a bit, but couldn't say anything immediately.

"Oh, Skylar, you look so beautiful." Her answer was very disarming. She inspected me from head to toe.

"Are you sure about that? I mean, would I do this, with those fake breasts?"

"Ah, why not? That's funny, isn't it?"

For her it was a joke, for me it was a big deal. But rather so than the other way around.

"It makes me feel a bit uncomfortable anyway."

"I can imagine that, but look, you like to dress like a girl, and that's just part of it, isn't it? It's a kind of finishing touch."

Mother's words reassured me. Maybe I shouldn't make a big deal out of it. And then I had a practical question:

"Mother, the shoulder straps are visible. Isn't there a way to hide them under my dress?"

"Why would you? All girls wear a bra, so why not show it? And even without those visible straps, we'll all know that you're wearing a bra. Wait a minute, I think there's something missing. I’ll be right back."

Mother went to her room, and came back with a small golden necklace. She put it around my neck.

"Now you're all set. Look, now you're going all the way, then you can say you've been there at least once."

The bell rang. It was Riley and Raven, who was picked up by Riley at her home.

Raven was over the moon. "Oh my god, you look so pretty, and cute!!!"

She came closer to me, but didn't touch me. She first inspected me from head to toe, from shoulder strap to false breasts. "I think I can guess what else you are wearing..." she whispered in my ear. "Stop it," I whispered back "it's already awkward as it is."

"Isn't he a doll?" she asked Riley.

"Raven, Skylar is not your doll." She said it with a smile, but also put Raven in her place.

"But you are allowed to give me a little kiss," I said, and I offered my cheek. 

She gave me a very soft little kiss, her lips barely touched my cheek. You know, lipstick, blush...

We all got in the car, and I did that very carefully. There shouldn't be any wrinkles in my dress, so I smoothed my skirt with my hands before I sat on it. Raven and I were sitting in the backseat, and she had the greatest time. She pressed her finger into one of my falsies, and said "cheater ". "Hey, I’m doing this for you, you know," I whispered. "Dream dream dream dream girl," she said.

We arrived at the house of Meagan and her wife Carole. It was a small but very nice house, with a small, but very well-tended garden. Meagan opened the door, and welcomed us. It immediately struck me that it was very cozy inside. There were many plants and flowers in the house. There was special wallpaper on the wall. There were nice cushions in the seats. There were candles, beautiful carpets... There was a fairly large round table, very stylishly set for six.

We were invited to go straight to the table, because nobody had eaten anything yet. They had really done their best, with healthy and tasty things. Freshly sliced fruit, granola, still warm whole-wheat bread rolls, real butter (a little bit of sin is allowed), smoked salmon, homemade jam, soft boiled eggs, croissants (a little more sin is allowed as well). It was all so beautiful and so delicate that I ate very carefully. I cautiously took the things I wanted, put them neatly on my plate, took my cutlery elegantly (no elbows on the table of course), and ate in small bites. What a difference with the Skylar of the past. No, I didn't want to be out of tune with all those stylish, elegant women.

We'd rather talk about everyday things. I was a little scared beforehand that it would all be about me, since that wouldn't have made me feel comfortable. This was perfect, as if all of it was the most natural thing in the world. I, the teenage boy, was sitting there wearing the most beautiful dress in the room, if I may say so myself.

At a certain moment I took the floor. Not that I had planned it in advance, it rather happened spontaneously.

"Meagan and Carol, I want to thank you very much for your invitation. I am very impressed. It's very nice here, and the food is delicious. It is very important for me to be able to meet you again, because you are a bit of an example to me. You know that I’m not complying with certain standards, but neither do you, and I mean in a positive way. In truth, you show me how a very valuable life can be led in this way."

They kindly accepted my words. I saw Riley looking at me.

"Riley, I don't think I've said it explicitly yet, but I'm also very grateful to you. I must say, the first time I met you, I thought you were a very weird girl, with weird ideas, but along the way I understood where you wanted to go. It was a very odd road that we followed, a road that I would never choose myself, a road full of obstacles as well, but you showed me the way. We're not yet at the end of that road, but now I do realize the beautiful things I've come across on that road, and that I'll carry with me forever. I'm going to say something unexpected, but sometimes I think you're a very old woman, in the body of a young woman. Again, I mean that as a compliment, because there's so much wisdom and calmness in you. Thank you, Riley."

"Thank you for those nice words, Skylar." (That joke about the old woman could be appreciated.)

And then all of a sudden I thought I should thank everyone.

"Mother, maybe first I should say I'm sorry that I haven't always been a nice child to you. There may have been the excuse that we had a setback, with the loss of father, but you have always been kind to me."

Then I stalled for a moment, there were tears in my eyes. And so there were in mother’s eyes, because when I cry, she has to cry too. And then I should not look at her, so I looked at Raven, but she also had a few tears. And even Riley...

"OK girls, I'll stop for a minute, or we'll ruin our mascara." While we laughed, we gently dabbed our tears with the beautiful napkins.

"Mother, let me get on with it. I also want to thank you, because you found Riley, and even more, you let me explore without judging once. I realize that I do things that many mothers would have a problem with, but you saw me become happier, so you let me go on with it. It is wonderful to know that your love is unconditional. Thank you."

"It's okay, Skylar, I love you." "I love you too, mother."

Well, now I had thanked everyone except Raven. I looked at her, and she looked at me, and nobody said anything. I knew everyone was waiting for what I would say. But I also kept quiet. On purpose. And then I said:

"And you, Raven, you're just a goofball.”

Everyone had to laugh, Raven too, but I also wanted to say something nice.

"...but you're a goofball I love. Without you, I wouldn't have dared to do what I do. You are my first love, and the only fear I have is that it will never be surpassed. So you will have to stay with me."

"Don't worry," she said, and she kissed me softly on my cheek again.

There was an embarrassing silence for a moment, and that's why Carole asked:

"Shall we all go into the garden for a moment? The weather is nice."

And so we all went outside, and looked at the beautiful bushes and flowers in their garden. There was even a small vegetable garden, where Carol grew her own fruit, vegetables and herbs: cherry tomatoes, peppers, beets, zucchini, pumpkins, raspberries, strawberries, parsley, thyme, rosemary, basil... And if something had to be harvested, Carol would bring it all to the kitchen, and then Meagan would turn it into something delicious.

At one point Meagan and I stood together.

"Skylar, you wanted to ask me a few more things..."

"That's right, and thank you in advance for helping me."

"I'm happy to do it."

"I'm still struggling with a few things. I think you know my history. How it all started, with Riley. Your wedding. Riley's party where we've talked before. It all went very fast. If you had shown me a picture of me now a month and a half ago, I would have called you crazy. But in the meantime I've changed a lot. I have discovered the girl inside me, and I want to let her out. And everyone may see it. Tomorrow I'm even going to school in a skirt, and I'm looking forward to it."

"That's all very good, isn't it?"

"That's true, but I've begun to doubt who I am. Look, today I'm even wearing false breasts. At first I thought it was very strange, but after a while I also started to like it. And then I ask myself the question: Do I want breasts? Do I want another body?"

"I can imagine, Skylar, that you have these questions. I used to ask myself those too, but for me the answer was straightforward and came quick. Yes, I wanted a different body. When in doubt, it means that you have to think even longer. Remember that it's not easy to change your body. It takes a long time to prepare, you have to talk to experts, and it's a long process. Some things can't be reversed either."

Meagan gave me a very long explanation about how things had gone with her, and I was a bit disappointed with that. At a certain point she also said:

"You're still young, Skylar, and you don't look too masculine yet, but you'll change, you'll become more muscular, you'll have hair growth on your face... And then it'll be harder for you to pass as a girl."

I was very sorry to hear her say that.

"There are ways to do something about this without making a complete transition, but it's not the same thing.”

So, unfortunately, there was no simple answer to my question.

"Anyway, Skylar, right now my advice would be: Inform yourself well, and take time to think. You don't need to know the answer today. Dare to talk about it, especially with your mother, but also with Riley and Raven. And remember this: there are many ways to express your femininity."

Even though I didn't have an answer to my question yet, the conversation still helped me. I don't have to hurry, it's not urgent. And especially her last sentence I memorized well.

"Thank you, Meagan, it helps to talk to you already. I had another question. Am I a 'he' or a 'she'? Because the people who know me know that I'm a boy, but strangers who see me dressed like this, think I'm a girl."

"What would you prefer?"

“Well, I guess it makes sense that I’m a ‘she’ when dressed like this, and I really don’t mind then. But I’m not a girl like you or Raven.”

“I see what you mean, but your body should not define what you are. If you feel like a girl, it’s perhaps better that you are addressed as one. For me, you are a ‘she’, unless you don’t like that.”

“I actually do like it, certainly if you say it.”

“Then perhaps you should talk about this to everyone you care for. Your mother, Raven…”

"Raven sometimes calls me dream girl, and I think it's funny."

“I can imagine that she says that.”

So, I’ll  have to talk to mother and Raven, but also to friends like Devon. The thought of no longer being a he/him remained strange though... Again I realized that I needed time for this.

"Maybe one last question. Do you have any suggestions for tomorrow, when I go to school in girls' clothes?"

"A very simple recommendation: Enjoy it. The first few minutes are going to be weird, but it's going to be one of the best days of your life. That's how I experienced it. I remember exactly where I was, and what dress I was wearing, the pin in my hair, my makeup, the color of my nail polish... I had also announced it, and the people who were important to me were very supportive, and that's also the case with you."

I was very happy that she said that. It was perhaps the best advice she could give. I gave her a cautious hug.

We went back home in the afternoon. Riley went on, but Raven stayed. We both still had work for school, and we did it together. I had taken off my dress first, because I thought it was not suitable for homework. I put on the blue dress that Raven once gave me, without false breasts. These are only for special occasions. Not for homework, and not for tomorrow at school.

I started to get a bit nervous again for tomorrow. How would everyone react? Are they going to accept me? Are they going to pretend that nothing is wrong? Are they going to treat me? Raven noticed my nervousness. "Ah, you'll see, it's gonna be all right." We'll see. Hopefully I can enjoy it, as Meagan said.

To: Skylar's Diary - Day 43