Chapter 1: Early Days

The dream began when the boy was three.

He dreamed of ships of iron that sailed without sails. Flying steel birds larger than any bird he'd seen. Towers made of polished glass that would shame the masters in Myr. Devices where men might communicate across great distance and a book where the sum of human knowledge were gathered. A fantasy fit for a boy, yet it felt to him as real as anything he knew.

He also dreamed of another life, so different from his own, where he was but a smallfolk among many instead of a scion of an illustrious line. A life of mundanity and mediocrity barely remembered. The man felt similar, yet so different. Like a reflection on a blurry mirror.

The dreams never stopped. He asked his family about about those dreams a few times. His father was simply amused. His mother was unbothered. His siblings were merely confused, and his maester dismissed his dreams.

"Nothing but your stray thoughts, young lord."

Eventually, he stopped speaking of his dreams. Even as they continued visiting him every night.

When he was five, he finally remembered.

103 AC, Driftmark.

A sweet salad made from kelp was the appetizer. A basketful of freshly baked bread. Whole crabs buttered and baked. Squid stew made black with its own ink. Lamprey pies and smoked salmon, with fresh fruits as the desert. Other than the bread and fruits, almost everything on the table was a bounty of the sea. Such a thing was a common sight, for it was the sea where the Velaryons built their wealth from.

"The Old King is dead."

Father spoke as we gathered to sit for a meal. Everyone, including Mother, seemed surprised by the news. The raven bearing the news must've come just now, then, though I saw no reason why we needed to talk about it just before we ate. Surely, such grim news could've waited until we finished our lunch. I took my seat next to Laenor, as always. Laena sat on the other side of the table next to Mother, while father sat at the head of the table.

The Old King he'd spoken of was King Jaehaerys, the first of his name, who had ruled the realm for fifty-five years. The conciliator, the wise. The King's epithets were proof enough of just how beloved he was, for his reign brought a long time of peace and prosperity.

Except for my family, that was. We had not much love for him after he snubbed my mother and older brother's claims to the throne. Though I found it passingly funny that father was the one who took the most offense, more so than Mother and Laenor.

"This mean cousin Viserys is king." Mother said with a barely visible frown. Her long black hair was raised in a bun, and her poise was perfect. If things had been different, it was she who would've sat the iron throne, and I'd be a prince. "We should attend the funeral and swear our allegiance to cousin Viserys. As soon as possible."

Father looked at her. His rich purple eyes were as sharp as ever. "Are you sure, dear?"

"I might not agree with the Old King, but he was my grandfather still. Besides, Viserys was far more amiable by nature. What was refused by Jaehaerys might be accepted by Viserys." Mother answered. "It had been two years since the Great Council. It's nigh time for us to reconcile with him."

A silent conversation went between the two as they looked each other in the eye. Whatever it was they were scheming, both seemed to agree as father gave a firm nod.

"The Wayward Wind is already on the dock and ready to sail. A respectable ship for our family. As for the escort, I will gather four carracks from our navy. We can depart immediately tomorrow at noon at the latest."

He let his words settle before continuing. "Make sure to prepare suitably." Father said as his eyes roamed the room. When it caught mine, he added, "Especially you, Corwyn. This will be the first time we bring you to court. Keep yourself at your best behaviour, always."

"I will, Father." I answered. I knew I always behaved well, much better than the average five-year-old, but Father was nothing if not strict. "I will not shame our house." I returned to my meals. Baked crabs tasted best when they were still warm and soft.

Laenor elbowed me a bit on the arm. When I looked at him, he nodded to the window. A gesture that meant he wanted to talk with me later.

I nodded and continued with my food. All this talk made me hungry.

"Father and Mother have not given up." Laenor began. His long silver hair flowed unbound as the sea breeze flowed. "Even now, they still dream of the throne. Why they insist so much when it won't be them who sit there is beyond me."

It was a habit of ours to talk as we walked across the castle. I didn't know when it began, but Laenor liked it well enough. He felt more adventurous today, which was why we were moving up the ramparts.

The dock was visible from this high. Ships from two continents made port in their harbor. From the top of High Tide's walls, the entire city of Spicetown was visible. I imagined the sight would be even wider atop the watchtower, though Father forbade me from climbing them.

High Tide was new as far as castles went. It was Father who built it with the wealth he won on his many adventures. The castle was only finished shortly before Laena was born. Built from pale marble, its white walls and many towers almost gleamed under the sunlight.

"When have they ever given up?" I shook my head. "It's the duty of every lord to improve their descendants' lot. Is there any greater prize than marrying the royal family?"

"No." Laenor answered. We passed a group of soldiers manning the walls, which bowed as we passed. Proud Velaryon's seahorse was visible on their tabards. "But it's still a bother. You're too young to remember how grumpy they were when the result of the Great Council was announced."

I just hummed noncommittally. I was barely cognizant two years ago, and my parents didn't bring me to the Great Council. "Perhaps I should visit the sept and pray for the Old King? Even if father misliked him, he still brought peace and plenty to the realm. He deserved that much, surely." Whatever my family thought of him, he was still a most beloved figure in the realm, after all.

"You've been praying a lot lately." Laenor's brows furrowed a bit. "Not thinking of joining the Faith, are you?"

I laughed. "Hardly. I'd rather be a warrior or sailor instead." The life of a septon was respectable enough prospect for us second sons and the like, though I found the rules far too restrictive for my taste. Fortunately, my family had no shortage of gold, that they'd be desperate to ship off their excess son to the Faith.

"There was nothing wrong with expressing your gratitude to the gods, brother." I said instead. "Nor is there anything wrong with praying for your king's soul."

Truth be told, I was never a pious man, in either of my lives. However, I was not foolish enough to deny spirituality altogether. The fact that I remembered two lives was proof enough that there was something beyond this world, and The Seven were as good as any other place to begin looking.

Am I here merely because of happenstance, or was it part of a greater plan?

I'd like to think I was a part of some grand plan, of course, though for all I knew, the memories of my previous life were simply the result of a divine clerical error.

"That's not the only reason I sought to speak with you. I meant to tell you something else, namely that all your nags finally work. Father said you can start your training soon." Laenor frowned. "He should've told you himself back then. The news of the King's passing must've occupied his mind."

I nodded. "Good."

Laenor laughed. "My brother, the five-year-old brute. I don't know why you're so eager to practice swordwork. Boys your age would be better off playing with friends. Maybe learn your sums and letters if you need to study something."

I shrugged. "I already know my letters. I can read anytime I want." I felt my eyes drawn to the eastern sea. "And we don't have plenty of highborn children to be my friends here."

"True enough. This island is very limited in that regard." Laenor agreed. I trailed behind him as he walked down the stairs. "Who knows, perhaps you can be the warrior that I never could. Our ancestor Corlys was the first Lord Commander after all." He glanced at me. "Is that what you're aiming for? To succeed Ser Ryam Redwyne?"

"Not quite." I said. "And it's not as if you lack the chance to be a warrior yourself. Perhaps if you ever tried harder than half an hour every week, you'd be a proper swordsman by now. You know it's not too late."

Laenor waved his hand. "You sound like Father. You know I'd rather play to my own strength. There's no point in learning swordsmanship when I have no talent for it. If I have a need for swords, I can just pay for them. My own swordsmanship skill hardly matters."

I grunted. "And you have a dragon besides."

"And I have a dragon besides." Laenor repeated. "Which reminds me. I should take Seasmoke out later in the day. He'd be the size to be ridden soon, and he needed the practice."

I raised an eyebrow. "He's barely the size of a dog, last I checked."

Laenor laughed heartily. "When was that? He's larger than a destrier now. Mother said he should be rideable in a year or so. That's why I ought to train him more."

"If only his rider is as diligent as the dragon." I said half-jokingly. Laenor's habit of giving things up quickly perplexed the family. If he perceived that he lacked the talent for something, then he'd stop doing it. I'd like to call him lazy, though perhaps the best description was that he lacked determination.

Perhaps if it was something that he was at least interested in, but I didn't even know if he had any interest other than seamanship.

His words had some sense, at least. A lord was, first and foremost, an administrator. A lord who knew his numbers would be far more useful than one who only knew how to swing a sword. What was a lord's strength compared to his dozens of knights and hundreds of men-at-arms? What were they compared to the might of a dragon?

Unfortunately, this was Westeros. The idea of a warrior aristocracy was alive and strong. All lords were warriors, and those who weren't were subjects of mockery. As the heir of the house, it was Laenor's duty to impress the family's strength on outsiders. Something that he didn't care about. He'd do better in a world where the nobility were merely idle landowners, but not Westeros.

This was a well-trodden topic between Laenor and the rest of the family. If neither Father nor Mother could force him to do what he didn't want to, then I doubt I could. He inherited father's stubbornness, in that regard.

Besides, he was young, still. There was time for him to fix his childishness. Or at least for him to earn renown somehow so that no one would begrudge his lack of martial skill.

I listened to the distant calls of seagulls. "Do you still dream of sailing?" I asked.

Laenor smiled and ruffled my hair. "We are Velaryons, little brother. Seawater flows through our veins as surely as blood. I'll make my name as a great a sailor as father someday. To see the sights unseen and claim wealth beyond wealth, just like he once did."

So we returned to our favourite topic, as Laenor started talking of ships and seas and adventures.

On the morrow, the Velaryons took sail.

Driftmark's smallfolk watched as we boarded the ships and shouted praise to my father and mother. Genuine? Perhaps not, but at least it proved my family was greatly respected on this island. We waved and bid our farewell, and soon enough, we departed for the sea.

The five sailing ships brought by Father were built for speed, and even then, travel to King's Landing would take six days at the fastest. I was surprised my father didn't bring half his fleet with him. Five ships were downright humble for him, and Corlys Verlayon was not a humble man. What better way to impress than a large fleet?

At least the travel would be quicker than if we brought half a fleet. Truth be told, it would be even faster if we rode Mother's dragon. However, that might not be the most dignified way of traveling. All five Velaryons cramped on a single dragon, with no retinue of guards, servants, and bards to accompany us. We'd look like beggars, dragons or no.

Appearances must be kept, especially now.

I was busy staring at the cloudy sky above when I noticed a presence behind me.

"Nervous, little brother?"

I turned my head and looked at my oldest sister, Laena. She was six years older than me and was fast approaching maidenhood. She looked almost like the spitting image of Laenor. Her nose was slimmer, and her jaw softer. However, put her in a man's tunic, and few could tell the difference.

Not like I'd say it to her face, of course. I wasn't so tactless.

"No." I answered. "More curious than anything. I've never left our island before. Nor have I ever set foot on a ship."

In this life, at least.

"It wasn't as exciting as Father puts it," I added.

My sister sighed. "Here, I was hoping to finally see some excitement from you." She shook her head. "This is Father and Mother's fault. They're always too strict with you. It's alright to be a child, you know? You can be grim and serious all you want once you're old and married."

I kept my face as flat as possible. "Laena, my beloved sister. Please. This is me being a child. See? Look at the childish gleam in my eyes as I take in everything around us. All the eager curiosity I displayed since we left the island. How's that not childish enough?"

Laena snorted. How unladylike.

I considered it a successful deflection, once more.

It didn't escape my family's notice that I didn't behave like a regular boy. Thankfully, they chalked it up to my natural precociousness and proper education instead of me having a memory of a previous life. I was grateful for that, as I didn't fancy wasting years of my life acting like a child. Not like I remember how to behave like a child. I suspected my family was equally grateful their second son wouldn't be a trouble to raise.

Laena sat next to me. "I've seen old men with more sense of wonder than you, Corwyn. Mark my words, I'll make sure you'll enjoy your time there."

"We're to attend a funeral. We're not supposed to enjoy our time." I shot back.

"We'll stay there long enough until King Viserys' coronation. Do you think there'll be no merriment to mark the occasion?" Was her answer. "And mayhaps a tourney too. It would be unseemly to have one immediately after a funeral, but not long afterward." She said, as she decided this was the perfect time to pinch my cheek. "You have a very pinchable cheek, you know that?"

I swatted her hand. "I've never seen a tourney before. Father never saw fit to organize one in driftmark."

Laena rolled her eyes. "Of course he didn't. Our knights ride ships more often than they do horses. Tourneys would be a waste unless the occasion truly calls for it."

"So we never have anything worth celebrating in Driftmark? Truly?" I asked.

"No. We have tourneys to celebrate my and Laenor's birth. Yours too, though you won't remember. We didn't have many knights present back then, as most of them were preparing for King Jaehaerys' tourney." Laena said.

I've heard of that. The grand tourney to celebrate Jaehaerys' fiftieth reign. It was the biggest tourney in a century, as men put it. However, thinking of it brought something else to my mind.

"You visited King's Landing before." It was not a question.

"Aye, on our way to Harrenhal. Just two years ago." She was silent for a while. "You should see Harrenhal one day. It was impressive in a way that's difficult to describe."

I stretched my arms. "Neither you nor Laenor spoke of your time there often." I said, tilting my head where Laenor stood on the bow, pretending he was the captain.

Laena smirked. "I was young, and Laenor younger still. You were the youngest and were not even brought here." She said. "Do you know King's Landing is twice, if not three times larger than Spicetown? It was said that half of the world's wealth passes through its many markets daily. The goods you can find there easily outstrip even Spicetown. I hope Mother will allow us to sightsee a bit."

I noticed she was deflecting the conversation away from Harrenhal, so I pressed. "How about Harrenhal and the Council, then? No anger that your claim was ignored because you're a girl? Or that Laenor's was dismissed by the lords of the realm because his claim came from Mother?"

Laena laughed.

"Only Father and Mother care about that. I love them dearly, but sometimes I think they're too grasping for their own good." She said it in a low voice. It would do no good to have someone overhear us, even if we were surrounded by no one but Velaryon's men. "If you're curious about the council itself, then I say don't bother. It's just us listening to old men babble about nothing for days."

It seems that ambition is not something we siblings share.

I must admit, I was a bit wary when I found out where I was reincarnated. A family of ambitious upstarts and enough wealth to beggar most kings? That sounded like a recipe for disaster. I was almost afraid our overreach would see us branded traitors one day and lose everything. Such was a common tale in the history of both my lives. Though, fortunately, I found my family wasn't as far gone as some of those examples.

The fact that such an ambition was not only common but expected in Westeros was another source of concern, but that was a problem for another day.

"I thought you'd be more bitter at least. Father and Mother think it's a very important matter." I said.

"We have plenty as it is, and I'm content with what we have. A loving family and wealth to rival the Lannister's mountains of gold? How many lords can say they own half as much?" Laena said, her eyes to the distant west.

Few and far in between, I thought. Yet for some, it will never be enough.

Instead, I raised an imaginary glass with my hand in a mock toast. "To a good life."

Laena followed my mock toast. We continued our conversation afterward, though it was mostly Laena speaking at length about various landmarks of Westeros, the stars and constellations, and historical trivia she liked, and me listening intently. True, she wasn't as adventurous as Laenor, but Corlys' blood still flowed thick in her veins. She spoke of her planned tour of the Seven Kingdoms and the Free Cities. A topic she always loved to share with me.

Meanwhile, I spent the time thinking about my life and family.

My life was perfect enough as it was. We were nobles, and more than that. My family was recognized as the richest house in the realm. Our influence was matched only by a few. How could anyone call themselves our equal when my mother was a princess of the realm and we have two dragons to our name?

As the second son, my responsibilities would be few, and I'd be free to pursue my own interests to my heart's content. I'd be expected to further the family's interests as well, of course, but I have choices on how I'd do that, unlike Laenor. It would be a good life, I know.

I watched as the sun was beginning to set until it turned the west horizon purple and red before making my way back to my cabin.

The sunset at sea was very beautiful.

The days went peacefully.

Almost too peacefully, in truth. It took me two days before I realized there was not much to do aboard a ship for a passenger.

Was that why sailor tales always have storms and pirates? Because untroubled sailing was indistinguishable from sitting down and doing nothing? Now I knew.

I've spent those days bugging the rest of the family. I talked with Mother about the Targaryens. Laena about the city. And Laenor about ships. I even talked to some of the crew, just to know why they pulled this rope, pushed that crank, or which wind was which.

Father seemed to believe my boredom-induced curiosity meant interest in seamanship and thus spent his spare time lecturing me about all the intricacies of sailing the seas. I decided to rope Laena and Laenor as well, for the sake of fairness. Besides, both of them always loved the sea anyway.

I must admit, it was more interesting than I gave it credit for. Father had a talent for making his lectures captivating. That was a better way to pass the time than staring at our flag overhead. Father's time as an adventurer was long in the past, yet his passion still burns as brightly as ever.

Days continued to pass, and before I knew it, the time of our arrival came closer.

I woke up groggily to the sound of knocking on the door, accompanied by shouts of sailors rumbling above me and a flurry of activities as many pairs of feet moved from here to there.

I yawned.

"It's not even dawn yet." I grumbled. However, I made my way to the door anyway. There was only one reason why someone would wake us up at such an ungodly hour. Behind me, Laenor was already awake and busy rubbing off sleep from his eyes. Laena was still sleeping like a log.

Space was always a precious commodity in a ship, and we didn't have enough spare cabins for each of the Velaryon lordlings and ladies, so I shared the cabin with my siblings, while the best cabin was given to my father and mother.

The knockings grew more insistent.

"Alright, alright. I'll open it." I said as I trudged my way to the door in the dark dawn.

I found Mother standing outside, looking as if she had just finished her afternoon tea. She had even dressed herself properly, though her long black hair was still undone.

Mother smiled. "It took you long enough. I was beginning to worry if I had to ask our men to hack the door open with axes."

I gave her a tired look. "You exaggerate mother. You barely knocked for a few seconds."

Laenor made his way to us. "What happened?" He asked.

"We're close to land. It will take an hour at most before we make port, so make yourself proper." She peered further inside. "And wake Laena up."

I didn't really need a lot of time. I put on my finest doublet and trousers, slipped into my fancy boots, and gave my hair a quick comb. Just on time too, as Laenor's kicks finally did their job to wake Laena, and now she was hoarding the room for herself.

I made my way to the deck with Laenor instead. The morning air was crisp, and the early sunlight barely peeked through the dark sky.

Laenor and I stood in a quiet corner of the deck, away from the flurry of activities. There we observed barely visible towers in the distance pierced through the morning fog, and then a large red castle on the top of a hill. I knew what it was, of course. The Red Keep was the home of the dragon kings. Purposefully built high above the capital of the Seven Kingdoms.

King's Landing was on the horizon.

AN: Hello, first-time poster here. I've always wanted to write my own story someday, so I decided to start a fanfiction as practice, and what's a simpler story to start than an isekai.

Well, it may not be a regular isekai story, however, as the MC didn't actually die. He just did an ASOIAF Choose Your Own Adventure and was immediately transported to Westeros with his memory of doing the CYOA wiped out afterward, along with all his ASOIAF lore. I did this because if he remembered the lore, he'd definitely try to kill Daemon, Alicent, and/or Rhaenyra at the earliest opportunity. There wouldn't be much of a story then.

For the record, I've never watched HotD. So I will use the books as the main source. Maybe I'll skim the show if I need some help with characterization in the future, but right now I exclusively base my fic on the books.

Reviews are always welcome.