A/N: Sorry for the slight delay. Been caught up with some things. But hope this was worth the wait.

Brandon IV

Brandon stuck his tongue out in a flirtatious manner at a passing septon, attempting to get his attention. But like he observed from the other whores near the Starry Sept, it was hard to entice septons. He knew that it was not because septons were trying to behave in a chaste manner, but because they did not want to be seen as such. He was not surprised that the septons, for all of their talk of behaving in a holy manner and beneath their richly-ornamented gowns, were as susceptible to the temptations offered by the world as any other man. And yet, they call themselves the messengers from the new gods.

As Kenzou Haru was still attached to the Reyne banners, who were making good progress and had just inflicted a major defeat on the remnants of House Lefford's bannermen, Brandon volunteered himself to scout out the enemy's defenses at Oldtown. From Highgarden, the main army made good progress advancing along the banks of the Honeywine while their cavalry gained a lot of the harvests from their raids alongside other plunder. Meanwhile, Orys Baratheon returned to the sea and had personally took control of ships that had cut off the mouth of the Honeywine.

But before they can actually attack such as a well-defended city like Oldtown, they needed to have a good idea on what they were up against. Konno Haru and none of his men could infiltrate the city, as their physical appearances would give them away, and many of the northmen were not exactly known to be the sorts to be discreet.

"But why do you want to do this?" Torrhen asked Brandon. "You are the Hand, the main councilor. There are those who will be more willing to do this in your stead."

"I am not one to spend all of my able years writing with a quiver. I recognize that I have to do that, but I do not intend to make that my entire life. Besides, I have seen you grow older from all of that parchment you wrote, and how sloppy you got with Ice," Brandon snarked.

Torrhen groaned. "I did not get sloppy."

Brandon gave him a toothy grin. "Only sloppy people will deny that they are so, for how could they know their own flaws?"

"Shut it." Torrhen rolled his eyes. "But I have to point out a few flaws in what you want to do. First, unless you plan to move to the south for the long term, you have not changed your appearance. You look like a northman and you certainly smell like one, if Autumn's licking your hands and face did the trick."

Instinctively, Brandon reached for his arms and sniffed. What is wrong with how I smell?

"Second, it will be near impossible to enter Oldtown through the traditional routes. They will closed the gates and patrolled the roads on the lands that they still control, while every waterway leading into the city will be watched. They will be able to make you out, especially if you bring Autumn with you."

Brandon sighed, as he knew that to be true and it would pain him to have to be separated from Autumn for even one moment. "If only Oldtown's guards are dumb enough to mistake Autumn for simple a large dog."

Torrhen ignored the jest. "Third, Oldtown does not acknowledge their new overlords in Prince Jaenyx and they have chosen to appoint their Hightower lords as the old kings. They will be on the lookout for scouts or anyone trying to undermine them, especially since they will have the support of the Faith of the Seven behind them. That means that anyone who they even think does not belong to Oldtown will be killed on sight."

Brandon raised his hand on that. "All right. I am touched for your concern for me. It makes me wonder on who was my mother really was while in Winterfell."

Torrhen rubbed his forehead, and Brandon knew that was his way of showing his annoyance. "Please do not make that jest. That is my mother you are talking about."

Brandon decided to push Torrhen a little further. "It makes me wonder who came up with the idea that only women were fit to be mothers."

"Brandon, please stop talking and let us focus on the matter at hand." Torrhen might have tolerated his continuous jests, but that did not mean that he liked all of them. That made Brandon more amused, but he did have to bring the conversation back on topic.

"As I was saying, I am touched at how much your worry for me. But for this, I think you worry too much and allow me to show how all three of your concerns should not be ones that you should break your back on."

"Is that really a good way to describe it? I do not break my break back on it," Torrhen answered.

"That is the spirit." Brandon patted his shoulder. "One, they might have the city well-defended, but there are always cracks in their defenses, so I should be able to find them. Two, once I find the gaps in their security, I should be able to enter Oldtown without much trouble and not have to take the traditional routes. And last but not least, I can easily change my appearances to not look like a northman."

Torrhen crossed his arms. "I'm intrigued. How do you intend on doing that?"

"Well, I will not be cutting my hair, since my hair is not to be touched." Brandon mockingly moved his hands through his raven black hair, which was flowing freely. "The most I will do is shave, which will make me indistinguishable from how other women look."

"Women? Wait, you are not suggesting—" Torrhen asked knowingly.

"Yes." Brandon nodded his head eagerly while he did put some thought on how he would look. "I will dress like one of the whores in Oldtown and try to entice someone of high rank there with my wiles and beauty."

"You might be handsome, Brandon, but you are not beautiful," Torrhen pointed out.

Brandon gasped in shock, as if offended that his own brother thought little of his physical appearances. "How could you? But then again, some other shit might not have as poor taste as you do."

"Hey!" Torrhen pointed his finger at Brandon. "Let us not get into talking about Jocelyn. Besides, she is hardly a plain woman, if you need reminding."

Brandon shrugged. "I did not mean to insult my goodsister, but going back to my point, me dressed as a whore might not be as crazy as it sounds. I have my ways of getting information and I will be safe there."

"But even if you do manage to get in there without trouble and also get what you need, there is no guarantee that you will be safe there indefinitely. You might not be able to get out until we storm the walls."

"I will take care of that. And you know me, Torry. I am not going to let myself get hurt or maimed."

"And regarding how you will get information back to us—"

"Let Prince Jaenyx handle that. I am sure that he has ways of dealing with those matters."

Torrhen saw there was no way to persuade Brandon otherwise, as he knew that once his brother was set upon nothing, he was indeed the direwolf in that all of his focus and energies were focused on that.

"Well… it is your choice, Bran. While I learned long ago to eventually let you do as you wish, will your dragon friend allow that?"

"Let me handle Rhaenys, Torry. You just worry about getting our northerners ready for a hard siege."

As expected, Rhaenys, Aegon, Jaenyx, and Visenya were all confused as to why Brandon would want to endanger himself so needlessly.

"You are our Hand, Brandon," Rhaenys stated. "We do have men whose sole responsibility is to collect information."

"Like who? The Harus?" Brandon shook his head. "With respect to them, I do not think that they will be able to do what is needed."

"And why do you think so, Lord Snow?" Jaenyx asked. Brandon knew that he would be offended at someone doubting the abilities of the ones he considered the closest thing he had to a full family besides his Leniar cousin and the Targaryens.

"There is one obvious reason that they would fail in any scouting of Oldtown and that is because they hail from Yi-Ti. Any foreigners or anyone who does not belong to that city will be hunted down and arrested, which will defeat the purpose of any Haru man sent on a scouting mission to the city. As for me, they will only see someone dressed like a woman, allowing me to right under their noses."

"I knew that you were crazy, Lord Snow, but that is on another level." Aegon seemed to admire Brandon. "And it is so crazy, it just might work."

"That is why, Your Grace, that it will work. And I will be staying under their noses for so long that I will be able to gain much knowledge about the defenses of the city. And given Prince Jaenyx's expertise in information gathering, it should not be hard to figure out how to get what we need between the lines."

"But how long do you intend on staying there? Surely, you cannot think of staying in Oldtown until we storm the walls. You will be at risk also," Jaenyx said.

"I will stay for as long as it is necessary for me to get what you need, and I shall play my part should you need something else to happen," Brandon added.

"What do you mean by that, Bran?" Rhaenys asked.

"Who says that the Haru men are the only to take something from within?" Brandon asked.

Jaenyx bobbed his head. "I see. You want to lead a raid from within?"

"Eventually, I am considering it. As you all should know, we should not approach objectives like Oldtown with a hammer approach. We have to be smart about it, be efficient about our approach, just like we have been doing so far. We cannot act as the enemy expects us to do, which we must continue doing. And we also have dragons in the air, so we can always keep the enemy guessing."

Visenya smirked. "Indeed. And you have shown us to be an unconventional and yet effective figure so far. Let us see more of that."

That night, Brandon trimmed his beard and then scratched Autumn's head. "Hey. Listen, I have to go somewhere soon, but I will be leaving you with Rhaenys. You remember her, right?" Autumn licked his face. "I thought so," he chuckled. "You will be fine without me, but when we see each other again, it will be great. We will both do something that none of us has ever thought of doing. It is because of that reason that I know it will work."

Brandon's first thought was to leave Autumn with Torrhen, but considering that he had to lead the army and Jocelyn was coming from Dragonstone with baby Alys, he had more important matters to pay attention to.

Brandon led his red direwolf to Rhaenys' tent, where she and Valaena were tending to baby Prince Daemon. "I hope I am not interrupting anything."

"Not at all." Rhaenys then approached Autumn. "Hi, there. I am going to be taking care of you for now." To his relief, Autumn remembered to be calm around Rhaenys and allowed her to scratch the ears. "He still likes me."

"Just be gentle with him," Brandon reminded her. "I will be back soon. Count on that."

"Of course." Rhaenys hugged him tightly. "Just be careful. Baby Alys has to have her uncle be back in one piece. And do not go jesting with whoever you try to take into your bed. They might go crazy from your mouth alone."

Brandon winked at her. "Well, that is if they can last through the first word."

Brandon shaved his beard, but his bare face made him very uncomfortable at how… unnatural it looked. Part of the appeal of the First Men was their overall unkemptness, which fitted their belief that they had nothing to be ashamed about regarding their appearance. More weak-minded people cared too much about how they looked, while the First Men believed in the true value of a person being in how they were at heart and not what others could see with their eyes. But that was a discussion to be held at another time.

Then, Brandon discarded his furs, tied his hair, and put on a dress loaned to him by Rhaenys, who then made him more "presentable" by stuffing his chest with rags that would make him look like he had the biggest teats in Westeros and tied the dress tightly around the waist. Brandon coughed at how firm the knots were.

"I guess I finally know the pains of a woman every time they have to wear something like this," Brandon remarked.

Rhaenys shook her head. "No, you do not. The only way you will understand is after you decide to cut off your balls and have men try to grab your ass, but both is not likely to happen soon."

"Do not tempt me. I can just grab a knife and do the deed myself," Brandon jested.

Rhaenys gently slapped his chest. "Perhaps I can have Meraxes do that for you, although it might be tricky to move her teeth between your scrawny legs."

Brandon chuckled nervously, the thought of a dragon doing exactly quickly giving him an uncomfortable feeling. "All right. I see your point."

"But still, be safe and do not do anything rash."

After saying his goodbyes to Torrhen and the others for the time being, Brandon then moved far along the northern bank of the Honeywine, bypassed Brightwater Keep, and then moved southwards from Blackcrown towards a boatman that he had hired. Of course, he had to be on the lookout since there would be those who would question a woman traveling alone, so he had to keep off of the main routes before getting onto the boat.

Brandon sat the bow of the boat and assumed a higher-pitched voice to disguise himself. "Can we no go faster, good ser?" He had to learn how to speak like a southron after hearing how the others spoke.

"Not on these fucking waters, we will not, fair lady," the boatman answered.

The sooner we get into the city, the sooner I do not have to wear this tight dress, Brandon grumbled.

"Where are you from, if I may ask? You do not seem to be from around these parts," the boatman asked.

"I am paying to get me through to Oldtown, not do small talk," Brandon reminded him.

A few more hours and Brandon could hear more people's voices in the distance. We must be close. "How much further?" he asked the boatman.

"Just a few more turns and we will be docking shortly." Then, a group of horsemen arrived at their left side on the bank, as if expecting the boat to come. "Shit," the boatman cursed.

"What is going on here?" Brandon became very worried.

"Just stay in the boat. It should not be long." The boatman moved the boat near the horsemen, got off, and walked up to them.

"Sem, what do you have for us now?" the lead horseman asked.

"Good sers, it is the same thing as always. It… has been a long season," the boatman answered back with a nervous voice.

"Who is she?" the horseman asked the boatman. Brandon could tell that he was eyeing him more than what was normal.

"She is my wife," the boatman said as he used the cover that Brandon paid him to say.

"She looks pretty." The horseman dismounted and whispered in the boatman's ear after coming up to him. Thanks to Brandon's days of hunting, he was able to hear clearly what the horseman was saying to him. "I will give you thirty pieces of silver for half a day with her. She looks nice."

The boatman chuckled nervously. "I do not think that you will like her and even though we have done deals before, she is not part of them."

"I am changing them. I would like to spend some time getting to understand how such a bastard like yourself was able to catch someone like her." The horseman then pushed the boatman aside and then approached Brandon. But before the horseman could get his hands on him, he drew his dagger and cut across his throat. He was dead before he hit the ground.

The other four horsemen were alarmed at the seeming woman being able to defend herself, but they were caught off guard by Brandon charging them and grabbing the dead horseman's sword. Throwing his dagger at the second horseman's neck, he parried the third's lance with the blade before decapitating him with some swift swing. The two other horsemen dismounted and tried to attack him with their axes, but Brandon showed that he was the superior fighter by using the lance and pushing them both back with the force of the shaft. Brandon then grabbed his dagger and slashed across the fourth horseman's neck before he could get up before sticking the sword into the chest of the fifth one.

Brandon took a deep breath and surveyed the carnage he wrought. This was not his first time killing and he had been in the thick of battle many times, but he had to remind himself of how quickly things could go wrong and this was the fastest that he took down five men. And he did it all without Autumn's help.

Brandon turned around and saw the boatman trembling with fear. Although killing random men was not what he would do, he had to show the boatman that he meant business.

"Please do not kill me. Please do not kill me," the boatman begged while Brandon grabbed his collar.

"Quiet!" Brandon raised his voice. "Or you will make do that."

The boatman gulped. "Just who in the Seven Hells are you?"

"I am someone who will make things very difficult for you if you do not get yourself together."

The boatman pushed his hands away while shaking his head. "No, no. This was not the deal. I am done now. You find yourself another boatman."

Brandon had to admit that he was impressed at him showing courage for once, but that was not going to serve him now. He brought his dagger to his throat. "Now, you listen here. You have two choices. One, you get me where I need to go, you will be rewarded and you will get your boat back. Or two, you resist and I have to kill you before I take your boat. Which do you prefer?"

The boatman chose the former, which would explain why he just went back to his boat and rowed.

Finally, Brandon entered the great city of Oldtown. From what he knew of the city, Oldtown was a labyrinth of wynds, crisscrossing alleys, narrow crookback streets, and markets. These include the Thieves Market and Ragpicker's Wynd., with the entire city built in stone. All of the city's streets were cobbled, which can make them wet and slippery on a damp day. Most of the bridges were made of stone as well, although some wooden bridges can be found also. The city itself was surrounded by massive, thick, high stone walls. People said that Oldtown could be described as smelling as flowery as a perfumed dowager, whatever that meant to Brandon and any other outsider. During the summer, it steamed and sweltered during daytime but came alive at night, but as it was nearing the end of summer, the city's activities became more sparse. But in the meantime, visible foliage include melons, moonbloom, nightshade, peaches, and pomegranates. Just to be sure that they were ripe, Brandon sampled them. Well, how many fat northmen would we have if White Harbor was like this?

Many small isles were located in Oldtown. The river road wound along beside the Honeywine through the heart of the city. West of the river, the Guildhalls lined the river bank. Rat pits and black brothels are located in the undercity, which Brandon imagined that he would have to venture to in order to conduct his work.

The Citadel, home of the maesters, was located upriver on both sides of the Honeywine. Boys and men gathered there from all over Westeros to learn, study, and forge a maester's chain. The Citadel is considered to be the greatest seat of knowledge in the known world, or to the limited perspective of the south. And with the influx of new knowledge, the Citadel might not be the center of books any longer. All because of Jaenyx Belaerys.

Brandon looked downriver, and there it was, the Starry Sept of the Faith of the Seven, which was raised on the command of Lord Triston Hightower long ago. It became the seat of the High Septons for a thousand years, which made the city the unquestioned center of the Faith for all of Westeros. The Starry Sept had black marble walls and arched windows, while mansions of the pious are located near the sept. That was where Brandon would have to do most of his information gathering, since only through getting close to the septs could he be in a position to do some damage.

Besides the Sept of Oldtown, at least seven more septs honoring the Seven, built on the command of Lord Damon Hightower, all of which could be found nearby. These include the Sailor's Sept down by the harbor, the Lord's Sept, and the Seven Shrines in their gardens across the Honeywine. Oldtown was also home to a motherhouse. And Brandon could see that down by the wharves were temples that catered to foreigners, such as Summer Islanders and red priests of the Lord of Light. However, looking closely, Brandon saw that they were empty. What in the seven hells happened to them?

Looking up, Brandon saw the mighty Hightower, a massive stepped lighthouse located on Battle Isle, where the Honeywine widens into the Whispering Sound. The Hightower had a great beacon on top, which shows ships the way to port. The Hightower was located on Battle Isle in the center of Oldtown. To everyone's knowledge, the Hightower was the tallest tower in the world, higher than even the seven-hundred-foot Wall. I doubt that, if anyone could make that comparison without ever visiting it.

Brandon then disembarked from the boat and turned to the boatman. He then pulled out a bag of silver and then gripped his hand tightly. "If you say a word to anyone on who I really am, I will make sure that you die slowly. Understood?"

"Yes," the boatman answered back fearfully.

"Tell the dragons and their armies that I came here safely. They will reward you again."

However, as Brandon moved his way through the city and towards the mansions next to the Starry Sept, he found that he actually did not know how a woman was supposed to enchant a man. And now that he thought about it, he was out of his game for a long time now. He was not dead below the waist, but he had more important stuff to handle and he found jesting with Torrhen, Jocelyn, and his nephews and nieces more worthy of his time. That was when he decided to just watch what the other whores were doing and copy them.

Old gods, let this work, Brandon prayed once he saw a septon finally approach him. I better not take my time and he must not know who I am.

A/N: Brandon is a troll as always, but him cross-dressing was also a way to feed his addiction to mess with people's minds. I mean, how else would you compensate for your abilities to greensight (I'm talking to you, Bran)? And Brandon is now in the belly of the beast and he's just snatched his first target.

This was shorter than most updates, but I hope this was a good read.

Next... what will happen to Oldtown?