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The Vengeful Lion of House Lannister

The MC is granted a 2nd chance at life, only to wake up as a young Tywin Lannister. Follow the MC as he finds himself as part of a scheme fashioned by a higher being. He will have the opportunity to relive Tywin’s life while attempting to achieve his objective. With hindsight of the plot from the books, the MC will not only try to emulate Tywin’s greatest successes, but capitalize on his failures. All while carving his place in the World of a Song of Ice and Fire. This is my first publication so feel free to comment. Lore and writing critiques will be considered. This is ASOIAF Fanfic, that means it is R18. Anything goes- Violence, murder, sex, rape, incest, gore and tragedy. If you are easily offended then start complaining to G.R.R. Martin as this is based off of his work to which I am a fan. I am only practicing my writing while immersing my MC into a world I deeply enjoy. *Not a sentient system. *He will be breaking from book canon, so be warned. *Current release schedule is at twice a week.

HungryWolf2024 · Book&Literature
Not enough ratings
19 Chs

9. A Good Day

It took less than 20 minutes by carriage from the Rock to Lannisport. Both Kevan and Genna looked excited, even if it been more than 2 dozen times, they had visited Lannisport over the years. This was the first time that they would be coming with big brother Tywin as their chaperone. To them it was like they were going on an adventure.

Genna didn't shut up the entire time, it was a good thing Kevan and I chose to ride horses. Mya wasn't so lucky, she rode in the carriage with Genna, but she didn't seem to mind. While I rode alongside, I was able to hear her, about how she wanted new dresses, combs, sweets and other deserts. When I spoke with Kevan he simply said he would see when he got there.

Maester Brayan came along as well, but he wisely chose to ride in the uncovered carriage. He had quickly become aware of Genna's chatty nature when she was excited. As we rode through the streets, I notice that the main street was very well kept, as well as patrolled by the city watch.

From a distance you could see a central keep, which was the home of House Lannister of Lannisport who were basically the Stewards of Lannisport. Adjoined to the central keep was also the garrison for the city watch. The Northern side was split between members of the Faith of the Seven, Lannisport being a headquarters for them in the Westerlands. Also in the Northern part of the city were the wealthier homes and also high-end shops such as jewelers, dress makers and goldworks

The central streets that ran east to west, and were mainly various shops and vendors and squares. Produce, seafood, and goods from, Old Town, Dorne, the Reach and some even as far as the Free Cities from the east. The central streets were vibrant and colorful and reminded me of a few open-air bazaars that I had visited in my past life whenever I had gone on vacations. 

We made our way to the city watch garrison where I met Laurance Lantell. He was the commander of the city watch. He was a portly man of average height in his late 50's. Tywin had met him before, once while attending a tourney at Lannisport. 

He tried to smile and act welcoming, but I could tell that the man was clearly annoyed. Our unannounced visit had probably interrupted whatever plans he had for the day. His mood did improve however when I complemented the city patrols and general cleanliness.

His mood improved further when I told him that he didn't need to accompany us as we were simply parking the carriages at the garrison. That cheered him up so much that the man even offered 4 city watchmen to accompany us and show us around. 

...…..

It was already mid-afternoon and I was tired, Genna reminded me why I hated going shopping with my various lady friends from my past life. She had made us stop at almost every dress and jewelry shop on a particularly long curved street on the north side. My men and the city watchmen had to be split up.

I sent Robar, 2 of my guards and a city watchman together with Kevan, to look around the various weapon and armor smiths. For once Kevan acted his age when he tried to run off when I gave him the go ahead. It didn't help that Robar also seemed to be excited as well and would have run with him if Garrand hadn't warned him earlier.

By midday Genna had finished her shopping, or at least the shopping she was allowed do. She had bought herself an assortment of dresses, hair ornaments and a couple of leather shoes and sandals, all paid for by me. This had put the biggest smile on her face.

While we had been shopping at one of the more moderately priced clothing stores, I had made Mya pick some things for her. She ended up with a dozen new dresses, new sets of undergarments. New pairs of shoes and accessories. The dresses were mostly blacks, greys and blues, with few other muted colors. I wanted her to look good but not stand out. The owner of the store assured me that the dresses she chose would accomplish that.

It was early winter at present but, here in the South, the temperature was still bearable. Rains would fall regularly so good foot wear was important so I got 2 pairs of boots for myself. I also commissioned new boots for my men and even the watchmen who had accompanied us.

Kevan had returned with a new finely crafted one-handed saber, that looked more decorative than functional and a new crossbow. He had looked rather pleased with himself. The saber was in my opinion, 'dope as fuck' and for a moment I wanted one to. He also came back with sweets for him and Genna as he knew I didn't like sweets, something both me and original Tywin had in common.

For lunch, we ate at one of the taverns on a main street that was famous for their seafood. I had treated the guards and watchmen as well. After I sent every one else off. It was only myself, Maester Brayan, Garrand and the men from the city watch. Everyone else had been sent back to Casterly Rock. Robar and my guards would return after dropping Kevan, Genna and Mya off.

In total I had spent around 29 gold and 6 silver moons worth. This wasn't bad, but my pocket was feeling it, I had come with 89 gold dragons' worth, now a third was gone. Even Maester Brayan had gotten in some shopping, I had sent him and a guard to purchase useful herbs and to also look for books. At least everyone had seemed to enjoy themselves, even the men, after all, I was footing the bill.

I had already discussed with Garrand this morning and agreed that 25 silver stags a month would be sufficient compensation, plus room and board for each of the guards who served under me. Most guards only got 15 silver stags a month. In return, they would have to go to King's Landing with me. I was a fairly good wage for single men.

Those who had relatives, parents and siblings, I would be able to make arrangements to have the pay-master issue portions of their salaries from Casterly Rock. So, they were even more motivated to serve.

...…..

It was now late in the afternoon and Garrand, Maester Brayan and myself were seated in a private parlor of one of the finest establishments in Lannisport; Helena's Delights. The city watchmen had highly recommended it when I had asked which was the finest establishment. Helena was well known by knights and noble men of the Westerlands, as they were the only ones who could afford her services. But I wasn't here to sample her delights, I was looking to make an acquaintance. Someone in her field would actually be able to offer resources and information for the right price.

"My Lord, please, I would advise that we leave, what would your Lady mother say if she found out about us being here?" Brayan was clearly nervous to be here, part of a Maester's oaths was celibacy.

"Maester Brayan, I am not stopping you from leaving, but what I will say is, Ser Garrand won't be telling anyone where we have been and nether will I. Now let me enjoy my small goblet of spiced wine, it has been a long day." I said while sipping from the gilded goblet and playing with one of my new daggers.

It was one of a pair. Fine 15-inch steel daggers, sharp as a razor and though not optimized for throwing, it could still get the job done at closer range. Garrand had approved of them and offered to teach me how to throw a dagger on the next time we trained.

Brayan had turned to Garrand with a pleading look but he simply gave him a toasting motion. Garrand already knew what was going to happen and he was along for the ride.

"Maester Brayan, I was going to ask you to accompany me to King's Landing when I leave next week. But if you keep insisting on acting like a maiden who had been caught being fingered by a bard, then maybe I should find someone else."

Brayan for the 2nd time in a week realized that he misspoke. "My Lord, my apologies, it is not that I ever intended to share that we visited this fine establishment, only that it may not be well for our, our reputations. " Finished Brayan.

"You should probably just tell our young lord, thank you for the opportunity and that you will accompany him. Either that or just turn him down." Garrand added.

"Yes, my Lord, I will be pleased to accompany you to King's Landing." Brayan quickly answered this time.

 "Very well, I will inform my father tomorrow, so that he can request a new Maester from the Citadel. Now, where is that Madame?" As if she had sensed that we were speaking of her, Helena with her sultry curves, salaciously made her was over to me and sat next to me. She was a buxom woman, maybe in her late 40s, straight blond hair. Her age only added to her appeal. She had aged like a fine wine.

As she sat in the seat next to me, she leaned in and I could smell her perfume, it wasn't overpowering, just enough to lure you in to want to take a deep breath. Her long straight finger reached out and caressed my face.

"Imagine my surprise when one my girls told me that the Young Lord of Casterly Rock came to my establishment. At first, I thought she was playing me for a fool when she started. A young lord, a knight and a maester walks into my brothel." She gave a seductive chuckle.

"But I am happy to see she wasn't playing with me. Perhaps this is your first time and you wished for something special. Or maybe if you don't mind a more experienced partner, I could make an exception. I don't usually entertain my patrons but on special occasions, as you are someone special indeed." She tried to seduce me but I was too experienced to fall for it, but I wouldn't lie, I was hard.

"Perhaps if you treat my friends well, you and I can have a private discussion about why I'm really here." This aroused her interest more than it had already been. "Ah, it's very rear that a man can make me curious after so long in this line of work." She licked her lips and then retracted her hands to clap them together. 

Through the back door came the figures of six beautiful women. Since coming to this world, these were among some of the most attractive women I had seen, all in one place. "Do you like my little delights? The reason I took so long before was that I was arranging a feast for your eyes."

 A feast they were, Brayan was practically drooling and Garrand was stun. The first 2 were clearly from the Summer Isles. They had athletic builds, their complexions were dark brown, small perky breast and curvy hip and thick thighs. Another was the dark tan of the Dornish, she was on the shorter side but her breasts were larger than the previous 2, her skin was flawless. 

The other 3 were a brunette, a blonde and a redhead, each with well-proportioned figures, with the exception of the redhead, who was slightly thicker. She had the biggest ass of all of them, and her proportions rivalled that of Helena. They were all beautiful in their different ways. By Earth metrics, they would be between 9s and 10s. 

"Well, what are you waiting for? We need to be back by later tonight." I snapped Brayan and Garrand back to the present.

"Might I make some suggestions if your companions are hard for choice and your time is limited?" Helena spoke up, while now leaning with her elbow propped just over my shoulder. This allowed me to get a very close view of her cleavage, her dress's bodice so low that I could just make out the top of her areolas.

"Certainly Madame, I am confident that you would best be able to assist."

"Very well, Azari and Alian, why don't you give our strong knight here something to remember. Katherin, Dyanne, try not to break the maester, be gentle, but not too gentle."

As the 2 Summer Isle women took Garrand by his hands and lead him away, the redhead and the Dornish pounced on Brayan. The redhead had circle from behind him and licked the back of his neck while the Dornish had grabbed him by the collar of his robe and tiptoed for a deep kiss. The blood from Brayan's brain had already left and gone to his cock as they dragged him off.

That left me and Helena alone now, something that actually made me get excited. I knew that it was the body that I was in now, as experienced as I was, this body was clearly going through puberty. Any stimulus would be enough to arouse it. I needed to put my proposal forward. 

"So, what is it that you really want?" She asked as she looked at me with her blue eyes.

"You have been running one of the most successful pleasure houses in Lannisport for the past 2 decade. You are woman who is clearly discreet. For that I wanted to make your acquaintance." 

"And, is it just for that, that I owe the pleasure of your visit?"

 "No. I also wanted to procure your services. I want you to find me 2 girls. Pretty. Young, between 10 and 5 to 10 and 8. They must be reasonably smart and have some experience, not roughly broken in. I will be taking them with me to King's Landing. Do you think you can manage that?"

She responded with a dainty chuckle before she looked at me again. "I know that you are a young noble, but you do realize that I do not deal in slaves. I am a brothel madame, each of my girls could walk away from me at any time they want. I can't make any of them go with you."

 "Nor do I expect you to. What I want is for you to introduce me, and I will handle the negotiations."

She thought for a second. "I think I may have just what you want. I know 2 such girls, give me until tomorrow and I will be able to introduce you. But let me ask you this Young Lord Tywin Lannister, what do I get in return for my services."

"You get the friendship and gratitude of the Heir of Casterly Rock." I bluntly stated.

Her response was that she wanted to scoff but didn't want to risk offending me. It was plain as day as she had retracted her arms and folded them over her breast like a child that had gotten coal for Christmas.

I had pushed my little jape far enough, when I pushed my hand into the inside pocket and pulled out a pouch. This got her interest when I extended my hand. Her eyes almost turn from blue to gold when saw the contents.

"50 gold dragons upfront. I would not expect you to give your services to someone you have only just met, for promise of future benefits. I hope that we can have a very long prosperous relationship in the future." 

This caused her to give me a predatory smile. "Oh, this helps you more than get into my good graces. You could have all of the girls in here for this much as well as me. The things I could teach you, the pleasure I could let you experience. Unfortunately, I have never had a boy as young as you? For 10 I had expected to be more excitable, even a little naïve. Instead, you didn't give me a chance to entertain you before you got right down to business."

"Well, if you like, you can still entertain me, if you want. I understand that I still have a lot of growing but I wouldn't mind if you tried. My cock has been aching since I saw your entrance. I think I won't be able to walk back out properly without your help."

 "I shudder to think what you will grow into. If only I was 3 decades younger, I would have given you my maiden head with no regrets if I could simply bed you." With that she had slid down off of the seat while throwing a small pillow on the floor in front of me. "My young lord, I can see that you are already familiar with matters of carnal pleasure. I am not certain that you are too young to experience someone of my skill. I will give you something that you will never forget." She said a she knelt.

Her fingers slid up my legs as she licked her lips. With a deft hand she reached up and undid my trousers and pulled them down to free my cock. It was already leaking at the tip. All 4-inchs stood on display. It would be a lie if I said I didn't feel a little dejected.

"My aren't you eager." She said just before she licked the tip, tasting it before she slowly swallowed me whole. To call her a pro would be to undersell her skill. The warm moistness was almost unbearable. I felt my core tighten as my eyes rolled back.

As much as tried to maintain my composure, I couldn't fight biology. The sensation was too much for me to handle. The hormones in my body were driving me, my hips started to move on its own. I began to try and push deeper but this only amused her. A woman of her experience was clearly accustomed to bigger. She enthusiastically accepted everything, never once taking me out.

I felt it, it was the first time this body would experience blowing my load and it was glorious. My heart was racing, my veins were pumped but she reminded me who was really in charge right now as she had slowed her rhythm down. As I had looked down, she made eye contact with me. With that she had me. She began to speed up.

I could feel the pressure had built up as much as it could and then when I felt it. I couldn't help it as she allowed me to grab the back of her head and with the final pumps, I shot my load into her mouth. When I had regained my senses, I looked back at Helena, she had never stopped sucking and was now slowly massaging it with her tongue back into erection. 'I'm in danger.'

...…..

Garrand, Brayan and myself sat in the back of the carriage together with the stuff we had purchased in the evening. As we approached the gates of the Rock, neither of us had said a word on the way back. Each of us had different experiences that evening but it was still the same, we would certainly not forget and I could tell that it was money well spent. All in all, it had been a good day.