Disclaimer: I do not own anything related to The Vampire Diaries, TV show or books. However, I decided to have a little play around with the characters (I would definitely like to play with Damon).

I have replaced all of the chapters up until chapter 10 with modified versions to align them more towards TVD mythology. I have changed the nettle juice to vervain and mystifying to compulsion. The story was not initially meant to be a fanfic, which is why the mythology is different. I will also keep the method of turning the same for this story. Extended mythology is remaining and how compulsion and vervain work will differ slightly because of my story rules. My feelings are that the story is too far away from TVD mythology to really qualify as a TVD fanfic. If you have been reading the story and suddenly notice the changes, I have amended the first 10 chapters. This message will be posted on the first 11 chapters only. I hope this makes the story more enjoyable.

Damon is finally back in 1530.

Warning there are some vulgar moments in this chapter, it also contains bad language, sexual references and death.

When Damon came to his senses, he was crouched down on the floor, therefore the first thing he noticed as the foul smell. He was surround by the stench of sewage. At this, he opened his eyes and allowed them to adjust to the dim light which surrounded him. He was still in the cellar, but the room looked different. There were wooden barrels stored up to the vaulted ceiling and the door which had previously covered the non-existent hole was now a grate covering what was clearly a chute as daylight shone down, albeit dimly. The smell wasn't just of sewage, he noticed a fusty, damp odour, clearly caused by the open grate. It was then he realised what the open grate would lead to, and just as he thought it, he heard a squeak and the sound of tiny pattering feet. Damon looked towards the noise and saw a large rat running across the floor.

"I haven't missed you guys." he shook his head. "Well, it seems like I'm in the right place." he added, getting to his feet and brushed away the dirt from his knees.

Damon made his way to the grate and peered through the chute. It would have been a difficult climb for a human to make, but due to speed, it would be no trouble for a vampire. He searched around, looking for the latch to lift the grate as he didn't want to break it and bring attention to his presence. It only took a couple of seconds before he managed to lift it. Damon climbed into the chute and vampsped to the top, emerging into the grey and cloudy September morning daylight. He checked the bag on his hip and felt the shape of the chest inside. Assured everything was complete, he crept towards the small alleyway which would lead him to the world outside. He poked his head around the corner and took in the sights, sounds and smells of 1530.

Initially, the buildings he could see directly across from him were almost identical to how they had been almost 500 years into the future. They were much newer and decorated in a different manner; the pavement in front of him was gone and replaced with just dirt, however for the most part, the street looked almost the same, although the buildings appeared to be cruder and newer. The sounds and smells on the other hand was a different matter. Gone was the sound of traffic and trams. Instead he could hear the wheels of carts and the neighing of horses. The smell of pollution no longer clogged the air, however the smell of manure and sewage replaced it, causing Damon to wrinkle his face in disgust.

Noticing the street was momentarily quite, Damon slipped out of the alleyway and managed to make his way towards the the docks, following the crowds. Once out in the open and near the river, he could seen the huge differences between the city he had viewed only a couple of hours ago and what was in front of him now. The roads around him were either cobbled or mud. The lively bustle of sailors preparing their ships. Damon knew he needed to get his bearings and find out where The Temptress was moored. Making a mental note of where he was, he spotted a man getting off a boat and decided to approach him.

"The Temptress?" Damon asked, however the man shrugged, clearly not understanding what Damon was saying, so he decided to head north, just as Esther had told him.

Damon had lost count of the ships he had walked past. Different ships of varying types and sizes. Some clearly owned by wealthier merchants, while some were simple fishing boats. The number of fishing vessels in the area impacted the smell and the odour was foul. Yet in a strange sense, Damon felt a relief, despite the horrible smell, the industrial revolution had yet to hit and everything was natural. Man hadn't begun to destroy the climate at this point. It was incredible, he mused, that in the span of 500 years, man would decimate the animal kingdom, ruin the air quality and destroy fauna and flora in the pursuit of consumerism. Damon was himself just as guilty as anyone as he liked his high end products. However, this was the first time Damon had actually thought himself as someone who wanted to help stop climate change. However, that was for another day and maybe a new mission for the team. In the meantime, he had his own agenda, which was to find his ship.

As Damon walked past the medieval prison Het Steen, he noticed a man dressed almost exactly the same as himself, which wouldn't have been strange in 2019, but men as wealthy as the Earl of Hallamshire were a rarity. Not only that, the man could have been Damon's double in appearance. The only difference was Damon's hair was shorter and in Damon's opinion, the other man wasn't anywhere near as attractive as himself, he didn't have the X-Factor that Damon had. Curious, Damon edged a little closer and noticed he had a man with him, who was carrying his goods and appeared to be readying them to be loaded on a ship while the man held back in the shadows, as if not wanting to be seen. When Damon looked up towards the glorious ship, he noticed it was called The Temptress. Although he couldn't be certain, Damon had a sneaky suspicion the man in front of him was Edmund Spicer with his manservant Matthew, who looked to be a muscular lad, with blond hair and bright blue eyes. He listened in to hear them speak, just to be sure he was right, any conversation might be a giveaway to whether they were who Damon was looking for.

"Is there anything else to take up mi'lord?" the blond haired man asked.

"Not yet Matthew. You are the one who has been dealing with the captain, he only knows your face. If anything else needs to be loaded later then it shall be done tonight before we sail tomorrow." the one who Damon suspected was Edmund. "But first I have got a meeting with Antonio and Francisco. We have business to attend to." he added.

"Yes mi'lord." Matthew appeared confused, before referring back to the original conversation. "Primero mi'lord?" he asked as his Master shot him a look of disgust.

"Well it's not going to be about bunions is it?" the man who Damon suspected was Edmund sighed. "Of course we are having a game. I quite fancy getting my mothers necklace back. Father would've been really pissed if he'd found out I'd gambled it away, not that it matters any more." he said sarcastically, as if there were some other meaning behind this statement.

This was new information to Damon. None of Edmund's journals mentioned anything about gambling, although Damon knew that this must be Edmund as everything seemed to fit his story perfectly.

"What if you don't win it back?" Matthew asked. "Is it the usual?"

"We will get it back using any all means necessary." Edmund smiled. "If need be, your fists might come in handy tonight. It wouldn't do for me to fight such lowly merchants, but I'm confident you can knock out two old men very quickly. Of course I can help if they have weapons, but let's hope it doesn't come to that." he smiled in a way which Damon didn't like. Edmund was clearly not the person whom he'd read about. There was something about him Damon couldn't put his finger on, maybe it was an undeserved arrogance coming from someone who thought he was better than everyone else due to a fluke of his birth. However, regardless of whether he liked the man, Damon was going to have to act in a similar fashion to make himself believable as an early 16th century nobleman.

As a human, Damon's father was the Holy Roman Emperor, however Damon never knew him and was brought up at Brecon Castle, on the estate of the Duke of Buckingham. Due to who he was, Damon was offered privileges that wouldn't be afforded to other children of a mere groom. He saw and understood how the noblemen worked, however, the death of his mother meant his education in that department was cut short after the death of his mother when he was just 12 and he was sent to be educated in a monastery. He was an exceptional pupil and due to his wealth he was expected to go to either remain in the church or go to Oxford and could well have ended up in Henry's court. However Damon had a close affinity to horses, which was the one thing he learned from his stepfather who was a groom. As a result, he wanted to use his wealth to breed horses and live a less complicated life. He hated religion and he just wanted to settle down and have a family of his own, it was all he really craved, a real family considering his real family were a little unconventional. The Duke of Buckingham had been kind to him on the few occasions they crossed paths, but Damon was in no doubt of how shrewd a man Edward Stafford, the Duke of Buckingham really was, and as history was a good reminder, Edward's alleged plotting against Henry VIII led to his early demise and he was executed by Henry in May 1521 at the Tower of London. Edward had a good, if not potentially better claim than Henry to the English throne and Damon often wondered if his father had placed him in a position where he would have been prominent should Edward have took the throne.

Although Damon's meetings with the Duke were fleeting, he heard about everything and everyone who came into contact with him. His kindness towards Damon appeared to be a rare thing, probably due to who Damon was. With everyone else, the Duke was not so pleasant. It hadn't been until the moment he heard Edmund Spicer speak to Matthew, did he realise this was how Damon was supposed to behave. Damon had only ever become a Yeoman, albeit and extremely wealthy one and due to his upbringing as the son of a groom, he treat his staff with decency and respect, and after spending all of his time in MI666, he was used to treating people well. Now he was going to have to dig deep and allow a little bit of his vampire self emerge and become a much colder man. Right now that would be fairly easy as these people were strangers and he still was tasked with killing strangers as part of his job. However as he got to know these people, his real personality could emerge, the only way for him to prevent that was for him to kill for blood. He just hoped Esther and especially Bonnie (his constant judge and juror), would understand. For the time being he would follow Edmund for the day and observe.

Careful not to be noticed, Damon followed Edmund and Matthew around for the remainder of the day. He listened into their conversations, hoping to pick up some titbits of information which would be useful to him over the coming two years. Damon had made a conscious decision to question Edmund before he killed him on everything he could. There were some details about Edmund's childhood which Damon wanted clearing up, for instance his relationship with his older brother prior to the death of his sibling and his friendships. Any other information would have to come from compelling Matthew.

Over the course of the day, it became abundantly clear Edmund and Matthew were simply making last minute preparations for their journey. They bought food and at least two dozen bottles of wine. One person they saw handed them an envelope, to which made Damon curious as to its contents, however he knew he would need to be patient to find out what was written inside.

Later in the day when Edmund and Matthew headed back to the inn and opted to have something to eat. Not wanting to miss out on any conversation or the game of Primero, Damon followed them. He sat alone at a table in the corner, completely out of sight from Edmund and Matthew, while sipping beer and pretending to eat the disgusting food he'd just been served. There were times vampire hearing could be a pain, especially when accidentally hearing things you didn't want to hear, but now he was actively tuning in on Edmund and Matthew, as their conversation had just gotten interesting.

"The letter from Thomas was to forewarn me about what to expect when we get back." Edmund said. "Plans are afoot to allow me time to return to my fathers house and gather his affairs in order before we are invited to London. Thomas wants me to help deal with the red capped scumbag." he hissed.

Deducing Edmund was potentially talking about Cardinal Wolsey, Damon for the first time, agreed with Edmund.

"Will you be requiring the purchase of any medicines while we are still here?" Matthew asked. "I do know of..." he looked around to make sure nobody was listening before lowering his voice. "There is a man who can make a person well or ill with certain medicines."

Edmund frowned. "I'm sure there are many who can do the same in England." he said quietly. "But it may be a wise idea to purchase such goods here to ensure nobody can suggest we would have any hand in such untoward behaviour. Not that I condone it, but my friend Thomas has warned me there are certain ills in the world which need to be cured, and red hat is one of them."

"Would you like me to go purchase such medicine mi'lord?" Matthew asked.

Edmund nodded. "As long as you will be back in time for the Primero." he smiled.

"It isn't far and I'm sure he will be able to create something to cure red hat." Matthew smiled. "Any particular symptoms?" he asked.

"I want him to shit himself to death!" Edmund smiled evilly as he handed a small pouch to Matthew. "Don't be too long, Antonio and Francisco will be here within the hour." he added as Matthew stood up and nodded before leaving the inn, presumably to get whatever poisonous concoction required to kill Wolsey.

The death of Wolsey was known to have been caused by black diarrhoea, gastric cramps and a fever. He fell ill upon arrival at Sheffield Manor Lodge and records suggest he died of either dysentery or a ruptured ulcer. However despite it being common knowledge that Cardinal Wolsey was buried at Leicester Abbey, due to the exact location never being revealed, his body has never been recovered and thus poisoning could never be entirely ruled out. After hearing this conversation between Edmund and Matthew, it turned out the Earl may have had a hand in the death of the Cardinal. Perhaps this was what had helped him gain Henry's trust. Henry wanted Wolsey dead, but it would not look good if he had him executed, Wolsey dying before reaching London meant Henry got his way without getting his hands dirty. Whoever the writer of letter was, clearly was someone of high status. There were a number of senior nobles and courtiers with the name Thomas with whom Edmund communicated with during the course of his travels, the most likely person to want this deed done would be Thomas Boleyn, but would he even put his own name to a letter of such great importance? If the letter were to get into the wrong hands, there would be recriminations which would not reflect well on the future father-in-law to the King. Whichever way, Damon desperately wanted to read this letter as he was sure it must be in code, nobody would be that irresponsible to write such an incriminating letter, unless it was Henry who had ordered it in the first place.

Damon's interest in the letter was the reason he decided he would stay with Edmund instead of following Matthew. If he followed Matthew, he would find out what poison they were going to use, but by sticking with Edmund, he could make sure he wouldn't lose sight of the letter, and if someone did take it from him, Damon would spot it and steal it from them. Damon could easily question Matthew regarding the poison and if the manservant didn't know for certain, Damon could try sniffing or tasting it to see if he recognised any of its ingredients. He was familiar with the smell and taste of most poisons, it was one of the beauties of being a vampire, he could perform tests on dead bodies with just a sniff, meaning he would know the cause of death before any autopsy could be performed. Overdoses on normal modern medications were a little more difficult to sniff out, so he had simply stuck to the more obvious ones. Murder by forcing someone to take 100 paracetamol was practically unheard of. However with early 16th century medicine being so basic, he knew most poisons and should easily be able to work out what the cause would be.

Not long after Matthew left, two men entered the inn and sat down with Edmund. Damon guessed these men must be Antonio and Francisco. Edmund hadn't been lying when he said they were elderly, although by 21st century standards a man in his 50's (which is how old he suspected they were) wasn't seen as very old whereas in the 16th century, due to life expectancy these men would be deemed as practically ancient.

Whatever these men lacked in brawn, they must have made up for in brains as they were clearly well to do, albeit not on the same level as Edmund, or so they thought; at it turned out they underestimated the Earl's cunning plan. When the men spoke in Portuguese, Edmund acted as though he had no idea what they were talking about. Fortunately, Damon understood them perfectly and he new from Edmund's diaries that he did too.

Based upon the conversations of the day and how the game of Primero was progressing, Edmund had gambled a family piece, his late mother's necklace, and lost. As Damon had come to discover, this was a tactic of Edmund's, he would gamble the piece, lose, ask for a rematch and not only win, but win far more than he would have won before. Matthew was never around during the games, but if Edmund did lose, then Matthew ensured Edmund's opponents were relieved of their winnings by less gentlemanly methods. Of course, these only ever happened when Edmund was leaving the country, and nobody ever managed to discover who was the one behind the theft. Edmund was clearly a lowlife despite his position, and Matthew was more than just a manservant, he was a henchman. Damon was going to need to ask some serious questions later before he killed Edmund and the journey to England was going to be Damon learning from Matthew all about the real Edmund Spicer, not the nobleman in his journals. He especially wanted to know what happened to the loot he acquired from these merchants he gambled with.

Darkness had arrived and Edmund was still playing Primero with the men. They had been playing for over two hours and it was clear Edmund was losing a lot. Matthew was nowhere in sight, but Damon suspected he was close as Edmund had started acting strangely. Prior to revealing his cards, he would tap his foot on the floor. Damon had no idea what it was about, although it did appear to be a type of countdown, but he suspected he was messaging Matthew, who was clearly somewhere in the vicinity.

After Edmund tapped his foot only twice on the floor, Damon suspected there would only be one more game to be played. Edmund was losing and had gambled away a lot of money, and it was clear he was about to call it quits. Damon knew Edmund had been readying Matthew to ensure he could not be incriminated. Damon knew he was going to have to follow the men and potentially intervene in the fight if Matthew was overwhelmed as it was essential he won.

Exactly as planned, Edmund conceded after the next game and the two Portuguese men gathered up their winning with howls of joyous laughter. Damon decided it would be best to leave the inn before the men so he could silently follow them without arousing suspicion. Damon headed towards the alleyway he had escaped from earlier that morning, only to find Matthew standing there, waiting for the men.

"Mi'lord?" Matthew asked, a comment which surprised Damon, as it appeared he had already fooled the young henchman. Deciding to act dumb, Damon needed to play safe so he pretended to be drunk.

"Eh? Who are you?" Damon slurred as he turned to the wall, placing one hand against it as he decided that the only reason he to go down a dark alley would be to take a piss. However, he momentarily forgot that he wasn't wearing his normal clothes and began to fumble around with his codpiece, which luckily enhanced his drunken appearance.

"Sorry." Matthew apologised. "I thought you were someone else." he stared at Damon drunkenly fumbling away. "I hope you're not wanting me to do things..." he said, visibly shook.

"I'm trying to have a piss in peace!" Damon slurred. "Now fuck off before a break your nose." he argued, knowing that the two men had just left the inn.

This was the perfect timing for Matthew to leave and gave him a perfect excuse to follow the two men. "Sorry, didn't mean no offence." he apologised.

"None taken." Damon raised his hand as he finally managed to piss up against the wall.

Matthew left and Damon managed to quickly fix himself back up. He could easily track Matthew's scent and creep after him, but considering how much noise the two men who Matthew was following, it wasn't going to be a hard task. In fact, it was the noise the two men were making which was beginning to concern Damon, how on earth was Matthew going to get away with ridding them of their goods while they were being so loud in the street. The answer to Damon's question soon became clear as they got closer to the docks and the men made a beeline towards a ship. Matthew silently followed, with Damon not far behind. The men waited for a moment until a third man arrived, this one looking much younger than the men and significantly burlier than Matthew. They were clearly prepared for any potential skirmish. Nevertheless, Matthew approached the men to do his job. From the conversations Damon had overheard, Matthew had never been beaten and was clearly cocky regarding his prowess. However Damon wasn't sure whether he would be able to take on all three men, therefore he knew he needed to intervene and get rid of the third man and allow Matthew to work on the two elderly men. Damon swooped in and placed his hand around the younger man's mouth, preventing him from crying out. The other three men turned and looked at him agog.

"What is this man's name?" Damon asked the two men who had been playing Primero. When neither answered, Damon asked again, only this time he used his vampire powers of compelling them to get the answer he wanted.

"Pero." Antonio replied in a dazed voice.

"None of you saw me here and Pero was not here. He disappeared before you entered the inn and you never saw him again. You will not question his disappearance or report it to the authorities, do you understand?" he asked as all three men nodded. "You will forget you saw either of us." he turned to the old men. "Let this young man beat the shit out of you and take your winnings. You also gave him a bargueño." he added, picturing the chest in his mind and projecting the image into their minds. "Do not report this to the authorities here in Antwerp." he added as he swept the struggling Pero away at vamp speed. He found a small alleyway close by and dragged the man inside. Esther had only mentioned there being two men involved in the fight, which must have been reported when they returned home empty handed. Pero had been erased from any known records. To Damon this meant only one thing, Pero was not to survive the night. His vampire instincts began to take over, feeding from human blood straight from the vein was a wondrous experience, especially when the victim was young and healthy. Someone like Pero would taste delicious.

Damon stared into the eyes of Pero. "Don't scream." he compelled him quietly. "However, be very afraid, be terrified but don't run, stay where you are." he said.

The poor Pero reacted exactly as Damon wanted. Damon could smell his terror, even more so when Damon's face began to change. Pero's heart began to beat so rapidly, Damon became concerned his victim would have a heart-attack before Damon had the chance to tuck in. deciding not to waste another moment, Damon gave Pero one last look before turning him around and biting straight into the carotid artery in his neck.

The taste of Pero's blood was heavenly. Damon could feel his life force pulsing through his own veins, tingling and powerful. The magic inside of him was being set alive once more after decades of depriving himself of the sensation of drinking a person to death. Damon wanted to savour every moment, but he knew he couldn't, he needed to return to Matthew and make sure he and Edmund didn't get on the ship before he killed the Earl. Therefore Damon sucked Pero's blood harder, which turned his victim on. This was normal, as in the last throws of death from a vampire, the victim began to sexually enjoy the experience and become aroused. This was to let the vampire know that the victim was about to die. Only moments before death, the victim would have the most incredible orgasm before blacking out and fading into nothing. That was unless the vampire wanted to stop the death. During the moment of pleasure, the vampire would share in the sexual gratification, albeit slightly differently as it didn't actually affect the body in exactly the same way, however the vampire still experienced the sensation of an orgasm coursing through their veins. One of the reasons Damon preferred to drink from women was their ability to have a longer experience. An experienced vampire knew the exact moment when to feed blood to the human while allowing them the best orgasm of their life. This was the trick Isobel used to use on Damon when he was human, before she turned him, making him beg for her to suck him almost dry so he could taste her blood, almost as if it were a drug, therefore he personally knew how good it felt, which is why, in Damon's opinion, it was probably the best way to go. On this occasion, Damon wanted to kill Pero, therefore giving him blood to save him was not an option, so when Pero shuddered before going limp and the smell of his final pleasure hit Damon's nostrils, Damon continued to drink as Pero's heartbeat slowed and stopped, letting Damon know there was no more to be had. Damon let go and wiped his mouth, allowing his face to return to normal.

Damon checked outside the alley to see if anyone was around, but the coast was clear. He vampsped himself and Pero's lifeless body towards a small building near to one of the towers. Damon could easily fly over one of the towers, especially with his much stronger powers, but he wanted to ensure that once the body was in the water, it was never going to return to the surface. Damon's eyes scanned the room and he quickly found what he was looking for, a sack and a broken anchor. Damon managed to bend Pero's dead body into the sack and tied it up before fixing the anchor to the sack. Once ready, Damon checked to make sure nobody was around before jumping into the air and soaring through the skies out to sea. There he dropped Pero's body into the sea and returned, using the cathedral as his guide. The only time a vampire could fly was after consuming fresh blood of a healthy young human. This was one power which was rarely used because it was so draining that it could make them vulnerable to attack once they landed. However Damon knew he was about to make another kill, which was why he had no issue with using this little used superpower. Damon returned to view Matthew's progress a mere ten minutes after leaving him to sort out the older men, an instruction which Matthew had duly followed. Once done, Matthew collected his bounty and left to pass it on to his master, while Damon followed, feeling the delightful anticipation of his next kill.

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