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.

Thank you for your kind reviews after the last chapter. I've posted this one a little quicker than planned as almost all of the chapters leading up to the time-travel are written. As there is a little bit of a James Bond type feel to these initial chapters, they are quite in-depth as this information with be crucial to the rest of the story, so while these first 5 chapters might feel slow, they are important. They contain a lot of back story.

This story was never meant to be a fanfic, therefore some of the myth and lore does differ slightly from the TVD show and the characters may be a little different.

As a side note, I've been asked about Amazing Aisha, she is having problems with her account which appears to be infected with a virus, therefore she can't log on and is asking me to post her reviews on her behalf which I am copying and pasting. I am not blowing my own trumpet.

I hope you all enjoy this chapter, it will give a little more background.

Damon and Bonnie were sat in a corner of the Ox and Cart, the local pub in Courtney Vale. Damon nursed a pint of Guinness, while Bonnie stuck to a more modest orange juice as she couldn't consume alcohol like Damon. Fortunately, the pub was empty, apart from the landlord, who had been compelled by Damon to not hear any of Bonnie and Damon's conversation, but to watch out for Damon clicking his fingers to signal for another round of drinks.

Damon sighed. "Bonnie, be honest, did you know Esther was going to go this far?"

Bonnie shook her head. "I thought she was going to make you do all of the translations and then send you on some type of wild goose chase, diving into the Solent to search near the wreck of the Mary Rose on a treasure hunt." Damon looked at Bonnie quizzically. "Hugh Spicer was the brother of Elena and Katherine, he was on the Mary Rose when it sank." she explained.

"Oh." Damon nodded and shivered. "Travelling back 500 years is starting to sound like the better option." he sipped on his Guinness. "No toilets, no cars, people not having baths..." he shuddered. "How did I survive back then?"

"You'll manage." Bonnie smiled.

"My car." Damon complained.

"It will still be here when you get back." Bonnie reassured him.

"But my car." Damon sulked.

Bonnie laughed at that comment, because despite his vast wealth, Damon was the least materialistic person she had ever met, however, his car was his pride and joy and he clearly loved it. On the surface it looked exactly like a vintage Aston Martin DB5. Underneath, it had enough gadgets and speed to make Daniel Craig's James Bond jealous. He was a fan of James Bond, and even boasted Ian Flemming had based the characters womanizing ways on Damon himself. Thus, Damon liked to live up to the image he proclaimed he'd created. To keep the peace, Esther obliged him. As a result, Damon's already over-inflated ego had become even greater. However, despite her laughter, Bonnie knew that Damon wasn't happy about going on this mission. During the meeting, Esther had gone on to explain he would need to go back to 1530 and wouldn't be able to return until the Earl had killed himself at the end of 1532. That should leave Damon with enough time to get the pearl. The Heletian's couldn't infiltrate the mind of either child until the age of five, and as Lucy was only three months pregnant, this gave them plenty of time to prepare Damon for his trip and complete his mission. He would be back in Tudor England for just over two years, and the preparations were already underway, which would take just over a month, leaving time to finish transcribing the grimoires and to slowly strip the magic from the children. That was as far as Esther had explained in the meeting as there were a lot of technical issues she needed to get prepared before she could give any further information, leaving Bonnie to take Damon to the pub to drown his sorrows. To try and console him, Bonnie opted for a different take on the situation.

"Thank you." she said softly.

Damon frowned. "For what?" he asked.

"For saving my family." Bonnie offered a small smile of gratitude. "Lucy won't be allowed to have any more children now it is known she can mother witchbinder twins. She's the only family I've got left, and if I decide to go down the route of becoming a time witch..." she started as Damon looked at her with shock.

"Are you actually considering it?" he asked.

"I'm only 27, I've got 3 years to decide whether to give up my chance of being a mother and becoming a time witch, or or risk it and hope to find Mr Right." she shrugged. "The chances of me meeting that right person before I get to make that choice is shrinking. Being a time witch would allow me to do some good for longer. Anyway, it's cheaper than Botox." she smirked, as Damon smiled back. "That's better. I want to see a smile on your face. I get worried you might do something stupid when you start moping around."

Damon sighed. "I know, it's just that I'm going to be missing my friends for two years." he complained.

"Well, from what I've read about Edmund Spicer, the Earl of Hallamshire, I reckon you're going to make a lot of new ones." Bonnie stated. "And it sounds like you will have quite a lot of fun along the way." she smirked. Damon frowned at her comment, so she continued. "It sounds like he was rather popular with the ladies at court. Despite Henry being besotted with Anne, Edmund would secretly help the accommodate the King's needs while Anne refused."

"I guess he was unpopular with the Boleyn's then." Damon sighed.

"On the contrary. He would find the greatest beauties and secretly present them to the King, testing his love for Anne. No woman lasted more than one night with Henry, he didn't want them. He believed it was Edmund who proved his love for Anne was divine and that no woman could ever compete with her. Edmund had to ensure their suitability for the King." she explained. "The Boleyn's were happy with his methods."

Damon raised a suspicious eyebrow. "How?"

"These weren't the normal ladies of court. Henry couldn't have a scandal. These were the daughters of Yeomen, Baron's, Knights or minor Lords. He would search England for the girls and the fathers would be paid handsomely for their daughters services. As you know, women of higher birth still meant little back then, they were basically brood mares. A lower ranking Lord having his daughter associated with the King could pay dividends when it came to elevating themselves. The men were often given higher ranking positions or were financially compensated beyond what they could ever imagine to earn in a lifetime. Edmund had to make sure they were capable of satisfying Henry, if you know what I mean."

"Edmund road tested them?" Damon looked at her shocked.

"I believe he did." Bonnie nodded. "It was during his travels when he met the Spicer family, which eventually led him to marrying Elena."

"She must have been something special for Edmund to hang up his codpiece." Damon joked.

"You've got to marry her and stay married to her for 11 months. All you need to do is pretend to love her, that would still fulfil what is written in history." Bonnie reminded him, checking the time on her phone. "We need to get back to the office. You've got that report to hand in and we need to start transcribing some grimoires."

The next day, Damon had the report on his desk, waiting to hand in to Esther. Overnight, after much alcohol and a few litre's of blood and complaining to Bonnie over the phone, he'd come to terms with his fate over the next two years. Nobody had gone into any fine detail regarding how Damon was to become Edmund Spicer, or even how time magic worked. However Bonnie's chat about Edmund's role at court had soothed Damon a little. Vampires had a very high sex drive, and part of what he'd dreaded was the thought of being celibate until he married Elena. Without sex, his appetite for blood would have increased, making him more dangerous and likely to make mistakes. He just hoped he liked Elena enough to stay faithful to her for 11 months, a feat he'd never managed since he was human and his wife had died. Other than his sire Isobel, Damon had never committed to spending more than a month with a woman, to Damon, 11 months seemed like an eternity. It was at this point Damon realised an extremely important point. Vampires couldn't procreate, if that was the case, how on earth was he going to get Elena pregnant?

Something else was playing on his mind. He was going to basically be Henry VIII's pimp. A hundred years ago he would've jumped at the prospect but times had changed. He was no longer the vampire he used to be. He had a greater respect for women, despite him being constantly on the prowl for a new challenge. Whenever he met someone he thought would be suitable, he made it very clear that what would take place would simply be sex and no strings attached, it wasn't his fault they never listened. Now the notion of procuring and testing out women for a King wasn't his idea of fun. Not that he would have any problems in that department, vampires were always ready for sex, no matter how unattractive the other party was. Any issues and a drop of blood would do the trick. To Damon, this was different, it made him feel sick to his bones that he would be using women this way. He just needed to reconcile in his head that he would be doing this for the greater good, the old saying of 'lie back and think of England' was certainly apt in this case.

Damon tapped his fingers on his desk, Bonnie had been in a meeting with Esther for over an hour. She'd told him the previous night that she needed to talk to Esther, but refused to go into finer details. Thus Damon was still waiting to hand in his report and getting more and more agitated by the minute. He knew he needed to check his emails, but he couldn't concentrate. Conversations were happening about his future behind his back, including his best friend, and he was feeling frustrated.

Damon's office phone buzzed, Esther's name flashed on the screen to inform him which office it was coming from. Part of him didn't want to pick it up, just in case he said something he might regret, but he decided pettiness wasn't going to help his cause, so he picked up the phone and took a deep breath before announcing himself.

"You rang m'lady." he responded in a sarcastic tone.

"My office Salvatore, now! And don't forget that report." came Esther's curt reply before she hung up. Damon loved Esther as a friend, and he hated it when she was pissed off with him. He knew he deserved her snappy response, but right now he wasn't in the mood for niceties. He snatched up the report and stormed out of the room and up to Esther's fancy office. "Come in!" Esther called out before Damon even had chance to knock. He walked in and put the report on Esther's desk, noting Bonnie was nowhere to be seen.

"Where's Bonnie?" Damon asked.

"The containment lab." Esther told him. The containment lab was where witches would perform spells on themselves, either as a test or for something Esther wanted. Any spells performed in the containment lab had to be signed off by Esther herself. "Good my report." she smiled as she put it in her in-tray ready to be read.

"Anything else?" Damon asked, turning to the door.

"Sit down." Esther sighed, clearly aware she was going to have to tread carefully. It was clear Damon wasn't happy with what his future held, so she knew she was going to have to placate him. Esther waited until Damon did as he was told before she started. "Bonnie is going to become a time-witch." she told him, deciding not to beat about the bush.

"What?!" Damon looked at Esther in shock. She'd told him the previous day she'd been considering it, but he didn't realise she was serious. "Why?" he asked.

"Lucy is pregnant with twins, once a witch has one set, all future pregnancies will also be twins. As she is carrying witchbinder babies, the same applies for those too. She will only ever carry witchbinder twins. If we don't help Lucy, then she will never be able to get pregnant again, the risk is too great. Bonnie is ambitious and eventually wants to take on my role. To do that she needs to become a time-witch. She has no desire to have children of her own, and she hasn't met anyone she wants to raise a family with. Therefore she has decided to perform the matriarch spell. When she is finished, she will start her basic time-witch training." Esther explained.

"How does she do that?" Damon frowned.

"Your little trip to 1530 will help her. She will be in charge of sending back items you need while you are there." she smiled.

"How will she know?" Damon frowned.

"Do you really think we would let you go back and just leave you to get on with things without our help?" Esther laughed. "We'll be holding your hand while you are there. You will be able to have constant communication with the office." she smiled.

"How?" Damon looked shocked.

"Stefan and Valerie have been working with Porton Down at developing adaptive technology and medicines. You will have every modern convenience at your fingertips to help you find the pearl. I will expect regular updates."

"So I just call you? I hate to be the one to break it to you, but iPhones didn't exist back then. Neither did Wi-Fi, Bluetooth or the internet. I'm not entirely sure how we can keep in touch." Damon frowned.

"Magic and technology combined is all you need to know right now." Esther assured him. "We will make sure all information you need is on hand. The archives have a rundown of all known movements of the Earl, allowing us to give you instructions on your next moves. You will need a daily dose of vervain..."

"Wait a minute. Why do I need to take vervain?" Damon asked.

"Weakening your powers will make it easier for me to send you back and keep you there. You are an old and strong vampire Damon, my magic will need to keep you there for over two years, it is going to be hard for me too. Plus you need to appear more human. Being slightly weaker will help. It's not as if you won't have any of your powers, you'll me more like a 300 year old with the healing ability of a new vampire. If you get injured, you need to heal more slowly, you need to be able to appear ill if you are surrounded by the sweating sickness. You will die in 1532 and you will most certainly need vervain for that transition to ensure your contemporaries believe you are truly dead. Also it is part of the mixture to allow you to father a child." Esther explained.

Damon looked at Esther horrified. He knew Elena had died in childbirth, and he knew he was to pretend to be in love with her, but he'd also wondered who the real father of the child was going to be. It had occurred to him it might have been Henry himself, but this revelation disturbed him. There were a number of secrets he kept to himself from those around him, especially about his time as a human. He'd never gone into great detail about the circumstances surrounding his own transition into a vampire. Esther knew he'd been turned by a woman called Isabel Ross who had trapped him when he was at a low point in his life. He'd also made it clear to Esther that Isabel died soon after she'd turned him as a witch called Maggie recognised her and killed her because Isabel had killed the witch's mother, who it in all likelihood was Hilda Frampton. What Damon had never mentioned was that his own wife had died during childbirth, which was what had led to his melancholy and allowed him to get mixed up with Isabel. The notion that he would get another woman pregnant who was going to face the same fate as his wife Sarah and their child who was born dead.

"I'm not sure I can go through with that." Damon said grimly.

"Elena and the baby are already dead." Esther told him kindly. "They have been for almost 500 years. Just think of the lives you will save."

"I've already been through this once..." Damon started.

"But the difference is that you loved your wife." Esther explained. "Just consider this as another mission. For goodness sake Damon, you are a vampire who has no qualms killing people. When did you suddenly gain a conscience?" she frowned. "Of all the people to be fine with doing this, you would be top of my list. I can't exactly ask Stefan, other than him already being connected, he would find something nice to say about even the most unsavoury characters throughout history. He's no good for missions like this." she stopped for a moment, noticing that her comments weren't helping. "Look, if you want, I can create a detachment spell, something to prevent you from getting too emotionally involved." she offered, to which Damon looked at her sceptically.

"Can you do that?" he asked.

"There is a spell which will allow a vampire to feel detached from almost anyone they meet." Esther nodded.

"Almost?" Damon raised an eyebrow.

"There is no spell to prevent the connection." Esther warned. "But it should work for everyone else."

The connection was pre-destined union between a vampire and a human, who would ultimately also become a vampire. Once the human had transitioned into a vampire, they would remain together as a couple for all eternity, never to be with anyone else again. One of reasons Damon was so in demand as a spy, was because he wasn't connected to another vampire, which allowed for him to be able to do anything necessary for his job, which sometimes included what was known as under the sheets work. Damon wasn't the only single vampire who was expected to go this far for the team. The other non-connected vampires were the brothers Klaus and Elijah; and their sister Rebekah. Sending vampires on these missions was always preferable as they tended to feel more detached from their subjects than witches. Vampires were in general more emotional than humans and witches, but unless they were connected, they would never fall in love romantically, although they did sometimes care about the people they bedded.

"It's not Elena that I'm concerned about." Damon explained. "It is how I would feel about the chance of not being a father. Seeing Elena and the child die at the same time would bring back memories."

"The little boy Henry, he died two days after Elena. So it might not feel exactly the same. But it will give you chance to have a son, even if it is only for a small amount of time. Maybe you can say goodbye to the child you and Sarah had during those two days." Esther suggested. "It might prove cathartic."

Damon thought for a moment. He had been in Oxford on business when a messenger arrived to tell him Sarah had fallen ill with the sweating sickness with only a few weeks to go before she was to give birth. By the time he returned to his home in Devon, Sarah was already dead, along with their son. He never had chance to say goodbye to them. Despite his misgivings, he knew there was a chance Esther might be right, this would also give him a chance to go visit their graves before the church where they were buried was destroyed by fire in 1532. maybe he could have their bodies moved to another church which would survive until present day. Damon made a mental note to look into churches which had been around for over 500 years.

"You don't need to do the spell." Damon shrugged. "You're right, it will probably help me come to terms with what happened as a human."

"Maybe that is the reason you are not connected." Esther raised an eyebrow. "To connect, the heart must be free of all burdens of love."

"Who said that?" Damon frowned. "It certainly isn't a biblical quote."

"Maybe the bible you know isn't the only book of significance from that period." Esther smirked. "Anyway, I digress, let us get back to business. You cannot look up what you are to do. As soon as we found the picture and worked out you were to travel in time at some point, we removed all traces of Edmund Spicer from our history books. Anything you know is from all prior knowledge, which won't cause too many issues. We couldn't have you know too much about your own future as it may alter your decisions and affect the present."

"That's deep." Damon frowned. "Look as long as I don't have to work as Groom of the Stool, I'm fine. The thought of wiping Henry's arse puts me off my whisky."

"Don't worry. There is no record of you having to perform those duties." Esther assured him."

"Phew." Damon smiled for the first time. "That is a really shitty job."

Esther raised an eyebrow at Damon's terrible joke. "It was also the most coveted role in court. The Groom of the Stool had the King's ear."

"And the King would have their head if they didn't listen properly." Damon nodded. "Bonnie told me I was going to be finding suitable ladies for Henry to bed while Anne held out on him, and that I might be expected to inspect their worthiness for Henry." he said, happy he had acknowledged what he would need to do with the politeness that Esther deserved.

"Ah yes." Esther nodded. "I suppose there are a few things which will be useful for you to know before you go on your mission without creating too many issues."

"Like?" Damon asked.

"Hugh Spicer, Edmund's father, was good friends with Thomas Boleyn and so was Edmund."

"But wouldn't Thomas not want Edmund to bring women for Henry to meet his needs?" Damon frowned.

Esther shrugged. "From what we can gather, Thomas Boleyn was very supportive of the measure. As was every member of Henry's court who hated the Boleyn's. I suspect Thomas wanted to prove that Anne was Henry's true love, and when the other women failed to match up to Anne, his point was repeatedly proven. The other factions at court wanted Henry to find someone more suitable to get rid of the Boleyn's and stop him from his break with the Catholic church. So Edmund had a pivotal role at court for all sides. For Henry, it helped him decide upon Anne's suitability, although it was not something which could be used as a favourable argument to be submitted to the Pope when he attempted to annul his marriage to Catherine of Aragon."

"And what about Edmund having to ensure their suitability." Damon frowned.

"That is just gossip." Esther smiled. "We have no real proof. I cannot believe Henry would want a woman who was already tried and tested, however you ought to prepare yourself for the possibility. I'm sure you won't have too much of an issue with that. Just remember, when you get home, they will all have been dead for 500 years."

"What research do I need to do?" Damon asked, deciding to try and seem as detached as possible. He was itching for blood as he was wound up. The sooner the meeting was over, the better.

"The Earl of Hallamshire died on 15th July 1530. At the time Edmund was in Antwerp after travelling through Europe. When he heard of his father's death he returned back to England at the beginning of September and returned to his home in Derbyshire. Not long afterwards he was requested by George Talbot, the Earl of Shrewsbury, to meet him at Sheffield Park. Cardinal Wolsey had been arrested and was being escorted from York to the Tower of London and would be stopping off at Sheffield Park for a few nights. As you probably already know, while in Sheffield Cardinal Wolsey took ill. He left Sheffield and after reaching Leicester a few days later , he died from the illness. Edmund was part of Wolsey's escort from Sheffield to Leicester. After Wolsey died, Edmund was summoned to court. That is all I can tell you for now. The rest is the past, soon to be your present and eventually your future." Esther smiled. "You can research the final days of Cardinal Wolsey if you wish to know more about what ailed him."

"So where and when do I land in 1530?" Damon asked.

"Edmund set sail from Antwerp to Hull on the Temptress on 4th September 1530. you will be sent back to the day before to find him. There are records he got into a fight in a tavern the night before he sailed. That is where you will find him. He only had one servant with him. You will need to kill Edmund and compel his servant to make him believe you are Edmund. Before you kill Edmund, you need to read his memories. The history books will only give us a snapshot into his life. Take his memories, kill him and compel his servant. You will then be able to become Edmund quite easily. I'm sure you didn't need me to suggest those methods." Esther grinned.

"As long as I know where to find him." Damon nodded. "I'll kill him and feed him to the fish to finish him off. They'll never find him." he smiled.

Esther glanced up at the clock on the wall near the door. "I suggest you leave and get researching the early life of Edmund Spicer. In a few days time, we will go through what you will be taking with you."

"Taking with me?" Damon raised an eyebrow, slightly excited by the fact he might have some technology with him.

"We will need to send you with a portable time portal. That is all you need to know for now." she smiled standing up and pointing towards the door. Realising this was his cue to leave, Damon simply smiled, got up and walked over to the door.

"Thank you Esther." Damon said kindly.

"What for?" she asked.

"Giving me the chance to say goodbye." Damon said sadly. "I'll make sure I don't fail you."

"Given the fact that the pearl is missing, I would hazard a guess that you will succeed." Esther laughed. "Now go." she insisted. "I have important matters to attend to."

"Bonnie?" Damon asked.

"Yes Bonnie. Right now, she is my number one priority. And please be sensitive around her for the next few days, she's given up a lot. I should know, I made the same decision myself when I was her age." Esther looked at him with a sad smile.

"Yes ma'am." Damon blew Esther a kiss before walking out of the door.

"Oh and Damon..." Esther called out before he closed the door. "You'll need to grow a beard." a comment which stopped Damon in his tracks momentarily. He hated having a beard, they itched and from his experience, he deemed them ugly. However he knew he was going to need to blend in, so with a heavy heart, he headed towards the library to learn everything he could about the early life of Edmund Spicer

in case anyone is interested, Courtney Vale is based on the village of Iwerne Courtney in Dorset and the school is based upon an old school which is currently up for sale called Shapwick School near Bridgewater in Somerset.

Thank you all for your kind reviews. They are always appreciated.

If you like this story, please like, follow and/or review. It helps motivate me to get the chapters written and published quicker.

Mandzipop.