Disclaimer: I don't own Fate Stay Night or High School DxD. They belong to Kinoko Nasu and Ichiei Ishibumi respectively. If I did, I would have already created an Ilya route in the VN with a fully grown and matured Ilya as the heroine and make a badass protagonist for High School DxD instead of a pervert like Issei.

A/N: This is my first fanfic that I've been itching to write ever since I read Thousand Mastery's Kaleid Liner DxD. Please give some constructive criticisms that can improve my writing. Credit goes to fsnfan for helping me fleshing out the details for this prologue and Anthonyl6892 for becoming my beta. Now without further ado. Story start.

Update: 12th April 2014

- Changed some of my theory on Archer's reincarnation and the conditions and side effects.

- Added some more details. Nothing major.

- Ryuudouji Temple atop of Mount Enzo, End of the 5th Grail War -

Six figures stood at the temple grounds facing a certain spot where a collection of high amount of concentrated prana was congregating.

"So, this is it? This is the Holy Grail?" Shirou asked.

"More accurately, this is the Lesser Grail that's supposed to be used by us to grant our wish." Rin answered her husband.

"You mean your and Archer's wish Onee-san. Merlin and I have already forfeited our rights for the Grail remember? Furthermore, Ilya has already lost her Servant and Shirou wasn't a participant in the first place." Sakura said to her sister.

"I'm just glad that the Einzberns were able to figure out a way to create a vessel for the Lesser Grail using a lifeless object instead of using me or one of the other Homunculus. I don't even want to think what would have happened to me if that were the case. I guess I'll have you to thank for that Merlin. The notes on the theory of creating a Lesser Grail from a lifeless object that you left behind after the 4th Grail War was what saved me it seems." A fully grown and matured Ilya said.

"Think nothing of it child. I do not even remember what I did during the last war. After all, both the current me and the one in the previous war were only copies of the real me in the Throne." Merlin answered Ilya like a kind grandfather speaking to his granddaughter.

"Regardless, Rin and I are the victors of this Grail War. Well, it's not like I have a wish of my own that the Grail can grant." Archer or Counter Guardian EMIYA said with a sad smile. After everything that he had experienced and seen in this war, he had already accepted his hellish fate, albeit bitterly.

Everyone except Merlin watched Archer with bitter and sad expressions. This world's Shirou was able to obtain happiness after graduating high school and marrying both Rin and Sakura but this man who is an alternate future version of Shirou would never obtain such happiness. He had sealed his fate when he decided to make a contract with Alaya. Even the power of the Grail as a wishing device couldn't release him from his eternal torment.

It was Rin who discovered Archer's identity when she witnessed his life during the Dream Cycle. Before that, Archer had feigned ignorance of his identity using an excuse such as being a Heroic Spirit from the future that caused an abnormality in the summoning and gave him amnesia. At the time, Rin was suspicious of Archer's claims but she was able to restrain herself from using a Command Seal to force Archer to reveal his identity.

When Archer's lie was exposed and his identity was revealed, he was forced to explain his motives to everyone and why he sought it. His description of the hell he had to go through as a Counter Guardian caused almost everyone from the Tohsaka, Emiya and Matou families and their Servants to put their heads together to find a way to save him from his eternal torment. Unfortunately, no solution was found and everyone was forced to accept that Archer's salvation will be forever out of reach.

Merlin however, had other ideas.

"Don't be so quick to give up boy. I might have a solution for your predicament."

Everyone including Archer looked at Merlin with shocked and surprised faces.

"What? You were the one who said that it wasn't possible for me to annul my contract with Alaya even with the Grail." Archer said in a tone that's bordering on being accusatory.

"Yes, that's right. There is no way for anyone to release EMIYA in the Throne from Alaya's grasp. But my solution isn't for him but you." Merlin says patiently while pointing at Archer.

"Explain." Rin said with a frown.

"During the course of the war, I was able to devise a thaumaturgical theory to reincarnate Archer and give him a second chance at life using the Grail. It's not enough to release the actual EMIYA who's in the Throne, but it's enough for me to make the current Archer forever out of Alaya's grasp as long as he is not stupid enough to make another contract with Alaya."

Everyone fell silent after hearing Merlin's explanation. Archer in particular was processing Merlin's words and was contemplating on his options. Archer has long since learned that for everything that is too good to be true, there will always be a catch. They say it's always good to keep an open mind but Archer prefers to be skeptical of any contract that he might enter so that he knows everything of what it entails. A lesson he learned too late after entering a contract with Alaya.

"What are the conditions for the reincarnation to annul Alaya's contract?" Archer asked Merlin trying to be as open minded as possible while at the same time being skeptical of the chance being presented in front of him. Merlin has proven himself to Archer to be trustworthy despite his minor pranking habits during the course of the war, so if Merlin claims to have a way to save him, albeit not completely, Archer will at least listen to his proposal before deciding.

"In order to break your current contract with Alaya, I will be taking advantage of Alaya's currently weakened grasp on you to send your soul to an alternate dimension where Alaya's influence is weaker to the point of almost non-existent. Also, to further weaken Alaya's hold on you; I'm going to make it so your reincarnation will be the same as any other, meaning that you would be wiped clean of all your memories."

"At least, for 16 to 17 years that is. The 16 to 17 years of transition is for the Gaia in that world to recognize your existence as a natural occurrence so that you won't end up being erased. Your current memories will gradually return after that." Merlin continued before anyone could protest.

"However, to fully break the hold Alaya has on you, you will have to work hard and become a proper Heroic Spirit. It's the only way for you to completely annul your contract. Sadly, even if you do become one, it is you who will be freed and not the EMIYA who's currently in the Throne, as the legend that you will inspire is tied to you instead of him as the two of you will by then be considered to be separate entities." Merlin says in a tone that is a mixture confidence and sadness. It looks like he has absolute faith in his theory, but at the same time not being able to do more saddens him.

"Wait. That would require knowledge on the Second Magic. How do you know the workings of the Kaleidoscope?" Rin asked Merlin in a suspicious tone. Currently, she was one of three existing practitioners of the Kaleidoscope. The other two being her mentor Kischur Zelretch Schweinorg and her rival Luviagelita Edelfelt.

"My dear child, it was easy for me who was summoned in the Caster class to get through your Bounded Fields without activating any of them. I advise that you use mundane methods in conjunction with the Bounded Fields next time by the way. Also, with my advanced knowledge on Magecraft, deciphering your notes and reverse engineering them posed no challenge at all. I now know enough to effectively utilize the Second Magic without any problems." Merlin says this in a smug tone.

Rin was both furious and horrified. She had kept her notes on the Second Magic under heavy guards with layer upon layer of Bounded Fields. Now, her sister's Servant had just confessed that her efforts were for nothing. Before Rin could voice out her complaints, she was cut off by Merlin who continued his speech.

"Thanks to that, I have prepared some notes on some theories and calculations that I am sure would be able to assist you in furthering your studies of it." Saying this, Merlin pulled out some papers from his robes and showed it to Rin.

Rin only stared dumbfounded at the papers for a few moments before she forcefully snatched them from Merlin's hands while making sure that the papers weren't damaged from her actions and immediately started to peruse them. Satisfied, she folded the papers and put them inside the coat she was currently wearing. She still glared at Caster however.

"Now, where were we?" Merlin asked while being amused by Rin's actions.

"You were explaining the side effects of reincarnating my soul in an alternate dimension." Archer decides to just move the conversation along before more distractions occur to derail them from their current topic.

"Ah... Yes... Well, actually, this part of my solution is a bit of a gamble I'm afraid." Merlin said in a worried tone that completely contrasts his earlier behaviour.

"What do you mean Merlin?" Sakura asked worriedly seeing her Servant becoming worried for the first time ever since she had summoned him.

"What I mean is that I will have no idea on what kind of life that Archer's reincarnated self might have during the transition. Basically, whether the reincarnated Archer will grow up to be someone who has a desire to do either evil or good during the transition is out of my control. Fortunately, when Archer's current memories start to return, he should be able to take over without any problems."

"Also, as a precaution, I've made it so that all of Archer's memories will return at once if his reincarnated self finds himself in a deadly situation that he could not survive normally. However, if this were to happen during the transition phase, then there is a good chance that the world's Gaia would try to erase him, as Gaia will recognize him as something that should not exist. If such a situation occurs, he will have to make a contract with a Master to supply him with prana in order to exist. Unfortunately, if that happens then he will never succeed in becoming a proper Heroic Spirit and will sooner or later return to the Throne as part of EMIYA again." Merlin answered Sakura's query.

"So whether or not my soul would reincarnate as someone who will grow up to be good or evil is unknown, huh? Not only that, if I'm in a deadly situation where I might die without my abilities before the 16 to 17 years transition phase is up, I'll get my memories back to save myself… but end up dooming myself in the end anyway."

"And by the looks of things you won't even be able to tell me what gender I'll be reincarnated into. That's just great." Archer sarcastically commented. He knew that things were never that easy and it looks like he was right yet again. He's starting to think that the world itself hates him.

"Not to worry. One of the requirements for your soul to reincarnate without problems is that it has to be a male. So you don't have to worry about suddenly becoming a lady." Merlin said.

Phew.

I stand corrected; maybe the world doesn't hate me that much after all. Still, it's too early to relax.

"Are there any other side effects? What about my Magecraft?" This will probably be one of the most important factors that he has to take into account when making his decision.

"Naturally, I've already taken your Magecraft into account as well. I'll be able to transfer all your developed Magic Circuits but I have no idea how the rules for Magecraft would behave in that world so you'll have to find that out for yourself. If you're lucky, the rules won't be that different but if not...well, you're going to have to figure out what to do about it on your own."

"Still, just in case, I'm going to make it so that your reincarnated self will start to instinctively be able to grasp how to use your Magic Circuits once you're 5 years old to reduce the chances of you being in a situation that makes all your memories return, although I don't know how much use it will have since we don't know if the rules in that world will allow you to use your Magecraft or not. The only thing I can tell you is that Gaia's influence in that world will also be weaker though perhaps not as weak as Alaya's." Merlin says this to Archer in a tone not unlike a grandfather giving advice to his grandson.

In short, while there won't be any problems with recalling his memories after the 16 to 17 years are up, his Magecraft that he has honed all his life would either be lost to him, even if he still retains all his Magic Circuits, or become stronger as Gaia's influence will be weaker. The two possibilities have no way of being confirmed in advance, so it really will be a gamble whether he will still retain his Magecraft or not. Still, compared to the alternative of him continuing on as a Counter Guardian, Merlin's proposal was much more preferable. At the very least, Merlin's plan will give him a definite chance to realize his wish instead of his grasping at straws at the chance of being summoned in the Holy Grail War of his original world and causing a paradox by killing his actual younger self.

While Archer tries to make up his mind whether to accept Merlin's plan or not, his mind starts to recall the events of the war and everything that he had learned during the war after his summoning.

Everything had at first started around two weeks ago when he, Counter Guardian EMIYA, was summoned by Tohsaka Rin for the 5th Grail War.

For the sake of freeing himself from Alaya's grasp, Archer had bet everything on causing a paradox to eliminate himself from all the worlds. Unfortunately, as soon as he was summoned in the 5th Grail War, he was already aware that this was most likely not the world that he sought for in order to realize his wish.

The first thing that clued him in was that it was 10 years later than the actual date of the 5th Grail War that he was embroiled in during his life. The second clue was not that he was properly summoned by Rin. After all, he was not exactly aware of his own world's Rin's circumstances when she summoned her Servant since they never bothered to discuss about it. No, what clued him in was the other individual present during his summoning as the Servant of the Bow.

Emiya Shirou. The person Archer has to kill to cause the paradox.

Or more accurately, this world's version of Archer's target. It was fortunate that Archer's years of mental discipline allowed him to mask his hostility to this version of his younger self that very instant, lest he reveal his true intentions. Even if he was aware that this version of Shirou was not the one that he sought, Archer would still kill him if this Shirou also desired to walk the same path he did.

Turns out however, he needn't have bothered.

Despite this version of Shirou's desire to become a hero of justice, the battlefield that he had chosen was not the bloody conflicts and wars that Archer had chosen in his life but instead Shirou had chosen the courtroom as his battlefield.

This world's version of Shirou had decided to become a prosecutor to realize his own version of the dream of becoming a hero of justice. He had married both Rin and Sakura five years after their high school graduation and was blessed with three children, two of which were female twins who Rin gave birth to. Both Rin and Sakura also had decided to keep their Magus family names.

Archer was surprised that Rin and Sakura were able to share Shirou, but he decided that it was none of his business.

As long as this Shirou is not a suicidal idiot who travels from one conflict to another to uphold his ideal of saving people, Archer was content to let him live even if he still didn't like Shirou. The fact that Shirou had already created a family for himself just made it easier for Archer to make that decision.

Since his initial objective was already out of his reach, Archer had at first decided to just deal with the malevolent deity, Angra Mainyu, in the Greater Grail and end the war earlier for the sake of sparing the lives of the innocent from becoming victims of the war.

However, Archer's expectations were again derailed as he discovered that the Greater Grail in this world was never tainted by Servant Avenger in the 3rd Grail War. Thus, it was safe to say that the current Grail may be completed safely without worrying about its contents spilling out into the world and killing billions of people. As long as the rest of the other 6 Servants were defeated, the victor will be granted the chance to realize their wishes.

Curious of what happened during the 4th Grail War, Archer had advised Rin to learn as much as she could about the previous war. From what Archer knew, it was only because the Grail was tainted that Anti-Heroes could be summoned by the Grail. How could a Caster that was a proper Heroic Spirit bring such changes to the events he once knew so well?

He was somehow able to convince Rin by telling her that knowledge of previous Grail Wars may be crucial to their victory.

After some investigation, they were able to find out the full events of the 4th Grail War which was supplied by Emiya Kiritsugu. He was somehow still alive and living in Fuyuki with both Irisviel and Ilyasviel. Just as he had surmised, Archer had found out that the events of this world's 4th Grail War really was different than the one he knew. This was mainly due to the identity of the 4th Grail War's Caster which was, ironically, the same Caster that was summoned for the 5th Grail War.

Merlin.

Merlin's summoning had changed much of the 4th Grail War's events. Immediately after his summoning, Merlin killed his Master as his Master was a serial killer. After that, he allied with Kiritsugu as the Saber that Kiritsugu had summoned was still Arturia Pendragon, the King of Knights.

Merlin was able to dispel Lancelot's Mad Enhancement with a meticulously prepared trap when Lancelot revealed himself. This event allowed Lancelot to reconcile with Arturia. Thanks to Merlin's advanced knowledge in Magecraft, the following negotiations with Kariya also went well as the deal only entailed saving Sakura from Zouken which Merlin was able to do almost effortlessly by killing Zouken and destroying all his familiars including those inside Sakura. Merlin had also restored Kariya's body as a token of goodwill.

Tokiomi was still killed by Kirei's betrayal, but Kariya was not framed for it as he would have been had Merlin not convinced Kariya to give up on his grudge on Tokiomi for Sakura's sake. Thanks to this, Aoi relied more on Kariya after the 4th Grail War for moral support and they ended up marrying a few years later. Rin still retained the Tohsaka family name in order to carry on the family's Magecraft but she and Sakura grew up as inseparable sisters. Perhaps that was what allowed them to share Shirou.

As for Gilgamesh, Merlin's advice to Kiritsugu to return Avalon to Arturia was what allowed her to triumph against the arrogant King of Heroes despite him pulling out Ea when he was cornered by the three Servants. Unfortunately, Lancelot and Merlin did not survive Ea's attack as Avalon was only able to protect Arturia. Kirei was then beheaded by Arturia once the Servant he took from Tokiomi was defeated.

As winners of the 4th Grail War, Arturia and Kiritsugu gained the rights to wish upon the Grail but they discovered that Kiritsugu's wish could never be granted even with the Grail's powers. As Kiritsugu fell into despair, Arturia, who by then had already abandoned the notion to wish for a different king to rule in her place thanks to Lancelot's and Merlin's persuasions, wished for the return of Irisviel in order to alleviate Kiritsugu's despair by returning the very woman he had loved.

Arturia's plan worked quite well as Irisviel's return brought hope back to Kiritsugu. Afterwards, as the 4th Grail War finally came to an end, Arturia disappeared. It's most likely that she went to Avalon to finally rest and be freed from her burdens.

As Kiritsugu had realized the Einzbern's lifelong wish to obtain the Grail, Ilya was returned to him and they started living in Fuyuki as a normal family. As a reward for Kiritsugu's success, Jubstacheit also reconfigured Ilya using the notes Merlin left behind on the more advanced knowledge of Coining a Homunculus to give her a lifespan of a normal human and all the perks of being one.

In other words, Ilya's body may continue to mature instead of staying in a body of a 10 year old. Jubstacheit was also able to give her a fully functioning reproduction organ with a libido to match so Ilya won't have any problem if she wants to start a family.

Archer also discovered that Shirou was actually an orphan who was abandoned in an orphanage when he was a baby. He was adopted by Kiritsugu after the events of the 4th Grail War as Shirou seemed to get along well with Ilya when they moved to Fuyuki. Also, Ilya wanted a younger sibling as soon as possible.

As Archer discovered all these heartening information, he started having hopes of using the Grail to annul his contract with Alaya as he no longer has to fear Angra Mainyu's corruption of the Grail.

Alas, Sakura's summoning of Merlin as Servant Caster had crushed his hopes yet again as Merlin reveals that just like Kiritsugu's, Archer's wish was also impossible to grant. Despite this however, Archer decided to do everything he can to win the Grail War for Rin and Sakura as he wanted the people he once cared about that still exists in this world to have the happiness that he couldn't grant them in his original world.

The current 5th Grail War was quite gruesome. Had it not been for Archer's alliance with Merlin and Berserker who was Frankenstein that was summoned by Ilya, Archer very much doubted they would have survived their encounters with some of the current war's Servants.

Siegfried who was summoned in the Saber class.

Karna who was summoned in the Lancer class.

Francis Drake who was summoned in the Rider class.

And finally a female Hassan-i-Sabbah who somehow possessed all the abilities of previous Hassan-i-Sabbahs.

All these Servants possessed powerful Noble Phantasms that could have killed them had they not formed an alliance. Also, in the case of Siegfried and Karna who had passive defensive Noble Phantasms, they were remarkably hard to be inflicted with any injury as almost all attacks that were ranked B or lower were all useless against them.

In the various encounters with these Servants, Berserker was forced to sacrifice herself during their fight with Karna to give an opening for Archer to defeat the powerful Servant. The other Servants were barely defeated thanks to the trio's teamwork prior to Berserker's sacrifice.

As for the other Masters, Archer never had the chance to even identify any of them as all of them had swiftly gave themselves up to the church where Caren Hortensia, the Supervisor of the current Grail War, resided. It seems all of them were rational enough to do everything in their power to keep their identities a secret.

With the defeat of 5 Servants, the only two Servants left were Archer and Merlin. Despite that it was supposed to require another Servant's sacrifice, the Grail had revealed itself at the grounds of Ryuudou Temple.

Now, here they are. The current survivors of the 5th Grail War plus one normal person have gathered at the place where the Grail had manifested to use it to grant the wish of the war's victor.

After all that he had experienced and seen during the course of the war, Archer had already decided to accept his fate as a Counter Guardian. A decision that he had made bitterly as he found out that nothing in this universe may grant his wish unless Alaya decided that his services as a Counter Guardian were no longer required. A most unlikely scenario.

The other option was for the existence called EMIYA that is currently in the Throne to become a proper Heroic Spirit. Unfortunately, this requires that EMIYA's legend to become widely spread in his original world. A task that is almost impossible as Archer has no idea how to arrive in his original world other than being summoned in the Holy Grail War and that chance is so slim that it was better that it could be thought as completely impossible.

Not to mention that he only has around two weeks during the course of the war to affect history enough to have his legend become widely spread. He supposed that he could enlist his world's Rin to help spread his legend around but if he was already there it would be much simpler to just kill off his younger self.

However, it seems that all was not lost as Merlin had given him one final hope. A chance to save himself if not his true self, EMIYA, that he was originally part of .The only thing left was to answer one simple question.

Should he take it?

To become a proper Heroic Spirit, he will need to perform a feat so amazing that stories of him will be told even after a few generations have passed and THAT was how legends are born. Unfortunately, in the modern world, acts like saving people are hard to become legends as most of those feats may be replicated by others and as such will not be considered 'legendary'.

Basically, if he wants to become a proper Heroic spirit, his act of saving people will have to be so amazing that it cannot be easily replicated by others so that it would be worthy of being called 'legendary'.

The problem was that Archer was not sure that he was able to accomplish such a feat.

"Archer." Rin's voice, full of authority, that suddenly addressed him made him come out of his contemplation.

"Yes, Rin?"

"By my authority as your Master and this Commad Seal, I order you to accept Merlin's proposal."

Archer only had time to blink before the command that was given set in. Archer felt the compulsion that always comes after the usage of a Command Seal was used, forcing his body to do as what was ordered. Come to think of it, Rin was the only Master between the three present Masters that haven't used any of her Command Seals. The other two had expanded two of their Command seals each.

To think that Rin would use it right now of all times to order him to make a wish, Archer thought.

Although it's a valuable commodity, couldn't she have used it during the war to temporarily increase my chances of winning against the other Servants?

The three of us might not have been in such a desperate situation if she did.

On the other hand, being the war's victor without even using one of her Command Seals shows how much ability she has.

While thinking this, Archer still had enough control of his body to give one last quip to his unreasonable Master.

"So you won't give me the chance to even decide my own future? What a terrible Master I have." Archer said this without really meaning what he said in a mocking tone like he usually does. He already understood Rin's intent. If she can't give him a truly good ending she will have to be content with a semi-good ending, was what Archer thought Rin was thinking.

He wasn't expecting to be hugged from all the females present though. All the girls had tears flowing from their eyes too.

"Aren't you girls too old already to have a group hug? And why are you only watching all this? Shouldn't you be jealous that your wives and sister are being affectionate to another man, Emiya Shirou?" Archer tried to be his sarcastic self to hide the little embarrassment he was feeling from close contact with the females that he had once and most likely still loved.

"Well, technically you are me so I don't have any problems with them hugging 'me'." Shirou said without an ounce of jealousy. He figured that Archer at least deserved one hug from Rin, Sakura and Ilya for protecting them. Also, his wives aside, Ilya has shown signs of being quite smitten with Archer.

Surprisingly, Shirou doesn't have any problems with that at all for some reason. He was always quite protective of Ilya as the only male sibling she has and would try to shoo away any would be boyfriend that didn't meet his standards, something that his father, Kiritsugu, encouraged.

Finding out that his sister had a thing for his alternate future self was quite a confusing moment but the thought somehow made some sense as he always thought that he was the perfect match for Ilya. The only thing that stopped him from pursuing any relationship with her was because of their sibling status even if he was actually adopted, so perhaps having an alternate future version of himself as the perfect match in his mind wasn't that surprising.

His current wives on the other hand are another matter. He might tolerate them being affectionate to another man as long as it doesn't cross a certain line. Any more than that however and he would make sure that other man, even if that other man is technically himself, would wish that they had never been born.

"Stupid Servant. If you mess up this second chance, I'm going to Gandr your ass. Count on it." Rin said while smiling with tears falling from her cheeks.

"Please take care of yourself more." Sakura added her own parting words before giving him a kiss on his cheek.

"Shirou, promise me that you will have a happy life. As your Onee-san, I won't permit anything less." Ilya said while hugging Archer tightly from the back with her forehead resting on his back. She had half a mind not to let him go but her more rational self knows that this was for the best. If only she had more courage to confess her feelings to him before this. It was quite a strange feeling to have a crush on her own younger brother.

It's a good thing that he was wearing armor, thought Archer. Excluding Rin who still hadn't developed much even after 10 years, Sakura's and Ilya's breasts have grown more than what Archer remembered them having.

Having finished what they have to say, the girls ended their hug to allow Archer to face Merlin.

"Are you ready, boy?" Merlin asked.

"Yes."

As soon as Archer said that, Merlin started his chanting and prepared to cast his Mystery using the power of the Grail. Not long after, light enveloped the Counter Guardian as it transferred his soul to a different world to be reincarnated.