Six Months Later
The Greybeards
The Greybeards had been training their apprentices for the past six months. Despite their indifferences and the constant sparring they are now finally proficient with the Thu'um. Although proficient may be too strong a word; they all knew the base shout "Unrelenting Force" and another of which they were taught individually by Arngeir to which he thought suited them best, but they had never used them against a real foe. So in theory they should be able to hold their own against the Dragonborn's lackeys.
Many would argue that this rag-tag team of disorganised misfits would be no match for the Blades. The Blades were considered the best fighting force Tamriel had ever seen. They had strength, discipline, organisation, the Thu'um and the Last Dragonborn commanding them. So what could this militia possibly do to the Blades? It was in fact their very weaknesses that gave them their advantage! The Blades were trained to counter all known fighting styles and types of armies.
So what if they weren't fighting a specific style?
Or multiple at once?
Each of the Greybeards apprentices were unique in their strengths, weaknesses and styles. Remy had intelligence and cunning coupled with Dwarven machinery. Roggvar had immense skill with a bow, dagger and is rather confident, easily underestimated. Anaya's lust for power, selfishness and temper makes her a force to be reckoned with, rage is a hell of an anaesthetic. Virk is sensitive and skilled, a deadly duo, you can do little when those normally quiet are no longer so. Humbungala, the powerful mage is a great boon to the group as he counters their lack of proper magic, however is he to stay on their side much longer?
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The Blades
Meanwhile Destrik and Seryn had successfully returned to Sky Haven Temple. Malitiasicarius was intrigued by the information of this militia the Greybeards were forming but even more so by the new arrival. The Dragonborn at first questioned the reasoning of kidnapping the Nightingale (Something he noticed as well was the fact that she was a Nightingale) but the girl seemed to be acclimatising well to the Blades. He thought it strange that Seryn so willingly joined him even after she was part of a group dedicated to killing him, though even if it was for less than a day. This caused the Last Dragonborn to distrust her to some degree.
Destrik was praised and rewarded appropriately for his duty and the information, although was scolded for his recklessness with bringing Seryn with him. After hearing the full story Destrik was forgiven and his master became rather concerned that this group of amateurs defeated one of his best agents, even if they did have a Greybeard with them.
Over the course of the past six months they had both earned the Dragonborn's personal attention. Destrik was soon promoted to his second-in-command and he found use for Seryn as one of his personal assassins. Destrik was assigned to teach Seryn the discipline and ways of the Blades as Malitiasicarius taught her the Thu'um, again in the way the Greybeards taught their apprentices. Although the other shout she was taught was far more brutal than the Greybeards would dare teach their apprentices.
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Malitiasicarius was planning to meet the Greybeards trainees. He was also planning his boldest move yet, he planned to invade the capital of the Reach. Markarth. Perhaps if the Imperial's still had control over the city he may have thought twice but recently the Forsworn had taken over the city. They stood little of a chance against the Blades. There were three reasons he was planning this:
The first reason was that he needed to establish a proper footing in Skyrim. He may hold a portion of the Reach from Sky Haven but what would ensure his dominace was an entire hold. From Markarth he could start his Empire, leaving one of his men to govern it. Destrik maybe?
The Second was to test the loyalty of Seryn, there is little knowledge that escapes Malitiasicarius and he knew all to well her background. They were taking this city from the Forsworn and he expected her to kill them with no hesitation. Seryn's ultimate test will be to execute the leader of the Forsworn in Markarth. If she couldn't then she would be tossed aside like any other.
Finally the third reason; he was curious about the Greybeards' apprentices and was eager to meet and test them. So the Dragonborn released some discreet rumours that "A small amount of Blades were going to launch a raid on the city of Markarth" which eventually found it's way to Arngeir. Arngeir sent the group to Markarth to stop the Blades there. Little did they know a full army was there awaiting them, led by Malitiasicarius himself with Destrik and Seryn at his side.
The Blades had their orders. Once the city was captured and the Forsworn defeated. They were to capture the apprentices and bring them to the Keep. Malitiasicarius was to give them a choice: Fall in line or be crushed under his heel. None are going to stand in his way.