The second trial would come to Aemon when he was a man of 35 years. As a measter Aemon had worked for a lord of little mention or power and after many years had his father Maekar requested that Aemon should work in the Red Keep in Kingslanding. His stay at Kingslanding did not last very long because Aemon felt that him being on the small council would displace the grand measter.
After that became Aemon the measter of Dragonstone for his brother prince of Dragonstone Daeron his wife Kiera of Tyrosh and they're sweet but sadly simple-minded daughter Vaella. Aemon was the Measter of Dragonstone to the day Daeron died of a pox he caught from a whore leaving behind Vaella as issue.
In 233 ac was Aemon summoned to court where the a council had gathered after Maekar had died fighting a rebellious lord on the Dornish marches in the peake uprising. Since Aerion, Aemon's oldest brother had gone mad and died drinking a cup of wildfire believing it would turn him into and dragon, A council had be gathered the chose a successor after Maekar. The council for a brief moment considered both Maegor and Vaella but decided against it since Maegor was Aerion's son and they believed that his father madness where in him to the second reason being that he was know a Maegor the cruel. Vaella was turned down because the council felt that the ruler of the seven kingdoms should have they're wits about them. From there on the council seemed to favor Aemon's claim to the iron throne and offered him the crown. Aemon could not believe it, He could be the kings of the seven kingdoms like he dreamed of when he was a young boy and now he could truly become what he once desired. Aemon considered it for a long time, The descition threatened to tear him apart but after long time he declined the offer and said that his younger brother Aegon would suit the role better.
Aemon stayed in Kingslanding for a fortnight after Aegon took his place on the iron throne, Considering where to go from there. He spend his days with his sister and brother who all by now had kids. When looking back at it now Aemon could sit there for the longest time listening to his sisters Rhea and Daella sing to they're kids. After what seemed to be a age decided Aemon that he would take the black and become the measter of the Night's Watch.
The fortnight passed quickly after he had decided to join the Night's Watch and before he knew it he was standing at the ship pier of Kingslanding about to take a ship to East Watch by the sea. Aemon had said his goodbyes to Rhea, Dealla and they're kids but even after trying to say goodbye to Aegon he had insisted to come see him off from the pier. Aemon could still see the kid Aegon once was in him and that was something that had to change for being the sweet and innocent person Aegon was could easily get him killed especially after he got crowned king. Aemon putt his hand on Aegon's shoulder and smiled at him this was truly goodbye.
"Aegon kill the boy it takes a man to rule, An Aegon not an Egg Kill the boy and let the man be born" Said Aemon to Aegon with his hand still on his shoulder.
"I know brother, Don't worry about me i will manage just fine" Said Aegon sounding a little sad.
"Good luck Aegon and goodbye i love you little brother" Said Aemon after sometime of silence.
Aegon smiled and pulled Aemon into a big hug and held him tightly for a little while.
"I love you to brother and good luck to you too" Said Aegon as he realized Aemon from the tight embrace.
Aemon got on the ship and that was the last time he ever saw one of his siblings ever again. Aemon doesn't really remember how long the boat trip took but it was long journey. it was a long walk to Castle Black from he arrived at East Watch by the sea. After that he pledged himself to the Night's Watch from that day until his last. There was always something to do at Castle Black be it help injured rangers and night's watchmen or sending ravens to different places in the seven kingdoms. From time to time he would hear rumors about King Aemon that was more then well liked by his people. After many years in the Night's Watch did the winter finally arrive and with it a great lack of food for the people of the north witch King Aegon helped by sending grain supplies the whole seven year long winter.
The years passed quickly and much to his surprise a character from the past came to visit him. The last time Aemon had seen her she was but a small girl of maybe 12 but now she was a woman grown. Aemon's niece Rhaelle and her husband Ormund Baratheon came to Castle Black with prisoners that wanted to take the black rather then other punishments. Rhaelle and Ormund's stay was not long but long enough for her to tell him all the small and big things that have happened in Kingslanding.
The year 259 ac was a sad one for Aemon because of the tragedy at Summerhall where his last sibling Aegon and his son Duncan where killed in a freak fire. Aemon's once thought that his second trial was about the crown but after many years of contemplation he realized that the real trial was saying goodbye to his siblings never to see them again. Aemon may have lost his real family the day he left Kingslanding but in turn he gained hundreds of brother after joining the Night's Watch.