The Past
How and where one is born determines one's station in life. In this case, Aleister was born into a family with a long standing tradition dating back centuries, if not millenia, of being Knights. As a result, it was obvious the path that the young Charlton was destined to walk.
The younger years of his life were spent learning what it meant to be a noble, raised properly and groomed for what would become his duty in life. When he came of age, Aleister was sent first as a page, then taken as a squire to the Lord Charlton of Hollyhot, his Lord Uncle.
Like anything in life, there were bumps and the occassional bruises. These were to be expected when swordplay and all manner of fighting were being taught and practiced. Aleister showed that he was not a disappointment in these areas, and while he was not as skilled with a sword as the others, he excelled when it came to weapons of bludgeoning nature.
The years progressed and adolesance gave way to adulthood and like many of the Charlton Knights, Aleister had yet to prove himself worthy of such a title. Seeing his chance to prove his worth when Robert's Rebellion took form, Aleister was disappointed that the Charlton Knights didn't ride forth to lend their aid. In fact, when they did ride, it was to King's Landing after the Battle of the Trident and much of the Mad King's forces had been decimated by the Lannisters during the sack of their city. It was here that Aleister received his Knighthood, having been judged worthy to accept the responsibility of being a Knight based on his age, upbringing and skills displayed during training.
With the ending of the war and the rule of King Robt mostly assured with his seat on the throne, Aleister returned to his home, rather then that of his Lord Uncles. It's there that a year is spent in practice and training, honing one skills and participating in drills with the other Knights of Charlton. When the year came to end, he returns to the Lord Charlton's service and to the service of his cousin, Lord Andrey Charlton. It's there that he continued his duty as a Knight, working and continuing to prove his ability beneath the Master of Arms as his assistant.
During this time, only a brief reprieve was taken. One in which he return home to escort his family to the Westerlands, his father, the Lord Charlton's uncle, tasked with further relations of trade to see that the Charlton treasury continued to grow through new avenues. It was there that he met Cherise, a Lady Westerling, and he was smitten by her beauty, something that the Charlton line was whispered to not have. It was her family in which his own was meeting with and during their stay, he had time enough to meet and learn about her. Negotations were completed, far too quickly it would seem for Aleister, and they were gone, returning along the road for home.
Swordplay and fighting were not the only things that Aleister managed to learn, for he seemed to enjoy the art of debate, which for him, could have very well turned into a less then gentle art, were it not for his cool, even temper. But like all manner of debate and politics, one must have a certain knack for deception and a will to play the game and this was something that Aleister found himself enjoying. Ambitious in nature and wanting to further his own station and that of his House, he was not afraid to join into the political fray. It was for this very reason that he set himself to using the power of words. Bending the ear of his mother, who turn bended the ear of his father, that the Lady Westerling would be a good match, should the opportunity arise. Secure relations with the Westerlands. Cement a deal in trade.
Little did Aleister know that at the very time that was trying to move his parents in a particular direction, Cherise was doing much the same. The Westerlings family had begun to fall upon harder times, with the mines beginning to go dry. As such, she began to plant the seed that a marriage with with a family such as the Charlton's would do well for her. Being only a cousin to the actual Westerling line, she didn't draw the attention of Heirs or Heads of Houses, but it didn't matter. Her station in life would soon be set for it wasn't long after that her family requested a betrothel of Aleister. With little hesitation, his own agreed and they married a year later.
Life would be good for a year after his marriage, with Aleister remaining in Hollyholt and serving the Lord Charlton and his son, Andrey. During this course, he was elevated to the position of Master at Arms after the Charlton's former fell ill and could no longer attend to his duties. The role was accepted, but his duties within the actual city would be short lived. At the Lord Charlton's command, a detachment of Knights was to be sent south in the Riverlands and as the Captain of the Guard was to remain behind, Andrey approached Aleister to join those that would venture south and with leave granted, he readied his things. Again, ambition begin to bare its head for with strife amongst the Houses to the south, one never knows what opportunities may arise. As such, he made sure that possession were packed and his lady wife readied, so that she might arrive shortly after he. After all, one doesn't know what one may find and should the opportunity arrive, he would see the Charlton line furthered in Westeros.