In The Elder Scroll 5 Skyrim, the side quests of the Dark Brotherhood are the ones that, as usual, at least at the beginning, give you the most trouble. The Brotherhood always hides very well, but we managed to find it and we have created for you this detailed and detailed guide that will help you to become part of the Brotherhood.
The first rule in order to find the hidden fraternity is to talk to anyone you happen to meet around Skyrim and collect as many clues as possible. The moment the quest is activated, SPEAKING WITH AVENTUS ARETINO means you've talked to the right person! So make your way to the Aretino residence in Windhelm, where just before entering you will find yourself listening to a suspicious conversation.
Idesa Sadri, recommends a young boy to stay away from Aventus Aretino because since he returned to the city there are strange rumors about him. If you want to know more, ask the woman for further explanations even if she won't tell you anything of fundamental importance for the quest. Reach, therefore, Aventus Aretino inside his residence (it will be necessary to pick the lock). At this point you will witness a rather macabre scene; a room full of candles arranged in a circle with a skeleton and human organs in the center.
The boy's engaged in a ritual to call someone back. Stop the ritual and talk to the boy who will tell you about the recent disappearance of his mother and the Honorhall Orphanage in Riften where he was sent. Believing you to be an assassin of the obscure brotherhood, he will ask you to kill the sadistic headmaster of the institute, Gredol the Gentile, thus activating the quest LOST INNOCENCE.
To complete the quest you will need to go to Riften and in case this is your first visit to the city, get ready for a long trip. A long journey in a game like Skyrim has, however, its positve aspects. You'll encounter many, many things to explore along the way.
At the BRAIDWOOD LOCANDA, you'll find Dravinea la Tirasassi. The woman will be willing to train you for free to the alteration in exchange for some Frost Climbs. At the Orchard Stronghold of NARZULBUR, you will be blocked by a guard. Talking to the guard will activate the quest SEARCH FINGERS MASTRO FABBRO that will allow you, if you decide to continue, to become a blood relative of orcs. At the STONE OF SHOR speaking with the locals you can activate a series of side quests. Once you've passed this place, be careful, a nice Dragon might pop up. At this point you are near Riften, but before entering the city a guard will ask you to pay some sort of entrance fee, it's up to you to decide whether to pay, intimidate or persuade the guard (I would opt for persuasion, enter for free and increase the oratory!) Once you enter the city you'll find that talking to almost all the locals will activate side quests, and it is precisely in Riften that you will also discover the Guild of Thieves.
You reach the orphanage, enter and you will find yourself listening to the headmistress, Grelod the Gentile, address the children in a very unkind way. After the unpleasant conversation with the children the sour woman will be at your disposal to be killed immediately. If, on the other hand, you are curious or simply have some scruples, before killing her, ask her and the children for information and all doubts will be dispelled. Return to Aventus Aretino, update him on the quest accomplished and he will give you, as a reward, the Aretino family heirloom. At this point don't get scared if nothing happens, just be patient and wait a while! In fact, while you are busy in other quests, a messenger will probably reach you and give you a letter.
You'll need to go to sleep now. When you wake up you'll find yourself imprisoned in a shack with Astrid, the woman will tell you that by killing Grelod the Gentile you have stolen a contract from the brotherhood, this is the reason for your "imprisonment".
WITH FRIENDS LIKE THESE
To be free, you must repay your debt by killing one of the prisoners Astrid brought into the shed.