Dark Brotherhood

The Dark Brotherhood is the most obscure of guilds, only approaching you with an invite to join if you perform the heinous act of murder, specifically of a murder against someone who bears you no ill will and belongs to a non-evil faction. This can be almost anyone: a shopkeeper, a guard, a beggar, etc. Almost anyone will do, although you of course don't want to kill someone who will be critical to the game later on. Of course, bandits and random humanoid enemy spawns won't count. If you want an easy target, we'd recommend heading to an out-of-the-way hamlet or an inn out in the game world, waiting until the middle of the night, then sneaking into a home and murdering the inhabitant in their sleep. (You might be able to claim a murder by killing someone at a Daedric shrine, assuming you've already completed the quest at that shrine.) Just make sure it's not someone that gives a quest. You can tell whether or not they'll eventually be important by looking at your cursor as it's placed over their body; if it comes back as a crown, they'll figure into a quest at some point. Truly critical characters can't even die; they just go unconscious.

After your murder is performed, sleep in a bedroll, such as the one in your home or outside the Vilverin ruin, and Lucien Lachance, a Speaker in the Dark Brotherhood, will appear and offer you the opportunity to join the guild, which is essentially the Assassin's Guild for Oblivion. If you refuse him, then he'll never bother you again, but if you accept, he'll offer you a task: an initiation murder, if you will.

A Knife In The Dark

Your first task for Lucien is to kill Rufio at the Inn of Ill Omen, on the road northwest of Bravil. If you inquire about Rufio there, you'll learn that he's in a set of private quarters downstairs from the main establishment. You can find a little trap door leading downwards underneath the stairs.

Now, Rufio somehow manages to remain asleep for most of the day, so he's not exactly going to be much of a threat to you. If you don't wish to kill him without knowing why you're killing him, you can wake him up and talk to him - he'll imply that he himself happened to kill someone at some point in the past. Alternately, if you want to take advantage of an easy way to increase your Sneak skill, feel free to enter Sneak mode and rubber band your controller into place, or place something on your movement key, so that you're constantly moving into the wall. You'll constantly gain Sneak while you do so, and since Rufio rarely wakes up, you'll be able to just let the game run and gain mad amounts of Sneak ability while you do so.

Poor Rufio. He'll never know what hit him.

Regardless, there's no escape for Rufio, so kill him in whatever manner you see fit, then return to a safe location and hit the sack to speak to Lucien again. When you do so, he'll point you towards the city of Cheydinhal, where this cell of the Dark Brotherhood is located. If you pick the lock on the boarded-up home that's on your marker, then head into the building's basement, you'll find the entrance to the Dark Brotherhood hideout. Say the phrase that Lucien gave you (it won't appear as an option unless you spoke to him) to enter.

Looking Around The Sanctuary

Speak to Ocheeva inside the Sanctuary to get a run-down and some very nice light armor, then start poking around. In one corner of the main room, you can find a Wolf Queen, Volume 6 book which will increase your Sneak skill by one point. In the Training Quarters, you can find Ahzirr Trajijazaeri, which increases Hand to Hand. In the treasure chest in that room, you'll find The Rear Guard (Light Armor) and The Gold Ribbon of Merit (Marksman).

It's in the Living Quarters that you'll find the best loot, though. Keeping in mind that one of the Five Tenets of the Brotherhood is to not steal from fellow members, you can break into the chests for each of the members in your little clan to steal their goods, if you wish. Teinaava's chest has some interesting archery equipment, including The Black Arrow, v2, another book that'll add to Marksman, while Gogron gro-Bolmog's chest has some heavy weaponry. Obviously enough, you don't want this to occur while anyone's around to see you, so either sneak amongst the sleeping guild members or come when there's no one in the room. We found this occurred around midnight to three in the morning.

If you are caught stealing or pickpocketing, then you'll find yourself facing off against...a loading screen? That's right; by breaking one of the tenets, you're immediately expelled from the guild, and supposedly escorted off the property. You'll have a chance to get back in, but hey - might as well do things right the first time.

Note that M'raaj-Dar, who often hangs around in the living quarters, sells a host of interesting items, including Poisoned Apples. If you slip one of these into the inventory of a player, they'll eventually die. Muahaha.