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The Elder Scrolls V: Skyrim Game Add-Ons (DLC) Hints
New Allegiances
1 of 5: Anytime after finishing the "The Bloodstone Chalice" main-line quest, ask anyone in the castle what you can do to help, and the game will randomly choose a side quest. If it's this one, go talk to Vingalmo to start it.
2 of 5: Make this quest active, then follow the quest arrow to the person who was randomly chosen to receive the "gift" of vampirism.
3 of 5: If you don't currently have the Vampire's Seduction power, wait until you do. Use it on the chosen target, then activate him and choose to feed. (Or feed on him while he's sleeping without using Vampire's Seduction.)
4 of 5: If you're seen doing this by anyone else, you'll get a bounty for assault. You can either wait until your victim is out of sight of everyone else, or just do it and pay off the bounty.
5 of 5: Return to Castle Volkihar and report to Vingalmo to get three potions of blood or a random, leveled weapon or apparel item. If you don't like what you get, you can restore the autosave that was made when you entered the keep and try again. Doing that may also alter which randomized quest you get next.