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I need help with a quest for the dark brotherhood where you have to kill the gaurd leader. You get the sanguine rose and they tell you to hit him with it when he has his clothes off. When does he take his clothes off!?!?!

wait for him to go for a swim in the city (near the castle), then strike him. it might be hard not to get a bounty, so use the site 4 help

http://www.uesp.net/wiki/Oblivion:Permanent_Retirement