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I can confirm that for big D all you need to do is be naked from start to finish, a friend can kill big D, you might even be dressed for the first part, or just before he dies, I don't know that though.
BIG THANKS TO EQUILA, for helping me get the last part of the achievement!
I agree 6 seconds is not long enough to strip. Best not to refresh SW as you will lose too much damage. You could half strip, hit D once, then complete the strip. A big strip tease for the big D! That way your SW is still full strength.
You could also do a gradual strip, keeping character screen open in combat. Just nicking big D every 6 seconds while you strip.
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