Anagrams of TailboneLust:

LUBE ON LA TITS, LUBE LOIN STAT, LUBE AT TONSIL (think about how it would get there), NO LUBE AT SLIT (uh oh, that's not good), TIT BONE US ALL (that's one lucky guy), LA OLD TIT NUBS

Anagrams of StaleFreshness (my AIM screenname):

SHE RENTS ELF ASS, LETS FRESHEN ASS, HE LESSENS FARTS (by acting as a plug), SELF SENT RASHES

[...and the winner...]

FLESH ENTERS ASS