the first "Jenny" stories from a Yahoo group (Biker's one I think) at the end of the nineties where basically this: descriptions of the titular character loosing her whole wardrobe one piece each time in a series of unlikely events, sometime accidental, sometime maliciously planed. I believe Biker fully illustrated one of these, I'l try to find it. Later stories focused more into humilliation and skipped faster over the undressing part.
"Owen" series from Gao also followed this line, although here the titular character telekinesis was to blame. Funnily the "accidents' " descriptions were mostly from a casual observer point of view, giving the feel of real accidents and a really nice twist to the narrative. Wish I could find more of the 5 I've got from this series (if they exist...

).
Right now "Meepo the Kobold" (and alliases) and his writing colleagues (
http://princebuffoon.deviantart.com/) are my current source of this kind of stories. Captain Quixote from this same forum also writes this kind of stories, check the fiction section.
Will keep browsing my collection in search of more...