Maybe it was sort of like the "Eggses!" riddle, where the riddle made Gollum remember something he used to do or have but no longer did. Gollum must have been wearing some kind of clothing when he entered the Misty Mountains and seeing as he may have been wearing leather or tough fiber, it probably lasted for a while - long enough at any rate for him to get in the habit of collecting stones, goblins' teeth etc. That said, I sincerely doubt that any article of clothing could last 500 years, especially in that damp atmosphere. Probably the clothes fell apart and Gollum was naked long before Bilbo ever met him (he doesn't seem to have had too many victims besides goblins, who seem uninterested in any sort of clothing besides armor). Hey, it was dark and close down there - no reason he shouldn't get used to it. But Bilbo's question probably made Gollum think back on those sorts of things, and remember what he had in his now-long-gone pockets.
Just a theory. I don't like accusing Bilbo of inventing post hoc melodrama unless it's absolutely necessary [img]smilies/smile.gif[/img].
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Father, dear Father, if you see fit, We'll send my love to college for one year yet
Tie blue ribbons all about his head, To let the ladies know that he's married.
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