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I suspect "octopi" became popular for practical reasons: "Octopodes" is just too different from "octopus" to sound like its plural. Following the usual English rules of plurals, it would be the plural of "octopode" not "octopus". On the other hand, saying "octopuses" risks spraying spittle on your audience. Probably more important, and no thanks to James Bond movies, it sounds too close to "pussy", whose slang meaning appears to be making its legitimate meaning taboo in polite conversation. People have become nervous about saying it, so they prefer an alternative. "Octopi" does the job.
"Virii", on the other hand, I believe originated in techie jargon (I would have said "hacker" but it would be badly misconstrued in this context). It was created by people who like to play with language just as they like to play with technology, and sometimes get silly with either one. (the extra "i" probably was added because "viri" doesn't look right) If the rest of the English-speaking world decides to adopt a bit of techie silliness, it can work its way into the language (that's how we got "chad" after all). Then we start getting into whether dictionaries are descriptive or prescriptive. Before you go with the latter, remember the etymology of "pea".
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