Thank you all for the suggestions! Going in order here:
There are actually two seals: the piston itself and an additional seal between the piston shaft and the body of the pen (which has the small bore in question). The piston seal is intentionally leaky in one direction due to how the ink filling mechanism is designed (see: vacuum filler pens), so the shaft seal is necessary as well, as ink can make it past the piston head. Long story short: the o-ring has to be retained in the bore instead of the shaft.
I did consider a backing piece as you mention, but I wasn't sure how reliable a seal that would be. I'll keep it as an option!
Looks like I didn't search hard enough... I'll keep this one in mind.
Thank you for this resource, very helpful.
The o-ring I have on hand is McMaster P/N 9452K13: 0.101" ID and 0.241" OD. The page I'm looking at has o-rings down to 29 thou ID -- very cute.
Given all the advice on grinding my own part, I think that's the first option I'll try out. Seems like the most satisfying. I'll report back!