After you stretch, don't try shoving something in that has a flare. If you're having problems with plugs and o-rings falling off, try stainless steel tunnels that screw on. If you're worried about the wearable area being too short (I have made the mistake of buying tunnels too thin for my lobes), screw them on half way, or almost all of the way.
Current Modifications:
lobes stretched to 7/8" (22.2 millimeters), double helix (both at ten gauge), tongue stretched to four gauge, scrotal piercings at six gauge (pierced at ten) and double zero (pierced at 12), and a tattoo on my right calf (don't worry about what it is, my cousin did it several years ago).
Future Modifications:
tattoo consultation March 11th (custom day of the dead skull on left forearm), ears to 1" (25.4 millimeters), tongue to 2 gauge, scrotal piercing from 00 to 7/16" gauge, old-school piece on left forearm, oriental sleeve on right arm, frenectomy, three frenum piercings on top of shaft, possible prince albert, partial tongue split.