Step 1: Disinfect
You're going to want to clean off your tunnel or plug (whichever your using; I have a tunnel). Use warm water and antibacterial hand soap.
Step 2: Get Teflon/electrical Tape
I have strips of electrical tape handy. They don't need to be large. Enough to wrap around your jewelry.
Step 3: Wrap
Pick a spot and lay down an edge of your tape and simply circle it (sticky side on the jewelry obviously)
Step 4: Cut the Edges
The edges if the tape will stick off the front and back. It's best to trim them, if only to appear neat
Step 5: Clean Your Ear
At this point my ear is large enough to clean by sticking a q-Tip in and wiggling around. If you have a smaller size run warm water over your ear and rinse with antibacterial soap.
Step 6: Put It in
I use the bottom of the jewelry as an anchor and push down until the other side pops in then fit it round. Your personal methods work too