Earstretching.net

That's a really cool idea Acacia xD
I don't use plugs yet but I've seen my friends struggle with it before.

Shan; maybe try wearing the tapers for a couple days and then try just sliding in the plugs. That way yer ear is a little more used to the size (:

And since we're using the same taper/plug set, I can tell you this. I read a review on amazon that said the plugs ran a little big. I've lined up all of mine and I didn't really notice a difference but maybe yours do?

I usually put a dot of soap (Dial Antibacterial, though I doubt it matters) between the blunt end of the taper and the blunt end of the plug. This way they sort of stick to each other just enough that when I push the plug in, the taper falls out and I'm all done.

Then again, this would only work with solid plugs. Might work with tunnels. Try it.

either pull on your plugs whenever your just sitting around, if you do it enough your ear will loosen faster then just from the weight of your plug which is probably not much, if your at the right size: chapstick lids have no flares.. lol believe me, ive done it all.
or you could use tape. just one or two layers around your taper, push the plug in, itll feel tight for a day or two but when soreness goes away, im sure any plug double flare or not will slip right in.