As far as it being easy or hard to put in, it seems to be different for different people. Some people have no problem & seem to be able to do it on the first try, while others just can't wear them, or get them stuck in their ear, or hurt themselves. Some say just to wait a while to wear them & it won't be a problem, & while you do want to be at a size for a while before you try them, for some just simply giving it time isn't going to do it. I know for me, I didn't wear them for a long time, but I saw these plugs I really wanted that were double flared so I decided to try them again. And I had been at my size for a while, but I still couldn't seem to get them in. Finally what worked for me was putting a little bondage tape around my single flare plugs & wearing them for a few days. Not so much that it changed my size really, it was just a couple of wraps, just enough to kind of loosen the holes a little. It seemed to work, & ever since then, putting in double flares has never been a problem. Even if I go back to single flare or no flare plugs for a few days, when I go back to double flares, it's no problem getting them in. Some people will buy them a size smaller than their current size, but I don't like doing that because they tend to not feel very secure in there & can fall out.
If you haven't been at your current size very long, you may want to wait a bit to try-either way, double flares aren't for after a fresh stretch. But if you've been at your size for a while & you still are having problems, you might want to try the tape thing. As far as finding plugs w/a smaller flare, different manufacturers can vary. But my favorite site for plugs, http://www.bodyartforms.com
, will often give you exact measurements of the flares on many of their double flared styles. So you might want to check that site out & see if you can find a pair that has smaller flares. You may also want to try stone or glass first because it's smooth & slippery and tends to slide in more easily. Sometimes wood may have smaller flares, but since it's not as smooth & slippery it doesn't go in as easily. Good luck!