i had a problem similar to this problem. I've had an earlobe peircing since february, i didn't take out the earring for about a month. When I took it out, it would go through the front hole easy but it would be a little difficult to get it through the back hole. I managed to get it through though.
Now about 2 weeks ago, i bought one of those 20 dollar earrings and I slept with it on knowing that there was a little pain, but didn't pay it any attention. when I woke up, it was hurting, so i took the earring out, felt a lump inside the ear, tried to put the good earring back in but still couldn't get to the back. I drained the ear of the pus as much as i can, but eventually it just lead to me leaving the earring out n letting the hole close up.
I plan on getting it pierced again when i can afford good earrings. So most likely you just have to keep them in for a long time and keep rotating them and cleaning them to hopefully avoid the problem of it not goin through easy.