I'm new to this forum and to stretching, so hello!
I've had my ears pierced since I was 3 months old, and I spent most of my junior high and high school years wearing very heavy, dangly earrings. I was, however, also very meticulous with ear care and would always be cleaning my jewelry and such.
When I started to stretch, I started at 16g, and the taper slid right in with a lot of room to spare. No resistance, no pain, no nothing. I had 16g studs in for about a week, then decided to try 14g - I know you're supposed to wait a month, but considering that my piercing was actually bigger than the 16g. The same thing happened - no pain, no resistance. There was a little room to spare but not much. It felt the way that my 18g earrings felt when I was 4-5 years old.
After a week, I figured that I could try 12g, considering that I haven't actually "stretched" yet. The 12g came with a bit of resistance and very little pain. It took about 10 seconds to slide in. I put in the 12g studs.
They're a little sore and maybe a little red (nothing very noticeable), and the studs are pretty tight. However, there's no pus, blood, etc, and it hurts about the same as when my 18g piercing got a little infected from wearing crappy Claire's jewelry without cleaning it. (oops)
Because of all of the posts I see like "STRETCHING SHOULD NEVER HURT EVER", I was wondering if this was normal. I stretched only about an hour ago, so I think that it's okay, but I'd like some opinions.
For the record, my tapers are acrylic (I don't leave them in), my studs have all been surgical steel, and I've been using jojoba oil to stretch and Holey Butter for aftercare. I disinfect everything with witch hazel, but then I thoroughly wipe it off so my ears don't dry out.
(long post, eek, sorry)
Lame. The blowout seems to be gone after a few days of salt soaks and wearing the 14s "backwards" to encourage the tissue to go back in, but I'll still leave those in for a month or two. The 12s fit into the other ear no problem today with no pain or redness. 
