I stretched my ears up a size the other day - I'm a size 6 now.
Some tips for newbies to gauging: skin is stretchier when it's wet, and sea salt helps with healing. Ever since I learned that, I stretch my ears in a hot bath with sea salt in it. First I immerse my head far enough for my ears to be under, and soak for five minutes or so. Then I do the stretching and put in my new larger-sized plug with my ear still under the water. It's so much easier this way! I think this was my least painful stretch yet.
Also, metal is about a billion times more comfortable to stretch with than acrylic, so I'd recommend paying more and going for metal tapers like these. Or, if you happen to be at a 6-gauge right now, do what I did and use a metal chopstick. I found some at a store that sells kitchen stuff; when I hold one up to my gauge card from Body Art Forms, it looks like the small end is about a 6 and the big end is about a 2. For this stretch, I wrapped a bit of tape around the chopstick at the appropriate width so I'd be able to feel how far to wiggle it through my ear. I guess when I go up to a 2 I'll be passing the whole thing through the piercing. Anyway, the chopstick is saving me a considerable amount of money on stretching kits and the fact that it's metal means it's comfortable and can be sterilized.
Eventually, I want to get coloured titanium eyelets. Fuchsia ones! But, y'know, only if I plan to stay the same size for a long time. They're pricey enough that I can't be buying new ones every month.