I have found that the best way to stretch ear lobes, when you are any size smaller than 0 gauge, is to either use spirals (picture a) or tapers (picture b).
Picture A:
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Picture B:

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omg!i went from a 20g to a 14g.then i kept going on up from there.now im at a zero and i want to go up to 5/8.they really didnt hurt me at all.the only ones i would say that hurt were the 0g.cause i had to stretch it a little with part of a pen.which is kinda dangerous...but im a risk taker.anyway i used tapers from 12g and up.
got a pair of 10 gauge lob es done yesterday, Didn't hurt, and it barely bled. If you want them, why wait?
-scott 
i had my lobes pierced at a 10 gauge years ago, and started to gauge once they healed. im at an inch now. the initial piercing didnt hurt too much but it did pich quite a bit because of the large gauge size. stretching is what sucked, but just dont skip sizes and dont take too long to get the tapers through; get it over with =]
Some thing not to do! I have a 2g in both lower lobes and 10g in both upper lobes. I like'em but it came with a price. I listened to an idiot that said i could stretch every 2 weeks. i went from a 16g to a 2g in 2 months! (not recemmended) listen to a pro. piercer not your buddies!
I have to say, when i had my ears done, it wasnt the "big" hype i thought it was going to be. It doesnt hurt that i had gotten to know my piercer Emily at Addictions here in Salem,Or pretty well, so i had a pretty good relationship with her by the time we did the deed.
I think She did my right ear first, then after about 5 minutes or so,the left. Instead of the CBR, i now have a Tribalistic LOOKING piece in each. ( pix to come as soon as i can get some taken:-P )
My girlfriend would only agree to have her nipples pierced if I would get my ears pierced. Since I really wanted her to have pierced nipples, I agreed and had my ears pierced two months ago. I don't understand now why it ever took me so long. I love wearing earrings and am planning to get at least 5 more piercings in each ear in addition to having my septum pierced.
I first had my ears pierced along with my nipples 45 years ago when I was 20. I had to stop wearing earrings when I got my first job after college and never wore earrings again until two months ago. Finally, after my wife kept begging me for the last ten years to get them pierced again (I am now retired) I decided to go to a store in the mall and have them done. Actually, since I was at it, I had each ear pierced 3 times (twice in the lobe and once in the cartilege at the top of the ear. All my piercings are completely healed so I can wear rings in all of the holes.
nicky is so kool!.. made it seem painless,, well, not as painlful.. i did go from 10g to 6g so it did sting a little!.. looking forward to more pain!!
Well I got it done once again and this time the proper way. When I say proper I mean by going to a piercer and having them use a needle. I first got my lobe done with a gun 17 years ago. Anyways it was done at a 14g and I don't plan to stretch it too big. This is definately the easiest piercing to heal.