I love the look of stretched earlobes with nice jewelry in it, and personally I don't hate the look of a healthy naked stretched lobe where you can see through it. It's a little less "cool" when the lobe is unhealthy or too thin though, gotta say.
I decided to stretch my ears in March or April and got myself a kit with sizes 14g to 00g with tapers and did my first stretch early April (14g). It was a weird feeling with a little bit of tingling heat when I put in my 14g tunnels.
I've been a little bit impatient since, sizing up to 12g after 1 week, 10g after 1 week and 8g after another week. They were easy stretches though that just slid right in mostly and I was able to remove the tunnels to clean them in depth almost right away without any issues putting them back in (no real need for tapers).
Going to 6g though... a different story! I knew that 1 week between stretches was not ideal and normal but again, in my impatience to get this done, I tried after about 2 weeks. It was not going in at all -- AT ALL. I decided to try and stretch it little by little with the taper every couple days from the back and the front without going all the way through, to hopefully loosen it up. After nearl 1 month at 8g, I pushed a little harder and got the taper fully through... But seriously, it was not painless- it was not just a slight tingling and it was a MISTAKE!
My secound ear was more stubborn and I felt the need to get that one done too at the very same time, so I pushed quite hard to get the taper through and it hurt... I slept with the tapers in that night because I was sure I wouldn't be able to get the tunnels in because of how tight it still was... The next morning, I got the tunnels in just fine, but there was a burning sensation and throbbing, and it was still present a couple days later... Proof that this was seriously not a good idea!!
I noticed that one ear was emitting clear fluid and I decided to sanitize it and there was actual blood. THAT was it for that ear and I downsized back to 8g which is where it's at now. The other ear feels good at 6g about 2 weeks later but I have no plans on trying to shove 4g in there, none AT ALL for a while. If close to a month was not enough last time, then I'm not even thinking about it until both ears have been at 6g for a month and a half... I will wait until my smaller ear can take 6g without the taper before starting the "countdown".
People, be careful about your stretching and see it as a lifelong investment! If you want to be able to wear your ears naked and look good (which you no doubt will do at some point if you keep them for years and years), you need to take it slow. Good luck!