First: Are you sure you are at a 14g? a standard ear piercing is usually an 18 or even 20g. And no, you should never skip sizes. even for the smaller sizes the fistula (the inside of the piercing, if you will) can be stretched to double its previous size. This can cause rips, tears, blowouts, and infections and is not good at all for you're ears. To avoid problems and unattractive looking ears, slow and steady are the way to go.
Second: Generally, no. While it is true that people's skin elasticity is all different and some people can even sleep with no jewelry in, a fresh piercing generally will not retain its size with no jewelry in for a long period of time. As an example, I lost a plug in the ocean on the fourth of July and couldn't get to another one til the next morning. It had shrunk an entire size! (and my ears were completely healed for several months)
Third: Well.... here's my ear at 4g
http://www.flickr.com/photos/thegreyeye ... 961653381/there are a few other pictures around this site of similar sizes.