First, I would for sure check out the link that heathdawg posted.
I've used the poor person's stretching kit with great success, and I would definitely suggest it for stretching, at least at smaller gauges. To wear the plugs, you just slide them in your ear without the rings, then put a ring on each side to keep it on. Either side can face forward, and you could even put one o-ring on before you put it in to prevent the plug from falling out the other side. I center the plug in my ear to ensure that the o-rings are able to stay on each side without sliding off. I hope this answers your question(s)?