Rick,

Take it from an avid cock-ring user, shave. It's much easier to use a cock ring comfortably is you shave your pubic hair, at least an inch or two around the base.

They're designed (most of them anyhow) to go around the whole package, behind your scrotum.

I use "jelly" rings, which I purchased from JT's Stockroom ($3 each, bought 3). One is rather light constriction, but I can add the other two if I need more.

If the problem is getting hard in the first place, and it sounds like you've got a chemical ED issue, do rethink the viagra. I was 19 when my doctor put me on zoloft (off it, now thankfully) and I was miserable for a month or two until I mustered up the courage to talk to him about it. My then girlfriend couldn't stop thanking me.

You might also try a vacuum pump; I use one regularly, just for enlargement and pleasure, but I do notice that my erections are firmer and fuller all the same. Female friends have commented that I feel a good bit thicker too.