I guess I should have said what I ride, right now it is a hybrid type bike (pretty much a mountain bike looking bike) & last year I road 50 miles once on it & then a lot of 25 mile & less rides so that is why a road bike will be the first thing I need to purchase.

I'm looking for a used bike because I don't really want to spend $1,000.00 right now.

I do have a helmet, some bike shorts, but not that chamois stuff you are talking about.
I will also need to get some clipon's as well.