Perhaps it would be wise just to read the personals for a while and have a nice, safe, contemplative wank when you find something that strikes your fancy. You've already discovered that at least two of your experiments were, for you, better left to the imagination. I can't help but think that there are many more out there just waiting to disappoint you.
Go slow, son. There's no time limit in operation here. As to your last question, there's no contradiction between being a student, a friend, an Eagle Scout, and whatever else was on your list, and having a great, honking, perverted imagination. What do you think your friends are thinking about when they peruse Craigslist? It ain't secondhand furniture or a really great cheap babysitter not yet it isn't.
Andrea is home with the kids and going stir-crazy. Write her a letter! Ask her a question! Send her your tedious e-mail forwards! On second thought, don't do that. Just ask her a question.