Hi there BabyTyrant,
My experience has been that at events like TeddyCon there are some hard lines like no sexual behavior, drugs, etc., but within the space of the event you can come as you are as long as you're not naked and as long as you don't mess yourself (that rule is because of the odor and sanitary issues - imagine if everyone at such an event could do that how bad the place would smell).
If you can go to a munch or an event close-by, that might be an eye-opener for you ... in a good way. The first event I went to, I knew two people via FetLife private messages that I had built up some trust with. I told myself if I got there and got a bad vibe, I could always just leave and chalk it up to an interesting experience. It was certainly a little overwhelming at first, but having two points of contact I could ask about and meet made all the difference. What I think you would find is that you will meet people from all walks of life and from every background who have come together to be and express a part of themselves they cannot otherwise easily in their regular lives.
I would say, too, I'm a middle-aged man finally doing this ... that was quite a hump to get over for me. If you're younger, this is one of the best times of your life to try these things out -- you don't have to worry as much about kids or a career, etc., let alone just making the time. If you can do it, and if it is the right vibe for you, I encourage you to attend something. Don't let FetLife scare you so much that you don't link up with other people -- you have to be smart and careful, like with everything, but trust me ... don't live with regret.
Anyway, I would never tell anyone they should do anything -- but from someone who is just finally doing these things now, I wish I had been braver earlier.
Take care,
Tab