I went to Otakon last year with a friend. It was the first big con we had ever gone to and we cosplayed and everything. It was such a blast. We both gophered and as terrible as that sounds it was a lot of fun. I think the best part though was walking down the street as Sasuke and having some non-otaku come up to me, ask me is I was sonic the hedgehog and then take a picture of me. He then walked with us and said sheepishly he didn't want to insult us but sonic was the only cartoon character he knew that wore blue. I just laughed.
After that I ended up staffing our local con, Bakuretsu Con, in Colchester VT. Its a small con but its so much fun. And because its small everyone knows everyone else there. I can't wait to staff it again this year.
I am also looking forward to Anime Boston. I was told that AB is the best large con in the east. It will be my first time going this year so I am hoping everyone is right.