I'll do Jason, as he was my first and favorite pirate.
I named him Jason Suncutter because it seemed like a good name. Not ridiciulous like some names... (I'm still glad I named him that) At the time, he had gray pants, gray long sleeve button up shirt, and an old black vest. He rocked a mohawk and a "soul patch" as I call it, the very small beard. I made him the skinniest model, which is bittersweet for me, seeing as most clothes look bad on him, but I couldn't imagine him any other way. I never changed that model until not very long ago, about a year or so. I gave him a tribal face tattoo, and lots of gold and bling.
I got him a black ponytail to look good with that Admiral's hat, and got the Barbossa outfit minus the hat.
Ship History:
Owned one of everything!
Sloops: I named 'em all Lighning Runner
Galleons: All Shadow Mongrels
Frigates: All self-named, yup, they're the Sun Cutters!
Guild History:
My first was my own guild, the Galleon Crashers, All noobs; including me. We reformed it when we got a non-noob, with him as guildmaster. I turned my back and left them after that. I still keep in touch.
I joined a guild that a friend of mine was in. It was called the Twilight Coven, and was full of old-school pirates. Two names to remember, Blackshark and Enrique. :P We were as good as gold for a while, until a group of pirates who shall not be named started causing trouble. The GM was never on anymore, so we couldn't get them properly sorted out. Worst of all, they were all Officers, and kicked whom they felt like, once kicking someone for not raiding Kingshead because they were too high level. That was the final nail in the coffin. Everyone I knew left, and I soon did too.
The Rouge Covenant was the brainchild of myself, Blackshark, and Enrique. A few others also contributed, all members of the Coven. Though Enrique never properly joined until recently, he was a driving force behind it. Blackshark was GM and several others became Co-GM, myself included. We outnumber the original Coven by about 1:1.5, but was made in August!
I still am in that guild today, and the future looks bright.