I have one character involved with Iscariot, but he doesn't really want to be. Sheldon Wilcock joined Iscariot after a rather negative impression was left on him by VC, and he thought that Iscariot were just looking to support those outside VC enough to stand up. By the time he realized what he was really involved in, it was too late. It's a secret, but he has a wife to protect and he has no choice. (Well, he could sacrifice himself and his wifes life but...)
Two other characters of mine are a mother-son duo, Francine and Cedric Smith. She is a timid, elderly lady and is very shy, but sweet. Sort of the typical lovely grandma figure for everyone you know? She works at an inn as a barmaid, and she has mixed feelings about Iscariot and VC... She just wants it all to stop. She has lost her son, her grandaughter and almost lost Cedric in this Iscariot vs. VC feud.
Speaking of Cedric, he lost one arm in the train bombing and has been under a bit of pressure ever since. He also recently PUNCHED THE PRIEST so although he's generally a good, quiet, respectable man who does have a bad rep. running around. He's nice though. <3 I promise.
Harmony Gold is the last of my characters. She was a teacher, was outed as a whore and has been working as one since. She also has a bit of a bad reputation but since apologizing it has slowly been getting better. She's a nice woman, though prone to be a bit hot headed, and she's single. Hint hint, wink wink, nudge nudge :P
If any of those inspire you, let me know. A big question I have is wether or not your boy will be dabbling in the red light district. I also run an NPC pimp so your business is his business ;P