My grandmother recently had a knee replacement and my parents are out of town, so I've been running back and forth between taking care of the grandmother (and her paraplegic cat) and my parents' three dogs and three cats. Makes it hard to sit down and write out backstory thoughts, but here is a little bit more to go on. Since I haven't met any other players to give a description yet I'll just throw it up here.
Because he couldn't really participate in normal childhood play and he spent most of his free time reading and later practicing magic he has a pale complexion. He has dark brown hair a little past his shoulders and wears a few plain black hair ties on his wrist so that he can put it up when needed. He has the start of an impressive beard, bushy and almost five inches long. He started growing it when he was 16 so that he would look less like a child, though his adult thickness makes that less of a problem now. His preferred (armored) clothing is non-descript black or dark green cargo pants, a dark to neutral colored long sleeve shirt, and his old black workboots. He wears a belt pouch with a flap that snaps closed to hold his reagents. His illusion sustaining focus is a Buddhist prayer bead style necklace (
http://www.ksitigabha.com/images/buddhist-prayer-beads-M090.jpg), the health one is a thin, clasped bracelet that is covered in hair tie material so that it blends in with the others.
His oldest friend and best friend are the same, his old tutor John. Almost 50 years old now, John (human) was born to employees (also human) of a small travelling circus that had incorporated some Awakened into their acts to try to stay relevant in a world turned upside down. When he came into his own abilities he was trained to use his magic as part of the show. When he was about 30 his parents died and he went his own way and settled in the Richmond area, tired of the constant movement and rigors of the road that kept him from really exploring new and different aspects of magic. His real gift continued to be for illusion magic, which helped form the bond between him and Cheshire. When Cheshire went off to school John told him not to call him a tutor or teacher any more - they are now simply friends who share an ability and a passion. John is very largely responsible for getting Cheshire to start to come out of his shell and have more confidence in himself and his gifts.
Cheshire's problems with other kids growing up left him with little desire to socialize with people his own age, so he was never one to make friends even in college. There were people that he had a mutual respect with and studied with but none that he would call a real friend. Females are something he had very little experience with until he went off to college, where his magical gifts put him on a more even playing field. He's not virgin-level awkward around them any more but he still has little experience and has never been in a serious relationship.