Needless to say, this is a nickname for a very specific kind of dude, not specifically one who plays chess.
This is the kind of guy who always makes all the right plays, and receives an ungodly amount of rizz.
The "right plays" is originally based off the terminology used in the game, Chess.
Person 1: Hey! Did you see that sick guy at the party?
Person 2: How could I miss him?! He was a total Chessman!
Cigarette: Northern slang for a cigarette, used oft by mashed up mancunian ravers becasue of the resemblance of a hot(electric)stove to the end of a lit cigarette. Originated circa 1991 in the early halcyon days of the rave culture; we speculate during a drug fuelled hallucination by said manc.
'fuck me noel, i am bolloxed, is that a ciggy in your mouth, or the stove from me 'nans kitchen'/
General use: 'Give us a stove you cunt'