1. In the 1980's a gang in the City of Flint, Michigan was called the Top Dawg's. Many of its members and associates chose names that contained the word "Dawg" (i.e. U-M Dawg, Flint Dawg, T-Dawg). Stingerdawg is a name chosen by one of the distant unrelated associates and City of Flint citizen. While not a member of the gang itself, Stingerdawg supported the Top Dawg attitude that was against the administration, the system and the "man" in general at that time.
2. A person who is involved in Fantasy Sports such as Football, and excels at every level. Also, a pseudonym for Desmond Boulevard, the writer (which is a pseudonym in itself).
"Yo mayn, ain't that Stingerdawg kicken' in the front door of Chumpy Chumpersons casa?"
"Stingerdawg and his Stinging Dawgfish kicked my tail in this weeks fantasy football playoff."