I used to do role-playing game art, long before the advent of the elaborate video games that are now popular. I would do a color cover and a lot of smaller black and white drawings which went into the book interior. I never played the game, but the art director and the designers told me what to illustrate and gave me plenty of descriptive text and scenarios to work with. The game company was "Gamelords," based in Gaithersburg, Maryland. It has long since faded away.
This is the cover for "Haven 2: Secrets of the Labyrinth," a game set in an imaginary Renaissance-era port city full of the usual wicked and adventurous characters. In this scene, a prostitute and thieves set up a naive soldier. You can see the thief running off with the soldier's purse, while another one in the alley plunders his baggage. The prostitute makes a hand signal approving the thief's work. Prostitutes wore face veils in Haven, for some reason.
"Haven" cover is acrylic and ink on illustration board, 11" x 14", December 1982. Click for a larger image. Published as a game book cover in 1983. Believe it or not, you can still get this game if you want to play and/or collect it. It is sold here at the "Different Worlds" vintage game site.