This functionality exists in desktop programs such as Adobe Illustrator or Painter.
You can select a brush that is a pattern of images. Starting to paint on canvas displays a line (or any pattern) created from a set of images of different sizes and rotations. Approximately how I portrayed in the picture (the red line is a path of the brush motion).

Is there already a library for this effect, or how it can best be implemented?
Listen for
MouseEvent.MOUSE_DOWNon your drawing canvas and once it fires, add aEvent.ENTER_FRAMEto begin drawing. The drawing itself is pretty straightforward – on every frame you take the mouseX and mouseY values and add the PNG image on the canvas in the exact place with any transformations (scaling, rotation, alpha) for that particular image. Here’s a simple example: