Technically this was suppose to be the 5th drawing that I was going to start during my most recent Picarto stream. In celebration of International Talk Like a Pirate Day on September 19th this was an all pirate theme stream.
 
For the final hour I was taking requests from folks in the chat. I got many, many good requests but 2 stood out to me. One was of an anthropomorphic, pirate Fluttershy and baby kraken  
The other request was for Sunset Shimmer as a software pirate. My original plan was to work for half an hour on Flutters and switch to Sunny. However I lost track of the time and decided to just focus on shy horse, and I said I would work on Sunset after the stream.
 
One of the things I was taught when I was learning illustration was to go for the simplest composition when possible. Eliminate unnecessary elements, components, and material. You wanted to distill down the message to its most basic level when possible.
 
For this piece I decided to portray Sunset as she was at the start of the original Equestria Girls movie when she was still the villain at the Canterlot High School. So I put her in a The Pirate Bay baby doll tee shirt.