Well I finally finished this personal piece. I was procrastinating on it for far too long, but it's finally done. I finished it last night while watching Empire Strikes Back. The best Star Wars movie.
It's a digital piece done after I drew a sketch of my best friend Suijn, the original sketch is in my first post. I set up a flat burnt sienna under-painting in Photoshop then did the rest in Painter.
I used to have trouble in Painter trying to figure out how to get it to properly replicate oil paints, since I normally work in oils. Then one day Octavio Perez showed me one of the most amazing things ever. The best way to replicate oils is to actually use one of the pastel brushes, round x-soft pastel 30 to be exact.
To make the pastel brush work as oils the settings have to be changed. The resat is set to 9%, bleed at 73%, jitter at 0, opacity at about 12%, and most important is the grain must be at 100. By changing the grain it makes the pastel brush nice and smooth while the resat, bleed, and opacity allows it to blend like oils, although depending on which part I am working on I adjust the opacity. It's not the only brush I use but it is the one I use most often, while working. I'll mention some of my other brushes when I have better examples to show of how I use them.
On a final note I'd like to thank Sujin for posing and for all the really helpful crits.