Rule #1 of anal. ALWAYS USE LUBE. While it is always painful at first, lubing up both your cock and her hole will make it easier and more comfortable for entry.
Great video. There is something exotically hot about teaching a women to be a butt slut. Her facial expressions and rhetoric support the first anal encounters, nice to actually see a video with a real anal novice. Tell her she is going to take it in her ass and its going to hurt so just take it verse the coaching approach would work much better.