Looking to play someone not typical in a het based line. Dub-con would be great. (He has something to blackmail her with, maybe).
Basically, anything he can use against her to become his cum-slut. I'm thinking she was the high school prom queen, or head cheerleader, or someone way out of his league ... He's wanting to get back for all of those years that he never got anything out of her. I'm thinking someone a little different like Jonah Hill, Clark Duke, Michael Cera, Rainn Wilson, Danny McBride ... or many others to choose from! I'm not all that picky!
Pretty open on the PB although I do have a few in mind if you are open as well!