Wait, are you talking about Chester or Spencer? Spencer is the only one who can topped or bottomed, and Chester's route doesn't even have any anal sex whatsoever at the moment.
Viewing post in Extracurricular Activities comments
Chester is the bull. Spencer is the husky. I have played through Chester's route multiple times, and the all that's ever happened was a blowjob in the shower and some frottage. Chester has also stated that he is going to be bottom since he is too big for the protagonist. Spencer has had full anal sex in his route, with either him topping or bottoming depending on certain choices throughout his route.