I liked the anal vibe and all, but I think it would have been better for the story if Ann told you she was going to the library alone, invited Chris behind your back like in the good NTR route to help her study, you did not realize Chris was there with her and hit the vibrate button wanting to turn her on thinking of you, Ann has the scene with Chris instead, Chris finishes the same way as at his place and leaves as usual, Ann rushes back to you still turned on by the new experience and starts making out with you, you taste something a little different and realize "Oh shit, she was with Chris again" but then you get turned on by it and Ann makes you cum just by grabbing your dick as you make her cum again with the vibrator while you are both still lip locked.

Better than the random nerds to me.