You are a perv and Ashley is bossy. This combination means she tells you when and how to jerk off and you get to see what she wants you to see. Its for her pleasure and not yours, although you will probably enjoy being controlled by her while you jerk your cock to a girl you will never actually have. Basically you are her bitch, she do anything she says for your next orgasm. She knows you love leggings and high heels, so when she comes in the room wearing that, you know that you are going to feel like her bitch, but also get to cum. So much so, you actually enjoy being a walking little perv