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I think Chris plan is Blackmail. {I don't think so} The lingerie picture and all the text in the beginning we had no control of her doing is going to come into play. For two reasons Chris blackmailing Anna isn't in the cards. First, Chris without blackmail has already compromised Anna's marriage-- technically not once but twice (the kitchen scene & the shower scene.) Second, there is a certain thrill for Chris because it is Anna. Anna isn't the only attractive woman around and far easier ones too. As much as Chris wants to plant his flag in Anna, some unknown factors make Anna more desirable. Personally, I think one of those factors is Chris wanting to one up his best friend David... perhaps Chris resents David's luck marrying Anna or that David was too proud and boastful to have a 10 for a wife.
If a rape possibility happens it most likely will be the janitor. He is very handsy he had the balls to feel her up. Next step would be a breast grab and if she stays an idiot and doesn't report him he will keep stepping it up. That doesn't work either... somehow Marvin (assume the player makes that choice) feeds some inner Anna demon. It's obvious it's not Marvin himself that Anna indulges in his advances, but it's the advance themselves that's feeds Anna's inner demon. I can only assume it's some desire and thrill of the naughty girl inside Anna. It took me awhile to figure out Marvin/Anna route, but that is the most plausible explanation that fits all of the evidence... (Anna's dislike of Marvin himself... her desire to end Marvin's antics... and ignoring Marvin) countered with events what Marvin got away with to this point.