Sorry 4 bad English:
After you talked to Elena about Chris, go meet her (balcony) at 14:00 Wednesday, CLICK the "TALK" button showed on HER HEAD, NOT the one on the belly, then everything must go right.
Go to Annie's room at 23:00 anyday, you will have to be in the scene where you can kiss her boobs, there will be a circle on her mouth, there you go (get the pic)
The Annie bed scene has this problem: You wont be always in the needed scene, if you meet Bill in the room, re-enter till he's not there anymore, if you're not in the boob scene (the other 2 scenes : goodnight kiss only, butt jerk), save and reload till you in. (Or you can just go 23:00 another day testing your luck).
After that talk to Elena when she's alone, she will tell you to meet her at 14:00 Saturday. Beware the talk icon near her head and go with the flow (Chris anal and semi 3p). That night when you go to bed, Chris will show up and sleep with you.