It isn't that hard after you figure out the time-table for each character (there might be a minor difference on the Sharing/Cuckold path). Either sleep in Karen's or on the couch to trigger the special events aka story progress.
In between the time table you have to workout, learn how to massage (through the phone) and work in the restaurant.
| Karen | Nicole |
6:00 | Bedroom | Bedroom |
7:00 | Kitchen | Bathroom |
8:00 | Pool (Swimming) | Bedroom |
9:00 | Bathroom | Kitchen |
10:00 | Living room | Pool |
11:00 | Bedroom | Living room |
12:00 | Pool (Workout) | Bedroom |
13:00 | Bedroom | Bedroom |
14:00 | Pool (Sunning) | Beach |
15:00 | Bedroom (Masturbation) | - |
16:00 | Office | Bedroom |
17:00 | Office | Pool |
18:00 | Bedroom (Pay rent) | - |
19:00 | Beach | - |
20:00 | - | Living room |
21:00 | Bedroom (Clubbing) | - |
22:00 | Bedroom | Bedroom |
23:00 | Bedroom | Bedroom |