Ah okay! To unlock that image, you need to hang out with Riley on the afternoon of day 2 and focus on the sexual aspect of his first time. So the following choices once you ask Riley if you two can talk:
1. Tell him about the assignment (or go through the "Ask about his day" sequence)
2. "How'd you go for it?"
3. "That's really hot."
And that should unlock it!
Sure! The duo/trio CGs from the end of day one were locked behind whether or not you said you thought all characters included in that CG were hot. The duo in that CG is Owen & Julian, so if you click the "he's hot" options during their intro at orientation you'll be able to unlock the CG during the fantasy section at the end of day 1.
