I'm glad you're enjoying the game :) For that CG, you need to do the following:
- Pick "He got so hot!" when you first meet Matt
- Choose to go to Matt's apartment instead of to your dorm room
- Pick "Holy fuck, boy!" when you first meet Leo
- Play through to the end of Day 1
- During the fantasy sequence after orientation, pick "My mind's wandering to Matt's place..." and one of the options should be "Matt and Leo had to have hooked up..."
That will unclock that CG. There are a few chances to have Connor express his attraction to either guy aside from the choices above, so as long as Connor actually meets Leo and you had Connor think both he & Matt were hot, you should get it :)
