Yeah, the game doesn't work well if you don't do things a certain way, which is why i always advice to use the walkthroughKinda tried to play without walkthrough and got some 'hours advanced' into the game so Im really reluctant to start to play from the very beginning. Is there a trigger on Adrianna that activates her giving the cheerleader outfit for uhm Julia(? our 'sister' to help us trick Kira's boyfriend? Idk if you have to do some other quest before but I got to the point where you can have sex with her by calling her to your room and roleplaying as a cop. Had a look at the walkthrough and well... ngl 9999+ steps kinda blew my head.
Anyway, and this just a guess
the steps you're looking for is 431-437
also you needed to have also done the "Cheerleader & jock" with Adrianna, which begins with step 326
Basically you need to build your relationship with Adrianna