there's a sort of mixture of stats that make it easier, though I believe you can bypass a fair amount by getting drunk first (just don't overdo it). First easiest scene you can get every time is with the reporter, let him approach you, be honest, and just let the scene play out. from then, work at the bar, eventually the school will open up as well though it takes a while to unlock regular soccer scenes, dance is unfinished, and school sex propositions are inconsistent. Haven has a few scenes, mostly rape, and can get you the broken trait which is mildly disturbing (well written) and makes sex easier to obtain, slut perk i've only been able to get with cheating.
slut perk? you can get it without cheats if you do the bar quest and letting simon fuck you. from there attend school and constantly play with the soccer boys till you get to the after school 21:00-02:00 scenes. Once there, you then proceed to "hang out" until you get the option to fool around with them(you acquire a heart button when you approach them after hours) continue to have sex with them. It doesn't charge them money so it doesn't count as prostitution, also, it's completely consensual and not rape. continue this and you get the perk without cheats.
the objective to get the perk is to avoid the other 3 routes - pure(virgin), prostitution(whore), and rape(broken).