1)he must not leave the home
2) you need to hack his pc(you have to meet the fan,buy injector,learn hacking from his mom )
3) on thursday you must go to his room and hack his pc
4) convince anna to fuck him
5) do a threesome with him
6) go to his room and talk to him
i also read that you can share samantha with him, not necessarily anna. for that you have to:
1- progress with samantha (her teching you how to hack), then on the final "lesson" she thanks you to keep her company and all that and invites you to go to the beach on mondays. also when you use adrian pc you have to not tell anna about adrian being a subscriber, then just keep progressing with samantha
2- go to the beach and take photos of her and/or apply the oil lotion (i just took the photos and it was enough) and also you have to vist her in her home when she is alone, if i remember correctly its tuesdays (im sure of this one) and fridays (i think) and also take more photos of her until she is comfortable with you so you can have sex with her
3- visit ken and he will ask you to help him lose his virginity, here you have two options, share anna with him or samantha, choose samantha, he will think that youre making fun of him (but wont be angry dont worry). talk to him again and show him her beach photo, then have sex with samantha and you will get an option to take a photo, take it, when you finish the scene go again with ken and show him that photo
4- he will ask you to ask samantha if she can fuck him, tell her that and she will say that its wrong and all that, go back to ken and tell him that he can just join you the next time you have sex with samantha. and have sex with her and he will join you.
5- visit them and ken will tell you that he doesnt know how to swim, offer to teach him, you have to rent the public pool.
from here i dont remember exactly how you progress in order to invite adrian to this pool sessions, sharing samantha with him to starting a foursome scene on the pool
but yeah, i know it long but i tell you this just as an alternative, in case you dont want to share anna with adrian