I got it on the third try, I think
just like in the guide (we tied first, then I won)
you have to wait and keep visiting him weekly, at some point it will triggers after being with him in the morning
also i made a cg guide, if you want here's the link: https://docs.google.com/document/d/1xKhE31i0TlpRMTIlMNNtPZ3Iu2E11KtuMTjO7ukU2XM/... ♡
HEY!! I made a guide on how to get ALL the CG's in the game
for those interested: https://docs.google.com/document/d/1xKhE31i0TlpRMTIlMNNtPZ3Iu2E11KtuMTjO7ukU2XM/... ♡
1st: kiss tocchan - do it a lot in foreplay mode until the you get the scene;
2nd: Sub/Bottom Tocchan, first: get the rope - to get the rope you have to do the sidequest of an NPC outside the TV station (needs to have popular status and access to TV station - that is, bribe the guard, spend 50k), and then use the rope (foreplay mode).
first one: sick shuu - keep visiting him at his house, at some point the scene will happen;
2nd: beach trip CG;
last one: fan meeting
and the shiba's dog costume: dog appears in one of the classes (it'll triggers a CG too), after the dog shows up, the love hotel bear will make you an offer, go to the love hotel at night and the bear will offer you a dog costume (cost: 20k); for the scene to happen, you have to top shiba at least once, after buying the costume, at some point the scene will happen (it took a while to appear for me, so don't worry);