We've had my cat Roto-Borola (pictured here) for over two years, we got him when he was maybe five months. A couple months back I discovered he really enjoys having his head massaged. He likes me to put a good bit more pressure on his head than I would expect him to be comfortable with.
He's still a very playful cat at times, and I try to engage with that as best I can but I don't always love being play-bitten. At some point a while back, if I'm petting his head and move my hand somewhere else near him, including petting his back or somewhere else on him, it sets off a timer of 15-20 seconds typically (usually around 10-15 seconds with no reaction, when he opens his mouth just a hint it means he is about five seconds away) for him to play bite me. If he's laying on top of me the timer it sets off is just for exiting the ride. I've been playing with him pretty rough by squeezing his head or giving him a little noogie, but it just hit me that this has really been him training me in how he wants to be pet.
So I'll give him a pretty rough noogie and he acts like "oh no, I'm really trying to bite you but I can't when your hand is right there", but he's definitely able to outspeed me. And I'm realizing now in retrospect, I started going for the back of his head because he left me one spot to find where he would pretend that he can't get to me. And he gradually trained me I needed to be more and more violent if I wanted to not get bitten.
So yeah, I put my entire hand around his skull and squeeze a bit tight and somehow he loves this. Realized a few months ago that this is his thing, realized today that this is something he taught me.
One of ours is kind of similar. We don’t put our hand all the way around her head but we definitely squish her ears down and pet her head really heavily and she loves it. If she’s really into it, you can start at her nose and pet her whole face, head, and neck, eyes and all. She’s very aggressively into it, lol.