Well, yes, it would be pretty far out there for Paul or his buddies to have access to a pillory. I mean, even if their sexual education through online porn included a lot of BDSM, there's still the problem of getting the actual pillory. If you can't make it yourself, which requires a lot of carpentry skill, then they're both hard to find and quite expensive for a handful of kids. Even semi-decent pillories cost around $500 USD, and a good one will probably be upwards of $1000. I'm guessing that Paul and his buddies wouldn't spend that kind of money on it, even if they could afford it by pooling their money. Most guys that age aren't going to choose a pillory over a PS5.
But going back to my suggestion that the scene should be of Lisa with some more dangerous people, such as Tony's gang, it wouldn't be at all unrealistic for a man with Tony's resources to buy something like that, or to have it custom made for him by an artisan. And it might be the sort of thing that he keeps in his basement for "questioning", or for "training", or for "correction".
Obviously, if you were to go that route, it would fall more into the category of forced content. But I've already gone on record as saying that I hope that we'll see more forced content, and even additional rape scenes, before the story reaches its end. But, since you've made that content optional in the past, it would probably have to be a scene which was part of Tony's storyline, but not an essential part of the story - something which could be skipped by those who don't want such things to happen to Lisa. That is, assuming that you were to continue to make such content optional, which seems like a good idea to me.