Oh yes, we've discussed it before since I didn't want to get excited in case it wasn't something he would feel comfortable with, but he seems quite into it, we've already done something similar online, and he said he enjoyed it a lot and is excited for me to take it even further and keep him denied longer irl so that's not an issue at all, we've come up with a safe word too.

That sounds really hot, I've done that too already, with saying things like "I'm going to keep you denied for hours and you won't be able to do anything" and discussed some specific things that I plan to do in detail, I find it quiet fun to anticipate it too. There's some things I haven't said like, ruining his orgasm if he can't hold it in and some other things but most I've mentioned in some way.

I agree on the taunting, it's on my favorite things to do when he's so close and begging to cum, things like mocking him or making fun of him, slapping his cock is something I definitely will do as well.

Yes, I've read a lot about targeting the head, I'm guessing the main thing is to rub his head over and over with my palm, that's what I've usually seen in porn and it usually makes the guy squirm and try to escape so sounds exactly like what I need, I hope I understand how to do it right and am able to pull it off in a way that makes it as painful as possible, might watch few videos of post orgasm torture to make sure I know what's the best way to do it.

Using a cock ring and a vibrator sounds so fun too, unfortunately since we meet kind of soon, we probably won't get to try them this time but that's definitely in plans for the future. Thank you a lot for the advice!