Hooking up with old high school principal and his partner

You're all over 18? Everyone consents and take proper disease prevention precautions? Then what the hell - but if you come from a small town, prepare for it to miraculously turn into everyone's business.

It's the principal who really needs to question himself, not you. Sure you're all consenting adults now but it was his position of trust and responsibility for your welfare as a child that brought you together. I doubt his fantasies for you or other boys conveniently started the moment you left school; that he acts on his fantasies shows, for me, lack of self control and of integrity. He is taking advantage of his special access to young guys to get laid. I would stay away from him as he is taking advantage of you.