My Freelance Work Ethic Gone Too Far?

So yeah, I'm a freelance web developer and work from home. Keeps things interesting. Had this one client, let's call him Tom, he’s in his twenties. Anyway, Tom was always late with payments, but also incredibly demanding. One day, we had a pretty good chat where I laid out my frustrations. I figured he'd either step up or go elsewhere. But instead of paying me what was due (which is not a small sum), Tom suggested we play daddy and little boy for our next meeting. I know it sounds weird, but he's always been so immature that the idea wasn't completely off base. Plus, as someone in their mid-thirties who’s never really had a father figure, it kind of hit home. Anyway, I agreed to meet him under these new conditions and we decided to use video chat. I came dressed all sharp, button-up shirt tucked in, pressed pants, trying to look like an authority but also comfortable with myself. Tom showed up looking like... well, like he just rolled out of bed. So disheveled and childish. We started off talking about work as always, then Tom got a bit playful. He asked me to call him 'buddy' or ‘boy’ for the session, which I did. Then he wanted some chores done, and surprisingly it worked well, there was accountability now that I had this added role. And yeah, we'd occasionally slip into more adult territory too, but with clear boundaries. By the end of our first play session, both Tom's work had improved and his attitude toward deadlines changed. But here’s the thing: after our little experiment, he started asking for these sessions way more often, even when there wasn’t actual work to discuss. I enjoy it too, feel like I’m making a difference in someone's life while still getting paid. Just worried it might be crossing some kind of professional line or being taken advantage of? What do you all think? Is this okay as long as everyone’s happy and consensual, or am I seriously jeopardizing my career with something so weird?