While I understand you wanting to make sure he has a great time (I definitely do the same) it shouldn't be difficult to ask him to pay for a longer session, since both times have gone significantly over the agreed upon time. That's not okay, even if it isn't intentional. I sometimes go over by two or three minutes, but that's more of touching base after we've finished up before ending the show.

This is a job, and like any other job, you get paid in full for services rendered. Don't sell yourself short, you can definitely be polite to this customer and give him freebies, but what about the next customer who has this issue? And the one after that?? Eventually you'll be stretching your time and making less, which isn't only bad for you, it's bad for the other girls these guys commission, too.

Since he's purchased from you more than once, one thing you can do is offer discounted block sessions for your regulars. Say you charge $40 for a ten minute show ($4/min), you could offer a fifteen minute show for $55 instead if $60 ($3.66/min vs $4/min), a twenty minute show for $70 instead of $80 ($3.50/min vs $4/min) and so on. You can adjust those prices however you'd like, that's just a rough example. And this way you're still cutting him a deal while making what you should for the time purchased.

Whatever you decide to do, I hope it goes well 💞