Dirks

I think you hit it on the head right here. I recently did an overnight with an escort I hadn't met before. While not a total bomb, I do think I would've enjoyed a shorter session with this particular guy. 
But I have had some absolutely wonderful overnight sessions with guys that I have a lot more rapport with, both sexually and emotionally/intellectually.
I do not think I will ever do an overnight with an escort I have not met before. And that might be good advice for you too. 

When I've had overnight hires, it has been a mix of activity.  Usually, it involves meeting and having some bedroom play before going to dinner, then returning back for another round of play time.  That can include sharing a bottle of wine in the bath.  By the time I'm ready to sleep, there may be some cuddling as we unwind.  It's about 50/50 whether or not there is any intimacy in the morning.  
Another overnight scenario I enjoy includes going to dinner and a show - whether a play or musical, a concert, or a bar with live entertainment.   Just something that I would enjoy, but usually prefer to not attend solo.

Strangely On!

Turn On OR Off ?

I love watching two men dance tango, whether it's erotic or just a couple of bros (like the old days).  Here's a couple of gents dancing tango on the sidewalk.  Note the lifts, where the shorter one looks utterly weightless.