Now, now - no reason to be embarrassed. That's what we are here for!
Yes, but that's an extra $50.
No, yes, 7:46, only if you have chocolate croissants and Intelligentsia Colonia Llust'a Bolivia for breakfast.
Hmmm. Not sure exactly how you will sleep with the escort if you are in a separate room. Let us know how that works out.
Check with the hotel. If they have a no-smoking policy you probably can't burn the purifying sage. However, I find that pure sea salt satisfies the gods just as well. Oh, and have the flower maiden keep the chanting down. The people in the next room might want to sleep in.
8:26. Fondle faster, you have croissants to eat before he leaves.
Well, ask him.
Assuming you don't wake him from a sound sleep at 2:30 AM and shout "MAY I FONDLE YOU?," I don't see this as being awkward.
I think you should contact him by yourself and leave the insecurities at home. That'll teach the little fuckers for bothering you like that.
But seriously...
You really should ask the escort, as different escorts conduct overnights in different ways. One escort with whom I was a regular client told me that he would slip out discreetly at 6 AM on an overnight. (We didn't do the overnight) Another told me that he'd like to plan the overnight to occur when he had no prior plans or commitments the next day so we could hang out in bed 'til noon like he would with a boyfriend. (We did the overnight)
Regarding the other questions, may I suggest you frame the discussion in advance something like this:
"Hey, [escort name] I've never hired a guy for an overnight and, in fact, I have never slept with a man. I've always fantasized about spooning with another man, waking up in the middle of the night and fondling him, waking up in the morning and playing, and lingering over breakfast. Understanding that we all sleep in different ways, what are your thoughts?"
Regarding cleaning yourself out in the morning, it would seem like a mood-killer.
Whatever you decide to do, have fun! And tell the flower maiden I said "hi."