If you think he might like role-playing (and a lot of people do), any idea what sorts of things he likes. There are endless scenarios:

Sultan and the new harem girl - with her hands bound so she doesn't cause any trouble.

The leather-clad succubus (female demon) who sucks the life out of helpless men, leaving a withered exhausted corpse.

The bad school girl who acted up in class, and needs to be properly punished.

Captive of the amazon princess.

Whatever.

Have an ilicit affair - with him - at a nearby sleazy hotel.

Physically - is there anything he has hinted he would like that you haven't tried yet?