I like the graduated butt plug idea. I really don't mind what I do to his ass cause he has the most beautiful ass.
We got a couple for him to try and the smaller ones went great. BTW, huge shot afterward. HE LOVED IT. The medium one was uncomfortable for him.
kundalinikat: I took your advise and we're not using numbing gels.
We have tried him on top but still had problems. Allthough so far the toy play is going well so we're going to do that for a while. Besides, he's never been much for oral but likes sucking on me while I'm using the toys on him. ALL GOOD for me :D
Lot less discomfort afterward this time, granted I didn't penetrate him, just the toys. So that is a plus. It's been a week and he just sent me a text that he want's me to use the toys on him tonight in the sling so the week turnaround is a lot better. Thanks to everyone for their suggestions. I'll keep everyone posted. Hopefully get a pic or two with some of the butt plugs in. :D | 
