Hmmm. The first thing I ever had in my ass was a penis. It was not that horrible. I'm not saying it was great, but back then I don't think we ever thought about toys.

In my experience: It's much easier to enjoy when I am super turned on. Do what you can to mentally get yourself "in the zone" so to speak. Overall arousal helps so, so much.

Lube is essential. I didn't read all the posts, so I don't know if anyone addressed it yet, but especially on a virgin anus...well, you just DON'T want to go there without lube. Lots of lube. If he says no to that, I would personally question his motives. I get that it is a total dominance issue, and inflicting pain can be part of the fun, but there's pain, and then there's PAIN, you know? I guess if he doesn't want lube, you could ask to suck him prior, so that you can get it good & lubed with your mouth.

FWIW-from the post, he seems to be open, I mean he did say it wasn't a requirement. Sounds like he wants it to be good for you too, in the end (ha ha)