TL;DR: How does your sexy time usually go when you are planning to do some pegging?

So my so and I have recently discussed pegging. This has been a fantasy of mine for quite some time and I was actually fine with it being just that, but recently the topic made it's way into a conversation and that went surprisingly well. Now my brain is trying to wrap my head around taking that step. We've played with my ass a few times before. It's really just the actual plan of a pegging session that has my mind going wild.

How does your sexy time usually go when you are planning to do some pegging?