Oh... that's an interesting idea... I mean, if you're sure you want to try it and think I can handle it... we could always give it a shot, as long as we go slow at first and make sure everything feels good for both of us. What do you think?

Alright... just take it slow and let me guide you. I want this to be enjoyable for both of us, okay? Start by rubbing against me with the head; see how that feels. And when you're ready, push in slowly; don't force anything if it hurts or doesn't feel right.