One of my young playmates, Jacksin, has an expression he loves:
“With enough lube anything is possible”
I’d probably change it to:
“With enough lube, and enough patience, anything is possible”
Of course, that reflects our respective personalities. If he’s playing Dom and you’re a twink then expect him just to ram that massive dildo up your ass and enjoy your screams. He’s definitely got a little touch of the sadist in him. I prefer to push you as far as I can without you screaming – it might hurt but you’ll be so horny you will want me to continue. 😉