Get the lube...

There's really no reason to not use lube, is there? Sure, it would take effort to go get it, but it'd probably take even more effort to cram yourself in there dry. There's his saliva from the blowjob, but it's mostly dried up by now. Maybe you'd try if you were feeling particularly sadistic today, but fortunately for him, you're not. You sigh and hop off the couch.

"Just wait there, okay? I gotta get something."

Johnny's still waiting patiently on the couch with his ass in the air when you return.

"Good boy," you say, giving his nice rear a gentle pat before popping the lid on your lube tube, squeezing some out and smearing the cool gel on your cock, then around his sweet little hole.

He's definitely more relaxed now, even when you slip a finger inside to get the lube in deeper. Tight, sure, but surprisingly easy to move around in there. That's just a finger, though. Time to see if he can take something a bit bigger.

Once more, your tip is pressed against his asshole, threatening entry.

"You ready?" you ask.

"Mhm," is all he says, jaw clenched, bracing himself for your dick.