Yes, but turn him over first.

You decide to turn him over, so he'll hopefully stop talking to you.

He doesn't protest, but he doesn't stop talking.

"I used to take pictures of Ben you know. I... ouch!" Greg says as you slap your dick against his ass. You slide your dick up and down his ass a few times before you finally settle down on him, and you stick the head of your cock in his cornhole. He clenches a little as you slide into his asshole, but he relaxes when its not as painful as he thought it would be. "I... oh god, yes. Fuck my ass. I can feel so much in me!"

You always knew Greg was a talker, but he won't shut up now... You wrap your arms around him and start dicking him deeper, and faster.

"Shit... fuck... " Greg moans. "I used to take pictures of him from outside at night, when he was changing.... I planted a hidden camera in the shower when he was 16... god that was great wacking material. Sonja eventually found it... but it seemed to turn her on as well. Both of us started spying on him all the time.... Oh GOD! Ahhh...."

Greg shuddered, and suddenly clenched his asshole. You weren't expecting the sudden spasm, and you suddenly orgasm in his asshole long before you wanted to. You realize that Greg must have came himself, as a whole mess of cum has been sprayed all over one side of the bed.

You slide out of Greg and contemplate what to do next...