Yes, but move up to 2 fingers

You slip in another finger, but its going to be difficult going again. Greg gasps in a bit of pain when you do, but he soon relaxes, and you are able to slip your fingers in a bit further.

"Oh god, oh god. I wish I would have just tried, you know? I walked in on him in the shower a few times, you know. I saw his little dick hanging there, and I just wanted to swallow the whole thing up. It wasn't a mistake either. I used to hang out around the shower, and open the door right as I heard him coming out. He just stood and looked at me... I wasn't thinking on what I was doing..."

You shove both fingers fully into his ass, and you hear him grunt in pain a bit. You don't say anything to him. You just keep fingering him.

"Another time, I pulled down his towel after he showered, and took it from him. Sonja caught me that time, and gave me an odd look. I fucked her hard that night, so she forgot all about it. The next day, Ben walked in on me showering, and I yelled at him. I was quite shocked, thinking it was only me spying on him. He never walked in on me after that, and he started locking the shower door."

Your dick is quite hard from listening to Greg talk, and you figure that he's only going to keep talking, regardless of what you do, so you spit on your dick and slid up to his asshole.

"Yes...." he whispers. "Stick your cock in me and show me what I have been missing all these years."