You can tell, we got to know one another very well!
One night, Joe was not getting an erection and he was most unhappy.
I asked if he had some lube and a pair of rubber gloves.
“Why?” he asked. “What are you going to do?"
"Just relax. I think maybe you'll enjoy it."
He went into the kitchen for the gloves and then collected lube from the bathroom. When he returned to the bedroom, I put on the gloves and instructed him to get down on his knees and bend over the side of the bed.
Thus, his rosy red ass was exposed to me in all it's glory. I applied a good amount of lube to my index finger and proceeded to rub it all around his anus. Once it was slippery all around his asshole and his butt crack, I gently inserted my finger. He moaned as I poked gently in and out.
"Does that hurt?"
"No, not really.”
I pulled my finger back out and applied more lube and spread some over my other fingers. I gently inserted my finger. But, this time, I pushed it in a little further and then pulled it back out repeatedly. After a few minutes of this, he was moaning.
"Are you okay?”
“Yes, I’m good,” Joe answered but he was breathing a little harder. And I got a big, "ahhhh," when I added a second well-lubed finger inside his asshole.
He didn't say, "Stop," so I continued to move both fingers slowly in and out, over and over again.