You fuck him

"We need some lube - it's in the drawer if you'll let me grab it," I said pointing to the nightstand, "There are condoms too if you want to grab those."

Leo leaned down and gave me a tongue probing kiss before moving to reach for the night stand.

"Lube, yes. Condom, no way. I want to feel every inch of your glorious cock. I'm safe and I think you're safe so let's just go at it bare."

The smile on his face melted me into a puddle of compliance. I'd pretty much do whatever he wanted. He applied a generous amount of lube on his hole and my cock, making sure to work in the lube from head to base.

"Might be best if you slid down on me. I don't want to hurt you," you tell him as you remembered your past experiences.

Leo moved back to straddle me, leaned in, and gave me the most tender kiss before rubbing my cock against his hole. I could feel his ass muscles and hole tightening and releasing as he played with me, forcibly poking the head of my cock against his hole. After a few tries, I felt the head slide in, only to slip out again just as quickly. Leo kept working it and I was in again, this time deeper than before. It was so hot, and so tight - better than I ever imagined. He kept moving slowly, taking a little more of me each time. I was so lost in the sensation I didn't realize he'd managed to take all of me in him, until he started sliding up and down of my cock. The look on his face was pure bliss and he was moaning with each thrust.

I was still really afraid of hurting him so I let him do all the moving but was starting to think I would not last very long at this rate. The sensations were just too much, not to mention the view of that tanned gorgeous body sliding up and down on my cock.

"Troy, you feel so good inside me. So big, filling me up. I think we can change positions now." Leo said as he slid off me and laid back on the bed pulling his knees up to his chest. "Come on Troy, you want to fuck me don't you?"