Jim and I met for the first of my weekly massages on Thursday of the following week. We had fucked for the first time on Sunday, but we hadn't talked or anything since then. I got a call from his office reminding me of my appointment on Thursday at 4:30. It was kind of a surprise but I wasn't complaining!
I was wondering if Jim was expecting me to wear panties, and what he would want from me when we met. But I finally decided that I would wear normal boxers, and that we could just let nature take its course. I was hoping that we would do something together, but I went in without any plans. First of all, I knew that some people would still be there at 4:30, so I assumed that we would have to be very discreet. Second, I didn't want to force him into doing something if he thought that it would endanger his regular life. So I would just go and get a massage, and then if anything happened, well, it would be fun.
When I arrived, the girl at the front desk was professional and everything was just like normal. Jim came out to greet me right at 4:30, and he said to the girl, "Taylor, you don't need to hang around. John and I are going to go out for a beer after his massage. We have become buddies." He laughed, she laughed, I laughed. She seemed grateful to get out early so she was out the door a couple of minutes later.
As I undressed, Jim went out and locked the doors. When he came back in, I was lying on the table on my stomach with a towel over my hips just like normal. As Jim closed the door, he said, "How's your back? Are you feeling better?" He went over and grabbed some oil, pouring it on his hands and rubbing them together.
"It's fine, for the most part. Just a little achy but nothing unusual." Jim started rubbing my lower back while standing to my side. I enjoyed the work he was doing. He really was a great masseur and had done wonders for me already. I felt my body melt into the table as got down to business.
Once he was done working on my lower back, he pulled the towel off of my hips and saw my boxers. He said, "Oh, I was wondering if you wore panties all of the time. It's nice to see that you wear normal clothes too!" He slapped my ass and said, "Roll over, stud. I want to see your cock!"
I rolled onto my back and my cock came out of the front of my boxers, standing there already hard and eager. Jim had this hungry look and, without saying anything, leaned down and took my cock into his mouth. I groaned from the sensations. This guy was a natural cocksucker.
After just a few seconds of him working on me, he let my cock go and stood back up. He said, "So, I've been thinking, John, about us. I have loved our times together so far, ok? You make me feel things I've never felt before. And I think we should be free to talk about what we like. So, what I want is, I want to try getting fucked. I've never even thought about it before, but I want to know what it feels like. I'm not sure if I can go through with it, but I really want to try. I want to share this with you. Is that ok?"
I was stunned. I never imagined fucking him. I guess I just assumed that he wouldn't want to do that, and I liked taking his cock in my ass. After a few seconds of stunned silence, Jim said, "Well, if you don't want to, that's fine. I don't want to put you in an awkward position."
I shook my head and said, "No, Jim, it's not that. I'm just surprised. I never thought about fucking you. Weird, I know, but it just didn't cross my mind. But I would love to fuck your tight ass, baby."
He helped me get up and then he started to undress. "I've been having this fantasy about getting fucked from behind while leaning over the table. We are both about the same size, so I think that would work. Are you willing to try it?"
He pulled down his boxer briefs and his cock was pointing straight out. He was obviously excited about this, and it all sounded good to me. I reached out and started stroking him. I said, "That sounds so hot. I hope you like it, but tell me if you need me to stop, ok?"
