I knew what Mark was going to ask for next every time he would begin to reach down to grab my ass while I gave him head, so it wasn't a total surprise when he finally proposed it. I was in the middle of giving him a blowjob and he leaned to spank my ass, then run a finger around the edge of my asshole, sending a little shock up my spine. His cock was buried in my throat when he asked, "So you think you'd ever be up for letting me fuck your ass?"
I continued sucking him off for a little bit before pulling off of his cock long enough to ask, "You really want to fuck me?" I went back to sucking his dick before he could answer.
"Yeah, I do. I bet you're tight as hell and I think you'd probably love it," he replied. I grunted in reply and continued to give him head. He must have really gotten turned on by talking about fucking me, because he was soon erupting in my mouth and I swallowed every drop. I told him I would think about it.
Truth be told, I had fantasized before about what it would be like to try anal. I loved the idea of completely surrendering my body to another man, to let him use me for his pleasure. But I'd also heard stories about how badly it could hurt being fucked in the ass for the first time, so I was really hesitant to give in to the fantasy.
I decided the temptation was too much to resist and I told Mark the next day that he could fuck me on three conditions, namely that we do some research into the best position to use for my comfort, that we use a condom, and that he give me some time to get ready before we tried it. Mark agreed.
The next day, I paid a visit to a local sex shop and bought a buttplug to use on myself. My heart was racing when I got home, I was so eager to try it out. I undressed in my room and lubed up my new toy. It was a mid-sized to small, black, latex plug that I figured would be a good way to ease into having my ass entered. It didn't disappoint. I laid down on my back on my bed and began to try to ease the plug into my ass. I was so nervous at first, but I focused on breathing and trying to relax. Slowly, I could feel the plug begin to slide into my ass as I pushed on it. I went really slow, easing it in bit by bit, then suddenly it was all the way inside me. I laid there for a moment, feeling it inside me, then began to ease it out, then back in, getting used to allowing it slide in and out of my ass. And to my surprise, I was enjoying the way it felt.
I practiced with the buttplug for a few more days, then brought it with me to Mark's apartment one night to show him. It was a pretty typical evening for us, as we smoked a little weed, then I got undressed and began to give Mark head. After I'd gotten him good and hard, I looked up at him from my knees and said, "I have something I want to show you."
I went into his bathroom where I knew he had some lubricant and brought it and a towel back with me. I took the buttplug out of my bag and showed it to him as I began to lube it up. I spread the towel on the floor, laid down so he could see what I was doing, and began to insert the plug into my ass until it was all the way in.