[F]irst ti[m]e pegging. | 2016

After much discussion about it, and after being instructed to purchase my own dick, I got to fuck him. About four or five days ago, he first let me play with his ass. I've posted that story already, but for those who didn't read it, I'll recap. He was tentative at first, but I had him guide me to his prostate, and as soon as I hit it, he was in complete ecstasy. I loved knowing I made him feel that way, and I wanted more. I didn't know until a couple days later how much he wanted more, too. He couldn't wait for me to fuck him.

Our first try went perfect. We were playing around as usual, and I started easy by fingering his ass and rubbing his prostate while stroking his long, hard cock. He was gasping for air, and almost couldn't control himself enough to tell me to stop before he came. I slowed down, and he started begging for more. "I want to more, baby. I want you to fuck me. Pound my tight, little ass."

I was more than happy to oblige. I had been waiting for this, fantasizing about it for so long. I got myself into my new toy, and poised myself above him. I told him to beg more. "Please, baby. Please fuck me with your cock," he whimpered. I properly lubed my toy, and put more on his now relaxed hole. I rubbed the tip over the outside, and got a visible excited response. He was more than ready, and I was too.

I pushed myself into him, and when I had the first inch or two in, I stopped so he could relax and just concentrate on me jerking him. This was my first time doing this and I didn't want to hurt him and ruin it for both of us. I hadn't stopped for a full minute before he was pulling on me, asking for more. I let him control my pace, which he did by pulling on my thighs. "Start moving more," he instructed. I did so, and after a couple thrusts I was actually fucking him while I stroked his cock. It was so exciting, I had a hard time keeping myself from just going at it.

He adjusted to the slow pace, and wanted more still. "Harder, baby. Faster," he kept moaning. Before long, I was pounding him like I so desperately desired, and he was loving it just as much. I could feel his cock start to twitch in my hand, and I knew he wasn't going to last much longer. "Baby, I'm going to cum," he gasped. "Mmmm, you're going to cum from me fucking your ass, what a dirty little boy," I teased.

I started stroking faster, and it pushed him over the edge. He came hard, and unleashed a rather large load into my hand. He laid there gasping for breath, and I gently pulled out, leaned over, and kissed him. I was soaking wet, and I knew this was something I wanted to keep doing. From the look on his face he did too, and I don't mind at all. ;)