Hello again, I hope you enjoyed my first story as I was really excited to share it. As I mentioned at the end of that story, once I learned give head really well with my friend Mark, I noticed he would sometimes reach down to fondle my ass as I was sucking him, even pushing a finger inside me sometimes. It always shot a thrill up my spine, but it made me really nervous, as I figured it may lead to him asking if he could fuck me. And I was right, because once night when I was going down on him at his apartment, as I was sucking both of his balls with his stiff cock resting on my face, Mark ran his hand over my hair and asked, “So, would you ever be up for letting me fuck you?”
Honestly, I had fantasized in the past about what it would be like to be fucked and had even tried out fingering my own ass, surprised that it felt kind of nice. But I’d also heard that it could really hurt. I gently released Mark’s balls from my mouth and looked up at him from my knees, my face turning a little red at his question. Fuck it, I thought. We’d already gone this far. “I would be willing to try it,” I replied, “if you agree to a few things.” My conditions were that I wanted some time to get ready for our first time and we needed to figure out a position to use that wouldn’t be likely to hurt for me. Mark readily agreed.
The very next day, I bought a small butt plug for myself, so that I could start getting used to having something in my ass. It wasn’t nearly as thick as Mark’s cock, but it helped me get used to relaxing my ass. We also spent some time online, researching positions for anal sex. About a week or so later, I told Mark I was ready let him take my anal virginity.
I went over to his place that night and we had a few beers to loosen up. Not long after, we retreated to his bedroom and stripped naked. I started out by going down on him, to make sure he was nice and hard for me. Then we spread a sheet on the floor and placed a pillow on top. He put a condom on and began to lube himself up and I also took some of the lube and worked it around my ass. “Ok, I’m ready,” I said as I settled down on the floor and laid back with the pillow under my lower back.
Mark knelt down between my legs and lifted them up to his shoulders. I closed my eyes and concentrated on relaxing as much as possible as I felt his fingers begin to feel between my ass checks and push into my sphincter. They were quickly replaced by the thick head of his cock and I took a deep breath. “Go slow,” I whispered, feeling the head of his cock push inside of me. There was a little bit of discomfort as he entered me, but it quickly passed as I kept my eyes closed and concentrated on my breathing.
“Ok if I go further in now?” Mark asked and I nodded. I felt a few more inches of his cock push into my ass, then he stopped to let me get used to it. It really wasn’t bad so far, as long as I focused on keeping my ass relaxed and just breathed. In a minute or two, he let me know he was going to push a little further into me and I nodded again. I don’t know how long all of that took, but before long, I heard him say that he was now all the way inside of me and that he was going to begin fucking me. Eyes still closed, I said ok and nodded again.
I felt his cock begin to slide out of me, then back in, going at a deliberate pace. As he pushed into me again and I felt him begin to fully press into my prostate, I felt my mind begin to swim. Aside from an actual orgasm, this was beginning to be the most intensely pleasurable thing I’d ever felt! “Holy shit, I think you’re really enjoying this,” I heard Mark say and I opened my eyes to look down. He was beginning to pick up his pace just a little bit and I saw what he was referring to. My own cock was throbbing hard from him fucking me and pushing into my prostate. I wanted to touch it, but I was afraid I might cum, the sensation was so intense.
“Just keep fucking me. Don’t stop fucking me,” I moaned to him, losing myself in how good this all felt. He picked the pace up yet again, as I kept moaning and telling him to keep fucking my ass, completely unable to control the things I was saying. That seemed to turn him on even more, because he really picked up the pace and started fucking me really deep and hard.
“Take it. Take my hard cock, you dirty slut,” he moaned to me and I moaned even more in pleasure as he took full control and pounded my ass. I didn’t want this feeling to stop, his cock felt so good as it pushed in and out of me. I don’t know how long we fucked, but soon he was slamming deep into me, his body stiffening as he groaned and I could tell he was cumming.
I was nearly out of breath as I felt his cock begin to soften in my ass, then felt him begin to pull out. I felt kind of empty as he pulled out of my ass, because I was insatiable in my desire to be fucked more. Mark went to the bathroom to get rid of the condom and as he did, I reached between my legs with one hand to finger my ass. With the other hand, I started to stroke my own engorged cock and almost immediately began to cum, I was so sensitive and turned on. I had a lot of cum stored up, I guess, because it came out in a massive jet and landed all over my stomach, chest, and face. Mark came out of the bathroom and saw me lying there, trying to catch my breath, covered in my own cum. I pushed the cum on my face into my mouth to swallow it and he laughed, saying, “I guess you really were into that. If I’d thought about it, I would have pulled out and cum in your mouth to give you two loads to swallow.”
I looked up at him and told him that we could try that the next time as I got up to go clean up the rest of my cum in the bathroom. I was already looking forward to letting him fuck me again and give me a good pounding.