Over the next few weeks Mark and I got a lot more comfortable sexually. We would jack off together frequently, sometimes just ourselves, sometimes he would reach over and jack me off, and sometimes he would blow me. I didn’t complain, he was getting what he wanted and I was getting off. It was a win win.
One day, I was watching TV when he walked in and sat down next to me. I could tell that he was kind of nervous. He was fidgeting with the strings of his hoodie and refusing to meet my eye.
“Huh? Oh, I… It’s nothing.” he stammered, his face flushed.
“No, really, what’s going on?”
He sighed. “It’s just… I really like the dynamic we’ve had lately, y’know? And I want to ask something, but I’m afraid it will ruin things.”
“Go ahead, man.” I felt myself start to get hard. Was he about to ask what I thought he was?
“I’ve just been exploring some stuff, and I realized that there’s something I need to try.” He fumbled his hands as he talked, looking away from me.
He let out a deep breath and finally said, “I want you to fuck me.”
I felt my dick push against my jeans, already rock hard. A couple of weeks ago I would have been disgusted by the question. But now? I actually wanted to. No girl had ever let me do anal before. But even more than that, I had been wondering what it would be like to fuck Mark.
We started how we usually did, just jacking off together. Before long he was on his knees sucking me off. Then mark reached into his bag and pulled out a bottle of lube. He poured a good amount onto my dick and spread it around. Then he climbed up onto my lap. He positioned my head against his hole, and began to push down. After a bit of time, I felt myself slowly start to push inside him. His ass was warm and tight.
He lowered himself down slowly, occasionally stopping to get adjusted. I felt my head get all the way in with a pop, and it got a lot easier after that.
“Fuck,” he gasped, “you’re goddamn huge.”
Within a couple of minutes he finally managed to get all the way to the bottom. Then he began to slide back up, slowly riding me. As he adjusted, he began to go faster and harder, and before long he was moaning as he rode me. I had to keep my mind occupied to prevent myself from blowing my load too soon.
After a couple of minutes, I knew I was getting close. I grabbed his waist and began thrusting up as he came down. After a few more thrusts I grunted, slammed as far in as I could get, and unloaded deep inside him. At the same time, he blew his load, his hot sticky cum landing on my stomach.
After a minute of just breathing deeply, Mark pulled himself off of me and dropped back onto the couch. He bent over and licked his load off of my stomach, and then headed to his room to clean himself up. I went to the bathroom and cleaned myself up, still riding the high of what had just happened. When I got back to the living room, he was already there.
“So?” I asked. “How was it?”
He laughed. “I think I figured out what I needed to.”
Nothing else happened that night, but I had a feeling that this was the beginning of a whole new chapter in my life.