Post-Vegas adventures with my friend [M/M] | 2016

This story is somewhat of a continuation of this one. However, it is not super necessary to read that one to enjoy this story.

After our Vegas trip, Brandon and I had spent the next couple of week getting together a few times and reliving the moment. He would either come to my place, or I'd go to his place, we'd watch some porn together, strip to our underwear, and get freaky. Mostly just exchanging hand jobs and blow jobs. It was the nature of sneaking around constantly that made it exciting.

In between our meet-ups we would text each other constantly. At first they were seemingly innocent, or "in code". Things like "Want to hang out? ;-)" or "Let's do something". These I could easily explain as being just friendly texts trying to set up plans. But as the weeks went on, the texts got dirtier and dirtier. We got bolder with our texts by saying things like "I want to drop a load down your throat".

Through these texts, we learned about our sexual pasts. Turns out I wasn't the first guy he had been with. He fooled around with a neighbor when we was in the high school. They would meet up after school and during summers and do the same things we had been doing: watch porn, jerk each other, and suck each other off. He said it lasted a couple of years before the neighbor got a long-term girlfriend.

It was also through these texts that I admitted that I had been with two guy friends in high school. The first was a friend who lived down the street when I was a freshman in high school. My situation was similar to his, though my relationship only lasted one summer. The other friend was during my senior year. We would drive to a dark, empty street in our town and suck each other off in one of our cars. When possible, we would do this at one of our houses if we happened to have it all to ourselves. It was during one of these times that I was fucked in the ass for the first time.

That last tidbit piqued Brandon's interest. A stream of questions soon followed. How did it feel? How big was he? Did you use lube? Did he cum? Where did he cum? I tried my best to keep up with his questions. Then he asked the question I knew he was dying to ask: would you do it again? My response: absolutely!

Thus begin our planning of when he would get to fuck me. As it turned out, the following weekend was Easter weekend, and my roommate was headed home to spend time with family. This meant that Brandon and I had all day Saturday to ourselves at my place. It was the perfect scenario.

As the day approached, I got a bit anxious. While I had been fucked once before, it had been years ago. I was worried I would be able to take Brandon's 8.5" cock. I certainly had done with solo anal play in the past with fingers, empty bottles, and even a cucumber once. But to have a real thing inside me again... I just shuddered at the idea, and grew hard any time I thought about it.

Finally the day arrived. Brandon came over with a 18-pack of cheap beer. He was dressed in a nice button up shirt and jeans. He also smelled incredible. He obviously felt this had to be a bit of a special time. There was a baseball game on, so we sat and watched that for a bit. Eventually we grew bored of it and decided to play a little game: strip poker.

Texas Hold 'Em was in its twilight of popularity at that point, but we still played occasionally with friends, but not the "strip" variety. We set out the ground rules and began playing. I don't remember the specific hands, but soon enough we were both completely naked. The bets then turned to sexual actions. Hand jobs. Blow jobs. Ball-sucking. Nipple licking. Then Brandon threw down a monster bet: rim job. The loser of the hand had to lick the others asshole. This was completely new to me, so I was excited to try regardless if I was giving or receiving.

I ended up winning the hand. He told me to get on all four on the couch. I complied and stuck my bare ass high in the air. He came up behind me as I waited in anticipation. I felt his hot breath on my asshole a second before his tongue dove into it. At first his tongue ran along my ass crack a few times soaking it in his spit. Then he began pushing his tongue into my asshole. The whole time he was moaning as if it was the most delicious thing he had ever tasted. This turned me on so much that I started moaning back.

With his tongue still buried deep in my ass, his hand reached between my legs and gripped ahold of my rock hard cock. His swiped his hand across the tip and used the vast amounts of precum leaking from it to stroke my dick as he continued to rim my hole. He pulled his face back from my ass. I thought we were going to play another hand when I felt something more rigid press against my ass. Looking back, I saw Brandon pushing a finger into me as he continued to stroke my cock.

As his digit pushed into me, I met his penetration by pushing my ass back on the finger, taking it deep inside me. Brandon fucked me with his finger for a bit before introducing a second finger to my ass. The thrill of his fingers filling my hole made me want his more and more. Finally I just shouted "Shove your dick inside me!"

He ran to his jeans to pull out the lube. He came back over and rubbed the lube all over his cock, then into my ass. He pushed me so I was laying over the arm of the couch with my cock pressed against the fabric of the couch. He lined up his cock with my hole and began pushing it into me. With me a bit more loosened up, I took him a bit easier than I thought. He was kind in the sense that he went slowly, but I could tell he just wanted to ram it in.

The feelings that were coming over me as he pushed deeper into me were an odd combination. I felt slight discomfort from having what was certainly the large object in my ass. However, I was also extremely turned on by the idea of his cock stretching my hole further than it had ever been. Overall, I was loving it.

Finally his cock was fully inside of me, and Brandon began pumping it in and out of me slowly. With each pump I relaxed a bit more. He was clearly enjoying it as he kept saying things like "Your ass feels so good" and "You like my big cock inside you?" Most of time I could only reply with a moan or a meager "uh-huh". I was pretty much in ecstasy.

The entire he is fucking my ass, my cock was pressed against the couch arm making it impossible to reach, and I was aching to stroke my cock. I asked Brandon to switch positions. I wanted to be on my back. We moved to the ground where I raised my legs high in the air to give him access to my ass again. He lubed up again for safe measure and plunged his cock back into my ass. There was no need for him to ease it in as it slipped in extremely easily. He had clearly stretched my asshole quite a bit. It made me feel so slutty, which turned me on even more.

He pistoned in and out of me faster and faster. Each pump set me closer and closer to the edge of cumming. I was actively avoiding stroking my cock because I knew that one touch would set me off. Instead, I played with my balls or reached further down to feel Brandon's cock slide in and out of my ass. I couldn't believe that something so thick was fucking me with such ease.

Eventually I gave in and gripped my hand around my cock. Just two strokes sent me into a powerful orgasm. As Brandon continued to fuck me, my cock shot the first load onto my chest. The next few landed on my stomach with the last couple of loads dribbling out next to my cock.

The sight of me cumming must have turned on Brandon because he began pumping harder and faster. Within a few seconds his cock stiffened and he grunted "I'm gonna cum". I told him to fill my ass with his jizz. He gave one last thrust and released deep in my ass. It was the first time someone came inside me. The feeling was unreal.

He collapsed on top of me, and we just laid there for a moment. He pulled out of me and could feel his cum leaking from my ass. We headed for the shower to cool off and clean up.

Our relationship continued pretty consistently for the next few months with me always bottoming. It would take a random encounter with a stranger for me to finally top, but that is for another story.