"Do you want to tonight?" asked Matt.
"Sure," said Dan. "How do we, uh, start? Do you want to kiss or...?"
"God No!" exclaimed Matt. They both started laughing.
"How about this", asked Matt, " how about I go into my room, throw on a hoodie so it hides my body, and get ready? You go in your room and get yourself ready, and when I call you in, you just... do your thing?"
"Sounds good to me."
Matt walked into his room and threw on his hoodie. He grabbed his lube and dildo and started prepping his ass for the night to come. He made sure he was well-lubed and was loose enough for whatever Dan might be packing. He had never seen Dan's junk hard before, he had the odd glance of him coming out of the shower, but nothing to make any assertions off of. He was well used to his dildo now, as the lockdown had been so long and he got bored fast. He used up the last of his lube, covering his hole and dildo with as much as possible. The cold touch of it was always jarring at first, and he suddenly realized that Dan's cock would be prewarmed by the blood flowing through it. His own dick began to grow at the thought of it. That alarmed Matt.
He was starting to have second thoughts, maybe he shouldn't do this, he wasn't gay and this was pretty fucked up. But the anticipation and added drunken vigor overtook his caution, and he eventually called out "Ready."
Dan was sitting on his desk chair. He had started looking up porn to get himself ready, but before it even loaded onto his screen, he was already hard. The anticipation of finally getting to shove it into someone after all the months of lockdown was a stimulant all of its own. He decided to watch the porn anyway, it made him feel more normal and what else was he gonna do for the next few minutes. He heard Matt call "Ready.", and his heart began to race.
Dan was incredibly nervous. Like his first time with a girl, he was overthinking it. He decided to down the rest of his drink, giving himself a jolt of courage. He stood up, his pants falling to the floor. He walked to Matt's room bottomless and saw Matt bent over his bed. With his hoodie on, it wasn't so obvious that he was a dude, but Dan was probably going to just close his eyes the whole time anyway.
Matt was incredibly nervous. He had never done anything like this before. He had considered asking one of his past girlfriends to peg him after he heard Tony's story, but could never bring himself to do it. But now, he was bent over his bed waiting for his best friend to stick his cock up his ass. He suddenly had a very sober moment of realization of what was about to happen and wanted to back out immediately.
Then, Dan's cock touched the ring of his hole, and a shiver went up Matt's entire body. It then retreated, and came back with twice the force, and started to enter Matt's ass. It was incredible, the warmth was one thing, but feeling the blood pulsing was invigorating, he could tell Dan was rock hard. He felt his cock slide in further, millimeter by millimeter, going at a snail's pace, until finally, the entire head popped in.
This wasn't the first time Dan had fucked someone in the ass. Many of the girls he had been with were down for it since Anya, as he had plenty of experience by now. He decided that if he was going to pretend Matt was a girl, he might as well try and please him like he would a girl. He knew how to fuck, and if I was going to do a thing, he was gonna do it right.
Matt felt Dan's cock slowly slide further in, still going very slow, until he finally felt his friend's pelvis hit his cheeks. He had bottomed out. Dan's cock was much bigger than Matt's dildo and was just what he needed. The extra stretch felt fantastic, especially with the extra give skin has compared to the plastic of his dildo. Matt could feel every vein, every contour, every curve of Dan's cock. He could probably have drawn a photorealistic drawing from the sensation alone.
Then Dan's cock began to back out, and Matt's ass immediately missed it. He backed all the way out until the head popped out and only the very tip was still in, he then began to push in again. Matt couldn't believe this was happening, he was actually being fucked, and by his best friend of all people, and he was loving every second of it. Had anyone asked him before that night the probability of all those three things happening at once, he would have said 0%. But right now he was in complete ecstasy. Dan was starting to form a rhythm now, picking up the pace slowly and sliding all the way in and all the way out, yet never fully removing his cock from Matt's ass, always leaving a bit of the tip in.
The pace started increasing, second by second, until the two were going at it like frantic rabbits. Dan slowly ramped it up until he was fucking as fast and as hard as he could. Matt was in a fit of pleasure, unable to move but the spasms he had from ecstasy. His body was pressed up against the bed, and while his hands weren't touching it, his cock rubbed up against the bed fabric with every thrust. He was rock hard, and the minor stimulation was enough to get him ready to explode. He wasn't quite there though, he was practically edging himself near to the limit of cumming while Dan fucked his ass. He was trying to hold it back as he knew from past experience with his dildo that anal wouldn't feel as good with post-nut clarity, and he wanted to wait for Dan to finish first.
Dan was also about to lose it. The pure eroticism of this whole experience was giving him a throbbing erection and it took everything he had not to nut in his friend's hole already. They had only been at it for a couple of minutes and he didn't want to blow his load early like a loser, he thought he should last, at least, last 5 minutes for his own self-respect. The two of them had always joked about men who couldn't last long, how they were losers and wimps, and he didn't want to be known as one of them, even if to only Matt. He kept a steady rhythm, not going too fast, partially for the comfort of his friend, partially to keep from cumming. It wasn't working though, he was about to blow. He sunk his cock all the way in and stopped, he was so close to cumming but managed to hold it together. They stayed that way for a few seconds, Dan's cock buried in Matt's ass, neither moving.
Matt didn't know what to do, he was so close to the edge he was about to pop, and there was nothing he could do about it. Just a few more thrusts from Dan would fuck him into an orgasm. He had tried lifting his hip off the bed enough that he wasn't rubbing on it anymore, but it wasn't working. He was about to cum from the sheer pleasure of getting fucked in the ass. But at the last second, Dan stopped. He was buried in his ass, hips pressing against his cheeks, his balls grazing his gooch. He thanked God for the respite. While it still felt amazing with a cock shoved all the way in his ass, he was able to come back from the precipice of ejaculation. They stayed like that for a while, both breathing heavily, but barely moving any other muscles. After calming down a bit, Matt asked "Is everything alright?"
"Yeah," said Dan, not wanting to admit his friend had almost made him cum in under 3 minutes, "just got a leg cramp," he said, making something up on the spot. "Everything ok with you?" he asked.
Matt didn't know how to respond to that question. This whole experience was starting to make him question his sexuality and his relationship with his best friend. With so many thoughts running through his mind, he summed them all up by giving a simple thumbs up.
Dan took that as a sign he wanted to continue. He had calmed down enough that he would bust, and began to withdraw his dick.
The sensation of withdrawal provoked an instant longing in Matt, after being stuffed full for a while, he missed it as soon as it departed. Dan was moving very slowly still, taking a couple of seconds to pull out his cock all the way to the tip before he began to thrust it back in. Matt was loving every inch of it as it came back into him, the sensation gave him a warm tingling feeling that moved all the way up his spine to rest in a pool of pleasure filling up in his mind. His cock twitched constantly as he was being penetrated, begging for attention that Matt was too scared to give it.
Dan was starting to lose himself at that moment. He stopped caring about lasting long, stopped thinking at all for the most part, and was living in the moment, enjoying the tight hole wrapped around his cock. He was fucking Matt with gay abandon, now, slowly at first, but speeding up to a steady rhythm as his cock pulsed with arousal. He kept thrusting in and out as his cock stiffened to a rock-hard level he had never experienced before. He couldn't stop anymore, he had committed to this and there was an avalanche of pleasure he couldn't control anymore. Cum started to rush up his dick, and on instinct, Dan pulled out. His cock erupted with cum, showering the back of his friend with thick droplets and landed on his ass, and drenched his hoodie. He felt like he was in a haze, ropes of cum continued to flow out of his cock for several seconds. Finally, Dan regained control of himself. He looked around at his friend who was lying face down on the bed, covered in his come from his ass to the top of his hoodie. He noticed some of his cum had actually shot all the way across the room and splattered against the other wall. He was briefly impressed with himself until he noticed the time, he hadn't even lasted 4 minutes...
Matt was in trouble. Dan had picked up the pace and began to fuck him harder and faster. His attempts to delay his orgasm were being superseded by his wanting to stop himself from moaning out loud. He was about to cum whether he liked it or not, the constant cock thrusting into him was going to force it out of him. His body finally succumbed as his balls tightened and a thick load started to rush through his cock. He was still pressed up against the bed, so instead of shooting across the room, it pooled up around him, soaking into the sheets. His whole body trembled with pleasure as he orgasmed. His cock was pressed into the clamshell of cum on his bed. Dan got a couple more thrusts in before he suddenly pulled out. Matt felt a thick stream of cum hit him, covering his ass and soaking into his hoodie. He even felt cum shots hit the back of his head, and could smell them as they soaked through the fabric.
"Sorry about that," Dan said, panting. "I guess it's just been a while, I got a lot stored up." It was a lie. Dan had jacked off this morning, his tank wasn't exactly full, but he didn't want to admit that he had just had the best sex of his life.
"No worries," Matt replied. He didn't want to get up and reveal the clamshell he had made in the bed.
"I'm sure I'll do better next time," he said without thinking. Then he paused, realizing what he just said. They had never agreed to do this more than once, he had just assumed without thinking about the implications. First, there was his sexuality. Dan had always considered himself straight, but a man had just given him the best orgasm of his life, which was somehow the least of his concerns. Because, on top of that, the man who did so was his best friend and roommate, someone he would never have considered dating or being in any kind of romantic relationship with, but what else would you call two best friends that lived together and had regular sex? And lastly, he knew he had to do it again. He couldn't give up such a good feeling as he had just experienced.
Matt had the same thoughts running through his mind. Could he still be straight if he liked getting fucked up the ass? One time was one thing, but if they continued to do it, would that make Dan his boyfriend? The thought was uncomfortable to him, but he also desperately wanted to do it again. He knew that from now on, a dildo would always be inadequate to what he had just experienced. The awkward silence stretched for a few moments. Matt finally made up his mind and said "I suppose I can give you another chance to redeem yourself" he said with a chuckle. It was a compromise, one more time ought to do it for him, then he would be good. He still didn't move, just lying on his bed, breathing heavily and covering his cumstained sheets with his body.
Dan laughed too between his own heavy breaths and gave Matt a playful smack on the ass. He still hadn't moved from his position on the bed. He walked out of the room and towards the bathroom for a shower. His body was covered in sweat giving his smooth skin a glow. He climbed into the shower and began to wash up, as his hand made its way down to his cock. Blood started to flow back into it with the slightest touch, and he began to fondle it. At first, he was pretending to just be cleaning it, but before he knew it, he was straight up jacking off, thinking about what just happened and what was going to happen again. His dick was standing straight up now, and he was furiously rubbing it in the soapy water, remembering the tight feeling he just felt inside his roommate's hole. Before too long, the pressure climaxed again, and he came, not as powerful as before, but still enough for it to shoot ropes of cum everywhere, onto the floor, onto the shower walls, and even hitting Dan in the face. He never had explosive cumshots like this before, and was still getting used to it. After calming down again, he began to clean himself off for a second time.
Even though Dan had left the room a few minutes ago, Matt still hadn't moved. He laid there, sandwiched between two cum shots, Matts on his back and his own pooled around his crotch. He loved the scent of it. Dan's cum had soaked into his hoodie, from the bottom to the hood, clinging to his back, hair and even a little next to his face. When he eventually did get up, he balled up his sheets and threw them in the hamper to wash, but not the hoodie. He wanted to keep the scent for a while longer. He eventually heard the shower turn off and the bathroom door open. He waited a few seconds and went out to have his own shower, walking into the hall naked. He ran into Matt, and even though they just had sex, they awkwardly tried to hide their nakedness from each other as they passed by. As he got into the shower himself he noticed a bit of cum on the near the top of the glass door, Dan must have just jerked off in the shower. He began to wash himself, but couldn't help but play with his own ass as he did. He found himself continually looking up at the cum still on the top of the door out of the shower's reach. His impulsive thoughts got the better of him, he just had to try it. He licked up the cum off the glass door, tasting the sweet smell he had been obsessed with. It was salty, with some sweetness to it. Matt had tried eating his own cum before, but in his erotic state it was a completely different experience. He loved the taste of Dan's leftover cum, and could only think about how he wanted more. He played with his ass with one hand, and began to jerk off with the other. Considering he had just had a hands-free orgasm earlier, he was able to jerk himself off in under a minute, cumming again while his fingers explored his butt. The jizz had gotten all over his hand, and he instinctively licked it up. It wasn't as good as Dan's, not as potent. Just another sensation he wouldn't be able to replicate on his own he figured.
