Re-Encountering His First

Late on a Thursday night, Jack heard his phone vibrate on to the bedside table. He had barely noticed the sound over the soft trickle of rain on his apartment window, a constant tempo in his Seattle building. As he picked up the phone, the screen illuminating the room, he was thrilled to see the sender: His old friend, Ryan.

Jack was 5 years younger than Ryan. They had met when they were both kids, Ryan being the classmate of Jack's older brother. But as they all grew up, it was clear that Jack and Ryan were the closest. Despite the age gap, they had the same taste in music, rooted for the same sports teams, and enjoyed the same hobbies.

Jack and Ryan hadn't seen each other in nearly 7 years, since Jack was 18 and Ryan was 23. That summer, Jack had graduated from high school and Ryan was starting his first job post-college, and they spent nearly every evening together. With the sun staying out late and the weather dry, they would bike outside together, drink some beers in the park, and chat about life.

One evening stood out in Jack's memory. Well past dark and after a few too many beers at the park, the conversation naturally steered toward sex. While talking about the various women in their lives, Jack mentioned to Ryan that he had always been attracted to men - maybe even more than women. Ryan responded that, he too, had been a little curious about guys, noticing himself staring at men in the locker room or being intrigued by their physique while watching porn. One thing led to another and soon they had their pants down, jacking themselves off side-by-side. The thrill of being outdoors added to the experience as they both knew they could be caught at any moment. But the biggest thrill of all came when Ryan reached over and grabbed Jack's dick, stroking it furiously as Jack moaned in pleasure, never having had a sexual experience with a man before. In seconds, he shot his load over his shirt, stomach, and Ryan's hand, who licked off his buddy's cum. Just after, Jack masturbated Ryan to the same conclusion.

Sadly, the night was never talked about much again. Turns out, it was less to do with the awkwardness of exploring their sexualities together but more because soon after, Ryan got notice that he would have to move to Los Angeles for his job. As the summer came to an end, Ryan quickly packed up his life in Seattle and moved down the coast, just as Jack went away to college and became busy with his own life.

So when Jack saw Ryan's text come through his phone, he was excited to hear from his friend but almost nervous about the reason. Why would Ryan be texting him so late?

Ryan: Hey Jack, it's Ryan. I know it's last minute, but my girlfriend Sarah and I have a hotel up in Seattle for tomorrow night. Any chance you want to grab dinner and catch up?

Jack: Hey Ryan, great to hear from you. Sure, that would be fantastic. Let's do Ivar's at 8pm.

Ryan: Great, see you there man.

-

The next evening, Jack got ready in his apartment. He realized that he was actually a little nervous to see Ryan again. It had been so long, and admittedly Jack was still feeling a bit turned on by Ryan. He had been his first sexual experience with a man, after all. He put on his favorite evening outfit, a well-fitting pair of dark jeans and a tailored shirt. At 25, he was easily in the best shape of his life. He admired in the mirror how his outfit clung closely to his body, accentuating his muscular physique and rounded ass. His trimmed, black chest hair peaked out from his collar and a soft five o'clock shadow made his jawline appear stronger. He looked like a stereotypical jock.

When he arrived at the restaurant, he quickly spotted Ryan and Sarah already seated. He popped over, eager to check out his old friend.

"Hey Ryan!"

"Hey Jack, great to see you!" Ryan stood up to greet his buddy. "This is my girlfriend, Sarah."

Sarah reached out to shake Jack's hand, and they began to introduce themselves in more detail. She was extremely nice and beautiful, but Jack couldn't keep from staring at Ryan. Jack had forgotten how imposing Ryan was, standing at 6'2'' with big, blue eyes and wavy blonde hair. He wasn't necessarily chiseled, but certainly strong and husky, like a fit college football player. And of course, his smile was charming as ever, a wide grin that lit up the room.

They ordered drinks and food as they slowly caught up on what each had missed since last hanging out. Ryan had moved his way up the corporate ladder down in LA, now working as a lawyer and making loads of money. Jack shared how he had just graduated from college and started work as a consultant, which frequently brought him on trips around the country. They discussed how Ryan and Sarah met, and joked about Jack's various conquests, openly noting both the men and women in the mix. Ryan seemed extremely cool about that development.

After a few hours, they were all pretty tipsy.

"If you two boys don't mind, I think I'm going to call it a night," said Sarah with a yawn. "I'm pretty tired after the long drive up here."

"No worries babe," replied Ryan. "Mind if I call you a ride back to the hotel though? I'd love to hang out a bit more with Jack."

"Yeah of course. I figured you two had a lot to talk about," she replied with a smile. After the standard goodbyes with Jack, she headed out of the restaurant.

Immediately, Ryan looked over to Jack with a devilish look on his face.

"Okay man, let's party." Ryan seemed amped for a crazy night out. "Let's go to a bar around here."

They quickly paid the bill and left for a dive nearby, grabbing a semi-private booth near the bar and ordering a pitcher of a local IPA.

"Sarah seems cool, Ryan." Jack meant it. She was extraordinarily nice, even though she had been getting in the way of them revisiting the past.

"Thanks, Jack. She's just really open about everything. A lot of people I've dated would have made me go back to hotel with them. But she just wants us both to be happy, you know?"

"Yeah man, that's great," Jack replied. "And of course, she's pretty hot." Jack smiled as he said it, knowing this would remind Ryan of their past chats.

"Ha, just like old times. You're right though, and she's fucking great in bed."

They both laughed, realizing how quickly they had reverted to their old dynamic.

"So, tell me about being with guys," Ryan asked Jack with a slight smirk. "What are you, the top or the bottom?"

Jack thought the question was hilarious. He knew that Ryan was both busting his balls and being serious. They were close enough to talk about these things, he figured.

"Well, kinda both I guess. But usually, I'm the bottom with the guys I hook up with. Most other fit dudes only want to top, and my tight ass is pretty enticing to them." It was now Jack's turn to humble brag, which he did knowingly with a big grin.

"I bet you're a little bitch in the sack," Ryan teased back. "Honestly, I'm a little bummed we never tried anything more that summer."

Jack was shocked by how the conversation had changed in an instant. Moments ago they had been joking about their sex lives, and now Ryan was basically admitting he was curious about fucking other guys.

"Yeah man, I guess it was a missed opportunity," Jack tried to play it cool, containing his excitement. "Nothing like two horny young guys getting off together. Too bad we're older now and you're taken."

Ryan stared back at Jack for a moment, clearly trying to think despite all the alcohol.

"Okay man, but actually that's not really true. One of the best things about dating Sarah is that she wants us to be open...so I can fuck whoever I want, whenever I want."

"No way, dude," Jack replied. "That's pretty great. Do you take advantage of that much?"

"Oh yeah, for sure. It's honestly fantastic. But I've never been with a dude."

Now, it was Jack's turn to stare back. He could see where this was going, but didn't want to be weird.

"Well, want to just come back to my place and we can take it from there?" Jack casually threw out the suggestion, knowing it would lead to more.

"Sure man, let's do it."

They finished their beers, paid the tab, and started walking the few blocks back to Jack's building.

-

After arriving, they took up the elevator to the 18th floor where Jack lived. It was a modern high-rise, with views of the Space Needle and the Sound.

"Damn dude, you're living in luxury up here!" Ryan was impressed, staring out the window at the beautiful nighttime view.

"Shame I'm traveling so much for this job, I hardly ever get to enjoy it," Jack responded. "Want a beer?"

"Sure man," Ryan nodded in agreement, then sat down on the couch as Jack opened and brought over two bottles.

They sipped on the beer nervously, not sure what the next move would be. Ultimately, Ryan spoke first.

"I think back to that night in the park all the time, man. There's something unbeatable about stroking your dick with a buddy, especially when you're as young and horny as we were."

"Being outside doesn't hurt, either," Jack added. "You can imagine you're outside with these huge windows. Anyone could see us right now."

Their eyes met, and both knew they couldn't go back. Ryan reached over to Jack, rubbing his crotch through his tight pants. In response, Jack did the same to Ryan, then began removing his belt and jeans. Soon, both were erect and raring for more.

Leaving their shirts on, they both pushed their pants and underwear to their ankles. Jack's 6" cock stood straight at attention, surrounded by a shadow of trimmed black pubes that faded gently into his body hair. But Ryan was clearly the winner with his girthy, 8" cock. His pubes were completely shaved away, making his massive member appear even larger.

"Shit man, you're huge," said Jack admiringly, which made Ryan smile. "I remember thinking your cock felt big in my hand that summer, but it was so dark I hardly got a look at it."

"Yeah man, it never fails to impress. Why don't you play with it?"

Jack reached over with his right hand and began to stroke Ryan's dick. He moved up and down the shaft, and soon began to fondle Ryan's balls using his left. Ryan moaned in pleasure.

"Just like last time, man." Ryan said as he reached over to Jack, grabbing his cock and beginning to stroke it too.

Jack moaned in pleasure from Ryan's handjob. He thrusted his hips, savoring the sensation of firm hands strumming his cock. But quickly, he knew he couldn't let the opportunity for something more slip away.

Jack got down on his knees in front of Ryan, removing the pants and underwear from his ankles and pushing apart his thighs. Grabbing the base of Ryan's cock, Jack touched his lips to the tip and began to suck.

Ryan, scooching to the front of the couch, removed his shirt to expose his thick, muscular chest. Then, he grabbed the back of Jack's head and gently guided it along his cock, encouraging him to get deeper down the long shaft.

"Fuck, that's great Jack. You really know how to suck cock."

Jack continued the blowjob, savoring the manly taste of his buddy. Soon, he felt the tip hitting the back of his throat, holding back his gag reflex as he enveloped the entire cock in his mouth.

After a few minutes, Jack pulled back and stood up. He removed the rest of his clothes, pulling his pants and underwear off his ankles and whipping off his shirt, exposing his chiseled chest, visible abs, and wide shoulders.

"Wow, you look great naked," Ryan said impressed. "I like the trimmed chest hair."

Ryan reached out, grabbing Jack's hips and pulling them closer to him. Then, he began to give Jack a blowjob as he stroked his own dick.

Jack was surprised by Ryan's technique and skill, given that he hadn't been with many men before. He quickly went deep along his shaft, moving back and forth rhythmically with just enough pressure. They moaned together, enjoying the shared experience.

Then, Jack pulled back, leaning down and grabbing Ryan's head.

"This is great, but are you ready to fuck me?"

Ryan beamed eagerly.

"Absolutely. It's all I've wanted since we first jerked off."

Jack straddled Ryan on the couch, grinding his ass along Ryan's cock. It was wet from the blowjob, but Jack spit on his hand and used it to lube up Ryan more, then repeated the process for his own asshole. Finally, Jack propped up his ass and positioned Ryan's cock at the hole, letting it press against him but not quite enter.

"This is it, man. I want you to fuck my brains out." Jack was direct and passionate.

"You better believe I will," Ryan whispered back.

That moment, Ryan held down Jack's hips as he thrust inside Jack for the first time. Jack allowed his ass to relax, taking Ryan's enormous cock quickly. After a few seconds of pain, a wave of pleasure rushed over him, and Ryan thrust deep inside him.

"Fuck man, your ass is so tight," Ryan gasped from the pleasure.

"It'll always be tight when a cock that big is in it," Jack replied back with a smile. "You feel incredible inside me."

Jack began to bounce up and down on Ryan's groin, letting his member push deep inside his hole, against his prostate and even further back.

They both glistened with sweat, pores releasing masculine pheromones into the air. Jack leaned down and kissed Ryan's neck, then moved down to his chest and over to his armpits, savoring their smell and tasting his sweat.

"You're so sexy, Ryan."

"You're even hotter, Jack." Ryan replied. Then, he grabbed Jack tightly and stood up, keeping his cock inside Jack as he brought him back down to the couch lengthwise on his back. Now, Ryan was positioned above Jack, whose legs were propped up over Ryan's shoulders.

"That's some serious strength," said Jack, impressed. Ryan smiled as he began to jackhammer his buddy's ass, enjoying how the new position gave him more control.

Ryan admired Jack's gorgeous, muscular frame as his dick slammed Jack's tight ass, making it red. Jack moaned with each thrust, loving the sensation. For both, the almost-taboo act of fucking a childhood friend heightened the experience.

"Keep it going, Ryan!" Jack encouraged in ecstasy. "Just like that!!"

Sweat rolled down Ryan's chest. Finally, he grabbed Jack's erection and began to stroke it quickly, knowing it would send his buddy over the edge.

"Oh shit, I'm gonna cum!!" Jack shouted as he allowed Ryan to force out an orgasm. His cock erupted, spurting out his load in multiple, massive ropes across his chest.

"Fuck that was so much cum!" Ryan smiled as he continued to fuck his friend. He leaned down over Jack to lick some of the cum off his chest, enjoying the salty taste as it mixed with Jack's sweat.

"You taste so good," Ryan said with heavy breath. "Flip over, I want to fuck you from behind"

He pulled out, allowing Jack to roll onto his stomach. The remaining cum on Jack's chest pressed into the couch, making the leather surface sticky and wet.

Once more, Ryan thrust his dick into Jack, this time pressing his stomach down on top of Jack's body. As Ryan continued to fuck him, Jack grinded his ass back and forth, knowing Ryan would love the additional movement.

"Shoot your load in me, Ryan!" Jack begged his friend.

Ryan's pace quickened as pulled up his chest, giving him more leverage to ram Jack's ass harder.

"I'm so close!! FUCK!!"

Ryan slammed his groin into Jack's ass one final time as he orgasmed. Hot cum rushed out his massive dick, going deep inside Jack's hole. After a few pulses, he pulled out his cock and watched more of his seed spray onto Jack's ass cheeks and hole. Finally, he pushed his wet cock back inside Jack as he collapsed on top of his body, relaxing after a long, hard fuck.

"Goddamn dude, that was a big load," Jack said, looking back at his exhausted friend.

"I could say the same for you, man," Ryan replied after catching his breath.

After a few more seconds, Ryan pulled out and they both sat up on the couch. They glistened with sweat and cum.

"I'm really happy you texted me, Ryan. I had been fantasizing about this for so long, but never thought it would come true."

"Me too, man. Seems like I'll have to make more trips up to Seattle in the future."