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.
