Ramble Tales: A First Timer

In the real world, Central Park is known for iconic sites like Bethesda Terrace, Belvedere Castle and Bow Bridge. But, in the gay world, there is one location that is well known above all else and that is The Ramble. 

No one knows exactly when The Ramble became the hook-up spot for many gay men, but it became well known by the 1970’s and 80s due to its easy access yet secluded nature. It’s like a small bit of woodland in the center of New York City.

There have been many tales about the Ramble but the first tale I’m going to tell revolves around a young man staying in the city during a hot summer looking for a release and perhaps finding himself along the way…

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New York City 2003

James “Jamie” Anderson was an intern at an advertising firm for the summer some years ago when he told me his story. At 5’11, blond hair with a toned swimmers build, he’d be considered a ‘twink’ in modern parlance. Back then he was a 20-year-old kid from the Midwest who was still discovering his sexuality. Some call it a second adolescence when you make the connection about being gay. I guess for Jamie it would be a second chance. He slowly came out to his friends at the state college he attended and to a few of his teammates on the swim team. 

Having a knack for entertaining and exaggerated storytelling, a professor recommended him for an internship for an advertising firm over the summer in New York. After applying and getting accepted he worked like crazy to save up for the expenses to come. As luck would have it, the company offered to pay for a dorm in Brooklyn Heights for the summer and he had already saved enough to cover his other expenses, like subway fare to the office, food, and maybe occasional night on the town.

So, finishing up his sophomore year and celebrating of his 20th birthday, Jamie boarded a bus bound for the East Coast. He’d never gone further east than Pittsburg before.

The bus arrived in the height of morning rush hour and after accidentally getting on the wrong train, Jamie arrived at the St. Gregory, a former luxury hotel that had been carved up into dorms for college students.

The room wasn’t much a typical dorm set up Jamie. His roommate was already unpacking when Jamie stumbled into the room.

“Well, hello” the stranger said to Jamie. “Looks like you could use some help.”

 “Thank You!” Jamie exclaimed with relief in his voice as the stranger grabbed his bags out of his arms. You’re the 3rd person to help me today. I thought New Yorkers were supposed to be rude and aloof” Jamie joked. This was true, despite the stereotype of New Yorkers not being friendly, he got directions to the right train and help with hauling his luggage up the broken escalator. However, as is customary for most New Yorkers, they help and then go about their business, so Jamie was often left on his own once again. Today, we call that ‘kind but not nice.’ The roommate, on the other hand, was a different story. After helping Jamie with his two suitcases and his laptop bag he introduced himself as Gino. Gino was also an intern but at finance firm down on Wall Street. Gino had grown up in Connecticut, but his parents, after raising him and his older siblings, retired and fled the harsh winters of Connecticut for the humid swamps of Florida to be closer to their grandchildren. Gino wasn’t quite ready to flee the excitement of the city and elected to stay in New York for the summer and made the St. Gregory his temporary home.

The two had similar tastes in sports, music and movies and got on surprisingly well. Gino was slightly shorter at 5’9 feet, and his Italian-Irish heritage gave him beautiful brown wavy hair, and his Mediterranean features that Jamie, who himself came from Scandinavian heritage, found exotic and intoxicating.

“I wonder if he likes girls, or is he like me?” Jamie wondered to himself.

After they unpacked and got settled, the roommates explored their new building. Some of their fellow floormates led them up to the old ballroom to the top floor. It had a killer view of the city and the Brooklyn Bridge, and it was enclosed so this allowed them to use it year-round. The view was the post-9/11 skyline of a city still in a state of healing, but it still beckoned people like Jamie to take it all in. The main use of the ballroom to was parties and mixers for the interns and students during the regular semester. After dinner and some dancing, Jamie and Gino were convinced by Paulo, a fellow floormate, to sneak up to the roof with some others to have a ‘proper drink.’ Someone snuck in some beers and passed them around. Despite the heat, a slight breeze and company made it worthwhile. Jamie couldn’t believe how much hotter and sexier the guys were compared to back home. Hell, that was reason enough to consider a permanent move after college.  

It was long after midnight when Gino and Jamie returned to their room. They stripped to their boxers, jumped into their bunks, and tried to fall asleep. The next day orientation for Jamie at the firm made him very excited and he couldn’t fall asleep right away. He lay there for a while fighting the urge, but finally gave in. He pulled his hard cock out and quietly tried to masturbate. He imagined his buddy Brad back home. They had played around with each other back in high school even losing his virginity to him on graduation night. He remembered the confusing mix of pain and pleasure when Brand entered his asshole as he slowly stroked his cock under the sheets. After so much teasing and play, Brad popped his anal cherry and with several memorable thrusts, Brad climaxed and filled the condom with his seed. It was the happiest night of his life and for much of that summer life was perfect, but it all came crashing down when it was revealed that Brad had impregnated his girlfriend Cindy and he elected to stay behind and raise the child with her. Jamie was kicked to the curb without a second thought. He was crushed emotionally and almost didn’t finish his first semester of college. But Jamie pulled himself together and did his best to move on. Jamie made new friends and learned to mostly let go of the disappointment of that first love.

I say mostly because Brad still provided enough spank bank material to allow him to come to climax. He removed his boxers and cleaned off the cum from his body and slept in the nude for the rest of the night. Before he drifted off to sleep, he had one word on his mind.

Possibility.

  

The next day, Jamie woke up early enough to head to the showers to get dressed before Gino got up. Not wanting to be late, he joined his fellow interns from the firm and the got on the subway uptown to Midtown. With a bit more confidence than the day before, but still dealing with the sweltering mass of people underground they arrived at the new high rise near Grand Central where the firm, Kincaid, Johnson and Park, was located.

“Hello interns!” a tall and broad-shouldered man said to them as they entered the firms conference room. “Welcome to Kincaid, Johnson and Park aka KJP. My name is Robbie, are you ready for your summer here?”

“Yes!” they replied in unison!

“This will be the summer of hell,” Robbie said. “You’ll be running your young asses doing some of the most thankless tasks imaginable. You’ll feel overworked and underappreciated, and you won’t get paid a penny for any of it,” the man continued scaring the shit out of the group of young hopefuls. “But…on the flipside, you’ll sit in on brainstorming sessions and client meetings, you learn every facet of the industry from strategy and media buying to copywriting and creative development. We will do our best to help you uncover your talents and find your passion. Our goal is to help you figure out where, or even if you fit into the wonderful world of advertising. These internships are converted and not for the faint of heart” Robbie explained. Jamie felt as though he was being imitated into an exclusive club where only the best made it past the hazing.

As inspiring or terrifying as Robbie was, Jamie only heard half of what he said. The man looked like a Greek god and was built like one too. Robbie appeared to just on the other side of 30 and wore it well. Exactly 6 feet tall with slicked brown hair and the classic square jaw that would’ve been found on any actor on the silver screen, Jamie’s mind imagined the six pack abs that lived under Robbie’s tailored suitcoat, and wondered what was hiding under the thin material of his pants. Was Robbie was really packing or did, he get stuffed like Jamie? He wasn’t so sure, but his thoughts forced him to make subtle shifts to ease the excitement in his own Khaki slacks, unfortunately, his underwear made it nearly impossible to conceal the bulge. He made a mental note to wear briefs instead of boxers for the rest of the summer.

“You alright…what’s your name kid?” Robbie asked. Jamie was suddenly the focus of Robbie’s attention and all eyes in the room were on him.

“Jamie,” Jamie replied rather sheepishly. “Sorry, needed to adjust the seat of my pants on this chair.”

“Don’t worry Jamie, adjusting on the fly is part of the art of advertising. You and your fellow interns will get the hang of it,” Robbie said. “Ok, first things first. You’re all going to different departments to shadow someone for the day.  Based on the preferences from the Q and A you each filled out prior to joining us, we did our best to set you up in a position that best suits your interests and talents. You will also shadow other people here from time to time throughout the summer, so don’t fret if your first assignment isn’t your perfect match. Come up to the table, get your assignment and meet the person you’re shadowing.”

After a line formed, Jamie found, to his horror, himself last Jamie began to hope and pray he’d get Robbie. But he was disappointed when Beth, a student from down south in Georgia got Robbie. It was clear that she was also smitten with Robbie, so Jamie had to try and temper his disappointment when the door opened and someone poked in and said, “Oh Robbie, there you are. We have a change of plans. Ms. Carmichael will be getting the Always 16 account, so Miss Beth Robinson will be reassigned to her. The Swimnbourne athletics account will go to you and you’ll be getting Ms. Carmichael’s original intern, um…James Anderson,” the man said.

And just like that Jamie got what he wanted.

After the chaotic first week and avoiding Beth’s death stare, Jamie settled in at the firm. Apart from the daily coffee runs and the absolute HELL Robbie promised, Jamie and his fellow interns were surprisingly valued for their suggestions and insight. The Swimnbourne account was challenging at first but since they sold swim gear and other sporting equipment, Jamie was familiar with their gear and so the two were like a well oil-machine. Jamie would sneak as many glances at Robbie as he could. He noticed how Robbie’s clothes fit so well that it also accentuated his chest, shoulders and even his ass. Once when helping Robbie get something from a shelf, he could’ve sworn that Robbie was also checking him out. At night, Jamie now alternated between his dreams of Brad, Robbie and even Gino taking turns reaming his asshole. The fantasies getting more elaborate as time went on.

Speaking of Gino, despite the different career paths the two meshed well as roommate and their room became the hangout spot for the floor, with music and beer flowing well into the night. The only odd thing was that some nights Gino wouldn’t be back till almost midnight. Jamie didn’t think much of it since it allowed him to consume porn and jerk off in privacy before bed.  

As the first few weeks wore on, the interns became a tight group. Even Beth and Jamie buried the hatchet, she proved to be quite prodigious with the Always 16 account. It’s also because Beth got to shadow Robbie a few times as promised, so that went a long way making the two as thick as thieves.

Beth even confided she knew Jamie was gay and was willing to keep it between them. Plus, they could both gossip about Robbie and the other guys at the office freely at the Seagram Building Plaza on Park Avenue. There they learned the art of people watching with every type, style and walk of life passing them by. Each imaging what life was like with them. Each dreaming that intoxicating New York dream. 

Things were going well, until the events of a Friday morning. That morning it was Jamie, Beth and Scotty’s turn to get the Starbucks run when Beth crashed into the mail cart. Scotty was able to deftly doge Beth tumbling back but Jamie collided with her and thus coffee and pastries were strewn everywhere. Jamie was effectively soaked with his shirt, tie and trousers.

“What happened?” Robbie and another intern coordinator Paige came over from the commotion. Paige collected the shaken but otherwise ok Beth and Robbie took Jamie to his office.

“Hey, go inside that drawer,” Robbie said. “I keep some spare clothes in case of emergencies like this.”

Inside was some spare shirts, ties and trousers there was even socks and underwear, including a brand Jamie wasn’t aware of.

“2-xist” Jamie wondered as he looked at the packaging that showed a midnight blue pair of low-rise briefs that looked more appealing than the baggy pair of Hanes he had on.

“Oh, you can have that one. they’re pretty good. I just got the wrong size by accident. I think they will fit you better,” Robbie explained. “Hey, I’m going to get the meeting started. I’ve already closed the blinds to the office so you can get changed in privacy. If anyone calls just leave a message and head to the meeting. Sound good?” Robbie asked.

“Sure, thing Robbie” Jamie responded.

Jamie changed out of his soiled clothes into the spare clothes and underwear. They all surprisingly fit and as Jamie was about to leave the phone rang.

“KJP, Jamie speaking for Robbie Waters. What can I do for your today,” Jamie answered the phone.

“Oh, Robbie’s not there?” A surprised voice responded.

“No, he’s in a meeting, can I take a message?” Jamie replied.

The caller paused but then said, “Okay just tell him to meet me at the Ramble at 8.”

“Ok, um where is that?” Jamie asked.

“Don’t worry about that. Robbie’s a big boy, this ain’t his first time there,” the caller huffed.

“Okay, Okay Ramble at 8,” Jamie said as he scribbled it on a post-it note. “Who can I say called?

The caller hung up.

Jamie went to the meeting and sat next to Beth, who had also changed clothes. The meeting was a status update for the fellow interns with the person they paired up with. Initially lost in thought over what is the Ramble or where was it was, Jamie had to be jolted back to reality when his and Robbie’s name was called. Despite a rocky start, the presentation went well, and everyone went back to their daily tasks for the day. Jamie was doing some research for the Swimbourne account when at around 4 p.m. he suddenly remembered the message.

Jamie knocked on the door and said, “Hey Robbie, some guy called and said he wanted to let you know he wants to meet you at the Ramble at 8. What is the Ramble and where is it?”

Robbie initially looked surprised at what Jamie said but replied, “Oh yeah that’s probably Daniel, he’s a running buddy. we usually run in Central Park in the evenings. He’s a sometimes actor turned accountant. The Ramble is a wooded area in the park. Ever been?”   

“Oh, I guess I never heard of it before. I mean we get some after work and weekend outings from the program, but not a lot in depth.” Jamie responded.

“Well, it’s nice in the day but it gets interesting at night,” Robbie said. “Let’s just say I’ll explain that some other time. How are you liking the new underwear?”

“Pretty good” Jamie said.

“Tell you what. Head over to Bloomingdale’s, I need you to pick up from the department store my new suit and then have it sent to Tony, my tailor, down on the Lower East Side. Buy yourself some more underwear that you like and have Tony dry clean your clothes. Tell him it’s from me, add the term rush, and he’ll have it done by tomorrow. Put everything on the company card and DO NOT lose it. Wrap up some last-minute work here and you can head back to the dorm for the weekend.”

“Sounds good to me!” Jamie said.

“Well then that settles it and oh keep the underwear between us,” Robbie replied with a wink.

“Definitely,” Jamie Responded.

Jamie left a few minutes later and headed to the men’s department at Bloomingdale’s. Jamie had never been somewhere so sophisticated, but the staff perhaps sensing his greenhorn appearance helped him out and he even scored some new underwear. After getting downtown to the cleaners, true to Robbie’s word Tony promised everything would be done first thing Saturday morning. Jamie took the F train back to Brooklyn, where it dropped him off in an adjacent neighborhood that had just got the moniker DUMBO (Down Underneath Manhattan Bridge Overpasses). The area, still rough-hewed from nearly a century of industry, now flowed with artistic fervor and a sense of purpose. Jamie wondered if this was the type of place he’d like to live. He also was curious about what kind of a place the Ramble was when he saw Gino with a duffel bag over his shoulder.

“Heya roomie, what’s up and where’s your clothes?” Gino asked.

“Long story, but I’m getting them cleaned thanks to my boss.” Jamie replied. “Where are you off to?”

“My Manhattan cousin is going to a wedding tomorrow so I’m staying at his place over the weekend to watch his dog. So you’se got the place to yo’self. Wanna meet for breakfast in his neighborhood? The local diner makes the BEST Belgian Waffles north of 57th Street.”

“That sound cool. Leave me the address, and I’ll meet you at 11,” Jamie replied enthusiastically.

“Cool, bring the gang if anyone’s awake at that hour.”

“See you tomorrow!”

Jamie and Gino hugged and went their separate ways. Jamie marveled at the fact that he was going to have dorm to himself, so he stripped down to the sexy pair of briefs that he was now wearing. He thought about jerking off into them, but he thought against it. Instead, he decided to go to the media center downstairs and look up the Ramble online. Just to quell his curiosity.  After a quick search he found out about the history of the Ramble, but another site caught his attention. It was a website for cruising locations in the city and at the top of the list was the Ramble.

Jamie’s heart skipped a beat. Robbie was gay just like him and was possibly going to hook up with Daniel in a place like the Ramble. And even if he wasn’t, his curiosity and the tent in his pants said he was curious about the prospect of finally getting some much-needed dick.

Looking at the clock and it was saying 6:40, Jamie raced back upstairs to shower and change. He broke out one of the new pairs of underwear, a pair of bright red briefs, and threw on a pair of shorts and a t-shirt. By 7:20, Jamie was on the subway and 20 minuets later he was entering Central Park at Columbus Circle. After consulting a graffitied map he was able to navigate his way to the Bow Bridge, which formed the entrance to the Ramble. Jamie decided to stand near the entrance of the bridge and like at the Seagram Building Plaza, he began to people watch. Tourists and photographers trying to capture the mid-summer sun before it set, lovers holding hands walking through the park and finally parents carrying their exhausted children out of the park content with the day’s adventures.

Jamie almost forgot why he was there when like clockwork Robbie arrived and crossed the bridge. Luckily, he didn’t notice Jamie, but Jamie noticed him and despite claiming Daniel was a running buddy, he wasn’t exactly dressed for a jog but instead he was dressed rather casually. Regardless, Jamie watched him reach the other side of the bridge and then a man of medium build almost immediately follow behind him.

Jamie, realizing he might lose them, quickly followed them across the bridge and into the growing dark of the Ramble. He watched as the two, now next to each other and no longer one behind the other, talk to each other. The other Daniel being a bit more animated about some Broadway show, whereas Robbie seemed to listen to him. Finally, after getting deeper and deeper into the Ramble, the pair found a break in the fence and snuck through. Jamie reached the break and paused. He realized that this was this point of no return. So with a deep breath he plunged in.

Despite the thick trees it didn’t take long for Jamie to find the two men. They stopped near a tree where a third man, a 6-foot 2 tall black man was waiting for them. Broad shouldered and chested he asked what took them so long. Daniel replied they took the ‘scenic route’ Robbie said he only did that so he can talk about the show he’s in rehearsals for.

“Alright, alright, enough chit chat, let’s have our fun before it gets too dark,” the man said.

“Ok then Eddie,” Daniel replied to the man.

Eddie and Daniel started to kiss each other. Daniel was the shortest of the three at 5-foot 7 but kissed with equal intensity as Eddie held his own. Robbie stood off to the side rubbing his crotch, his bulge getting harder as he watched the other two kiss aggressively. Daniel began to fondle Eddie’s bulge and pulled down Eddie’s athletic shorts, which had no underwear and out sprang his thick,long 9.5-inch cock. Jamie’s eyes widened in shock. He’d heard the stereotype of black guys being bigger, but it was another thing entirely to see it in person (in the future, Jamie would learn size doesn’t always matter, but that’s another story).

Daniel proceeded to swallow Eddie’s cock almost completely before the tell-tale gagging sound came out his mouth. Eddie slowly backed out and then began to gently bring his cock back to Daniel’s waiting mouth. Meanwhile, Eddie and Robbie were now kissing, and Robbie stripped off shorts and briefs in one swoop. Out popped a long and skinny 8-inch cock that made Jamie’s ass quiver in excitement. He could feel the precum stain his briefs as his dreams felt like they were coming true before his very eyes. Daniel looked at Robbie’s cock with pure lust and switched to sucking Robbie off for a bit before alternating between the two cocks. This lasted for what felt like forever before Daniel stood up and dropped his shorts bringing his 7-inch cock in full view. He might not have been as big as the others, but once again Daniel’s cock made up for it in presentation. It was uncut, almost as thick as Eddie’s and surprisingly shaven, whereas the others were unshaven. Robbie now took turns sucking off Eddie and Daniel! Jamie watched as his boss slobbered and slurped on the two dicks with as fervor as Daniel was just a few moments ago.

By this point, Jamie had released his cock from his shorts and had begun to jerk off to the scene. He knew he shouldn’t be there and yet he couldn’t imagine anywhere else to be right now. At first it appeared that Eddie was the dominate one with Robbie and Daniel competing for his attention and his sex. But now it appeared that one by one they alternated between sucking and jerking each other off. Eddie was now sucking Robbie’s cock, and rather than be face fucked as the others acted around his cock, he took his time savoring Robbie’s tender extension while Robbie, now shirtless, rubbed his nipples while releasing soft moans from his open mouth. This continued until Eddie stood and moved Robbie into position to eat his asshole, while Daniel moved to have his cock be sucked by Robbie. This muffled Robbie’s moans and were replaced by Daniel’s. Eddie’s thick tongue reached deep into Robbie’s pink hole to open it up for his think, throbbing State Fair Eggplant of a cock that was glistening with pre-cum. Eddie’s tongue work was one of the rare things that made Robbie willing to take such a big cock as Eddie’s. That had been the plan that evening, for Robbie and Daniel to submit to Eddie and then Daniel, the sole bottom of the three, to submit, quite happily I might add, for both.

Jamie watched with great intensity and was extremely aroused by the whole thing. His hard cock was damn near about to burst. He figured he could cum and then slowly leave the scene. His boss wouldn’t know that he watched him in such an intimate manner. That was his plan.

But funny thing about plans.

Just as Eddie was positioning his cock to enter Robbie’s hole. Daniel took a step back and in doing so glanced in Jamie’s direction. The two immediately locked eyes on each other as if Daniel knew Jamie’s predilection for cock was like his own.

“Hold on,” Daniel said to the other men. “We have an audience.”

Daniel walked over to Jamie, who rooted to where he stood was unsure of what to do. He figured that whatever it was, it had to be worth not running away.

“You like what you see?” Daniel asked Jamie as he sized up the young man’s appearance, especially his still erect member in his hands. 

“Uh-huh,” Jamie replied. 

“Would you like to join us? It’s getting to the good part, and I think Eddie has plenty of seed to go around,” Daniel said.

“Daniel, who’s over…Jamie??! What are you doing here?” Robbie hissed with a look of shock and embarrassment.  

            

“You know this kid?” Daniel interjected.

“He’s an intern at work,” Robbie quickly explained.

“Oh, so you’re the one I left the message with,” Daniel said with a bemused smirk. “Aww that’s so sweet he followed you like a puppy.”

“Hey, don’t be such an ass.” Robbie retorted. “And before you ask, he’s 20.”

“Guys it is getting dark, and my cock is deflating. Are we inviting the guy or what?” Eddie answered out into the wood.

“It’s the kid’s choice, you convince him,” Daniel said shrugging and went back to Eddie.

“Regardless of what you chose to do this stays between us, deal?” Oh, and by the way Eddie gets first crack at you. It’s kind of the rules with him. I hope it doesn’t hurt. It took me a few days to walk properly.”  Robbie explained to Jamie who nodded vigorously that he wanted to join in.

“Ok let’s join in.” Robbie said.

Eddie took one look at Jamie and realized that this kid was different. As a habitual visitor to the Ramble, Eddie “Cobra” Clark, had a reputation for picking out first timers and initiated them to the Ramble. Word gets around and eventually Eddie had so many man-on-man encounters in the Ramble, you’d need to book the Plaza Hotel for the bacchanal. So, seeing that Jamie was fresh meat made his dick twitch.

“First Time?” Eddie asked.

“Yes.” Jamie answered.

“Daniel tells me that you’re an intern. You must be far from home.” Eddie inquired.

“Yes, but I can’t think of any other way to spend the summer.” Jamie responded.

“Well then let’s add this under extracurricular activities.” Eddie grinned. “Bend over,” he commanded.

Jamie bent over and began to feel Eddie’s tongue lapping his tight hole. It pushed deep inside him, and he felt sparks shooting up his body feeling an orgasmic sensation within seconds of contact from Eddie’s oral skills. To keep him from moaning too loud, Daniel began to kiss him. Jamie then leaned forward to taste Daniel’s cock. He almost gagged at first on the thick stub of meat, but soon he began to wrap his tongue around this cock. This drove Daniel wild with lust as he began to face-fuck the young man to the point that Eddie gave up on eating Jamie’s ass and let Daniel enjoy it all by himself.

Meanwhile, Robbie stood off to the side, casually jerking off to the events in front of him. He also had some unnatural thoughts about his young charge but had hoped he could survive the summer without acting on them. However, seeing Jamie take Daniel’s cock working his mouth around it, Robbie’s cock jumped back up to its his own stiff salute. Drawn to the youth, Robbie tapped Daniel and Daniel taking the hint stepped aside.

“What the hell he thought, the kid won’t tell.” Robbie thought to himself as he guided his cock to Jamie’s hungry mouth.

Jamie’s heart skipped a beat realizing he’s going to finally taste his boss’s erect penis. Having already had his mouth filled with saliva from slobbering on Daniel’s cock, he eagerly swallowed Robbie’s cock. He swallowed it so well, Robbie was once again impressed by the tenacity and self-assuredness of this kid. He never expected that he would be in this position although he fantasized about the things he could do to Jamie, like railing him at the desk at the office or at his apartment on the Upper West Side, but not the Ramble. Robbie released a slow moan of pleasure as Jamie worked his tongue around his diamond hard dick. He'd wanted to burst so badly, but he knew that it was Eddie’s prerogative to have Jamie so rather reluctantly he removed his dick to give it to Daniel who had been patiently waiting for either Eddie or Robbie to insert their cocks into him. Robbie grabbed a condom and lube from a small bag and proceeded to lube his cock. Eddie did the same and added some extra lube to grease Jamie’s tight hole.

Eddie put one finger into Jamie’s pink hole, which twitched in recognition that something hard had enter inside of him. Eddie then added a second finger reaching deeper inside but not deep enough to reach the boys prostate. That would come soon enough. Eddie was tempted to add a third finger, but he figured he’d played around longer enough. It was time for the main event.

Eddie unwrapped the condom and rolled it down his thick shaft. Eddie silently prayed that it didn’t break and began to ease himself into Jamie who almost yelped in pain but gritted his teeth and took deep breaths reminding himself it was like taking Brad’s cock, if Brad’s cock was a whole inch longer and thicker.

“Just relax,” Eddie said as he slowly removed his cock to give Jamie a moment to recover. A few seconds later he plunged it back in, this time he made it two-thirds the way in before once again pulling out. On the third time, Eddie re-entered the pleasure hole and this time he knew Jamie had bottomed out reaching that sweet spot. Assured that he made it, Eddie begun to thrust deeper into Jamie with the two grunting in unison as Eddie slowly sped up his thrusts inside his newest conquest. Eddie usually didn’t like to go after someone younger as he was a full 20 years his senior to Jamie but with a tight ass Jamie in that sweet spot of being not-quite-a-virgin but still tight, drove the man wild.

Meanwhile, as Eddie railed Jamie, Robbie was in the process of putting his condom on when Daniel said, “No, I want to feel you.”

“You sure?” Robbie asked.

“Yes, got a clean bill of health this week and you’d be the first one in a long while,” Daniel replied.

“Well then,” Robbie affirmed “this is a change of pace” Robbie dropped the condom on the ground, added more lube to his stiff cock and dove into Daniel’s hole. Daniel worked hard at keeping his body and ass looking toned and tight for situations like this. Robbie, who knew Daniel’s body very well, knew he could take the pounding and so unlike Eddie who had to take it slowly at first, Robbie fired at all cylinders pounding Daniel’s ass with the intensity of an express train barreling through the tunnel at top speed.

With both Eddie and Robbie now taking Jamie and Daniel to town with their big dicks the two men grunted like two wild boars in heat while Jamie moaned in utter ecstasy occasionally saying ‘fuck’ multiple times while Daniel didn’t verbalize what he was feeling. He just felt good. The two would occasionally slow down and did a few hard thrusts before picking up speed again. Eddie and Robbie would also kiss each other as this occurred This went on for what felt like forever when Eddie realized that his balls had begun to tighten, and he knew it was time. After all the excitement Eddie knew he wouldn’t last for much longer.

“I’m going to cum,” He hissed. “Where do you want it?”

“My back please sir,” Jamie panted.

Eddie did a few more thrusts before releasing his dick from Jamie and in the next second tore off the condom and with a few jerks of his right hand spewed what felt like a week’s worth of cum onto Jamie’s back. Robbie seeing what had happened next to him let out a hiss and proceeded to release his cum straight into Daniel’s ass. Robbie waited for the eruptions to subside and slowly removed his cock from Daniel’s insides which made a plopping sound. Eddie took his fingers and scooped up some his cum and proceeded to feed it to Jamie who suckled Eddie’s fluid of life off the man’s fingers. The four didn’t say anything for about a minute, all trying to collectively catch their breath when Daniel broke the silence.

“Damn…that was so fucking hot!” he said.

“Agreed, I can’t remember when I came this much in a long time,” Eddie added.

“Jamie, are you ok?” Robbie asked.

“Yes, I’m ok, where’s my shirt?” Jamie asked. The sky had darkened and now it was dark. The four fumbled for their clothes as their eyes adjusted to the dark. In all the frenzy of their sexual escapades, Daniel and Robbie were naked save for their footwear. Jamie was shirtless with his shorts and briefs around his ankles. Eddie, who only dropped his shorts was already fully clothed, waited for the rest to get so some semblance of respectable appearance before leading them back to the pathway. The four passed by other men looking for the same lust that had befallen the four men just a few minutes ago. The closeted banker, the teenage runaway, the voyeur and many others all searching for, anonymity and yet some form of connection in the hot New York summer air of the Ramble mixed with its magic.

The four exited the Ramble and headed to the 81st Street exit with Eddie in the lead, Daniel very close behind with Robbie and Jamie side by side. Daniel looked back and realized that for two of them the night had in many ways just begun.  So he asked if he wanted to head downtown to that new hot bar called Industry in Hell’s Kitchen. Eddie, who wanted to head back to his apartment in Harlem was going to say no when Daniel said, ‘It’s not for me, it’s for them. They need to talk about a few things.’

Eddie saw Daniel’s logic and the two agreed to split off and head downtown. Before doing so Eddie told Jamie to look him up before he left or next time he was in town. As for Jamie and Robbie, sure enough the two walked to Robbie’s apartment a few blocks away. It was a garden apartment inside a former Brownstone mansion on 75th Street. As they walked the air grew heavy with humidity and a low rumble of thunder could be heard in the distance. A thunderstorm approaching.

“Come inside and we’ll wait out the rain,” Robbie suggested. “You hungry? I had a light snack before sex. I can order Chinese before it really starts to pour.”

“Sure, I haven’t really eaten since lunch” Jamie answered. “You think the delivery guy will make it in time?”

“He will.”

Sure, enough 20 minutes after placing the order of orange chicken for Robbie and chicken and broccoli for Jamie and some fried rice to share it arrived five minutes before the first drops and then the rain came down in sheets. The storm lasted about an hour, but the conversation lasted well past midnight with Robbie explaining the Ramble, how he came to it, finding Eddie, finding himself as a gay man and then Daniel whom he shared the apartment with who slept out in the living room on the futon, but would likely go back to Eddie’s place or spend the night at someone else’s place, giving the current circumstances. He said that while him and Daniel were roommates and sometimes lovers, it was their friendship that mattered most and that was a bond they shared. He also reiterated that despite what had happened in the Ramble, it had to stay between the two of them otherwise both would get into A LOT of trouble. Robbie wasn’t exactly out at work so it would be risky if anyone found out.  

“Well, its 12:20 am and it’s too late to put you on the train. Why don’t you spend the night. We’ll get breakfast tomorrow morning and get your clothes from the cleaners.” Robbie suggested.

“Oh, that would be great, but I’m supposed to meet my roommate Gino for breakfast in the morning. Apparently, he’s pet sitting for a cousin in this neighborhood.” Jamie replied.

“Ahh well, I guess that’s probably for the best. Since I don’t know what Daniel’s going to do, you’re more than welcome to sleep in my bed, while I sleep on the futon.” Robbie said feeling a bit disappointed. Despite his warnings about getting caught, he was still a bit jealous that Eddie got to have Jamie’s ass and wanted to feel what it was like. However, not wanting to push the envelope, he figured having Jamie spend the night here was better than trying to navigate the subway late at night.

After cleaning up remnants of the late dinner, Robbie gave him some pajamas that the bottoms were too big for him, so Jamie elected to sleep in just the top and his underwear. Robbie bade him good night and closed the door, but not before planting a kiss on the cheek. Jamie had to resist the temptation to join Robbie out in the living room. It didn’t take long but Jamie and Robbie both found sleep while replaying what had transpired the previous few hours and like Robbie, Jamie wished his ass would go to Robbie at least once.

Meanwhile at Industry

 

“Damn that was a hot bar,” Daniel said as the two exited at 2:30 in the morning.

“Yeah, well most of the guys weren’t my type, but it was fun.” Eddie replied. “Think Robbie still has that kid at his place?”

“Most likely, I’ll probably have to share the futon and hear Robbie snore. I’ll be lucky to get TWO hours of sleep” Daniel responded.

“Well, I’m getting the train home. You wanna come?” Eddie asked Daniel.

“No, I’ll walk Ninth Avenue is that way and it’s a straight walk to home.” Daniel answered.

“See you next time then.” Eddie said with a wink.

As Daniel turned to head west to Ninth Ave which in turn allowed Daniel to double back to Industry, he spotted a young man exiting with wavy brown hair and brown eyes also heading towards Ninth. Daniel sped up and asked if he just came from the bar and the man said yes, he just turned 21 and he was heading to his cousin’s apartment on the Upper West Side on 78th and Amsterdam as a pet sit. Daniel said his roommate has a date and he doesn’t want to go home and disturb them. The young man takes an instant liking to Daniel and offers him a nightcap and a couch for the night.

“By the way, the name is Daniel,” he says to the young man.

“Gino.” The young man replies.

To be continued.

 

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Since this took so long to write, I decided to end it here and I have general idea of where the overall story might end up so if anyone wants a part two or a different perspective let me know! Thanks for reading. 

-AJS