Welcome to Kahe‘a
© Broken Boundaries Gay Erotica
The drive out to the resort felt like falling off the edge of the world. One minute we were on the last paved road, the next we were climbing through jungle, the sky disappearing behind a wall of green. The cliffs loomed like something out of a Hollywood movie: towering and moss-slicked, half-swallowed by clouds. The air was thick and wet and sweet, buzzing with life I couldn’t see but felt everywhere. It didn’t feel like arriving. It felt like I was being enveloped by something strange and alien but wonderful at the same time.
We were headed to Kahe'a Retreat. Aiden had told me it meant “to summon” in Hawaiian, and as we approached the gated main walls of the resort I definitely felt like I was being pulled in. The place was gorgeous. Whitewashed walls that hid what was inside from view smacked of old wealth despite new construction, but the elaborate, yet minimalist signage on the outside of the resort gave no illusions as to what sort of luxuries awaited within.
Although Kahe‘a radiated opulence, it was surrounded by a landscape that was untamed. The wilderness there was wild. It pressed right up to the walls of the resort, trees heavy with fruit, vines thick as rope, and underbrush that shifted and rustled even when there was no wind. Tropical flowers of every description grew wild from the side of the road while a manicured patch of planted perennials sat looking rather out of place near the main sign.
It was breathtaking.
It was like nothing I’d ever seen in my 19 years.
The driver of our oversized SUV pressed a button on the gate intercom, mumbled some pleasantries to whoever was on the other end of the line and a few moments later, the gold-painted gates mechanically sprung to life, gracefully withdrawing and opening the way for us into the resort.
As we passed through the threshold, Tyler clapped his hands on his thighs excitedly, “It’s finally happening, boys! We’re here!”
Connor joined in Tyler’s jubilation, “Damn right, bro! One week, no parents, no other guests, this entire place to ourselves to do whatever – the – fuck – we – want!”
Tyler and Connor high fived each other while Aiden, Bryson and Grant made noises of agreement.
I sat quietly, still taking it all in.
We drove down a long road through thick jungle as we approached the Kahe‘a campus area. As we got closer to the main building, we passed the pool area. It was just as stunning as everything else I’d seen before. Set flush against the cliff’s edge, it looked like it might spill over into the sea if you breathed too hard. I looked at it, and for a moment, it felt like the whole world disappeared — no horizon, no bottom, just water and sky.
I was quiet for a reason; I was the odd man out on this trip — for a lot of reasons.
I’d been friends with Aiden, Bryson, Connor, Grant and Tyler since 9th year. We’d attended a private all-boys school together, very posh, uniforms, fencing team, all that stuff. The difference between me and my friends was that I’d attended the school on a full bursary while their tuition had been fully funded by the Bank of Mom and Dad. At $75,000 a year, that was saying something.
The other major difference between me and my friends was that I was gay and they were all straight. In addition to being one of the only kids at school whose parents didn’t own a yacht and a summer home in some small European country, I was a gay boy in an all boy school. I’d navigated those waters like an eel slipping through the rocks of a coral reef and I’d managed to survive.
My friends had always accepted my financial situation, but things changed when they found out I was gay. It wasn’t that they didn’t accept me anymore but being an all boys school where most of us didn’t know many girls our own age, they naturally started to get ideas. It started simply enough with hand jobs for Tyler and Grant in the bathroom at lunchtime. Before long they’d told the other three what I was doing and Aiden, Connor and Bryson wanted their turn. I was happy enough to oblige; my friends were all hot and I was 15 and horny.
Soon enough, things progressed to blow jobs with Bryson and, again, it wasn’t long before I was sucking them all off on a fairly regular basis. We were all pretty satisfied with the arrangement. They got their rocks off, and I got to live out a lot of gay college boys’ dreams.
But things between us changed after that.
I’d always been on the outer fringes of the group because of my financial situation. There were events I just couldn’t attend — concerts, galas, fashion shows, internships, vacations — but after I started putting their dicks in my mouth, they really started to see me differently.
It wasn’t that they treated me badly. They didn’t do anything homophobic or reject me outright, if anything they spent more time with me due to my newly discovered usefulness, but they definitely didn’t quite see me as the same type of friend they all saw each other as anymore. How could they, I guess?
It’d never gone further than blowjobs; they’d never asked, I’d never offered, but I’m pretty sure I made them some of the happiest boys at that school for a few years…
This was the first time I’d ever been on any kind of vacation with the guys, and it was as a college student on our first college trip, all by ourselves. They’d all been on trips together before, so I couldn’t help but wonder why they’d invited me this time. It was nice, sure, but I had never been on the agenda before, and it wasn’t really part of our dynamic.
Well, I wasn’t going to complain, this place was beautiful, I had a whole week to be here with my friends, and I was going to take advantage of it. The boys’ parents had paid what I understood was something like $500,000 to rent the place out for us for the week, staff included, and I wasn’t going to let my intrusive thoughts ruin what might be a once-in-a-lifetime opportunity for me.
After the long, winding journey down the jungle road to the main building of Kahe‘a we finally arrived at the main building and our driver stopped to let us out. Tyler led the way, as always, charging through the front doors to see what the resort had in store and claim the space for himself. Hotel staff seemed to emerge as if from nowhere, like someone had summoned them with a bell only they could hear and descended on our vehicle to start taking our bags and helping us to our rooms.
Once we were settled, the Resort Manager met us briefly in the lobby to explain the arrangements. Impeccably dressed to match everything else in the place, he let us know that we had the entire grounds exclusively to ourselves, all 10 villas, to which he provided us the keys and that we could do as we pleased with the facilities while we were there.
Since there were only six of us, Kahe‘a would be operating without its full staff compliment, so no lifeguard — sweet — no security — sweeeeet — no bartender, so we’d have to serve ourselves — had we died and gone to heaven? The staff who were on site would mostly be there to clean up after us, remaining unseen, tidying when we weren’t around and only showing up if we called. Even though I’d gone to school with these guys for four years, I still marvelled at the sort of wealth that was required to purchase these sorts of indulgences.
After our chat with the Manager, we decided to look around and check out the villas and the facilities. It had been months since I’d seen any of the guys, so I also took the opportunity to check them out and see how they’d changed since I last saw them before college.
Aiden looked like someone had genetically engineered him for a varsity team photoshoot. His sun-bleached blond hair was a little longer than it had been in school, falling over his forehead in soft waves, and his skin had that even, golden tan that only came from generational wealth and private trainers. He’d filled out too—chest broader, arms thicker, still lean but with definition you couldn’t ignore. There was always something casual about his hotness, like he didn’t care what you thought because he already knew you were looking.
Bryson’s features had gotten sharper in every way. His jet-black hair was perfectly styled, swept back and held in place like a model’s, and his features were symmetrical like he was carved from stone. High cheekbones, straight nose, pale skin that was the envy of boys and girls alike. His eyes were pale blue, almost grey, and still gave the impression that he was sizing you up every time you spoke. Even now, wearing a wrinkled T-shirt and slides, he looked like someone who could walk into a gallery opening and get handed the champagne tray by mistake.
Connor had always been big, but now he was just massive. His buzzed sandy blond hair made him look even more like the kind of guy who’d bench press your girlfriend for fun. He had thick arms, a wide chest, and calves that made gym rats jealous, but there was a calm to him that made it work. His face was broad and tanned, with soft brown eyes that made him seem approachable even when he was cracking his knuckles. If the rest of them were flashy, Connor was the anchor.
Grant looked like he’d tumbled out of a GQ spread after a long night of bad decisions. His reddish-brown hair was messy, though it probably took effort, falling over his forehead in lazy curls. Freckles dusted his cheeks and nose, and his grin spoke of quick wit and unspoken challenges. He was skinnier than the others, lanky almost, but the sort of lean that suggested speed over strength. Every time I looked at him, I remembered that power acutely.
Tyler was still the prettiest one. His hair was that near-white platinum blond that caught the light at every angle, freshly cut and styled to perfection, not a strand out of place. His body was tight, muscular without being bulky, and he knew exactly how to pose so you noticed. His skin was smooth and lightly tanned, and his teeth were the kind you only get from expensive orthodontics. Watching him adjust his shirt in the reflection of the villa window, I got the sense he’d been waiting his whole life to be seen.
And then there was me… My hair was soft brown and always a bit too long, the kind that fell into my eyes no matter how many times I pushed it back. My features were sharper than they used to be, but I still had that boyish thing going on— soft lines, smooth skin, what some might call doe eyes. I wasn’t as broad or cut as some of them, but my body was lean and tight in a way that turned heads when I wanted it to. I didn’t walk into a room and take it over. I was more of a slow burn. I was cute, not striking or handsome, but I was perfectly OK with that.
All in all, we were a hot bunch. I’d often joked that we’d make a great boy band. The joke hadn’t landed as well with the guys as it had with some of the female friends I’d met online but it was true, the cover of that album alone would sell millions of copies.
After looking at everything Kahe‘a had to offer, we each found the villa where the staff had left our bags and set about unpacking. My door was unlocked so I didn’t think anything of it when Tyler walked into my room without knocking — it was his way to cross boundaries.
“Hey, Tommy,” he said. His voice hinting that he was stopping by to do something more than just check in.
“How you liking the place?” He asked.
“It’s absolutely amazing,” I responded. “I can’t believe I’m here. I’m so grateful you guys brought me along!”
Tyler flashed one of his award-winning smiles and then said, “Our pleasure. We had all the villas anyways, so it didn’t cost extra. We all figured we’d enjoy having you here too!”
I smiled back, still unable to believe my luck at being here.
Tyler headed back towards the door turning his head towards me again as he walked.
“Well, get yourself all set up in here. This villa will be getting the most use out of all of them, I’m sure! See you out there soon.”
Without another word, he walked out the door and closed it behind him.
I was a bit confused by what he had said, did he expect me to spend more time in my room than the rest of the guys because I’d never had the chance to vacation at a luxury resort like this before? Heck no! I was going to be out taking advantage of everything this place had to offer, just like the rest of them.
I spent the next thirty minutes getting my villa “set up” as Tyler put it, then went out to meet the boys. Everyone else already seemed to have finished unpacking by the time I got out and they were gathered by the pool chatting casually when I arrived.
“Hey Tommy!” Connor yelled.
“Hey guys!” I shouted back, across the courtyard.
As I got closer to the pool, I could see that most of the guys had already changed into their board shorts and were shirtless, soaking up the midday sun. Tyler, ever the adventurous one, had already managed to score himself a drink from somewhere. Although I wanted to focus on starting my vacation, the sight of their shirtless bodies, now that much more developed after a year away at college, brought back horny memories of our times in prep school.
Me on my knees.
Their cocks in my mouth.
Their cum on my breath.
It didn’t help that their biceps had even more flex to them every time they moved now, that their abs were just that much more chiseled, even their calves.. oh you get it.. they were dripping sex, without even trying and I was the solo gay boy there, trying to play it cool, even though I knew exactly what each of their dicks looked like… and smelled like… and tasted like…
I entered the pool area, absent of any staff just as the manager had advised, and joined in the banter with the guys. We spent the next two hours catching up as Tyler fetched bottles of expensive liquor from — wherever he got it from — and the afternoon sun crept into the horizon.
The boys all had stories to share about girls. I was crestfallen. Pathetic a thought as it might have been, I’d secretly hoped the guys would at least be open to revisiting some of our prep school activities while we were here at the resort. Unlike them, I’d been stuck at home for university, and I hadn’t really had much of a chance to experiment sexually with other guys. My friends however, had been privy to the full college experience, it sounded like, they’d gone all the way, they’d actually fucked.
Not only that, they were talking about some wild stuff too. Things I’d only seen in porn. I’m sure some of it was typical college guy bragging, but still, I was jealous of those girls, imaginary or not. As the conversation wore on, and I’d heard story after story about their conquests I gave up any hope of seeing their cocks again this trip and decided to focus on enjoying the holiday and just got caught up in the conversation and the fact that my friends had chosen to include me this time.
When the sun began to set, we moved to the dining room, where dinner had already been set out for us, as per the arrangement. Once everyone was seated at the big round table the staff had prepared for us, Tyler began to speak:
“So first of all bros, I want to say how awesome it is to be here with all of you!”
A round of raucous agreement.
Tyler continued, “I also wanted to welcome Tommy to the resort, I know this shit is all new for you, but I think you’re gonna enjoy this week the most of us all!”
The guys cheered, Bryson slapped me on the back approvingly.
Feeling grateful and still curious about the invite, I felt compelled to speak.
“Thanks so much guys, for having me here. This place is fuckin’ awesome and I cannot wait to tear shit up this week.”
Now the burning question.
“I was honestly a bit surprised you invited me.”
I hadn’t honestly expected an answer, especially not so fast, but Connor jumped in to lighten my burden.
“Well, Tommy, to be totally honest…” Connor looked at the others, “we kinda invited you for a reason.”
Aiden smirked, Tyler chuckled to himself, a knowing look spread across Grant’s face.
Connor went on, “Our parents agreed to rent out this place for us, BUT — they wouldn’t agree to let us bring any girls along.”
My stomach sank but my heart rose.
“They weren’t willing to pay for us to go to a regular resort because drugs, kidnappers, blah blah, but they would send us here, and I’m sure you heard about all the fine things we’ve discovered at college this year…”
I knew where Connor was going, “You want me to suck your cocks ag—”
Tyler interrupted me, “Let the big man finish, Tommy; we’re gonna explain everything; don’t worry.”
Connor started again, “Yeah, so as I was saying, we learned that we like a lot more than just getting our cocks sucked while we were at uni this year.. yeah.. fucking.. for sure.. but some kinky shit too..”
Aiden threw his head back, tossing his hair out of his eyes and then fixed a mischievous stare on me.
I gulped.
Tyler picked up for Connor, “What my man is saying is, we all know you want our shit, you have since we were in school together. This was the vacation we got, not that it isn’t sick, but there are no girls here so you’re going to fill in and we’re going to try out all the new things we discovered we liked with you. Make sense?”
I thought about it for a split second and mentally agreed. Of course I wanted another chance to get with these boys. Now they wanted to fuck me too? It was a dream. Connor had mentioned some kinky stuff, but I’m sure I could handle it. A little foot rub here, some light spanking there. What could a few, sheltered, rich college boys possibly get into?
Famous last words.
I looked around at the assembled hot faces, each of them staring at me expectantly now — and maybe a little lustily too — and I replied the only way I possibly could:
“When the fuck do we get started?”
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