The Straight Boys Took Me On Vacation

I'm Tommy, 19 and fresh off my first year of college. Five of my rich, straight friends took me to a luxurious Hawaiian island resort that their parents rented just for us. With no girls allowed they have me serving as their kinky gay sex slave and I'm loving it. Today one of my friends told me he wants to piss on me.. and I'm gonna let him...

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Hawaiian Showers

© Broken Boundaries Gay Erotica

We caught up with Aiden, Grant, and Tyler at the cold plunge pools, tucked away behind the main gym pavilion. It was quieter there than the main pool but just as carefully designed. The area wasn’t indoors exactly, but it wasn’t fully outdoors either. Heavy wooden beams framed an open-air roof overhead, with wide slats angled to let in shafts of sunlight and the occasional breath of jungle breeze. The whole setup felt private and rich; it felt like somewhere I didn’t really belong.

The pools themselves weren’t big. Each one looked more like an oversized stone tub sunk flush into the pale slate flooring, smooth and clean-lined, the water dark and glassy until someone broke the surface. There were three in total, arranged in a neat row with enough space between for a couple of those woven lounge chairs the resort seemed to have everywhere. Black volcanic rock lined the edges, and little bamboo signs warned about temperature drops, as if the place wasn’t already expensive enough that you’d know what you were getting into.

Aiden was standing near the middle one, arms crossed, glancing down like he was sizing it up. Grant was crouched beside the first pool, fingers dipped in up to the knuckle, his grin sharp as ever. Tyler leaned against one of the wooden beams with his phone in hand, half-scrolling, half-watching. None of them had actually gone in yet. It was clear they were just scoping things out, talking quietly about trying it after their next workout. Of course they were going to work out, even on vacation, they’d become so focused on those bodies since they started at college.

As we walked towards them, Tyler’s eyes rose from his phone to meet our approach. He fixed his gaze on me first, threw a knowing smirk my way and then made a lewd gesture with his hands and mouth mocking a blow job while winking at me. He was clearly mocking me again, but it wasn’t entirely unfriendly. He finished the whole flourish with a thumbs up as though he approved of what I’d just been doing — or maybe it was his own mock performance. Whatever his intentions, it still triggered a wave of humiliation that coursed through my body like wildfire.

Not because I’d knelt for Connor and Bryson and swallowed their loads on the tennis court. It was what Tyler didn’t know — the rim job I’d given Connor — that had my cheeks flushing with heat. I mean, I’d always figured rim jobs would be a part of my sex life. They were in so many of the videos I’d watched. But it was always the top licking the bottom’s hole to get him ready for a good, hard fucking. If anything, I might have seen a mutual rim job here and there but I’d never seen a guy lick another dude’s ass just to make him feel good. Definitely not when that guy wasn’t going to get fucked afterwards.

I wasn’t sure if that was a normal thing, even in the gay world, but Connor had wanted it and I’d done it without so much as a second thought. I think I’d actually enjoyed it. I licked his ass even though I wasn’t going to fuck him and I got off on it. What did that make me?

Tyler didn’t know about the rim job yet, but based on how things had been going so far, I was sure everyone would find out soon. Would the other guys be interested in trying rim jobs out too? It hadn’t been bad or anything but the list of tasks I was going to be expected to perform this week was expanding quickly. Cock sucking, foot stuff, spanking if I was bad, rim jobs now and I still hadn’t seen what else these boys had planned for me. Not to mention the fact that they still hadn’t fucked me.

I wanted them to fuck me so bad…

Whatever else they had in store was definitely worth it if it got me there.

Connor alerted Grant and Aiden to our arrival with a sharp, “Yo!”

Grant withdrew his hand from the plunge tub quickly, as though Connor had startled him, then his face quickly shifted to one of his classic, easy smiles as he returned Connor’s greeting.

The other three walked towards us and we formed a cluster a short distance from the pools near the glass paneled, wooden doors to the resort’s cigar and whiskey lounge.

“How’d it go?” Tyler asked.

Bryson leaned into the circle and confirmed my earlier suspicions, “Tommy licked Connor’s ass.”

He burst out laughing.

The others followed suit — except Connor. Connor looked very satisfied with himself and even folded his arms across his muscular chest for added conviction. He looked like a god ready to attend a white party in that moment.. dressed in a tight white tank top and tailored white chino shorts that cut clean just above the knee, crisp and fitted without looking stiff, like they’d been pressed by someone whose whole job was just ironing expensive rich-boy outfits.

“For real?” Tommy croaked.

“Yup.” Bryson replied, turning to me for confirmation.

As if any was needed.

Now all eyes were on me again, something I was becoming accustomed to. I’d always been the hanger-on, the shadow, the whisper in the room but here, on the remote island of Kaua‘i, I’d become the main attraction. Not the lux facilities or the epic scenery. Everything else seemed like a sideshow compared to the spectacle I was putting on for my friends. I felt a little bit like a porn star and…. I didn’t hate it?

Maybe it wasn’t a way I’d ever envisioned attracting attention, but it felt great to be in the limelight — even if this whole thing was a little strange.

Of course, I didn’t expect the next question.

I probably should have.

“What did it taste like?” Grant asked.

I looked at him hard to make sure he was serious.

Grant didn’t blink.

“What did Connor’s ass taste like?” I asked. Less because I needed clarification or confirmation than because I needed time to collect myself and think about how I could possibly answer a question like that.

“Yeah,” Grant pressed. Now everyone was interested. Even Connor looked like he wanted to know.

I wasn’t sure I could describe the taste of Connor’s butthole. For one thing, I’d been so distracted by what was going on, I hadn’t had much time to focus on the taste. I was too occupied with trying to keep my tongue where it belonged and with the thoughts raging through my head to really consider Connor’s taste.

Besides that, what little I could remember wasn’t really something I could readily identify or compare with something else. There wasn’t anything you could order at McD’s that tasted just like Connor’s ass. It was heady, thick, a little sweaty, not like other skin but not like his cock either. I didn’t have time to compose a thesis though so what I ended up saying was:

“It tasted like ass— I guess…”

The guys looked at me like I’d just told them puppies grow on trees.

Bryson exhaled through his nose, slow and disappointed, like a teacher looking at a quiz paper with nothing but a name written on it.

“Tommy,” he said finally, voice dropping into that deliberate, professor-type cadence he always pulled when he wanted everyone’s attention on him. “I’m really trying not to be that guy right now, but... ‘It tasted like ass’ is just basic.”

He uncrossed his arms, letting them fall to his sides in this slow, theatrical way, like he was literally lowering the bar for me.

“I mean, seriously. That’s the answer? That’s what you went with?”

He glanced around the group now—Aiden, Grant, Tyler, even Connor—waiting for agreement.

“It’s not just wrong,” Bryson continued, pacing a step, “it’s lazy. It’s disrespectful to the experience. That’s like if someone asked you about a five-star meal and you said, ‘It tasted like food.’ Come on.”

Grant was already laughing. Aiden half-covered his face, shaking his head like he couldn’t believe it either.

Bryson didn’t stop there.

“Look—when you say ‘it tasted like ass,’ there’s no weight to that. It’s got no flavor. No picture. No effort. And I get it, you’re flustered, whatever... but if you’re gonna be out here licking one of us, in public no less, you owe it to yourself to give a proper review.”

His voice shifted slightly—calmer now, almost instructive.

“And I get the ‘I guess’ part too,” Bryson added, eyes flicking back to me. “That’s you trying to play it safe. Pretend it didn’t affect you as much as it did. But we can all see it, bro.”

He glanced pointedly down at the cage, then back up, eyebrows lifted. No one needed to say anything else.

“So here’s what we’re gonna do,” Bryson said, stepping in closer like he was about to drop real knowledge. “I’m gonna give you the official breakdown. Step-by-step.”

He held up three fingers now, steady, like this was about to be on an exam.

“Step one: Salt level. Is it fresh-sweat salty? Dry-skin salty? You don’t need to get fancy, just give us the ballpark.”

One finger down.

“Step two: Texture. Is the skin smooth? Is there stubble? Little bit of both? This is about feel as much as taste.”

Another finger down.

“Step three: Comparison. That’s where most people screw it up,” Bryson went on, pacing again, voice dipping casual like he was talking to himself. “You don’t pull some random flavor out of your ass. It’s gotta be real-world stuff. Basic. Sweat and skin and whatever. Shit you don’t think about until someone asks.”

Bryson paused, looking me over like he expected me to start taking mental notes.

“Because ‘ass’ could mean anything, Tommy. We certainly don’t know what it means. And as the official designated ass-taster for the week, you should be able to report back with accuracy.”

Aiden let out a low laugh. Grant made a quiet little “facts” noise under his breath.

Bryson wasn’t smiling yet, though. He pointed a finger at my chest now, casual but direct.

“So let’s go again,” he said. “Connor’s ass. Salt level. Texture. Comparison.”

His mouth twitched now, finally letting the grin show through.

“And try not to embarrass yourself twice in a row.”

I hadn’t even noticed that I was hard again until Bryson had pointed it out. I couldn’t control it anymore. Between the fact I hadn’t been able to jerk off since the night before we’d arrived and what I’d been doing for my hot, fucking friends, hard just seemed to be my default. The fact I didn’t even notice anymore sorta worried me though.

So there I was, about to give my own David Attenborough narration of “The Deep Dive Into Connor’s Ass” and I was still struggling to find the right words. I wasn’t sure if I should try to be flattering and make Connor feel good or whether I should just lay it out as flat and honest as I could and hope for the best.

What kind of person finds themself making these kinds of decisions?

“Connor’s ass tasted kinda like what I expected it would. It was a bit sweaty from all the tennis but it wasn’t really bad overall.”

“He was practically moaning,” Connor boasted.

I tried not to roll my eyes before continuing.

“He doesn’t really have any hair back there, which was nice for my first time.”

Chuckles all around.

“The skin was kinda… I don’t know ridged… no… like textured maybe? I could feel all the creases and stuff with my tongue. But it was different around his hole. Really firm. Like when you’re trying to get the last little bit of something out of a tight spot with your tongue. It was actually hard work to try and fight against the pressure his hole was giving me.”

“Aww, poor, Tommy” Tyler cooed dramatically.

I tried my best to finish the humiliating task.

“And yeah.. the taste… it was like nothing I’ve ever tasted before.”

“The best thing you’ve ever tasted, you mean?” Connor nudged.

“Ha-ha,” I fired back. “It wasn’t the worst thing I’ve ever tasted for sure, but I definitely prefer the food the resort puts out. I dunno. It was like musky and…manly.”

I’d run out of adjectives, and I could only hope they were satisfied with my description. I looked at my audience any sign of approval, any indication that I was off the hook. They didn’t give me anything, but they didn’t push for more either.

“I’ll definitely have to try that out for myself,” Tyler said.

A reprieve.

“Me too,” Grant added.

“Why not, I’m in,” Aiden injected.

“You guys are crazy,” Bryson retorted. “I’m not letting anyone mess around with my asshole like that.”

Bolstered by the fact that everyone else was joining in on the fun, Connor threw Bryson a cocky look and simply said, “Feels good though.”

With that, discussion over what to do next began. Lunch wasn’t too far off so we didn’t have time for anything major. Eventually the guys settled on the pool.

It was almost normal there except for the fact that they were all dressed and I was still completely naked. Tyler managed to connect his phone to the sound system, and soon The Kid Laroi, d4vd, Benson Boone, and Lil Nas X were blaring through the pool speakers, peeling away some of the elegance and giving it a surreal cabana-club feel.

It was perfect. The surf kissing the beach in the background, the wind stirring the trees ever so slightly, the smell of the sea water in the air, our favourite music bringing it all to life. For close to an hour I forgot that it was only a matter of time before one of my friends made some sexual demand of me again. A demand that might require me to do something else I’d never done before, push another boundary.

The pool music tapered off as Tyler reached for his phone and cut it off mid-track, leaving the air quiet except for the rustle of palm fronds. That was the unspoken signal: time for lunch. No one said it out loud, but we all moved at once, standing and falling into step as a group, six across the stone pathways toward the main dining room, surrounded by the same lush jungle that pressed up against every building on the property. My cage felt heavier with every step, a constant reminder swinging between my legs, but no one said anything.

The dining room looked the same as it had that first night—sleek and quiet, with those dark hardwood panels broken up by tall archways that let the afternoon light in like gold ribbons. The big round table was already set for us, fresh white linens and polished silverware glinting in the sun. Plated starters waited at each seat: grilled shrimp skewers laid over shaved cucumber with some kind of light green sauce drizzled artfully across the plate. It smelled citrusy and sharp in a way that made my stomach growl before we even sat down.

The staff had disappeared as soon as the table was ready. Like always, the luxury felt quiet instead of flashy. Expensive in that way where no one had to say it out loud.

We ate mostly in silence at first, except for the clink of silverware and the occasional comment about how good everything was. Once we made it past the appetizers, the main dishes were already waiting on discreet warming trays built into the table: braised short ribs over soft polenta, grilled mahi-mahi with mango salsa, roasted vegetables in heavy ceramic bowls still hot from the oven. There was fresh bread on the side, buttery and crisp on the outside, pillowy on the inside. It was easily the best meal I’d had in months.

By the time we were halfway through the mains, conversation started picking back up again.

“So what are we doing after this?” Grant asked, his mouth half full of short rib.

Aiden wiped his mouth with his napkin before answering. “Weren’t we saying paddle boards and windsurfing earlier?”

“Yeah,” Connor agreed. “The windsurf setup looked sick too. We should hit both.”

There was a round of nods and agreements from the others. I just stayed quiet and ate, half-listening, half-thinking about the way the sunlight caught on Bryson’s hair from where he sat next to me. Even doing something as simple as cutting a piece of fish, he looked like he belonged in a magazine.

“Alright,” Tyler said, setting his fork down like a judge calling court back to order. “Windsurfing and paddle boards after lunch. Settled.”

That felt final, but then Aiden leaned back in his chair a little and stretched.

“First, though,” he said, casual as hell, “I gotta piss.”

Nobody said anything at first. Aiden glanced around, almost smiling now.

“And actually,” he added, voice a little quieter but definitely not shy, “I’ve been meaning to bring this up. Since we’re trying new shit this week.”

That got a little more attention. I looked up from my plate. Grant raised an eyebrow.

“Go on,” Tyler said.

Aiden scratched at his jaw, eyes flicking between us like he was testing the waters.

“I’ve been watching a lot of piss porn lately. Guys pissing on girls, girls pissing on each other. Sometimes drinking it too.” He said it flat out, no pause. “It just looked kinda hot.”

Grant made a noise that was half laugh, half choke. Bryson leaned back in his chair, arms folded, one eyebrow raised in that judgmental way he had. But he didn’t say anything yet.

“For real?” Grant asked.

Aiden nodded. “Yeah. Haven’t tried it before. Figured now’s the time. Since we got Tommy here.”

That hit me with this weird jolt, somewhere between nerves and curiosity. But no one looked grossed out. Surprised, yeah. But not disgusted.

“Huh,” Connor said. “Whatever, man. Do you.”

Bryson finally spoke. “That’s... definitely a choice.”

Aiden grinned. “I know it’s not for everyone. But I wanna see how it feels. Figure I’ll take Tommy outside after this, try it out.”

Tyler tilted his head a little, looking curious now. “You’ll have to let us know how it goes.”

“Yeah,” Aiden said. “I will.”

The conversation shifted after that. We finished up lunch, everyone cleaning their plates and grabbing one last piece of bread. As we pushed back from the table, Bryson clapped Aiden on the shoulder with a dry grin.

“You’re crazy, bro.”

Aiden just laughed. “Guess we’ll see.”

As we left the dining room, Aiden caught my eye, his voice dropping just for me. “You cool with trying that out, man? No pressure.”

I swallowed, pulse quick in my throat, but I nodded. “Yeah,” I said. “I’m good.”

That was all it took.

Aiden led me down one of the smaller stone walkways off the main path, toward the edge of the resort grounds. Past the last set of pool chairs and umbrellas, there was a stretch of grass framed by palm trees, just private enough. You could still hear the ocean rolling in steady behind the greenery.

He stopped when we were clear of sightlines, hands resting on his hips like he was surveying the spot.

“This works,” he said casually, glancing around once.

I stood there, awkward and cage-heavy, arms crossed over my chest like that might help somehow. My mouth felt dry. I didn’t know exactly where to stand or what I was supposed to do, but I waited.

Aiden noticed. He looked back at me, one eyebrow raised, grin flickering across his face.

“Relax, man,” he said. “It’s not like I’m about to fight you.”

I huffed out a half-laugh, shaky.

Aiden stepped in a little closer, reaching down to undo his fly like it was nothing. No hesitation. That alone made my pulse jump again. I wasn’t used to seeing him like this. Sure, I’d seen him naked plenty of times back in school—locker rooms, house parties, whatever—but this was different. This wasn’t some drunk dare. This was him wanting to try something. And me standing there letting it happen.

He shifted his stance slightly, aiming down, and then it started—a steady stream, warm and sharp against my skin. It hit my chest first, right above where the cage sat. I flinched. Not because it hurt. Just the shock of it. The heat and weight running down me. Against my stomach, down my thighs.

The smell hit next. Clean and sharp, but definitely piss. There was no pretending otherwise.

My first instinct was to wipe it off. But I didn’t move. I made myself hold still, standing there under it, looking right at Aiden while he let it go.

It wasn’t fun. Not in the normal way. But there was something about it—something about standing there for him, giving him that moment—that got to me. That made my heart pound. Like even if the act itself was weird, gross even, the fact that it was Aiden, that it was for Aiden… it meant something.

By the time the stream slowed and finally stopped, my skin was streaked and warm, and I was hard again. Fully. No chance of hiding it.

Aiden tucked himself back in, glancing down at me as he zipped up.

“That wasn’t too bad, right?” he said casually.

I dragged my hand across my chest once, wiping at the slickness, then looked back up at him.

“Weird,” I admitted, voice quieter now. “But not bad.”

Aiden grinned wide, looking satisfied like he’d just landed a clean hit on the tennis court.

“Knew you’d take it like a champ,” he said, clapping me once on the shoulder before turning back toward the path.

Aiden started back toward the path but paused after a few steps, glancing back over his shoulder.

“Come on,” he said. “Let’s get you rinsed off.”

I followed him automatically. My skin felt warm where it had dried, but it wasn’t as bad as I’d expected. Mostly it just felt like I needed a quick shower, nothing more serious than that. My mind was quieter than I thought it would be. Like some part of me had been holding my breath and could finally let it out.

We cut back through the pool deck without saying much. Aiden didn’t make a show of it, just walked straight over to the poolside showers—the tall metal fixtures with the bamboo screens around them, tucked along the far edge.

He twisted one of the handles. Water burst out cold at first, then warmed as it steadied into a stream.

“Hit that before you drip on the floor,” he said, already pulling his phone from his pocket like it was just another day.

I stepped under without needing more of a cue. The water hit my shoulders and chest, rinsing everything off in smooth, steady waves. I stood there with my head down, both hands braced on the stone wall in front of me. The spray felt good—normal. No big moment, no drama.

When I stepped back, I shut off the handle and grabbed a towel from the stack beside the showers. By then, Aiden was leaned up against the railing again, phone in one hand, typing something out like nothing special had just happened.

“All good?” he asked without looking up.

“Yeah,” I said, towel slung around my neck. “I’m good.”

Aiden just nodded and kept scrolling.

I wasn’t sure what I’d just experienced, but somehow I felt closer to Aiden than I ever had before. Humiliated too, but we’d just shared something so intimate I didn’t know how to describe it. Not unlike my experience with Connor.

These boys were testing my limits and I was learning to love it. I was doing things I’d never imagined myself doing — heck, I’d never imagined anyone else doing them either — and I was kinda having the time of my life, despite myself.

I was starting to worry about one thing though.

I was worried one week at Kāhea wasn’t going to be enough.


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