The Straight Boys Took Me On Vacation

I'm Tommy, 18 year old college freshman on a vacation with my 5 rich, str8 friends. They've paid to rent the entire place to ourselves but with no girls allowed, they've tasked me to be their bitch for the week playing out all of their kinky fantasies. When rain ruins the plans for the evening I become the night's entertainment.

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Private Screenings

© Broken Boundaries Gay Erotica

The rest of the afternoon passed without much incident. The boys eased their muscles in the ice pools, excited to test out the new-age contraptions, videoing each other “taking the plunge”.

We went to the beach cabanas next and hit the alcohol pretty hard. It was day three and everyone was getting pretty comfortable with the easy access to alcohol. It wasn’t technically legal for us to drink here, but we were legal back home and for the price our parents had paid, the staff were happy to turn a blind eye.

If it weren’t for my perpetual nudity and the metal enclosure around my cock, it almost could have passed for a normal afternoon.

‘Almost’ because at one point on the beach, Tyler and Aiden, in a very drunken state, decided to compete as to who could do better Tommy impressions from the night before. They had the group in stitches as they tried to outdo each other making strangled moaning noises and ridiculous grunting noises. Not to mention misquoting me in ways that made me sound like the neediest slut you’d ever met.  

“urrrrgghhhh ummmph!” Tyler cackled.

“No, it was more like, aaahhhffff oohhmmm,” Aiden would spit out in response.

I was just glad they didn’t ask me to weigh in by joining in on the performance.

As dinner approached, I could sense a shift in the mood. The alcohol had really begun to work its spell, and the boys were hyped up. I was too.

We descended on the dining room like a pack of hungry wolves.

Dinner was as spectacular as ever. I didn’t know where to look or reach first. No one had told me to take it easy on the food this time, so I guessed they didn’t have a five-way anal experience planned for me this evening. Not that I would have minded, but I was going to take advantage of the dining opportunities while I was here, if I could.

With dinner behind us, we had planned to head to the pool and continue the binge on alcohol, albeit at a slowed pace, but rain collapsed our plans. We decided on a movie instead. The hotel had access to all the major streaming services, and the movie room was just as luxurious as the rest of the place.

We packed in a few bottles of our favourite drinks and set up to watch the latest Marvel release on streaming. Another dumpster fire, but we’d consumed enough booze for it not to matter.

Somewhere mid-way through the film, I felt a nudge on my shoulder, it was Aiden. He motioned for me to follow him and we quietly exited the dark movie screening room.

Once in the hallway he looked side to side as though he were checking for traffic. Once satisfied, he started to undo his shorts and pulled out his flaccid, five-inch cock. He put one hand on my left shoulder, applying enough force to leave no doubt as to what he wanted.

In a flash I was on my knees, ready to do whatever he had in mind.

Aiden pressed his soft cock to my lips then spoke.

“You did such a good job drinking my piss earlier, boy. It was every bit the fucking rush I thought it would be. You ready for another taste?”

I nodded.

“Good,” Aiden said. “Because I drank a lot of beer today, and I’ve really gotta go.” He laughed.

He pushed the tip of his cock between my lips and I felt the stream surge almost immediately.

The taste was different this time. Less concentrated than this morning. With all the beer he’d been drinking it kind of made sense that his piss would be more watery. It made the second experience easier than the first. I was almost able to enjoy the act this time. Not so much the taste or even the feel of it. Just the fact that I had Aiden’s cock in my mouth and the knowledge that I was pleasing him and making him happy, even if I was accomplishing that by doing something so nasty.

My cock rose to the occasion. It never seemed to miss a beat anymore. I wasn’t sure if I wanted Aiden to notice or not. If he did, he might take the opportunity to tease me, but at least he’d know I was turned on by him.

What strange thoughts to be having while you kneel drinking another guy’s piss.

Aiden’s stream may not have tasted very strong, but it was a long and relentless one. He wasn’t lying about how much beer he’d drank, and apparently, he hadn’t emptied his bladder all afternoon. At least it certainly seemed like I was taking it all. His piss kept coming and coming in torrents, and I swallowed without fail, impressing myself more than Aiden apparently.

It was like my throat adapted to the experience and did what was necessary to ensure I didn’t drown on the volume Aiden was giving me — or make an embarrassing mess of the hotel floor.

After what seemed like minutes, but was probably no more than forty-five seconds, Aiden’s stream started to die down, then finally cut off to a few drops. He made sure I got every last one.

“Thanks, boy; I needed that,” he said. “You did a real good job. Definitely do that again this week.”

At least he thanked me I giggled to myself in my drunken state.

He pulled up his shorts and underwear and we both returned to the movie room. Aiden with an emptied bladder, me with a fuller one and a mouth you wouldn’t want to kiss.

It seemed the others got ideas from Aiden because it wasn’t more than fifteen minutes before I felt another poke on my shoulder. This time it was Tyler. I got up without thinking and followed him out of the room.

Tyler didn’t stay in the hallway outside the screening room though. He had me follow him to the cigar room nearby. I would learn why in short order.

As we walked in, Tyler followed much the same protocol as Aiden had, shucking off his pants and then pushing me expectantly to the ground. Within seconds, his cock was at my lips, but Tyler didn’t want to pee in my mouth, he wanted me to get his dick hard.

“Suck,” was all he said.

I was happy to oblige. Tyler’s dick was better than that movie any day.

The head of his shaft slipped between my lips and as if echoing the thoughts in my head Tyler said: “That movie was pretty bad. Figured I’d do something more productive.”

I’m not sure if it was the alcohol, the chastity cage, or the transformation that had occurred over the last three days at Kāhea but I shocked myself again with the words I spoke next.

Like some kind of besotted twink in a porn film, the filth just poured out of my mouth. I pulled back just long enough to say:

“Oh fuck yeah, it was so bad. Use me hard, Daddy”

Daddy? Where did that even come from. Internally, I committed myself to never using that word again, but Tyler seemed to love it. Or maybe it was just the ‘use me hard’ part. Either way, it was like a fire ignited in him. I felt his hand clutch the back of my hair and his dick was immediately back in my mouth, hardening quickly now.

Tyler’s cock stiffened fast in my mouth, like it had just been waiting for the excuse. His hand knotted harder into my hair, and his laugh came low, sloppy from the booze.

“‘Use me hard, Daddy.’” He slurred it back at me like a taunt, pushing my head down until his shaft jammed halfway into my throat. “Fuck, Tommy, you know exactly how to get me going.”

I gagged, coughed, spit stringing off my lips, but he didn’t give me a break. He yanked me right back down, rutting against the back of my throat like he was trying to erase the bad Marvel movie out of his brain with each thrust.

“You asked for it rough,” Tyler said, voice sharp even through the drunk edges. “So don’t start crying on me now.”

I wasn’t going to cry, but the brute force fucking of my throat definitely had tears spilling down my face. He had me pinned tight, spit bubbling around his shaft as he used my mouth like a hole in the couch cushions.

He pulled me off with a wet pop and spit down right onto my tongue. It was fast, mean, sloppy. I swallowed because I had no other choice. His grin spread wide.

“Good boy. You take shots of spit like they were shots of tequila now.” He tapped his cock across my cheek, three sharp slaps, then shoved it back between my lips. “C’mon, suck. Earn that fancy dinner you just ate.”

I did, gag reflex already raw, spit soaking my chin and dripping down my chest as I bobbed on him. Every time I tried to steady the rhythm, Tyler pushed harder, hips snapping, his drunk laugh spilling out like it was the funniest thing he’d ever seen.

“Look at you—fuckin’ dripping, mouth wide open for me. All cuz you said the magic word. Rough. That’s all I needed, Tentpole.”

He let go of my hair suddenly, shoved me back by the forehead. I landed on my ass with a grunt, still coughing up spit. Tyler grabbed his own cock and stroked it twice, smearing my spit over the head, then leaned down, slapped my face with it again, harder.

“Get up.”

I scrambled, legs shaky. He spun me around and pushed me chest-first into one of those ridiculous, oversized leather couches. The kind that probably cost more than my bursary had been worth in a year. Soft, supple, expensive. This was obviously the reason he’d chosen the cigar room. I barely had time to register the feel before Tyler was kicking my legs apart and climbing up behind me.

He spat again — right on my lower back — and rubbed it down into the crack of my ass with the heel of his hand. Not prep, just marking territory.

“You ready for this, cage boy? Gonna give me that hole and let me ride you rough, like you promised?”

“Yes, Sir,” I managed, cheek pressed against the leather, already damp with my breath.

Tyler laughed, slapping my ass once with his palm. “That’s the spirit. You begged for it. So now you’re gonna get it.”

He spit on his cock, spit on me, then lined himself up. One quick shove and he was inside, stretching me raw and fast. I yelped into the couch cushion, leather muffling the sound.

“Yeahhh,” Tyler groaned. “That’s what I’m talking about. Fuck, you’re tight. Should’ve bent you over one of these couches on the first night.”

His hips smacked against my ass as he bottomed out, one hand gripping my shoulder, the other smacking across my asscheek in a drunken rhythm.

“Say it again,” he demanded.

“Say what?” I choked out, breath gone.

“That you wanted it rough.” Another spank, harder this time, echoing in the room.

“I— I wanted it rough, Sir!”

“Louder!”

“I wanted it rough!”

He thrust hard enough to shove me deeper into the cushions, the leather squeaking under the pressure. His laugh was wild. “That’s my bitch. Ask for it, get it. Simple math.”

Each slap of his hips drove the cage against me, a sharp reminder that no matter how turned on I was, I wasn’t getting release. Tyler loved it. He leaned over my back, voice hot against my ear.

“You’re leaking in that little tin prison, aren’t you? Can feel it when I slam into you. All that pressure and nowhere for it to go. Bet it hurts. Bet you fucking love it.”

He spanked me again, this time lower, right where my thigh met my ass. I jolted, whimpering, and he howled with laughter.

“Yeah, right there. Sensitive as fuck. You’re a goddamn mess, Tommy. Drunk, naked, caged, bent over a couch—probably worth more than your car—and still begging for it harder.”

His thrusts turned brutal, shallow and quick, each one knocking the air out of me. The couch groaned under us. I clawed at the leather, trying not to slip. My cheek stuck to the cushion with spit and sweat.

“Talk to me, boy,” Tyler demanded. “Tell me you love it. Tell me you’re glad you asked.”

“I love it!” I gasped. “I’m glad I asked, Sir!”

“Fuck yeah you are.” He spat down onto my back again, let it roll over my spine. “Good little cockslut. Best decision of your life, letting me wreck your ass tonight.”

The spanks kept coming, left cheek, right cheek, thighs, each one stinging worse with the alcohol heat radiating through both of us. My ass burned, my throat raw from earlier, but the humiliation made me buzz with something I couldn’t fight.

Tyler pulled almost all the way out, slapped his cock against my hole twice, then slammed back in. I cried out, forehead knocking the couch armrest. He didn’t care.

“You asked for it rough,” he repeated, panting now. “So don’t you dare think about tapping out. Not when I’m balls-deep in you on hotel furniture.”

“I—I’m not…” I reassured Tyler. As if he needed any reassuring.

His cock dragged against my walls, thick, unrelenting. He leaned back, smacked my ass again, and I knew I’d be bruised tomorrow.

“God, you’re taking it so good,” he muttered. “Didn’t think you had it in you. But here you are—begging, caged, dripping all over Kāhea’s finest leather.”

I moaned, biting down on the cushion. The leather taste filled my mouth, bitter, sharp. Tyler caught it, shoved two fingers into my hair, yanked my head back.

“Don’t you hide that noise,” he growled. “Let ‘em hear it down the hall if they’re listening. Let ‘em know you wanted it like this.”

My voice broke on the next cry, loud and pathetic. Tyler’s laughter turned guttural. He was close.

“You’re gonna make me cum so fucking hard, boy. And when I do, you’re gonna thank me for using you just the way you begged.”

“Yes, Sir,” I gasped.

He hammered into me, rougher, faster, spanking between thrusts until my ass felt like it was on fire. His breath hitched, body jerking against mine.

“Here it is,” he hissed, shoving deep one last time. His cock pulsed, thick streams bursting inside me. He held me there, pressed to the couch, both of us shaking, his laughter bubbling out like he couldn’t stop.

“Goddamn,” he breathed, finally pulling out. His cum dribbled down my thighs, hot against my skin. He smacked my ass one last time, lighter now. “That’s what you get for asking. Best fuck of your life, no contest.”

I collapsed against the couch, body wrecked, face stuck to the slick leather. Tyler pulled his shorts back on, still laughing, drunk and glowing.

“Clean yourself up, cage boy,” he said, grabbing the bottle of whiskey he’d brought in with him. “I’m telling the guys you’re finally learning how to party.”

And just like that, he was gone, swagger echoing down the hallway, leaving me bent over a couch that smelled like leather and cum, aching and used exactly the way I’d asked.

I could feel his cum dripping out my hole and starting to leak down my leg. There was no denying it, I’d leapt another rung lower on the totem pole today and both times I’d begged for it to happen.

There was no doubt I was becoming something different, or maybe what I was always meant to be. That didn’t really concern me. What was starting to really worry me was how I was going to fulfill all of these new desires once we got home from the resort. The boys would have girls again and I’d be back to square one.

I’d just taken cock in both ends and I was already plotting how I’d be getting more… Oh Tommy…


This story is currently in its 30th chapter.


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