Boys will be Boys
© Broken Boundaries Gay Erotica
After saying the only thing I thought I could possibly say in response to Connor’s declaration that the boys wanted to use me as their experimental sex toy, I could feel five sets of eyes fixed on me from across the round table we sat at. Suddenly the vacation took on a different air: less sublime and more primal. Of course, I was excited at the thought of seeing my friends naked again, touching their bodies, tasting their dicks, but I was also nervous about the idea of spending an entire week serving as their plaything.
It wasn’t like I had much choice in the matter. We were here, on an isolated Hawaiian island, at a resort that was even more isolated, no other communities or people in sight, only one road to access the place. The boys had paid all my expenses anyways, so it’s not like I could afford to leave, even if there were options besides the chartered SUV and private jet we’d flown in on.
As I looked around the table and scanned the faces of the boys, men almost, but still boys, that I’d known throughout high school, I couldn’t help but feel pangs of lust course through my body that began to override any currents of common sense or doubt that may still have lingered in my mind. These guys were hot a-f, even hotter than when I’d last seen them before they went away to their expensive out-of-town colleges. I hadn’t so much as tasted a dick since Bryson had me on my knees two days before he went off to university so he “wouldn’t get too sensitive from blowjobs,” and “bust a nut too quickly in those college bitches’ mouths”.
I wasn’t sure if his logic rang true, but I was happy enough to oblige. Since then it had been a dry spell for over 8 months. I hadn’t even seen the guys when they came back for the holidays, which was why I was extra surprised to be invited along on this vacation. It was starting to make a lot more sense now…
Before I could open my mouth again, Connor spoke.
“Whoa there, gay boy. We’re all glad you’re so eager and everything..”
“Nahhh,” came Bryson’s response, eliciting a round of laughter from the boys.
Connor shot Bryson an amused look and then continued.
“So yeah, as I was saying, it’s great that you’re with this shit, but this isn’t going to be like it was in high school… just blow jobs… a gay dude helping his straight bros cuz he was gay…”
I started to get excited. Fucking. Connor was definitely talking about fucking. They wanted to take my anal cherry and I was over the moon. I was a bit confused about the way Connor was describing it but, straight boys, right?
He went on and it became clearer what exactly he meant.
“I told you our parents wouldn’t let us bring any girls on this trip. Didn’t want any… accidents, girls to pay off, ridiculous shit we’d never get into but they didn’t trust us I guess?”
Grant piped in, “Like I want to deal with a fucking kid now! Slap it, wrap it, then tap it!”
The looks on the boys’ faces clearly reflected the disappointment in their parents’ decision, but I probably still had a shit-eating grin on my face at that point.
Connor’s monologue resumed.
“But there was no way we were gonna spend an entire week at this fire resort without some kind of hole to nut into.”
My cock was hard now, yup, all five inches were straining at my swim trunks, trying to punch a hole through the way-too-thin material.
“Not a fucking chance,” Aiden agreed. “This is our time!”
Another murmur of agreement before Connor carried on.
“So that’s when we thought of you. It was Tyler’s idea really.”
Tyler beamed.
“We knew you liked our dicks, we knew you wouldn’t pass up the chance to go on a lux vacation like this with us and..” he paused for dramatic effect, “We knew once we were here, you’d pretty much have to go along with whatever we said.”
What did that mean exactly? I’d always sucked their dicks willingly in high school, why did Connor need to put it that way? Did they think I was going to refuse anal sex because I was a virgin? I definitely wasn’t.
I decided to allay any fears about my hesitance and spoke up for the first time since Connor had started his speech.
“You don’t have to worry guys. I’m totally down to let you all fuck me if you’re worried about that. I know how big you all are, but I won’t complain!”
I ended the last sentence with what I thought was a devilish, sexy smirk aimed around the table.
My comments were met with silent stares. Maybe looks of amusement?
Connor went on.
“Oh it’s not like that gay boy,”
Gay boy again — not Tommy. It had always been Tommy in high school, even when his cock had been nearly eight-and-a-half inches down my throat.
“We’ll definitely be fucking your ass, no doubt about that, but we want more from you this week.
Grant chipped in again, “A lot more.”
Suddenly my old friends looked a little less friendly, and a bit more menacing.
Connor carried on with his explanation.
“We all uh.. figured out some stuff about ourselves this year. What we like, what we don’t like. We got to try things out, but also didn’t get to try out a lot of the stuff we saw in porn that college girls were too afraid to go for.”
The boys’ eyes seemed darker than I’d ever seen them before. More intense. Focused on me with an interest I’d never experienced before. Definitely not desire, not even hunger, I couldn’t quite place it, but as Connor continued, their stares felt predatory and I wasn’t sure if I liked it or not.
“I mean Tyler found a unhinged chick who would lick his feet for him on the regular, of course, but the rest of us had more mixed results.” Connor ran his hand through his hair as if to deflect from the small show of vulnerability he’d just made.
“There were tons of girls at bars and in the dorms who said they were freaks, but ask them to beg to suck your cock and they’re all like… oh my god, I’m not gonna do that.. and they’re out the door.”
Aiden threw a look at Connor that clearly indicated Connor’s words had struck a nerve. Connor gave Aiden a confident, knowing look before proceeding.
“Since we have you here though, there isn’t going to be any of that no, shit. Well, you can say no, but, if you do, your week will consist of an extended stay in your villa, while we party, so you can think about the mistake you made when you refused our offer. If you make the right choice, and say yes, you’ll be spending the week doing as we say, especially the things those prudes at school wouldn’t do and you’ll do it without hesitation or objection. You’ll also do it to the best of your ability.”
Connor clearly had more to say, but he gave me a moment to digest everything he’d just said, and he’d said a lot.
The dining room of the Kahe‘a Resort was lush and elegant, but it offered no respite. The walls were paneled in dark, tropical hardwood and broken up by tall archways that let in streaks of late-afternoon light. Overhead, woven pendant lamps hung like upside-down baskets, glowing soft and gold above our round dining table. I looked around for an escape but there was nowhere to go.
I spoke again, trying to regain some control of the situation.
“Look, I guess I understand what you’re saying and—” I paused, “and I think I can make what you’re talking about work. I guess, I just wanna know what exactly we’re talking about? Foot stuff it sounds like, but what else specifically?”
Tyler spoke up this time, shutting down my question quickly.
“That’s for us to know, and you to find out fuck boy.” He giggled at his new name for me.
My cheeks smoldered red with humiliation. I had no control over this situation and the boys were making that very clear to me, very fast.
Connor, who’d clearly plotted the course of this conversation out well ahead of time, started in again.
“We want to get our vacation started A.S.A.P. so you need to make your decision now, Tommy. Are you going to spend the week in your villa, while we party and rip this place up or are you gonna take the place of the bitches we couldn’t bring here and be our bitch for the week?”
My stomach seized as Connor spoke those last words. What I’d thought was going to be a chilled vacation with my old high school friends — and maybe a little bit of sucking their cocks — had turned into me being their full on “bitch” for the entire week, or else spend the week as a virtual prisoner in my villa. Granted, it was the nicest hotel room I’d ever stayed in, in my life, and I was sure they’d feed me and everything, but spending an entire week there while I knew they were out in the resort partying without me would be torture.
At least if I agreed to their terms, I could spend some time with my old friends, party with them, be one of the boys — sort of. It wasn’t as if I’d been their equal for a long time anyways, so I could live with this, couldn’t I? It was just a slightly new element to their fun. They wanted to call me their bitch and have me perform a few new tricks. I could handle that!
My cock started to harden in my swim trunks again as the thought of whatever these boys had planned for me settled into my college-boy brain and I already started to think about the intense jerk off sessions I’d have each night after I’d entertained my high school buddies during the day. Ok, this might not be so bad after all. It was time to agree to their terms.
“I’ll do it.” I said.
“You’ll do what?” Tyler queried.
“I’ll—” I stuttered, not sure what he was looking for exactly.
Tyler helped me out, “You’ll be our…”
Now I knew what he wanted. My cheeks turned red again.
“I’ll be your bitch.” I admitted.
“For the entire week?” Grant asked.
“For the entire week.” I replied.
“Good boy” Aiden said.
The others all laughed at that. If my face could have turned any redder at that moment, it would have.
Connor addressed me again, delivering the final blow.
“You made the right decision. Not sure what you woulda done in that room by yourself all week; not that it woulda been my problem. There will be some rules for you that we’ll explain later, but for now we gotta get ready for this week. We all have keys to your room, by the way, so we can pop in whenever we want, don’t be surprised.”
Special rules for me for the week? They all had keys to my room and could walk in whenever they wanted? This was starting to get a little out of hand. What had I just agreed to? How was I going to enjoy those sweet, sweet fap sessions if my high school buddies could just walk in on me anytime they wanted? How embarrassing would that be? Even if I was spending the week taking their dicks in my mouth and ass?
Especially then.
Of course, Connor wasn’t quite finished.
“Alright bros, it’s night one and we have a week of dope partying ahead of us. We gotta get this place set up for our epicness. Let’s go back to our Villas and get changed for the night. Gay boy, I think Grant has some special gifts for you too before we go.”
Grant looked at me like a kid on Christmas morning as he retrieved a small, tan, canvas tote bag he’d been stowing under the table during dinner. It seemed heavy, although there didn’t seem to be very much in it. Grant handed me the bag, still grinning like he’d consumed a little too much alcohol.
“These,” he said, “are for you.” As he plunked the bag into my lap.
“We didn’t know your size so we ordered a whole bunch. The lady from the website says you should choose one that leaves no room for your dick at all. Like, squishes it back a bit, she said.”
What – the – fuck did he mean?
“Huh?” Was the most intelligent response I could muster.
Bryson swooped in to my rescue.
“They’re chastity cages. We want you locked up for the week. You used to get hard when you sucked our cocks like ALL the time and it was kinda gross for us.. no offence or whatever.. But just like.. seeing your little dick all hard while you went to town on us, it took us out of the scene. The cage will prevent that.. or at least keep your dick from poking up where we can see it.”
I was stunned. They wanted me to lock my cock in a cage. For the entire week.
Was this some kind of joke?
I looked inside the bag.
Nope; not a joke.
And why the fuck was Grant so excited about this? Was this one of his little kinks?
This week was getting more and more complicated, but the alternative was still a solitary week in a big lonely villa by myself with my thoughts. Connor hadn’t been wrong either. I would definitely be thinking about how badly I wanted to taste their big, teenage dicks, and finally lose my anal virginity to one of them if I didn’t go along with this — whatever it entailed.
Grant looked me up and down as I closed the tote bag up again, then, with a little too much excitement in his voice he said, “You all good with those? Make sure you pick one with no extra room to grow.”
He looked at me, practically giddy. I looked at him, trying not to throw any shade, trying even to retain an aura of gratitude.
“Got it?” He prompted.
Dear god, he expected an answer from me.
“Yeah,” I said, “I got you.”
“Good boy,” He said, petting me on the head for effect.
The boys laughed at the gesture. I felt the heat creep up my neck, but kept my mouth shut.
I thought things couldn’t get any more humiliating, but Connor would add one more indignity to the evening.
“Alright, boys,” he said. “Let’s all go get changed for the night. That includes you, Tommy.”
I bristled.
“It’s pretty warm here even at night though, so the only thing you’ll need to wear tonight, and for the rest of the week, is whichever cage you pick from that bag. See you in thirty, boys!”
The guys got up and started to file out of the room, Bryson, Tyler and Grant all still grinning at me like they bore a secret I still wasn’t privy to — maybe they did.
Aiden gave me a strong slap to the shoulder as he walked by. Was it friendly or some kind of mind fuck? I couldn’t tell at this point.
When all of the boys had left and I was by myself in the dining hall, still sitting in my chair, only one thought spun through my head:
THE FUCK!?
Had they just told me that in addition to everything else they expected: the sexual service, my room being theirs to barge in on, the chastity cage, I was also going to be spending the entire week walking around naked?
What about the staff? Sure they were basically nowhere to be seen, but surely we’d bump into some of them at some point.
What about my decency and self respect?
Would I constantly be throwing wood, even in the cage, because of my constant denial and the presence of all my hot friends, giving them a reason to tease me?
I didn’t have much time to linger with my thoughts because Connor came back, banging at the dining room door and threw me a gesture that indicated I had better get going to my villa.
I didn’t think twice.
I got up and headed toward my villa to change into my new ‘outfit’.
My cock was still hard, and now, it seemed to be making the decisions for me.
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Broken Boundaries Gay Erotica
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