Chapter 3: Dorm 1043

When he put the bottle back and spun, it landed on Sawyer.

"Tell us the truth Sawyer, why'd the councilors trap you in a room with a bunch of 18-year-olds instead of giving you one of the Junior private dorms."

Sawyer shook his head, and then not surprising any of us one bit, he went ahead and stripped out of his shorts AND his underwear. For good measure he also took a pull from the bottle.

Marcos smacked his brother playfully around the head when Luca WOULD NOT stop staring at Sawyers perfectly gigantic flaccid penis.

The next spin landed the bottle on me; I felt myself starting to sweat under the pressure.

"Show me that butt plug." Sawyer said; I pawed behind my back until I found it and then I brought the rubbery toy out into the open. "Can you actually fit that thing inside of your ass?" He asked; he wasn't joking or teasing.

Shit. Either I don't answer, which would make them think either A: I could fit the plug inside my ass. Or B: I was too much of a pussy to be able to fit the plug inside of my ass. Otherwise, I had to drink or strip. Apparently, like Sawyer, you could do both -- but he was 100% just making up whatever rules sounded fun to him in the moment. Stripping sounded a little bit risky and also a little fun to be honest; they hadn't seen any of my other tattoos yet... but I knew I had to answer the question.

"I've... never actually used one of those." I gestured at the sex toy, "This morning... this morning I stole it from some kid's locker after showering."

Finn looked disappointed, the expression hurting me a little. Meanwhile Luca just nodded while Marcos whistled appreciatively.

"That's... that's kind of a bad thing, right?" Isaac asked.

Laying a gentle hand on Isaac's knee Moss said, "Its not okay that Alastair stole from another student, 'no', but whatever we share tonight stays between the 7 of us."

We all agreed.

Glad to get that over with, my spin landed between the twins, not on either one of them specifically.

"Ask them both a question." Finn suggested excitedly.

"Luca," I asked, "Have you and Marcos ever... masturbated together?"

He took off his shirt and tossed it on one of the bunks, glaring at me. Tanned and flat with the mild beginnings of definition and a little black happy trail, Luca's chest and stomach were good looking, with a cute little innie bellybutton.

"Marcos," I asked, "Have you ever fucked a girl in your childhood bed?"

Marcos grinned, "Yes, and heavy-sleeper here," he grabbed his brother around the middle, "didn't even wake up with me plowing her next to him."

I was a little disappointed to find out that he was straight. Or maybe bi? But the thought of Marcos having sex next to his sleeping brother... that and Sawyer just sitting there openly nude... okay, I wasn't the only boy starting to get a boner.

"Sorry." Said Isaac lamely, drawing way too much attention to the little tent in his pants.

The twins spun the bottle together since they'd both been asked a question by me. Unfortunately, the liquor landed on antsy little Isaac. He flinched, but Moss patted him again on the leg with a comforting hand and he perked up a little after that.

"Alright Isaac, we're both gonna ask you some hard ones, ready?" Luca spoke first fortunately, seeing as he was the more reserved and probably nicer of the twins.

"I'm ready." Isaac said.

"What's the weirdest porn you've ever watched?" Marcos barreled ahead, clearly missing the fact that Isaac was so nervous.

"Uhmmm..." Isaac stalled; the bulge in his shorts twitched visibly; I tried catching Finn's eye and he smiled knowingly at me. Instead of answering, Isaac tried to take off his sweater and ended up getting stuck head and arms inside of the thing; when Moss jumped in to help him, the entire sweater and top shirt pulled off of Isaac.

If possible, his blush was full face red clear down to his chest. He had a tiny alabaster figure and hard little nipples -- I wouldn't say he was unattractive, he was, it was just attractiveness in a very youthful innocent virginal kind of way. I mean... most of us were probably still virgins, right? But Isaac was clearly virgin multiplied by 12. Surprisingly he had a skinny-person four pack raising the front of his stomach. He had no chest hair to speak of.

"You... you have cum before... right?" Luca asked more gently, getting his question in.

"Uhhhm...." Isaac said again, "Just... just twice now... it... it was great."

Okay, it was endearing how honest this kid was. Yeah, I knew he was 18 also, but it was hard to think of him that way.

And just TWICE? I was only 18 too... but I couldn't even remember how many times I'd cum by now. Since the age of 12? Way way way too many times to count.

By the time the bottle had spun around 11 or 12 more spins, we'd each taken a turn at being more daring or answering something a little more honestly. I took a swig from the bottle and DID NOT like the burning taste. Finn ended up losing both his shirt and then his shorts, making him nearly butt naked yet still looking really good in just his white skintight athletic boxers; the groove of his growing cock was easy to see in them.

Oh also, I didn't miss the fact that he chose to take off his shorts rather than answer Sawyers question, "Have you ever tried fingering yourself."

We all knew stripping was just a vague 'yes' answer.

Marcos and Moss kept drinking and not answering till they were just laughing and laughing and it was clear they weren't paying much attention to the game anymore. Sawyer somehow managed to stay in his shirt and actually answer some truths; Luca teased all of us by first taking off both his basketball shorts and underwear, revealing for a few glorious seconds his rock-hard cock covered in curly brown hair, and then quickly popping the shorts back over his hard-on.

I wasn't too mad; I still had a good view of his girth by looking up the inside of his loose pant leg. Honestly, the struggle was not cumming with all this going on. Finn and I met eyes a lot during the game, and though I'd known him only a little while, I could tell he was thinking a similar thing.

Based on his questions and his answers, I could tell Finn was just as curious and exploratory as I was -- or at least, how I'd been lately.

At some point -- looking like they felt a little uncomfortable, but not disinterested because they kept watching -- Marcos and Moss left the game with small glasses of the booze and sat on a top bunk together following what we were doing below. That left just me, Luca, Sawyer, Finn, and Isaac.

The next question -- "What did you do to get sent here? -- made me lose my underpants; they could all clearly see my dripping precum. I was NOT going to tell them about my arrest record though.

"That's a gorgeous tattoo." Luca ran a hand nervously through his brown bangs, revealing a pretty pair of blue eyes studded with a middle line of brown. Without asking, he reached a hand out and trailed it through my pubic hair and up along my backside to my spine. His touch was warm and it made me shudder; no one else seemed to mind what he was doing, "La serpiente." Luca breathed in Spanish. A line of my precum dripped down to where his fingers had just touched.

Finn had leaned closer to the two of us and without asking anyone's permission, or without any clear shame, he was touching his cock a little bit, clearly liking what Luca was doing to me.

"T-thanks." I stuttered nervously.

The attention was stolen away from me by Sawyer -- almost laughably -- crawling over to the bottle and using his hard schlong to spin it. By the way, that dick rock hard? It was 9 or 10 inches and tree branch thick on the hairy boy. The bottle glittered with a little of Sawyers pre-fluid and it stopped on Isaac.

Isaac was still in pants and underwear, just missing his top shirt. He'd taken two swigs of the bottle by this point and answered most of his questions. More comfortable with us, or maybe a little drunk, his thin blond eyebrows were raised curiously and he would periodically forget we could see him and run the tip of his hand ferociously over the top of his penis through the layers of clothing. He'd squirm a little too. Horny kid!

Fuck! I was starting to like this group. They were all so bold and fun to be around. I almost felt bad about being such a hard ass so far.

"I dare you to put the butt plug up your ass Isaac." Sawyer ordered.

"You're allowed to ask questions, not dares!" Finn reminded him, laughing.

However, surprising all of us, including Moss and Marcos who straightened up a bit in their bunks, the small skinny boy reached toward where the toy lay near me and he pulled it over to himself.

"You're not fully naked Isaac." Finn told him, patting the kid on the back, "You DON'T have to put the toy in your ass."

"That's okay. I... I want to try it..." Isaac answered him boldly.

Luca's grip tightened on my backside as we all turned our attention on Isaac.

"Is... is it okay if I don't... I'm not sure I want to take my clothes all the way off." Isaac stuttered awkwardly.

"Totally fine big man." Sawyer sounded WAY too encouraging and interested, "Anybody got lube?"

It was such a turn on when my bunk mate, Finn, got up and crossed between Luca and I and then came back with a bottle of KY.

After Moss mocked the bottle for a second -- apparently there was much better lube you could get -- no one else had any offers and Finn set the bottle next to the plug and in front of Isaac.

"I've... never done this before to be honest."

"Don't worry Isaac," Finn smiled, "I think it will feel really good... just go slow." When Isaac continued hesitating Finn added, "Here, I'll show you where to start buddy."

Finn leaned back against the closest bunk and slipped out of his tight boxers, passing them with difficulty over his 6 or 7 incher and flushing with some residual embarrassment. He didn't stop though -- damn this guy was brave. Lifting his legs up and grabbing the bottle of KY he spread some glistening lube over his right pointer finger and probed gently at his butt hole.

Luca stripped down fully and then extended a leg around me and slid along the carpet until he was slightly behind, legs cupping my legs. I tensed with pleasure as Luca's boner rubbed against the back of my ass. He kept watching Finn over my left shoulder and I could feel the twin's hot breath along my ear. Pushing back into him on purpose, I felt the fit guy reach down and cup a single one of my ass cheeks.

"You can start like this Isaac, just use the toy like I'm using my finger and tease the opening of your hole for a little bit."

Isaac nodded and rubbed lube into the toy, then he stretched out the back of his sweatpants and the tight band of the... I leaned up to look, yup, kid was wearing tighty-whities... he lower the butt plug past them and out of sight.

Eyes clearly widening in panic as he found the spot, Isaac looked to Finn for guidance.

"Don't worry buddy." Finn encouraged, eyes never leaving Isaacs, "I've been doing this in the showers every morning and I'm really starting to figure it out. Apply a little pressure with the toy, just like my finger is doing." He demonstrated.

Finn's ass opened greedily around the finger and then closed tight; small ass hairs curling where it puckered around him.

"You don't have to fit it all in right away. Go ahead and get comfortable Isaac, your ass can get used to the feeling."

When Isaac gasped we all figured that he must have managed to push the tip of the plug in. His eyes were wide as saucers but he got a big grin of pride on his face.

"You're so hot Isaac." Sawyer half-said, half-moaned, eyes glued on the scrawny arms holding the toy into place.

"Its... its really tight." Isaac breathed.

"A little at a time." Finn grinned, "How's it feel."

"I... I don't know... a little weird. I'm... I really really want to cum..."

"Me too." Luca whispered in my ear, both of us watching the show between Finn with his legs more and more spread and Isaac's wide-eyed face and pushing back slightly into his hand and the toy clutched there. A wet spot started on my back; the tip of Luca's baby-maker tracing its anticipation all over me.

"Okay, now go a little deeper. The middle part will be the biggest bit." Finn grunted and added a second finger to the first, grinning really widely and making eye contact with each of his friends watching. Sawyer was stroking his dick slowly to the scene, and maybe because I wasn't touching mine, Luca reached around and 'gave me a hand'.

I'd never had another guy touch my penis before. His young hands were smooth but strong and at first he just cupped my cock tightly in his grip.

Face red and sweat running down the sides of his arms and down his forehead, Isaac grunted loudly and struggled with the plug in his hand.

"I don't think it will fit." He complained.

"You have to relax." Sawyer told him.

"Like me." Said Finn, pushing his fingers in up to both knuckles and then showing us how he relaxed his opening ass hole around them.

"Does that feel good?" I asked, unable to stop myself.

Finns eyes found mine and he nodded through his arousal, "When the pressure hits my prostate... Alastair, I almost cum so quickly."

I liked the way he said my name. I also liked the way Luca was gyrating his hips and his throbbing cock against my backside. The twin lowered his smooth chin onto my shoulder, lips breathing warm air against the inside of my neck while we watched Isaac breathe first once and then again and then he SIGHED loudly.

It was clear the moment the anal plugged suctioned into place, retracting fully inside of Isaac.

He caught his breath and then he leaned up on his knees panting really heavy and trembling.

"I... I... I..." he stuttered, "I'm cumming. I'm... c-cumming."

Still tenting his pants and without any delay his little penis started pulsing out of sight. It only pulsed once or twice before it was done, leaving him panting and trembling. Isaac looked so embarrassed, but like always Finn was already there to help the nervous nerdy boy.

"It's okay. It felt good, didn't it?" Finn asked, leaning over Isaac.

He nodded and grinned.

"You okay if I help you take these off?" Finn asked, gesturing to the rest of Isaac's clothes.

Isaac shook his head vigorously.

"Look," Said Finn, "You've got nothing to be embarrassed about. We're your friends and we won't make fun of you, but I think we all do want to see you with that butt plug in your ass... is that okay?"

"Y... yes." He accepted.

Luca played with the tip of my penis while we watched Finn pull Isaac out of the soiled pants, revealing the cum-dripping tighty-whities and then helping the boy out of those as well. Isaacs cock was already going flaccid, maybe 3 or 4 inches long and covered with his young boy mess. Sawyer spat loudly into his own hand and using the spit he started going to town on his gigantic hairy chub, totally entranced by the sight of Isaac.

I had to admit, so was I.

"Turn around." Finn told him, "You okay if the rest of us... cum on top of your back and ass cheeks?"

Isaac grinned and nodded.

"You guys got a problem with that?" Finn asked the two boys still dressed and watching from their bunks.

Marcos nodded that he was fine, smiling.

"We're not prudes." Added Moss.

Sawyer was the first to get behind Isaac as he flipped around, revealing his backside. For a brief moment Sawyer's hairy ass blocked the sight of the butt plug filling the younger boys tight hole, and then Sawyer moaned and shot his load all over, saying 'yes, yes! So hot!" As he made a mess all over.

Once he'd moved though, the ropes of his cum covering the nude back and dripping into Isaac's pushed out butt-crack... well, it perfectly framed the tight hole gripped around the toy.

Luca pulled off of me with a grip of my shoulder, towing me with him and the three of us -- me, Luca, and Finn leaned up shoulder to shoulder around Isaac's turned back. He was braced on the bunk, turning over a shoulder and grinning at the three of us, clearly enjoying what was going on.

"Is this really tight in there?" I asked Isaac, reaching my hand over and starting to jerk Luca off. He moaned a bit at my touch and he in turn grabbed my dick and Finn's dick as well.

"It's really tight."

"I'd like to try it some time." I panted; my pace increasing on Luca's dick. Finn reached to the side and grabbed the lube, pouring a little over all of our hands working a penis; the slick texture and the sureness of Luca's grip had me so close to jizzing all over Isaacs freckly ass with its surprisingly plump cheeks.

Sawyer retreated to his bunk with a contented sigh.

"We're all going to make such a mess on your beautiful asshole." Finn told Isaac, "You're going to need to shower after."

Luca pumped my dick so well, it was clear he'd had practice at this before. He leaned back toward me again and surprised me by running his tongue along my neck.

"Harder than that baby." He ordered, "I want my load to spray up Isaac's back."

I increased my speed, enjoying the feel of him between my fingers, enjoying his moans and grunts of enjoyment.

"That toy looks so good inside of you." Finn moaned.

"We'll have to try something bigger some time." Luca promised.

"We'll have to take turns trying our cocks out." I added.

"See which one you enjoy riding the most." Finn met my eyes as he said it and he was the first of us to cum, joining Sawyers seed on the boys back and painting little trails of it between his ass cheeks and along the flat handle of the plug. Luca kept kissing on my neck and begging for me to go harder on him -- "So close." He was panting, "So close to emptying my balls all over him."

"At the same time." I told Luca in a breathless voice, "I'm close too!"

"I'm gonna... I'm gonna blow so hard." He jerked me off with insane skill and such care, pulling my cock out so just the the tip of me brushed the inside of the cum-dripping ass.

"Don't you fucking move Isaac." I ordered and Finn reached out and steadied the boy to catch our aim.

We came at the same time, like I'd wanted.

Luca's moans of pleasure overlapped my own and my spunk got all over Luca's hand at first and then splattered into the middle of Isaacs plugged-up hole. True to his intentions, Luca nutted all the way up onto Isaacs bare shoulders and even landed some of his load onto Isaac's face, still turned toward us and smiling.

It was better than anything I'd felt before, better than drugs and way better than stealing that car had felt.

Luca and I continued giving our hand jobs to one another until every drop was out; the gorgeous Spanish boy having bitten lightly into the side of my neck once he started cumming. He moaned into my skin and then pulled back.

It really was quite the mess; still four boys naked on the dorm room floor with four gigantic loads dripping from Isaacs backside and his own small wad all over his front.

"That was amazing." Finn sighed, sounding like he'd discovered the secret to the universe or something.

"You said it." Isaac agreed.

And that's when, right at that moment. Right when we were most vulnerable and most spent.

That's when the door to our dorm BANGED open. Some random senior barged in, tall and skinny and pale, in pajamas, wearing glasses like Isaacs. I didn't recognize him, but with a laugh he hefted something bulky and metallic -- the flash was blinding -- "I knew I heard what I heard!" He crooned.

And before the 7 of us could do anything, while we were all still disoriented by the flash, he had run out with PHOTO EVIDENCE of our sexual fantasy spelled out over our hands, the carpets, the clothing strewn about, and Isaac's cum soaked boy hole with its obvious toy inside.