Playing With Dylan

Hope you all had a good weekend! 

It looks like the results for John, This Needs a Part Two! are as follows: 

The Student Auction

The Bigot

The College Cock Sleeve

My Roommate's Sex Slave

These will be the stories this week, and I'm happy to run the poll again very soon in order to get to more of the things that you guys want to see! In the mean time, here's a spicy little one to kickstart you Monday morning! 

All characters are 18+

We were young, naive, stupid, somewhat horny, and all those other things that teenagers are. For the purposes of this story, I’ll call my best friend Dylan, and describe him as a very handsome guy who everybody loved.

I was pretty certain that I was gay at the time, and I was very certain that he wasn’t. Despite that, we had been good friends for years, and spent most weekends at either my house or his, this particular night, we were at his.

Huddled up in his bedroom, we spent most of the evening watching movies, chatting, chilling and the likes, until Dylan had the grand idea to swipe a bottle of his dad’s whiskey, and so began a very interesting evening.

I’ll preface this by saying that neither of us had much experience in the alcohol department, and neither of us were even remotely pleased by the taste of this fiery hell that we were forcing ourselves to drink. Yet, being macho boys, we refused to back down, and continued drinking until the two of us felt that warm buzz of intoxication.

Dylan seemed far drunker than I felt, but I was sure that it was all a gimmick, so when he suggested that we go onto a certain well-known website that was famous for pairing random strangers from around the globe together on video chat, I shrugged.

Queue a torrent of old men jerking off and some other strange behaviours, and we eventually landed on a young couple, who were admittedly quite hot. Naturally, my eyes were on the man, who looked to be in his early twenties, and Dylan’s eyes were on the woman.

We chatted back and forth for a while, until this couple lowered the camera to show that, below the waist, they were both completely naked. “Now you” came the next message, and Dylan, giddy with whiskey and excitement, proceeded to pull out his cock, and I almost choked.

I’d seen it a handful of times before when changing or swimming, but not like this. He was chubbed up, though not completely erect. His foreskin had slid back and was now trapped behind a bulbous pink helmet, and his balls were loose and heavy, and sat snug between his legs.

“Do it” he said, nudging me, and so without another thought, I exposed my dick, which was admittedly smaller than Dylan’s, and we lowered the camera and returned the favour.

The couple, who I believe were Dutch or German, seemed excited by our display, and instructed us to masturbate as they undressed fully. With my eyes still very much on the man, Dylan and I began our first jerk off session together, and boy, was it something.

The young man stroked himself, and the woman slid a finger inside and joined us in this very odd foursome. After around five minutes of jerking, the couple switched over, and began to pleasure each other.

“Now you”, once more, and Dylan and I gawped at each other awkwardly.

“I’m not touching his dick” Dylan said to the camera, but the couple ignored us.

We sat there, our softening cocks still in our hands, and grimaced as the realisation hit us, that in order to continue this explosive entertainment, we would have no choice but to follow the orders.

“Fuck it” Dylan said, exaggerating his slurs so that he could always fall back on the fact that he was ‘drunk’, if ever this secret got out.

He wrapped his hand around my cock, and I froze as I stared at it. “Do me” he growled, as though he wanted to get this over with as quickly as humanly possible. I reached out and held his one, and felt the heavy weight of it in my palm.

“Good” the message said.

So there we were, two teens jerking the shit out of each other for the simple purpose of seeing something which we could have found on any porn website in the world. Naturally, I was enjoying it far more than Dylan seemed to be, but he wasn’t exactly complaining, either.

After ten minutes or so, the couple did something that both Dylan and I had expected. The woman pulled off her sports bra to reveal a set of plump tits, and the man exposed his shredded torso. Without being asked, the two of us began a game of Simon Says, and stripped out of our clothes instantly.

“This is so fucking gay” Dylan reminded me, “but look at her tits, bro!”

I nodded mindlessly as I watched the man’s cock drip pre-cum. The sight, plus the fact that Dylan’s hand was robotically stroking my pin-hard cock, was making me shiver with pleasure.

She lifted the young man’s thick rod and fondled his balls with her free hand. It felt like we were watching some ‘how-to’ instruction video, because without a word, Dylan lifted up my cock, and I lifted up his, and the two of us began to massage one another’s nut sack.

“Nobody ever finds out about this, right?” He said, and I nodded eagerly, knowing that this would be the social suicide that all teenage boys dread.

I was verging on exploding after just a few minutes, until the strange couple switched things up. The man sat back in the chair, and the woman plucked his cock back into her hand, and did what Dylan had been dreading.

The two of us watched in awe as she slowly closed her mouth around her boyfriend’s knob, and twisted her hand around the base sensually.

“Fuck this, I’m out” he said, and reached for the mouse before the message appeared.

“Do what we do and we will show you everything”.

I glanced at him, and he shot an awkward one back at me. My heart was absolutely smashing inside my chest, and the two of us continued to watch the scene play out.

“Ten seconds” Dylan growled, “no more”. The couple didn’t respond.

Dylan sat back, and although he exhaled deeply, I knew that he wasn’t even remotely relaxed. I still had his cock in my hand, and could feel the thing soften as he imagined me sucking his dick.

“Just do it” he said, closing his eyes and covering his face with his hands.

Having never sucked a dick before, the only instructions I had to go by, were the ones being kindly provided by the young woman on screen. I watched her for a moment, inhaled deeply, and aimed Dylan’s cock toward my face.

My whole body tingled as I leaned forward and anxiously took the tip of his dick between my lips. It felt like fireworks, and in that moment, I knew that the rest of my life would be devoted to cock.

“Oh my god this is so fucking gross” Dylan sniggered, but he was watching me now, and I was eager to give my best performance.

“That’s more than ten!” He giggled, and pushed me away from him, and somewhat excitedly, Dylan leaned over and sucked my dick into his mouth without any warning whatsoever.

I gawped down at him. Sucking his dick had been magnificent, but him sucking mine was absolutely jaw dropping. I couldn’t believe my eyes. My best friend, who was undoubtedly straight, had so easily been convinced to suck my dick, because some strangers on the internet suggested it?!

“Your dick tastes like something” he pondered, and took another sample to be sure, “I don’t know, but it’s actually not bad” he added with a laugh, and sat back, completely indifferent to the fact that he’d just sucked a cock.

Maybe it was the drink, or maybe my best friend really did enjoy sucking my dick, and whatever the reason, I wasn’t complaining. It felt like our friendship had reached a new level, and it was difficult to hide the excitement that was now evident in my twitching prick.

“You liked that you fag” he joked, digging his elbow into me.

“No way” I lied, scoffing to throw the scent, “you did”.

Our argument was juvenile at best, but our attention soon returned to the screen of the laptop.

“Blond boy” came the words on the screen, and I was the only blond in the room, “you be the girl, he be the boy”.

Dylan smirked at me.

“They think you look like a girl” he sniggered, and I punched him in the arm.

The young woman was frantically rubbing her pussy with two fingers, and the man was jerking himself with such force that his large balls bounced with each stroke. She slid down the chair, hooked her heels onto the edge of it, and lifted her legs up, holding the back of her knees, and exposing her asshole.

“No fucking way” I said, cringing at the idea of showing Dylan my butt hole, “I’m not doing that”.

“Stop being a pussy!” He told me, forgetting to slur, “I wanna see what happens next”.

“You be the girl then!” I argued back, my cheeks burning, but Dylan ignored me and the two of us gawped as the man sucked his middle finger into his mouth, and proceeded to slip it up his girlfriend’s ass.

“Alright, yeah, that’s not happening” Dylan concurred, “I ain’t sticking my finger up your ass”.

I nodded, and just as we returned our attention and our boners back to the screen, it went blank.

“Fuck!” He groaned, “I was about to nut”.

I was buzzing with emotions from what had just happened. We’d jerked off and sucked each other’s dicks, and despite the fact that it was quick and meant nothing to Dylan, I was overjoyed.

We sat there naked for a moment, our cocks still throbbing, and our eyes pinned to the black camera. The message appeared a moment later.

“Do what we do, and you can watch”.

Neither of us spoke, which told me everything I needed to know. He was considering it. I was considering it, and when the screen flashed back and showed the man still roughly finger fucking his partner, Dylan glanced at me.

“If you tell anyone” I growled, and slowly got into the same position as the woman.

It felt odd to be so exposed in front of Dylan. Yes, we were best friends, but we’d never been in each other’s company like this before. On top of that, my asshole was now completely visible to two strangers, but neither of them seemed even remotely interested in us.

My heart pounded in my chest as Dylan took some reassuring deep breaths and eventually sucked his finger into his mouth.

“This is so fucking gross” he grimaced, covering himself in spit as I agreed.

I inhaled slowly, trying to calm my nerves, and watched as my best friend pushed his hand between my legs, closed his eyes and groaned.

The awkwardness came instantly. His wet finger brushed off my sensitive hole and the two of us accidentally stared at each other.

“Don’t fucking watch me!” He snapped, pushing against my opening, “this is already gay as fuck!”

I didn’t disagree, and so I turned my attention back to the couple on screen, and watched as the woman opened her mouth and moaned as her asshole was fingered vigorously.

Dylan slipped inside and I grunted as my ring clenched around his fingertip. It felt bizarre, and also extremely arousing. Pre-cum leaked out of my erection and spilled onto my stomach, but thankfully, Dylan didn’t notice.

He pushed deeper again, reaching his knuckle as a sharp dart of pleasure rushed through my insides. I couldn’t help but moan, and that resulted in Dylan slapping my exposed balls.

“Dude, if you moan again I’m punching them” he warned, and I grimaced but nodded.

My fingers squeezed the edge of the chair as he slowly slipped in and out of me. His eyes returned to the couple, and with his free hand, my best friend began to wank. It was the hottest and strangest situation I had ever found myself in.

“Faster” came the message, and his shoulders dropped but he sped up.

Not moaning was becoming harder and harder by the second. I had yet to work out the different parts of my body enough to know that Dylan was ploughing my prostate enough to force an orgasm, so when the couple finally changed things up, I was covered in sweat and pre.

“Dude, he’s gonna fuck her” Dylan gasped, and we both watched in awe as the man crouched down between the woman’s legs and thrust his cock out, rubbing it against her hole.

I waited for Dylan to vehemently refuse the order, but he stayed silent and watched as the man pushed himself inside her. His finger continued to glide in and out of me, and without a word, he turned back and shrugged.

“Wanna?” He asked, completely straight faced, and all I could do was gawp at him and nod.

I had no clue how it had gotten to this point. He had protested against some of the minor tasks, yet Dylan seemed utterly unbothered at the idea of actually fucking me. Had the alcohol really taken over him now, or did my best friend have more to hide than I had ever expected?

Dylan stood up and bent his knees as I held my legs back for him. We looked far more awkward than the hot couple on screen, and he fell over a few times as he tried to aim his cock at my wet hole. Eventually, he stabbed me with it, and the two of us stared at each other wide eyed.

“Seriously, bro” he said, his hands on the back of my legs, “we take this to our graves”.

“Deal”.

He pushed harder against me until I felt myself open for him. I expected more pain, but as Dylan drove his cock deeper, my asshole seemed to accommodate him.

“Fuck” he grunted, opening me, “this actually feels good”.

He could say that again. The pleasure he’d given me with his finger, was absolutely nothing compared to this. His cock pushed against my special spot once more, threatening to force an orgasm from me at any second, and a moment later, Dylan began to fuck me.

It wasn’t how I expected to lose my virginity, but I could think of nothing better now. He leaned forward, holding the arms of the chair to keep himself steady, and looking down at me as he thrust into my ring. He looked extremely hot, as his naked body glistened with sweat and his face scrunched up with aroused concentration.

I couldn’t help but moan now, and Dylan didn’t stop me. We tried to keep as quiet as possible, but the pleasure was more than either of us had ever experienced, so it didn’t work out too well.

My eyes rolled back and my toes curled as he pushed me closer and closer. I’d never had a hands free orgasm before, but I knew without a doubt, that if this continued for much longer, my first was coming.

His moans became deeper as his balls slapped against my ass. He was a natural, and despite the fact that he’d never put his dick into anything other than his own hand, he knew exactly what to do.

On and on it went, until my glassy eyes found the screen that I’d almost forgotten about, and I watched the hot couple fuck just like we were.

“Cum in him” the message said, appearing in the chat box, and they didn’t have to ask us twice.

Dylan whimpered as his legs shook, and he stared at me, wincing and gasping whilst his cock swelled inside me.

“Oh fuck!” He gasped, and I felt his balls tighten against me as he unleashed rope after rope of fresh teen cum into my hole.

I could only savour his orgasm for a moment. The entire ordeal became too much, and I squirmed as ribbons of sperm gushed from my untouched cock and squirted across my sweaty stomach and chest.

As our orgasms burned through us, and the room became damp with the stench of sex and cum, Dylan finally crumpled, and dragged his wet cock from my asshole, falling back onto his chair.

We sat in silence for a moment, both of us trying to catch our breath and make sense of the madness that had just occurred, and then something hit me, and I felt my blood turn cold.

“Dylan” I said, feeling the cum drip from me, and he glanced over, looking exhausted. “Um… I’ve just realised something”.

He cocked a brow. “What?” He asked, “that you’re gay?”

I ignored his snigger and nodded toward the screen where the couple had now returned to being half dressed and showing us that they were naked below the waist. His eyes widened, mine did, too.

“They haven’t typed a single thing” he said, as the realisation dawned on us both.

As the video played all over again, one final message appeared that made us both gasp.

“Thanks boys, you’ve made a lot of men very happy tonight. Enjoy exploring each other xx”.