An Awkward Encounter

All characters are 18+

"You better not get one before me" Charlie mumbled, sinking into the sofa with his arms folded. "It's not fair!"

As amusing as I found my best friend's little tantrum, he had a point. We had both turned eighteen recently, and the likelihood of us both starting college the following year, having never experienced even the slightest touch from a woman, was growing increasingly likely.

"I mean, I'm pretty damn good looking" he continued, eyeing the pizza that my dad had brought upstairs.

"Anybody who says their good looking, usually isn't" I told him, grabbing a slice.

"Shut up" he snarled, as I sat down beside him.

We'd been friends for as long as I could remember. He had practically lived in my house throughout high school due to the fact that his parents were rarely around. During the summer, however, most of our time was spent at his place, enjoying the freedom of an empty house.

"Do you know how weird we're gonna seem if we go to college like this?" He continued, though my mind was now solely on the string of cheese that I was attempting to catch with my mouth.

"It's not like you have to announce it" I told him, finally catching it "just lie".

"Dude!" He barked, turning to face me and pushing my leg with his socked foot "that's what weird people do! Oh yeah, I got my dick sucked by some chick I met on vacation. Who is she? Oh you wouldn't know her!" He mimicked, and I laughed.

The truth was, we were both quite cute young guys. Unfortunately, we had also reached that point where women no longer wanted 'cute', they wanted hot, and rugged and manly, of which we were none of those things.

"I should have joined the gym" he groaned, reaching for a slice of pizza.

"You're like one hundred pounds" I scoffed and he lifted up his t-shirt to show a set of barely developed abs.

"Oh yeah" I nodded, chugging from my can of Coke "the women are going to be dropping at your feet".

He kicked me again, sending a splash of Coke over my shirt.

"Idiot" I spat, feeling the moisture on my chest and pulling my shirt over my head.

"Like you can talk" he yelped, pointing at my smooth, thin body. "I've seen more meat on a butcher's knife!"

"Fuck you" I snarled, covering myself.

We continued eating in silence for a while until Charlie spoke again.

"It probably doesn't even feel that good" he said to himself "I bet it's overrated"

"I doubt it" I told him, turning my attention to the television now.

"Why couldn't you be a fucking girl" Charlie groaned.

"Dude" I laughed "that's the weirdest thing you've ever said"

I watched as his cheeks flushed red.

"Not like that" he growled "but it would be easier, wouldn't it?"

I ignored him and focused on the movie. Charlie had always been a joker, it was one of the reasons why I liked him so much. He didn't take things too seriously, most things anyway.

By eleven, I could feel my eyes grow heavy. As usual, Charlie was staying over, and it had become such a regular occurrence over the years, I no longer had to treat him like a guest.

"I'm going to sleep" I yawned, stretching my still naked torso.

"Wait" he said, and when I turned to look at him, his face was serious and concentrated.

"You know I love pussy, right?" He asked, and I nodded.

"Not just love but really love"

I nodded again.

"Like if I was stranded on a dessert island and I could only bring one thing, it would be pussy"

"Dude, what are you talking about?" I scoffed, imagining my best friend on a beach with a single vagina in his hand.

"Let's suck each other off"

The sentence hit me like a truck. For a moment, I was sure that I had misheard him. I spun around, my eyes as wide as saucers and glared at him.

"Ex-fucking-scuse me?" I gawped.

Charlie had turned the colour of a tomato. He looked away from me, unable to make eye contact and rubbed his face.

"Yeah" he nodded "it's stupid" he forced the fakest laugh I had ever heard and stood up.

"Guess I'll go to bed too" he announced, still looking the opposite direction.

"Dude, wait" I groaned "don't be like that".

"Like what?" He barked, his voice higher than I think he had intended.

"Are you joking or?" I asked, unsure if I wanted to know the true answer.

"Obviously" he scoffed "I told you, I love pussy".

He sat back down, his eyes were now firmly on the tele, unfocused but glaring. Part of me felt sorry for him, this whole thing had become an obsession for him in recent months.

"I just don't want to go to college without knowing what it feels like" he sighed eventually.

"I think people would probably find it a bit weirder if we... Did it together" I said truthfully.

I wasn't gay, and I was pretty certain that Charlie wasn't either, and yet here we were, the idea now floating through both of our minds. I didn't want to consider it, but he'd planted it in my head, and I couldn't prevent myself from toying with the idea.

"Yeah, I know. It was stupid" he said dully.

"And how would it even work?" I laughed, but truthfully I was trying to work it out "I do you, or you do me? Or we do each other, like sixty-nining?"

"We just take turns, I guess" he chuckled and a silence fell almost instantly.

"It's not like we're gay" he added a moment later.

"Yeah, no. I know" I replied, and I felt my face become warm.

"I bet lots of people do it"

I nodded. "Yeah, probably"

We both knew it at the same time. Something had changed in our friendship, and the pair of us could feel it. I glanced awkwardly at him, he returned the stare.

"We couldn't tell anyone, though" I said, my mouth becoming dry with nerves.

"No, of course not" he replied, and he too looked anxious.

"So" he added after another awkward few moments.

"So" I replied, unsure how to move forward with the bizarre plan.

"Um... Will I... I mean... Will we... You know? Get undressed, or is that too weird?"

"It would be a bit weird, getting naked, I mean. Wouldn't it?"

"Yeah" he nodded seriously "yeah, that would be weird".

We sat in silence again, my heart was now hammering in my chest. What on earth were we doing?

"Should we shower first?" He asked and I shrugged.

"I had one this morning, did you?"

He nodded.

"Okay, okay. Let's just do it" he sighed, his voice shaky as he leaned back in the sofa.

"I'm not going first" I barked, as he dropped his hands to his side and widened his legs.

"What do you mean?" He snapped back, his eyes piercing me "I came up with the idea!"

"Exactly!" I hissed, trying to keep my voice down "your idea, you go first".

"Fine" he growled "well... Take it out then!"

His face was as red as I knew that mine was. It was by far the most awkward moment of my life, and yet I could feel my cock begin to pulse in my underwear. The idea of pulling it out in front of Charlie made me cringe.

"Alright, fuck it" I said and thumbed the side of my bottoms, pulling them down my thighs until they rested around my knees.

My cock was slightly larger than average, and I knew it because I had measured it many times in the past. I wasn't ashamed of it, but I had certainly never envisioned showing it to my best friend. The idea was becoming stranger and stranger by the second.

"Are you sure about this?" I asked, staring down at my boxer briefs which were beginning to move over my stiffening rod.

"I think so" Charlie replied, and I could see him staring at my bulge from the corner of his eye.

"Nobody ever finds out about this?" I confirmed again and he nodded, swallowing a lump in his throat.

I inhaled deeply, still unsure if this was the best or worst idea Charlie had ever had, and then I grabbed the sides of my underwear and in one swoop, my cock sprung out and slapped against my shaved pubic hair.

"Dude!" He gasped, his eyes widening "how big is that thing?!"

I stared at it too, a sense of pride filling me but being overshadowed by the extreme awkwardness.

"Just over seven inches" I said truthfully, my entire body stiff "so... Are you gonna... Y'know?"

"Yeah" he nodded, though he didn't move a muscle "yeah, I will. Just... Just wait a minute"

"Bro, I'm not just gonna' sit here with my dick out" I told him, a rush of embarrassment passing over me.

"Right" he breathed "yeah, of course not".

Charlie shuffled closer to me, I could see his hands trembling as he reached for it. My own breathing was almost as frantic as his.

Closer and closer he inched, until finally his fingers rubbed against my soft shaft and I shuddered.

"What!?" He growled and I glared at him.

"What do you mean, what?!" I spat back and he shook his head.

"Sorry" he swallowed "I'm just nervous"

"You're nervous?" I half laughed "I'm the one that's half naked!"

"Right" he nodded "sorry".

He reached out again, quicker this time, as though he was trying to simply get it over with, and I felt as his hand closed around my semi-erect meat.

A shock of strange pleasure surged up my tool. I inhaled sharply as he squeezed it. Perhaps this wasn't the worst idea he'd ever come up with.

"Does it feel better than doing it yourself?" He asked quickly, his hand frozen in place around the base of my stiffening cock.

"I... I don't know" I stuttered "you're not really doing anything".

He slowly, almost robotically, began pumping my shaft up and down.

"Dude" I winced, as his grip tightened further "you're not churning butter, just take it easy!".

"Oh sorry that I'm not an expert wanker!" He hissed, but loosened his grip slightly and continued.

I couldn't deny that the feeling was amazing. It was certainly strange, being pleasured in such a way without using your own hand. My cock seemed to enjoy it too, and was now almost painfully erect.

"Why aren't you circumcised?" He asked curiously, watching my foreskin slide over my pink glans as he jerked me.

"I... I dunno" I gasped, feeling my balls begin to tighten "my parents didn't want to".

"Lucky" he groaned "I wish I had that".

"You know there's surgery to restore it?" He continued, and I looked from my throbbing cock to Charlie and shook my head.

"Can we just... I dunno... Focus?" I asked, feeling ridiculous.

"Easy for you to say!" He hissed "you're not doing anything!"

"Alright, take yours out" I said, unsure whether I actually wanted him to do that or not.

He considered it for a moment, his hand still sliding up and down my tool, and then nodded. He used his free hand to shove his bottoms down to his ankles and then he lay back.

"Well take it out" I growled, staring at the lump in his black boxers.

"Just put your hand in!" He spat back and I sighed as I reached under his arm and shoved my hand down his boxers.

I did it quickly, because if I'd thought about it too much, I would have talked myself out of it. He jumped.

"Sorry" he yelped "I... I wasn't expecting it"

When Charlie sat back again, I slid my hand deeper. I could feel the warmth inside his underwear and seconds later, I felt his soft, fleshy cock and a pair of heavy balls squashed together.

I could hardly pull my attention away from my own prick, which was now twitching against Charlie's grasp. It felt wonderful, like nothing I had expected.

I fingered my way under his flaccid rod until his small, soft cock sat in my hand. He gasped, just as I had.

"This feels good" I nodded and he silently agreed.

"I... I don't think I can... Get hard" he told me.

I don't know what came over me. Perhaps it was the bursts of pleasure that were sparking through my virgin cock. Perhaps I simply wanted my best friend to feel that same pleasure that I was experiencing, but whatever it was, I leaned over and pulled his boxers down to his knees.

"What are you doing?!" He gasped, reaching down to pull them back up.

"Relax" I told him "just... Relax".

For a moment, he froze and then slowly I used my thumb and forefinger to gently massage his tiny prick.

"It's only that size because it's cold" he told me, his voice shaking once again.

"Is it?" I grinned, but it seemed that the freedom of nakedness had done the trick as Charlie's cock began to grow.

I sat back, as did he, and we continued to masturbate each other in silence. He moaned, and then I moaned. He gasped, and then I gasped. It was feeling better and better with every second that went by.

"Should we... You know?" He asked and I nodded instantly.

"You go first this time" he said, staring at his own erect cock which was quite handsome, albeit an inch or two shorter than mine.

"Fine" I growled and stood up.

My cock bounced as I got to my feet. It was the strangest feeling, standing inches in front of my best friend whilst my erect prick jumped up and down.

He laughed.

"What's so funny?!" I hissed

"Nothing" he replied, wiping the smile from his face "sorry".

"No!" I barked "why are you laughing?" I could feel my face turn even more red than it had been.

"It's just... This" he shrugged "it's funny".

I stared at him for a second, eyeing his stiff cock before laughing myself.

"Yeah, I guess it is" I scoffed.

Charlie spread his legs wider as I stood between them. My eyes ran down his thick shaft, falling to his low hanging balls and further again to the seam that ran between his junk and his asshole. Why did the sight of it cause my prick to swell?

"You ready?" He asked, now pumping his own dick.

"I... I think so" I gulped and awkwardly got to my knees.

I reached forward, taking his cock out of his hand and pulling it toward me so that it faced up at the ceiling. It felt strange from this angle. I could see the sensitive underside, the veins beginning to bulge, and then a single bead of clear fluid spilling from his exposed slit.

"Wipe that!" I ordered, almost dropping his cock as it began to trail down his shaft.

"Oh shut up" he argued "just do it!"

I watched the bead of pre-cum as it slid over my fingers. I wasn't sure whether to be disgusted or excited, but my own cock was throbbing violently.

"Don't look at me" I snarled, leaning my head closer to his crotch.

"What the fuck am I supposed to look at then?" Charlie spat.

"I don't know!" I replied "watch the movie!"

His eyes moved from mine to the tele behind my head and I took one last deep breath before opening my mouth, squeezing my eyes shut and lowering my head.

The second his warm, salty, wet glans touched my tongue, I gagged brutally and pulled away.

"I... I can't" I retched, dropping his cock and shuffling backwards "that's fuckin' gross".

"Stop being such a pussy!" He groaned, leaning forward "I'm gonna do it for you!"

There was something almost pleading in his voice, and despite the idea turning my stomach, I sighed and grabbed it again. He sat back instantly.

"Don't think about it" I told myself "just do it".

I repeated the same motion as before, and a moment later his wet cock head slid into my mouth.

It wasn't actually that bad, but it was as though my mind was forcing me to hate it. I wrapped my lips tighter, adding suction as I took more of it into my mouth. I felt him shudder and heard him gasp as he inched his cock deeper.

A string of pre-cum spilled from my own erect cock now, which was bouncing between my legs, lonely and untouched.

As difficult as it was to admit, Charlie's cock tasted good. I lowered my head further, his tip pushing into my throat, and I gagged on it, but kept it inside.

"Fuckkk" he moaned above me.

Deeper now, I could feel his shaft opening my throat further, and I gagged again.

"That feels so good" he whispered, and his hand slowly ran through my short hair.

I didn't know how to feel about it. This was a job for a woman, not me! And yet I was enjoying it, I was really enjoying it.

His balls were now pushing against my chin, becoming wet with saliva and his own pre-cum. I wanted to reach down and grasp my own rod, but how strange would that look? Charlie would surely think I was gay.

"Go up and down" he whispered, and another rush of embarrassment ran through me.

I lifted my head slightly, feeling his wet cock slide from my throat, and then I took it again, helped by Charlie's guiding hand.

He gasped with pleasure as his cock head pushed back into my throat.

"Yeah" he groaned "do that again".

I did. Up and down as he trembled beneath me. Up and down, up and down. His cock swelled in my mouth and my tongue began lapping at the sensitive strip on the underside.

Charlie shivered and moaned louder than he had before.

I tried to tell him to be quiet, but my voice was dulled by his drooling rod, which was now leaking copious amounts of fluid into my throat.

I placed my hands on his naked thighs and pushed myself up, a string of saliva and pre-cum trailed from my mouth to his soaked head as I glared up at him.

"What?!" He gasped, his cock now twitching violently as it slipped back against his smooth stomach.

"Uh... How about my one now?" I snapped and he looked as though I'd just slapped him across the face.

"Just a few minutes more?" He asked, his eyes pleading.

As much as I wanted to continue swallowing my best friend's cock, I also wanted to experience it myself. I stood up, liquid pouring from my slit as I did, and sat back down.

"Asshole" he spat, and grabbed my cock unexpectedly.

"Easy!" I yelped, but the sharp shock of pleasure that I had enjoyed earlier, returned as he squeezed it.

I watched as Charlie slid onto his knees on the floor and roughly spread my legs. It was clear that he was unhappy that I had stopped so soon, but this was our deal, and I was intent on getting my end.

"Yours is too big" he told me grumpily as he held the base and examined it.

"Thanks" I smirked "now suck it".

He threw me a dirty look before using his t-shirt to wipe my wet tip.

"Hey!" I snarled "no cheating!"

He ignored me and took a deep breath.

"Ready?" He asked, but didn't wait for my answer.

Charlie opened his mouth and plunged his head down my cock. A ripple of sensual pleasure tore through me. I was right, it wasn't overrated.

I could feel his lips against my shaft, sucking and slurping. His tongue lashed up and down the underside, sending waves of intense arousing joy through me and for a moment, I could hardly breath.

It was wonderful. Every slurp, every bob, every lick. My mind was blown. My body began to tense, my fingers dug into the sofa beneath me as he pushed on, deeper and faster, harder and stronger.

I moaned deeply, my hands instinctively reaching for Charlie's head, but he slapped them away, mumbling into my meat.

I was close, much closer than I had ever expected to be with my cock buried in Charlie's throat. Another minute, another long lick and it would happen. I closed my eyes, my hips thrusting forward and I felt it rumble in my balls.

"Alright, my turn"

Charlie stood up, his chin wet and his eyes watering from the length of my cock.

"What? No!" I almost cried "just a minute more!"

He grinned at me as he reached for his own semi-erect, leaking cock and shook it.

"My turn" he repeated.

Part of me wanted to punch him, the other part wanted to take his cock fully inside my throat once more, but my own prick was now twitching and aching for release.

"I have an idea" I told him, and I too stood up.

"We're not kissing!" He snapped, almost falling back over the coffee table.

"I don't want to kiss you, you weirdo!" I hissed back, pushing by him and walking to the bed.

"Come here" I said as I lay down.

"I'm not fucking you either" he added, and apparently fucking was only second on his list of things he didn't want to do.

"Just get over here!" I ordered, pointing to the area beside me.

Charlie walked, half naked toward me. His cock slapped against his thighs and I watched as he pulled his t-shirt off and crawled naked onto the bed.

"What?" He asked, evidently impatient "what's your idea?"

I shuffled in the bed, positioning myself so that my cock was now pointing toward his face, and his, toward mine.

"I thought we agreed no sixty-nining?" He said, eyeing my meat.

"Yeah, we did" I replied, taking his one in my hand and pointing it toward my mouth. "But that was before I realised how fucking good it felt".

I gobbed it into my mouth, feeling it push deep into my throat again. Charlie gasped, but a moment later I felt the warmth of his mouth, sucking on my eager prick.

My mind couldn't make sense of it. The pleasure gushing through my cock felt only slightly better than the pleasure I was getting from throating my best friend. Was I gay? No. I couldn't be.

Charlie was moaning into my cock, his own one was spilling mass amounts of salty fluid onto my tongue as I took it over and over again. I wrapped my arm around his waist, dragging him deeper into my throat, and he did the same.

We were embraced passionately, our hips thrusting and our cocks vibrating with each stroke. His body felt wonderful against mine. The taste, the smell, everything. My hands grasped his bare cheeks, squeezing them and pulling him toward me.

He groaned, his body shook. My muscles tensed, my toes curled. Both of our bodies seemed to be in tune, waves of pleasure washed over the pair of us.

He grunted into my cock again, and I knew it was his warning. I knew it, because I felt it too. I was about to cum, and so was he.

Charlie pulled his head back as my cock began to spasm, I felt it slip out but I buried my head deeper onto his. I wanted to taste it, I wanted to feel my best friend fill me with his seed, and my willingness seemed to rub off.

I felt his mouth close over it again, and as it did, a pleasure like I had never experienced, shot through me and my cock began to squirt ropes of thick, heavy cum into his throat.

My mouth flooded, his sticky, hot sperm gushed around. I savoured it as more and more spilled, and then I swallowed, and I continued squirting as I felt it slide down my throat.

He swallowed too, I could feel his throat muscles contract around my sensitive, spewing tool and we both fed each other for the first, but hopefully not the last time.

We separated, laying on our backs and staring at the ceiling as our chests rose and fell rapidly. I didn't know what to say, my mind raced through the events. Had that been the best moment of my life? Had it been his?

"Well" he breathed "that was interesting".

"Yeah" I nodded breathlessly.

The room remained completely silent, other than our laboured breathing, until Charlie spoke again.

"Was that kinda gay?" He asked and I looked over at him.

"Nah" I smiled "it's only gay if we enjoyed it"

"True" he nodded, and squeezed his flaccid, dripping cock "so I guess it was very fucking gay".

We both laughed as we lay there, naked, drained and content.