Skinny Dipping and Discovery
By: Date: 2021.05.23. Categories: Sex Stories Tags: , , , , ,

It was a pretty typical summer night. I had just graduated high school, and was trying to stay out with my friends every night before college started. We didn’t do a lot, we lived in a small town, so there wasn’t really anything too do, especially at night. We would find our own entertainment though, usually wandering around the streets talking about anything and everything. Occasionally fucking around at the park, breaking into our school for no reason, etc.

On this particular night, it was just me and 3 friends. Since it was a small town, and therefore, small school, not all of us were in the same grade. It was me and my friend Chris, who were in the same class, our friend Tracy from one grade below, and Dylan, from two grades below us.

We all wandered and talked, and it was probably around 1am at this point. It was a very humid night and pretty hot out, and Dylan suggested that we go to the swimming pool. It was obviously closed at this time, but of course we knew which section of the fence was loose, so getting in was no problem, and we all agreed it seemed like a great idea, and off we went.

The pool was in a fairly isolated part of town, and it took a while to get there. Part of the fun of wandering around this late, was avoiding the one police officer on duty. Again, we never did anything destructive or super illegal, but there was a curfew technically for Dylan and Tracy, being a couple years younger and still in high school, so we made it a game of hide from the cops.

Eventually, we made it to the pool, found our hole in the fence and all sat down at the edge. We kicked our shoes off and dangled our feet and legs in the water.

“Great idea Dylan,” Chris said, “This feels great!”

“Yeah,” he replied, “I wish we had our swim suits though, I’m still hot.”

“Who needs a swim suit,” I joked, “Let’s just jump in naked.”

We all laughed, and Tracy had a mock disgusted look on her face.

“I do NOT need to see all of you naked,” She laughed.

I was sort of joking when I suggested it, but secretly I wanted to for one reason: Dylan.

So far as everyone knew, I was straight. In fact, there wasn’t any gay people in town at all that I knew of. But recently I’d started kind of questioning myself. I don’t know why, like I had girlfriends, on and off, but never did anything sexual, it just never felt right. But as of late, I would catch myself checking out guys and fantasising about them later. I didn’t really know what to make of this, so it was still bottled up inside.

Dylan was more and more frequently one of these fantasises. He was 16 at the time, and I’d seen him shirtless once or twice. He was smooth except for a bit of stomach hair forming a small ‘treasure trail,’ and a bit of armpit hair. He was about 5’ 9”, and was not particularly muscular, but very toned. It was like the perfect body. And so my skinny dipping comment was me secretly hoping to goad him into getting naked.

“Fuck it, why not?” Dylan replied. “I’ll do it if you guys do.”



I was stunned, and probably stayed awkwardly silent for too long, before stuttering out an agreement.

“I-I-I mean w-why not?? Yeah, why not? It’ll be fun!” I recovered my composure.

“Yeah, I’m out.” Tracy replied.

“Tempting, but I’m going to sit this out too,” Chris replied. He was always trying to side with Tracy. He wanted a bit more than friendship with her, and I don’t blame him, Tracy was awesome. But sometimes, it was lame, and he’d try too hard to impress her like that by ‘being more mature’ or whatever.

“Well, you still in?” Dylan looked at me. I couldn’t move for a second, he had gorgeous dark brown eyes, partially hidden by dark brown hair that was kind of set in a shaggy emo swoop. And his smile was intoxicating.

“Fuck it, let’s get naked!” I laughed.

Dylan stood up, putting his crotch at eye level with me. It was probably my imagination, but it looked bigger than normal, and I had looked at his bulge plenty of times before, so I had an idea.

He walked over to the beach chair and immediately stripped off his shirt, and started working with his belt. This was impossible, and as I stood up, my body was not in my own control, as I followed his lead over to the beach chairs, taking my shirt off on the way.

I’m a pretty slender guy, about 6’ tall, and only about 140 pounds. Dylan looked at me and laughed a bit.

“You’re so scrawny, you should work out with me sometime,” he quipped at me.

“And have to deal with all the weightlifting assholes?” I replied, “No fucking thank you. Those guys suck.”

It was true, the jocks at my school were complete shit. One of the reasons I was glad to be leaving for college after the summer. Dylan would occasionally hang out with them though, since he was a football player.

“Fair enough, they are kinda douchy,” He laughed.

At this point, we were both standing in our underwear facing each other. He was wearing black UnderArmour style boxer briefs, and I was wearing pretty normal plaid boxers. It was hard in the dark, but I could sort of make out the outline of his dick through his underwear. I couldn’t help but stare at his body, and I had to do something quick, I could feel myself starting to get a boner.

“You ready?” I asked?

“On three,” he smirked, “One…Two…THREE!”

No turning back now, both of us stripped off our underwear in one quick motion. I managed to get a quick glance at his cock before we started running to the pool, and it was amazing. It had to be over 7” and looked like it was semi-hard. Again, that had to be just my hopeful imagination.

We both ran on either side of Chris and Tracy and jumped into the pool, both of us doing cannonballs that splashed them. We laughed as we surfaced, and you could see Chris trying not to laugh.

“Uhhgg, assholes,” Tracy glared. I couldn’t tell if she was legit pissed, or just playing her role as the mature one of the group.

“Come on in!” Dylan laughed, “This feels great!”

“It feels like we already did jump in,” Chris laughingly replied, shaking water off his arms.

We stayed this way for a while, Dylan and I swimming around naked, but close enough to the edge to still talk and bullshit with Chris and Tracy. I tried going under the water once in a while so I could look at Dylan’s dick, but without swim goggles, and especially in the night, it was a lost cause. Thankfully, this made my boner subside for the time being.

After while of this, Tracy stood up, shouting “Fuck! The cops are coming through!!”

As part of the patrol, the one cop on duty would drive through the pool parking lot to look for anyone doing….well exactly what we were doing.

Chris and Tracy bolted for the hole in the fence. There was a forest right there, so they would be fine. Dylan and I on the other hand…Our clothes were on the far side of the pool, and the lights from the cop car were getting near fast. We swam to the side of the pool, and Dylan pulled himself up and out of the water slightly before me, giving me a clear view of the best ass I have ever seen, even to this day. It was perfectly round, muscular, and hairless, even more accentuated with the water dripping off him. I almost slipped back into the pool in a daze at the sight of it, and I felt an instant stirring of a new erection starting.

Logic took over my brain, however, and I pulled myself the rest of the way out of the pool. We ran after our clothes, and grabbed them in one scoop.

“Shit!” Dylan said to me, “I don’t think we can make it out of the fence, we’ve got to hide!”

There was a small shower cabana close to us. We looked at it and ran, pulling the tiki style door shut behind us. We were out of breath, but theoretically safe, as long as the cop only did a drive through of the parking lot. His headlights shown under the door of the cabana, letting us know he hadn’t left yet.

It was then that I felt something pushing on my leg. The cabana was pretty small, even for one person, and with Dylan and I squished perfectly too close together in here, I realised it was his boner pushing on my leg!

My heart skipped a beat, probably from immediately sending ALL of my blood to my dick. I was instantly rock hard, but I was at an angle where my dick wasn’t touching Dylan. I couldn’t help but look down, and in the dim light, sure enough there was a hard cock staring back at me. It was even bigger than before, easily over 8”, which just looked giant compared to my 6.5” boner. His light treasure trail stomach hair blended perfectly into the small, closely trimmed bush of pubes he had. His foreskin was partially slid back, exposing the head of his dick.

He must have noticed me looking, or noticed that he had a huge erection touching me.

“Shit! Sorry!! It’s just the adrenaline, I swear!!” He tried to convince me. But I wasn’t convinced, and I certainly wasn’t going to pass up an opportunity like this…

The headlights from the cop car began to recede, signalling us that we were in the clear. I took my chance. This could go one of two VERY different ways right now, but I was too horny to care. So I turned my body to face his and made sure that he could feel my boner too, and then I made the ballsiest move in my life. I looked him in the eye, and reached down, grabbing his dick in my hand. I gathered up as much confidence as I could and repeated his own words back at him

“It’s just the adrenaline, I swear.”

There was a momentary look of confusion on his face, and I tried to maintain the fake confidence on my own. I couldn’t tell if he was going to run, punch me, or….kiss me?

Holy shit, his eyes cleared of any uncertainty and he leaned in and kissed me right on the lips, while reaching down and grabbing my dick at the same time. I was taken aback and it was my turn to be confused. Was Dylan gay too???

No time for thinking though, as we started grinding together and stroking each others cocks while we made out in the cabana.

At this point, My mind is reeling in ecstasy, and I can’t believe what is actually happening. I must have drowned in the pool and died, and this is my heaven.

His lips were soft as they attacked mine, and our tongues danced in rhythm with our gyrating bodies. I don’t know how, but with every stroke of our dicks, both of us seem to be getting even harder still. I could barely take it and had to fight the urge to cum already, I needed to savour every possible second of this.

I knew that Dylan felt the same, the tip of his cock was soaked in precum, and he moaned as quietly as he could maintain. The cop may have left, but what if Chris and Tracy came back and heard us?? For a moment, this fleeting thought scared me into almost stopping this madness, but the pleasure instantly overtook me, and right then, I couldn’t care less if the entire world was watching us.

My free hand moved to explore more of this glorious body. I slid down his neck and shoulders, pausing at his armpits, feeling the small patch of soft damp hair there, but I quickly moved on, his hot, perfect ass, my obvious goal.

He took a cue from me, and moved his free hand from my head. No exploring for him though, as he immediately went down and grabbed onto my balls and starts to softly massage them while he continued to jerk me off.

I love the feel of his foreskin under my hand, but I slowed my pursuit on making him cum, to return the ball massage, and my other hand finally reached the promise land, and I can’t even believe how good his ass feels in my hand.

He moaned slightly louder as I squeezed his butt, and stopped kissing me to bite my earlobe. It’s too much for me to handle, and I whispered “Keep going, I’m going to cum!” before biting down on his shoulder to keep me from screaming out in pleasure.

He tightened his grip on my shaft and jerked me off even faster. He took his hand off of my balls and reached farther under, starting to finger my ass.

That’s the last I could take, and my body shuddered, and I tightened my grip on his ass and pulled him even tighter to me to keep from collapsing as shot after shot of hot cum erupted from my cock. The pleasure was insane, and it seemed like it’d never stop, I was trapped in an infinite orgasm with the hottest guy on the planet.

I finally stopped cumming, but my body was still twitching every time Dylan continued to stroke me, slower now, but still going.

I was panting and out of breath, and he finally stopped torturing me with pleasure, and moved his cum soaked hand to his own cock, still hard and waiting to explode.

“Finish me off,” he whispered in my ear over the soft squishing sound of my cum being used as lube coating his dick.

His hair was soaked with sweat and pool water, as I looked him in the eyes. I could see nothing but passion and hunger as I leaned in to kiss him on the lips once more, before moving down to his neck.

Kissing his chest.

His stomach.

His waistline.

I pulled back, now on my knees, and took in the sight inches from my face.

Dylan slowly stroking his beautiful cock, now covered in my cum. My erection had been starting to subside, but I could feel my hard on coming up again. This was unreal and better than any fantasy I could muster.

I peeled my eyes away momentarily to look up at the god jerking off in front of me. He gave me a cocky smirk, knowing what I wanted to do, and whispered down to me, “Do it.”

It wasn’t love, but my stomach did a backflip with the emotions flooding through my body. My eyes filled with lust as I grabbed his ass once more and pulled his throbbing cock to my mouth.

My mouth filled with dick and the taste of my cum on it was delicious. Surprisingly, even though I had been having gay thoughts and jack off sessions for months, at this point, I’d never tasted my own cum. But now I was hooked and couldn’t wait to taste Dylan’s sweet sweet jizz.

He moaned with pleasure as I sucked his dick. He grabbed my hair while I licked from his balls to the tip of his boner. His cock was huge and almost gagged me, but I pushed on out of sheer pleasure.

Dylan started gently humping my face and I urged him on pulling his sweet ass in with every thrust. His moaning was intensifying, and I could tell he was close. I moved my hand from his asscheek and put my finger up to his hole. He instinctively clenched up, but quickly relaxed as I slowly entered.

It was his turn to be pushed over the edge with that, and he tried to whisper, but it came out louder than he intended, “Oh shit, I’m cumming!!”

I had no chance to prepare for the massive cumshot that was about to be unleashed on my throat. The first burst felt like someone hit me in the mouth with a super-soaker. His hot cum blasted the back of my throat and there was no time to swallow before more and more jizz filled my mouth. I kept sucking the best I could, as Dylan’s cum started to leak out of my mouth. I just couldn’t keep up with the volume he was pumping into me.

I pulled back and let his last several cumshots cover my face. My hair was matted with it, but I didn’t care at all. Dylan was panting with exhaustion as I took a couple more gulps to finish swallowing his huge load. He fell back against the wall and slid down to a sitting position. I sat as well, and both of us stared at each other’s naked bodies.

My god he was gorgeous, especially in this moment. I couldn’t help myself, I pulled him closer, and put my legs over his so we sat chest to chest, my arms around him, and our still semi-hard cocks pressed together. He grabbed the back of my head, and we passionately kissed before just sitting and staring into each other’s eyes for a minute.

There was a strange understanding being communicated between us without words being exchanged. Neither of us fully understood what had just happened, but we both knew it wouldn’t be the last time.

“We should probably get out of here,” Dylan said, breaking the intense silence of the night.

“Fuck,” I reluctantly agreed, “I suppose we should before Chris and Tracy start looking for us. “One second though, I need to rinse your fucking jizz off of me.”

We both laughed as I stood up. I extended my hand to him and helped him up before turning on the shower in the cabana. I closed my eyes and started rinsing my hair and face off, and I felt Dylan reach down and play with my softening cock.

“No fair!” I laughed as I pulled him under the shower water with me, “I want some too!”

I reached down to grab his dick as we kissed again under the water. His body felt fucking incredible pressed against mine.

“Fuck, let’s go,” I said. I could feel both of us getting hard again and we really had to get out of there before we got caught.

“Fine,” Dylan replied, “Shame to have to get dressed, but you’re right.”

I shut off the shower and we grabbed our clothes. We didn’t have any towels, so everything went on wet, which sucked, but his dick outline looked great in his wet underwear before he slid his pants back on.

After we got dressed, I slowly cracked the door open to make sure the coast was clear. It was and we snuck our way over to the hole in the fence. We slipped through and were almost immediately spotted by Tracy and Chris as they came out of the woods.

“Shit, there you guys are!” Tracy quietly called out, “We thought you got busted for sure! Where were you?”

“Sorry,” Dylan piped up, “We hid in the shower cabana, and we couldn’t tell when the cop left, so we laid low for a while.”

“Fair enough,” Chris said as we began walking away, “Well that was some kind of adventure, let’s get out of here.”

“You’re right about that!” I laughed as I stole a knowing glance over at Dylan, who couldn’t help but blush. Thank god it was dark out so they couldn’t tell.

We all started walking away, Chris and Tracy took a small lead, while Dylan held back a bit and walked next to me. I felt him grab my hand and give it a gentle squeeze. I looked down in disbelief just as he was letting go. Looking up at his face, though, he had a huge grin on his face. I couldn’t help but smile from ear to ear myself as we all walked home to bring a close to this amazing summer night.

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