The Pool Creep

This is a commission from someone on the Legendary tier. 

All characters are 18+

I was hot.

I mean that literally. The summer had well and truly arrived, and with it, a heatwave that would last for weeks according to the weather forecast. Just like every year, the first ray of sunshine encouraged every person, old and young, to make their way to the local swimming pool to cool off. For me, it was a blessing and a curse.

At eighteen, I had so far lived a very comfortable life. We weren’t rich exactly, but money had never been an issue in my family. Mom and dad both had good jobs, and I knew that if I really wanted to, I could have skipped out on having to find a job that summer, but that would have come with conditions.

They were travelling across the country, and further again after that. I had the option of going with them, but the idea of spending the entire summer hauled up with my parents watching my every move wasn’t as appealing now that I had become a very active young man.

And I was active. I’d been playing sport since I was in diapers. Dad enrolled me in a toddler soccer camp when I was two years old, and I’d been hooked ever since. In school, I’d gotten into lacrosse and baseball, and on more than one occasion, I’d led our team to finals and won. However, those aren’t the activities that prevented me from going with my parents.

The last few months had been a whirlwind of sexual awakenings. I found myself so incredibly aroused that even the warm summer breeze had me swelling in my shorts. I jerked off three or four times a day, and the hunger for pussy was becoming more and more insatiable with each passing second.

There was simply no way that I’d survive a summer trip with my parents, and so my options were severely limited. If I wanted to stay at home, close to all my friends, with an empty house and an endless opportunity to jerk off and potentially even bring a girl back, then I needed to find a job.

Luckily for me, being relatively handsome with a penchant for sport made me the perfect candidate for a job at the local pool. The hours were pretty good, the scenery had its moments, but the best part of it was that I got to spend time with Clarissa.

She and I had similar shifts. She’d been working as a life guard for the last two years, so she was showing me the ropes, and I was quite happy to follow her around as she did.

It took a week or so before I was confident enough in my new position, that I could spend my time focusing on her rather than all the rules and regulations. God, I would have spent all day focusing on her if I could.

It was a typical Saturday afternoon. The heat outside had driven almost everybody in, so the place was crowded with people of all shapes, sizes and ages. Some kids splashed around in the shallow end, the older teenagers cannonballed into the deep end every time Clarissa and I turned our backs, and other than that, the rest of the people were a mixed bunch.

I sat on one of the plastic chair wearing just my red shorts. They, alone, were the uniform provided, and I was quite certain that the person who had owned them before me, was a very weirdly proportioned man.

The waistband was loose, which meant that I was constantly pulling them up my hips, but the crotch part was incredibly tight, and gave me an unfortunate bulge that only worsened when I had to jump into the pool. I had begged for a different pair, but this was all they had, so I made do.

“Wanna do a round?” Clarissa asked, and I nodded.

Doing a round meant splitting up and taking a walk around the pool until we met on the other side. I didn’t really want to do anything that involved not being by her side, but we separated and began.

Most of the people ignored me, which was fine. I preferred being ignored, it usually meant that I didn’t have to do anything when I was being ignored. As I continued, I felt eyes. You know the feeling, just an inclination that someone, somewhere is watching you. I smiled to myself, hoping that when I turned back, Clarissa would be staring from the other side, but my smile quickly vanished.

The man looked to be around fifty or so. He was standing on the edge of the pool, his shorts, tighter than mine, stuck to him to reveal parts of his body that he shouldn’t be revealing. He had a large gut, and was rather overweight in general. He stared at me like I owned him money, but I forced a smile and a polite nod, and expected that to be the end of it.

It wasn’t the end of it. The man continued to gawp at me, but the longer I looked back, the more I realised that his eyes weren’t on me exactly. I followed his gaze down my body and felt my stomach churn as I realised that, once again, my shorts had slid down at the back, revealing a pair of white briefs.

“Fuck” I hissed to myself, angry that I’d let it happen, but angrier again that this creep was staring at me. I dragged them back up, tied the rope again, and shook my head to show that I thought he was a pervert.

Now, I’m a pretty laid back kinda’ guy. I had a friend in high school who batted for the other team, but in no way, shape or form am I even remotely interested in men. The idea sent shivers of disgust through me, but there was a vast difference in a guy checking me out, and a guy checking me out. I was happy to take compliments from anyone, but creeping on me like that, creeping on my ass like that, it was disgusting.

“Did you see that perv?” I growled when I met Clarissa on the other side, “he was staring at my ass!”

She found it quite funny. She teased me about it, told me that now I know how chicks felt, and I guess she was right, but it was still nasty.

“I have a free house all this summer” I said casually, as we returned to our seats, “gets real boring spending all my time alone”.

“Oh, does it now?” She smiled, and I felt my heart thump. “Is that an invitation, Mason?”

“Only if you want it to be” I replied, acting as smooth as I could.

She laughed and considered it, and just as she opened her mouth to reply, a loud, panicked rasp echoed around us.

“Fuck, go!” She barked, as the two of us got to our feet and scanned the pool.

I noticed him instantly, more so because with each frantic splash, the pool rippled.

“It’s him!” I groaned, but Clarissa was already pushing me forward, and I understood why.

Regardless of what the man had done, he was still struggling, and it was my job, after all, to rescue him.

I rushed toward the edge, dove through the air and within seconds, my slender, ripped body had soared beneath the surface and emerged with Mr. Pervert.

“You shouldn’t be in the deep end if you can’t swim” I warned him, clasping my arms around his torso as I dragged him back toward the steps, “you could have drowned!”

“I know, I know” he gasped, and for a moment, I felt a little bad for him, and then that feeling died.

His hands closed around the cheeks of my ass, and my eyes widened.

“Stop it” I growled, but the man didn’t stop. In fact, not only did he not stop, but he began to squeeze, fondle and play with my butt as I hurried toward the edge.

As we both got out, I glared at him furiously. I didn’t want to say the word, but as the man stood up and winked at me, I found myself bitterly close to roaring the slur at him. I couldn’t believe that it had happened. I’d let some creepy man molest me in the pool, and he was fucking winking at me?!

I stormed back to Clarissa before I allowed myself to get carried away. I spent the rest of my shift doing everything I could to avoid the pervert, and thankfully, he seemed to get the hint. When the time came to clock out, I’d never been as relieved.

The changing room was particularly quiet. It was usually bustling with people coming and going, but I was glad of the peace. It had been a long day, and I was more exhausted than I’d realised. I’d have to wait until tomorrow before I could convince Clarissa to come over.

I smiled to myself as I imagined it, but once again, the smile vanished when I turned around and found him there.

He was drying himself with a towel. His wet shorts were already hanging over the bench, and I knew that behind the small towel, the man was as stiff as a rock. I opened my mouth to warn him, but he got there first.

“How much are they paying you here, son?” He asked, and the words lodged in my throat. “Because whatever it is, I’ll bet a thousand bucks for one hour will beat it”.

“What the fuck are you talking about?” I asked harshly, feeling my cheeks redden as the naked man chuckled.

“Oh, come on” he grinned, “I know you ain’t that innocent, kid. I saw the way you were talking to that life guard chick, you know what it’s like to have needs”.

I couldn’t believe my ears. Was this man trying to proposition me?

“One thousand dollars” he continued, “and all you gotta do is let me look after you for an hour”.

My face scrunched up in disgust. Was this guy fucking serious?

“Look after me?”

The idea made me squirm, but one thousand dollars was more than I made in a month at this place.

His eyes scanned my half naked body again, and his tongue ran across his bottom lip. His hand moved a bit faster over the towel, and I grimaced when I realised that the guy was fucking jacking off!

“One hour, in my car” he said, “just let me worship that beautiful fucking body you’ve got”.

My instant reaction was to tell the guy to fuck off. No amount of money in the world would convince me to become gay. But then the man spoke again.

“You don’t even have to take off those sexy little briefs you’ve got on under there” he continued, and I almost gagged. “You sit back in your undies, and let me make you feel real good”.

Despite the feeling of disgust inside, I couldn’t deny that it was a pretty good offer. I didn’t even have to get naked, and I’d come out a thousand dollars richer for just an hour. I considered it, and he could see that I was considering it.

“Fine” I mumbled, “but you ain’t touching my ass, got it?”

The man chuckled again and I watched, slightly nauseas, as he pulled on a pair of loose boxer shorts and dressed again. “I’m parked right outside” he told me, and I looked around, sighed loudly and followed.

I told myself as I walked behind him, that once this madness was over, I would never again think about the events that took place here. I was bitterly disappointed in myself for being so easy, but what could I say? That much money in my pocket for an hour of letting some creepy fuck rub me? It seemed like a solid deal.

“What’s your name, son?” He asked, sitting in the driver’s seat as I squirmed in the passenger.

“Mason” I said quietly.

“Well, Mason, I gotta say, you’re the best looking guy I’ve ever seen in my life”.

I didn’t answer him. I couldn’t answer him. What had I gotten myself into? His hand reached over and pressed down on my bare knee. Even his touch made me queasy. I stared at it for a moment until I realised that it was best to look out the window instead. Perhaps if I started counting, I’d take my mind off the disgusting ordeal that was about to begin.

“You don’t mind if I talk, do you?” He asked, his voice now becoming wet with excitement, “it’s just, I want you to know how much I want you”.

“Do what you want” I gulped, and watched as three guys I knew from school walked across the parking lot, laughing and joking with each other. What would they think if they could see me now?

“You’ve got such beautiful legs, Mason” he whispered, sliding his hand up the inside of my thigh as I squirmed. “I bet you play soccer, right?”

I nodded stiffly.

“I can tell. Oh, yeah, you’re making daddy real happy”.

“Alright, that’s enough” I said, almost choking on vomit, “no more talking”.

The man nodded, but kept his hand in place. He was creeping closer toward my junk, and I had to actively think of other things to prevent me running away. I thought of Clarissa, and how good she looked today, and every day. When the creep brushed his fingers over the outside of my groin, I realised that thinking about a very attractive, half naked young woman was the worst thing I could have done. I felt my dick twitch.

“Oh, you like that, huh?” He asked, and I glared at him.

“No”.

He smiled, and squeezed gently, and I groaned. It wasn’t painful, just gross.

He lowered the chair, pushed his hands under my t-shirt and raised it up to reveal my body. His breathing was heavy now, and I could feel his palms begin to sweat as he slid them across my abs and up over my pecs.

“Oh Christ” he moaned, leaning closer and inhaling my musk. “I want you so bad, Mason”.

I clenched my jaw and stared up at the roof as his fingers found my nipples and he began squeezing and pinching. His mouth touched my chest, and for a brief moment, I felt like punching him in the head. What the fuck was wrong with this guy?

He swirled his tongue around one of my nipples, making it hard against my will. I felt my cock twitch again, and dragged my mind to something disgusting. Something more disgusting than this.

With his mouth around my nipple and his hand sliding up and down my crotch, it became almost impossible to prevent my body from responding. I wanted to smack my head off something. How the fuck was I getting hard from this?

“I knew you’d like it, Mason” he breathed, flicking my nipple with his tongue again, “I knew daddy could make you feel good”.

I couldn’t even tell him to shut the fuck up. I was beginning to spill pre-fuck out of my cock, and I dreaded him realising that.

He pulled my shorts down, revealing my white briefs which were now becoming damp with fluids. I let them fall to my ankles, because that was the deal, and I groaned as his hand squeezed and fondled my junk.

“Dont!” I growled, as his creepy hand slid under my ass, “no ass stuff”.

“Oh come on, son” he whispered, still playing with my dick, “let daddy make you feel good”.

His words were like nails on a chalkboard, but I couldn’t deny that the pervert was making me feel things I’d never felt before. At this point, my briefs were drenched.

“Fine” I spat, “but that’s as far as it goes”.

He smiled and positioned me so that I could lift my ass for him. I had a good ass, I’d been told that by plenty of chicks, and evidently, this guy felt the same. He squeezed each globe in his meaty hands, pushing his fingers into the fabric which was the only thing protecting me. He used his thumbs to massage the flesh, and pried my cheeks apart as I drooled more juices.

“Fuck” I groaned, arching my back as he fondled my ass and cock.

My briefs slid down quickly. I managed to grab the front, preventing the weird fucker from seeing my aching rod, and shoved him away.

“Fuck this” I snarled, reaching for my shorts, “you said I could stay in my underwear!”

I almost had my shorts back up when the man frantically reached for the glove compartment and took out two neat piles of cash.

“Two grand!” He said, and I stopped. “I’ll give you two grand, I just got carried away, I’m sorry”.

I stared at the cash, and then at him. Two grand?! Was this guy rich or something?

“Whatever” I mumbled, and sat back down.

“Three” he said, and I was sure I was hearing things, “three thousand dollars if you let me eat your ass”.

Almost instinctively, I let out a sarcastic laugh. “You’re fucking crazy” I told him, and reached for my shorts once more, but then I realised just how much money that actually was.

Three grand would mean that I could sit on my ass all summer. I could have Clarissa over whenever I wanted. I wouldn’t have to spend my days sitting around a pool watching other people enjoy themselves.

“You really wanna eat my ass for three grand?” I asked, expecting him to laugh and shake his head. He nodded instead.

I wasn’t sure if I’d regret it, but the idea of that much money was enough to push me over the edge.

“Alright, fine, but I’m keeping my briefs on, okay?”.

He watched as I turned onto my front and slid the back of my underwear down to expose my plump ass. I could hear him grunt as he jerked his own meaty nub, and shuddered at the idea. Despite that, however, I was incredibly horny.

His hand explored my butt again, only this time there was nothing to protect my flesh from his. He massaged each cheek deeply, pulling and squeezing, scraping and slapping. I could feel more and more pre pouring from my boner, but it was safe and secure.

The man leaned over, his hand still working his meat, and inhaled my ass stench. “You’re real sick for this” I said, feeling his stubble between my cheeks, “wanting to lick my ass? That’s fucked up”.

His tongue ran across my virginal ring, and the pleasure that it shot through my young body made me gasp. I’d never even considered touching that part of myself, but when his tongue slid back down, coating my opening with his saliva, I almost came.

“Fuck” I moaned, squeezing the seat as he did it again, “oh fuck”.

He continued saturating my hole. Slipping, sliding and sucking my unexplored sphincter and making me gasp with each stroke. I wanted nothing more than to grab my eager cock and explode all over his chair, and then I felt it.

His tongue pushed into me, his lips slathered my ring lips and he made out with my butt hole like a passionate lover. I moaned again, louder this time as my body melted with pleasure.

The front of my briefs were now heavy with my cock fluids. I had never been as horny in my life, and the man continued to pump my eager ring with his expert tongue. Over and over again until I shook and found myself on the very brink of the most explosive orgasm I had ever had.

Just as he took me to that magical place with nothing more than his mouth, I felt him tense up, and he gasped, groaned and moaned as he shot spunk onto my chair.

“Oh god” he grunted, when his seed had sprayed all over the place. He fell back onto his chair, panting and exhausted, and dripping with sweat, and I gawped at him.

I wanted to finish. I wanted him to eat my asshole until I shot my load into my briefs, but he was done, and I was three grand richer.

“Thanks” I said breathlessly as he handed me three wads of cash.

“No” he said, still unable to speak properly as he wiped his cock with tissues, “thank you”.

I reached down to pull my shorts back up, but stopped. This guy had just spent all this money and I hadn’t even shown him my dick. I smiled to myself, and turned toward him, then slowly, with his eyes on my drenched crotch, lowered my soaking underwear and let my meaty, thick cock slap against my abs.

“Think of it as a gift” I said, sliding them down my legs and hanging them from my finger, inches in front of him.

He didn’t know where to look. His eyes shot from my bulging rod to my wet underwear, and eventually he snatched them from my hands and held them against his face, inhaling deeply as his cock stirred once more.

“See you around” I said, pulling my shorts on, minus my underwear.

“I hope so” he gasped, and began jerking himself off as I left him in peace.

Perhaps I really was hot.