Being a Pool Boy has Its Perks

I parked my van in front of the large mansion and turned it off. It was the third and final pool cleaning of the day, and I was hoping to get it done fast to get out of this sweltering heat. I had worked at the pool company for a few years now, and I had a list of loyal customers who liked me specifically because I did such a thorough job.

On Wednesdays it was the Carter family, the Sampsons, and then finally Mr. Winsfeld. Cleaning the pools of millionaires was a good paycheque, and the outdoor work kept me in pretty good shape.

Unfortunately, my girlfriend, Laura, and I had broken up this past weekend, and I was forced to do my absolute best to keep my customer service face on and not let it show that I was upset. Rich people hate it when their staff aren't happy, and usually a smiling service got me a good tip.

I let myself in through the side gate and carried my supplies to the back yard. The pool was at the base of a large marble staircase, with a huge sprawling acreage in all directions around it. I got my tools ready and set off to work.

As usual, about halfway through cleaning his pool, Gavin Winsfeld meandered out to the poolside and laid down in one of the white lounge chairs. He was in a cool linen shirt and one of those speedo bathing suits, with flip flops and sunglasses. I wasn't sure how he was so rich at that age, and assumed it must be family money or something. I didn't ask, in our line of work it was frowned upon to ask.

I smiled and waved, and he shot a smile back.

"Doing good work, seems like you're ahead of schedule!" he called over.

"Thanks!" I replied, pushing the brush along another section of the bottom. "Not too many leaves today so it's been good."

As I got back to work he started playing some music on his phone. Out of the corner of my eye I saw him take off his shirt and start putting on sun tan oil. Most clients didn't like seeing how the hotdog is made so to speak, but he didn't seem to care. He usually tanned during the last half of my work and then went for a swim as soon as he was done. He was a good client, always paid on time and always slipped me a good tip in cash.

He was a good looking guy, around 30, mostly hairless and on the thinner side, with a lean, toned body. He clearly did not skip glute exercises though because he had an ass that would make most women I knew jealous. Once he was all oiled up he set the lounger flat and laid on his back.

About half an hour later as I finished up he called over, "Hey, do you have anywhere to be right now?"

I stopped, glancing at him. He had flipped over a little while ago and was lying on his stomach, letting his backside get some sun. I thought for a second, and shook my head, "No, you're my last one of the day, why?"

He smiled. "You did such good work and it's so hot today, why don't you hang out for a bit? There's some beer in the bar fridge if you don't mind grabbing us both one, and you're welcome to join me for a swim after."

Normally I was in a rush to head home, but with Laura gone I didn't see why I shouldn't have some relaxation time.

"Yeah, sure." I walked behind the bar and grabbed two fancy beers from the mini fridge, and then headed over and sat on the lounger next to him. He smiled as I passed him one of them, placing it on the ground next to his lounger.

"So what's new with you?"

I stared at the pool and took a swig of beer. "Eh, not too much."

"You sure, you've had a bit of an, uh..." he waved one hand around in the air, trying to find the word he was looking for. "I don't know, like, a funk about you today."

"Ah, jeez, I didn't think I was letting my customer service front slip that much," I chuckled, taking another sip. "Just went through a bad breakup, that's all."

"Ah," he gave me a sympathetic smile "Sorry to hear that."

"Eh, it's ok." Another sip. "It hadn't been very good for a while now."

"Sex was bad, huh?"

I spluttered my drink in surprise, coughing a bit. "I- uh... um..."

He laughed, "Sorry, was that too bold? I have a bad habit of doing that."

Once I got my composure back I waved a hand at him. "Nah you're good, I'm off the clock so this is just us hanging out or whatever, right?"

He let out another laugh, and propped himself up on his forearms. Doing this caused his backside to arch and his ass to stick out just a bit more. As he took a sip of his beer I caught myself zoning out and glancing at his ass. It really did look like a woman's ass. I snapped out of it and swung my head the other way. Geez, that beer must be hitting me more than I thought. I realized that my dick had gotten a bit of a chub and adjusted myself a bit to make sure it was hidden.

"I mean, if you don't care about me being a bit TMI..." I cocked an eyebrow at him.

"Go for it," he smiled again.

"Yeah you hit the nail on the head. We hadn't had sex in months. We had a fight about some stupid thing and then we weren't having sex but then the sexual frustration made us both more irritable and so on and so on until it all just kind of came to a head, y'know?"

He let out a hum of agreement. "I've had that happen, it's a vicious cycle." He laid back down fully.

We settled into a comfortable silence for a bit. I kept catching myself glancing at his ass, and hoped he didn't notice. God, I needed to get laid so bad. I shifted again, realizing my chub had gotten a bit bigger. I convinced myself it was just because I was thinking about women with asses like that.

"Want another beer?" he asked.

"Yeah, sure."

He stood up from the chair and walked behind the bar. When he returned he stood next to me, his crotch right around eye level with me. The speedos didn't exactly leave much to the imagination and I tried to not look at it as I accepted the cold can and popped it open. He walked back around to his chair and bent over to grab his towel. His ass was directly in front of me and I felt my dick jump a bit. I was always an ass man and goddamn his ass looked so much like a woman's ass that it was fucking with my head. I thanked god I was in loose shorts so he wouldn't be able to see anything. The last thing I needed was him complaining to my boss that I popped a boner at his house.

He straightened back up and turned to me. "Ready to swim?"

"Oh, uh... I don't have a suit."

"Oh..." his face took on a thoughtful look, before looking me up and down and suddenly brightening up. "Hm, you seem to be similar size to me, you could borrow one of mine?"

"Uh... sure."

"Great!" he burst into a big grin, turning on his heel to walk over to the house. This gave my dick some time to calm down finally and by the time he returned with a small bundle I was back to normal. He passed me the bundle. "Feel free to change in the pool house, see you in a minute!"

I grabbed the bundle, which seemed to be an expensive, thick towel with a bit of a bathing suit poking out of the middle, and walked over to the pool house. I shut the door and unwrapped the towel on the table. Then I froze.

It was another speedo.

I wasn't exactly ashamed of my body but I had never really had the courage to wear anything like this. Normally I would have just turned down the offer to swim and gone home, but he was being so nice and it was just so damn hot. I psyched myself up and slid off my work polo and khaki shorts and my boxers and slid on the speedo.

It was a bit snug, but not uncomfortable. It sure didn't leave much to the imagination though, and I tried to position my dick in a way that wasn't too showy. I left my clothes on the table and walked out with the towel.

When I got outside Gavin was already swimming laps. I dropped the towel on the lounge chair and walked to the edge of the pool. He surfaced and looked over at me, his eyes noticeably widening.

"Looks like it fits well, huh?"

I flushed a bit, "Uh... yeah. Thanks again."

"Do you want any goggles or anything?" he asked, climbing up the steps towards the plastic chest outside the pool house. Before I could answer he opened the lid and bent over to look for them amongst a pile of pool noodles and flippers and beach balls. He bent all the way over to reach to the bottom, putting his ass on full display.

I felt blood start to rush to my dick again. I tried to will my dick down, but it had a mind of its own. I glanced down and to my horror realized it had gotten big enough to start to push the edges of the speedo away from by body a bit. I quickly sat down and covered myself with my towel.

When I looked back up towards him I realized he was looking at me, his head cocked to the side a bit and a questioning look on his face. I felt my own face get hot, and I grabbed my beer and took a big swig in the hopes he would think I was just sitting down to finish my beer first.

He turned around, digging back into the chest again. I could have sworn he was arching his back slightly, his round cheeks spreading slightly. My dick kept going, straining against the speedo. I looked at the ground and tried to think about anything I could to get it to calm down, to no avail.

"Found them!" He walked over to me and held out the goggles. "Everything ok?"

"I- uh yeah I uh..." I stammered. My face even more red than before. I reached for the goggles and realized he was holding them just out of reach. He cocked his head again, a coy smile on his face. Was he onto me?

For some reason the idea of him catching me made me rock hard. The speedo strained against me, pulling tight at the sides. I had always been a bit of an exhibitionist, but this was a guy. I wasn't into guys.

Right?

"You coming?" He took a step further and handed me the goggles, before turning around and walking to the deep end and diving in. Before he had a chance to surface I quickly walked to the edge and slid into the shallow end. At least if I was in the water he shouldn't be able to see and I could get my sex deprived mind to finally calm down.

I sat on the stairs and he swam over to the shallow end. He walked to the side of the pool and pulled himself up just enough to reach over and grab his beer. His ass was just above the water line, directly in front of me. Fuck.

After a sip he lowered himself back in and walked over to sit next to me. "Anyways it's her loss."

"Hm?" I looked at him, confused.

"Your ex. Seems she couldn't tell when she had a good thing." He smiled again.

"Oh," I didn't really know how to respond to this. "Thanks."

"Anyone with half a brain would be fucking you daily if they had the chance." Before I could even register the comment he launched himself forwards and took off in a front crawl. Was he hitting on me? Was he just being nice? Between the sun and the beer and my horniness my brain was just kind of fuzzy.

When he came back he popped over the edge for another sip of beer. This time I couldn't really control myself and stared at his ass. It was so fucking perfect. He hoisted himself up fully and laid down on the lounger ass up.

"Could you grab me one more beer, please?" he smiled at me, and I could swear it was a bit of a devilish grin. I couldn't think of any reasonable excuse and nodded. I quickly turned and darted to the bar, trying to tuck my dick down as best I could before grabbing two more beers and walking back to the chairs.

I wasn't totally sure what exactly was going on anymore. I wasn't straight, I didn't really know Gavin's deal, and yet it seemed like he was showing me his ass deliberately? Was he flirting with me? And did I like it? Was it the beer and the sun, or was I just that sex starved? But two beers was usually only enough to get me barely buzzed, so was it even the beer at all?

I was so lost in thought I didn't really realize that I had walked over to him with my speedo still straining, and my dick was hanging above his head. He seemed to pretend not to notice and took the beer from me with a smile. I sat down on my lounger.

"So have you gotten yourself any rebound fun?"

"No, haven't had the chance to, really." My dick throbbed a bit at this question. Was he coming on to me? Did I want him to?

"That's no good, you should really fix that!" He propped himself back on his elbows and seemed to push his ass up just a bit. "It's no good to deprive yourself that long!"

"Yeah..." I felt myself getting lost in a horny haze, not really able to look at anything but his round, soft ass.

"And it seems like your little friend agrees with me." He was staring at my crotch, the speedo fully pulling away at the sides so you could see a bit of my shaft and my balls. He looked up at me, smiling. "I think you should listen to him."

He swivelled around and stood up, and in that moment I could tell he was hard too. He walked over and dropped to his knees in front of me.

"Should I listen to him, too?" he asked, his head cocked and a smug smile on his face.

"Yeah."

The word left my mouth before I knew what I was saying. He pulled the front of the speedo down, freeing my dick from its spandex prison. It bounced up so hard it slapped against my belly. He pulled the speedo down just under my balls and let go of it.

"He seems to know what he's talking about." With that he grabbed my dick and gave the bottom of the shaft a tentative lick. A jolt of pleasure shot through me and I let out a little whimper. He smiled and ran a long, slow lick from by balls to my tip. By this point I was absolutely leaking precum, and he lapped it up. Then he wrapped his lips around my head and started to sink down.

"Fuck."

It had been so long since I had gotten my dick sucked, and he was clearly no amateur. He made it to the base with no issue, almost showing off his lack of a gag reflex. I let out a moan. I don't think I'd ever had a girl suck me off this seamlessly. He started to bob up and down rhythmically. Usually with women it was like a chore for them to suck dick, but Gavin was sucking it like I was giving him a gift by letting him.

He kept sucking me off until I felt a familiar sensation start to build. "I- I'm getting close," I managed to stammer out.

Hearing this, he pulled off and backed away completely. I let out a little whimper at this, my balls starting to ache a little bit.

"Well let's not get ahead of ourselves then," he said, walking back over to his chair and hooking a thumb in each side of his speedo. He pulled it down, bending over and putting that big, glorious ass directly in my face. Without thinking I reached up and laid a hand on one of his cheeks. It was firm yet soft. So, so perfect. Had I ever seen an ass this good? I didn't think so.

"You seem to like looking at it so much I would hate to deprive you." He smiled over his shoulder, still bent over. "Tell me, did this ex ever let you fuck her ass?"

"No, women don't usually enjoy anal." The effect of the conversation was that the building orgasm had subsided, but my dick was still rock hard.

"Her loss!" With this he kicked off his speedo fully and laid down again on his lounger, his dick tucked up under him and his hips raised just a bit. I didn't need an invitation to know exactly what he was getting at.

I stood up, kicking off my own speedo, and walked over to his chair. I kneeled just behind him and let my dick rest gently between his cheeks, grabbing his hips. He held the bottle of sun tan oil over his shoulder and I drizzled it onto his ass. I kept thrusting gently, letting the slick oil coat my dick and his crack, pushing between his cheeks ever so slightly.

Then I pulled his hips up and angled my dick down and placed my head against his hole. I couldn't even think of stopping, the lust taking complete hold of my brain. I pushed gently, and felt him open up slowly to take me. When my head popped in he let out a low moan, and started to slowly push back against me. After about a minute we had managed to sink my dick all the way inside of him.

"Fuck, Kyle, your dick is so good." He started to slowly move himself back and forth, letting himself adjust to me.

"Your ass is so fucking sexy, fuck."

Once he was ready I grabbed his hips and started thrusting. Slowly at first, but with an increasing need. His tight, warm hole felt so good, and it was taking everything in me not to just blow my load right then.

I realized being on this lounge chair wasn't an ideal position and pulled out, throwing a towel on the ground and motioning him towards it. He got the idea and got on all fours, and I took my place behind him. This time I slid in easily, really able to get a good thrust going. Gavin was moaning loudly, clearly enjoying himself. I was very thankful rich people had big enough yards that nobody should be able to see or hear us.

I picked up my pace even further. The only sounds were my grunts of effort, his moans, and the gentle slapping of my thighs hitting his perfect ass.

I realized that I had held off as long as I could and felt that feeling start to build again.

"I- I'm gonna cum." I moaned.

"Fill me up then," he moaned back. This pushed me over the edge, and with one final push as deep as I could, I felt the wave of my orgasm break over me and my dick started pumping cum deep inside him. Burst after burst, I wasn't sure I had ever cum this much or this hard. I stayed in him, grunting and panting and sweating as I unloaded completely, and then I slid out and laid back down on my lounger, my cum coated dick still out to the open air, my energy spent.

He had laid down on the towel on his back, and looked up at me with a lust hazed expression. "Mind if I finish myself off?"

I just nodded and he started to jack off, occasionally thrusting his hips upwards, clearly putting on a show for me. I laid there, transfixed. He kept going until I saw his balls tighten up and he burst, letting out a loud moan when he did. I watched as shot after shot flew out, the first coating his face and getting in his open mouth, the next few covering his chest in a thick coating. Once it was finally done he collapsed to the ground and smiled up at me.

"Feel better?"

I smiled sheepishly. "Yeah," I replied.

Once we had caught our breath we decided to clean ourselves off with another dip in the pool. It didn't take long for me to go up behind him, my dick ready for another round, and push him up against the side of the pool. He lifted one leg a bit and I was able to angle myself back in. This time I was pretty spent, so I fucked him nice and slow, really enjoying it.

I knew now that obviously I wasn't as straight as I thought. But I didn't really care. Gavin had introduced me to a side of myself that I didn't know was there, and fucking him tenderly was my way of saying thank you without saying it. I came inside him fully pressed against him as much as I could, moaning gently into his ear.

Once we had finished he took me to the small outdoor shower off the pool house. We both went in and we made out under the cool water for a long while. Then we dried off and I got dressed.

"Same time next week?" he asked, lounging still naked on his chair.

I planted one more kiss on his lips.

"Sounds like a plan."