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I relaxed naked in the heat of the late afternoon, my pale skin protected by the patio umbrella. Jerry prepped his massage table for his client, removing the sheet that I'd been writhing on while he brought me to climax just a few minutes before.
Jerry was naked, as well. His erection bounced freely as he worked, the sunlight catching the silver hoop that went through his piss slit and pierced through the underside of his penis.
I was beginning to doze off when I heard a knock on the gate. Jerry walked over to the gate, unlatched it and welcomed his client into the backyard. He gave the man a quick hug and a peck on the cheek before relatching the gate.
"Kyle, this is Tyler, Philip's assistant and house sitter for the next month," Jerry said as he guided his client towards the guest house patio.
"Pleased to meet you, Tyler," Kyle said extending his hand to me.
"Likewise," I said, taking his hand and shaking it.
"Once you're undressed, Kyle, you can rinse off in the bathroom or out here if you prefer," Jerry told him. "It's just us boys today without Daisy here."
"Cool," Kyle replied. He sat down on the chaise next to me and began to unlace and remove his shoes. "You're the artist, Tyler, right?"
"Yes. In my spare time, at least."
"I've seen your paintings in the living room. They're beautiful," he said as he pulled off his socks, tucked them into his shoes, and then began to unbuckle his belt. I guess I was about to get a front row seat to his undressing.
"Thank you," I replied. "Philip and Daisy have been really supportive of my work."
"We've got to show you the portrait he did of Philip," Jerry chimed in as he draped the massage table with a fresh white sheet.
"I'd love to see it," Kyle said smiling. He slid his chinos off and then pulled his polo up over his head, folding them both neatly and laying them on the chaise. He stood up, hooked his thumbs in the waistband of his boxer briefs and slipped them off, depositing them on top of his other clothes.
From my seated position, I was eye level with his cock, which made up in girth what it lacked in length. It was nestled in a thick bush of copper pubic hair that contrasted with his pale skin.
"Are you Scottish?" I asked.
"Yes," he said smiling. "How'd you guess?"
"Just a hunch," I said winking and casually running my fingers through reddish-brown wisps of hair above my cock. "Me, too."
"Duh. Ginger twins!" he laughed.
"You've got me beat in the ginger department," I said, eyeing the copper hair that lightly covered his entire body. "But I think we're tied in the milky white skin category."
"True that," he laughed again. "But you clearly have me bested in the sausage department!"
I blushed and Jerry laughed, "You can't argue with the truth, Tyler."
"Sorry, I didn't mean to make you uncomfortable," Kyle said sheepishly.
"Don't worry about it," I said smiling up at him. "I wouldn't be laying here naked if I was uncomfortable."
Kyle smiled back at me, relieved. "Can you show me your portrait of Philip before I rinse off?" he asked.
"Sure," I said beginning to rise from the chaise. Kyle extended a hand and helped me stand. Standing next to him, I could really assess our similarities and differences. We were almost the same height; he maybe had an inch on me. But he was stocky, probably at least 40 or 50 pounds heavier than me. He had a light, but overall covering of red hair, whereas I was pretty smooth save for the wisps at my armpits and groin and the faint covering on my legs. His cock was circumcised and I was uncut. And I'd guess he was in his mid 30s, about 10 years older than me.
"It's just inside the master bedroom," I said, gesturing towards the French doors near the back of the property. I headed that way and he followed close behind.
"I've been inside the main house a couple times, but never this far back," Kyle said as we approached the doors to the master. I pushed them open, startling the dogs who were lazing on the unmade bed. They looked up at us and then all returned to their positions reclining in the warmth of the afternoon.
We walked into the bedroom and I guided Kyle to Daisy's side of the bed where the nude portrait of Philip was hung. I'd painted him standing in the shallow end of the pool, cocktail in hand and full of confidence.
"Wow, this is terrific!" Kyle exclaimed. "Philip is quite a DILF, isn't he?!?"
"Thanks. Yeah, I guess he is rather DILF-y," I laughed.
"Jerry said he skinny-dips quite a bit in the pool, but he's always been in tennis gear or work clothes when I've seen him," Kyle said mindlessly scratching his balls with one hand. "I need to schedule my massage appointments to coincide with Philip's swimming."
"I'll see what I can do," I laughed.
"Oh right," Kyle laughed, remembering who I worked for. "Was it weird for you painting your boss nude?"
"A little at first," I replied honestly. "But it wasn't the first -- or last -- time I'd seen him naked. And it felt fairly natural after awhile. At his invitation, I ended up taking my clothes off, too. We swam, ate lunch, chatted, and I finished up the paining all while we were both nude."
"Wow, that's hot!" Kyle said. His hand was now lightly caressing the shaft of his dick. "It sounds like something you'd read about on Nifty's Archive."
"I guess it kinda does. But it felt pretty nice and wholesome at the time," I laughed, eyeing Kyle's cock, which was now beginning to firm up into an erection. "We better get you back outside so Jerry can work his magic on you."
"Right," he said, giving his hard on a couple last squeezes.
We walked back outside and Kyle proceeded to the outdoor shower on the wall of guest house to rinse off. I headed over to Jerry.
"I see Kyle enjoyed the portrait -- and/or the artist!" Jerry laughed. I gave him a playful slap on his bare ass."
"I'm going to go feed the dogs and check Philip's email," I said. "If you don't have dinner plans, Daisy left plenty of stuff in the freezer for me."
"That sounds lovely, Tyler. Do you mind if I extend the invitation to Kyle, as well? I don't think he has much of a social life right now."
"Not at all," I replied. "He seems like a nice guy."
"Perfect, we'll be done in about 90 minutes. Now don't go jerking off to Philip's naughty photos without me," he added with a wink.
I shook my dick a couple times and then abruptly let it drop. "I promise! Enjoy your massage," I yelled over to Kyle, who waved back at me. I headed into the kitchen and prepped the dogs' food. Then I grabbed my laptop and headed into the den. I spent the next hour and a half sorting, deleting and replying to Philip's email. Thankfully there were no major crises at the studio.
The sun was just starting to set outside and the heat had subsided. I strolled outside, naked in the warm twilight, and could see that Jerry was near the end of Kyle's massage.
Kyle was on his back, with his fat erection resting against his pubic hair. Jerry was kneading the massage lotion into his beefy pecs and was drenched in sweat.
"Ahh, Tyler," he said quietly. "Your just in time for the big finale. You don't mind an audience, do you Kyle?"
Kyle opened his eyes sleepily, looked up and me and grinned, "Not at all."
Jerry pumped another glob of lotion into his hand and stroked lower down Kyle's torso. The sequence seemed to repeat what he'd done to me several hours earlier. He rubbed his hands in circular movements around Kyle's stomach, getting closer and closer to his pubic area with every rotation. Kyle's erection began to pulse and raise upwards. I could feel my own cock begin to swell.
Jerry ran his fingers through Kyle's pubic hair, caressed his balls, and then began to gently stroke his cock. He looked over at my growing erection and smiled. "Feel free to join in, Tyler. Four hands are better than two."
Again, Kyle's eyes fluttered open and he smiled at me. I edged closer and extended a hand toward his chest.
If you'd asked me what my "type" was, I wouldn't have described anyone like either Jerry or Kyle. But standing next to these two naked men, my cock began to throb and leak a bit of precum.
I stood behind Kyle's head and reached over to run my hands over his fuzzy chest. I let my fingertips run over his pink nipples and they firmed up at my touch. I tweaked them gently and then harder as he moaned.
My erection was fully extended. Given my position, there was really no where for it to go other than to rest against Kyle's face. When he felt my cock brush his cheek, he instinctively turned toward it and extended his tongue to greet it.
"Beautiful," Jerry purred, stroking Kyle's cock with one hand and his own with the other. "Suck that thing, Kyle."
Kyle did as commanded, opened his mouth and began to suck my cock.
Then Jerry surprised me by climbing up onto the table with Kyle. He straddled Kyle's thighs and brought their cocks together and pumped them in unison. Then Jerry pumped out another handful of lotion, reached back towards his ass, and rubbed the lotion between his cheeks.
I had rotated around to one side of Kyle's head give him better access to my cock. He slurped and licked and sucked on it as my balls slapped against his cheek.
Jerry shifted up onto his haunches and then positioned himself over Kyle's erection. He grabbed Kyle's cock and slowly lowered himself onto it, taking the fat member into his ass.
"Oh yeah," we all three exclaimed, nearly in unison.
Jerry began to rhythmically bob up and down on Kyle's cock, while Kyle continued to service my own cock. I reached over and grabbed Jerry's erection to complete the circle of service. We synchronized our fucking and pumping and sucking, working up a sweat in the still warm evening air.
After several minutes of three-way action, Jerry was the first to begin to climax.
"Oh fuck," he cried arching his back as a shot of white semen emerged from his cock and landed on Kyle's chest. As Jerry released several more shots onto his chest and stomach, Kyle let out a moan, muffled by the presence of my cock in his mouth. He raised his ass off the table and pounded his cock into Jerry's ass harder and harder. And then he froze in the air as he shot his load into Jerry's ass.
I continued to fondle Jerry's softening cock, letting my fingers play with his Prince Albert piercing. Cum continued to dribbled over the silver hoop, and I could feel my second load of the day ready to be released. As Kyle continued to pump into Jerry's ass, he sucked harder on my cock.
Feeling my impending orgasm, I started to pull my dick out of his mouth, but he hungrily sucked it back in. So I relented and let loose. I pumped shot after shot into Kyle's mouth until it began to seep out around my cock and over the corners of his mouth. I let my dick slip out of his mouth and slide against his cheek.
Jerry lifted himself off Kyle's cock and began to lick his own semen off Kyle's chest and stomach. I used my fingers to gather globs of it off of Kyle's chest and fed it to Jerry. Then Jerry leaned over Kyle's face and let the mouthful of cum fall into Kyle's open mouth. He leaned down to kiss Kyle, letting his tongue explore the two loads of cum. Then Jerry reached over and grabbed my softening cock and licked off the last bits of cum that dribbled from it. He kissed Kyle again, and finally Kyle swallowed with an audible gulp, letting the cum slide down his throat.
I could see Kyle's semen begin to leak out of Jerry's ass and onto his balls. I reached back and scooped up the cum and caught the remaining globs that oozed out. And then I brought my hand to Kyle's face and let him lick his own cum off my fingers.
Jerry bobbed his head down again to get in on the action, licking greedily at my fingers. And then he kissed Kyle again. I reached back to ensure I'd gotten all of Kyle's cum. Jerry's ass was warm and loose, so I let my index finger slip inside to ease out any residual cum. I brought my finger back to Jerry and Kyle, who promptly licked it clean.
"That was lovely. Now who needs a drink?" Jerry exclaimed hopping off of Kyle.
"Me!" Kyle said exhausted.
"Ditto," I replied, rubbing the sweat into my chest and stomach.