The Roommate Problem

By Kevin Sting

Published on Aug 8, 2021

Gay

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This and all other chapters of this story are the copyright of the author. (c) 2021. All rights reserved. This is a work of fiction. Any resemblance to real events or real people, living or dead, is entirely coincidental.


We settled on pizza for dinner and Dan hauled himself out of the pool briefly to place our order.

"It should be here in about 45 minutes," he said, emerging from the sliding glass door to the living room. "Anyone want another margarita? Or should we switch to wine in preparation for our pizza?"

"I vote wine," Alex said.

"Me, too," Oscar chimed in.

"Works for me," I added.

"Wine it is," Dan said. "I'll go grab one of the bottles you boys brought."

"I'll help you," Oscar said, rising from the pool. "Plus I need to pee!"

Alex rolled off the chaise and submerged himself fully into the pool. He popped up out of the water next to me and pulled me in tight against him. He planted a soft kiss on my lips, which parted automatically in response. Alex seized the opportunity and slipped his tongue inside.

He massaged my back and butt and I rubbed against the wet hair on his chest.

"This feels so good," he whispered into my mouth.

"It really does," I purred back, fingering his nipples.

Alex pulled away slightly and looked me in the eyes. "I want you inside me tonight, Robbie."

"You what?" I asked, making sure I'd heard him correctly.

"I want you to fuck me," he said slowly, emphasizing each word. "I wanna feel your dick inside me. And I want to feel your cum in me." He looked down shyly and smiled.

I smooth his long wet hair away from his face and held his cheeks in my hands. "I'd love to do that with you, Alex," I said, and then planted a kiss on his lips.

He smiled at me and ground his crotch into my beneath the water. "I can't wait."

"Can we do it out here?" I asked, before realizing what I'd said. "It was so much fun blowing you under the stars last night. I'd love to fuck you outdoors."

Alex gave a huge grin. "Abso-fuckin-lutely!" He went in for another kiss, and we continued making out in the pool for another five minutes or so until Oscar and Dan emerged from the house with the wine.

"Get a room," Dan teased.

"Oh we will NOT be needing a room," Alex replied quickly and gave me a wink.

We hauled ourselves out of the pool. Oscar and Dan smiled as they noted our full erections.

"Ahh, the virility of youth," Dan sighed, handing me a glass and giving my cock a playful squeeze. He handed the other glass to Alex and cupped his balls instead.

We all sat down on the outdoor couches they had set up on the covered patio. Alex pushed one of my legs up onto the couch and then sat between my legs, resting his back against my chest and nestling my erection in the cleft of his butt cheeks. I slipped my arm under his and mindlessly played with the hair on his chest and stomach as we sipped our wine and chatted.

Alex talked about their afternoon outing to the hotel and how amazing it was all looking. Dan divvied up the remainder of the red wine between our glasses and rose to go inside to get another bottle. His cock had plumped up slightly and Oscar gave it a playful kiss as Dan passed him.

Dan was gone for a few minutes. When he returned, he had not only another bottle of wine, but the pizza and salad they'd ordered.

"I didn't even hear the doorbell," Oscar said.

"I noticed the guy coming up the walkway when I went to grab the wine, so I beat him to the bell," Dan said, setting the food and wine down on the outdoor coffee table.

"Did you answer the door like that?" Oscar asked, raising an eyebrow.

"I did indeed," Dan smiled.

"You need to be careful, honey," Oscar said, sighing. "We don't want to be blacklisted from restaurant deliveries for being pegged as perverts."

"Oh please," Dan said, rolling his eyes. "Half of Palm Springs is naked this time of year. And the other half is in a nursing home!"

Oscar shook his head as Dan returned inside and then quickly re-emerged with plates, silverware and napkins. He plopped down next to Oscar on the couch. He rubbed Oscar's chest, squeezed his nipple and gave him a quick kiss.

"He was wearing a Lady Gaga t-shirt, so I'm pretty sure he was not offended," Dan said. "And I gave him a very big tip!"

"Just the tip?" Alex asked, not missing a beat.

"You impertinent little bitch," Dan said in mock anger, reaching across the table to grab Alex's ball sack and giving it a playful twist. We all laughed out loud.

We ate dinner as the sun set over the mountains. Dan and Oscar laid out the plans for the following day. We'd hit up one of the local restaurants for brunch and then do a little shopping. And in the late afternoon, they'd invited several friends over for a BBQ and swimming.

"What can I do to help tomorrow?" I asked.

"Dan will man the grill and Alex is always our go-to bartender when he's in town," Oscar replied. "But if you don't mind being my sous-chef, I could use some help chopping and prepping in the kitchen."

"I'd be happy to," I said, honestly.

"Please tell me you didn't invite Duane," Alex said.

"He's one of our closest friends," Dan said, with a wink. "Of course he's coming."

"Ugh," Alex said, polishing off the rest of his wine. "I spent all evening last time he was here trying to keep his hands off my ass."

"He's just very affectionate," Oscar chimed in.

"Grandma was affectionate," Alex replied. "But she didn't try to slip her fingers in my ass when I was pouring her a margarita."

Dan nearly did a spit-take with his red wine as we all laughed at Alex's comment.

"I've never met Duane, but can you blame him?" I added, sliding my hand down Alex's back and slipping my middle finger between his cheeks. He jumped slightly as we all laughed.

"Don't worry. You'll get in there later tonight," Alex said, and kissed me on the cheek.

Dan and Oscar looked at each other with raised eyebrows.

"Anyone for some mango sorbet?" Oscar said, changing the subject and rising to gather the plates.

Alex stood and took the plates from him. "Yes, but you sit back and relax Oscar. I'll clean this up and get the dessert. Maybe you can show me where it is, Uncle Dan." He gave Dan a little bit of a look.

"Uh, sure," Dan said, rising from his seat. His cock was semi erect and bobbed as he gathered the pizza box, salad container and now-empty wine bottle.

Alex and Dan went inside to the kitchen. I could see them talking intently as they put the dishes and food away.

"Duane's pretty harmless," Oscar said, leaning back on the couch and resting his wine glass on his bare chest. "But I'm sure he'll pay as much attention to you as he has to Alex. He likes the young, pretty ones. But I'll tell him to keep his hands to himself."

"Thanks," I said, laughing. "Will all your friends be naked tomorrow?"

Oscar smiled. "Most of them, yes. Occasionally we have a shy one who keeps his Speedo or thong on. But most of the guys won't be wearing anything -- except maybe a cock ring!"

I could feel my cock firming up again as I sat there listening to Oscar explain the food he had planned for the BBQ the next day.

Dan and Alex emerged from the house, each carrying two bowls of sorbet. Alex plopped down next to me and handed me one of the bowls. For the next 45 minutes or so, we enjoyed our dessert and chatted more about the friends they'd invited for the BBQ.

Oscar set his bowl down on the table and leaned forward. "Alex, why don't you let me give you a massage tonight. You seem like you could benefit from some... relaxation."

Alex smiled. "That sounds awesome."

Oscar stood up, his cock almost fully erect with the head peeking out of his foreskin. "I'll go get everything set up. Why don't you go rinse off and meet me in there in 10 minutes, Alex."

Alex nodded in response. He leaned over and kissed me on the lips and said, "I'll see you later tonight, Robbie." He gave me a wink and then headed inside to rinse off.

Oscar had made his way to the cabana and flipped the lights on, which reflected across the pool and lit up the now dark yard.

"Do you know what time it is?" Dan said, looking out at the dark sky.

I flipped Alex's phone over and tapped the screen. "It's 9:20."

"Later than I thought," he replied. "Mr. Ed'll probably need a walk soon. Wanna take a quick dip and then head out for a walk?"

"Sure, that sounds like fun," I replied.

Dan dove into the pool and I took the steps, slowly submerging myself in the still-warm water.

"It's still like a bathtub," Dan said, after popping up next to me.

"Yeah, it's pretty warm. But cooler than the air temperature, I guess," I said, and then dunked my head under the water.

When I came up for air, Alex was making his way across the yard from the guest room slider to the cabana. He was still naked and his semi-erect cock bobbed heavily as he walked. He waved at me before heading into the light of the cabana.

"Shall we head out for the walk?" Dan asked, slicking his wet hair back.

"Sure," I said. "Let me just dry off and grab some shorts."

"No need for shorts, just put on some flip flops," he said grinning. "I have a special route for warm nights like this."

"You mean you walk out on the street naked?" I asked, making sure I understood him correctly.

"Yes, just for a couple blocks," he said. "And then we'll cut down to a path along a dry river bed -- and around a golf course, if we're ambitious." He set a hand on my shoulder, reassuringly. "Don't worry, I do it all the time. Hardly ever see anyone out this time of night."

"Ok, I trust you," I said.

We got out of the pool and I stepped into my flip-flops. Dan ducked inside the house and emerged in just his flip-flops, as well, with Mr. Ed on his leash.

"We can go out the side gate," he said, motioning to the dark side yard next to the master bedroom. We walked out the gate and emerged next to the house in the front yard.

The street was fairly dark, illuminated only by a dim streetlight several houses down and the moon. I followed Dan out into the street and we passed some of the houses Oscar had pointed out the night before. And then we turned down a perpendicular street that was even less illuminated.

"Nice, isn't it?" Dan asked, giving his cock a playful squeeze.

I nodded and grinned. I had to admit, it was exhilarating being out on the street completely nude. My cock and balls swung freely in the warm air.

Mr. Ed seemed to be enjoying himself, too. He trotted along, stopping occasionally to sniff and/or pee.

"How long have you been doing this?" I asked as we walked.

"A few years now," Dan replied. "I'd do these late night walks all around the neighborhood and often never see anyone. One night I just felt like taking my shorts off for a bit. And then I did it again and again. And then I'd keep them off for longer and longer, until finally one day I just decided to leave my shorts at home."

"Wow, that's ballsy! Literally!" I said, laughing. "What happens when you see someone out on your route?"

"Mostly wave and smile," Dan replied. "I've seen a couple neighbors out and stopped to chat with them. But mostly it's just the occasional runner or cyclist."

"Wow," I said again.

"You've got to remember that this neighborhood is probably 90% gay. And for most of them, this is a second home. So it tends to be pretty quiet," he added. "Not that I haven't been propositioned a handful of times."

"And what did you do?" I asked.

We made another turn and emerged onto a dimly lit path that ran along what looked like a natural aqueduct. I assumed this must be the dry riverbed.

"Well, it's a little hard to go join an orgy when you've got a 45 lb Bassett Hound in tow. But I may or may not have stopped to jerk off with a jogger on a couple occasions," Dan laughed.

I could feel my cock firming up at the image of Dan jerking off with a runner who'd hiked his running shorts down below his balls. "That's pretty hot!" I said.

"It definitely makes life out here a little more interesting," he said, laughing again.

As if he'd planned it, after just a few minutes walking on the path, we saw a runner emerging from the darkness about 50 yards ahead of us. As he approached, I could see he was probably in his 40s, shirtless, with a hairy chest covered in sweat.

"He's friendly," Dan said, reading my silent apprehension.

Sure enough, as the runner approached, he slowed his pace, smiled and said, "Evening. Looking good tonight."

"You, too," Dan said with a smile.

We turned our heads to watch as the man ran past us. He turned and ran backwards for a few paces and grabbed his crotch playfully. Then he turned and continued running away, dipping his shorts down in the back to moon us with a hairy ass.

"Damn, you couldn't make this stuff up," I laughed. "It's like Fantasy Island out here!"

Dan laughed out loud and clutched his bare stomach. "Well it looks like you're enjoying your fantasy," he said, pointing at my partial erection.

I laughed. "Yeah, definitely enjoying it. But I think that's part arousal and partly that I really need to pee. I had way too much to drink tonight."

"Mr. Ed can help you find a suitable bush," Dan said.

"You think it's okay to go out here?" I asked.

"Absolutely. You certainly won't be the first," he replied.

We stopped at a particularly dark spot on the path and I stepped off into the gravel next to it. I grabbed my cock, trying to relax to let the flow begin.

"Hey Robbie, since this IS Fantasy Island, would you be open to bringing one of my fantasies to life?" Dan asked coyly.

"Uh... I guess it depends on what it is," I said, with some hesitation.

"Would you pee on me?" Dan asked.

"You want me to pee on you? Out here?" I asked, taking in the request.

Dan nodded. "No obligation. But I just figured, if you've got to go anyway, maybe you could just aim it at me instead of a bush."

I paused for a minute. "Uh... um, sure. I guess I can do that. I mean, where do you want me to pee exactly? I mean, where on your body?"

Dan kicked his flip-flops off, set Mr. Ed's leash down and knelt in the gravel in front of me. He rubbed his bare chest. (Mr. Ed instinctively lay down on the path.) "My chest. My cock. My face." He smiled broadly. "Depending on how much you have."

"Oh there's a lot," I added.

He smiled again and began stroking his cock. "Great! Whenever you're ready."

I couldn't believe what I was about to do, but I suppose it shouldn't surprise me after all that had happened so far this weekend. I held my shaft lightly, just below the ridge. I took a few deep breaths and willed myself to relax to let the flow begin. After a few seconds, a trickle emerged and landed just below Dan's chest.

"Yes," he sighed.

I relaxed more and the trickle began again. I aimed it a little higher so it landed on his left nipple and pec. The flow increased to a steady stream and I pushed my dick down so the urine hit Dan's cock.

"Fuck, yes," he said.

Now I was fully relaxed and the stream gained in strength. I aimed it up at Dan's face. It splashed off his chin and on to my legs until he opened his mouth. He let the piss fill his mouth and then swallowed some of it, allowing the rest to trickle down his chin and onto his chest and cock.

I aimed my cock like a hose and washed Dan from head to cock in my piss. He rubbed the urine all over his chest and stomach and cock. Then he leaned forward and took the head of my penis in his mouth. As I continued to pee, he swallowed what he could and let the rest run down his face and onto his torso.

I heard footsteps behind me and turned to see the runner had returned. He smiled at me.

"Room for one more?" he asked with a wicked grin.

Dan grunted in approval.

The runner slipped the waistband of his running shorts down and tucked it under his ball sack. His cock was a little shorter than mine, but thicker. He grabbed his cock with one hand and rubbed my ass with the other.

Dan angled his face toward the newcomer's cock and I aimed my stream down his chest to his cock.

The runner seemed to be experiencing a bit of pee shyness. "Let me take these off," he said, before slipping his shorts off completely and tossing them down next to Mr. Ed. He grabbed his cock again and stroked my back. I could feel the wristband of his runner's watch against my skin.

I reached back to massage his furry ass. And then the stream began to emerge from his piss slit. He aimed it at Dan's face and Dan let it spray his lips before opening his mouth to take it in. I directed my dick toward his face again so now he had two streams landing on his tongue.

Dan was feverishly pumping his cock. With his free hand, he pulled the runner in until our dick heads were touching. And then he leaned forward so that both of our piss-spewing cockheads rested on his tongue. He let out a grunt and I felt his hot cum land on the top of my foot.

"Fuck yeah!" the runner moaned. He was tugging at his nipples and massaging my ass.

Our streams subsided. He grabbed his cock, which had grown to full erection, and began stroking it.

Dan shifted over onto the path and laid on his back. The runner stepped over and straddled him. Dan held his softening cock and I could see that a stream of piss was now emerging. He sprayed the stream up over his stomach and chest as the runner jerked off above him.

I rubbed the runners ass and he squatted lower, parting his cheeks. Accepting the invitation, I shoved my middle finger between the damp, furry cheeks to find his puckered hole. He moaned as I pressed against it and then quickly entered him up to my first knuckle. I pushed in and out as he stroked until my finger was buried entirely.

"Oh fuck," he moaned quietly as his asshole clamped down on my finger and he began shooting cum all over Dan's chest and face. I slowly let my finger slip back out as he let out another moan.

He turned and gave me a full-bodied, sweaty, cummy hug and kissed my cheek. "Thank you stud!"

"And thank you, too, Brandon!" Dan said, grinning from below us on the path. "It's always so nice to see you out."

"Looking forward to the BBQ tomorrow," he said, smiling. "Now can I take care of that monster, my young friend?" He grabbed my erection.

"Hands off," Dan said. "He's saving that for my nephew's ass tonight."

"Lucky nephew," Brandon said, hugging me again and squeezing my ass cheeks. "Will you both be at the BBQ tomorrow?"

"Yes," I said, stunned.

"Can't wait to see you both and hear about your evening," he smiled. He reached down to grab his shorts and then pulled them on. Then he extended a hand to help Dan up. "I'll see you boys tomorrow." And then he turned and ran down the path again.

Next: Chapter 18


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