The Roommate Problem

By Kevin Sting

Published on Apr 23, 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 enjoyed our bagels, fruit and coffee naked on the patio. Oscar and Dan probed me more about my family and my job. Oscar's eyes lit up when I told them I got a sizeable employee discount off merchandise and would be happy to go shopping at the local store so they could take advantage of it.

I asked them about how their life in Palm Springs compared to LA. "Hotter than hell, but definitely more relaxed," was the gist of their response. We talked a little about Shannon and a couple of other girlfriends Alex had had.

"Okay, so I've had lousy taste in women," Alex said, placing a hand on his bare chest. "Hopefully my taste in men is better." He put his other hand on my shoulder and squeezed.

"Without question!" Dan laughed and squeezed my bare thigh.

After finishing our breakfast and clearing the table, we all took a dip in the pool. The sun was already getting intense, so we didn't stay in long. None of us bothered with towels since the heat dried us off almost instantly.

We agreed that after getting showered and dressed, Oscar and I would drive "in to town" for a little shopping spree.

Alex and I headed into the guest room and through to the bathroom to shower. He turned the water on in the large walk-in shower and stepped inside. I peed and was about to walk back into the bedroom until he was done, when Alex said, "Hey, there's plenty of room in here for both of us." He raised his eyebrow as he said it.

I smiled and stepped into the shower with him. He pulled me against him under the rainfall shower head. He pressed his lips against mine and I could feel his tongue dart out. Parting my lips slightly, his tongue found mine, and we began to kiss passionately. He clenched my butt cheeks and ground his pelvis into mine.

And then he surprised me by dropping to his knees and taking my rapidly stiffening cock into his mouth. I collapsed backwards slightly until my back was against the shower wall. I ran my hands through the long, thick, wet mass of Alex's hair, while he bobbed up and down on my erection.

Alex slipped a hand under my balls and tugged on them playfully. And then he wedged his fingers into the cleft between my ass cheeks. His middle finger found my hole and he began to massage around it. After a few minutes of teasing the hole, I relaxed a bit and Alex's finger slipped inside. I gasped at the sensation.

Alex pulsed his finger in and out of my ass in unison with his sucking. It felt amazing.

"Hey Alex, I'm going to head over to that hotel that's being refurbished," we could hear Dan's voice from around the corner in the office. We'd forgotten to shut the door again. "Do you want to come with me while Oscar and Robbie are shopping?" He popped into view in the doorway, still naked. "Oh my! Sorry to interrupt."

Alex pulled his mouth off my cock. "No worries," he said, nonchalantly while still kneeling in front of my cock with his finger in my ass. "Yeah, I'll go along with you. We'll be done here soon." He looked up at me and winked as he pressed his finger against my prostate.

"Take your time," Dan said smiling, and then slowly retreated to the office.

Alex took my cock back in his mouth and continued to press my prostate. It was too much, and I began to unleash another load of cum into his mouth. Alex dutifully swallowed it all and then rose to kiss me again.

The taste of Alex's mouth and my own cum was intoxicating. I dropped to my knees and returned the favor for Alex. His cock was hard as a rock and I could feel every bulging vein on my tongue. I nibbled lightly on his engorged glans and used my tongue to gently pry open his piss slit so I could taste his precum.

I reached behind Alex and grabbed his lightly furry ass cheeks with both hands. I kneaded them, squeezing and separating, squeezing and separating. Eventually I let my index finger slip between his cheeks to find the hairy pucker of his asshole.

Alex gasped quietly. His glutes and sphincter tightened, but then relaxed the more I rubbed my finger around his ring. Still servicing his cock with my mouth, I pressed my finger tip against his asshole and pushed gently until it slipped inside him.

Again, he gasped, this time louder. "Oh fuck, Robbie!"

As the words spilled out, his muscles relaxed more and I pushed my finger deeper inside him. He grasped my shoulders tightly, his fingers digging in to my bare skin.

I began to pull my finger back out. But before the tip emerged, I pushed it back inside him. I did it again -- retreat, advance, retreat, advance -- increasing my speed slightly with each repetition.

Alex now had both hands on the back of my head and was pushing me down on his cock.

"Fuck this feels so good, Robbie," he moaned, as the warm water continued to spray over us.

I twisted my finger around and found the bulb of Alex's prostate. Mimicking what he'd done to me, I began to gently press and massage the gland as I sucked harder on his cock.

Alex's body began to shudder. He slammed my face further down onto his cock until my nose was smashed against his wet pubes. His torso arched forward as he began to fill my mouth with blast after blast of his semen.

I almost got to the point of not being able to breathe, but Alex finally released his grip on my head and collapsed back against the shower wall. I slowly pulled off his cock, licking the head to ensure I'd captured all his seed. And then I gently slipped my finger out of his ass.

"Ohh!" Alex gasped at the feeling of my finger sliding out.

I rose from my knees and kissed him again.

Alex pulled back slightly and whispered into my mouth, "That felt fucking incredible, Robbie. Thank you!"

"My pleasure," I purred and squeezed his chest and tweaked his nipples gently.

We spent another 10 minutes in the shower, alternately kissing and lathering each other up. Once we were sufficiently clean, we stood in the shower kissing and toweling each other dry.

As we stood naked in front of the mirror applying deodorant and our respective hair care products, Alex looked at me and giggled. "This is gonna sound really weird, but I feel like I just took the BEST shit of my life." I laughed out loud and I heard Dan snort from the office. "PERV!" Alex yelled playfully toward the office.

"Yeah, ass play can feel like that sometimes," I said.

"I had no idea," Alex said, wide eyed and smiling.

"I hope it was okay. I figured since you ventured south first, you were up for it," I said.

"Yes, yes it was more thank okay," he replied and planted another kiss on my lips.

"I suppose we should get dressed now," I said. Alex nodded.

"Hey Alex, when you have a minute, I have a tech question for you," Dan said from the office.

Alex hung his towel and headed in to the office naked to help his uncle.

I made my way into the bedroom and pulled on a pair of yellow shorts and a brightly colored madras plaid shirt. I could hear Alex and Dan discussing security settings. Within a couple minutes, Alex joined me in the bedroom and got dressed in tan shorts and a white polo that made his skin look like caramel. I noticed that he didn't bother wearing underwear and was glad I'd done the same.

We walked out to the living room and relaxed on the couch for a few minutes. Mr. Ed took the opportunity to solicit some belly scratches.

After a few minutes, Dan walked out of the office, still naked. "Oh, I thought you boys might need a nap after all that... uh... exertion," he said, winking at us. "Let me go throw some clothes on and I'll see if Oscar has completed his beauty regimen."

Alex wrapped his arm around my shoulder, leaned over and planted a soft kiss on my lips. "I'm getting used to this," he whispered.

"Me, too," I said, smiling.

Within a few minutes, Dan and Oscar emerged from their bedroom dressed and ready to go. We all proceeded into the garage, where Alex and Dan climbed into Dan's SUV and Oscar and I settled in to his BMW. Oscar and Dan backed their respective cars out of the garage and then we were on our way to our errands.


On the 30-minute drive to the store, Oscar shared some juicy stories from his career doing makeup and he asked me about my journey out to California. Eventually the subject returned to Alex, and I mentioned what Dan had said about catching him jerking off as a teen.

"Ah yes, I remember how freaked out Dan was telling me about it," Oscar laughed. "It certainly helped prep me for when the same thing happened to me a few days later."

"Oh, do tell," I said.

"Similar scenario to Dan's. I came home from work and Alex was naked and jerking off on the couch," he said. "I just greeted him and went about my business for a little bit. Eventually I got myself a drink and joined him in the living room."

"Naked or clothed?" I asked.

"Just shorts and a t-shirt," he replied. "I asked to see what he was watching and he showed me the low-quality porno he had on. I told him we had better quality stuff and showed him where we kept our stash in the TV cabinet. It was mostly gay DVDs, but there were a couple bi-themed ones that had women in them. He popped one in and returned to his business."

"Wow, all while you were sitting there?" I asked.

"Yes. I started to get hard, too, of course," Oscar grinned. "I asked him if he minded if I jerked off, too."

"Really?" I asked, wide eyed. "What'd he say?"

"Indeed," Oscar laughed. "He just said, 'Yeah, that's cool.' So I stripped off and we jerked off together."

"Damn, I wish I'd had relatives like you growing up," I said. "Was there any touching? If you don't mind my asking."

"Believe me, I was tempted. But no, I didn't cross that line," Oscar said, smiling as he recalled the encounter. "It was more like a JO session with your buddies, you know. You try to keep your eyes on the TV while watching your buddy beat his meat. Then when one of you is cumming, the other gives in and watches openly."

"I didn't have any friends like that at all," I replied. "I'm coming to realize what a sheltered life I led."

Oscar laughed. "You better make up for lost time!"

I smiled and thought to myself, "I think I'm doing just that this weekend."


When we made it to the shopping center, I had to adjust myself before getting out of the car. Otherwise my erection would've been completely obvious.

Oscar and I made our way through the heat and into the air-conditioned comfort of the store. Though I'd never been to this location and it was laid out differently than where I worked, the merchandise and fittings made it feel like deja vu.

I quickly oriented myself and guided Oscar to the kitchen area, where he picked out a couple gadgets, some bright kitchen towels, and a hefty, professional-grade cutting board. A cute retail queen politely took the items from us and held them for us at the checkout counter. We toured leisurely through the furniture section, occasionally stopping to test out a couch or admire the wood on a table or dresser.

"Dan would kill me if I buy any new furniture," Oscar said, pouting playfully. "But it's nice to dream."

We made our way to the bed and bath area and he carefully mulled over the features of various hampers. "I need one in my massage studio to hold all the dirty sheets and towels," he said.

When he reached for a stylish, modern wood version, I shared with him how many of them had been returned to my store. "They're very prone to splinters," I disclosed under my breath.

"I'm so relieved I have someone on the inside to steer me clear of catastrophic decisions," Oscar whispered and playfully squeezed my butt.

He chose a tasteful wicker version, which I gave my professional thumbs up.

After perusing the outdoor decor and selecting a couple of solar lanterns, we made our way to the checkout. As the retail associate, Caleb, pulled out the items he was holding for us, I retrieved my employee discount card from my wallet and handed it to him.

"Oh, I see we're family," he purred, taking it from me.

"In more ways than one," Oscar added without missing a beat.

Caleb laughed and winked at us. He rang up the items and told us the total before my discount and after. "Will you be paying for this or will your hubby be picking this one up," Caleb asked, his voice dripping with sugar.

Oscar snorted. "Daddy'll be picking up the tab," he said, and then slipped his hand up the front of my shirt to massage my chest.

"You're making me jealous," Caleb purred and took Oscar's credit card. I could feel myself blushing.

Oscar continued to massage my chest, which was causing my nipples to harden, as Caleb carefully wrapped the purchases and packed them into two large shopping bags. "You're all set," he said, hand us the bags. "You boys have a wonderful loooooong weekend."

"Thank you. You, too," I replied, taking one of the bags. Oscar pulled his hand from under my shirt and grabbed the other.

As we exited the store, Oscar squeezed my ass and looked back over his shoulder at Caleb. Once we got outside, he let out a laugh. "I'm sorry for the impromptu molestation, Robbie," he said. "I just couldn't resist playing along with him. I'm just going to pretend that he really thought we were a couple, and that he wasn't just trying to butter me up."

"It's all good," I laughed. "I don't think it's so absurd to think we could be a couple. You're a handsome guy. With a nice body, if you don't mind me saying."

"Oh I certainly don't mind you saying," Oscar said, squeezing my shoulder as we made our way through the heat to his car. "Flattery will get you everywhere."

We tossed the bags into the trunk and climbed into his car.

"Thank you so much for letting me take advantage of your discount," Oscar said as he cranked up the A/C. He pulled his t-shirt in and out to fan himself.

"You're welcome," I said. "I'm happy to share it with my hubby." I patted his knee playfully.

Oscar laughed. "Now I'd love to treat you to a massage this afternoon," he added. "Dan said your shoulders were in knots."

"That's so sweet," I replied. "But you really don't have to do that."

"I know I don't have to. But I want to," he squeezed my knee back. "It's my way of saying thanks."

"Okay. I'd like that," I said, giving in to his generosity. "I've never had a massage before."

"You've never had a massage?" Oscar said, clutching imaginary pearls at his neck. "What kind of homosexual are you?"

I laughed. "A poor one," I said.

"Well you are in for a treat then," Oscar said. "I'll give you the deluxe treatment. And I'll have you melting on the massage table -- and not because of the heat."

"That's exactly what Dan said," I laughed.

Oscar smiled at me. "Speaking of heat, I'm going to take this off. It's too hot in here." He pulled his t-shirt over his head and set it on the armrest next to him. "Ah, that's better. Now can I treat you to an icy drink for the ride home? There's a Starbuck's drive-thru around the corner."

"That sounds great," I said. As we pulled out of the parking lot, I unbuttoned my shirt and spread it open, letting the A/C wash over my sweat-dampened chest. My nipples perked up once again.

Next: Chapter 15


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