The Roommate Problem

By Kevin Sting

Published on Apr 25, 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.


After getting our iced lattes from the Starbuck's drive thru, Oscar drove us back to the house. On the way, our phones simultaneously buzzed with an incoming message. It was from Alex. He and Dan were going to be longer than expected and wouldn't be back until around 3:00. He wanted to know if we were okay having lunch on our own, as they planned to grab something while they were out.

"I've got some stuff at home that I can throw together a salad for us, if you're okay with that?" Oscar asked.

"That sounds great," I replied. And then I texted a message back to Alex: "I guess we'll survive without you two."

Once back at the house, we unwrapped Oscar's purchases and then he busied himself prepping the salad for us. I contributed to the effort by slicing radishes, cucumbers and cherry tomatoes, as he whipped up a dressing I'd never had before -- green goddess.

Oscar poured us each a glass of rose, and we sat at the dining table across from each. He hadn't bothered putting his shirt on, nor had I bothered buttoning mine back up. The cool A/C in the house had our nipples hard.

Like his dinner last night, the salad was delicious. As we ate, we shared more stories about ourselves and about Alex and Dan. He told me how he and Dan had once been caught having sex on the beach in Hawaii and I shared my recent adventures with my landlord.

"Oh my," Oscar said. "Sounds like the perfect landlord to me. I hope you plan to take him up on those midnight swims."

"I'm sure I will -- we will," I laughed. "I doubt Alex will let that opportunity pass by."

After tucking our lunch dishes away in the dishwasher, Oscar stepped behind me and placed his hands on my shoulders. "Since the boys won't be back for a couple hours, how about we get you out on the massage table," he said, rubbing my shoulders lightly through my shirt.

"I can't say no to that," I smiled.

"No, you can't!" he laughed. "Let's take this shirt off and see what I'm up against." He slipped my shirt off my shoulders and I let it slide down my arms and off. He squeezed and kneaded up my shoulders to my neck. "Oh wow, you ARE really tight."

"Guilty as charged," I said.

"Okay, let me get the A/C going out in the cabana and I'll get the table prepped for you," he said. "Why don't you hop in the shower and rinse off and then head on out."

"Okay, sounds good," I said.

He headed out into the backyard as I made my way into the bedroom. I slipped off my shorts and shoes and went into the bathroom and turned the shower on. Stepping inside, I let the cool water rinse away the sweat from our morning outing. I dried myself off and headed back into the bedroom.

Through the sliding glass door, I could see out to the cabana where Oscar was draping a white sheet over his massage table. And then he unrolled the blinds across each of the windows.

I was certain I wouldn't need clothes for the massage, but it felt strange walking outside to the cabana buck naked. So I opted to wrap a towel around my waist. I slipped on my flip-flops and headed out through the sliding glass door for the short walk through the heat to the cabana.

I rapped lightly on the French doors before opening them. The interior of the cabana was pleasantly dimmed by the blinds and the A/C had cooled it to a comfortable temperature.

"Welcome to my office!" Oscar said, gesturing around the room. There was soothing, new-agey music playing at a low volume, a small Zen fountain bubbling on a table in the corner, and an aromatherapy atomizer spraying a moist, vaguely citrusy mist into the air. "I know it's a little cliche, but that's what everyone expects when they come for a massage."

"It's lovely," I said honestly. "Really relaxing vibe. And it feels like a different world from the heat outside."

"Perfect," he said, rubbing his hands together. "Let's get you settled on the table face down. Since we're family, I won't bother stepping outside. I'll take that towel from you. And just place your face into the little ring."

I pulled the towel off, handed it to Oscar, and he promptly tossed it in the new hamper we'd just purchased. I climbed onto the table, laid on my stomach, and settled my face into the padded ring -- which reminded me of a mini padded toilet seat -- at the far end of the massage table. I adjusted my penis downwards and then relaxed into the soft sheets. They were slightly warm, but not uncomfortable.

"Now I'd normally drape a sheet over you at this point. But again, since we're family, are you okay if I leave you undraped?" Oscar asked.

"Uh, sure, no problem," I said. He'd already seen me naked already.

"And is it okay if I take my shorts off, too, Robbie?" Oscar asked, quietly.

"Of course. However you're most comfortable," I replied.

I heard the sound of Oscar's zipper going down and then I could his shorts drop to the floor through my limited vantage point in the ring. I felt his hands settle gently on my back.

"Now Robbie, I want you to take a deep breath for me," he said, in a deep almost whisper. "Inhale through the nose, exhale through the mouth."

I did as instructed. As my eyes fluttered open, I could see his tanned feet through the face ring.

"Once again. In through the nose, letting the breath fill your chest, your stomach, your pelvis and down through your legs to your feet," he said and paused. "And now exhale through the mouth, letting all that air back out through your body."

We repeated with three more deep breaths, all the while his hands just rested on my back. Then he lifted his hands, and his feet disappeared from my view. Oscar stepped away and I could hear the sound of a pump bottle followed by the moist sound of his hands being rubbed together with lotion.

Oscar placed his slicked up hands on my back once again and began to rub gently up and down on either side of my spine. He rubbed back and forth from my neck all the way to the cleft of my butt cheeks.

"Robbie, just relax and breath and enjoy," Oscar said quietly. "Let me know if I the pressure is too much or if you have any discomfort."

"Okay," I mumbled through my padded ring.

For the next 40 minutes or so, Oscar kneaded the knots in my shoulders and massaged me from head to toe along my back side. Every once in a while he'd pause to check in. "That pressure feel okay?"

I could barely managed to mumble out an "Mmm hmm." Sometimes the pressure was a little intense, but I quickly recognized that a few seconds of mild discomfort ultimately made the tension in my body disappear.

"You have such beautiful skin," Oscar purred at one point as he rubbed my lower back.

He kneaded my butt cheeks, pushing them together and pulling them apart like Alex and I had done to each other this morning. I could feel my asshole briefly exposed to the air as my cheeks were tugged apart. My cock tingled slightly at the sensation.

Then Oscar's hands slid down and worked on the backs of my thighs, just below my butt. He reached his hands down between my legs and pulled back away on my right thigh and then walked to the other side of the table and repeated the motions on my left thigh. As he plunged between my thighs, his finger tips would occasionally brush the tip of my cock, which I'd tucked down there at the beginning of the massage. I could feel my cock stiffening more from the accidental attention it was receiving.

Oscar lifted each foot, carefully massaging the sole and tugging on each toe. And then he lifted each leg and jiggled it from side to side. The maneuver caused my growing cock to rub against the sheet, which made it grow more.

He gently stroked back up my legs, over my ass, up my back and shoulders. He stood at the head of the table, his hands lightly touching my shoulders.

"Okay Robbie, time to turn over," Oscar said softly.

I pushed my chest up off the table with my hands and pivoted my hips sideways. This freed my erection, which snapped back up towards my stomach.

"Now if you can just scoot a little further down the table, I'll remove this headrest," he said.

I slid sideways down the table until my head was about even with the end of it. I laid back awkwardly realizing that my erection was on full display.

"Looks like somebody is enjoying the massage so far," Oscar said, smiling.

"Sorry," I said.

"Don't be sorry," he laughed. "It happens all the time. I'll take it as a compliment."

I settled back on the table and opened my eyes. Oscar's tan, furry torso hovered over me. My cock twitched and I felt a dribbled of precum land on my stomach.

He walked to a corner of the room and I could make out his chubby, uncut cock nestled in a thicket of dark pubic hair. When he returned to the table, he placed a warm, damp washcloth over my eyes. I heard the sound of the pump again and then his hands rubbing together. He placed his hands on my chest and began his tour of my front side.

Oscar rubbed back and forth over my pecs until my nipples stood erect. He rubbed circular motions around my stomach, the sides of his hands occasionally brushing the head of my cock. He worked down my hips, my thighs and calves, and then tended to my feet once again.

He lifted one of my feet and settled it against his furry stomach. He massaged the top of my foot and then up my ankle to the calf. Then he bent my leg at the knee and pushed my leg back up towards my chest. This motion exposed my asshole once again and pushed my erection into my stomach. After he replaced the first leg on the table, he repeated the steps on my other leg.

"Everything feeling okay?" he asked.

"Yes," I exhaled.

I could hear Oscar rolling a stool over and then he took my left arm and lifted it off the table. He settled onto the stool and pulled my arm out until it rested in his lap. I could feel the warm furriness of his pubes against the back of my hand. He massaged my hand, kneading each joint and knuckle and pulling on each finger. He laced his fingers between mine and dug his thumbs into the palm of my hand. After finishing with my left arm, he settled it back onto the table. Then he rolled around to the other side of the table and repeated the steps on my right arm.

When he was done with my arms, Oscar pushed the stool aside and returned to his position at the head of the table. He pulled the washcloth from my eyes and began gently running his fingers over the contours of my face. He kneaded my earlobes and dug his fingertips into my scalp. It felt amazing.

Oscar reached over me and grabbed one hand and then the other. In doing so, his furry stomach brushed against my face. He pulled my arms up over my head and stretched me out. After returning my arms to my sides, I could hear him pump out some more lotion. And then he began massaging my chest once again.

His fingertips brushed over my nipples. After a few rotations around them, he gave each one a gently tug between his thumbs and forefingers. I inhaled and then exhaled deeply.

Oscar then ran his hands down the sides of my torso, brushing my rib cage and down to my hips. He stroked up and down several times, each time working in toward the center of my torso until his fingertips rested at the top of my pubic hair.

He pushed his hands down through my bush and cupped my balls and then pulled them back up to my lower stomach. Narrowing in, he turned his hands so that his palms were resting on either side of my erect shaft. He pressed in gently, allowing his fingertips to touch my penis. My cock continued to leak precum onto my stomach as he held his hands in place against it.

"At this point Robbie, some of my clients like it if I take care of them," Oscar said in a hushed tone. "But I can stop if you'd prefer."

I opened my eyes and looked up at Oscar. He was smiling down at me. I tilted my head slightly and could see that his own cock was erect, as well. His dark foreskin was taught and had pulled back just slightly to reveal the tip of his pink cock head. "Yeah, Dan mentioned that," I said, smiling back up at him. "You don't have to stop."

Oscar smiled down at me as he pressed his fingers in against my shaft. "Excellent," he said. He grabbed my cock with one hand and rubbed the palm of his other hand over the head. "You've been leaking up a storm."

Oscar shifted his position from the head of the table to the side. It gave me a great view of his own erection. He began pumping my cock up and down, rotating his hand with each pump.

"You have such a beautiful cock, Robbie," Oscar said, stroking me. "Dan couldn't stop talking about it this morning while we were showering."

"Thanks," I blushed. "His is really nice, too. As is that piece of meat you've got down there." I looked down at his erection.

"This old thing," he laughed and wiggled his hips so his fat cock waved back and forth. I kept staring at it. "You're welcome to touch it, if you like."

"Really," I asked.

Oscar smiled and nodded.

I reached forward to grab his cock. I rubbed my thumb against the edge of his foreskin. "I've never actually played with an uncut cock before," I said.

"I'm honored to be your first," Oscar laughed. "If you squeeze tighter and pull back, the foreskin will retract. You can push it back and forth over the head."

I gingerly did as he instructed and was mesmerized by the pink head emerging from the hood. When I stroked the other direction it disappeared again. I repeated the motion, pushing and pulling the skin back and forth over his head.

"That feels wonderful," Oscar cooed.

As I stroked his cock, he pumped up and down on mine. He reached over and pinched one of my nipples and I stroked his ball sack with my free hand.

We continued jerking each other off silently for several minutes.

"I'm getting really close, Robbie," Oscar said breathlessly.

"Can you shoot it on my cock?" I asked, surprised at my boldness.

Oscar's eyebrows raised devilishly. "I'd be happy to oblige. Why don't you let me take over from here so I can aim properly." I released his cock and he took it in hand and began pumping himself. I stroked my own cock in unison.

He was damp with sweat and he closed his eyes occasionally to focus on his cock. His pumping became more feverish and I could tell he was getting close. "I'm gonna cum," he gasped. He aimed his cock at mine and pumped faster and tighter.

"Oh yeah, Oscar, shoot that load," I said, encouraging him.

He gasped again and then exhaled with such force that he spit on me a little. His cock began to spew forth his white hot seed. He pressed the head of his cock against mine so that the cum spilled down over my glans and down the shaft. After several shots emerged, his orgasm subsided. He opened his eyes and looked down at my cum covered cock hungrily.

"Let me take care of that for you now," he said, grabbing my erection. He used his semen as lube on my cock and pumped up and down on the shaft. The sensation was amazing. My butt clenched as I could feel my own orgasm rising.

I raised my hands and tucked them back behind my head. Oscar used his free hand to massage my chest, lightly pinching one nipple and then the other. He rubbed his hand through my sweat-dampened pits and then back again across my chest.

My toes began to curl involuntarily. "Here it comes," I said.

Oscar pinched hard on my nipple as he pumped my cock. The first shot of cum launched from my cock and landed on my chest. The remaining volleys covered my stomach and Oscar's hand in spunk.

"Beautiful, just beautiful," Oscar said, fondling the cum on my cock. He raised a cum-covered finger to his mouth and tasted it. "And delicious, too." He dutifully placed each finger in his mouth to lick off the cum. "There's nothing quite like young cum."

I laughed and looked down at the mess I'd made.

After he'd cleaned off his hand, Oscar began scooping the cum off my stomach and licking his fingers clean again. He looked down at my softening cock, still dripping with cum. "Do you mind if I clean that up for you?" he asked, smiling at me.

"Be my guest," I said, smiling.

Oscar lowered his head and took my cock in his mouth. He sucked and licked until no cum remained. Pulling back on the shaft, he licked the piss slit to get the last remaining droplet, and then he gave me a gentle kiss on the cock head.

"Thank you!" Oscar said, enthusiastically.

"Thank YOU!" I replied. "The massage was amazing. And so was that."

"They don't call it a happy ending for nothing," Oscar laughed.

Next: Chapter 16


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