My Roommate Caged My Dick - Ch. 18

Everyone in this story is 18+.

I reluctantly sat back on the couch, making sure to put a T-shirt under me. I just rode my boyfriend like a bull for all of five minutes, but now it was time to resume our game.

The rules were simple: a quick 1v1, where if I won, Ryan would fuck me for five minutes straight. If I lost, Ryan would still fuck me for five minutes straight, but he’d also get to write something on my body. Anything he wanted, anywhere he wanted. Then we’d do it all again until he inevitably blew his load inside me. Crazy, I know.

The two of us selected our characters and settled in for round two. I was feeling good coming off a win, but Ryan’s greatest skill was adaptability. Any edge I had over him was fleeting, and the longer this went on, the more it swung in his favor.

We were on the edge of our seats. I never thought I’d be gaming naked next to my roommate, but here we were. My palms were sweating. My eyes burning from going so long without blinking. But in the end, I couldn’t keep up.

“Ha!” Ryan exclaimed. He stood from the couch, causing his boner to bounce wildly. “Got you this time.”

I sighed in defeat and placed my controller at my side. “Okay,” I said, “what’s it gonna be this time?”

There was a devious look on his face. “Follow me.” He scooped up his permanent marker, then walked over to my bed. “Stand here,” he said.

I followed along, standing at my bedside. “Like this?” I asked. Then I felt a shove from behind. “Whoah!” I found myself face-down on the bed, my chest touching the mattress with my feet still planted firmly on the ground. I was bent over, ass exposed and easily accessible for my boyfriend.

“Like this,” he replied. “Now brace yourself, James.”

“What are you gonna- ohhh fuck.” I heard it before I felt it: Ryan spitting directly onto my hole. “That’s so hot,” I whispered. I reached back and pulled my asscheeks apart, preparing for him to enter.

“Mmmm,” Ryan hummed. He pushed his cock against my wet hole, teasing the entrance. After riding him earlier, there was very little resistance for him. Yet he kept me on edge, pushing gently but not quite entering.

“Fuck, babe. Just put it in already.” My dick was struggling to grow hard, attempting the impossible. Every time his tip pushed against my hole, it caused another throb in my cage.

“If you say so.” My boyfriend pushed his hips forward and his dick slipped right in. Between the spit and the leftover lube, I had no problem taking Ryan’s cock. That is, until he bottomed out inside me. WIth the way I was holding my cheeks apart for him, he went DEEP. “How’s that?” he asked.

“So- mmf- good,” I managed to force out. I was struggling to get accustomed to this new position, taking quick and shallow breaths. And it did feel good - incredible, even - but I simply wasn’t used to feeling something so big go so far inside me.

Behind me, I heard Ryan uncap the marker he’d chosen. “Now let’s see,” he mumbled to himself. “Where to put it…”

Suddenly I remembered the price for losing. My face flushed pink, the warmth of the humiliation burning on my cheeks. Then I felt the tip of the marker pressing against my right asscheek. He wrote in short, quick strokes, but whatever it was was either fairly large or very wordy. By the time he was done, it felt like half of my asscheek was covered in writing.

“There,” Ryan said. He capped the marker, then tossed it onto the mattress nearby.

“What does it say?” I asked.

“You’ll find out soon enough.” His cock was still buried inside me, though by now I’d managed to relax a little bit. “Here, hold this. It’s about time I pound your ass.”

He thrust his phone into my face. On it, there was another timer set for five minutes, already ticking. I reached forward to grab it, at the same time feeling Ryan grab me by the hips. And then it was on.

“Oh fuck!” I yelped. With his firm grip on me, Ryan pulled back and bucked his hips forward, sending his cock deep inside me once more. Then he did it again, and again, going from zero to one hundred in a matter of seconds. It was all I could do to keep up.

“Oh, come on, James. Don’t act like you don’t love it,” he taunted. His dick punched into me, each thrust jerking my entire body. I was sprawled out on the mattress, my face stuffed into the blankets. I’d already abandoned his phone, my hands searching out anything to hold onto. I gripped the blanket, holding tight as my boyfriend used my hole for his pleasure.

“Hnnnn,” I moaned desperately. “Fuck- oh fuck- hnnnn- ah, fuck!”

“Fuuuck. Let me hear you whimper like you’re my bitch, James.”

“Yes- ah!- Yes, Ryan!” I forced out. I was lost in all the sensations I was feeling, the mixture falling somewhere between intense pleasure and overwhelming stimulation. I buried my face deeper into the covers, stifling my moans. I yelped and hollered and whimpered for my boyfriend, holding onto the bedspread for dear life as he claimed what was his.

RING.

Before I knew it, the timer had gone off. I lifted my head momentarily. “Time’s- mmm!- time’s up,” I muttered. I reached for the phone, flailing my arms a bit before I could find the source of the alarm. My hand finally landed on Ryan’s phone and I quickly disabled the noise.

Standing behind me, my boyfriend continued to plow my ass.

“R- Ryan,” I said between thrusts. My body lurched forward again and again, with his relentless fucking pounding me into the bed. “The- timer!”

“Not now,” he spat. “I’m close.” He carried on fucking me, completely abandoning our deal.

His balls swung into me from below. My caged dick flailed back and forth. My legs had long-since given out, my body collapsed on the bed with my feet hanging underneath. Only Ryan’s thrust kept me pinned to the bed, preventing me from falling down.

“Almost. There.” he grunted.

“Cum in me,” I begged. The words left my lips by instinct alone. It was what I wanted. What I deserved. To be used, to serve a real cock while mine remained locked away. Almost halfway through Locktober, things were finally starting to click.

At the last second, Ryan pulled out. He finished the job with his hand, jerking his massive cock across the finish line. My hole gaped from the sudden emptiness, opening and clenching as hot ropes hit my bare skin. I felt his cum spraying me, landing all over my asscheek and directly onto the writing. Some dribbled between my cheeks, coating my twitching hole. Then without a word, he wiped it with his cock and pushed it inside. He ran his dick in and out of me a few more times, then finally pulled out for good.

“Fuck,” he sighed. “That was amazing.”

I propped myself up on my elbow, turning over my shoulder to face him while remaining sprawled out on the bed. “Holy fuck, Ryan. You have no idea how hot that was for me.” I was in disbelief, riding high even though I didn’t get to cum myself.

He grinned. “Oh, I think I know. With the way you were moaning, I think the whole dorm knows at this point.”

My jaw dropped, but I couldn’t help smiling back at him. “So do I get to know what you wrote?” I asked.

“Hand me my phone.”

I tossed it over, then my boyfriend stepped back and took a picture of my used ass. “Here,” he said, tossing it back.

The phone landed next to me on the bed. I picked it up, feeling even hornier as my eyes took in the image. ‘PROPERTY OF RYAN,’ was written in all caps across my right cheek, with an arrow pointing towards my hole. I could read it clear as day, even with the streaks of cum covering most of my ass.

“Fuuuck,” I whispered.

“I hope you like it,” my boyfriend said. “Because we’re going to be doing that a lot more from now on.”