Everyone in this story is 18+.
The next week passed by without much issue. Oh, I was horny, sure. But between classes and homework, I didn’t have much time to act on it. Not to mention that I was caged. Now it was finally Saturday, which meant another shot at freedom. A new wager between Ryan and me, one that would decide my fate for the next seven days.
“What’s it gonna be?” Ryan asked. He sat at the edge of his bed with his feet dangling below.
“A rematch,” I stated confidently. “But this time, it's best out of seven. If I win, you give me the key - permanently. I won’t let you trick me again.”
Ryan chuckled from across the room. “Okay, okay. That’s fine by me. And if I win?”
I took a deep breath. “If you win… I stay locked for another week.”
My roommate scoffed at me. “That’s it?” He hefted himself off the bed, then began to walk towards the door. “Come find me when you have a real offer.”
“Wait!” I said, hopping off my own bed and chasing after him. “What’s wrong with that?”
Ryan turned to face me, wearing an incredulous look. “Where’s the reward for me?” he asked. “If you win, you’re free. If I win… nothing happens? I don’t see much of a point in that.”
He had a point. “Alright, fine,” I said. “How about this? If you win, I’ll suck your dick.”
My roommate paused to consider. He stroked his chin pensively, though I had a feeling he did it more to tease me than anything else. It was just like him to drag it out, to hold the weight of the decision over me. Unfortunately, he held all the power here. I was the one that was locked; he was the one with the key. After a week spent caged, I was willing to do almost anything to be free. I knew that, and I was almost certain that Ryan did too.
“Sorry, James. That’s not gonna cut it,” he finally said.
“Please,” I begged. “There’s gotta be something I can do.”
His eyes lit up at that. “Oh, there is,” he said with a grin. “But I don’t think you could handle it.”
“What is it?” I asked.
“No clothes for a week.”
My mouth opened wide. No clothes? That would be humiliating. He wanted me to spend a whole week naked, wearing nothing but this stupid cage? I shook my head. “I don’t know…” I said.
Ryan shrugged. “Suit yourself.” He took another step toward the door, then rested his hand on the knob. He began to twist it.
“Okay, fine!” I said. “Not like it matters. I’m gonna win anyway.”
He smirked. “Deal?”
“Deal.”
We shook on it, then we settled in for the most important match of my life.
Since I proposed the bet, I got to choose the game. I went with one of those old-school fighting games; the kind with a simple moveset that consisted of basic attacks, specials, blocking, and dodging. I figured that the newer games had too much technique, and something like this would level the playing field.
Boy, was I wrong.
I lost the first match in a landslide. The cage suddenly felt a lot tighter as I watched my chance at freedom slip away. It became harder to focus. I couldn’t keep my mind fully on the match with my dick swelling up, reminding me just how hard this past week had been. I needed a win here.
The second match was a bit closer, but I still lost. “We should just call it here,” Ryan taunted.
“Shut up,” I joked. “We’re playing best out of seven. I’ve got time.” I was feeling him out, learning his moves and how to avoid them. Unfortunately, the same went for him. With a longer series like this, adaptability was everything.
I walked away with round three by a hair.
“Ha!” I shouted. “Looks like I’ll be getting that key after all.” My palms were sweaty. I was nervous. But I couldn’t let that show. There was too much on the line.
Maybe I had gotten lucky. Or maybe Ryan was going easy on me, letting me get my hopes up before sweeping the legs out from under me. Because after that third round, he proceeded to crush me. The final score was 4-1, a crushing defeat for me. My face flushed as I knew what was coming next.
My roommate put the controller down. When he looked over at me, his face said it all. “Well?”
My dick throbbed, pressing up against the inside of the cage. Another loss. Another week locked. Except this time, I’d be naked. “Do I have to?” I asked.
He nodded. “A deal’s a deal. Hand them over.” He held out his hand, waiting for me to strip.
“Okay…” I said nervously. Gosh, this was embarrassing. I began with my shirt, pulling it up over my head and placing it in his open hand. Then I dropped my shorts to the floor. I stepped out of them, then bent over and grabbed them off the ground. I tossed them to my roommate, making eye contact with him wearing just my underwear.
“Go on,” he said encouragingly.
I swallowed, trying to calm my nerves. I couldn’t do it while looking at him. Instead, I glanced toward the ground, then slipped my underwear off.
“Fuuuck,” he whispered.
I was completely naked. My dick swelled to fill every inch of the cage, threatening to break it wide open from how hard I was. But the cage held firm, just like it always did, preventing me from getting a true erection. Even that was beyond my control now.
I stooped over to pick up the underwear. I walked over and handed them to Ryan, making good on our latest bet.
There was a dangerous look in his eyes, along with a smile to match. “From now until next Saturday, you’re not allowed to wear clothes as long as you’re in this room. Got it, James?”
“Got it,” I said quietly.
“Good.” He threw my things into the corner of the room, then plopped down into the chair at his desk. “Now take a seat on the floor here. You’re gonna watch me jack off,” he stated.
I watched on in shock as his fingers began to fumble with the button and zipper on his shorts. “Wait!” I said. “This wasn’t part of the bet!”
“You’re right. But unless you want to go another week without cumming, I’d suggest you do what I say. How long has it been since your last orgasm?”
My cheeks went bright pink. “Six days,” I muttered.
Ryan shifted his weight on the chair, slipping his shorts down to his ankles. His bulge looked bigger than ever in his tight boxer-briefs. “Uh huh,” he said. “And do you think disobeying me is gonna do you any favors?”
I shook my head.
“Then get over here before I change my mind about giving you a release this week.”
His tone was so demanding. So controlling. So… hot? I dropped to my knees without thinking, then crawled over to the spot in front of him.
“That’s it, James. Get familiar with being down there.”
“Yes, Ryan,” I mumbled. If not for my unfortunate imprisonment, I would’ve been rock-hard now.
My roommate pulled down his underwear, letting out his massive cock. Just seeing it was enough to drive me crazy. He grabbed it in one hand, then lazily began to stroke it. “Mmmm. This feels sooo good, dude. I bet you wish you could be jerking off right now.”
“You have no idea.”
Ryan smirked. He placed his foot on my caged dick, a physical reminder of his power over me. He continued to jerk himself off, pumping his dick lazily with long, steady strokes. “Too bad you’ll just have to watch for now,” he teased. “Don’t worry, though. I’ll give you plenty of chances to earn an orgasm this week.”
