My Roommate Caged My Dick
Copyright© 2025 by SlumberingToad
Chapter 4
BDSM Sex Story: Chapter 4 - A friendly bet between roommates ends with a caged dick.
Caution: This BDSM Sex Story contains strong sexual content, including Ma/Ma Consensual Gay Fiction School DomSub MaleDom Humiliation Anal Sex First Oral Sex
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.