[Patreon Exclusive] Roommate Dares: Chapter 5 (Patreon)

No matter how hard I tried, I couldn’t put an end to the moment, and the longer I waited, the more hopeless an end seemed. He slipped my cock into his mouth and he began to suck. My fingers nestled into his soft hair and I watched as his head bobbed gently up and down, my cock hardening fast, pressing against his plump lips.

“Just like that,” I said, letting out a soft sigh. It felt so nice. He knew just the right moves to make it feel amazing, running his tongue along the base of my shaft, tickling the tip of my cock gently. “Don’t stop,” I said. My body started to relax, deflating into the soft couch. I had enough muscle control left to reach for the little remote in my pocket and turn his butt plug to the highest setting. According to the box, the vibrating butt plug was supposed to be strong enough to bring a man to orgasm via prostate stimulation. I didn’t believe it when I read it, but I was believing it now as I watched Jake squirm and moan, muffled by my big erection.

My cock began to tingle and bulge. I was close to finishing, but I didn’t want to finish in his mouth. I wanted more. “Get up,” I said. He stood up. “Bend over,” I said, and he did. Without standing up, I flipped the skirt of his dress onto his back and I slipped down his panties. He didn’t bother to resist. His erect cock sprung free. His legs were trembling, he was probably close to finishing himself. I grabbed the base of the butt plug and I pulled it out, revealing his gaping asshole. “Sit down,” I said, patting my lap.

As he sat down, I lined my cock up with his gaping butthole. He took it without resistance, sliding it deep into his body. “Oh fuck, that feels good,” he said, his legs trembling even more. I was amazed he was able to stay up in those heels while his legs trembled.

I grabbed his hips firmly and then I started to thrust up, into his body. After just a few penetrations, he was moaning. “Oh God, don’t stop! Don’t stop!” he said. His breaths were becoming heavier and more shallow. “I’m going to come,” he said.

I don’t know why I did it, what came over me, but I reached around and grabbed his erect member firmly in my hand, and I started to beat him off. I wanted to feel him coming. I wanted to feel his cock bloating as it blasted shot after shot of hot cum in our living room. “Oh fuck!” he cried, and then he came. I slipped my hand up, cupping the tip of his cock as he came, getting his whole load into the palm of my hand, and then I spread it up and down his dick and balls.

I didn’t even have to thrust up anymore. He had taken over, bouncing up and down, slapping his ass against my lap repeatedly. I was about to come. I tried to hold back, biting my tongue, groaning loudly. But it was hopeless. His asshole felt too good, puckering tightly along my hard shaft. I came, deep in his butt. He sat down hard, one last time, as he felt himself filling up.

And then we found ourselves in a familiar situation, silent as we caught our breath, wrapping our heads around what we’d just done. Once again, I’d fucked my male roommate. Was I actually gay? Was he actually gay?

I had Jake spend the rest of the day cleaning out the garage. I didn’t stick around to watch. Instead, I sat in my room, wondering what the hell was going on. Why were Jake and I suddenly so sexual with one another? Were we really gay?

It didn’t seem fair to call us gay. I wasn’t attracted to Jake when he was just himself, in his regular clothes, using his regular voice, without any makeup on, and as far as I could tell, he wasn’t attracted to me when I was just my regular self—or was he? It was him that initiated the sex, while he was giving me a foot rub. And I let him fuck me in the ass when I was the one wearing the little French maid outfit.

It was strange, as if getting into the feminine character was actually changing our personalities.

After that day, neither of us ever talked about what happened. We went on with life as usual, as if we’d never had sex before. Though I never could look at him the same, without thinking about his big cock ramming me in the ass, and I’m sure he couldn’t look at me quite the same way either. We spoke much less, especially once Jake started seeing a therapist about his gambling addiction.

His therapist seemed to really help him. After just a month, he was back on his feet financially. He didn’t take every paycheque he made down to the bar to bet with strangers. When we went to play basketball, he didn’t put wagers on any shots.

While it was good that he’d gotten his gambling problem under control, I felt bad for him. He never seemed quite the same without his wagers. He didn’t get nearly as much joy out of his regular day-to-day activities. Nothing seemed to spark that fire in him anymore. I came home one day and he was watching hockey, hardly paying any attention, not even flinching when goals were being scored. It wasn’t the Jake I was used to—the Jake who would be on the edge of his seat, screaming with joy whenever his team scored.

I sat down to watch the game with him, the Calgary Flames against the Edmonton Oilers. It was tied 2-2. As I sat to watch, the Oilers’ goalie got checked and sent off the ice. Without their main goalie, they were doomed. I looked over at Jake, who didn’t even seem to be phased by the development. “Good game?” I asked.

“It’s alright,” he said.

I missed that joy that used to sparkle in his eyes. I missed the old Jake, my old roommate. I didn’t like the new tranquilized Jake, who didn’t have any zest for life. I wanted the old Jake back, the one who would make a quiet room the most exciting place on the planet, the one who would get my heart rate up with a simple wager, the one who would bend me over and fuck me in the ass—“Want to make a bet?” I said.

He looked over at me, wide-eyed. “I can’t,” he said, but I could tell he really wanted to.

“Just a friendly bet—no money or anything.”

He bit the corner of his lip, trying his best not to crack a smile. “I don’t know…”

“I bet the Oilers take this game,” I said, ignoring his reservations.

“What are you betting?”

“If the Oilers win, you have to be my slave for the day tomorrow. If you win, I’ll be yours.”

He couldn’t stop the smile from overtaking his face. “You’re on,” he said.

I knew damn well that without their goalie, the Oilers were doomed. Within the next five minutes, the score went up to 5-2, for the Flames. It was looking like I was going to be Jake’s slave for the day. I smiled—it was exactly what I wanted. And with that one, simple bet, Jake was once again full of life, on the edge of his seat, a smile on his face, excitement burning in his eyes.

THE END