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My bet with a roommate... I lost [F]

Mar 19, 2024

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cheng cuiping

There is something compelling about angry sex. To legitimately be angry with someone and to take it out in the form of sex is an intoxicating feeling.

During my time in the city, I lived with a lot of people. We lived in a large place with 8-10 roommates at a time. With that many people it is inevitable that you'll step on some toes now and then. I had a particular problem with the guy that shared a wall with me. He would bring different people home all the time and he definitely had some interesting kinks. I didn't mind either of those things. What I did mind was that every time I had to be up really early it seemed that it would be the night that I was kept up until 5 in the morning with the screaming and loud bangs from his room. I tried talking about it, but he would write me off as being jealous. That made me incredibly frustrated. So, we would get into some pretty epic yelling matches.

One night, I had a meeting I had to be at 8 am. It was a really important meeting to me, and I wanted to look my best and be on the top of my game. I had not even bothered to say anything to Jake, my next door roommate, because I knew it was more likely that he would try harder to find someone to torment me with that night.

It ended up not mattering. Around 1:30 a.m. I woke from a dead sleep to hear that Jake had indeed brought someone. The banging and moans started up, but for some reason they stopped suddenly, and I heard arguing voices. Suddenly, I heard the door to Jake's room slam, and someone stormed down the hallway towards the front door. A few moments later the front door also slams, and I hear the catcalls and jeers coming from some of our other roommates. I had two choices then; I could ignore the whole thing and go to bed, that way I could get some sleep and do my best tomorrow. OR I could go over to Jake's room and see if everything was okay… The second option did not seem like something I wanted to do at all but for whatever reason, I felt like I had to go check in on him.

I knocked lightly at his door before pushing it open. It had been slightly ajar which makes me think that he went after whoever it was that rushed out of here a moment ago.

"Hey," I said, taking a step into his room. He was sitting back against his pillows, looking up at the ceiling.

"Everything alright?"

He sighed, "Yeah she was just being mean," he told me as his eyes tracked to me. "Are you lost?

I frowned at him and shook my head. "I came in to check on you."

He looked legitimately surprised. "Wow, that's surprising."

I turned and went to leave but he chased after me, "Wait, that is so nice of you. Come sit with me a minute."

We sat down, side by side on his bed, our conversation felt stunted, like we were not sure what to say to each other. After a few minutes, I said my good nights and I started to stand.

"Wait," he said catching my wrist, "unless you'd like to take that other girl's place for the night…"

I laughed, "I don't think you're exactly my cup of tea."

"I bet I am, in fact I bet you would really enjoy it," he told me.

"I bet I wouldn't even get off,"

"I will take that bet," he told me, shaking my hand.

"What do you get if I win."

I was stunned silent for a moment. He wanted to make a bet that he could get me off?! I did not immediately shoot down the offer, which surprised even me. It had been a bit of a dry spell and he was smoking hot. At the very least I would have a good time and it may even help with my meeting in the morning. And I could possibly get something I wanted in return…

"Deal." I shook his hand. If I win, you cannot bring girls into your room for a month. You have to go somewhere else to be loud."

He shook his head before answering, "Fine. But if I win, I get to fuck you whenever I want, wherever I want, however I want, for a week. And I get to pick the week at a later date to cash in."

"I don't think that's quite fair...," I started.

"A month is much longer than a week, Maddy. Plus, my win will be fun for both of us. Your win will only be for you," he said with a wicked smile.

"Deal."

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I went to shake his hand again but instead he grabbed it and flipped me around, pulling my back against his front. I could feel the stiffness in his pants against my butt as he ground into me. He pushed my hair aside and put his mouth to my neck. "I'm going to make you scream," he whispered. I felt my pussy grow damp. He used his hold on me as leverage to force me onto my knees on the bed. He ran his hands over the thin fabric of my pajama pants that covered my ass. He stroked me a few times this way before slapping my ass… hard. I cried out but before the sound even finished leaving my lips, my pants were on the floor. "Maddy, you don't wear underwear?" he questioned, taking his fingers to trace the opening of my pussy.

"Not to sleep," I told him.

"That might have been a mistake," he said before grabbing me by the hips and flipping me onto my back. He was rough. He pinned my arms above my head and leaned in like he was going to kiss me. I moved to accept the kiss but instead he plunged his fingers into me and thrust them over and over in and out. I bit down on my lip to keep from crying out.

"Come on Maddy, I know you're feeling good… you don't have to be quiet…" He flipped me onto my belly and continued his finger assault on my small pussy. I groaned into the pillows.

Jake readjusted so his arm wrapped around my front where his hand found my clit. He started working me there, fast and hard. I moaned and he reached up and took a handful of my hair. He tightened his fingers into a fist, pulling my head back with my hair. "I told you I want you to scream for me."

I whimpered, it hurt that he had a hold of my hair, but I also felt a rush of wet between my legs as his rough voice told me what he wanted me to do.

He used my hair to force me up on my knees in front of him and pushed me up against the wall. My boobs were smashed into the cold of the wall as his mouth worked up and down my neck, his hand never relinquishing the grip in my hair.

After a minute he pulled my head back again hard, the pain making me cry out. He pushed me onto my back, his hands going to my shirt. He pulled it off in a fluid motion and pulled the fabric of my bra down to my belly, exposing my nipples and breasts. He took one fully in his mouth, sucking and scraping the nipple with his teeth. It was simultaneously pleasure and pain. With his other hand, he plugged two fingers inside of me again. I cried out as I came onto his hand, my juices soaking into his hand.

"Oh Maddy…. We're going to have so much fun… for a whole week."

I started to say something, but he shook his head. He pulled my legs to either side of him and positioned himself at the entrance of my pussy. He slid in in one fluid motion, filling me, and my mind went blank. I wrapped my legs around his waist, urging him to go deeper and harder. He wrapped his arms around my back and lifted me up. Holding me up in the air he thrust into me over and over. He slammed me into the wall, my back hitting against it as he continued to drill his dick into me. Over and over, he continued for what seemed like hours. Every time I started to go over the edge with an orgasm, he would slam us up against the wall, the pleasure mixing with the pain.

As I neared the edge of yet another orgasm, my pussy clamping down on his hardness, I felt him swell inside of me, the added size sending me over the edge as he finished with me. My back slammed into the wall with each of his final thrusts, I felt dizzy with the pleasure of it all.

As he pulled out of me, I slowly slid down the wall, my head spinning.

"So, I guess I will just let you know when that week starts then?" he told me with a wicked grin, I nodded, still dazed by the entire thing. As my senses began to return to me slowly… I realized that a week wouldn't be such a difficult thing to lose in the bet… I would be really sore though if tonight was any indication.

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