Roomies

I just stood there for thirty seconds or so, my back pressed against the dirty wall, my pants around my ankles and my dick hanging out in the open. The initial shock of the situation started to wear off and I pulled my shorts back up and left. I skipped my class and went to the cafeteria. I spent the time I was supposed to be in all my other classes that day sitting at a table, looking at my lunch.

The humiliation I felt was consuming me. I mean, my sister had just jacked me off into her panties. Somehow she knew that I had cum on her ass the other night and now she was tormenting me by treating me like a depraved pervert... and I was. I was a sick pervert who cums for his sister.

After a few hours of sulking and feeling sad for myself, my feelings slowly turned to anger. After I thought about it for a while, I started to think that this was all her fault. If it wasn't for all the shit that she had done, walking around with her ass hanging out, loudly moaning while she masturbated in her room, getting caught being plowed on our kitchen table, then I wouldn't even have been in the state that I was in.

Then a thought crossed my mind. Maybe she had been intentionally teasing me this whole time. It made sense. I mean, she knew that I would see her walking around in her thongs. She had to have known how loud she was when she was cumming in her room. Then I started to suspect that she wanted me to find her in her room on Saturday. Maybe she wanted me to see her like that. Hell, maybe jacking me off into her panties had gotten her hot. Maybe it wasn't just to humiliate me.

I don't like being messed with, so these new thoughts made me very angry. I stayed on campus until 6:30 or so, fuming at what my sister was doing to me. I walked back to the apartment. When I opened the door, I saw my sister sitting on the couch watching TV and having a snack.

"Oh, hey there, pervert," she said to me. And, that did it. I made a decision right there. She needed to be punished. I went upstairs and opened the drawer to my nightstand. I grabbed the bottle of lube I kept there and ran back downstairs. I stood between the TV and my sister, an angry look in my eye. My sister stood up and started to walk towards the kitchen. She looked at what I was holding and said,

"What? Does the perv-boy want another handjob? Can't get enough of your sister, huh?" I walked over to her, grabbed her forcefully by the shoulders and moved her over to the side of the couch. Then I turned her around and bent her over the arm of the couch, her face smashing into the cushions. Her ass was now the highest point of her body and it jiggled as she tried to shuffle away, but I held her down, pushing her face hard into the couch cushion.

"Matt, what the fuck are you doing?" she said, a touch of fear in her voice.

"You've been teasing me ever since you moved in. Almost every day I have to look at you in your skimpy underwear and listen to the sounds of you fucking in your room."

"What? No... no I-"

"I've had it, Jenna. You need to be taught a lesson. One that you're not likely to forget." I grabbed her short shorts by the waistband and pulled them down to her knees. I saw that she was still wearing her pink panties from earlier.

My cum had left a large stain in the bottom of them. That turned me on, actually. I gave her big butt a slap. I liked the way her cheeks shook, so I slapped it again. She wriggled underneath me, trying to get out, but I was able to hold her down.

I pulled down her panties, exposing her pussy and ass. I immediately felt a steamy warmth coming off of her. I grabbed the bottle of lube I had brought down with me and upended it above her ass, spilling a sizeable amount of it down in between her butt cheeks. Then I took my middle finger and worked some of the lube into her asshole. Jenna turned her head to the side and gasped as she realized what I was doing.

"No. No no, Matt please don't," she said. The panic in her voice was clear. I slid my shorts down and saw that my cock was already fully hard from all of this. I worked a little lube around my dick for good measure.

"Call me a sister fucker will you?" I said. "I'll show you a sister fucker." I put the head of my cock up against her puckered, brown asshole and pressed firmly. The head of my cock slipped inside and my sister gave a high pitched squeal. Her butthole suddenly tensed up, squeezing around the head of my dick. I put my hips into it and plowed forward a couple of inches to the sound of a deep, guttural "Unnngh" from Jenna.

"This is going to be a whole lot easier for you if you relax your ass," I said. Jenna's mouth was hanging open and her eyes were closed. She concentrated real hard on relaxing her ass, and soon it was no longer squeezing down on my dick. Relaxed, her ass was still very tight. It was a pleasant surprise, actually. Going in, I wasn't sure whether Jenna would have a tight butthole, or if she would be loose.

I slowly worked my cock in and out of her, forcing her ass to adjust to the size of my cock. My dick was as hard as I had ever seen it. During my slow backstrokes, when most of my dick would come out of Jenna's butt, I could see veins bulging along my shaft. I had only ever had anal sex once before and it was the best sexual experience I had ever had. Now, with the added perverseness that it was my sister's ass I was fucking, my cock was in heaven.

In no time at all, Jenna's ass had adjusted to the size of my dick. Now the fun could really begin. I started humping her ass at a good starting pace. Every thrust of mine drove me deep into her tight butthole. My balls would slap against her pussy and my hips sent a quiver through her big ass cheeks. That was my favorite part, watching her butt shake with each thrust. As I began speeding up, I heard my sister grunting every time my cock buried itself to the hilt.

"Unngh, unnngh, aaaaahuuungh. Matt... please... my ass... UUUUNNNNNGGHHH!" I thrust deep and hard into her, burying my cock deep in her ass. I continued this deep thrusting, my sister's grunts turning me on. After a couple of minutes, I could have sworn I heard her moaning a little in between strokes. Then I started to feel her pushing back into me with her hips.

"Yeah, my little sister loves getting fucked up her big ass, doesn't she?" I said. Jenna didn't respond. She seemed to be in a world all her own. But, it was clear from her face that she was now starting to enjoy the anal pounding I was giving her. "Jenna, Jenna. Look at you, getting fucked up your slutty little butthole. Looks like you're a bigger pervert than I am after all."

I picked up the pace a little. Jenna was now openly moaning. I couldn't believe what a dirty anal whore my sister was. Just the thought of it was getting me hot. Soon, I could feel the cum boiling down in my balls. I was going to blow my load soon and it was going right up Jenna's ass.

"Congratulations, Jenna," I said. "You're going to make me cum twice today. Are you ready?" I didn't wait for an answer. Instead, I started pounding away at her asshole as hard as I could, and thrust my cock in and out at the quickest speed I could muster. Jenna's eyes shot wide open and she let out a long, high pitched shriek as my dick ripped her apart.

Her ass was violently shaking underneath me with each deep thrust. She clutched the side of the couch cushion with her arms and bit down on it to suppress her screaming. Jenna then started making deep, guttural sounds and her eyes became glazed over.

I continued to pound her big ass all the way through my orgasm. My dick spasmed inside her and I shot stream after stream deep into her hole. I gave one last deep thrust into her then slowly pulled my cock out of her ass. As it slid out of her now slick butthole, I saw that her ass was gaping wide open. Without my dick to hold it open, though, it slowly started to close up again.

Finally, I released my hold on my sister and stepped back a couple of paces. She didn't move, remaining very still, her arms had fallen out to the side. She looked so helpless as she rotated her face back into the cushion.

"Let's get a something straight," I said. "You're my bitch." I reached down and pulled my pants up. "Go ahead and keep teasing my like you do. We both know why you do it." I took one last look at my sister, bent over the couch with her ass up in the air. A bit of my cum was now leaking out of her ass. I smiled and went upstairs.

I lay down on my bed and recounted all the events that had happened that day. Quite an amazing turn of events. It was still early, but I was completely worn out. I fell asleep thinking about how I had just made my sister my fuck doll. I imagined different ways I wanted to fuck her in the future. Jenna was mine to do with what I wanted.

But, it seemed I had underestimated her once again. This was the last time I ever did.

I woke up in the middle of the night to Jenna shaking me awake. She was on top of me, straddling my chest. It took a few seconds for me to realize what was going on. The first thing I noticed was that Jenna was wearing an incredibly sexy outfit.

She had on a black corset that looked like it was made out of latex or vinyl. The way it pushed her tits up made them look mouthwatering. She had on expensive looking black, lace underwear, and black, thigh-high boots. I absolutely love thigh high boots. Jenna was looking down at me with a wicked grin on her face. The next thing that I noticed was that I was naked too. Wow, she had even taken my clothes off.

I smiled and said, "Back for some more, huh?"

"I suppose so," she said. Just then, I made my last realization. I was tied to the corners of my bed.

"Kind of kinky, huh?" I said.

"Oh, Matty. You have no idea." Jenna stood up on my bed, took off her panties, and turned around, giving me a full view of her ass. She moved up a ways towards my head and squatted down, her ass about a foot away from my face.

"You were pretty rough on my ass earlier," she said. "Kiss it and make it better." Before I could protest, her ass landed on my face, smothering me underneath it. In a circular motion, she ground her ass onto me. Then she reached back and spread her cheeks, exposing her asshole. She positioned herself so that her asshole was touching my lips.

"Kiss it, Matt."

"What? Kiss your asshole?" I managed to get out from beneath her thick butt cheeks.

"Kiss it like a good brother," said Jenna. I didn't want to do it. I had never put my mouth on a girl's butthole before. That's disgusting. But, I could clearly see that I had little choice. I was tied up and something in Jenna's voice sounded like she meant business. So, timidly, I pushed my lips together and gave Jenna's brown little pucker a small kiss.

"Aaaah, good boy," said Jenna on top of me. "But, that didn't make it feel all better. I think you're going to have to lick it real good for me."

"What?" I protested beneath her. "I can't do that."

"You can and you will. Now, lick my ass or else you'll be punished." She brought her open hand down onto my stomach, slapping it hard. I yelped, but still didn't start licking. Three more times she slapped me before I broke down and stuck my tongue out and lapped at her bitter asshole.

"Mmmmm," moaned Jenna. "That's just what I need. Keep licking it like a good boy." Jenna started rubbing her clit and moaning. After a while, it wasn't so bad. The fact that this was turning her on so much was actually starting to turn me on too. I loved listening to Jenna moan and my dick was starting to respond to it. I continued to lick her ass for about a minute and then Jenna climbed off of my face.

She positioned herself at the bottom of the bed with her head near my crotch. She was staring at my dick and slowly began playing with it a little, running a finger up the length of it then squeezing the tip a bit.

"You know, as long as both of us are getting all of our little perversions out in the open today, I must admit that I've always wanted to know what my brother's cock tasted like," she said. Then she opened her mouth wide and swallowed all of my cock, and I do mean the entirety of it.

Her lips were settled on top of my balls and she held it there for a bit, the tip of my cock a ways down her throat. I had never had someone deepthroat me before. My eyes almost rolled back into my head at the sensation. After about ten seconds, Jenna came up gasping for air. She looked up at me and smiled again.

"See, Matt," she said. "Who says I'm not a loving sister? Do you like it when I take your whole cock like that?"

"Oh my God yes. That feels so good."

"Yeah, do you like it when I do this?" Jenna kept eye contact with me while she lowered her head down onto my cock. She continued looking at me even as she started sucking it, and boy did she suck it. I started moaning from the pleasure of it. But, then she put her teeth lightly against my dick and started slowly grating her way down my shaft. It fucking hurt.

"Ow, what the fuck, Jenna? Ow! Stop it. That fucking hurts." Jenna was still looking up at me and smiled as I cried out, but she continued to use her teeth on my dick for another thirty seconds or so. Then she grabbed me firmly by the shaft and circled the tip with her tongue. Unfortunately, she didn't do that for very long. She stood up off of the bed.

"Let's move on, shall we?" she said. "I'm going to turn you over now. If you try to break free of the ropes while I'm doing this, I'm going to hurt you."

"You already hurt me," I said. "My cock feels like somebody just chewed on it."

"Oh, poor, naïve Matt. That was just a warm-up." I didn't like the way that she said that. My sister was starting to scare me now. What happened to me being the dominant one? Wasn't she supposed to be my bitch now?

It took some time, but she eventually got me turned over. She had to untie one rope at a time and retie it to the opposite post. I thought about trying to break free, but decided against it. I didn't want to find out what she might do to me if I did. Also, there were always three ropes holding me down at all times and the knots were strong. I wondered where she learned to tie such a good knot. Maybe I wasn't the first guy she'd tied up before.

It took a little while, but eventually I was lying face down on my bed, tied to each corner. I couldn't think of any reason that she wanted me on my stomach though.

"I have to get something out of my room. I'll be right back. Don't go anywhere," Jenna said with a little laugh to herself. Yeah, as if I had a choice. She walked out of my room and across the hall, her heels clicking loudly on the floor as she walked. She was only gone for a minute or so, but that was enough to make me worry. What could she possibly be getting? What was I in for?

I heard her heels clicking again, making her way back into my room. The clicking stopped beside my bed. I turned my head to look at her. Instead, I came face to face with a big strap-on dildo that my sister had put on. My eyes went wide and my jaw dropped. Jenna laughed at my reaction.

"Don't worry, bro. I bet you're a natural," Jenna said. The dildo was probably averaged size, but, with it inches from my face, it seemed like a monster. It was realistic looking. It had a natural flesh color and even had veins bulging along it.

Jenna put one hand on the base of the dildo, one hand on the back of my head, and shoved the dildo into my mouth. She wasted no time before fucking my face with her big strap-on. I choked on it at first and she pulled it out.

"Suck my dick, Matt," she ordered, and stuffed it back in. This time, she put both of her hands on the back of my head and pushed me up and down on it. I must have looked ridiculous, but my sister seemed to be loving it.

"That's it, bro. Suck your sister's big cock." She continued to fuck my mouth for two minutes or so, changing speed at irregular intervals. The friction on her pussy was getting her hot. I could smell the aroma of her sex coming from her crotch. She gave me two or three last deep thrusts, which I started to gag on, then took the dildo out of my mouth.

I looked up at her and she smiled wickedly at me. I felt an incredible sense of defeat at that. I thought I was the one dominating my sister, but she was showing me who was really in control. She picked up a big bottle of lube and started to walk to the bottom of the bed.

"Time for your last lesson of the night," she said. Then she started to climb onto the bed, between my legs. I suddenly became very aware of what she intended to do.

"No," I pleaded. "No no. Not that. Jenna don't. Please."

"Please don't what?" said Jenna.

"Please don't," I repeated.

"Please don't what?" said Jenna, and she slapped me hard on my ass. I swallowed hard to help get the words out.

"Please don't... fuck me in the ass." I turned my head to look behind me as best I could. I saw Jenna smiling that same wicked smile.

"Ok," she said. "I won't fuck your ass." All the muscles in my body relaxed a bit. But that didn't last long. "I will, however, plow your ass. I'm going to pound your little asshole, Matt. I'm going to shove it in deep and turn you into a little sissy boy. And, you know what? By the time I finish reaming your little butthole, you're going to cum for me."

Jenna squirted some lube onto her hand and worked it up and down her rubber cock. Then she put a little on my ass and rubbed it all over my asshole. Finally, she took the whole bottle of lube and shoved the nozzle into my ass. Once it was inside, Jenna squeezed, forcing a large amount of lube into my ass.

"You're tense. Don't worry. You're going to love it." Jenna threw the bottle of lube to the side and positioned her hips right above my ass. She lined up her cock and I felt it press against my asshole. "Karma's a bitch, and so am I," said Jenna. Then she thrust forward, shoving a large portion of the strap-on up my ass.

I clenched my teeth and let out a low grunt. The feeling was incredible. It hurt so much. I wished that she had gone in slowly. The feeling of being stretched by that dildo was sending all sorts of pain through my body.

Jenna stayed motionless on top of me for a little bit. At least she was going to let my body adjust now. Slowly but surely she started to work the dildo in and out of my ass. It felt unnatural to me, like I was taking a massive shit, but in reverse. My ass felt so full of my sister's cock.

After a few minutes of very little movement, Jenna started to hump my ass. My ass had started to get used to the dildo and it was moving in and out much easier now. The lube was making slopping noises as Jenna began fucking me proper. Luckily, I was able to relax my ass enough to ease the strain of taking the dick.

Once I was able to do that, the feeling was much different. I still felt completely full, but that didn't seem so bad anymore. In fact, the steady rhythm of Jenna's strap-on moving in and out of me was starting to make me feel good. I closed my eyes and pictured Jenna's hips driving into me right behind me, her ass flexing with each thrust.

I was really starting to enjoy myself now. I lost myself in the sensations that were coming from my ass, and I did something I shouldn't have - I accidently moaned a little. Jenna stopped her steady humping. Then she burst out laughing.

"Oh my God. No. Fucking. Way. Did you just moan?" Jenna began laughing again. My face turned bright red. "I can't believe that. You just moaned while I was fucking you in the ass. I haven't even been fucking you that long. Has your ass already adjusted that much? I guess I was right, you're a natural." Jenna resumed her thrusting, this time going deeper and a little quicker.

"Uuungh," I grunted at the change of pace.

"I can't believe my brother is such a sissy boy. And, here I thought that I was the anal whore. You are loving this, aren't you? Keep moaning. I like that." I kept my mouth shut. "I said, moan." Jenna drove the strap-on as deep as it would go. I was now taking her balls deep. The sudden surprise of the dildo burying itself in my ass so deep forced my mouth open.