Roomies

NOTE: This story contains many different fetishes -- incest, anal, public sex, non-consent, femdom, bondage, pegging. If you object to any of this sort of material, please do not read this story. If this sounds like something you will enjoy, please read on. This story is the first in a coming series. The characters engage in many different perversions to show the range of things the series will involve. The next chapters will probably be shorter than this, but I thought it was the best way to introduce the characters and the special relationship they have. Thank you for reading, and please comment so I can make the series as wonderful as possible.

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There comes a time in every man's life when he has to accept that his sister is a sexual being. For me, that time came when my sister and I were sharing an apartment in college. Specifically, that time came when my dick was shoved balls deep all the way up her big butt in our living room.

It was my third year of college and I had finally moved out of the dorms and found a nice two bedroom apartment. The problem was I couldn't find a roommate. I didn't have many friends and the few I had were already living in other places.

However, my little sister Jenna had just graduated from high school and was planning on going to the same school as me. I asked her if she wanted to live with me to save some money. She didn't really want to live in the dorms anyways, so she agreed.

I grew up in Missouri -- part of the fucking Bible Belt. My parents were very religious, and they kind of messed me up. I lived a sheltered life growing up, and the far right religious atmosphere had me constantly scared that most things I wanted to do would send me to hell. My parents had me so terrified of sex that I never even had a girlfriend until I left for college.

When I started college, the change was fairly quick. I started rejecting most of my preconceptions about the world and started living how I wanted to live. I started going to parties, dating girls and everything else a college kid does.

My parents and I don't really speak all that much now. They found out about what I was doing at school and sort of cut me off. It seems harsh, but there was this one fight, things were said, it got personal. Anyways, now my sister is the only one in my family I really speak to.

My sister moved in, and I thought everything was going great. However, I completely misjudged what living with my sister would be like. The image I had of my sister in my head was a sweet little Christian girl who just graduated from high school and didn't really know what the real world was like.

Apparently, she didn't buy into all the religious stuff like I did growing up. My sister was fucking wild. I took her to a party with me the night she moved in. I thought I was going to have to show her the ropes so to speak. I underestimated her. She held her own. In fact, she was beating me at most of the drinking games we played. It clearly was not her first party.

"Alright," I thought. "My sister is fucking awesome. Living with her is going to be great." I underestimated her again. The next morning I woke up, very hung over. I got a bowl of cereal from the kitchen and sat down to watch TV in the living room.

About a half an hour later, Jenna walked downstairs and crossed right in front of me to go to the kitchen. As she passed by, I saw that she was wearing a small t-shirt and a thong -- that's all. Needless to say, I was a bit shocked by it. Not wanting to make it weird, though, I didn't say anything.

I mean, we did grow up in the same house. We had even seen each other naked before once or twice. But, I had not seen her much since she started to fill out. My sister had a great body. She was fairly tall, only a few inches shorter than me. Her long legs looked so good running all the way up to her big butt and curvy hips. I focused on the pale cheeks of her ass as she bent over to get something out of the fridge. Her ass truly was amazing.

Then my eyes inadvertently made their way up to her chest. Her perky round tits were pressing against her t-shirt, trying to get free. They were pretty large boobs, C cups. Now that I had started thinking about my sister's body, I realized that she had always been an attractive girl. She had long, light-brown hair and a beautiful, angular face with gorgeous green eyes.

As Jenna came over to sit with me in the living room, I realized that I was hard. Naturally, I was mortified that my sister had just given me a boner. So, I just continued to eat my cereal and watch TV until my erection went away. Then I went about the rest of my day as normal. I thought that would be the end of it. I was wrong.

Over the next couple of weeks, I started to get to know my sister. And, I mean I really got to know her. The thong incident was not a one-time thing. She would wear next to nothing all the time. It was as if I wasn't even there. Her ass would be spilling out of her underwear, and she didn't even seem to care if I was in the room. I thought having my own place would be relaxing, but it was hard to relax when my sister was giving me a peep show.

The way she dressed wasn't even the worst of it. The way she acted was even worse. I learned quickly that my sister was very sexually active. Both of our bedrooms made up the whole upstairs. It wasn't the biggest space, and we shared a wall. Sometimes I would be in my room and hear her masturbating over in her room. Sometimes she would bring some guy home and I would be kept up all night by the sound of them fucking next door. It wasn't just awkward moaning either. I could hear them dirty talking to each other, Jenna telling the guy to smack her ass or to give it to her harder.

Once, I came home from a party and walked in on her and some guy fucking in the kitchen. He had her bent over the kitchen table and was giving it to her good and hard. He stopped when he saw me, thinking I might be her boyfriend.

"Who the fuck is this?" he asked Jenna.

"Don't worry, that's just my roommate," Jenna said. Jenna made a pleading face at me. Apparently, she really wanted to fuck this guy. So, I played along, pretending it was no big deal and walked out of the kitchen.

Before I even got to the stairs, I heard them start fucking again. After that, I had a little talk with her, telling her how weird it was having her act like I wasn't there all the time and fucking guys in our kitchen. She told me chill out, but did promise to only have sex with guys in her own room.

In October, I got a job at a bar, working nights. It was nice to have someplace to get away from my sister. Truth be told, she was starting to turn me on on the regular. It wasn't my fault. Anyone would get a chubby looking at my sister in her underwear all the time. But, it was getting bad.

Just a week before I started my job at the bar, Jenna had popped into my head while I was masturbating one night. I couldn't get her out of my head and I ended up finishing while thinking about her. A few days after that, I was jacking off to the sound of her moaning next door. So, my new job was sort of saving me from my own sick thoughts.

The shifts I worked usually ended around two or three in the morning, depending on if I was closing, so I got home late quite a bit. The down side of this was that Jenna saw my time at work as time when the whole apartment was hers alone. More than a few times I came home and found Jenna's dildos in the living room. I guess she would masturbate on the couch and forget to clean up after herself when she went to bed.

It's safe to say that my sister and I had a strained relationship. But, one night changed us more completely than I ever thought possible, eventually creating a sexual dominance competition between us. It was a Saturday night and I had picked up a closing shift. I got home around 3:30 in the morning. It had been a long day and I just wanted to go upstairs and crash into my bed.

When I reached the top of the stairs, I saw that Jenna's bedroom light was on and her door was wide open. I looked inside, and there was Jenna passed out, lying face down on her bed. She was wearing a bra, but her pants were down around her ankles. At first, I thought that she had just come home drunk and passed out while taking off her clothes.

Then I noticed that a big, flesh-colored, rubber dildo was laying on her pillow. Another translucent, pink one was off to the side around her knee. And, the thing that made my dick almost jump out of my pants, a thinner, glass dildo with bumps along it was stuck in my sister's ass.

I couldn't believe what I was seeing. My sister had come home, started fucking herself with her dildos and shoved a glass dildo up her butt. Then she passed out with it still inside her. Even from the doorway, I could smell alcohol on her, so I thought I'd better at least make sure that she was alright. I walked over to her bedside and made sure she was breathing alright. She seemed fine, despite the overwhelming smell of booze coming off of her.

I touched her on the shoulder to see if she would wake up. I figured I could get her to at least get under her covers and maybe take the dildo out of her ass. That would make for an uncomfortable morning I would imagine. And, if she was as drunk as I thought she was, she wouldn't even remember me seeing her like this.

She didn't respond when I shook her shoulder. I shook a little harder. Still nothing. She was passed out hard. I decided I would just do it for her. I reached down to pull out the dildo, but stopped short. First, I thought, maybe I'll take a few pictures.

So, I took out my phone and snapped a few quick photos. I got a few different angles. I mostly focused on her big ass, with the glass dildo sticking up out of it. Then I got some shots from right behind her so I could get her pussy in the frame. Her legs were spread as wide as she could get them since her pants were around her ankles, but I still got a fairly good view of her pussy.

By the looks of things, she must have had a hell of a time fucking herself. There were big globs of her thick cum still oozing out of her pussy and even more plastered along the insides of her thighs. She had made quite a mess of her crotch and ass. Everywhere was covered in Jenna's cum and lube. A lot of it had already started drying and pasting itself to her skin.

Looking at my sister's depraved body, I suddenly noticed that I had unconsciously started to rub a very sizable erection through my pants. Then a very wicked idea came to me. I had planned on just jacking off to the pictures I had taken of her later in my room. But, with Jenna in the state that she was in, why not do it right here where I had the real thing in front of me?

I considered actually fucking her a little, but I quickly dismissed the idea. I didn't think I was capable of actually fucking my sister; while she was passed out nonetheless. I decided I'd better test the deepness of her sleep once again. So, I nudged her thigh. She had great thighs. She had some meat on them, while not looking fat.

Her thigh swayed back and forth a little at my touch, but she stayed passed out. I got a little more daring and actually grabbed her thigh, shaking it back and forth. The wave effect that this produced was incredibly sexy. The waves even made their way up into her ass, jiggling her big ass cheek around the glass dildo. She stayed asleep.

"Well, now or never," I said. I undid my belt and pulled my pants down just enough to get my cock out. Then I started stroking it. I felt so filthy doing it. Here I was with my pants down, stroking my dick to my drunk, passed out sister. My heart was racing at the thought that she might wake up and see me. So, I just decided to cum quickly and get out of there. It didn't take long before I could feel my cum ready to explode out of me.

I put one knee onto the side of my sister's bed and moved my dick close to her, aiming it towards the bottom of her ass. With all the fluids already there, I figured she wouldn't even notice my cum by the time she woke up. Stream after stream of hot cum shot out, landing all over my sister's ass. My orgasm was intense and left me drained.

By the time I finished, I had turned my sister into a cum covered whore. Cum was dripping down her cheeks and clinging to her thighs. A particularly large glob of cum had landed right at the base of the glass dildo and I watched it stream through her deep crack, making its way to her hole.

I pulled my pants up and fixed my belt. I took one last picture of my sister, covered in my cum. Then I finally decided to do what I had come in to do in the first place. I grabbed the glass dildo and started to pull it out. The bumpy dildo made a lot of slurping noises coming out of her lube-coated asshole.

As soon as it popped out of her, my sister's ass involuntarily made a farting sound. Yet another testament to what a filthy whore my sister was. Still, she did not wake up. I tossed the dildo to the side of her bed and put her blanket over her. Then I went into my room and feel asleep as soon as my head hit the pillow.

The next day was Sunday so it was a typical Netflix-watching afternoon. Jenna woke up around noon and staggered downstairs with a crazy hangover. At least she wasn't walking funny from having a dildo stuck in her ass all night. See, I did help. Both of us went about our business as usual. I acted like nothing had happened, and apparently she didn't know anything. That's what I was hoping for. I can't say for sure what she actually remembered doing the night before. Did she remember coming home and passing out while masturbating?

If so, she might think it strange that she woke up without the dildo up her butt. A moment of anxiety washed over me, but I soon dismissed it. Even if she thought it was weird, she would probably just assume that she pushed the dildo out of her ass in the middle of the night. She didn't have any reason to suspect me, did she? All my worry seemed to be for nothing. The day went by fairly normally. A sense of relief washed over me as I fell asleep that night.

The next day was a school day. I had class at 10:00, but Jenna didn't have any classes until 1:00 or so, so I didn't even see her before I left the apartment. I assumed she was still asleep. I walked across campus to my first class. It was in one of the larger buildings that had many classrooms in it, so the halls were pretty packed. My class was on the very bottom level, two floors below the main entrance.

By the time I got to the right floor, I was running a little late. The hallway had practically emptied since everyone's classes had just started. As I was walking past the men's room, somebody grabbed me from behind and pushed me through the door. I stumbled into the bathroom and just barely kept from falling down.

It was an older building still being used from the early half of the last century. The bathroom had an intricate tile floor that had become dirty looking over the years, and the high ceiling had several cracks. I turned around and saw that the person who pushed me in was my sister. She crossed the room, put her hands on me again and practically threw me into a wall, pinning my back against it.

"What's wrong, Matt? You look confused," Jenna said. Before I could answer, she grabbed the athletic shorts I was wearing, along with my underwear, and pulled them down to my ankles. Then she pinned me back to the wall with her left forearm so I couldn't pull them up. I was astonished at how forceful my little sister was. With her right hand, she gently cupped my balls and started fondling them.

"Oh, you perverted big brother of mine," she said. "Do you like my hands on your balls like this?"

"Jenna, what the fuck are you doing?" I said.

"Oh, come on, Matt. Maybe it will help if you grab my big titties." Her teasing, pouty voice was making me feel strange. She was entirely in control of this situation and she knew it. "Hmmm. You're not nearly as hard as you were the other night."

Oh shit. There it was. The explanation. She knew. I don't know how she found out, but somehow she clearly knew what I had done Saturday night. Had she actually woken up? Jenna continued to fondle my balls in her hand and I started to feel myself getting hard.

"There he is. There's our little friend," said Jenna.

I glanced towards the door, suddenly aware that anyone could walk in at any moment. Jenna saw where I was looking.

"Don't worry," she said. "No one will come in... unless you make too much noise."

"Jenna, this is beyond fucked up. Knock it off."

"I don't think so. You see, my big brother has been very naughty. I thought I was safe living with him, but now I see that he's just a sick little pervert, isn't he?" I didn't respond. "Isn't he?!" Jenna squeezed hard on my balls and I suppressed a yelp.

"Now," said Jenna, "I think I need to teach my brother a lesson." By this time, my dick was pretty hard. Jenna let go of my balls and wrapped her hand around my shaft. She started pumping my cock in her hand and waves of strange, awkward pleasure washed over me. She stopped for a second to spit into her hand. Then she resumed jacking me off, lubricating my dick with her spit. It felt amazing and my pleasure was evident on my face.

"Does my big brother like that?" said Jenna. "Does my brother like his little sister jacking him off?" I was torn between the shame I was feeling and the pleasure surging over my body. Jenna increased speed. "Yeah, my brother loves having his big dick stroked by his slutty little sister. He loves getting handjobs in public bathrooms, doesn't he? Any second, someone could walk in and see him with his sister's hand wrapped around his cock." She sped up again.

"Jenna... stop... please... stop," I said. I didn't know how long I would last.

"Oh no, I don't think I will stop. In fact, I think you're going to finish for me." Jenna removed her forearm from across my chest. I didn't even try to get away. She reached down and pulled off her short shorts. She was wearing a pair of pink, cotton panties. Then she did something I never expected. She put her thumb into the waistband in the front of her panties and pushed out, away from her body so I could see right down into her panties. I looked in and saw her pussy, her dark hair shaved short and neat.

She moved towards me and put the head of my penis into her panties, keeping them pulled open and exposed. Then she started jerking my dick hard, forcing the cum out of me. She was going to make me cum into her panties. I had never seen anything like it. I was staring at her pussy and was on the verge of shooting my load.

"Look at me," said Jenna. I looked up and saw that Jenna was staring at me. We made eye contact as she continued pumping away. A very serious look was on her face. "Look at you, you sick fuck," she said. "Your sister is giving you a handjob and you're loving it. You're about to cum aren't you? You're going to cum into your own sister's panties. You're nothing but a sick pervert. Now, cum. Cum into my panties you sick sister fucker."

I started to cum. Both of us looked down as stream after stream shot into Jenna's panties, filling them up. The cloth did a good job of catching the cum and soon a pool was forming in her panties. After five or so streams, my orgasm started to subside. Jenna moved her hips to spread the cum all around. I could see it staining the pink cloth all over, starting in the front and making its way to the back, around the bottom of her ass.

Jenna pulled her panties up tight. I imagined how my cum was now pressing firmly against her pussy and ass. Then she put her short shorts back on.

"See you later, you fucking pervert," she said. She turned her back to me and walked towards the door, leaving me with my dick hanging out. As she walked through the door, I could see a thin, shiny stream of cum dripping down the back of her thigh. And then she was gone.