The Sim - Sister, Jen

"Hey Simone, I really enjoyed that last little sister story, do you think you could come up with something similar for me? It doesn't have to be y'know, my sister. Same deal as before, just make me think it is and do another information dump."

"More incest James?" Simone asked with fake shock. "Alright alright, I think I can whip up something you'd like. Give me a moment to compile."

I didn't even feel much of a transition before I found myself drinking beers on the porch with my sister. My sis said she needed to take a leak and I used the time to digest all the new information and memories I've been given.

Five minutes passed before I thought to myself it was taking her quite a while. Ten more passed before I was seriously wondering what was going on. I gave it a final five before I went in to see what was up. Instead of finding her in the bathroom, I found her sitting on my chair in my room scrolling through some folder. I was going to say something snarky but as I got closer I realized what she was looking at, my porn folder. She was scrolling through the folder and playing the occasional video. Shit shit shit. This would've been fine if I had just regular porn like every other guy but instead, I had nothing but anal on it. It was a fetish I couldn't get over, I almost couldn't cum unless anal was involved, now instead of being funny, I'd just end up looking like a sexual deviant.

Jen have heard me because she turned around. I was expecting disgust but she only had a sly look on her face. Didn't expect that.

"I didn't expect that," she said pointing a thumb over her shoulder at a video she had opened up of an amateur girl getting fucked in the ass missionary. "Jesus why do you look so worried?" She said after seeing my expression.

I forced myself to calm down. "I... I thought you'd be freaked at seeing the type of porn I'm into. I was afraid you'd get mad or disgusted."

"Well calm your tits, I'm not, a guy into anal is nothing new. It's just surprising is all, I mean look at you, into all this rough stuff, I really wouldn't have guessed this Sam. I mean you are really into butts, there's almost nothing but anal here. Heh, now I can totally see why you went for Melissa, with an ass like hers."

"Yeah, actually we've never done it there. In fact, I've never actually done it there with any girl."

"Oh, actually, that makes a lot more sense; this is like your white whale."

"Hey it's not an obsession, it's just, a strong preference is all."

"Uh huh."

An awkward pause stretched. "Look, I'm only bringing this up because you were snooping in the first place, otherwise I'd keep it to myself. But Jen, we've always been close, I figure now that you know, maybe you could help me?"

"Wow, wow, wooooooow, just. Wow! I actually can't believe you're actually asking your sister to let you buttfuck her. God damn, that's really something Sam."

"What?! Jesus, no, I meant, could you be like my wingman, tell me which girls are into anal that I could try my luck with, stuff like that."

Jen burst into laughter. "Oh, right," she got out in between laughs. "Yup that makes more sense. I think I could manage that".

"Really? That'd honestly be so cool. It's on my mind a lot these days and I figure if I could just do it, get it out of my system, I'd stop obsessing so much."

"I thought you said it wasn't an obsession?"

"That was just a turn of phrase," I said sighing.

"Uh huh, sure... Y'know... I was just busting your balls before, I would've said OK if you were actually asking."

"Asking what?"

"For me to 'help out', end air quotes."

It took me a moment to process what she meant, I still couldn't quite believe my ears, I figured she was just fucking with me. "What are you saying?"

"I dunno, it just doesn't seem like that big a deal to me. You've got a problem only ass can fix and I've got an ass, a hot one too I might add, problem solved. Besides, it's not like we'd be having sex, not proper sex at least, you'd just put it in my ass, that doesn't seem as wrong."

I initially felt the whole conversation was completely wrong but that feeling was quickly smothered, instead the longer Jen talked, the harder I grew and the less bothered I felt about the whole thing.

"Jen, do you really mean that? This is seriously fucking up my composure, you so better not be messing with me right now."

"Yeah, I just don't see why not," she said chugging down the last of her beer. Then quickly, in one smooth motion, she pulled down her shorts, underwear and all before making her way over to my bed and flopping back on it. "Well? Go ahead and get it out of your system," she said, lazily spreading open her legs.

Jen was into all sorts of sports, swimming, volleyball, lacrosse just to name a few; so she had a body to die for, it was tight and toned in all the right ways without a drop of fat on it. I'm ashamed to admit even before today, I'd snuck more than a few glances at her tight little ass. Seeing her lying there, waiting for me to use her demolished any and every doubt I might have had. All I could think about was getting inside her ass. Walking over to her, I pulled out my already stiff cock and lined it up with her asshole. Spitting on her hole, I rubbed the saliva in with my knob and started to press in.

Physically, it actually felt a bit disappointing, the tightness tapered off quickly once inside but the thought, the idea of being in a girls ass, my own sister's, more than made up for that. It's funny, I was actually getting off more from the situation than from her ass.

As I enjoyed the feelings and slowly pumped into her, I saw Jens face, she was just watching me curiously. "So, everything you expected or what?"

The gentle question while I was buttfucking her somehow made things even better.

"It's weird. It feels good, amazing actually, but it's not all physical, it's like, just knowing I'm in your asshole, that you're letting me assfuck you is driving me crazy. What about you? How's it feel for you?"

"I mean, I'm not gonna cum from it, but I don't hate it. I've had boyfriends put it up my ass before, but honestly, I've never really understood the appeal it's just something I'm OK with doing occasionally."

"Just so you know, it might take more than a few occasions to work this out of my system."

"We see each other pretty often, long as you don't piss me off too much, you can use my ass whenever we hang out, I don't see any problems," Jen said shrugging.

Ecstatic about how things were, I pulled my cock out all the way, move it up to her pussy and rub it a few times.

Jen flinches back. "Hey! Wrong hole!" she yelps before reaching down and pushing my cock away with her hand. "Not cool Sam. OK, I don't think I made myself clear. We're not having sex, I'm not having sex with you, you're just using my ass a little bit. This is just me doing you a favor so you better keep out of my pussy buster."

"Fuck that's so hot," I said laughing. "OK I can do that, no complaints here. I actually love that you're gonna be anal only, like the perfect girl for me," I said. I placed my cock back into her ass and resumed fucking it at a steady pace.

"Easy on there, don't fall in love now," Jen said.

"Too late."

"Gross."

"Really, you're the best sister in the world and I love you."

Jen rolled her eyes. "After I let you cram your cock in my ass, suddenly I'm the best sister in the world? Shocking."

As the minutes ticked by, I started fucking Jens ass faster, harder and deeper. Instead of being satisfied, I got hungrier as I keep assfucking her. Soon enough, every thrust was making her tits bounce gorgeously and rocking the bed. Jen's expression grew more and more surprise the more aggressive I get.

"Wow Sam, I really, did not expect this," she said. "I kinda always assumed you were the gentle please and thank you type."

"Well, you figured out," I said. "So Jen, what are the rules here? I don't wanna push things too far with you."

"Iunno, just do whatever you want, I'll call out if there's something I don't like."

After ten more minutes, I'm still not any less hungry for her ass. In fact the longer I pound into it, the more I lose control. I eventually grabbed Jen by her ankles and lifted them up, so I could piledrive into her ass but even that wasn't enough. I'm overcome with the urge to fill her asshole, turn it inside out and churn her guts. I slammed into her asshole as hard as I could from above while her legs were up in the air, pulling out all the way only to do it all over again. I only managed to get it in the right hole because Jen was being helpful and using her hands to guide me back into her ass. Despite saying she didn't mind anal, she started to look uncomfortable.

"I think I may have bitten off more than I can chew," I heard Jen mutter under her breath after more than half an hour of relentlessly bottoming out in her asshole. "Jesus Chirst Sam, you think you've had enough?" she asked.

"Are you OK? Do you want me to stop?" I desperately didn't want to stop until her asshole was a ruined mess but I asked anyway.

"Fuck me, this is a bit more than my boyfriend's ever did, you don't have to stop just... just let's change positions."

I reluctantly pulled out of Jen and she sighs with relief when I do. I saw her asshole gaped lewdly with the skin around it an angry shade of red. That couldn't be comfortable but I get off on the fact she was taking it for me. Jen kneeled down on her knees and I got behind her. She nodded to me she was ready again and I desperately shoved my cock back inside her ass and start pounding into hungrily again. I hugged her from behind and mauled her tits as I continued slamming up into her ass, though I avoided pulling all the way out this time. Despite telling me to stay away from her pussy, the pain in her ass must have gotten so bad she eventually relented and started rubbing her pussy to try and relieve it.

"Your asshole feels amazing wrapped around my cock Jen, I can't get enough of it," I breathed out.

"Unf, well I'm glad you're having fun. Think you'll be done soon?" she said grunting.

"Sorry Jen, I don't think I'll be done for a while."

"Ugh, just great. Fine, but you better appreciate this, I mean it, if I ever ask you for a favor, you are so dropping everything to help me out."

"Jen, if it means I get used your ass like this, I'll do whatever you want."

I spent another ten minutes hammering into Jens asshole in that position before I finally had enough. Hugging Jen tight, I jammed myself as deep as I could and let loose, filling her ass with cum, rutting into her with every spurt. I stayed inside until my cock went soft. It wetly flopped out when I finally pulled back.

With nothing to hold in the cum, a small flood of jizz poured out, sliding down Jens inner thighs. Her asshole looks satisfyingly puffy and very pinkish red, it doesn't close for the longest time. I couldn't help but enjoy the fact I did that.

Jen moved her hand back to touch her asshole and when her fingers brush against it, she flinches. "Ow. That hurt. You at least get it out of your system?"

"For now."

Jen rolled her eyes. Lying back down on her back, she pointed her ass at the mirror in my room so she could get a better look at the state of it. Seeing herself in the mirror, her eyebrows shoot up a little in surprise. "Ow. Did I say ow? Fuck, I think my asshole is completely wrecked, just look at it."

"It's a good look, suits you I think," I said cheekily.

She scoops up some of the cum on her thighs with her fingers and flicks it at me. "I'm gonna have trouble sitting never minding walking for a week."

"Sorry," I said shyly. "Think I may have gotten a bit carried away. I'll be more careful next time."

"Next time he says, like I'm not reconsidering after that. I just let you fuck up my ass and leave it ruined mess, that's not enough for you?"

I immediately felt devastated and crestfallen but hardly surprised considering.

"Jesus, relax Sam I'm only fucking with you," Jen quickly added after seeing my reaction. "No need to look like a kicked puppy. I said I'd help you work it out of your system and that's what I'll do."

"So, you mean next week I'll-"

"Yes, you can try out my ass again when I see you next week. Hell, if you play your cards right, I might even let you try doing a little ass to mouth, I saw you like that too," Jen said with a sly look.

"That's on the table?" I stuttered out.

Jen laughed like a hyena at the look on my face.

"It's not right to tease a guy like that," I said with a sigh.

"Who said I'm teasing?"

I stared straight at her. "Jen..."

She cut me off. "If you promise me a few favors, I might just be up for trying it. Scouts honour."

I shook off the shock. "Jen, you're the best sister in the world and I love you. I don't know what I did to deserve you."

"Gross. I'm gonna go take a shower," Jen said, brushing me off and walking away with a slightly noticeably limp.