More - Sister

“Hey Simone, I really enjoyed that 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 **** James?” sighing playfully she adds, “Alright alright, I think I can whip up something you’d like. Give me a moment to compile.”

I don’t even feel much of a transition before I find myself drinking beers on the porch with my sister. My sis says she needs to take a leak and I use 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 another 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 must 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. Seeing my expression Jenna says, “Jesus why do you look so worried?”

Calming down I replied, “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.”

After an awkward pause, “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 bursts into laughter, “Oh, right,” she gets 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?”

Sighing, “That was just a turn of phrase.”

“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”

Chugging down the last of her beer Jen says, “Yeah, I just don’t see why not”. She then quickly, in one smooth motion pulls down her shorts, underwear and all and makes her way over to my bed before flopping back on it and spreading her legs wide open. Once on my bed, she says, “Well? Go ahead and get it out of your system.”

Jen was into all sorts of sports, swimming, volleyball, lacrosse just to name a few; meaning 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 laying 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 pull out my already stiff cock and line it up with her asshole. Spitting on her hole, I rub 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 see Jens face, she was just watching me curiously, “So, everything you expected or what?”

“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.”

Shrugging Jen replies, “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.”

Ecstatic about how things are, I pull my cock out all the way, move it up to her pussy and rub it a few times before Jen flinches back, “Hey! Wrong hole!” Jen yells out 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.”

Laughing I say, “Fuck that’s so hot. 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 put my cock back into her ass and resume fucking it at a steady pace.

Jen replies, “Easy on there, don’t fall in love now.”

“Too late. You’re the best sister in the world and I love you.”

“Gross.”

As the minutes tick by, I start fucking Jens ass faster, harder and deeper, instead of being satisfied, I get more hungry as I keep assfucking her. Soon enough, every thrust is making her tits bounce gorgeously and rocking the bed, Jens looks at me with more and more surprise the more aggressive I get.

“Hey Jen, what are the rules here? I don’t wanna push things too far for you.”

“Iunno, just do whatever you want, I’ll call out if there’s something I don’t like.”

After 10 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 grab Jen by her ankles and lift them up, so I can piledrive into her ass but even that isn’t enough. I’m overcome with the urge to fill her asshole, turn it inside out and churn her guts, I’m slamming into her asshole as hard as I can from above while her legs are up in the air, pulling out all the way only to do it all over again. I only manage to get it in the right hole because Jens being helpful and using her hands to guide me back into her ass. Despite saying she didn’t mind anal, she’s starting to look uncomfortable.

After almost half an hour of relentlessly bottoming out in her asshole, I hear Jen mutter under her breath, “I think I may have bitten off more than I can chew,” before adding more loudly, “Jesus Chirst Sam, you think you’ve had enough?”

“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 pull out of Jen and she sighs with relief when I do, I see her asshole gape lewdly with the skin around it an angry shade of red, that can’t be comfortable but I get off on the fact she’s taking it for me. Jen kneels down on her knees and I get behind her, she nods to me she’s ready again and I desperately shove my cock back inside her asshole and start pounding into hungrily again. I hug her from behind and maul her tits as I continue slamming up into her ass, I avoid pulling out all the way this time though. Despite telling me to stay away from her pussy, the pain in her ass gets so bad she eventually relents and starts rubbing her pussy to try and relieve it.”

“Your asshole feelings amazing wrapped around my cock Jen, I can’t get enough of it.”

Grunting she replies, “Unf, well I’m glad you’re having fun. Think you’ll be done soon?”

“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 use your ass like this, I’ll do whatever you want.”

I spend another 10 minutes hammering into Jens asshole in that position before I’ve finally had enough and start to cum. Hugging Jen tight, I jam myself deep as I can manage into Jens ass and let loose into her ass, filling it with my cum, pounding into her with every spurt. I stay inside her until I start going soft, my cock wetly flops out when I pull back. With nothing to hold in the cum, a small flood of jizz follows it out, sliding down Jens inner thighs. Her asshole doesn’t close for the longest time and looks puffy and very pinkish red.

Jen moves her hand back to touch her asshole and when her fingers brush against it, she flinches. “Ow. That hurt.” Laying back down on her back, she points her ass at the mirror in my room so she can get a better look at the state of her ass. 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 add 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.”

Shyly I reply “Sorry. Think I got 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 feel devastated and crestfallen but hardly surprised considering.

Jen quickly then adds, “Jesus, relax Sam I’m only fucking with you, 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. I’m going to have soooo much fun I bet,” she says sarcastically.

“Jen, you’re the best sister in the world and I love you.”

“Gross. I’m gonna go take a shower,” She walks off to my bathroom leaving me sitting there happy with the way things turned out.