- Sister

“Could you put me at home, living with my sister? Back when she was y’know, first discovering her sexuality? I uh, want to see what it’s like for someone to learn how to live in a free use world.”

“****? Oooookay. Hmmm, so something like origins of a butt slut?” Simone replies

Chuckling, “Hey, no judging. But yeah, something like that.”

“Can do, compiling now.”

The familiar sensation of my vision waxing and waning hit me again. By the time it was over I found myself in my old apartment. It was sorta frightening how accurate the place was, like they modeled it after the real thing. Hearing music coming from my sister Hannah’s room I figured she was home. I was always an independent type; I went and got my own apartment as soon as I could to get away from home. My sister and I were real close and she was in many ways like me, only she couldn’t afford her own place so would often come and stay over at mine since I never stuck my nose in her business. The visits got more and more frequent to the point where she was practically staying at mine more than with mom and dad.

Heading out into the living room, the calendar caught my eye. What surprised me was the date on it, ‘2012’, the sim had pushed me 5 years back to when I was 21 and Hannah 18. My eyes flicked over to the photo of the two of us at the beach next to the calendar, I was carrying her in my arms and we were both grinning like idiots. Seeing it brought back a flood of memories and feelings. Hannah was a bit on the short side at 5’2 but well-proportioned with a toned and lean body that she managed to effortlessly maintain. Back then she always wore her auburn hair in a cute wavy bob cut and seeing it again made me smile. She really hit the genetic lottery and was a total bombshell by 18, something I struggled not to notice. Incredibly, she was actually hotter now than she was back then but there’s definitely something to be said for the appeal of a 18 year old.

Walking to her door, I knocked once and waited for a reply before entering.

Speaking up over her music playing, Hannah says, “Come in.”

I was completely unprepared for what I saw. Opening up the door I saw my 18 year old sister sitting there on her swivel chair wearing nothing but a loose, low cut tee. She had her feet planted on the chair to the sides. One hand was on her mouse and the other was leisurely pumping a small-ish silicon dildo into her teen ass. She wasn’t watching porn, she was just on youtube but that didn’t stop her from masturbating casually. Seeing the sight got me almost instantly hard with how wrong it seemed. Swiveling around to face me, Hannah casually threw out, “Hey James, what’s up?” without breaking pace an instant. Facing me the way she was, it gave me a perfect view of the dildo slowly entering and exiting her asshole. My eyes were completely glued to the sight so couldn’t manage a response. Noticing my attention was elsewhere, Hannah pulls the dildo out and waves it in front of her ass a bit, “James? You OK there? Did you want something?”

Tearing my eyes away from her ass, I manage to stammer out “W-What are you doing?”

Tittering slightly she says, “Isn’t that obvious? I’m masturbating,” before returning the dildo to her ass and resuming the slow sodomy.

“Think you may be using the wrong hole if you’re trying to have fun.”

“Ha-ha. No I’m just trying to get ready for next year, when I’m officially fair game. You think I don’t notice all the guys at school staring at me? Not just the students y’know, my art teacher Mr. Henrik is definitely going to town on me as soon as he can, I can just tell. My poor ass is going to have a rough time and an even worse one if I don’t get ready,” she says with a fake pout.

“Yeah that’s for sure,” I breathe out.

Tilting her head to one side, “…Somethings different with you today, when you came in, you looked at me differently, you’ve never looked at me like that before. You… don’t actually want to use me do you?” Hannah says raising one eyebrow. She still hadn’t stopped sliding the dildo up her ass the whole time; she just kept it up while speaking with me.

“What makes you say that?” I ask.

In response, Hannah starts pumping the dildo into herself a fraction faster and deeper making the bulge in my pants grow just a bit more. “Well, a) You can’t stop staring at my butthole and b) you’re kinda broadcasting it,” she says pointing at my bulge.

Curious, I ask “We’ve never fucked before right?” I ask

“What? No, you always said you thought it was weird so never did anything.” Pausing briefly, I see a flicker of a thought pass across her face. “Wait… Are you saying now that I’m 18 you’re reconsidering?” She says with a slight smirk. “It was my ass that did it wasn’t it? I knew it! You’re always going on about asses and your last girlfriend told me allll about what you’re into. I knew you couldn’t resist this thing” she said giving her ass a playful little slap, making the dildo pop out, fall onto the chair and revealing the tiniest little gape that almost immediately closes. “Tight little 18 year old ass just too much to pass up is it? Can’t blame ya bro, being first is fun and you’re probably not gonna get many opportunities like this, free use minimum age laws aren’t being reduced and I know I’m the only 18 year old you know. Hahaha, oh my God, after all this time, all the ‘no it’s wrong, no we’re family, it’d be weird, I can’t, your my sister’ you’re finally giving in – what made you change your mind huh? Was it all the walking around in those booty shorts? Or the yoga? Or the time I walked out of the shower and you saw? Wait, actually never mind, it’s funner not knowing. Alright, so you want to go at it now or what?”

“Hey! Slow down, what are you even talking about, I haven’t said a thing about using you, I was just… watching was all”

“Yeah, I totally believe you. Please, I can see you practically drooling, you literally can’t resist this ass,” she said punctuating it by grabbing the dildo and pushing it back into her ass.

“I don-“

Hannah presses her legs together and grabs them by back of the knee with one arm and starts sliding the dildo back inside her ass faster and all the way down to the base now. It isn’t easy for her though, she does it with a slight frown. Taking out the dildo, Hannah grabs both cheeks and spreads her ass apart, showing off her tiny gape again, if it could even be called one, saying, “Jesus, just imagine how much fun you could have pounding out that fresh asshole. Hah, like I even have to convince you right, hello, 18 year old anal virgin here, you’re never going to leave me alone now are you?” She said laughing.

The rock hard bulge in my pants quickly put an end to any protests I might have. “Alright you might have a point. Are you sure you’re ready right now? You don’t want to prepare some more?”

“Nah I’m fine, the dildo got me ready enough I think. Honestly the suspense is killing me, just put that dick up my ass already, I’m dying to know what the real thing feels like.”

Taking my cock out of my pants, I make my way over to Hannah, who was still sitting with her legs spread and feet planted to the sides of the chair. She had a look of nervousness and excitement in her eyes I liked. “Got any lube in here?” I ask

“As if I can afford anything right now. You’re the one buttfucking every girl he gets his hands on, why don’t you have any? Actually y’know what? Whatever, just using spit will be more authentic since I kinda doubt many guys are gonna bother lubing up; it’s something I’ll probably have to get use to so better start now. Hannah spits into her cupped fingers and rubs it all over the entrance of her ass and then gives me thumbs up. I crank up the seat so I can fuck her while she’s sitting splayed out like that, with her asshole at just the right height for my cock. Placing the tip of my dick at her puckered hole I lean in a bit, Hannah suddenly retracts back. “Hey! I said spit on it.”

“Sorry, I thought you already took care of that.”

“What do I look like? A pornstar? First time remember, spit on it some more.”

“You’re too cute when you get mad. Alright alright, but only because I like you” I say with a lopsided smile, I try and reach forward to pinch her on her on the cheek but she slaps my hand away.

“Unh uh, no, not happening. I’m putting my foot down here, try and pinch my cheek again mister and I’m not opening up my ass for you for the rest of the year.”

Chuckling, I say “Alright, you’ve made your point, no cheek pinches, just the sodomy then.”

“That’s right. We’ve all got limits James and you know how I hate when you treat me like a kid,” Hannah says with playful anger.

I craned my head forward and spat onto the tip of my dick and rubbed it around her entrance before starting to push inside again. Getting inside Hannah was harder than any of the other women I’d tried so far in the Sim, her asshole just refused to let me in, my dick kept sliding off instead.

It took a dozen tries before I eventually managed to finally get inside her ass. Jesus, it was tighter than anything I’d felt so far, the same kind of unnatural tightness and pleasure I had with Stacey just magnified even more. Lost in complete bliss, I start slowly thrusting in and out of Hannahs asshole, enjoying how it hugged my cock so tightly. That wasn’t the only thing doing it for me though, the knowledge I was buttfucking someone so young and fresh was really getting me off.

With her eyes screwed shut, Hannah manages to groan out, “Alright… So this is what I have to look forward to every day I stay with you then I guess.”

Smirking a bit I say, “Honestly, not quite, there’ll probably be a bit more to expect down the line.”

“Unh, just great. Let me guess, you’re gonna do that stuff you did with your girlfriend to me? Ass to mouth, gaping, creampie eating, public anal and the rest?”

Shyly I reply, “Uh, yeah, I might, but Hannah, you’re my sister, I do care about you, you get to say no if you don’t want to do something.”

“Nah, I don’t wanna form any bad habits. Just try and take it slow if you can, I’d appreciate if you didn’t jump straight to gaping my ass. So… Unh… How’s being first feel?” Hannah asked in between deep whistling breaths out, still with her eyes closed.

“Jesus, you’ve got no idea how good your ass feels.”

“Yeah I bet, 18 year olds will do that to ya. Unh, well enjoy it while you can, I think I’m gonna have to tap out soon.”

Hearing that, I suddenly speed up, thrusting into my sister’s ass faster and deeper than before, eager to cum and coat her guts with my jizz. Noticing Hannah pointedly keeping her hands away from her pussy and on her knees I tell her, “You know you can rub your pussy, it’ll feel good and help.”

“No I need to get use to just the anal first, and besides, I don’t think I’ll always have my hands free to do that, better to get use to this soon as I can.”

I settled into a moderate rhythm, sinking into Hannahs asshole as she sat, legs spread on that chair, perfectly willing to take me in just her ass without complaint. A little bit later Hannah eventually manage to pry open her eyes, slow down her breathing and relax the frown off her face. Craning her head forward she tried to get a better look at my cock disappearing into her asshole.

“You know, I can see the appeal of this. Pussies look prettier empty but assholes look nicer full, I like the way my ass wraps so neatly around your dick, it actually looks really good… Hey grab my phone off the desk would you?”

“Sure,” as soon as I hand it over to Hannah, she unlocks it and starts filming me pummel her ass.

“What are you doing?”

“Like I said, this looks pretty good”

I move to rub her pussy but when I do, Hannah suddenly slaps my hand away. “Hey, knock it off, you’re ruining my shot. Focus on the asshole would you?”

Hearing her tell me to ignore her pussy gets me off more than I can say and I happily oblige and pick up the pace again.

After a little while Hannah asks, “James, could you try doing deeper strokes?”

“What happened to tapping out or pacing ourselves? Han, you could barely handle half strokes before, if I start bottoming out, you’re not going to have a good time.”

“No, probably not, but it’ll look good. Besides, I don’t have to take it for long, I just need a little footage of full strokes. And iunno, the camera helps to distract, it doesn’t hurt as much anymore.”

Alright, if you’re sure.” I start bottoming out in Hannah’s asshole now but with some care to keep my pace moderate at least. I sink down to the base of my cock before pulling it almost all the way out, leaving just the tip in before feeding the rest back into her. Even with the camera distracting her, this isn’t easy on Hannah. She’s groaning hard and wincing a lot so I try my hardest to cum as soon as possible. It doesn’t take long before I feel the familiar pressure in my balls. I grunt out, “I’m gonna cum”

“On my face,” Hannah tells me quickly.

Just as I’m about to explode, I pull out of her ass and depress the seat so Hannah drops down low enough for me to cum all over her face. As I move my cock towards her face, she scoots forward, thrusts the camera into my hands and tells me to film.

As I take the phone into my hands, Hannah takes my cock into hers and starts jerking me off onto her face. I point the phones camera down at her face and record everything. Her hands are slide up and down my cock a little awkwardly but eagerly. She quickly makes me cum and I shoot rope after rope of jizz onto her pretty teenage face. Hannah’s giving me this pleasant, soft smile the whole time I’m coating her face in my cum.

Taking the phone back, she leans back in the chair and extends her arm holding the phone to record herself, making sure to get her cum covered face, tits and sore asshole in the frame. With a bright smile and cum coated face she says, “I’m Hannah Jacobs, I’m 18 years old and that was my first time doing anal with my brother but definitely not the last.”

“Right, not that I’m complaining, but what was all that for?”

“I’m not sure, it just seemed hot was all, might want to post it online one day. Or maybe it could be something to look back on y’know? Especially these days.”

“What do you mean?”

“Well, I’m not going to be 18 forever, sure you can keep buttfucking me when I’m 25, 40 or heck 60 if you want, but it’s just not the same, so better get it while you can.” Hannah says wiggling her ass at me a little and giving me a happy smile.

And just when I thought I couldn’t love Hannah more. “That’s actually a really good point, it is a good idea. Maybe we could even make a habit of it and film every time?”

“No objections here,” Hannah said with a shrug. She stood up and grabbed for some tissues to wipe the cum off her face. I felt a bit disappointed but I knew small steps were better here. With Hannah’s back turned to me, I got an amazing view of her ass for the first time, it was such a cute, perky little thing that I almost couldn’t resist the urge to just grab and cup it in my hands.

“I actually don’t think I’m going to be able to leave you alone this year.”

Turning around and noticing my gaze she replies, “Yup, I figured I was in for a rough one. On the bright side, at least I’ll be good at anal when it’s over.”

I smile at how much of a good sport Hannah’s being. She’s being so cool about it I feel a stab of guilt at how selfish I was being. After a pause I ask, “Han, isn’t it frustrating? I mean don’t you want to cum yourself after that?”

“Yeah I really fucking do actually now that you mention it,” Hannah says with a laugh, “But I can’t cum from anal, so that means my pussy needs attention and you aren’t interested in that so I figure I’ll get off on my own time.”

Again, I feel another stab of guilt, but I think there could be a win-win here, “Well you better learn how to get off on anal as soon as you can, I don’t want you to be blue balled all the time.”

“Wow aren’t you just Mr. Considerate.”

“I try.”

“Well get outta here, unless you want to sit and watch me masturbate properly this time.”

“Alright alright I’m going. Geez, soon as you’re done fucking a girl in the ass she tosses you out, your generation I tell ya.”

Hannah rolls her eyes at me as I leave.

Later on, Hannah comes out of her room, this time wearing shorts and announces to me. “So I’ve been thinking about how to cum from anal and I figure this might work. I’ll just masturbate normally, but right as I’m about to cum I’ll switch holes and try to finish off that way, trick my body or something. I’m hoping if I do it enough times and connect the feelings, boom, a butt slut’s born.”

“Pretty good plan, I’m all for it.”

“Yeah, I figured you might be.”

“Oh actually, I’ve got something to add to it,” I take out one of the remote cocks I have and activate it, handing it over to Hannah, they were a bit bigger than the ones she was using but not by too much. “Try using this instead of your dildo, s’more my size.”

Taking the dildo Hannah shrugged and took it in her hand “Yeah it was about time I got something a bit bigger”. I immediately felt her delicate fingers and soft hand on my disembodied member. She heads back to her room and soon after she goes in I feel my remote cock sink into something warm and tight.

Over the next few days I periodically use Hannah’s asshole, I still take it relatively slow since it’s still early days though. She still never manages to cum or enjoy the anal much but is always peppy about it. One day I check up on Hannah in her room

“So how’s the progress going?”

“No luck, sorry to say, I’m still not an anal whore yet” Hannah says, pressing her lips together and giving me a shrug.

“Has it worked at all so far?”

“No not really, I’m just giving myself massive blue balls at this rate, but I actually figure that’ll actually end up helping in the end.”

“How’s that?”

“Well I think I’ll end up just so horny, my body will just let me cum from anything even if it’s just anal.”

After a solid week of Hannah bringing herself to the edge, then denying herself, getting more and more frustrated with blue balls, I finally hear a scream tear out of her room follow by a loud and very long scream of yes.

I go over to her room to check up on her. Entering I see Hannah laying on her bed, a sheen of sweat covering her body and a small rivulet of girl cum leaking out of her pussy with my remote cock still embedded in her ass down to the balls. She manages to pant out, “Fuck, Jesus Christ James, I finally fucking did it. I honestly thought my vagina was going to explode if I kept that up any longer.”

“You came from anal?”

“Yeah. I think I’m gonna sleep now but I’ll give you a demo later.”

Before I even said anything to acknowledge her, her head had already lolled back and was sound asleep. I step up to her and gently pull my cock out of her ass, this time she actually did gape, it was still small and didn’t stay open for long but it was a beautiful gape.

Just like she said, later that night Hannah came out of her room, wearing her usual outfit of nothing but a tee and holding my remote cock. She sits down to my side on the couch with a big smile on her face, spreads her legs and proudly says, “Watch this.”

The dildo, my cock she was holding was already slick with lube and she slipped it in her ass with noticeable more ease than the first day. I watched her as she pumped her own ass with my cock; eyes still closed but not screwed shut tight this time. She pumped that thing up her ass at a solid pace for 10, then 18 minutes, indirectly getting me off twice. Hannah studiously kept her off hand resting on her stomach and away from her pussy the whole time too. Towards the end, she spent the last minute furiously slamming it in and out before she finally shuddered, legs spasming closed. Breathing hard Hannah takes a minute to gather herself. When she does, she opens her eyes and looks at me brightly. She finally reaches down to her pussy and spreads her soft lips open by parting her fingers into a v. Another rivulet of girl cum leaked out deliciously, a bit more than last time even actually.

“See? I did it. I came from anal. How many 18 year olds do you think can do that huh? Oh you’re going to love this James, I’ll be able to cum all over your dick just from getting assfucked, not even many uni girls can manage that. God I’m so ahead of the curve, I’m like a proper, proper ass whore now,” she says between pants. With a sly look on her face, Hannah asks me “So, do you want to give your new and improved little sister a spin now?”

“Absolutely.”

“Thought so, lean back.”

I lay back down on the couch, shucking off my pants in the process. Hannah clambers up me, grabs my dick and aims it at her own asshole before sitting down on it slowly, she’s watching my face and I’m watching hers as I sink in, I love that she always wears that warm smile when she’s looking at me. “You feel amazing,” I say. Once fully inside, Hannah leans back herself to give me a great view of her pussy and my cock disappearing into her asshole, then she starts bouncing up and down my shaft. I start thrusting up to meet her too, using the couch to spring back up, fucking her faster than I could normally.

Tittering a bit, Hannah says “Look, no hands,” as she rides me with her ass, she’s keeping her hands on her knees. I think she knows how much I’m getting off on her not touching her pussy.

Despite everything, I still don’t really want to take things too far too fast so I just have Hannah continue riding me. After about 10 minutes, Hannah starts spasming again, her legs involuntarily close and she folds in on herself. I like seeing her cum like that, makes me feel like I’m not being selfish. The muscles in her ass tight as well as she’s cumming, taking me over the edge as well. We cum together and I try and pump as much cum into her ass as I can while she’s writhing. I recover before Hannah, when she does, she leans back again, spreads her pussy to show me her cum and says, “Look what you did.” Hannah runs two of her fingers up and down her slit, getting them wet with her own juices before lifting them up toward my face and slipping them into my mouth. It’s a heavy but pleasant taste, I suck on her fingers getting it all before she pulls them back. She repeats the motion but this time brings it up to her own mouth.

“It’s great that I finally get to enjoy this, it’ll be less of a chore now.”

“I was a chore before?”

“Hey, I call it like it is.” Hannah says giving me a peck on the cheek. I give her a sudden, hard thrust in reply, getting a just as sudden gasp from her. She punches me in the chest and gives me a scandalized look. “No surprise anal,” she says sternly, “At least not until later.”

After a pause, I ask “Hey Hannah?”

“Yeah?”

I planned on holding this off until later but she just looked so cute and the cuter a girl was, the more I wanted to see them with my cock in their mouth, especially after anal, I couldn’t help myself. “Do you think you might want to try some ass to mouth now?”

Hannah cast her eyes down and cocked her head. She spent a moment in silence, I almost thought she was trying to figure out a way to gently say no but at the last she looks up at me and says “I knew you were going to ask that sooner or later,” sighing she adds, “ah well, might as well be today.”

“Han, if you don’t to, just say so, really.”

“No it’s fine. Look, it’s weird I know but I just kinda find it gross is all, it’ll take me some time to get used to it is all.”

Hannah pushes herself up, sliding off me, my cock slips out and slaps against my stomach when it leaves her ass. She lies down on her stomach with her face near my cock. Taking it in her hands and just looks at it, lingering for a few moments before she hesitatingly takes it into her mouth as deep as she can, she manages 5 inches with just the last inch poking out of her mouth.

“Ta-daaaa,” she says with a full mouth, then adding “You better not ask me to learn to cum from ass to mouth, because that I can’t do”

Chuckling I ask, “Taste good?”

Still with her mouth full she replies slurringly “Not really, just tastes like dick and cum. You enjoying the view at least?”

“Yup. You’re too fucking cute you know that?” I say with a big dumb smile.

Rolling her eyes she replies, “What’s so great about it? It’d look the same as a regular blowjob.”

“Pretty girl taking a cock after it’s been in her ass? What’s not great about it. But honestly, it’s the thought more than anything. I like seeing you be dirty.”

“Is it the same for every other guy?”

“Not necessarily, but it’d be good manners and a very pleasant surprise if you went and did some ass to mouth as a matter of course without being asked.” Despite how hot this was I had just cum so I was starting to grow soft in Hannah’s mouth, meaning she could speak more clearly now.

“So you’re trying to tell me cocks belong in my mouth after they’ve been in my ass? Huh, James it kinda sounds like you’re trying to train me to be a slut.” She said with a playful look.

“Mmmmm, more like my personalized slut.” I corrected

“Welp, that’s what little sisters for,” she says shrugging. “You know you’re pretty lucky James, if it weren’t for me, you’d probably never get a chance to try out 18 year old ass, now you’ve got a live in teen that cums from anal and is letting you do whatever, you better appreciate how lucky you are pal.”

“I do Han, I absolutely do, you mean everything to me. God it’s such a shame I’ll only get a few years with you like this”

“Chin up, no one beats time. And who knows, maybe there could be others. Say, if I have a daughter, I’ll try put in a good word for you.” My cock twitched in response despite how empty my balls were at hearing that.

“Wait, what does that mean?”

“I just mean this might not be your only shot at a 18 year olds ass. If I have a daughter, it could happen again.”

“I don’t even know what to say. You’re just the best.” I knew it was a bad idea, but I couldn’t help it, I just had to do it. As Hannah was laying there with my cock filling her mouth after it’d been up her ass, looking at me with her pretty brown doe eyes, I reached down and pinched her cheek.

Her eyes immediately narrow at me, “You know, it’s a really bad idea to piss off a girl when you’ve got your junk in her mouth right? Accidents happen James, accidents happen.” Hannah says, punctuating with a nibble

Later once we both got cleaned up and dressed I said, “Hannah, you should keep practicing with the dildo, I kinda want to be a bit rougher with you next time but I don’t really want to end up hurting you.”

“What? No, that’s a terrible idea. Again, I’m only going to be 18 once, and with the way I think you’re going, I’m pretty sure by the end of the month I’ll be able to take you without batting an eye. This is literally the only time I’ll have trouble taking it; I think you should try enjoying that while it’s still the case.”

Confused but immensely turned on I state, “But it’ll hurt.”

Shrugging, Hannah says, “Not your problem, let me worry about that, you just worry about getting as much mileage out of this asshole as you can.”

“Have I told you how much I love you?”

“It could do with repeating,” Hannah says giving me another of her bright smiles

Smiling back I say, “I’ll keep that in mind. I’ve got to head out now so house is yours for a bit, I’ll see you in a few days yeah? So, don’t do any practicing while I’m gone then.”

Hannah gives me a nod, “Nothing goes in this ass but your cock, got it.”