The Sim - Custom Scenarios Pt. 03

Disclaimer: This story is, as always, set in a simulated virtual reality and heavily anal focused. This chapter involves incest with a younger sister. If that's not your thing, you should probably skip this. This is all pure fantasy; don't expect realism or normal behavior.

~~~

"So, what were you thinking of this time James?"

"I uh, was kinda thinking of incest this time around."

Simone put on an exaggerated shocked voice, "Wow, incest? Oooookay, I guess can do that."

I'd gotten used to Simone ribbing me by now so just ignored her teasing and continued, "Only problem is, I don't actually have a sister."

"There's always your mum," Simone helpfully chimed.

I made a face and shook my head. The idea of incest appealed to me, but only in a fictional sort of way, I figured this would be the perfect place to indulge in that fantasy. I said to Simone, "I was thinking, you're already messing about in my head right? Giving me new senses, heightening existing ones, changing how I see things and God knows what else. I was wondering just how much you could do."

"Well, without getting too technical, let's just say the interface is very extensive."

"Well, do you think you could make me believe something?"

Seeing where my train of thought was going, Simone replied, "Like convincing you, you had a sister, giving you a memories and a backstory of her?"

"Yeah, that's just what I was thinking, but don't do anything permanent, undo things after alright?"

Simone hummed, "You're going to have to sign a lot of waivers but that's definitely doable James."

~~~

"Alright, now with that all out of the way, what sort of wincest fantasy did you have in mind?" Simone asked cheekily.

I only had a rough idea of what I wanted, I banked on Simone filling in the missing bits with something fun, "Could you put me back at home, living with my younger 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."

"Hmmm, so something like origins of a butt slut?" Simone replied.

Chuckling, "Yeah, something like that, I'll leave the specifics up to you though."

"I think I've got just the thing, compiling now."

~~~

The familiar sensation of my vision waxing and waning hits me again. By the time it was over I find myself in my old apartment, a wave of nostalgia instantly hitting me. It was sorta frightening how accurate the place was, like they modeled it after the real thing. Hearing music coming from the guest room that Hannah had essentially taken for herself, I figured she was here.

Hannah had always wanted to get her own place too but she was still in high school and no job she could find would pay enough to manage it. So she did the next best thing, she constantly came over to stay at mine.

Hannah had the same need to get away from home as I did, and since I never stuck my nose in her business or pried, staying at mine was almost like having her own place. She was over so frequently she might as well have been my roommate. I didn't mind at all though, Hannah and I were always incredibly close and having her around was more than just a little nice.

Heading into the living room, the calendar catches my eye, it's the date on it that surprises me, it reads 2013. I know it shouldn't surprise me, I did ask for Simone to put me back to when Han first started learning to live with Free Use after all, and since she's 23 now, turning back the clock was necessary; It's still a shock to find yourself 5 years in the past.

My eyes get drawn to the photo of the two of us at the beach pinned next to the calendar, I'm carrying Hannah in my arms and we were both grinning like idiots, seeing it brought back a flood of memories and feelings from that day. 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, or now rather, she always wore her auburn hair in a cute wavy bob cut and seeing it again made me smile. She really had hit the genetic lottery, she had grown into an absolute bombshell but even now when she was only 18, she was still gorgeously stunning, something I struggled not to notice. Some guys might think younger is better but I actually thought she looked even hotter outside the Sim than she was in here. But, there's definitely something to be said for the appeal of an 18 year old.

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

Speaking up over her music playing, Hannah yells out, "Come in."

I was completely unprepared for what I saw. Opening up the door I saw Hannah 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 tiny asshole. My eyes were completely glued to the sight, I couldn't even manage a response. Noticing my attention was elsewhere, Hannah pulls the dildo out and uses it to wave at me 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 she returns the dildo to her ass and resumes the slow sodomy.

"Think you may be using the wrong hole if you're trying to have fun."

Hannah deadpans, "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." Hannah puts on a fake pout and adds, "My poor ass is going to have a rough time and an even worse one if I don't get ready."

"Yeah that's for sure," I breathe out.

Tilting her head to one side, Hannah slowly lets out, "...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 keeps 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?"

"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.

She asks with a growing smirk on her face, "Waaait... Are you saying now that I'm 18 you're reconsidering?"

I don't reply but Han carries on like I just confessed. "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.

Hannah doesn't stop; she seems incredibly cheery over finally breaking down my reluctance. She talks quickly and excitedly, "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. I mean, you know how fast the new 18 year olds each year get snapped up for use. 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, you're 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 funnier not knowing." Finally finished her little victory rant, she takes a breath, gives me a self-satisfied smile and asks, "So, you want to go at it now or what?"

"Hey! You know I haven't even said a thing about using you, I was just... watching was all."

Hannah deadpans again, "Yes, 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 hugs her knees to her chest with one arm, it makes her legs dangly adorably. Using the other she 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's still new to anal so 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 and teases me saying, "Jesus, just imagine how much fun you could have pounding out that fresh asshole. Heh, 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. She got ready by leaning back into her chair and planting her feet on the armrests this time. Han really wasn't thinking twice about letting me have her ass, she was just completely opening up for me. Once I was right in front of her, she stared up at me with a look nervousness and excitement I liked, it'd been so long since I'd seen that look. These days, whenever Hannah came over, she would take it up the ass without so much as talking to me sometimes.

"Got any lube in here?" I ask.

"Hey, you're the one buttfucking every girl he gets his hands on, why don't you have any? ...Actually you 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 used 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 the thumbs up.

I crank up the seat height, bringing her ass up to the same level as my cock, making it incredibly easy to pound into her while she's sitting splayed out like that. Placing the tip of my dick against her little, virgin 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. And Jesus was it something else, 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 Hannah's asshole, enjoying how it hugged every inch of me so tightly, indulging in the feeling of her anal walls sliding smoothly up and down against my shaft. The raw sensations weren't the only thing doing it for me though, the knowledge I was buttfucking my sister, 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 used to just the anal first, and besides, I don't think I'll always have my hands free to do that, better to get used to this soon as I can."

I settled into a moderate rhythm, sinking into Hannah's 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 kinda see the appeal of this. Pussies look prettier empty but assholes look nicer full. I sorta 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," she says with a shrug.

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, "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 want a little footage of full strokes. And iunno, the camera helps to distract, it doesn't hurt as much anymore," Hannah said.

"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 petite hands 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 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 a teen 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."