tagAnalThe Sim - Custom Scenarios Pt. 04

The Sim - Custom Scenarios Pt. 04


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


"So Simone, I was thinking this time around you could put me in a story with a tomboy, I've always had a thing for them."

Simone instantly responds as usual, "Tomboy huh? We can do that easy, the personality archetype is actually pretty similar to some assets you've come across already. But now I've definitely got more than enough data on you to know your preferences, I can come up with a more holistic encounter now."

"That's good?"

"Yes James, it's good. You happy to go with the same kind of information injection I did last time?"

Simone had undone the information injection from before, which meant the belief was gone but I could still remember Hannah and my life with her. I still vividly recalled completely believing that she was real, It was quite the shock when I came out of the story and Simone gave me back my real memories.

The data dumps had since become the ultimate tool for roleplay; they were a more immersive and sensational way to experience fantasies. You didn't need to pretend to a certain someone or doing a certain something, because the Sim could convince you completely that everything you experienced was real.

"Yeah I am, but could you go a step further than last time? Make me forget that it's all inside the Sim, just make me believe I'm really me and I'm really with a tomboy-ish friend."

"In the real world or the Free Use world?" Simone asked.

"Uhh, something in the middle? I don't want real world behavior since I like how crazy things get in here, so try and straddle the line yeah? Other than that, just cook up whatever you think I'll like."

"Well James, I can manage that but you're going to have to sign some more waivers if you want to mess with your head that much."


"Alright James, compiling and data dumping now, stand by."

I barely recognize the transition.


"What's up?" Alexa asked.

"Uh, nothing, I just sorta zoned out for a moment there Alex."

I still called her Alexa in my head since that's what I called her when we were younger, but ever since growing up she'd preferred to go by Alex. We'd been friends since we were little kids, I remember one of the reasons I liked her so much when we were little was because she was just like one of my guy friends, only pretty to look at. I'd never admit to something so shallow these days, but it was definitely was still a bit true.

We were hanging out at her place, just having a few drinks and playing some mindless shooter. She was complaining again about how tuition, rent, and all the unexpected expenses that keep cropping up were killing our holiday plans. We've been planning to go backpacking across Europe together during the summer break for the longest time but never actually manage to put enough money together for it.

I'd vented to her the same way before, usually after something expensive and unexpected happened. This time, it was just her turn; her car had broken down on her and our trip would be pushed back again. I just listened and watched as she swore and vented her frustrations out on the enemy team, it was always funny seeing her get mad since she so rarely did.

You'd think after being friends with her for so long, I'd have gotten used to how pretty she was, but I wasn't, it still always got me when I really looked at her. Alex was one of those girls you'd need to do a double take on since she rarely dressed up or wore makeup; she came off as sorta plain from a distance but really wasn't if you looked closer. Even without flattering clothes, makeup or even trying, she was gorgeous and would be even more stunning if she ever cared about that sort of thing. She wasn't unfit though, she surfed pretty frequently so had a toned and tight body, she just didn't care all that much about playing up her looks.

The surfing and salt water left her hair looking like a wavy mess most of the time, but it still managed to look good to me; I always did like her short black hair, even if it made her look a bit like a boy from behind.

Alex snaps me out my thoughts saying, "Fuck me James, at this rate we're never gonna get to see Europe, we keep pushing the trip back year after year and never make any headway on the savings. It's fucked."

"There's no helping it really, it's not like we're gonna get paid much more before we finish our degrees and we can't cut any more corners anywhere else."

"I know! It's fucked!" Alex huffs out. After a pause, she says half seriously, "Do you think you could start selling drugs? I hear drug dealers make a lot of money."

"They also get arrested a lot and have their lives ruined. No I don't think I can. Do you think you could start doing porn?" I say, expecting her to either punch me or agree but only if it involves pegging me, instead Alex goes silent and seems to just think about it.

I try not to let it get to me though since I expect she's just fucking with me. But after a while she eventually says, "I know those camgirls do make quite a bit. Maybe we could actually try that?"

OK, I know she's going for the long con but try as I might, I still can't help but get a little excited at the notion. I try and reposition myself so she won't notice the growing chub in my pants.

Mistaking my silence for disagreement she continues, "What are you seriously gonna turn down the chance for free pussy? I know we've never done anything before but fuck, why not right? It's not like either of us is in a relationship, we get along, I have a vagina, it's a good idea James."

I try and fail to play it cool, "No complaints here. I'm up for it."

"Cool, alright... Shit, didn't think things through this far. Probably can't just get into it right now, gotta plan stuff, get a proper recording setup and whatever." Alex pauses to mull over things and says, "We'll do one video and see if that works, if it doesn't get any traction we can call it quits."

I keep a lid on my slight disappointment that I'd have to deal with the logistics rather than having fun, I helpfully add, "Have you considered those camgirls only make as much as they do because they've got an audience? We can't just film something and put it up. We'll need to build a fanbase first, so maybe we could put up a bunch of free videos online?"

Alex eyes me suspiciously, "Uh huh. That kinda sounds like an excuse to just fuck me a whole bunch."

"I can't say that isn't one of the highlights of the plan. But seriously, you can't just film one thing or cam once and expect much of a response."

Thinking it over, Alex concedes, "Yeah, yeah, alright. We should probably think of some way to stick out from the crowd too y'know. Have some kind of niche kink yeah?"

"That'd help. And don't worry about the camera stuff, I've got that covered already. Where do you want to film it though?"

"Just here? It's not like anyone cares about the setting. Come over tomorrow and we'll do something alright."

Grinning like an idiot I reply, "Cool."


The next day I arrive at Alex's carrying the camera equipment. She throws open the door for me and heads back inside, not bothering to help me carry the stuff inside. I don't mind since she's wearing a pair of snug jeans and I get to watch her ass sway as she walks away. Alex sits down on the couch and goes back to doing whatever she was on her laptop. She's wearing a loose singlet without a bra, again. It was an outfit she often wore around me that tore me; on one hand, it meant I got to enjoy an eyeful once every while and she looked fantastic in it, on the other hand it blueballed me to no end, something Alex was blissfully unaware of, she just didn't consider that sort of thing with me.

Alex talks to me from couch, "So I was doing a bit of research yesterday about how to stick out and had some ideas. I saw anal videos tend to be a bit more popular and make a fair bit more than non-anal ones, I thought that could be our thing; we'd mostly do anal and I'd be like this chick who really fucking loves it in the ass and can't get enough of it. What do you think dude?"

My cock immediately springs to life when she tells me her idea and I almost break my neck nodding in agreement, but I still manage to give her a proper reply, "I mean, you know I already love it, I've told you enough times how much I loved doing Shelly in the ass but it's kinda unoriginal? Like, every pornstar there is pretends to scream about how much they love it in the ass and shit right? It's nothing new is all."

Alex pulls a face, "Wow, I can't believe you're saying I shouldn't act like an anal slut. Well then, do you have any ideas?"

"Actually, I do. I thought we could do like a super casual, friends with benefits sorta thing. You'd play it up and be all like 'hey man, what's up, want some of my ass?' then be all bored or apathetic or carry on with something else while I'm doing my thing." Realizing she might think I didn't want to do her anal idea at all I hastily add, "Oh but we definitely keep the anal part, we should definitely do lots and lots of anal."

"Oh that's part you like." Alex then pulls a confused face, "But the bored part? Where's the fun in that?"

Struggling to explain, "It's hard to explain, just trust me it's hot, I'm the one with the dick here."

Shrugging, Alex says sarcastically, "Alright master of male psychology. Well give your idea a go, but if no one gives a fuck because I'm a dead fish the whole time we're going down the tried and true anal slut route alright."

"I'm 100% alright with that." Alex rolls her eyes in response.

"Alright so since it's all casual, no rehearsals, we just set up and start filming now, cool?"

"Yeah, sounds like a plan. I guess I'll just start playing some Overwatch then."

I give her a look. Alex says, "What, you said I should do something else."

"No, you should, it's a good idea, just didn't expect you to go along with the program so fast."

Alex suddenly turns back to me, "Oh by the way, do you need any help getting it up?"

"I think I'm good on that front, but it wouldn't hurt."

Alex reaches up to bunch her singlet up in the middle, showing me both her perfect, pale white tits. My heartrate goes up another notch at the sight. "Yup, that definitely helped."

"Well, no excuses then, let's do this before I pussy out."

With one stationary camera, one hand held and one awkwardly strapped to my head, I had all the angles covered. Switching them on, I jump right in and ask Alex, "So, I can go straight to the ass then?"

Without taking her eyes off the TV, Alex simply replies, "Go for it dude, it's all yours."

I've near instantly got a raging hard on as soon as I hear her say that, I couldn't have hoped for better. I had to give it to Alex, she really knew how to play the part. Alex gets off the couch and lays flat on the floor before starting up Overwatch on the console. I go to straddle her back and pull down the jeans she's wearing to show off her perky little butt.

I pry apart her cheeks and get my first proper look at her ass, mumbling to myself, "Fuck that's hot."

Alex overhears me and says, "It'll look hotter once there's something in it."

Grabbing the some lube, I drip a small amount onto her back door and rub it in with the head of my cock. Eventually satisfied with how slick she was, I take aim and start pressing in, making Alex visibly tense up. With a bit of difficulty, I manage to slip the head of my cock past the tight ring of muscle of her asshole, eliciting a grunt and some swearing from Alex. Confused at the trouble she's having I stop. Given that she wanted to do mostly anal videos, I figured she'd have experience.

Alex had other ideas because when she noticed I stopped, she said, "Just keep going man."

Well, I couldn't argue with that. I sink an inch in, then another 2, I keep feeding her ass more of my cock until I've pressed firmly against her cheeks with almost all my cock inside her, her ass is keeping me from bottoming out but I'm happy where I am. Alex finally says something once she feels I'm all in, "Shit, that's it?" Then realizing what she was saying adds, "Haha, sorry, I didn't mean you're small, it's just that isn't too bad I guess. Fuck, I was watching all these first time anal videos with girls screaming and thought it'd be way worse, it just stings a bit is all, I can take it pretty easy."

"Wait, what? Have you never even done anal before?"

"Nah not really."

Bewildered, I ask, "Then why'd you agree to this?"

Alex casually says, "Because you wanted my ass? And I mean how hard could it be?"

I don't know if she's playing it up for the camera or being honest, and I don't care at this point. I can't help but start pumping into her now. The fact Alex is just letting me play with her asshole any way I want turns me on more and more until I'm desperate to pound into it with everything I've got, but I'm still conscious of how new to this she is so I ask, "Alex, do you think you're OK with being fucked harder now?"

"Why are you asking me? If you want to fuck it, fuck it, if you want to fuck it hard, fuck it hard geez."

Christ it was like she knew exactly what to say to set me off, I immediately start pounding into her ass within seconds after that little prompt. Alex is grunting at the treatment but little else, it's not even stopping her from doing pretty well in Overwatch.

Minutes of me bottoming out in her asshole go by before Alex eventually says, "Guess you've really got a thing for ass?"

"What gave it away?"

Laughing lightly Alex says, "Yeah, well, have fun in mine then man, it's all yours."

I pull apart her ass cheeks to get a better view of my cock slowly sliding in and out of her butthole. Alex wasn't kidding about not having done anal before, she's deliciously tight and snugly hugging every inch of my cock, she feels better than anything I've ever felt before. It's hypnotic watching her ass swallow my cock again and again, if I could, I'd do this all day.

A few minutes of slowly assfucking her go by before I eventually ramp up my pace and start pumping into her faster and harder while she ignores me and plays, I get some real good footage of that. Still, her ass is keeping me from fully bottoming out in her, but I'm hardly gonna complain about that.

A little while later, Alex thrusts her ass back into my cock, then keeps pushing back until she's on her knees with her ass stuck out. Almost like she was reading my mind, she says, "You can put the whole thing in this way."

I confirm, "The whole thing?"

"Yeah, I noticed half strokes look terrible and we'll make more if I can take it deep."

"Alex I think I love you."

Alex turns around to pull a face at me, saying, "Don't tell me you fall for every girl that lets you buttfuck her. Don't make this weird man."

"Haha, sorry. I'll try and strictly assfuck you platonically."

"You better."

As if inviting me to get on with it, Alex crosses her legs to make her ass look even better. This way, I can get a perfect shot of my cock entering her ass with nothing to block it. I slowly feed the last few inches into her, savoring the satisfaction of being completely inside her, until my balls are resting against her pussy and all 7 inches of my cock are deep inside her. I didn't mean to but I end up sighing and shivering when I bottom out.

Alex says, "Did you just-" then stops to briefly giggle, "Aww, you are in love, breathlessly, hopelessly in love." Alex turns to looks at me and strikes a dramatic pose with her wrist to her forehead, saying mockingly, "But alas, I can't return your feelings gentle Sir."

Yup, that's what I deserve. I can only manage a weak, "Shut up," punctuating it with a sudden thrust.

Alex tenses up but still manages to mock me, "Take it easy now, wouldn't want you to faint."

She's not gonna let that one go, whatever, I console myself by sodomizing her slowly.

I quickly forget everything and only care about taking her ass. Using my thumbs I pry open her rear end to get a better view. The sight of my shaft slowly disappearing into that perfect, little hole sends waves of delight through me. She just looks so fucking hot taking it up the ass like this, letting me play with her asshole like a toy while she hardly cares; it's all I can do to keep from cumming early.

More minutes go by of me pulling out entirely and then slowly feeding my cock back in before Alex finally interrupts my reverie saying, "If you want, you can go harder dude. It doesn't sting much anymore so I think I can take it."

My cock jumps inside her ass but I still try to be polite about things, "What? Are you sure you wanna jump into the deep end like that? Those first time girls us-"

"Those girls are just being pussies, jam it up my ass if you want dude, it's what I'm here for."

And here I thought my cock couldn't get any harder. I take Alex's word, happy to hear her tell me I didn't have to be gentle. I switch from slowly enjoying her ass to quickly pounding into her hard. The sudden change to blasting her asshole isn't kind on Alex and she grinds out a long winded 'fuuuuuuuuuuuck', I slow down but don't stop bouncing into her ass.

Alex groans out, "OK spoke too soon. Shit that stings."

"Want me to go back to what I was doing?"

Despite her white knuckle grip on her controller, she's quick to turn down the offer, saying, "Nah man, go wild, guys love this shit, pound it out, I can take it dude."

Getting a chance to assfuck Alex like this is a guilty dream come true and I start really going to town on her ass, my earlier concern quickly evaporating. I'm pulling my whole cock out and slamming it back in as rapidly as I can. The hellish treatment for her feels incredible to me; bottoming out in her ass again and again, never giving it any rest or the chance to close properly before I plow back in being the best part and seemingly the roughest for her.

In between grunts and groans Alex says, "Shit man, you really love that thing don't ya."

I can't manage a reply and just continue slamming into her, taking her ass for all it was worth, not even caring if the rough treatment was giving her second thoughts about the whole arrangement. Alex's ass was just the most incredible thing, no matter how many times I'd plunge into her and pull out, her asshole would still tightly grip my cock and warmly squeeze my whole length.

I soon feel a familiar pressure building in my balls. It's like a switch turns on in my head, making me snake my hands under her hanging singlet and grab hold of both Alex's tits, squeezing and mauling them with sudden violence while rutting her ass rabidly. Alex doesn't have the biggest tits, maybe C cups, but they're the perfect size to grab a handful of. I'm suddenly glad that she's so fond of wearing these loose singlets without a bra.

Incredibly Alex keeps still throughout and doesn't try to run away, she just leaves her ass where it is, letting me ravage her asshole. A minute of the abuse goes by before I slam in finally and pour my nut into her ass, practically filling it with jizz. It's not until I come down until I realize how rough I was being and suddenly panic that Alex will want to call the whole thing off. Figuring this may be my last chance, I decided to push my luck while the cameras were still rolling and she was still in character. I ask Alex, "Can I fuck your mouth for a bit?"

To my surprise and delight, Alex just mumbles out, "Yeah man, go for it."

I pull out of her ass, making sure to spread her open wide as I do and getting a good shot of my cock plopping out followed by a thick stream of cum. Watching my cum leak out of her ass, I get an idea. I place my cock under her ass so the cum drizzles onto it, I felt mean for giving Alex an unexpectedly obscene extra snack but with the cameras still rolling, I kept trying my luck.

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