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.
After a little prodding and pulling, I think I manage to get the majority of the creampie to land on my cock. I carefully make my way round to Alex's face and present her my messy cock, curious to see her reaction. She doesn't look at me or my dick, just keeps her eyes glued to the screen and game going on but does open her mouth invitingly. I don't think I've ever seen her look more beautiful, it was incredible how good she could look without any makeup or trying.

I slip my cum covered cock into her waiting mouth and down her throat until she gags, I don't want her hacking up cum everywhere so that's where I stop. I got a happy surprise when Alex actually started swirling her tongue around my head and shaft despite the fact it had just been up her ass. It was even better when she wrapped her lips around my cock and sucked off the entire thing, collecting all the cum in her mouth. Making eye contact with me and the camera for the first time, she asks with a slurred voice, "Do you want me to swallow this?"

Grinning cruelly I say, "Yeah."

Alex simply says, "Gross," but swallows the load loudly all the same.

Alex makes a face at the taste, "Dude I can't believe you just made me eat the cum from my ass. What happened to starting off slow. First time I get assfucked, ever, and you make me eat an anal creampie. Ever heard of jumping the shark? How are we supposed to top this? Or am I just supposed to eat the cum from my asshole every time now?"

"Well I mean, that's not a terrible idea. It could be your thing, 'girl that eats anal creampies' or maybe we could bring in another girl and you could eat it out of her."

Alex rolls her eyes at me and says, "You are really milking this for all it's worth aren't you." Alex reaches for a glass on a nearby coffee table, takes a drink and swishes it around her mouth to wash out the taste.

She mutters to herself, "Guess I should try getting used to that taste probably." Then addressing me she says, "You done man or do you wanna keep playing with my asshole some more?"

Alex knew exactly what to say to get me going, but I still needed more time than that to recharge so I told her, "Yeah I am, your gonna have to wait till later for more."

Alex sarcastically replies, "Oh great, I can't wait. Alright, see ya later man."

I start switching off the cameras, and when the last one gets turned off. Alex suddenly leaps up onto her feet and punches me hard in the chest. She angrily says, "You fucking asshole. Ass to mouth? Making me eat the cum from my ass? You fucking kidding me? We never talked about any of that."

I start making excuses, "I'm sorry, I'm sorry, I got caught up in the moment. And fuck, just because I was filming didn't mean you couldn't just call it quits, it's not like we were live, I thought you were OK with it."

Alex punches me hard again, "You seriously going to blame me? I was acting, dickhead! I've never been fucked in the ass before and you think it's OK to just put it in my mouth? God, you are such an asshole."

Regret was finally starting to hit me, I try to apologize some more, "Sorry. You want to call the whole thing off then? We can just put that one up for sale then, and you're getting anything we make obviously."

Alex still looks pissed and considers it in silence for a few moments before saying, "Maybe. Iunno. I think I wanna put it up for free and paid as well, I mean some cheap dickheads gonna buy it and it's just gonna end up everywhere anyway, might as well do it myself and get some credit for that. But if it ends up getting fuck all traction, then yeah James, I am gonna call it quits."

Disappointment hits me like a brick but I know it's my own fault so I just agree.

Alex grabs some nearby wet wipes to start cleaning herself up while I dress. When she's cleaning her ass, she sucks air in between her teeth and says, "Fuck, that hurt."

"I thought you said you could take it?"

Funnily enough, Alex almost seems offended at this, "And I did, didn't I? I was fine up until you started going ham. That is not how you're supposed to assfuck a virgin dickhead."

"It looked great though, it was really good footage."

"Oh yeah, that's totally why you did it, to get class cinematography. You know, you're lucky I'm not a pussy, otherwise I'd have torn your dick off."

I started to relax now that things started going back to normal between the two of us. I tell Alex, "You were amazing by the way."

"Oh I'm sure I was," she said sarcastically.

"No, I honestly mean it. You couldn't have said anything hotter if you tried. It's like you reached into my head and found everything that turned me on. Trust me when I say that's gonna play well. Fuck, I'm getting a bit of a chub just thinking about what you said right now."

Alex raises a brow, "That good huh?"

"Yes, that good. How'd you know to say stuff like that?"

She shrugs, "You said it was supposed to be a casual, friends with benefits thing fantasy, I just acted like that."

"Well it was perfect, you were perfect."

"Yeah, yeah, keep it in your pants."

Once we're dressed, I transfer the footage onto Alex's laptop and let her watch it, while it's playing, I ask her, "So what do you wanna title it?"

"Huh?"

"The video, gotta have a catchy title right?"

"Oh yeah right. Huh, I hadn't really thought about that. What about, like, teen anal slut?"

I cringe a bit, "Bit unoriginal don't you think? Maybe we should try get it to stand out more."

"What are you, some avante garde director of porn? No one cares about that shit James."

"Come on, humor me."

Alex sighs and relents, "Fine, what do you want to title it then?"

I mull it over before saying, "How about, 'Tomboy friends with benefits lets me fuck her ass any time I want'?"

"Oh and that's supposed to be better? That's a mouthful and a half."

I gesture at my dick with both hands.

Alex groans, "Fine, fine. I don't even care, if it doesn't do well it just means get to keep my asshole safe and sound."

We upload the whole thing as is with only absolutely minimal editing.

~~~

I hang around at Alex's place, constantly refreshing the pages to see where we're at. In less than a day, it's got tens of thousands of views and a few hundred dollars in purchases.

Alex says to me, "Alright fine, it's doing well. Guess we better do some more then."

"What? Now? That soon?"

"I was planning on maybe one a week or something, but it's just I had an idea." Alex doesn't continue and just goes silent, she looks nervous and hesitant to go on but she eventually manages to spit out, "I can't fucking believe I'm the one suggesting this... Alright so I was looking around and saw painal videos seems like a really niche thing that a few creeps really like. I thought we could do a one off painal video. Emphasis on the one off."

The surprise is evident on my face and I only manage to mutter incoherently.

Alex says, "Yeah I know. But my ass was still sore and the idea just hit me. Wanna do it or not?"

"Y-Yeah I'm game."

Alex cocks her head, "Y'know, I was kinda hoping you'd say no. Guess you don't like me much."

That hurt, I sag suddenly and say, "No I do, we shouldn't. It really isn't worth it. We can make enough as is, no need to get all deviant fetish-y."

Seeing the sudden change in my demeanor, Alex quickly says, "Wow, wow, I was just fucking with you. It's my bloody idea and I do wanna go through with it."

"Well too bad, I don't anymore."

Alex seems primed to argue but softens instead, saying, "Look, I know you do like me OK? I was just joking, Jesus. Come on, it'll be fun."

"Not for you."

"True, but I'm a big girl. I didn't mean it OK, we're cool, I'm not angry at you."

I'm still unconvinced, so Alex pulls down her sweats and spreads her ass in my direction, saying, "Come on, you know you wanna tear that ass up. Think about how much fun it'd be to pin me down and ram it up my tight ass."

Again with the dirty talk. I still wanted to say no, to prove I wasn't an awful guy but the raging hard on in my pants made plainly shot that down. So I just give in. Getting together the camera equipment again, we set up a safe word and prepare for a scene on the couch.

Alex takes her pants off this time and is on her side, hugging her knees to her chest, with her head lying on the arm of the couch. She looks at the camera and says, "Well this is Round 2. My asshole is still sore as shit but James wants to buttfuck me again so I guess we're doing this."

I lube her up, take aim and start pressing in. As soon as the head of my cock touches her brown star, she sucks air in through her teeth, saying, "Fuck, this is gonna hurt."

I ignore her and keep pushing in, battering my way past the resistance and slipping into her tender, battered asshole, eliciting a gasp. I slowly sink down to the balls again and start pumping her at a moderate pace. Alex is focusing on her breathing, taking careful, steady breathes in and out to help with tolerating the pain.

Between breaths, Alex says, "This better fucking be worth it, you better be having the time of your life breaking my ass."

"I am, you're too good to me, I don't deserve this."

I start speeding up again. Alex's eyes are screwed shut and she's burying her face in her knees while I'm pumping her ass with deep strokes again. The constant battering is starting to give her the smallest gape when I pull out to get a shot. It looks so good I want to see if I can make it wider, but I clear it with Alex first, "Alex, you're asshole is starting to gape a bit. It looks really, really good, think I can try opening it up wider?"

Alex replies curtly, "Is it gonna make you cum sooner?"

"Yeah I think it will."

"Then fine. OK. If you wanna gape it man, go ahead." Then adding in very unconvincingly for the camera, "I love getting my ass gaped anyway."

I start pulling my cock entirely out before plunging back in suddenly again and again. Each time I use my hands to spread her ass open whenever I pull out. It takes a toll on Alex but it gets the job done, her pretty pink little hole starts to yawn open almost as wide as my cock and stay that way. With my thumbs on the rim of her asshole, I spread it wide as I can as I slowly pull out, admiring the sight of her stretched out hole. When it starts to wink shut, I repeat myself, never letting her fully close. The contrast between that pink, wide open hole and her puffy, juicy, tight looking pussy was erotic in the extreme. I was taken with the idea her asshole was made for fucking and her pussy just a decoration.

I'm so focused on fucking out her asshole, I didn't hear the soft sobbing coming from Alex. With her head buried in her knees, I couldn't see either. But when Alex finally looks at me, I see her face is streaked with some tears which she's fighting to hold back. Alex stares at me with pleading eyes and asks, "Hey James, how often do you think you wanna do this?" then in a desperate tone, she adds, "Is it gonna be every day?"

I keep in mind what she said and reply, "No, I think just once is enough Alex."

She nods once acceptingly and buries her head back in her knees.

That was enough niceness though so I spend the next minutes roughly pounding out Alex's asshole until it was a swollen red mess. She was gaping like a pornstar by the end of it to my satisfaction and would hardly close, I liked seeing what I was responsible for doing to her.

When I cum, I slam inside finally and fill her up again. It's a repeat of the first video, I pull my cock out of her mistreated ass, a thick trail of cum following before I treat her mouth to another round of fucking. At least this time there's little cum on my cock though. Alex almost seems relieved to suck my cock, even if it's just been in her ass, anything's better must be better than being assfucked at this point for her.

While she's busy cleaning me off, I tell her "There's some cum leaking out of your ass, don't let it mess up the couch, eat it up would you?"

Without taking me out of her mouth, she reaches back with her free hand and starts scooping up the cum trailing down her ass, the stationary camera perfectly catching it all. She pulls me out of her mouth, sucks the cum off her fingers and then returns me to her mouth. She does this like a half dozen times before her ass is clean. I'm not done with her yet though and say, "Inside too."

Alex gives me and the camera a tired look before complying. She tries to reach inside her ass but tenses and winces when her fingers brush against her abused hole. It takes her a moment to psyche herself up, but she soldiers through and plunges 3 fingers into her ass to scoop out the cum inside, pain clearly etched across her face as she does.

She quickly and robotically repeats this a few more times until she's satisfied she's cleaned out as she can manage.

"Thanks Alex."

"Any time James, see ya."

I turn off the cameras again. And as I expected, Alex breaks character again, the tears and pained expression on her face instantly cutting off.

"Man I was so hoping you were faking that."

"It wasn't hard to. That really sucked. I'm not gonna sit right for a week after that."

Defensively I say, "Remember it was your idea, you can't be mad at me."

"Yeah, yeah, I know. Jesus Christ I've had a day; started out an anal virgin, ended it having eaten cum out of my ass twice then having my asshole gaped open. You are really using this to turn me into a slut."

I point a finger at her accusingly, "This was all your idea, all of it, I'm innocent I tell you."

Alex groans, "That doesn't mean you have to be so... enthusiastic about things. Jesus, I'm not a pornstar remember."

"Well, you can relax, we definitely aren't doing another one until a week or mores gone by and you're better."

"Real fucking considerate aren't ya."

~~~

As the days go by, we watch in surprise as the view count keeps rising and the purchases alongside it. In a just a week, the videos have got more than a hundred thousand views with several grand in purchases with only a little slowing.

One day Alex finally decided things were doing well enough and tells me, "Well, I guess this is gonna be a regular thing then. Lucky you."

~~~

Our videos keep getting more popular because of the free use type, casual theme and the fact Alex seemed like such an easy anal slut. We easily managed to raise enough money for our holiday across Europe, but even that, we kept up the videos. For one, I assfucked Alex on a chair, she dangled her legs over the arms, giving me open access. We chatted while I pumped her ass with deep strokes; she just sat there and let me drill her ass relentlessly, both of us ignoring her pussy all the while. I eventually filled her ass and she as usual, ate it.

In one popular video, I was taking Alex's ass while she was kneeling on hardwood flooring. It was fine at first but after a while of pounding into her ass, I could tell her knees were hurting being pressed into the floor like that. Alex was too proud or stubborn to admit it hurt though so I just leaned more and more of my weight onto her as I assfucked her harder, trying to see if she'd complain but she never did. When I eventually filled her ass with semen, I had her lean back and push out the anal creampie onto the floor. When I pulled her up and turned her around, she gave the mess on the floor one look and said with an annoyed expression, "You're going to make me eat that aren't you."

"Yup."

"Ugh, gross." Alex shook her hands out to psyche herself up for a moment before she leaned down, pursed her lips and nosily slurped the cum off the floor. She straightened out and opened her mouth for me and the camera to get a good look, even swirling her tongue around and gargling a little before she loudly gulped it all down.

It wasn't something we planned on doing; it was just something I sprung on her again. Alex might get a little annoyed at first but would quickly get over it. In fact, as things continued, I'd noticed she complained less and less about the surprises I gave her and just went along with them.

~

Another popular one had us playing FIFA together while Alex bounced her ass on my cock. She'd have to go ass to mouth every time I scored and could swap to her pussy for a little while if she did, she didn't play too well with all the distraction. I finished in her ass after bending her over upside down. Alex gave me a confused look while I was maneuvering her around but just went along with it like I knew she would.

Once I had her folded over herself, I told her to push the creampie out. Posed like that, she realized what I was aiming for, getting her to push the creampie out into her own mouth and face. We'd gotten to the point where even something this obscene didn't get anything more than a surprised out of her. She played along and pushed, opening her mouth and sticking out her tongue to catch the creampie. Some of it landed in her mouth or on her tongue, but some splattered on her cheeks and lips too. At this point Alex didn't need to be told what to do, she just scooped the cum off her face and into her mouth before gargling a little and swallowing it like usual, after all, eating my cum out of her ass is what friends do.

It was becoming more than just a thing for the videos too. When I visited Alex one day, she was busy with something on her laptop, instead of just ignoring me until she was done, she said, "Hey man, sorry I can't talk and I'm gonna be a while, typing a lot of shit up."

"That's cool," I reply.

After a little while I me just awkwardly hanging around while she silently worked, Alex eventually says, "Dude you don't have to sit there twiddling your thumbs, just iunno, use my asshole while you wait."

"You want to film something?" I ask, confused.

"No just pump my ass if you want to kill some time."

"Are you serious?"

Alex shoots me a confused glance, "Yeah? Why wouldn't I be? You assfuck me all the time anyway, how is this any different?"

The question stumps me for a moment, "It's hard to explain, that feels more business-like? This feels more personal."

"Yuck, stop with the feelings. Dude, you've been in my ass so much, I don't even care anymore. But if you don't want to, then don't."

Shrugging, I take her up on the offer. Somehow, it feels better without the cameras rolling, like she isn't doing it for any reason beyond just letting me fuck her.

"God it feels so good being in your ass Alex, you've got no idea."

"Yeah, well, good for you man, enjoy it."

"The first time it was amazing though, shame it can't be like that all the time."

Alex turned to give me a annoyed look, "Oh gee, I'm sorry my asshole isn't tighter since you've been fucking it all the time. Dickhead."

"Sorry, sorry, I didn't mean it that way. I just meant the first time you brought it up it was like mindblowing, the fantasy and all that, now it's just casual sex. Sorry, I do appreciate this Alex."

"Oh OK. Wait, fantasy? Huh, didn't expect that. Didn't seem like you spent afternoons fantasizing about getting into my pants, bet this must be a real dream come true," she said smugly.

Rolling my eyes I replied, "That's not how it is."

Mockingly Alex says, "Sure, sure, why don't you just get back to my ass and let me finish this up."

~~~

I obviously started buttfucking Alex a lot more after that. And as an added bonus, she still kept up the routine of eating the cum out of her ass too. She got the message pretty soon and any time I came over, her pants would come off and she'd ride me with her ass while we hung out or played games. I was pretty happy with how slutty Alex had become, she wouldn't so much as bat an eye at sucking her ass off my cock anymore, even offering it pretty often.
One time I headed over to Alex's in a bad mood because of some work stuff, she noticed how shitty I was being and asked what was wrong. When I told her what was up, she said simply, "That sucks man," then pulled down her shorts and added, "You wanna take it out on my ass then? Gape me a bit or do some ass to mouth? That always perks you up." That's was when I knew she really was my best friend.

~~~ Epilogue

Our relationship really had been changing Alex, the casual assfucking changing how she was viewing sex. She told me about how one of her guy mates was complaining about a dry spell, so she just offered him her asshole. After a bit of shock and disbelief, he eventually did fuck out Alex's ass. She goes on to tell me the story, "Yeah, I've been letting my guy friends just fuck my ass if they ever really want to blow off some steam or just have some fun, I just don't see any reason not to y'know? It's not like I care and they get a kick out of it."

"Wow. That's... You're a really good friend."

Alex purses her lips and nods her head dramatically, "I know, I'm too nice for my own good. I even have good reasons sometimes. I've got this one mate Joe whose girlfriend never lets him put it in her ass and he's apparently been dying to try. So I told him he could try out mine; now he just works it out of his system with mine and stops pestering his girlfriend."

Alex had gotten very popular with her guy friends, and happened to make a whole lot more of them. Word was getting round and everyone was starting to learn Alex was a really good friend to have. Apparently all of them were taking advantage of Alex's new outlook and keeping her holes well fucked. Hearing about the new friends she's made gives me an idea for an anal gangbang video and when I brought it up with Alex, instead of any hesitation or worry, the thought of dozens of guys taking turns wearing out her asshole doesn't seem to faze her, all she said was, "Dude if you want to grab a few mates to gangbang my ass, go for it, sounds like it could be fun for you guys."

I managed to round up more than 30 of her friends for the video. Like we decided at the beginning, Alex's specialty was anal and lots of it, so the gangbang was obviously going to be all anal and oral. Starting from the smallest to biggest, the guys and I spent several hours churning Alex's ass out until it really was a fucked out wreck by the end. Throughout almost the whole video, there was hardly a minute where Alex was left without a cock in her ass or mouth. She methodically took care of every guy regardless of roughly she was being treated, even pushing the limits further than any of the guys dared.

Alex had become a total whore and she hadn't even realized it, almost an hour into the shoot she'd started getting bored I think. Wanting to speed things up, she suggested, "You guys want to try some double anal? We'd go a lot faster two at a time and plus it'd look real good with two of you trying to just fuck my ass all up, some guys are real into that."

Despite shock at the suggestion, the guys wasted no time enthusiastically taking Alex up on her offer. A few minutes later she may have ended up regretting the offer since two in the ass wasn't something she could handle as easily as one, it was like our first video together all over again with her squealing and squirming all over the place. To her credit she didn't pull out and endured it all; gritting her teeth and letting two guys saw in and out at a time.

~~~

Still, as tough as Alex was, if the guys double fucking her ass ever went too fast or deep, Alex would start squirming all over the place, unless she had something distracting her. The guys and I noticed when someone was fucking her throat, she'd squirm a lot less. So we decided to distract her by jamming our cocks down her throat, keeping them there until she was desperate to breathe and slapping our thighs. While she was occupied like that, the two in her ass were free to go all out, pounding it for all it was worth. It was a good strategy because she didn't seem to notice how roughly we were tearing up her ass when she was choking on dick. By the time we were done, her asshole looked like an overstretched wreck.

We ended the video with the guys shooting their loads up her ass one by one, which she in turn pushed out and collected in a bowl. The scene ended with her face buried in the bowl lapping up cum and her fist plunging wrist deep into her own ass.

The video became massively popular so I suggested we make these little anal gangbangs a weekly thing for Alex, with fans invited to join in if they could make it. Alex agreed as usual without batting an eye.