Tomboy

“Hey Simone, I’ve been thinking, I’ve always had a bit of a thing for tomboys and I wanted you to come up with a scenario that put me with one.”

Simone instantly respond as usual, “Tomboy huh? We can do that easy, the personality archetype is actually pretty similar to some assets you’ve come across already early on. 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. Compiling, stand by.”

“Hey that sounds good, plug me in whenever Simone.”

I was barely capable of recognizing the transitions anymore. I just found myself with Alexa, who I suddenly now knew preferred to go by Alex. We’d been friends since we were little kids, I liked her a lot when I was little because she was just like one of my guy friends, but pretty to look at. Can’t say things have changed really, having 5 brothers must have rubbed off on her a lot. We were hanging out at her place and having a sesh. She was complaining to me about how tuition, rent, and all the unexpected expenses that keep cropping up was killing our holiday plans. We keep planning to go backpacking across Europe together during the break during the summer break but never actually do.

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 pretty gorgeous and would be a total knockout if she ever cared about that sort of thing. She wasn’t lazy though, she surfed pretty frequently so still had a toned body. 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 of the info dump, saying, “Fuck me James, at this rate I’m 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 ****? I hear **** 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 she can peg 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, like on manyvid and chaturbate. 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. 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, saying “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 on Pornhub or something?”

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 and expect much of a response.”

Thinking it over, Alex says, “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, “Sure thing. See ya Alex.”

***

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. Alex talks to me from couch where she’s on her laptop, saying, “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 though, saying, “I mean, you know I already love it, I’ve told you enough times of 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.”

“Yeah that part you like.” Alex then pulls a confused look, “But the bored part? Where’s the fun in that?”

Struggling to explain, I say, “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.”

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 sweatpants 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 **** 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 your OK with being fucked harder now?”

She replied, “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 ass. Alex wasn’t kidding about not having done anal before, she’s deliciously tight and snugly hugging my whole cock. 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 to say, “Shut up,” punctuating it with a sudden thrust into her ass.

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 her ass. She 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 prematurely.

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 could 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.”

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 dropping it back in as rapidly as I can. The hellish treatment for her feels incredible to me; entering 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. I soon feel a familiar pressure building in my balls. It’s like a switch turns on in my head, making me grab hold of both Alex’s tits, squeezing and mauling them with sudden **** while rutting her ass rabidly. Incredibly Alex keeps still and doesn’t try to run away, just leaves her ass where it is, letting me ravage her asshole. A minute of the **** goes by before I finally slam in 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, it’s what I’m here for.”

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 oblige and 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. 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, 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 a 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 its 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 in a tone suggesting otherwise.

“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.”