Friends with Benefits

“Hey Simone, could you put me in a friends with benefits like scenario? Just make up a story you’d think I’d like and fill in the details?”

“I sure can, I’ve collected a large enough personalized dataset that I think I’ve got a pretty good read on you. We can do it like before where I just plop you into a setting and you figure things out as you go, or if you give permission, I can just inject knowledge of the situation so you can do some roleplay if you want.”

“Having the machine insert memories and information into my head seemed a bit dangerous, but whatever, I agreed.”

“Alright James, compiling now, stand by.”

In an instant, a flood of new memories and thoughts entered my mind and I found myself in a strange, yet completely familiar room.

I had only met Kacie a few weeks ago during a party at a mutual friend’s place but we had pretty much immediately become good friends. We basically ignored the people we came to the party with in favor of chatting with each other. We’d been hanging out pretty persistently since then, now I was hanging out at her place playing some Rocket League and generally sucking. Eventually the topic veered towards relationships and how I had recently broken up with my girlfriend Kate. Kacie was trying to coax the reasons out of me but I didn’t want to come across as a pervert so I stubbornly kept my mouth closed, Kacie seemed to take that as a challenge.

“Why are you being so cagey about it?” she asked.

“Why are you so insistent on knowing? You know you’re traumatizing me right now by reminding me constantly.” I countered.

“Nuh uh, lies. You seem more nervous than sad about it so you definitely aren’t sad about it being over, which just makes it so much more interesting.” After a pause she adds “Did you cheat on her? I won’t judge. Wellm I will judge but not much.”

I snap my head to face her and say, “No, no, nothing like that. I guess you could say we just weren’t compatible is all, does that satisfy you?”

“Nope. But before we continue the interrogation I’ll grab us some more drinks.”

Kacie got up from the couch and went into the kitchen. It was bloody hot these days so we were wearing pretty light clothing, Kacie was wearing these really hot sports shorts so it was always a treat seeing her walk off. I’d always been a leg and ass guy and Kacie basically ticked all my boxes when it came to that, her legs were amazingly svelte and her butt irresistibly cute. This combined with her British accent she kinda reminded me of Tracer from Overwatch since she had the same kind of short brown hair, though the accent was the wrong type, it was the posh kind. When she came back she was holding a couple beers this time, an opener and a bowl of chips. It was a bit much to juggle so she dropped the opener, it managed to somehow fall underneath the coffee table. Kacie set stuff she was holding down and got down onto her knees to look for the thing. She was on all fours giving me an eyeful of her ass wiggling around as she searched for the opener, the bottom of her cheeks poked just slightly out from underneath the rim of her shorts and I couldn’t help but stare. And since breaking up with Kate I hadn’t had sex in quite a while, so the results were pretty predictable, I popped a chub. I quickly grabbed one of the couch pillows and threw it over my crotch in the worst, most transparent attempt in the history of man to conceal an erection.

“Got it!” Kacie said triumphantly just then, turning around waving the opener in one hand. She immediately notices the pillow I was holding against my crotch and gives me a bemused look.

“So now that you aren’t with Kate anymore I’m guessing you aren’t getting any action."

“You can tell huh?” I deadpan

“I’m observant like that… Y’know that makes me think, was it a sex thing?”

“Was what a sex thing?”

“The breakup, did you break up because of a sex thing.”

I must’ve left something slip on my face because Kacie quickly added a knowing “Ah” and slid back down onto the couch next to me. “Ah? What do you mean ah? I never said it was, you’re crazy woman.”

“It was a sex thing wasn’t it, admit it.”

“Let’s go back to playing alright, I want to lose to teenagers some more.”

The next 30 minutes were interrupted with periodic accusations, “Did you break up because one of you wanted to have an orgy and the other didn’t? Or maybe it was a threesome. Butt stuff? Was it butt stuff? Oooh she had a kink for public sex, or, or role play, weird, weird role play. No, it was BDSM wasn’t it, she didn’t like the ropes! Ew, don’t tell me you tried to pee on her”. My hard on still wasn’t going away and the conversation wasn’t helping matters there, I eventually just caved and half yelled, “It was butt stuff! It was butt stuff OK? Satisfied?”

“She wanted to peg you?” She asked tilting her head

Smiling and chuckling a bit I reply, “No, I wanted to put it in hers.”

“I knew it alllll along,” She said mockingly then added, “still, it doesn’t make too much sense; you don’t break up with someone just because they asked to stick it in your butt once.”

“Uh, it was a bit more than once. A lot more actually. I kinda nagged her about it constantly to be frank. I’ve never done it before and I’ve become a bit obsessed.”

“Obsessed?”

Well, I’d opened the floodgates, might as well let it all out and vent, “Yeah, a lot of my porn is anal now. I jerk off to it a lot and think about doing it with a girl a lot more. I’ve just never gotten the chance.”

Kacie nods along and when I’m done is silent for a long while. I’m suddenly nervous again that this’ll change her opinion of me. I don’t know what to say to undo things so I awkwardly stay silent. After a long silence, Kacie finally breaks it to say, “You know, I could help you with that.”

My heart starts beating faster at this but I don’t want to misinterpret things so I clarify, “With what?”

Pointing to the pillow still on my crotch she says, “That.”

My hearts full on racing now, that wasn’t something I expected to hear but was pretty excited to hear it. “Uh, how would you help?”

“Weeeell, I’m hot and I don’t mind anal. You can work out your obsession in my asshole,” Kacie said simply with a slight lopsided smile.

My cock jumped at that and I felt like my heart skipped a beat then went into overdrive to compensate. “Kacie, are you fucking with me right now? If this is a joke, not cool; it’s just not right to get a man’s hopes up like this.”

“200% Legit here James, honest. I mean look, if you said it was because she wouldn’t let you pee on her, I’d be no help here, but butt stuff? That I can do. I like you well enough James, I just wouldn’t mind letting you in my ass when we’re hanging out.”

“Are you sure though? Getting it out of my system might take a lot of work, for a long time,” I say hopefully.

Kacie laughed a bit and shrugged, “Like I said, I don’t mind anal. It’s never hurt or bothered me. Actually kinda like it to tell the truth. Look.”

With that, Kacie pulled down her shorts, leaned back and swung one of her legs over the back of the couch. Right there in her ass was the metal base of a butt plug. I stare dumbfounded at her ass, practically drooling. While I’m staring, Kacie grips the base of the buttplug and pulls it out, it was surprisingly large, about 2 and bit inches large at its widest but it came out easily all the same. Instead of putting it aside, she lifted it up towards her pretty face, my eyes following like I was hypnotized, and popped it into her mouth casually, making my cock twitch. God, how easily and unhesitantly she did it was turning me on like nothing else. She lolled it around in her mouth with her tongue, maintaining eye contact with me the whole time. Speaking with a full mouth she adds, “And that’s not the only thing I can do.”

“Yeah, I’ve noticed when guys like anal they tend to like ass to mouth too. You all just like doing dirty things to pretty girls don’t you?”

I nod.

“Well, it’s all yours then.” She says giving her ass a slap. She finally takes out the buttplug from her mouth and hugs her legs against her chest with one arm hooked behind the knees.

I ask her, “So, is this like a friends with benefits deal or a one-off?”

“I guess, as long as things don’t get weird, I’m happy to just let you get off in my ass whenever. Is that how friends with benefits works? I’ve never actually done it before.”

Swallowing hard and feeling overwhelmed I’m slow to react, but I do start undressing eventually. I grab my wallet and take out a condom. I’m halfway through opening it when Kacie interrupts playfully, “Please, I’m not cruel, I’m not going to make you wear a rubber your first time, I mean unless you want, but you can just bareback me otherwise and really feel it.”

“Kacie I think I love you.”

She lets loose a light laugh. “Sorry James, we’re just friends.”

Pulling out my rock hard cock, I move to start rubbing it against her pussy. When I’m prodding her there and putting in just the tip, getting it glistening in her wetness Kacie interrupts again. “Pussy’s optional just so you know.”

“What do you mean?”

“You don’t have to feel obligated to fuck my pussy, could just skip that part if it’s all the same to you. If you’re really obsessed about ass then you can just do me there if you want, it’s fine by me.”

“But I don’t have any lube, I was trying to use your pussy for that instead, I can’t go in dry. I mean, can I?”

In reply Kacie moves her other hand towards her asshole and slips 3 fingers easily inside, hooking one side of her asshole and pulling it open, showing me a lopsided little gape. “Does this hole look like you need to go slow? Trust me, you can stick it in now fine.”

I was in shock at how of a whore Kacie secretly was, absolutely over the moon but Kacie must have misinterpreted it as hesitation or **** so she adds, “Don’t pussy out now. I mean how often is a girl going to just give you free usage of her asshole James? You should make the most of this chance while you can and milk it for all its worth. My ass isn’t made out of tissue paper, don’t be afraid to play rough, really go ahead and enjoy it.”

Taking her advice, I aim my cock at her asshole and push forward. I slipped in with practiced ease and began slow deep strokes, savoring the feeling. It was everything I hoped for and more.

Kacie asks me with an inquisitive look, “Enjoying yourself? Is it everything you hope it would be?”

“God you have no idea how good your asshole feels.”

Laughing lightly Kacie replies, “Well have fun. You mind if I get back to playing Rocket League?”

I liked the sound of that more than I care to admit, “No it’s fine, go ahead.”

She grabs the controller again and resumes playing while I’m steadily picking up my pace and fucking her faster. By the end of her match, I’m slamming into her asshole decently fast and she’s barely paying attention to me.

“Jesus Christ, I’ve never seen anyone take it like this.”

“Yeah, I know, I’ve always known I’ve been a bit weird this way. You hear a lot of horror stories when it comes to anal. Guys that put it in too fast, girls screaming in pain, blood, shit and all that. That never happened to me. When I was young, one day my boyfriend slipped it up my ass without asking me and well, I just didn’t mind. For the longest time I just thought ‘I don’t mind anal, guys like it, why shouldn’t I let them.’ I’ve actually kept that up for so long, at some point I stopped liking it in my pussy. Now anal is pretty much the only thing that gets me off, I can barely cum without it anymore. To be frank, I don’t even like it when guys waste time with my pussy now. I think I’ve always been an anal only girl, but I’ve only been embracing it lately.”

“That’s so fucking hot,” flicking my eyes downward I ask, “So I can really do this whenever I want?”

Shrugging she replies, “Yup, like I said I don’t mind, my asshole’s yours whenever need want it, just help yourself.”

Wanting to change positions, I grab Kacie and move her off the couch and onto the floor, laying her flat on her stomach, giving me much better view of her perfect ass. I feed my cock into her ass slowly this time, enjoying sight of my cock slowly disappearing into her ass with ease as she keeps playing. I slowly speed up again to my old tempo, and within a minute I’m pounding into her as fast as I can but Kacie still doesn’t seem to mind, I’m so glad I met her.

After a few more minutes of fucking her like this, I transitioned into pulling entirely out then plunging back in down to the balls, one of my favorite things to do. Suddenly slamming in then leaving her feeling empty just as fast like that should have bothered her but she was taking me like a pornstar. I keep this up for long minutes, curious to see if Kacie ever says anything about it but she doesn’t. Wanting to see just how much she’d let me get away with, I tried something I’d seen in porn, I grabbed my cock by the base while it was still buried a third of the way inside her and pulled up against her asshole. Pulling up like I did, my cock deformed her asshole, making the skin stretch and bulge before finally popping out with a wet sound and leaving her asshole looking like abused meat. I put it back in immediately just as deep but this time stirred my cock around her guts instead of pulling up, making even more of mess of her ass. I got into a routine of swapping between the two motions for a long time, all the while her hands are still on the controller and eyes still glued to the screen. The longer I did it, the more shocked became at Kacie and how she didn’t seem to mind. I slowed down and changed to just casually dipping half my cock into her asshole, slipping past the ring of muscle again and again to tell Kacie, “This is crazy; I can’t believe this really doesn’t bother you. Pornstar’s don’t even do this stuff.”

Laughing she replies, “Yeah I know, don’t think I don’t notice you doing all that crazy shit. It’s funny, I know you’re turning my ass inside out and I shouldn’t be okay with it, I mean most girls would be screaming their heads off, but iunno, I’m weird, I just don’t mind.”

“Well I don’t think you’re weird, I think you’re amazing.”

“Yeah yeah, you’re just saying that because I’m letting you blow out my asshole you pervert.”

“You say that like it’s a bad thing.”

“Alright, shut up and let me play. By the way, are you going to be done soon?”

“I’m close.”

Kacie doesn’t reply immediately but pauses for a moment before shyly asking, “Hey uh… That stuff you were doing before… Y’know the crazy pornstar stuff… You think you can do a bit more of that? It felt… Interesting. I don’t usually feel much of anything getting it in the butt, but that was different.”

God damn, the fact she was actually asking me to **** her asshole so roughly was turning me on like nothing else. I gladly went back to the stirring and pulling moves while occasionally bottoming out, roughly using her asshole like it was just a sex toy.

With her eyes closed Kacie groans out, “Don’t hold back, give it all you’ve got, hard as you can, really wreck that ass.”

God damn she was hot for the abusive stuff, I couldn’t believe she was getting off to having her asshole ruined. I happily obliged her and stepped up the assfucking another notch, giving her rapid full strokes until her ass gaped permanently open while I fucked her.

Kacie softly moans out, “Oh yeah, that’s good, keep doing that.”

After 15 minutes I notice a change in Kacie’s body language, she’s relaxing more and more and before I know it, I feel her body tighten up and start to spasm beneath me. I can’t believe she’s getting off on this and actually cumming, it tipped me over the edge and I felt my balls tighten, I started relentlessly bottoming out in her as fast as I could as I unloaded a torrent of jizz into her ass.

I slid out once I grew soft and spread her cheeks with my thumbs so I could enjoy seeing the aftermath. Her asshole gaped easily, showing off her cum coated rectum, glowing with an angry red shade thanks to being fucked raw. It looked like it should hurt but Kacie didn’t seem to mind. “Wow,” I say absentmindedly. This gets Kacie curious and she asks me to take a photo on her phone so she can see, I do.

Looking at her ass in her phone she says, “Wow, you really did a number on my asshole,” before giving me a sly look and adding, “are we still on for tomorrow? Because I think I could get used to this.” Kacie suddenly laughs to herself and says, “I think I was made to get assfucked James.”