AnnaSophia Robb Goes Anal Sex Story

AnnaSophia Goes Anal
Author: Robertdoc
Celebrity: AnnaSophia Robb
Warnings: M/F, cons, oral, anal, blowjob, fingering, cunnilingus, analingus, doggy style


It was a nice, normal night out in Long Island – a nice night to walk down the streets with a friend. A friend who was filming a television show here several months out of the year. A friend who was starring in this TV show – even if it was on the CW and was a prequel series.

A friend who happened to be AnnaSophia Robb, of several Disney and young adult films, but currently of “The Carrie Diaries.” Only about over a million people knew about her and her show, according to the Nielsens. I wouldn’t have heard of it if they didn’t film in town, and if she didn’t come to my coffee shop every day, and if we hadn’t become actual friends for the last three months.

But even if regular people didn’t know her or her show, a lot of Internet people did. If only because they made gifs starring her most famous body part. Not her big, beautiful blue eyes, blonde hair, gigantic smile or slender legs – but something big between the smile and legs.

Something that some jackass behind us just got away with pinching.

“Hey!” AnnaSophia squealed, turning to slap the creep who pinched her…rather ample backside. Which was sticking out even more than usual in her blue jeans. Still, it wasn’t an open invitation.

The fact she acted faster than me to slap him was kind of troubling. And so was what he actually did, of course. Regardless of…

“Easy, easy, I’m gone,” the creep assured, looking far too satisfied already. That satisfaction, my ego, my need to defend a friend – and some jealousy I did NOT want to think about – made me spring to action when his back was turned.

If he was going to grab AnnaSophia’s ass, I was going to kick his. I mean, literally kick him in the ass with my right foot.

Maybe it wasn’t so tough that I took AnnaSophia’s wrist and ran away with her before he punched me back. But hell, if he wanted to be a coward, I could be too.

The coward ass grabber cursed and chased us for about a block, but we were too fast for him. Nevertheless, we kept running for another block until we actually reached my apartment building. With the ‘danger’ gone and the ability to breathe coming back, me and AnnaSophia even managed to start laughing.

We kept laughing off and on until we reached my actual apartment. Yet by the time we settled down for a drink on my couch, AnnaSophia wasn’t in a laughing mood.

“That’s how it’s going to be, isn’t it? I’m surprised that was the first time,” she commented.

“First time you saw a literal ass kicking?” I tried to guess, though I knew I was probably wrong.

“It’s not his ass I was talking about,” AnnaSophia stated. “Mine came out of nowhere, you know! It’s not going away anytime soon, though. Neither are jackasses like him. They’ll just keep pinching and groping and jacking off to it. If I had sex more often, they’d probably wear it out by now! Or they’d want to!”

AnnaSophia got up, her back turned to me – a most ironic position, considering the topic of conversation. I took one quick look at her hypnotically obscene rear, before she could realize I was part of the problem she talked about. Albeit the nicest example of the problem.

“I just started having sex, you know,” she didn’t make it any easier at all. “There’s a lot to do, but…all anyone’s gonna want is my ass, I know it. Most of the time, they probably won’t be good at it. It’d be nice if I could…at least get it right off the bat. Maybe that’d set the tone for years of ass play.”

I had no answer to that, and few would probably make me look good. Especially with all the images in my head right now. They weren’t exactly new images – or ones that went away for more than a few days around her – yet I knew how to control myself. At least when she wasn’t testing it this much.

“Wait…that’s it!” AnnaSophia yelled. “I need a great first time! Even if it doesn’t get better from there!”

“I thought you already started having sex,” I played dumb, for one reason or another.

“Not that kind of sex!” AnnaSophia still unintentionally played coy. “If guys are gonna just go after my ass…I should find one that’ll be good to it first! I can at least lose my anal virginity the right way.”

“Jesus…” I groaned in frustration and other emotions. “You do know finding the right guy’s a crapshoot? When it comes to any virginity?”

“Yeah. You can’t always stumble onto guys who would kick someone’s ass for you. Literally,” she got right to the point. And that point practically made my throat close.

“You’re not serious,” I told her before it all spun out of control – the situation, our friendship and my self-restraint.

“Who better than a friend who respects me? Or at least lusts after me to a respectful point?” she asked, making me wonder how discreet I’d been at certain moments – and poses – of our friendship. “You want to stay friends with me, right? Ass or not?”

“Um….sure, of course,” was a weak answer, albeit an accurate one – and the best I could muster.

“Then you sure wouldn’t want to fuck my ass the wrong way. You’d take extra good care of it for it’s first time. Even if…not every guy after that doesn’t think that way,” AnnaSophia figured.

“And you…really don’t want to wait for one of the good ones?” I checked again.

“There’s probably not much time to waste. Why take the risk?” she answered.

“So I’m not a risk? I’m just the good, safe nice guy good for a b…” I barely kept myself from saying booty call. That stupid joke, and the stupid way I was objecting, wasn’t helping me out. Then again, there were some unflattering things I could take from this.

“No one who kicks ass like that is all good. I know I can trust you to be the good kind of bad,” AnnaSophia made it sound better. “If you were that creative against that guy, who’s a total ass….I’ll bet you could be the right kind of creative for mine.”

Yep, it was way too stupid to keep objecting now. The only problem left was her setting the bar too high.

This was AnnaSophia Robb’s ass we were talking about. This was an ass that belonged to a friend. I could ravage it then and there, and had frequently thought about it – but that wasn’t all she was asking for. It wasn’t all I wanted to do with it either.

But if she riled me up and got me hot like this, I wouldn’t think ahead enough to deliver. This was a task one needed to be fully prepared for.

“You know…I’m extra creative after I’ve had dinner. Too bad it’s too late for one now,” I reflected. “How about we take care of that early tomorrow night? Then we can take care of the rest.” That was good. Less than 24 hours to get ready should be enough – or be enough to make her come to her senses.

Yet when AnnaSophia thought about it, gave me her brightest smile and agreed, I was stuck with this calculated risk.

Somehow, I let her head back home after a few more minutes, and after choosing a place to meet up for dinner tomorrow. Somehow, I got myself to sleep before 1 a.m. afterwards. Somehow, I kept my hand off my cock for more than a few minutes before getting out of bed that morning.

By the time work ended and it was almost dinner time, I let myself have a…practice run. If AnnaSophia hadn’t changed her mind and would be….coming back here after dinner, I wasn’t going to let this be…a quick dessert. I had to know I could….stand tall as long as possible, in spite of the mighty task ahead.

It wasn’t like this was the first time I jacked off to her ass. It wasn’t as if I didn’t cum earlier than I wanted to in those times. But the thought of actually being hours away from seeing it, touching it, fucking it, devouring it…

It all made me break my record time by about a full minute. Which wasn’t exactly encouraging.

As such, when I got to the restaurant we agreed to, part of me almost wished she wouldn’t show up. It would spare me the embarrassment, and probably mean she was okay and thinking straight too.

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